#------------------------------------------------------------------------------ #$Date: 2019-12-13 03:36:47 +0200 (Fri, 13 Dec 2019) $ #$Revision: 245031 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125645.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_7125645 loop_ _publ_author_name 'Cho, Jihee' 'Verwilst, Peter' 'Kang, Minjung' 'Pan, Jia-Lin' 'Sharma, Amit' 'Hong, Chang Seop' 'Kim, Jong Seung' 'Kim, Sanghee' _publ_section_title ; Crown ether-appended calix[2]triazolium[2]arene as a macrocyclic receptor for the recognition of H2PO4− anion ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC08906C _journal_year 2019 _chemical_formula_moiety 'C38 H52 N6 O6' _chemical_formula_sum 'C38 H52 N6 O6' _chemical_formula_weight 688.85 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-05-30 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497) ; _audit_update_record ; 2019-05-17 deposited with the CCDC. 2019-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.284(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4036(2) _cell_length_b 19.8880(4) _cell_length_c 18.5228(4) _cell_measurement_reflns_used 13444 _cell_measurement_temperature 292(3) _cell_measurement_theta_max 73.6520 _cell_measurement_theta_min 2.2060 _cell_volume 3729.95(13) _computing_cell_refinement 'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 292(3) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2262 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.984 _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 -65.00 33.00 1.00 1.03 -- -41.24 38.00 -30.00 98 2 \w 80.00 116.00 1.00 1.03 -- 41.24 38.00 150.00 36 3 \w 20.00 117.00 1.00 1.03 -- 41.24 77.00 -60.00 97 4 \w 2.00 80.00 1.00 1.03 -- 41.24 -99.00 150.00 78 5 \w 9.00 43.00 1.00 1.03 -- 41.24 77.00 -90.00 34 6 \w 45.00 89.00 1.00 1.03 -- 41.24-125.00 -30.00 44 7 \w 79.00 117.00 1.00 1.03 -- 41.24 77.00 -90.00 38 8 \w 101.00 176.00 1.00 4.11 -- 106.19 79.00-132.00 75 9 \w 80.00 178.00 1.00 4.11 -- 106.19 30.00 30.00 98 10 \w 34.00 138.00 1.00 4.11 -- 106.19 -77.00 60.00 104 11 \w 77.00 117.00 1.00 4.11 -- 106.19 -61.00-120.00 40 12 \w 33.00 131.00 1.00 4.11 -- 106.19 -45.00 90.00 98 13 \w 64.00 91.00 1.00 4.11 -- 106.19 -94.00-180.00 27 14 \w 124.00 172.00 1.00 4.11 -- 106.19 125.00 0.00 48 15 \w 115.00 148.00 1.00 4.11 -- 106.19 125.00 30.00 33 16 \w 80.00 112.00 1.00 4.11 -- 106.19 61.00 -30.00 32 17 \w 48.00 121.00 1.00 4.11 -- 106.19-125.00 60.00 73 18 \w 78.00 178.00 1.00 4.11 -- 106.19 61.00-180.00 100 19 \w 29.00 138.00 1.00 4.11 -- 106.19 0.00 30.00 109 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0793376000 _diffrn_orient_matrix_UB_12 -0.0640492000 _diffrn_orient_matrix_UB_13 -0.0281009000 _diffrn_orient_matrix_UB_21 0.0078177000 _diffrn_orient_matrix_UB_22 0.0170250000 _diffrn_orient_matrix_UB_23 -0.0800152000 _diffrn_orient_matrix_UB_31 0.1295130000 _diffrn_orient_matrix_UB_32 -0.0401350000 _diffrn_orient_matrix_UB_33 0.0106596000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0216 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 28406 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.921 _diffrn_reflns_theta_min 3.309 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.677 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.201 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic light colourless' _exptl_crystal_density_diffrn 1.227 _exptl_crystal_description