#------------------------------------------------------------------------------ #$Date: 2024-12-11 01:36:52 +0200 (Wed, 11 Dec 2024) $ #$Revision: 296832 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249683.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7249683 loop_ _publ_author_name 'Shi, Linlin' 'Guo, Zhiqiang' 'Luo, Xiaofang' 'Hou, Lingli' 'Wu, Hongchang' 'De, Ruiyu' 'Huang, Xin' 'Wang, Ting' 'Hao, Hongxun' 'Wang, Na' 'Zhou, Lina' _publ_section_title ; Chiral resolution of dl-leucine via salifying tartaric acid derivatives ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D4CE01043D _journal_year 2025 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C20 H17 O8), 2(C6 H14 N O2), H2 O' _chemical_formula_sum 'C52 H64 N2 O21' _chemical_formula_weight 1053.05 _chemical_name_systematic 'D-leucinium D-di-p-toluoyltartrate semihydrate' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2024-05-02 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-09-27 deposited with the CCDC. 2024-12-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.0490(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 27.9114(2) _cell_length_b 12.85360(10) _cell_length_c 15.90080(10) _cell_measurement_reflns_used 41533 _cell_measurement_temperature 128.15 _cell_measurement_theta_max 78.7260 _cell_measurement_theta_min 3.2870 _cell_volume 5482.27(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 128.15 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -25.00 94.00 0.50 0.50 -- 5.00 57.00 120.00 238 2 \w -28.00 94.00 0.50 0.50 -- 5.00 38.00-120.00 244 3 \w -82.00 41.00 0.50 0.50 -- -48.80 38.00 0.00 246 4 \w -82.00 41.00 0.50 0.50 -- -48.80 70.00 35.83 246 5 \w -83.00 41.00 0.50 0.50 -- -48.80 72.00-120.00 248 6 \w -79.00 41.00 0.50 0.50 -- -48.80 57.00-150.00 240 7 \w -79.00 41.00 0.50 0.50 -- -48.80 57.00 90.00 240 8 \w -199.00 -80.00 0.50 0.50 -- -110.00 -50.00-167.12 238 9 \w -199.00 -75.00 0.50 0.50 -- -110.00 -36.00 105.63 248 10 \w -144.00 -21.00 0.50 0.50 -- -110.00 72.00 120.00 246 11 \w -144.00 -21.00 0.50 0.50 -- -110.00 72.00 60.00 246 12 \w -144.00 -21.00 0.50 0.50 -- -110.00 72.00 30.00 246 13 \w -144.00 -21.00 0.50 0.50 -- -110.00 72.00 90.00 246 14 \w -144.00 -21.00 0.50 0.50 -- -110.00 72.00-180.00 246 15 \w -199.00 -80.00 0.50 0.50 -- -110.00 -57.00 30.00 238 16 \w -144.00 -21.00 0.50 0.50 -- -110.00 72.00 -60.00 246 17 \w -112.00 -85.00 0.50 0.50 -- -110.00 -68.00 -81.40 54 18 \w -120.00 -94.00 0.50 0.50 -- -110.00 72.00 -30.00 52 19 \w -139.00 -22.00 0.50 0.50 -- -110.00 72.00 -90.00 234 20 \w -199.00-117.00 0.50 0.50 -- -110.00 -53.00 -47.71 164 21 \w -160.00-104.00 0.50 0.50 -- -110.00 -57.00-150.00 112 22 \w -79.00 -53.00 0.50 0.50 -- -110.00 72.00-120.00 52 23 \w -101.00 -75.00 0.50 0.50 -- -110.00 72.00 0.00 52 24 \w -198.00-138.00 0.50 0.50 -- -110.00 -72.00 0.00 120 25 \w -115.00 -89.00 0.50 0.50 -- -110.00 -72.00 0.00 52 26 \w -198.00-110.00 0.50 0.50 -- -110.00 -42.00 81.94 176 27 \w -141.00 -80.00 0.50 0.50 -- -110.00 72.00-120.00 122 28 \w -198.00-151.00 0.50 0.50 -- -110.00 -68.00 -81.40 94 29 \w -61.00 -35.00 0.50 0.50 -- -110.00 72.00-150.00 52 30 \w -196.00-146.00 0.50 0.50 -- -110.00 -28.00 -14.19 100 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0237827000 _diffrn_orient_matrix_UB_12 -0.0923706000 _diffrn_orient_matrix_UB_13 -0.0585032000 _diffrn_orient_matrix_UB_21 -0.0522645000 _diffrn_orient_matrix_UB_22 0.0441264000 _diffrn_orient_matrix_UB_23 -0.0066773000 _diffrn_orient_matrix_UB_31 0.0017022000 _diffrn_orient_matrix_UB_32 0.0623589000 _diffrn_orient_matrix_UB_33 -0.0817966000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0150 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 48515 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.971 _diffrn_reflns_theta_min 2.892 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.52304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)' _exptl_crystal_density_diffrn 1.276 _exptl_crystal_description block _exptl_crystal_F_000 2232 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.284 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 5004 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.07(4) _refine_ls_extinction_coef 0.00012(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 700 _refine_ls_number_reflns 11329 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+3.0644P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1079 _refine_ls_wR_factor_ref 0.1081 _reflns_Friedel_coverage 0.841 _reflns_Friedel_fraction_full 0.960 _reflns_Friedel_fraction_max 0.914 _reflns_number_gt 11216 _reflns_number_total 11329 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ce01043d2.cif _cod_data_source_block p20240501c _cod_database_code 7249683 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.878 _shelx_estimated_absorpt_t_min 0.818 _reflns_odcompleteness_completeness 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2. Restrained distances O6-H6 = O14-H14 0.85 with sigma of 0.01 3.a Free rotating group: O21(H21D,H21E) 3.b Ternary CH refined with riding coordinates: C9(H9), C11(H11), C29(H29), C31(H31), C42(H42), C44(H44), C48(H48), C50(H50) 3.c Secondary CH2 refined with riding coordinates: C43(H43A,H43B), C49(H49A,H49B) 3.d Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C6(H6A), C7(H7), C15(H15), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27), C35(H35), C36(H36), C38(H38), C39(H39) 3.e Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C40(H40A,H40B, H40C), N1(H1D,H1E,H1F), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), N2(H2A,H2B, H2C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C) 