irregular _exptl_crystal_F_000 1480 _exptl_crystal_size_max 0.685 _exptl_crystal_size_mid 0.462 _exptl_crystal_size_min 0.344 _refine_diff_density_max 0.638 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 485 _refine_ls_number_reflns 7434 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0643 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1119P)^2^+1.2650P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1902 _refine_ls_wR_factor_ref 0.1986 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6383 _reflns_number_total 7434 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08906c2.cif _cod_data_source_block exp_1255 _cod_database_code 7125645 _shelx_shelxl_version_number 2017/1 _chemical_oxdiff_formula 'c36 H52 N6 O6' _chemical_oxdiff_usercomment CJH-10-118 _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 0.801 _shelx_estimated_absorpt_t_min 0.654 _reflns_odcompleteness_completeness 99.99 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Sof(O30A)=Sof(C28B)=Sof(H28C)=Sof(H28D)=Sof(H31C)=Sof(H31D)=Sof(C9B)= Sof(H9BA)=Sof(H9BB)=1-FVAR(1) Sof(O30B)=Sof(C28A)=Sof(H28A)=Sof(H28B)=Sof(H31A)=Sof(H31B)=Sof(C9A)= Sof(H9AA)=Sof(H9AB)=FVAR(1) 3.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C41(H41A,H41B), C2(H2A,H2B), C12(H12A,H12B), C40(H40A,H40B), C16(H16A,H16B), C38(H38A,H38B), C34(H34A,H34B), C32(H32A,H32B), C37(H37A,H37B), C35(H35A,H35B), C28A(H28A,H28B), C28B(H28C,H28D), C31(H31A,H31B), C31(H31C, H31D), C9A(H9AA,H9AB), C9B(H9BA,H9BB) 3.b Aromatic/amide H refined with riding coordinates: C10(H10), C6(H6), C26(H26), C4(H4), C24(H24), C18(H18) 3.c Idealised Me refined as rotating group: C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C45(H45A,H45B,H45C), C50(H50A,H50B, H50C), C46(H46A,H46B,H46C), C29(H29A,H29B,H29C) ; _shelx_res_file ; TITL exp_1255_a.res in P2(1)/n exp_1255.res created by SHELXL-2017/1 at 13:27:20 on 30-May-2018 REM Old TITL exp_1255 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.201, Rweak 0.013, Alpha 0.035, Orientation as input REM Formula found by SHELXT: C42 C4 C48 CELL 1.54184 10.4036 19.888 18.5228 90 103.284 90 ZERR 4 0.0002 0.0004 0.0004 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 152 208 24 24 L.S. 4 PLAN 20 SIZE 0.344 0.462 0.685 TEMP 19(3) BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.111900 1.265000 FVAR 3.03335 0.45679 O42 4 0.752576 0.424359 0.469805 11.00000 0.04461 0.05035 = 0.05063 -0.00397 0.01953 -0.00621 O27 4 0.596144 0.271405 0.557899 11.00000 0.04516 0.08038 = 0.05277 -0.01004 0.01862 -0.01036 O39 4 0.991935 0.426474 0.583942 11.00000 0.06252 0.06956 = 0.04838 0.00482 0.01887 0.01602 N9 3 0.916902 0.290742 0.441620 11.00000 0.03170 0.05648 = 0.05563 -0.00290 0.01350 0.00286 N22 3 0.967592 0.234215 0.420540 11.00000 0.04648 0.05806 = 0.07131 0.00132 0.02680 0.00827 N21 3 0.911071 0.182904 0.445534 11.00000 0.05042 0.05576 = 0.07751 0.00200 0.02718 0.00901 O33 4 1.081391 0.263777 0.738113 11.00000 0.07928 0.10109 = 0.05809 0.01217 0.00890 0.01261 C11 1 0.823673 0.207212 0.483059 11.00000 0.02971 0.05082 = 0.04866 0.00479 0.01072 0.00402 N17 3 0.352763 0.353038 0.445546 11.00000 0.03841 0.06609 = 0.07886 -0.00234 0.02592 0.00744 C23 1 0.745430 0.425805 0.393850 11.00000 0.03705 0.04419 = 0.05127 -0.00239 0.01809 -0.00342 C1 1 0.440179 0.434261 0.395552 11.00000 0.03467 0.05500 = 0.06055 0.00020 0.02104 0.01122 C7 1 0.843655 0.393213 0.366761 11.00000 0.03448 0.04685 = 0.05639 -0.00282 0.01836 -0.00344 C3 1 0.638917 0.455723 0.345727 11.00000 0.04017 0.04576 = 0.05927 0.00149 0.02046 0.00194 C14 1 0.528003 0.223797 0.509201 11.00000 0.03907 0.05758 = 0.04808 0.00263 0.01759 -0.00567 C10 1 0.827703 0.275127 0.481596 11.00000 0.04246 0.05477 = 0.06255 -0.00264 0.02575 0.00074 AFIX 43 H10 2 0.779155 0.304877 0.503550 11.00000 -1.20000 AFIX 0 C13 1 0.595138 0.168794 0.489342 11.00000 0.03936 0.05681 = 0.05381 0.01200 0.01821 0.00096 N20 3 0.318417 0.422520 0.353707 11.00000 0.04122 0.08777 = 0.08394 0.01020 0.01461 0.00815 C15 1 0.393601 0.233093 0.477827 11.00000 0.03622 0.05947 = 0.05437 0.00493 0.02135 -0.00252 C6 1 0.834755 0.393922 0.290511 11.00000 0.04334 0.05354 = 0.05957 -0.00436 0.02509 -0.00242 AFIX 43 H6 2 0.900756 0.372967 0.272327 11.00000 -1.20000 AFIX 0 C8 1 0.955714 0.357436 0.418783 11.00000 0.02972 0.05525 = 0.06233 -0.00235 0.01698 -0.00269 AFIX 23 H8A 2 1.028406 0.352038 0.394552 11.00000 -1.20000 H8B 2 0.986566 0.384944 0.462585 11.00000 -1.20000 AFIX 0 N19 3 0.264989 0.373037 0.384075 11.00000 0.03815 0.09238 = 0.08966 0.00901 0.01489 0.00231 C26 1 0.325385 0.183746 0.431593 11.00000 0.03647 0.06723 = 0.05465 0.00672 0.01564 -0.00681 AFIX 43 H26 2 0.235410 0.189396 0.411916 11.00000 -1.20000 AFIX 0 C41 1 0.808827 0.482938 0.510730 11.00000 0.05100 0.04762 = 0.05783 -0.00640 0.01316 0.00391 AFIX 23 H41A 2 0.739839 0.515277 0.512529 11.00000 -1.20000 H41B 2 0.871761 0.503936 0.486439 11.00000 -1.20000 AFIX 0 C4 1 0.633267 0.454658 0.270369 11.00000 0.04528 0.05700 = 0.05702 0.00429 0.01579 0.00217 AFIX 43 H4 2 0.561511 0.474661 0.238281 11.00000 -1.20000 AFIX 0 C24 1 0.523180 0.120937 0.441978 11.00000 0.05489 0.05089 = 0.06012 0.00537 0.02542 -0.00074 AFIX 43 H24 2 0.567379 0.084003 0.428590 11.00000 -1.20000 AFIX 0 C25 1 0.386672 0.126282 0.413691 11.00000 0.05234 0.06210 = 0.05147 0.00196 0.02113 -0.01362 C18 1 0.463371 0.390803 0.453740 11.00000 0.03855 0.05979 = 0.06777 -0.00274 0.01982 0.00455 AFIX 43 H18 2 0.539553 0.387668 0.491417 11.00000 -1.20000 AFIX 0 C2 1 0.526660 0.486318 0.374498 11.00000 0.04579 0.05309 = 0.06703 0.00493 0.02201 0.01159 AFIX 23 H2A 2 0.563020 0.514109 0.417360 11.00000 -1.20000 H2B 2 0.474392 0.514993 0.336477 11.00000 -1.20000 AFIX 0 O36 4 1.291539 0.362563 0.698562 11.00000 0.08137 0.11892 = 0.12704 0.04601 0.01662 0.01684 C5 1 0.731151 0.424703 0.240515 11.00000 0.05063 0.05467 = 0.05327 -0.00062 0.02121 -0.00563 C12 1 0.743652 0.161024 0.518170 11.00000 0.04174 0.06563 = 0.06360 0.01909 0.01723 0.00523 AFIX 23 H12A 2 0.765402 0.168862 0.571278 11.00000 -1.20000 H12B 2 0.767972 0.115058 0.509913 11.00000 -1.20000 AFIX 0 C40 1 0.876560 0.462204 0.587686 11.00000 0.05479 0.05883 = 0.05381 -0.00508 0.01955 0.00430 AFIX 23 H40A 2 0.899228 0.501565 0.618944 11.00000 -1.20000 H40B 2 0.818559 0.433940 0.608771 11.00000 -1.20000 AFIX 0 C16 1 0.323810 0.296709 0.490872 11.00000 0.03988 0.06889 = 0.07792 -0.00205 0.03210 0.00007 AFIX 23 H16A 2 0.229313 0.288709 0.479259 11.00000 -1.20000 H16B 2 0.350674 0.308791 0.542903 11.00000 -1.20000 AFIX 0 C38 1 1.073014 0.410029 0.654065 11.00000 0.07232 0.07608 = 0.05280 0.01020 0.01873 0.01748 AFIX 23 H38A 2 1.023867 0.383971 0.682905 11.00000 -1.20000 H38B 2 1.105529 0.450517 0.681428 11.00000 -1.20000 AFIX 0 C47 1 0.721144 0.427387 0.156836 11.00000 0.07046 0.07571 = 0.05289 0.00099 