3.f Idealised tetrahedral OH refined as rotating group: O18(H18A), O20(H20) ; _shelx_res_file ; TITL p20240501c_a.res in C2 p20240501c.res created by SHELXL-2018/3 at 18:48:17 on 02-May-2024 REM Old TITL P20240501C in C2 REM SHELXT solution in C2: R1 0.095, Rweak 0.031, Alpha 0.001 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = 0.084 ( 0.030 ) from 4921 Parsons' quotients REM Formula found by SHELXT: C52 O23 CELL 1.54184 27.9114 12.8536 15.9008 90 106.049 90 ZERR 4 0.0002 0.0001 0.0001 0 0.001 0 LATT -7 SYMM -X,+Y,-Z SFAC C H N O UNIT 208 256 8 84 DFIX 0.85 0.01 O6 H6 O14 H14 L.S. 35 PLAN 5 SIZE 0.25 0.22 0.16 TEMP -145 CONF list 4 MORE -1 BOND $H htab fmap 2 53 acta OMIT 8 8 4 REM REM REM WGHT 0.065200 3.064400 EXTI 0.000120 FVAR 0.19940 O1 4 0.590404 0.273604 0.483986 11.00000 0.02760 0.02904 = 0.04173 -0.00185 0.00556 -0.00040 O2 4 0.622098 0.431096 0.529780 11.00000 0.01847 0.02727 = 0.02278 0.00180 0.00162 0.00352 O3 4 0.587450 0.468184 0.359116 11.00000 0.03792 0.03440 = 0.02318 0.00376 0.01317 0.00926 O4 4 0.546129 0.607529 0.387044 11.00000 0.03368 0.03190 = 0.02310 0.00564 0.00666 0.00906 O5 4 0.540533 0.439800 0.647087 11.00000 0.03530 0.03450 = 0.02544 -0.00153 0.01144 -0.01092 O6 4 0.585816 0.573378 0.718061 11.00000 0.03594 0.03115 = 0.01926 -0.00009 0.00685 -0.00741 H6 2 0.583641 0.548851 0.767264 11.00000 0.05911 O7 4 0.615032 0.626399 0.579945 11.00000 0.01848 0.02510 = 0.02510 0.00022 0.00603 -0.00233 O8 4 0.571311 0.768787 0.595112 11.00000 0.03000 0.03170 = 0.04332 0.00252 0.01364 0.00437 C1 1 0.832422 0.195382 0.599278 11.00000 0.03010 0.07469 = 0.05470 0.01384 0.01302 0.01857 AFIX 137 H1A 2 0.853370 0.251352 0.587023 11.00000 -1.50000 H1B 2 0.835410 0.133818 0.564722 11.00000 -1.50000 H1C 2 0.843317 0.178025 0.661696 11.00000 -1.50000 AFIX 0 C2 1 0.778664 0.230801 0.575193 11.00000 0.02815 0.05708 = 0.03394 0.00772 0.00861 0.01235 C3 1 0.740015 0.159877 0.552619 11.00000 0.03704 0.04019 = 0.05525 0.01049 0.01527 0.01465 AFIX 43 H3 2 0.747371 0.087865 0.551001 11.00000 -1.20000 AFIX 0 C4 1 0.690557 0.191960 0.532231 11.00000 0.02919 0.03940 = 0.05228 0.00529 0.00989 0.00702 AFIX 43 H4 2 0.664529 0.141951 0.516889 11.00000 -1.20000 AFIX 0 C5 1 0.679124 0.296738 0.534230 11.00000 0.02501 0.03751 = 0.02519 0.00310 0.00481 0.00808 C6 1 0.717766 0.368916 0.555730 11.00000 0.02712 0.04245 = 0.04489 -0.00401 0.00800 0.00301 AFIX 43 H6A 2 0.710336 0.440962 0.556665 11.00000 -1.20000 AFIX 0 C7 1 0.767056 0.336497 0.575813 11.00000 0.02613 0.05503 = 0.04884 -0.00406 0.00615 0.00239 AFIX 43 H7 2 0.793104 0.386533 0.590090 11.00000 -1.20000 AFIX 0 C8 1 0.626022 0.329514 0.512610 11.00000 0.02605 0.02830 = 0.02194 0.00102 0.00534 0.00442 C9 1 0.574185 0.480296 0.499212 11.00000 0.01638 0.02724 = 0.01968 0.00183 0.00352 0.00125 AFIX 13 H9 2 0.547494 0.427436 0.496366 11.00000 -1.20000 AFIX 0 C10 1 0.568362 0.524661 0.407578 11.00000 0.01759 0.03000 = 0.02000 0.00020 0.00332 -0.00231 C11 1 0.570925 0.563803 0.564341 11.00000 0.01528 0.02774 = 0.02049 0.00256 0.00367 -0.00070 AFIX 13 H11 2 0.541359 0.608680 0.537683 11.00000 -1.20000 AFIX 0 C12 1 0.565248 0.519167 0.649963 11.00000 0.01688 0.02701 = 0.02081 0.00102 0.00518 0.00005 C13 1 0.610997 0.727433 0.599926 11.00000 0.02532 0.02564 = 0.02351 0.00294 0.00754 -0.00163 C14 1 0.660080 0.779696 0.627771 11.00000 0.02787 0.02875 = 0.02778 0.00180 0.00900 -0.00489 C15 1 0.704089 0.726929 0.635400 11.00000 0.02922 0.03560 = 0.04797 -0.00740 0.00814 -0.00303 AFIX 43 H15 2 0.703419 0.654461 0.623388 11.00000 -1.20000 AFIX 0 C16 1 0.749317 0.779025 0.660504 11.00000 0.02760 0.05099 = 0.05923 -0.01058 0.00830 -0.00330 AFIX 43 H16 2 0.779401 0.742341 0.664396 11.00000 -1.20000 AFIX 0 C17 1 0.750902 0.884667 0.680021 11.00000 0.03775 0.04624 = 0.03882 -0.00477 0.00919 -0.01531 C18 1 0.707126 0.936592 0.673256 11.00000 0.04973 0.03431 = 0.05692 -0.00491 0.01652 -0.01322 AFIX 43 H18 2 0.707937 1.008658 0.686839 11.00000 -1.20000 AFIX 0 C19 1 0.661533 0.885405 0.646812 11.00000 0.03921 0.02922 = 0.05411 -0.00312 0.01571 -0.00241 AFIX 43 H19 2 0.631450 0.922574 0.641768 11.00000 -1.20000 AFIX 0 C20 1 0.800561 0.940000 0.707161 11.00000 0.04360 0.06501 = 0.05867 -0.00821 0.01057 -0.02561 AFIX 137 H20A 2 0.822611 0.904454 0.757728 11.00000 -1.50000 H20B 2 0.795536 1.012100 0.722880 11.00000 -1.50000 H20C 2 0.815749 0.939338 0.658480 11.00000 -1.50000 AFIX 0 O9 4 0.575783 0.284731 -0.054837 11.00000 0.02630 0.02892 = 0.03395 0.00000 0.00391 -0.00175 O10 4 0.617445 0.419696 0.022410 11.00000 0.01797 0.02641 = 0.02241 0.00115 0.00291 0.00334 O11 4 0.588489 0.491041 -0.142013 11.00000 0.02983 0.03072 = 0.02096 0.00141 0.00902 0.00041 O12 4 0.537312 0.608127 -0.108182 11.00000 0.03599 0.03434 = 0.02673 0.00818 0.00832 0.01162 O13 4 0.543563 0.428766 0.144357 11.00000 0.03786 0.03675 = 0.02585 0.00038 0.01125 -0.01125 O14 4 0.591639 0.553024 0.223834 11.00000 0.02986 0.03335 = 0.01843 0.00119 0.00499 -0.00151 H14 2 0.591251 0.532185 0.274918 11.00000 0.11621 O15 4 0.621590 0.614592 0.086017 11.00000 0.01977 0.02761 = 0.02510 -0.00242 0.00774 -0.00433 O16 4 0.586610 0.758925 0.124329 11.00000 0.02603 0.02825 = 0.03479 -0.00068 0.00939 0.00067 C21 1 0.798892 0.090375 0.085317 11.00000 0.05207 0.07540 = 0.08725 0.02630 0.02482 0.03793 AFIX 137 H21A 2 0.791367 0.016589 0.072737 11.00000 -1.50000 H21B 2 0.815732 0.099114 0.147726 11.00000 -1.50000 H21C 2 0.820655 0.115340 0.050675 11.00000 -1.50000 AFIX 0 C22 1 0.750868 0.152313 