0.02424 -0.00571 C43 1 0.309851 0.070772 0.364804 11.00000 0.08043 0.08063 = 0.06741 -0.01565 0.02940 -0.03230 PART 1 O30B 4 0.806997 0.286168 0.691081 21.00000 0.07104 0.08897 = 0.09550 0.01584 -0.00784 -0.01605 PART 0 PART 2 O30A 4 0.788190 0.249361 0.697236 -21.00000 0.07752 0.07119 = 0.07447 0.01805 0.01306 -0.01090 PART 0 C34 1 1.200195 0.287882 0.782258 11.00000 0.07500 0.10763 = 0.06867 0.01936 0.00640 0.00987 AFIX 23 H34A 2 1.235184 0.255181 0.820594 11.00000 -1.20000 H34B 2 1.183373 0.329198 0.806355 11.00000 -1.20000 AFIX 0 C32 1 0.996404 0.239726 0.781781 11.00000 0.08025 0.10072 = 0.06044 0.00707 0.01263 0.00987 AFIX 23 H32A 2 0.977176 0.275946 0.812759 11.00000 -1.20000 H32B 2 1.040712 0.204304 0.814132 11.00000 -1.20000 AFIX 0 C37 1 1.185825 0.369460 0.638699 11.00000 0.08521 0.10390 = 0.07658 0.03449 0.03292 0.03624 AFIX 23 H37A 2 1.153467 0.325044 0.622065 11.00000 -1.20000 H37B 2 1.216327 0.390621 0.598498 11.00000 -1.20000 AFIX 0 C48 1 0.714883 0.501419 0.132442 11.00000 0.12269 0.09424 = 0.07647 0.01815 0.04514 0.00326 AFIX 137 H48A 2 0.637503 0.522081 0.142575 11.00000 -1.50000 H48B 2 0.711095 0.503841 0.080232 11.00000 -1.50000 H48C 2 0.792140 0.524573 0.159283 11.00000 -1.50000 AFIX 0 C35 1 1.299401 0.300823 0.737903 11.00000 0.08175 0.13324 = 0.10558 0.05469 0.02718 0.03843 AFIX 23 H35A 2 1.386240 0.298242 0.771051 11.00000 -1.20000 H35B 2 1.293589 0.264578 0.702256 11.00000 -1.20000 AFIX 0 C49 1 0.840940 0.395555 0.135781 11.00000 0.11665 0.12025 = 0.06934 -0.00253 0.05014 0.01541 AFIX 137 H49A 2 0.920150 0.416107 0.164016 11.00000 -1.50000 H49B 2 0.835354 0.402291 0.083830 11.00000 -1.50000 H49C 2 0.842666 0.348247 0.146255 11.00000 -1.50000 AFIX 0 PART 1 C28A 1 0.572103 0.282639 0.631621 21.00000 0.06094 0.07528 = 0.05852 -0.01559 0.02725 0.00007 AFIX 23 H28A 2 0.479181 0.276763 0.630698 21.00000 -1.20000 H28B 2 0.598039 0.327857 0.648539 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C28B 1 0.589350 0.248713 0.634014 -21.00000 0.05918 0.11533 = 0.05056 -0.01749 0.01992 -0.02406 AFIX 23 H28C 2 0.499688 0.252347 0.640468 -21.00000 -1.20000 H28D 2 0.617507 0.202252 0.641759 -21.00000 -1.20000 AFIX 0 PART 0 C45 1 0.364354 0.061646 0.295254 11.00000 0.12106 0.11913 = 0.07664 -0.02744 0.03678 -0.03403 AFIX 137 H45A 2 0.352855 0.102581 0.267033 11.00000 -1.50000 H45B 2 0.317716 0.025866 0.265563 11.00000 -1.50000 H45C 2 0.456623 0.050777 0.309608 11.00000 -1.50000 AFIX 0 C50 1 0.594772 0.392145 0.116906 11.00000 0.11701 0.16090 = 0.06135 -0.01574 0.01153 -0.05195 AFIX 137 H50A 2 0.597815 0.345858 0.131906 11.00000 -1.50000 H50B 2 0.586692 0.394670 0.064295 11.00000 -1.50000 H50C 2 0.520158 0.413695 0.129349 11.00000 -1.50000 AFIX 0 C31 1 0.873233 0.213826 0.736683 11.00000 0.10279 0.15541 = 0.10605 -0.01810 0.01296 -0.01119 PART 1 AFIX 23 H31A 2 0.817023 0.195583 0.767040 21.00000 -1.20000 H31B 2 0.888670 0.179687 0.702240 21.00000 -1.20000 AFIX 23 PART 0 PART 2 H31C 2 0.897229 0.180068 0.704332 -21.00000 -1.20000 H31D 2 0.829868 0.190134 0.770245 -21.00000 -1.20000 AFIX 0 PART 0 C46 1 0.331354 0.003765 0.408271 11.00000 0.22540 0.08957 = 0.10580 -0.01435 0.06046 -0.07622 AFIX 137 H46A 2 0.424276 -0.005085 0.424235 11.00000 -1.50000 H46B 2 0.289652 -0.032126 0.376784 11.00000 -1.50000 H46C 2 0.293482 0.006909 0.450777 11.00000 -1.50000 AFIX 0 PART 2 C9A 1 0.676717 0.292179 0.685931 21.00000 0.09643 0.09519 = 0.07172 -0.02910 0.01046 -0.01303 AFIX 23 H9AA 2 0.691846 0.334920 0.664050 21.00000 -1.20000 H9AB 2 0.646244 0.299602 0.731003 21.00000 -1.20000 AFIX 0 PART 0 PART 1 C9B 1 0.655790 0.230446 0.683230 -21.00000 0.07494 0.09887 = 0.05004 -0.00030 0.02476 -0.01670 AFIX 23 H9BA 2 0.662607 0.187534 0.659499 -21.00000 -1.20000 H9BB 2 0.629521 0.224341 0.729772 -21.00000 -1.20000 AFIX 0 PART 0 C29 1 0.164540 0.085676 0.342066 11.00000 0.07859 0.19577 = 0.17860 -0.10109 0.03324 -0.05805 AFIX 137 H29A 2 0.129594 0.090055 0.385506 11.00000 -1.50000 H29B 2 0.120245 0.049623 0.311826 11.00000 -1.50000 H29C 2 0.150946 0.126871 0.314341 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_1255_a.res in P2(1)/n REM R1 = 0.0643 for 6383 Fo > 4sig(Fo) and 0.0710 for all 7434 data REM 485 parameters refined using 0 restraints END WGHT 0.1119 1.2650 REM Highest difference peak 0.638, deepest hole -0.298, 1-sigma level 0.046 Q1 1 1.2333 0.3176 0.6576 11.00000 0.05 0.64 Q2 1 0.2177 0.0408 0.4181 11.00000 0.05 0.42 Q3 1 0.2272 0.1089 0.2914 11.00000 0.05 0.39 Q4 1 0.3909 0.0133 0.3455 11.00000 0.05 0.38 Q5 1 0.7147 0.3439 0.1206 11.00000 0.05 0.36 Q6 1 0.8193 0.2268 0.4830 11.00000 0.05 0.28 Q7 1 0.5831 0.4544 0.1018 11.00000 0.05 0.26 Q8 1 1.0361 0.3001 0.7691 11.00000 0.05 0.26 Q9 1 0.8410 0.4587 0.1383 11.00000 0.05 0.23 Q10 1 1.0176 0.2263 0.7354 11.00000 0.05 0.23 Q11 1 1.2678 0.3438 0.7600 11.00000 0.05 0.22 Q12 1 0.5810 0.2273 0.7954 11.00000 0.05 0.22 Q13 1 0.4753 0.4476 0.3901 11.00000 0.05 0.22 Q14 1 1.1217 0.3183 0.6202 11.00000 0.05 0.19 Q15 1 1.0194 0.3725 0.6352 11.00000 0.05 0.18 Q16 1 0.8063 0.4086 0.3792 11.00000 0.05 0.18 Q17 1 0.4595 0.2240 0.4968 11.00000 0.05 0.17 Q18 1 0.6481 0.2584 0.7416 11.00000 0.05 0.16 Q19 1 0.6684 0.4251 0.3561 11.00000 0.05 0.15 Q20 1 0.8394 0.2489 0.6573 11.00000 0.05 0.15 ; _shelx_res_checksum 24743 _olex2_date_sample_data_collection 2018-05-28 _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 1.701 _oxdiff_exptl_absorpt_empirical_full_min 0.608 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O42 O 0.75258(13) 0.42436(7) 0.46981(7) 0.0471(3) Uani 1 1 d . . . . O27 O 0.59614(14) 0.27141(9) 0.55790(8) 0.0582(4) Uani 1 1 d . . . . O39 O 0.99193(16) 0.42647(8) 0.58394(8) 0.0592(4) Uani 1 1 d . . . . N9 N 0.91690(15) 0.29074(9) 0.44162(10) 0.0474(4) Uani 1 1 d . . . . N22 N 0.96759(17) 0.23422(9) 0.42054(11) 0.0565(4) Uani 1 1 d . . . . N21 N 0.91107(18) 0.18290(9) 0.44553(12) 0.0592(5) Uani 1 1 d . . . . O33 O 1.0814(2) 0.26378(11) 0.73811(10) 0.0806(5) Uani 1 1 d . . . . C11 C 0.82367(16) 0.20721(10) 0.48306(10) 0.0428(4) Uani 1 1 d . . . . N17 N 0.35276(17) 0.35304(10) 0.44555(12) 0.0591(5) Uani 1 1 d . . . . C23 C 0.74543(17) 0.42580(9) 0.39385(11) 0.0429(4) Uani 1 1 d . . . . C1 C 0.44018(18) 0.43426(10) 0.39555(12) 0.0484(4) Uani 1 1 d . . . . C7 C 0.84366(17) 0.39321(9) 0.36676(11) 0.0446(4) Uani 1 1 d . . . . C3 C 0.63892(18) 0.45572(9) 0.34573(12) 0.0469(4) Uani 1 1 d . . . . C14 C 0.52800(18) 0.22380(10) 0.50920(11) 0.0470(4) Uani 1 1 d . . . . C10 C 0.82770(19) 0.27513(11) 0.48160(12) 0.0510(5) Uani 1 1 d . . . . H10 H 0.779155 0.304877 0.503550 0.061 Uiso 1 1 calc R . . . C13 C 0.59514(19) 0.16879(11) 0.48934(11) 0.0488(4) Uani 1 1 d . . . . N20 N 0.31842(19) 0.42252(12) 0.35371(13) 0.0709(6) Uani 1 1 d . . . . C15 C 0.39360(18) 0.23309(11) 0.47783(11) 0.0483(4) Uani 1 1 d . . . . C6 C 0.83475(19) 