0.061849 11.00000 0.04133 0.05645 = 0.05495 0.01730 0.02052 0.02150 C23 1 0.708561 0.112732 0.003078 11.00000 0.04824 0.03974 = 0.08658 0.00329 0.02651 0.01396 AFIX 43 H23 2 0.709691 0.045790 -0.021625 11.00000 -1.20000 AFIX 0 C24 1 0.664895 0.168866 -0.020109 11.00000 0.03805 0.03513 = 0.06876 -0.00386 0.01677 0.00631 AFIX 43 H24 2 0.636241 0.140617 -0.060690 11.00000 -1.20000 AFIX 0 C25 1 0.662585 0.266980 0.015746 11.00000 0.02816 0.03391 = 0.03066 0.00566 0.00968 0.00855 C26 1 0.704313 0.307210 0.074641 11.00000 0.03104 0.05805 = 0.04165 -0.00851 0.00059 0.01194 AFIX 43 H26 2 0.703224 0.374187 0.099310 11.00000 -1.20000 AFIX 0 C27 1 0.747967 0.249231 0.097707 11.00000 0.02989 0.07985 = 0.04831 -0.00414 -0.00085 0.01563 AFIX 43 H27 2 0.776486 0.276814 0.139075 11.00000 -1.20000 AFIX 0 C28 1 0.614252 0.322479 -0.010207 11.00000 0.02724 0.02613 = 0.02208 0.00200 0.00701 0.00145 C29 1 0.572855 0.481551 -0.002714 11.00000 0.01695 0.02533 = 0.02010 0.00218 0.00374 0.00139 AFIX 13 H29 2 0.543730 0.434590 -0.006841 11.00000 -1.20000 AFIX 0 C30 1 0.565966 0.533231 -0.091684 11.00000 0.01816 0.02638 = 0.01989 -0.00102 0.00342 -0.00435 C31 1 0.574967 0.559500 0.069478 11.00000 0.01703 0.02542 = 0.01969 0.00150 0.00405 -0.00137 AFIX 13 H31 2 0.547083 0.610379 0.048803 11.00000 -1.20000 AFIX 0 C32 1 0.569737 0.507347 0.152588 11.00000 0.01672 0.02738 = 0.02193 0.00226 0.00586 0.00223 C33 1 0.623154 0.711799 0.119147 11.00000 0.02530 0.02664 = 0.02270 0.00099 0.00767 -0.00451 C34 1 0.675052 0.751873 0.147654 11.00000 0.02532 0.03210 = 0.02554 -0.00178 0.00714 -0.00662 C35 1 0.716181 0.687784 0.153995 11.00000 0.02846 0.03821 = 0.04781 -0.00413 0.00934 -0.00361 AFIX 43 H35 2 0.711477 0.616774 0.137166 11.00000 -1.20000 AFIX 0 C36 1 0.763912 0.727732 0.184855 11.00000 0.02443 0.04774 = 0.05552 -0.00234 0.01045 -0.00168 AFIX 43 H36 2 0.791668 0.683087 0.189687 11.00000 -1.20000 AFIX 0 C37 1 0.772168 0.831192 0.208847 11.00000 0.02904 0.05036 = 0.03091 0.00211 0.00654 -0.00967 C38 1 0.731044 0.894474 0.201341 11.00000 0.03753 0.03635 = 0.05167 -0.00827 0.00491 -0.01210 AFIX 43 H38 2 0.735890 0.965873 0.216789 11.00000 -1.20000 AFIX 0 C39 1 0.682737 0.855594 0.171616 11.00000 0.03046 0.03283 = 0.04594 -0.00559 0.00715 -0.00637 AFIX 43 H39 2 0.655043 0.900115 0.167747 11.00000 -1.20000 AFIX 0 C40 1 0.824429 0.872329 0.241696 11.00000 0.03077 0.06179 = 0.04426 0.00058 0.00419 -0.01423 AFIX 137 H40A 2 0.838378 0.883074 0.192168 11.00000 -1.50000 H40B 2 0.845014 0.822117 0.282429 11.00000 -1.50000 H40C 2 0.823972 0.938620 0.271910 11.00000 -1.50000 AFIX 0 O17 4 0.428696 0.881449 0.649577 11.00000 0.03712 0.06043 = 0.04648 0.01167 0.00754 0.01979 O18 4 0.488187 0.884043 0.583428 11.00000 0.04723 0.04379 = 0.03451 0.01105 0.01145 0.00804 AFIX 147 H18A 2 0.517483 0.861652 0.593075 11.00000 -1.50000 AFIX 0 N1 3 0.478102 0.724883 0.761297 11.00000 0.02642 0.02848 = 0.02465 -0.00006 0.00513 -0.00128 AFIX 137 H1D 2 0.462787 0.681093 0.717059 11.00000 -1.20000 H1E 2 0.454777 0.756066 0.783018 11.00000 -1.20000 H1F 2 0.499592 0.688096 0.804541 11.00000 -1.20000 AFIX 0 C41 1 0.470160 0.858508 0.649793 11.00000 0.03527 0.02869 = 0.02870 0.00252 0.00532 0.00423 C42 1 0.505966 0.805127 0.727628 11.00000 0.02740 0.02513 = 0.02734 0.00336 0.00574 0.00061 AFIX 13 H42 2 0.533925 0.772237 0.709201 11.00000 -1.20000 AFIX 0 C43 1 0.526354 0.887862 0.797315 11.00000 0.04048 0.02298 = 0.03803 -0.00188 0.00368 -0.00210 AFIX 23 H43A 2 0.539478 0.946085 0.769464 11.00000 -1.20000 H43B 2 0.498213 0.915366 0.817252 11.00000 -1.20000 AFIX 0 C44 1 0.567177 0.853358 0.877605 11.00000 0.04881 0.03524 = 0.03742 -0.00184 -0.00541 -0.00556 AFIX 13 H44 2 0.554614 0.790564 0.901994 11.00000 -1.20000 AFIX 0 C45 1 0.614472 0.822969 0.857122 11.00000 0.04235 0.14882 = 0.07768 -0.00135 -0.01157 0.01431 AFIX 137 H45A 2 0.607422 0.768495 0.812252 11.00000 -1.50000 H45B 2 0.638364 0.796727 0.910238 11.00000 -1.50000 H45C 2 0.628605 0.883784 0.835461 11.00000 -1.50000 AFIX 0 C46 1 0.575201 0.938840 0.946784 11.00000 0.10989 0.04924 = 0.05320 -0.01285 -0.02247 -0.00903 AFIX 137 H46A 2 0.585093 1.003289 0.923197 11.00000 -1.50000 H46B 2 0.601503 0.917607 0.998731 11.00000 -1.50000 H46C 2 0.544159 0.950490 0.962826 11.00000 -1.50000 AFIX 0 O19 4 0.423467 0.197053 0.284803 11.00000 0.02834 0.06728 = 0.06388 0.03082 0.01280 0.00201 O20 4 0.485717 0.118371 0.381853 11.00000 0.04112 0.05719 = 0.05403 0.03181 0.01164 0.00308 AFIX 147 H20 2 0.462640 0.092599 0.399659 11.00000 -1.50000 AFIX 0 N2 3 0.486214 0.322059 0.229452 11.00000 0.02586 0.02591 = 0.02512 0.00188 0.00805 0.00267 AFIX 137 H2A 2 0.460638 0.302531 0.182914 11.00000 -1.20000 H2B 2 0.510322 0.353546 0.209952 11.00000 -1.20000 H2C 2 0.474738 0.367259 0.263449 11.00000 -1.20000 AFIX 0 C47 1 0.466795 0.181836 0.316652 11.00000 0.03322 0.02980 = 0.03150 0.00450 0.00671 0.00067 C48 1 0.507233 0.229235 0.281485 11.00000 0.02519 0.02513 = 0.02929 0.00195 0.00614 0.00101 AFIX 13 H48 2 0.536065 0.250407 0.331485 11.00000 -1.20000 AFIX 0 C49 1 0.524484 0.148189 0.225743 11.00000 0.03352 0.02746 = 0.04408 -0.00452 0.01185 0.00089 AFIX 23 H49A 2 0.533387 0.083971 0.260983 11.00000 -1.20000 H49B 2 0.495860 0.131200 0.175025 11.00000 -1.20000 AFIX 0 C50 1 0.568219 0.177475 0.191367 11.00000 0.05552 0.03230 = 0.08103 -0.00916 0.04427 -0.00225 AFIX 13 H50 2 0.559276 0.242918 0.156548 11.00000 -1.20000 AFIX 0 C51 1 0.614126 0.197498 0.261869 11.00000 0.04297 0.19561 = 0.14964 -0.09010 0.04102 -0.02885 AFIX 137 H51A 2 0.609856 0.260508 0.293741 11.00000 -1.50000 H51B 2 0.642095 0.207064 0.236550 11.00000 -1.50000 H51C 2 0.620964 0.138240 0.302213 11.00000 -1.50000 AFIX 0 C52 1 0.576120 0.092670 0.129930 11.00000 0.09335 0.05425 = 0.09999 -0.01289 0.06772 0.00841 AFIX 137 H52A 2 0.587082 0.028711 0.163241 11.00000 -1.50000 H52B 2 0.601615 0.115019 0.102024 11.00000 -1.50000 H52C 2 0.544758 0.079601 0.084915 11.00000 -1.50000 AFIX 6 O21 4 0.575935 0.058859 0.529140 11.00000 0.04441 0.03731 = 0.03939 -0.00635 0.00478 0.00244 H21D 2 0.565482 0.011056 0.491612 11.00000 -1.50000 H21E 2 0.580174 0.111007 0.499137 11.00000 -1.50000 AFIX 0 HKLF 4 REM p20240501c_a.res in C2 REM wR2 = 0.1081, GooF = S = 1.050, Restrained GooF = 1.050 for all data REM R1 = 0.0385 for 11216 Fo > 4sig(Fo) and 0.0387 for all 11329 data REM 700 parameters refined using 3 restraints END WGHT 0.0651 3.0801 REM Instructions for potential hydrogen bonds EQIV $1 x, y, z+1 HTAB O6 O11_$1 HTAB O14 O3 HTAB O14 O4 HTAB O18 O8 EQIV $2 -x+1, y, -z+1 HTAB N1 O4_$2 HTAB N1 O16_$2 HTAB N1 O12_$1 HTAB C42 O8 HTAB O20 O21_$2 EQIV $3 -x+1, y, -z HTAB N2 O9_$3 HTAB N2 O13 HTAB N2 O5_$2 HTAB C48 O1 REM Highest difference peak 0.284, deepest hole -0.248, 1-sigma level 0.045 Q1 1 0.5404 0.6188 0.4339 11.00000 0.05 0.28 Q2 1 0.5401 0.4353 0.1875 11.00000 0.05 0.25 Q3 1 0.5833 0.5037 0.3024 11.00000 0.05 0.25 Q4 1 0.6984 0.7342 0.1233 11.00000 0.05 0.24 Q5 1 0.5777 0.2762 0.0024 11.00000 0.05 0.23 ; _shelx_res_checksum 38149 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.790 _oxdiff_exptl_absorpt_empirical_full_min 0.798 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.59040(7) 0.27360(14) 0.48399(12) 0.0336(4) Uani 1 1 d . . . . . O2 O 0.62210(5) 0.43110(13) 0.52978(10) 0.0237(3) Uani 1 1 d . . . . . O3 O 0.58745(7) 0.46818(14) 0.35912(11) 0.0309(4) Uani 1 1 d . . . . . O4 O 0.54613(6) 0.60753(14) 0.38704(10) 0.0298(4) Uani 1 1 d . . . . . O5 O 0.54053(7) 0.43980(14) 0.64709(11) 0.0311(4) Uani 1 1 d . . . . . O6 O 0.58582(7) 0.57338(14) 0.71806(10) 0.0289(4) Uani 1 1 d D . . . . H6 H 0.5836(15) 0.549(3) 0.7673(16) 0.059(12) Uiso 1 1 d D . . . . O7 O 0.61503(5) 0.62640(12) 0.57994(10) 0.0229(3) Uani 1 1 d . . . . . O8 O 0.57131(7) 0.76879(15) 0.59511(12) 0.0343(4) Uani 1 1 d . . . . . C1 C 0.83242(11) 0.1954(3) 0.5993(2) 0.0529(8) Uani 1 1 d . . . . . H1A H 0.853370 0.251352 0.587023 0.079 Uiso 1 1 calc R U . . . H1B H 0.835410 0.133818 0.564722 0.079 Uiso 1 1 calc R U . . . H1C H 0.843317 0.178025 0.661696 0.079 Uiso 1 1 calc R U . . . C2 C 0.77866(10) 0.2308(3) 0.57519(18) 0.0397(6) Uani 1 1 d . . . . . C3 C 0.74001(11) 0.1599(2) 0.5526(2) 0.0437(7) Uani 1 1 d . . . . . H3 H 0.747371 0.087865 0.551001 0.052 Uiso 1 1 calc R U . . . C4 C 0.69056(10) 0.1920(2) 0.5322(2) 0.0406(6) Uani 1 1 d . . . . . H4 H 0.664529 0.141951 0.516889 0.049 Uiso 1 1 calc R U . . . C5 C 0.67912(9) 0.2967(2) 0.53423(15) 0.0297(5) Uani 1 1 d . . . . . C6 C 0.71777(10) 0.3689(2) 0.55573(19) 0.0385(6) Uani 1 1 d . . . . . H6A H 0.710336 0.440962 0.556665 0.046 Uiso 1 1 calc R U . . . C7 C 0.76706(10) 0.3365(3) 0.5758(2) 0.0442(7) Uani 1 1 d . . . . . H7 H 0.793104 0.386533 0.590090 0.053 Uiso 1 1 calc R U . . . C8 C 0.62602(8) 0.32951(19) 0.51261(14) 0.0257(4) Uani 1 1 d . . . . . C9 C 0.57418(8) 0.48030(18) 0.49921(13) 0.0214(4) Uani 1 1 d . . . . . H9 H 0.547494 0.427436 0.496366 0.026 Uiso 1 1 calc R U . . . C10 C 0.56836(8) 0.52466(18) 0.40758(14) 0.0229(4) Uani 1 1 d . . . . . C11 C 0.57092(7) 0.56380(18) 0.56434(13) 0.0214(4) Uani 1 1 d . . . . . H11 H 0.541359 0.608680 0.537683 0.026 Uiso 1 1 calc R U . . . C12 C 0.56525(7) 0.51917(18) 0.64996(14) 0.0216(4) Uani 1 1 d . . . . . C13 C 0.61100(8) 0.72743(18) 0.59993(14) 0.0247(4) Uani 1 1 d . . . . . C14 C 0.66008(9) 0.77970(19) 0.62777(15) 0.0279(5) Uani 1 1 d . . . . . C15 C 0.70409(10) 0.7269(2) 0.63540(19) 0.0381(6) Uani 1 1 d . . . . . H15 H 0.703419 0.654461 0.623388 0.046 Uiso 1 1 calc R U . . . C16 C 0.74932(11) 0.7790(3) 0.6605(2) 0.0467(7) Uani 1 1 d . . . . . H16 H 0.779401 0.742341 0.664396 0.056 Uiso 1 1 calc R U . . . C17 C 0.75090(11) 0.8847(2) 0.68002(18) 0.0412(6) Uani 1 1 d . . . . . C18 C 0.70713(12) 0.9366(2) 0.6733(2) 0.0466(7) Uani 1 1 d . . . . . H18 H 0.707937 1.008658 0.686839 0.056 Uiso 1 1 calc R U . . . C19 C 0.66153(11) 0.8854(2) 0.6468(2) 0.0403(6) Uani 1 1 d . . . . . H19 H 0.631450 0.922574 0.641768 0.048 Uiso 1 1 calc R U . . . C20 C 0.80056(12) 0.9400(3) 0.7072(2) 0.0565(9) Uani 1 1 d . . . . . H20A H 0.822611 0.904454 0.757728 0.085 Uiso 1 1 calc R U . . . H20B H 0.795536 1.012100 0.722880 0.085 Uiso 1 1 calc R U . . . H20C H 0.815749 0.939338 0.658480 0.085 Uiso 1 1 calc R U . . . O9 O 0.57578(6) 0.28473(14) -0.05484(11) 0.0306(4) Uani 1 1 d . . . . . O10 O 0.61744(5) 0.41970(12) 0.02241(10) 0.0228(3) Uani 1 1 d . . . . . O11 O 0.58849(6) 0.49104(13) -0.14201(10) 0.0268(3) Uani 1 1 d . . . . . O12 O 0.53731(7) 0.60813(15) -0.10818(11) 0.0324(4) Uani 1 1 d . . . . . O13 O 0.54356(7) 0.42877(15) 0.14436(11) 0.0330(4) Uani 1 1 d . . . . . O14 O 0.59164(6) 0.55302(14) 0.22383(10) 0.0275(3) Uani 1 1 d D . . . . H14 H 0.591(2) 0.532(5) 0.275(2) 0.12(2) Uiso 1 1 d D . . . . O15 O 0.62159(5) 0.61459(13) 0.08602(10) 0.0239(3) Uani 1 1 d . . . . . O16 O 0.58661(6) 0.75892(13) 0.12433(11) 0.0295(3) Uani 1 1 d . . . . . C21 C 0.79889(15) 0.0904(4) 0.0853(3) 0.0705(12) Uani 1 1 d . . . . . H21A H 0.791367 0.016589 0.072737 0.106 Uiso 1 1 calc R U . . . H21B H 0.815732 0.099114 0.147726 0.106 Uiso 1 1 calc R U . . . H21C H 0.820655 0.115340 0.050675 0.106 Uiso 1 1 calc R U . . . C22 C 0.75087(12) 0.1523(3) 