0.39392(10) 0.29051(12) 0.0500(4) Uani 1 1 d . . . . H6 H 0.900756 0.372967 0.272327 0.060 Uiso 1 1 calc R . . . C8 C 0.95571(17) 0.35744(10) 0.41878(12) 0.0481(4) Uani 1 1 d . . . . H8A H 1.028406 0.352038 0.394552 0.058 Uiso 1 1 calc R . . . H8B H 0.986566 0.384944 0.462585 0.058 Uiso 1 1 calc R . . . N19 N 0.26499(19) 0.37304(13) 0.38407(14) 0.0734(6) Uani 1 1 d . . . . C26 C 0.32538(19) 0.18375(11) 0.43159(12) 0.0519(5) Uani 1 1 d . . . . H26 H 0.235410 0.189396 0.411916 0.062 Uiso 1 1 calc R . . . C41 C 0.8088(2) 0.48294(10) 0.51073(12) 0.0520(5) Uani 1 1 d . . . . H41A H 0.739839 0.515277 0.512529 0.062 Uiso 1 1 calc R . . . H41B H 0.871761 0.503936 0.486439 0.062 Uiso 1 1 calc R . . . C4 C 0.6333(2) 0.45466(11) 0.27037(12) 0.0524(5) Uani 1 1 d . . . . H4 H 0.561511 0.474661 0.238281 0.063 Uiso 1 1 calc R . . . C24 C 0.5232(2) 0.12094(11) 0.44198(12) 0.0533(5) Uani 1 1 d . . . . H24 H 0.567379 0.084003 0.428590 0.064 Uiso 1 1 calc R . . . C25 C 0.3867(2) 0.12628(11) 0.41369(12) 0.0538(5) Uani 1 1 d . . . . C18 C 0.4634(2) 0.39080(11) 0.45374(13) 0.0541(5) Uani 1 1 d . . . . H18 H 0.539553 0.387668 0.491417 0.065 Uiso 1 1 calc R . . . C2 C 0.5267(2) 0.48632(11) 0.37450(13) 0.0538(5) Uani 1 1 d . . . . H2A H 0.563020 0.514109 0.417360 0.065 Uiso 1 1 calc R . . . H2B H 0.474392 0.514993 0.336477 0.065 Uiso 1 1 calc R . . . O36 O 1.2915(2) 0.36256(14) 0.69856(16) 0.1103(9) Uani 1 1 d . . . . C5 C 0.7312(2) 0.42470(11) 0.24051(12) 0.0514(5) Uani 1 1 d . . . . C12 C 0.7437(2) 0.16102(12) 0.51817(13) 0.0562(5) Uani 1 1 d . . . . H12A H 0.765402 0.168862 0.571278 0.067 Uiso 1 1 calc R . . . H12B H 0.767972 0.115058 0.509913 0.067 Uiso 1 1 calc R . . . C40 C 0.8766(2) 0.46220(11) 0.58769(12) 0.0547(5) Uani 1 1 d . . . . H40A H 0.899228 0.501565 0.618944 0.066 Uiso 1 1 calc R . . . H40B H 0.818559 0.433940 0.608771 0.066 Uiso 1 1 calc R . . . C16 C 0.3238(2) 0.29671(12) 0.49087(14) 0.0592(5) Uani 1 1 d . . . . H16A H 0.229313 0.288709 0.479259 0.071 Uiso 1 1 calc R . . . H16B H 0.350674 0.308791 0.542903 0.071 Uiso 1 1 calc R . . . C38 C 1.0730(3) 0.41003(14) 0.65406(13) 0.0664(6) Uani 1 1 d . . . . H38A H 1.023867 0.383971 0.682905 0.080 Uiso 1 1 calc R . . . H38B H 1.105529 0.450517 0.681428 0.080 Uiso 1 1 calc R . . . C47 C 0.7211(3) 0.42739(13) 0.15684(13) 0.0647(6) Uani 1 1 d . . . . C43 C 0.3099(3) 0.07077(15) 0.36480(15) 0.0741(7) Uani 1 1 d . . . . O30B O 0.8070(5) 0.2862(4) 0.6911(3) 0.0895(17) Uani 0.457(7) 1 d . P A 1 O30A O 0.7882(4) 0.2494(3) 0.6972(2) 0.0751(12) Uani 0.543(7) 1 d . P A 2 C34 C 1.2002(3) 0.28788(19) 0.78226(17) 0.0854(8) Uani 1 1 d . . . . H34A H 1.235184 0.255181 0.820594 0.102 Uiso 1 1 calc R . . . H34B H 1.183373 0.329198 0.806355 0.102 Uiso 1 1 calc R . . . C32 C 0.9964(3) 0.23973(17) 0.78178(16) 0.0810(8) Uani 1 1 d . . . . H32A H 0.977176 0.275946 0.812759 0.097 Uiso 1 1 calc R . . . H32B H 1.040712 0.204304 0.814132 0.097 Uiso 1 1 calc R . . . C37 C 1.1858(3) 0.36946(18) 0.63870(17) 0.0862(9) Uani 1 1 d . . . . H37A H 1.153467 0.325044 0.622065 0.103 Uiso 1 1 calc R . . . H37B H 1.216327 0.390621 0.598498 0.103 Uiso 1 1 calc R . . . C48 C 0.7149(4) 0.50142(18) 0.13244(18) 0.0942(10) Uani 1 1 d . . . . H48A H 0.637503 0.522081 0.142575 0.141 Uiso 1 1 calc GR . . . H48B H 0.711095 0.503841 0.080232 0.141 Uiso 1 1 calc GR . . . H48C H 0.792140 0.524573 0.159283 0.141 Uiso 1 1 calc GR . . . C35 C 1.2994(4) 0.3008(2) 