0.0618(2) 0.0495(8) Uani 1 1 d . . . . . C23 C 0.70856(13) 0.1127(3) 0.0031(3) 0.0566(9) Uani 1 1 d . . . . . H23 H 0.709691 0.045790 -0.021625 0.068 Uiso 1 1 calc R U . . . C24 C 0.66489(11) 0.1689(2) -0.0201(2) 0.0469(7) Uani 1 1 d . . . . . H24 H 0.636241 0.140617 -0.060690 0.056 Uiso 1 1 calc R U . . . C25 C 0.66258(9) 0.2670(2) 0.01575(16) 0.0306(5) Uani 1 1 d . . . . . C26 C 0.70431(10) 0.3072(3) 0.0746(2) 0.0455(7) Uani 1 1 d . . . . . H26 H 0.703224 0.374187 0.099310 0.055 Uiso 1 1 calc R U . . . C27 C 0.74797(11) 0.2492(3) 0.0977(2) 0.0550(9) Uani 1 1 d . . . . . H27 H 0.776486 0.276814 0.139075 0.066 Uiso 1 1 calc R U . . . C28 C 0.61425(8) 0.32248(18) -0.01021(14) 0.0251(4) Uani 1 1 d . . . . . C29 C 0.57285(8) 0.48155(17) -0.00271(13) 0.0211(4) Uani 1 1 d . . . . . H29 H 0.543730 0.434590 -0.006841 0.025 Uiso 1 1 calc R U . . . C30 C 0.56597(8) 0.53323(18) -0.09168(13) 0.0218(4) Uani 1 1 d . . . . . C31 C 0.57497(7) 0.55950(18) 0.06948(13) 0.0209(4) Uani 1 1 d . . . . . H31 H 0.547083 0.610379 0.048803 0.025 Uiso 1 1 calc R U . . . C32 C 0.56974(8) 0.50735(18) 0.15259(14) 0.0219(4) Uani 1 1 d . . . . . C33 C 0.62315(8) 0.71180(18) 0.11915(14) 0.0247(4) Uani 1 1 d . . . . . C34 C 0.67505(9) 0.7519(2) 0.14765(15) 0.0276(5) Uani 1 1 d . . . . . C35 C 0.71618(10) 0.6878(2) 0.15400(19) 0.0384(6) Uani 1 1 d . . . . . H35 H 0.711477 0.616774 0.137166 0.046 Uiso 1 1 calc R U . . . C36 C 0.76391(10) 0.7277(3) 0.1849(2) 0.0427(6) Uani 1 1 d . . . . . H36 H 0.791668 0.683087 0.189687 0.051 Uiso 1 1 calc R U . . . C37 C 0.77217(10) 0.8312(2) 0.20885(17) 0.0371(6) Uani 1 1 d . . . . . C38 C 0.73104(11) 0.8945(2) 0.2013(2) 0.0433(6) Uani 1 1 d . . . . . H38 H 0.735890 0.965873 0.216789 0.052 Uiso 1 1 calc R U . . . C39 C 0.68274(10) 0.8556(2) 0.17162(19) 0.0371(6) Uani 1 1 d . . . . . H39 H 0.655043 0.900115 0.167747 0.045 Uiso 1 1 calc R U . . . C40 C 0.82443(11) 0.8723(3) 0.2417(2) 0.0468(7) Uani 1 1 d . . . . . H40A H 0.838378 0.883074 0.192168 0.070 Uiso 1 1 calc R U . . . H40B H 0.845014 0.822117 0.282429 0.070 Uiso 1 1 calc R U . . . H40C H 0.823972 0.938620 0.271910 0.070 Uiso 1 1 calc R U . . . O17 O 0.42870(8) 0.8814(2) 0.64958(14) 0.0488(5) Uani 1 1 d . . . . . O18 O 0.48819(8) 0.88404(17) 0.58343(13) 0.0418(4) Uani 1 1 d . . . . . H18A H 0.517483 0.861652 0.593075 0.063 Uiso 1 1 calc R U . . . N1 N 0.47810(7) 0.72488(16) 0.76130(13) 0.0269(4) Uani 1 1 d . . . . . H1D H 0.462787 0.681093 0.717059 0.032 Uiso 1 1 calc R U . . . H1E H 0.454777 0.756066 0.783018 0.032 Uiso 1 1 calc R U . . . H1F H 0.499592 0.688096 0.804541 0.032 Uiso 1 1 calc R U . . . C41 C 0.47016(10) 0.8585(2) 0.64979(16) 0.0316(5) Uani 1 1 d . . . . . C42 C 0.50597(9) 0.80513(19) 0.72763(15) 0.0270(4) Uani 1 1 d . . . . . H42 H 0.533925 0.772237 0.709201 0.032 Uiso 1 1 calc R U . . . C43 C 0.52635(10) 0.8879(2) 0.79732(18) 0.0353(5) Uani 1 1 d . . . . . H43A H 0.539478 0.946085 0.769464 0.042 Uiso 1 1 calc R U . . . H43B H 0.498213 0.915366 0.817252 0.042 Uiso 1 1 calc R U . . . C44 C 0.56718(12) 0.8534(2) 0.87760(19) 0.0439(7) Uani 1 1 d . . . . . H44 H 0.554614 0.790564 0.901994 0.053 Uiso 1 1 calc R U . . . C45 C 0.61447(15) 0.8230(6) 0.8571(3) 0.0952(18) Uani 1 1 d . . . . . H45A H 0.607422 0.768495 0.812252 0.143 Uiso 1 1 calc R U . . . H45B H 0.638364 0.796727 0.910238 0.143 Uiso 1 1 calc R U . . . H45C H 0.628605 0.883784 0.835461 0.143 Uiso 1 1 calc R U . . . C46 C 0.5752(2) 0.9388(3) 0.9468(3) 0.0798(14) Uani 1 1 d . . . . . H46A H 0.585093 1.003289 0.923197 0.120 Uiso 1 1 calc R U . . . H46B H 0.601503 0.917607 0.998731 0.120 Uiso 1 1 calc R U . . . H46C H 0.544159 0.950490 0.962826 0.120 Uiso 1 1 calc R U . . . O19 O 0.42347(7) 0.1971(2) 0.28480(16) 0.0532(6) Uani 1 1 d . . . . . O20 O 0.48572(8) 0.1184(2) 0.38185(15) 0.0511(6) Uani 1 1 d . . . . . H20 H 0.462640 0.092599 0.399659 0.077 Uiso 1 1 calc R U . . . N2 N 0.48621(7) 0.32206(16) 0.22945(13) 0.0254(4) Uani 1 1 d . . . . . H2A H 0.460638 0.302531 0.182914 0.031 Uiso 1 1 calc R U . . . H2B H 0.510322 0.353546 0.209952 0.031 Uiso 1 1 calc R U . . . H2C H 0.474738 0.367259 0.263449 0.031 Uiso 1 1 calc R U . . . C47 C 0.46679(9) 0.1818(2) 0.31665(16) 0.0319(5) Uani 1 1 d . . . . . C48 C 0.50723(8) 0.22923(19) 0.28149(16) 0.0268(4) Uani 1 1 d . . . . . H48 H 0.536065 0.250407 0.331485 0.032 Uiso 1 1 calc R U . . . C49 C 0.52448(10) 0.1482(2) 0.22574(19) 0.0348(5) Uani 1 1 d . . . . . H49A H 0.533387 0.083971 0.260983 0.042 Uiso 1 1 calc R U . . . H49B H 0.495860 0.131200 0.175025 0.042 Uiso 1 1 calc R U . . . C50 C 0.56822(13) 0.1775(2) 0.1914(3) 0.0512(8) Uani 1 1 d . . . . . H50 H 0.559276 0.242918 0.156548 0.061 Uiso 1 1 calc R U . . . C51 C 0.61413(16) 0.1975(7) 0.2619(5) 0.127(3) Uani 1 1 d . . . . . H51A H 0.609856 0.260508 0.293741 0.190 Uiso 1 1 calc R U . . . H51B H 0.642095 0.207064 0.236550 0.190 Uiso 1 1 calc R U . . . H51C H 0.620964 0.138240 0.302213 0.190 Uiso 1 1 calc R U . . . C52 C 0.57612(19) 0.0927(3) 0.1299(3) 0.0743(13) Uani 1 1 d . . . . . H52A H 0.587082 0.028711 0.163241 0.112 Uiso 1 1 calc R U . . . H52B H 0.601615 0.115019 0.102024 0.112 Uiso 1 1 calc R U . . . H52C H 0.544758 0.079601 0.084915 0.112 Uiso 1 1 calc R U . . . O21 O 0.57594(8) 0.05886(17) 0.52914(13) 0.0417(4) Uani 1 1 d G . . . . H21D H 0.565482 0.011056 0.491612 0.063 Uiso 1 1 d G U . . . H21E H 0.580174 0.111007 0.499137 0.063 Uiso 1 1 d G U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0276(8) 0.0290(9) 0.0417(9) -0.0018(7) 0.0056(7) -0.0004(7) O2 0.0185(7) 0.0273(8) 0.0228(7) 0.0018(6) 0.0016(5) 0.0035(6) O3 