0.7379(2) 0.1059(13) Uani 1 1 d . . . . H35A H 1.386240 0.298242 0.771051 0.127 Uiso 1 1 calc R . . . H35B H 1.293589 0.264578 0.702256 0.127 Uiso 1 1 calc R . . . C49 C 0.8409(4) 0.3956(2) 0.13578(18) 0.0974(10) Uani 1 1 d . . . . H49A H 0.920150 0.416107 0.164016 0.146 Uiso 1 1 calc GR . . . H49B H 0.835354 0.402291 0.083830 0.146 Uiso 1 1 calc GR . . . H49C H 0.842666 0.348247 0.146255 0.146 Uiso 1 1 calc GR . . . C28A C 0.5721(9) 0.2826(5) 0.6316(5) 0.0627(19) Uani 0.457(7) 1 d . P A 1 H28A H 0.479181 0.276763 0.630698 0.075 Uiso 0.457(7) 1 calc R P A 1 H28B H 0.598039 0.327857 0.648539 0.075 Uiso 0.457(7) 1 calc R P A 1 C28B C 0.5894(8) 0.2487(6) 0.6340(4) 0.0738(19) Uani 0.543(7) 1 d . P A 2 H28C H 0.499688 0.252347 0.640468 0.089 Uiso 0.543(7) 1 calc R P A 2 H28D H 0.617507 0.202252 0.641759 0.089 Uiso 0.543(7) 1 calc R P A 2 C45 C 0.3644(4) 0.0616(2) 0.29525(19) 0.1033(12) Uani 1 1 d . . . . H45A H 0.352855 0.102581 0.267033 0.155 Uiso 1 1 calc GR . . . H45B H 0.317716 0.025866 0.265563 0.155 Uiso 1 1 calc GR . . . H45C H 0.456623 0.050777 0.309608 0.155 Uiso 1 1 calc GR . . . C50 C 0.5948(4) 0.3921(2) 0.11691(18) 0.1145(14) Uani 1 1 d . . . . H50A H 0.597815 0.345858 0.131906 0.172 Uiso 1 1 calc GR . . . H50B H 0.586692 0.394670 0.064295 0.172 Uiso 1 1 calc GR . . . H50C H 0.520158 0.413695 0.129349 0.172 Uiso 1 1 calc GR . . . C31 C 0.8732(5) 0.2138(3) 0.7367(3) 0.1232(14) Uani 1 1 d . . . . H31A H 0.817023 0.195583 0.767040 0.148 Uiso 0.457(7) 1 calc R P A 1 H31B H 0.888670 0.179687 0.702240 0.148 Uiso 0.457(7) 1 calc R P A 1 H31C H 0.897229 0.180068 0.704332 0.148 Uiso 0.543(7) 1 calc R P A 2 H31D H 0.829868 0.190134 0.770245 0.148 Uiso 0.543(7) 1 calc R P A 2 C46 C 0.3314(6) 0.0038(2) 0.4083(2) 0.1366(19) Uani 1 1 d . . . . H46A H 0.424276 -0.005085 0.424235 0.205 Uiso 1 1 calc GR . . . H46B H 0.289652 -0.032126 0.376784 0.205 Uiso 1 1 calc GR . . . H46C H 0.293482 0.006909 0.450777 0.205 Uiso 1 1 calc GR . . . C9A C 0.6767(8) 0.2922(4) 0.6859(4) 0.089(2) Uani 0.457(7) 1 d . P A 2 H9AA H 0.691846 0.334920 0.664050 0.107 Uiso 0.457(7) 1 calc R P A 2 H9AB H 0.646244 0.299602 0.731003 0.107 Uiso 0.457(7) 1 calc R P A 2 C9B C 0.6558(5) 0.2304(3) 0.6832(3) 0.0729(17) Uani 0.543(7) 1 d . P A 1 H9BA H 0.662607 0.187534 0.659499 0.088 Uiso 0.543(7) 1 calc R P A 1 H9BB H 0.629521 0.224341 0.729772 0.088 Uiso 0.543(7) 1 calc R P A 1 C29 C 0.1645(4) 0.0857(3) 0.3421(3) 0.150(2) Uani 1 1 d . . . . H29A H 0.129594 0.090055 0.385506 0.226 Uiso 1 1 calc GR . . . H29B H 0.120245 0.049623 0.311826 0.226 Uiso 1 1 calc GR . . . H29C H 0.150946 0.126871 0.314341 0.226 Uiso 1 1 calc GR . . . 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 O42 0.0446(7) 0.0503(7) 0.0506(7) -0.0040(6) 0.0195(6) -0.0062(5) O27 0.0452(7) 0.0804(10) 0.0528(8) -0.0100(7) 0.0186(6) -0.0104(7) O39 0.0625(9) 0.0696(9) 0.0484(8) 0.0048(7) 0.0189(7) 0.0160(7) N9 0.0317(7) 0.0565(9) 0.0556(9) -0.0029(7) 0.0135(6) 0.0029(6) N22 0.0465(9) 0.0581(10) 0.0713(11) 0.0013(8) 0.0268(8) 0.0083(7) N21 0.0504(9) 0.0558(10) 0.0775(12) 0.0020(9) 0.0272(9) 0.0090(8) O33 0.0793(12) 0.1011(14) 0.0581(10) 0.0122(9) 0.0089(9) 0.0126(10) C11 0.0297(8) 0.0508(10) 0.0487(9) 0.0048(8) 0.0107(7) 0.0040(7) N17 0.0384(8) 0.0661(11) 0.0789(12) -0.0023(9) 0.0259(8) 0.0074(7) C23 0.0371(8) 0.0442(9) 0.0513(10) -0.0024(7) 0.0181(7) -0.0034(7) C1 0.0347(9) 0.0550(11) 0.0606(11) 0.0002(9) 0.0210(8) 