0.0379(9) 0.0344(9) 0.0232(8) 0.0038(7) 0.0132(7) 0.0093(7) O4 0.0337(9) 0.0319(9) 0.0231(7) 0.0056(6) 0.0067(6) 0.0091(7) O5 0.0353(9) 0.0345(9) 0.0254(8) -0.0015(7) 0.0114(7) -0.0109(7) O6 0.0359(9) 0.0312(9) 0.0193(7) -0.0001(6) 0.0069(6) -0.0074(7) O7 0.0185(7) 0.0251(8) 0.0251(7) 0.0002(6) 0.0060(5) -0.0023(6) O8 0.0300(9) 0.0317(9) 0.0433(10) 0.0025(8) 0.0136(7) 0.0044(7) C1 0.0301(14) 0.075(2) 0.0547(18) 0.0138(17) 0.0130(13) 0.0186(14) C2 0.0282(12) 0.0571(17) 0.0339(13) 0.0077(12) 0.0086(10) 0.0124(12) C3 0.0370(14) 0.0402(15) 0.0552(17) 0.0105(13) 0.0153(13) 0.0146(12) C4 0.0292(13) 0.0394(15) 0.0523(16) 0.0053(13) 0.0099(11) 0.0070(11) C5 0.0250(11) 0.0375(13) 0.0252(10) 0.0031(9) 0.0048(8) 0.0081(9) C6 0.0271(12) 0.0425(15) 0.0449(15) -0.0040(12) 0.0080(10) 0.0030(11) C7 0.0261(12) 0.0550(17) 0.0488(16) -0.0041(14) 0.0062(11) 0.0024(12) C8 0.0260(11) 0.0283(11) 0.0219(10) 0.0010(8) 0.0053(8) 0.0044(9) C9 0.0164(9) 0.0272(11) 0.0197(9) 0.0018(8) 0.0035(7) 0.0013(8) C10 0.0176(9) 0.0300(11) 0.0200(9) 0.0002(8) 0.0033(7) -0.0023(8) C11 0.0153(9) 0.0277(11) 0.0205(9) 0.0026(8) 0.0037(7) -0.0007(8) C12 0.0169(9) 0.0270(10) 0.0208(9) 0.0010(8) 0.0052(7) 0.0001(8) C13 0.0253(11) 0.0256(11) 0.0235(10) 0.0029(8) 0.0075(8) -0.0016(8) C14 0.0279(11) 0.0288(12) 0.0278(11) 0.0018(9) 0.0090(9) -0.0049(9) C15 0.0292(12) 0.0356(13) 0.0480(15) -0.0074(12) 0.0081(11) -0.0030(11) C16 0.0276(13) 0.0510(17) 0.0592(18) -0.0106(15) 0.0083(12) -0.0033(12) C17 0.0378(14) 0.0462(16) 0.0388(14) -0.0048(12) 0.0092(11) -0.0153(12) C18 0.0497(16) 0.0343(14) 0.0569(18) -0.0049(13) 0.0165(14) -0.0132(13) C19 0.0392(14) 0.0292(13) 0.0541(16) -0.0031(12) 0.0157(12) -0.0024(11) C20 0.0436(17) 0.065(2) 0.0587(19) -0.0082(17) 0.0106(14) -0.0256(16) O9 0.0263(8) 0.0289(9) 0.0339(8) 0.0000(7) 0.0039(6) -0.0018(6) O10 0.0180(7) 0.0264(8) 0.0224(7) 0.0011(6) 0.0029(5) 0.0033(6) O11 0.0298(8) 0.0307(8) 0.0210(7) 0.0014(6) 0.0090(6) 0.0004(7) O12 0.0360(9) 0.0343(9) 0.0267(8) 0.0082(7) 0.0083(7) 0.0116(7) O13 0.0379(9) 0.0367(10) 0.0258(8) 0.0004(7) 0.0113(7) -0.0113(8) O14 0.0299(8) 0.0333(9) 0.0184(7) 0.0012(6) 0.0050(6) -0.0015(7) O15 0.0198(7) 0.0276(8) 0.0251(7) -0.0024(6) 0.0077(6) -0.0043(6) O16 0.0260(8) 0.0282(8) 0.0348(9) -0.0007(7) 0.0094(6) 0.0007(6) C21 0.052(2) 0.075(3) 0.087(3) 0.026(2) 0.0248(19) 0.038(2) C22 0.0413(16) 0.0564(19) 0.0550(18) 0.0173(15) 0.0205(14) 0.0215(14) C23 0.0482(18) 0.0397(16) 0.087(3) 0.0033(17) 0.0265(17) 0.0140(14) C24 0.0381(15) 0.0351(14) 0.069(2) -0.0039(14) 0.0168(14) 0.0063(12) C25 0.0282(11) 0.0339(12) 0.0307(11) 0.0057(10) 0.0097(9) 0.0085(10) C26 0.0310(13) 0.0580(19) 0.0417(14) -0.0085(13) 0.0006(11) 0.0119(13) C27 0.0299(14) 0.080(3) 0.0483(17) -0.0041(17) -0.0009(12) 0.0156(15) C28 0.0272(11) 0.0261(11) 0.0221(10) 0.0020(8) 0.0070(8) 0.0015(9) C29 0.0170(9) 0.0253(10) 0.0201(9) 0.0022(8) 0.0037(7) 0.0014(8) C30 0.0182(9) 0.0264(10) 0.0199(9) -0.0010(8) 0.0034(7) -0.0044(8) C31 0.0170(9) 0.0254(10) 0.0197(9) 0.0015(8) 0.0040(7) -0.0014(8) C32 0.0167(9) 0.0274(11) 0.0219(10) 0.0023(8) 0.0059(7) 0.0022(8) C33 0.0253(10) 0.0266(11) 0.0227(10) 0.0010(8) 0.0077(8) -0.0045(8) C34 0.0253(11) 0.0321(12) 0.0255(10) -0.0018(9) 0.0071(8) -0.0066(9) C35 0.0285(12) 0.0382(14) 0.0478(15) -0.0041(12) 0.0093(11) -0.0036(11) C36 0.0244(12) 0.0477(16) 0.0555(17) -0.0023(14) 0.0104(11) -0.0017(11) C37 0.0290(12) 0.0504(16) 0.0309(12) 0.0021(11) 0.0065(9) -0.0097(11) C38 0.0375(14) 0.0363(15) 0.0517(16) -0.0083(12) 0.0049(12) -0.0121(12) C39 0.0305(12) 0.0328(13) 0.0459(14) -0.0056(11) 0.0072(11) -0.0064(10) C40 0.0308(13) 0.0618(19) 0.0443(15) 0.0006(14) 0.0042(11) -0.0142(13) O17 0.0371(10) 0.0604(14) 0.0465(11) 0.0117(10) 0.0075(8) 0.0198(10) O18 0.0472(11) 0.0438(11) 0.0345(9) 0.0111(8) 0.0114(8) 0.0080(9) N1 0.0264(9) 0.0285(10) 0.0246(9) -0.0001(7) 0.0051(7) -0.0013(8) C41 0.0353(12) 0.0287(12) 0.0287(11) 0.0025(9) 0.0053(9) 0.0042(9) C42 0.0274(10) 0.0251(11) 0.0273(10) 0.0034(9) 0.0057(8) 0.0006(9) C43 0.0405(13) 0.0230(11) 0.0380(13) -0.0019(10) 0.0037(10) -0.0021(10) C44 0.0488(16) 0.0352(14) 0.0374(14) -0.0018(11) -0.0054(12) -0.0056(12) C45 0.042(2) 0.149(5) 0.078(3) -0.001(3) -0.0116(19) 0.014(3) C46 0.110(4) 0.049(2) 0.053(2) -0.0128(17) -0.022(2) -0.009(2) O19 0.0283(9) 0.0673(15) 0.0639(14) 0.0308(12) 0.0128(9) 0.0020(10) O20 0.0411(11) 0.0572(14) 0.0540(12) 0.0318(11) 0.0116(9) 0.0031(10) N2 0.0259(9) 0.0259(10) 0.0251(8) 0.0019(7) 0.0080(7) 0.0027(7) C47 0.0332(12) 0.0298(12) 0.0315(12) 0.0045(10) 0.0067(9) 0.0007(10) C48 0.0252(10) 0.0251(11) 0.0293(11) 0.0020(9) 0.0061(8) 0.0010(9) C49 0.0335(12) 0.0275(12) 0.0441(14) -0.0045(10) 0.0118(11) 0.0009(10) C50 0.0555(18) 0.0323(14) 0.081(2) -0.0092(15) 0.0443(18) -0.0023(13) C51 0.043(2) 0.196(8) 0.150(5) -0.090(6) 0.041(3) -0.029(3) C52 0.093(3) 0.054(2) 0.100(3) -0.013(2) 0.068(3) 0.008(2) O21 0.0444(11) 0.0373(10) 0.0394(10) -0.0063(8) 0.0048(8) 0.0024(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 C9 118.62(17) . . ? C12 O6 H6 116(3) . . ? C13 O7 C11 117.22(17) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C3 C2 C1 121.0(3) . . ? C3 C2 C7 118.5(2) . . ? C7 C2 C1 120.4(3) . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.2(3) . . ? C4 C3 H3 119.4 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 C8 119.4(2) . . ? C6 C5 C8 121.5(2) . . ? C5 C6 H6A 119.7 . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6A 119.7 . . ? C2 C7 H7 119.8 . . ? C6 C7 C2 120.5(3) . . ? C6 C7 H7 119.8 . . ? O1 C8 O2 123.3(2) . . ? O1 C8 C5 125.6(2) . . ? O2 C8 C5 111.1(2) . . ? O2 C9 H9 109.2 . . ? O2 C9 C10 109.26(17) . . ? O2 C9 C11 107.90(17) . . ? C10 C9 H9 109.2 . . ? C11 C9 H9 109.2 . . ? C11 C9 C10 112.14(18) . . ? O3 C10 C9 114.2(2) . . ? O4 C10 O3 126.6(2) . . ? O4 C10 C9 119.2(2) . . ? O7 C11 C9 107.79(17) . . ? O7 C11 H11 108.5 . . ? O7 C11 C12 110.65(16) . . ? C9 C11 H11 108.5 . . ? C9 C11 C12 112.65(19) . . ? C12 C11 H11 108.5 . . ? O5 C12 O6 126.9(2) . . ? O5 C12 C11 118.43(19) . . ? O6 C12 C11 114.62(19) . . ? O7 C13 C14 112.14(19) . . ? O8 C13 O7 122.8(2) . . ? O8 C13 C14 125.1(2) . . ? C15 C14 C13 122.1(2) . . ? C15 C14 C19 119.3(2) . . ? C19 C14 C13 118.5(2) . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.4(3) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.8 . . ? C15 C16 C17 120.4(3) . . ? C17 C16 H16 119.8 . . ? C16 C17 C20 119.6(3) . . ? C18 C17 C16 119.0(3) . . ? C18 C17 C20 121.4(3) . . ? C17 C18 H18 119.5 . . ? C17 C18 C19 121.0(3) . . ? C19 C18 H18 119.5 . . ? C14 C19 C18 119.8(3) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C28 O10 C29 116.51(16) . . ? C32 O14 H14 125(5) . . ? C33 O15 C31 117.11(17) . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? C23 C22 C21 120.3(3) . . ? C27 C22 C21 121.4(4) . . ? C27 C22 C23 118.3(3) . . ? C22 C23 H23 119.5 . . ? C24 C23 C22 121.0(3) . . ? C24 C23 H23 119.5 . . ? C23 C24 H24 119.9 . . ? C23 C24 C25 120.2(3) . . ? C25 C24 H24 119.9 . . ? C24 C25 C28 117.6(2) . . ? C26 C25 C24 119.5(3) . . ? C26 C25 C28 122.9(2) . . ? C25 C26 H26 120.2 . . ? C25 C26 C27 119.6(3) . . ? C27 C26 H26 120.2 . . ? C22 C27 C26 121.5(3) . . ? C22 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? O9 C28 O10 123.4(2) . . ? O9 C28 C25 124.2(2) . . ? O10 C28 C25 112.44(19) . . ? O10 C29 H29 108.1 . . ? O10 C29 C30 112.08(17) . . ? O10 C29 C31 107.84(16) . . ? C30 C29 H29 108.1 . . ? C31 C29 H29 108.1 . . ? C31 C29 C30 112.56(18) . . ? O11 C30 C29 116.20(19) . . ? O12 C30 O11 127.3(2) . . ? O12 C30 C29 116.44(19) . . ? O15 C31 C29 107.93(16) . . ? O15 C31 H31 108.7 . . ? O15 C31 C32 110.86(16) . . ? C29 C31 H31 108.7 . . ? C29 C31 C32 111.94(19) . . ? C32 C31 H31 108.7 . . ? O13 C32 O14 126.7(2) . . ? O13 C32 C31 117.68(19) . . ? O14 C32 C31 115.56(19) . . ? O15 C33 C34 111.29(19) . . ? O16 C33 O15 123.6(2) . . ? O16 C33 C34 125.1(2) . . ? C35 C34 C33 122.1(2) . . ? C39 C34 C33 118.7(2) . . ? C39 C34 C35 119.1(2) . . ? C34 C35 H35 120.0 . . ? C36 C35 C34 119.9(3) . . ? C36 C35 H35 120.0 . . ? C35 C36 H36 119.2 . . ? C35 C36 C37 121.6(3) . . ? C37 C36 H36 119.2 . . ? C36 C37 C40 120.3(3) . . ? C38 C37 C36 118.0(2) . . ? C38 C37 C40 121.7(3) . . ? C37 C38 H38 119.3 . . ? C37 C38 C39 121.3(3) . . ? C39 C38 H38 119.3 . . ? C34 C39 C38 120.0(3) . . ? C34 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40B 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C41 O18 H18A 109.5 . . ? H1D N1 H1E 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C42 N1 H1D 109.5 . . ? C42 N1 H1E 109.5 . . ? C42 N1 H1F 109.5 . . ? O17 C41 O18 121.1(2) . . ? O17 C41 C42 122.1(2) . . ? O18 C41 C42 116.7(2) . . ? N1 C42 C41 108.42(19) . . ? N1 C42 H42 110.0 . . ? N1 C42 C43 110.5(2) . . ? C41 C42 H42 110.0 . . ? C41 C42 C43 107.8(2) . . ? C43 C42 H42 110.0 . . ? C42 C43 H43A 108.1 . . ? C42 C43 H43B 108.1 . . ? H43A C43 H43B 107.3 . . ? C44 C43 C42 116.6(2) . . ? C44 C43 H43A 108.1 . . ? C44 C43 H43B 108.1 . . ? C43 C44 H44 107.4 . . ? C43 C44 C46 108.7(3) . . ? C45 C44 C43 113.2(3) . . ? C45 C44 H44 107.4 . . ? C45 C44 C46 112.5(4) . . ? C46 C44 H44 107.4 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45B 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46B 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C47 O20 H20 109.5 . . ? H2A N2 H2B 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C48 N2 H2A 109.5 . . ? C48 N2 H2B 109.5 . . ? C48 N2 H2C 109.5 . . ? O19 C47 O20 125.3(2) . . ? O19 C47 C48 123.2(2) . . ? O20 C47 C48 111.3(2) . . ? N2 C48 C47 108.03(19) . . ? N2 C48 H48 109.5 . . ? N2 C48 C49 111.4(2) . . ? C47 C48 H48 109.5 . . ? C47 C48 C49 109.0(2) . . ? C49 C48 H48 109.5 . . ? C48 C49 H49A 108.1 . . ? C48 C49 H49B 108.1 . . ? H49A C49 H49B 107.3 . . ? C50 C49 C48 117.0(2) . . ? C50 C49 H49A 108.1 . . ? C50 C49 H49B 108.1 . . ? C49 C50 H50 107.8 . . ? C49 C50 C52 109.1(3) . . ? C51 C50 C49 112.7(4) . . ? C51 C50 H50 107.8 . . ? C51 C50 C52 111.4(4) . . ? C52 C50 H50 107.8 . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51B 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C50 C52 H52A 109.5 . . ? C50 C52 H52B 109.5 . . ? C50 C52 H52C 109.5 . . ? H52A C52 H52B 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? H21D O21 H21E 104.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.209(3) . ? O2 C8 1.345(3) . ? O2 C9 1.437(2) . ? O3 C10 1.277(3) . ? O4 C10 1.231(3) . ? O5 C12 1.225(3) . ? O6 H6 0.861(14) . ? O6 C12 1.282(3) . ? O7 C11 1.434(2) . ? O7 C13 1.349(3) . ? O8 C13 1.212(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.512(4) . ? C2 C3 1.382(5) . ? C2 C7 1.397(5) . ? C3 H3 0.9500 . ? C3 C4 1.390(4) . ? C4 H4 0.9500 . ? C4 C5 1.386(4) . ? C5 C6 1.392(4) . ? C5 C8 1.487(3) . ? C6 H6A 0.9500 . ? C6 C7 1.388(4) . ? C7 H7 0.9500 . ? C9 H9 1.0000 . ? C9 C10 1.531(3) . ? C9 C11 1.512(3) . ? C11 H11 1.0000 . ? C11 C12 1.525(3) . ? C13 C14 1.479(3) . ? C14 C15 1.379(4) . ? C14 C19 1.390(4) . ? C15 H15 0.9500 . ? C15 C16 1.387(4) . ? C16 H16 0.9500 . ? C16 C17 1.391(5) . ? C17 C18 1.370(5) . ? C17 C20 1.511(4) . ? C18 H18 0.9500 . ? C18 C19 1.390(4) . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O9 C28 1.213(3) . ? O10 C28 1.346(3) . ? O10 C29 1.437(2) . ? O11 C30 1.268(3) . ? O12 C30 1.233(3) . ? O13 C32 1.232(3) . ? O14 H14 0.858(14) . ? O14 C32 1.272(3) . ? O15 C31 1.440(2) . ? O15 C33 1.352(3) . ? O16 C33 1.209(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 C22 1.514(4) . ? C22 C23 1.384(5) . ? C22 C27 1.382(5) . ? C23 H23 0.9500 . ? C23 C24 1.376(4) . ? C24 H24 0.9500 . ? C24 C25 1.393(4) . ? C25 C26 1.378(4) . ? C25 C28 1.480(3) . ? C26 H26 0.9500 . ? C26 C27 1.388(4) . ? C27 H27 0.9500 . ? C29 H29 1.0000 . ? C29 C30 1.526(3) . ? C29 C31 1.512(3) . ? C31 H31 1.0000 . ? C31 C32 1.524(3) . ? C33 C34 1.485(3) . ? C34 C35 1.394(4) . ? C34 C39 1.387(4) . ? C35 H35 0.9500 . ? C35 C36 1.385(4) . ? C36 H36 0.9500 . ? C36 C37 1.385(4) . ? C37 C38 1.385(4) . ? C37 C40 1.503(4) . ? C38 H38 0.9500 . ? C38 C39 1.392(4) . ? C39 H39 0.9500 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? O17 C41 1.193(3) . ? O18 H18A 0.8400 . ? O18 C41 1.330(3) . ? N1 H1D 0.9100 . ? N1 H1E 0.9100 . ? N1 H1F 0.9100 . ? N1 C42 1.478(3) . ? C41 C42 1.522(3) . ? C42 H42 1.0000 . ? C42 C43 1.528(3) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C43 C44 1.523(4) . ? C44 H44 1.0000 . ? C44 C45 1.496(6) . ? C44 C46 1.527(5) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? O19 C47 1.191(3) . ? O20 H20 0.8400 . ? O20 C47 1.310(3) . ? N2 H2A 0.9100 . ? N2 H2B 0.9100 . ? N2 H2C 0.9100 . ? N2 C48 1.478(3) . ? C47 C48 1.519(3) . ? C48 H48 1.0000 . ? C48 C49 1.529(3) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C49 C50 1.516(4) . ? C50 H50 1.0000 . ? C50 C51 1.473(7) . ? C50 C52 1.520(5) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? O21 H21D 0.8500 . ? O21 H21E 0.8498 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C9 C10 O3 37.2(3) . . . . ? O2 C9 C10 O4 -143.6(2) . . . . ? O2 C9 C11 O7 50.2(2) . . . . ? O2 C9 C11 C12 -72.1(2) . . . . ? O7 C11 C12 O5 -156.29(19) . . . . ? O7 C11 C12 O6 26.6(3) . . . . ? O7 C13 C14 C15 -2.8(3) . . . . ? O7 C13 C14 C19 177.3(2) . . . . ? O8 C13 C14 C15 177.2(2) . . . . ? O8 C13 C14 C19 -2.8(4) . . . . ? C1 C2 C3 C4 178.6(3) . . . . ? C1 C2 C7 C6 -178.5(3) . . . . ? C2 C3 C4 C5 0.0(5) . . . . ? C3 C2 C7 C6 1.2(5) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C3 C4 C5 C8 -179.7(2) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? C4 C5 C8 O1 -8.2(4) . . . . ? C4 C5 C8 O2 171.3(2) . . . . ? C5 C6 C7 C2 -0.3(4) . . . . ? C6 C5 C8 O1 171.2(3) . . . . ? C6 C5 C8 O2 -9.3(3) . . . . ? C7 C2 C3 C4 -1.0(5) . . . . ? C8 O2 C9 C10 -90.3(2) . . . . ? C8 O2 C9 C11 147.58(19) . . . . ? C8 C5 C6 C7 179.9(3) . . . . ? C9 O2 C8 O1 -11.0(3) . . . . ? C9 O2 C8 C5 169.56(17) . . . . ? C9 C11 C12 O5 -35.5(3) . . . . ? C9 C11 C12 O6 147.34(19) . . . . ? C10 C9 C11 O7 -70.2(2) . . . . ? C10 C9 C11 C12 167.48(16) . . . . ? C11 O7 C13 O8 -8.8(3) . . . . ? C11 O7 C13 C14 171.20(17) . . . . ? C11 C9 C10 O3 156.79(19) . . . . ? C11 C9 C10 O4 -24.1(3) . . . . ? C13 O7 C11 C9 149.54(18) . . . . ? C13 O7 C11 C12 -86.9(2) . . . . ? C13 C14 C15 C16 179.1(3) . . . . ? C13 C14 C19 C18 179.9(3) . . . . ? C14 C15 C16 C17 1.3(5) . . . . ? C15 C14 C19 C18 0.0(4) . . . . ? C15 C16 C17 C18 -0.6(5) . . . . ? C15 C16 C17 C20 -179.9(3) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C17 C18 C19 C14 0.7(5) . . . . ? C19 C14 C15 C16 -1.0(4) . . . . ? C20 C17 C18 C19 178.9(3) . . . . ? O10 C29 C30 O11 22.3(3) . . . . ? O10 C29 C30 O12 -161.08(19) . . . . ? O10 C29 C31 O15 53.2(2) . . . . ? O10 C29 C31 C32 -69.1(2) . . . . ? O15 C31 C32 O13 -152.83(19) . . . . ? O15 C31 C32 O14 30.0(3) . . . . ? O15 C33 C34 C35 -11.4(3) . . . . ? O15 C33 C34 C39 170.9(2) . . . . ? O16 C33 C34 C35 168.7(2) . . . . ? O16 C33 C34 C39 -9.0(4) . . . . ? C21 C22 C23 C24 -178.8(4) . . . . ? C21 C22 C27 C26 178.4(3) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C23 C22 C27 C26 -1.3(5) . . . . ? C23 C24 C25 C26 -0.1(5) . . . . ? C23 C24 C25 C28 -178.6(3) . . . . ? C24 C25 C26 C27 -0.3(5) . . . . ? C24 C25 C28 O9 6.2(4) . . . . ? C24 C25 C28 O10 -174.7(2) . . . . ? C25 C26 C27 C22 1.0(5) . . . . ? C26 C25 C28 O9 -172.2(3) . . . . ? C26 C25 C28 O10 6.8(3) . . . . ? C27 C22 C23 C24 0.9(5) . . . . ? C28 O10 C29 C30 -83.2(2) . . . . ? C28 O10 C29 C31 152.41(18) . . . . ? C28 C25 C26 C27 178.1(3) . . . . ? C29 O10 C28 O9 -3.8(3) . . . . ? C29 O10 C28 C25 177.13(18) . . . . ? C29 C31 C32 O13 -32.2(3) . . . . ? C29 C31 C32 O14 150.53(19) . . . . ? C30 C29 C31 O15 -70.9(2) . . . . ? C30 C29 C31 C32 166.79(16) . . . . ? C31 O15 C33 O16 -10.2(3) . . . . ? C31 O15 C33 C34 169.84(17) . . . . ? C31 C29 C30 O11 144.05(19) . . . . ? C31 C29 C30 O12 -39.3(3) . . . . ? C33 O15 C31 C29 153.50(18) . . . . ? C33 O15 C31 C32 -83.6(2) . . . . ? C33 C34 C35 C36 -176.9(2) . . . . ? C33 C34 C39 C38 177.9(3) . . . . ? C34 C35 C36 C37 -0.9(5) . . . . ? C35 C34 C39 C38 0.1(4) . . . . ? C35 C36 C37 C38 0.1(4) . . . . ? C35 C36 C37 C40 -179.7(3) . . . . ? C36 C37 C38 C39 0.7(4) . . . . ? C37 C38 C39 C34 -0.9(5) . . . . ? C39 C34 C35 C36 0.7(4) . . . . ? C40 C37 C38 C39 -179.4(3) . . . . ? O17 C41 C42 N1 41.5(3) . . . . ? O17 C41 C42 C43 -78.1(3) . . . . ? O18 C41 C42 N1 -142.2(2) . . . . ? O18 C41 C42 C43 98.1(3) . . . . ? N1 C42 C43 C44 67.8(3) . . . . ? C41 C42 C43 C44 -173.9(2) . . . . ? C42 C43 C44 C45 65.4(4) . . . . ? C42 C43 C44 C46 -168.8(3) . . . . ? O19 C47 C48 N2 21.6(4) . . . . ? O19 C47 C48 C49 -99.6(3) . . . . ? O20 C47 C48 N2 -162.3(2) . . . . ? O20 C47 C48 C49 76.5(3) . . . . ? N2 C48 C49 C50 66.3(3) . . . . ? C47 C48 C49 C50 -174.6(3) . . . . ? C48 C49 C50 C51 61.8(5) . . . . ? C48 C49 C50 C52 -173.9(3) . . . . ?