0.0112(7) C7 0.0345(8) 0.0469(9) 0.0564(10) -0.0028(8) 0.0184(8) -0.0034(7) C3 0.0402(9) 0.0458(9) 0.0593(11) 0.0015(8) 0.0205(8) 0.0019(7) C14 0.0391(9) 0.0576(11) 0.0481(10) 0.0026(8) 0.0176(8) -0.0057(8) C10 0.0425(10) 0.0548(11) 0.0626(12) -0.0026(9) 0.0258(9) 0.0007(8) C13 0.0394(9) 0.0568(11) 0.0538(10) 0.0120(9) 0.0182(8) 0.0010(8) N20 0.0412(9) 0.0878(15) 0.0839(14) 0.0102(11) 0.0146(9) 0.0082(9) C15 0.0362(9) 0.0595(11) 0.0544(11) 0.0049(8) 0.0213(8) -0.0025(8) C6 0.0433(10) 0.0535(10) 0.0596(11) -0.0044(9) 0.0251(9) -0.0024(8) C8 0.0297(8) 0.0553(10) 0.0623(11) -0.0023(9) 0.0170(8) -0.0027(7) N19 0.0381(9) 0.0924(15) 0.0897(15) 0.0090(12) 0.0149(9) 0.0023(9) C26 0.0365(9) 0.0672(12) 0.0547(11) 0.0067(9) 0.0156(8) -0.0068(8) C41 0.0510(11) 0.0476(10) 0.0578(11) -0.0064(8) 0.0132(9) 0.0039(8) C4 0.0453(10) 0.0570(11) 0.0570(11) 0.0043(9) 0.0158(9) 0.0022(8) C24 0.0549(11) 0.0509(10) 0.0601(12) 0.0054(9) 0.0254(9) -0.0007(8) C25 0.0523(11) 0.0621(12) 0.0515(11) 0.0020(9) 0.0211(9) -0.0136(9) C18 0.0386(9) 0.0598(12) 0.0678(13) -0.0027(10) 0.0198(9) 0.0045(8) C2 0.0458(10) 0.0531(11) 0.0670(13) 0.0049(9) 0.0220(9) 0.0116(8) O36 0.0814(14) 0.1189(19) 0.127(2) 0.0460(16) 0.0166(14) 0.0168(13) C5 0.0506(11) 0.0547(11) 0.0533(11) -0.0006(8) 0.0212(9) -0.0056(8) C12 0.0417(10) 0.0656(12) 0.0636(12) 0.0191(10) 0.0172(9) 0.0052(9) C40 0.0548(11) 0.0588(11) 0.0538(11) -0.0051(9) 0.0195(9) 0.0043(9) C16 0.0399(10) 0.0689(13) 0.0779(15) -0.0020(11) 0.0321(10) 0.0001(9) C38 0.0723(15) 0.0761(15) 0.0528(12) 0.0102(11) 0.0187(11) 0.0175(12) C47 0.0705(14) 0.0757(15) 0.0529(12) 0.0010(10) 0.0242(11) -0.0057(11) C43 0.0804(17) 0.0806(17) 0.0674(15) -0.0157(12) 0.0294(13) -0.0323(13) O30B 0.071(3) 0.089(4) 0.095(4) 0.016(3) -0.008(2) -0.016(3) O30A 0.078(2) 0.071(3) 0.074(2) 0.018(2) 0.0131(18) -0.011(2) C34 0.0750(18) 0.108(2) 0.0687(16) 0.0194(16) 0.0064(14) 0.0099(16) C32 0.0803(18) 0.101(2) 0.0604(14) 0.0071(14) 0.0126(13) 0.0099(16) C37 0.0852(19) 0.104(2) 0.0766(17) 0.0345(16) 0.0329(15) 0.0362(16) C48 0.123(3) 0.094(2) 0.0765(18) 0.0181(16) 0.0451(19) 0.0033(19) C35 0.082(2) 0.133(3) 0.106(2) 0.055(2) 0.0272(18) 0.038(2) C49 0.117(3) 0.120(3) 0.0693(17) -0.0025(17) 0.0501(18) 0.015(2) C28A 0.061(4) 0.075(4) 0.059(4) -0.016(4) 0.027(3) 0.000(4) C28B 0.059(4) 0.115(6) 0.051(3) -0.017(4) 0.020(3) -0.024(4) C45 0.121(3) 0.119(3) 0.0766(19) -0.0274(19) 0.0368(19) -0.034(2) C50 0.117(3) 0.161(4) 0.0613(17) -0.016(2) 0.0115(17) -0.052(3) C31 0.103(3) 0.155(4) 0.106(3) -0.018(3) 0.013(2) -0.011(3) C46 0.225(5) 0.090(2) 0.106(3) -0.014(2) 0.060(3) -0.076(3) C9A 0.096(5) 0.095(5) 0.072(4) -0.029(4) 0.010(3) -0.013(4) C9B 0.075(3) 0.099(4) 0.050(3) 0.000(2) 0.025(2) -0.017(3) C29 0.079(2) 0.196(5) 0.179(5) -0.101(4) 0.033(3) -0.058(3) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 6 4 -4 0.2362 -6 7 1 0.2663 6 4 1 0.2279 2 -2 10 0.2093 1 -1 -12 0.2305 1 -9 8 0.2007 3 6 -11 0.2547 1 -11 6 0.1901 -1 -12 4 0.1868 -4 10 -1 0.1369 -1 -13 1 0.1795 7 3 -2 0.2216 0 13 -1 0.2168 -1 -13 -2 0.1871 0 11 6 0.1993 0 -9 -9 0.1994 -1 9 8 0.1825 0 -5 -11 0.2158 6 -7 -1 0.1725 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C23 O42 C41 115.88(15) C14 O27 C28A 122.8(4) C14 O27 C28B 106.2(4) C40 O39 C38 113.95(17) N22 N9 C10 109.49(17) N22 N9 C8 121.29(16) C10 N9 C8 129.17(17) N21 N22 N9 108.15(16) N22 N21 C11 108.13(17) C34 O33 C32 111.5(2) N21 C11 C12 120.91(18) C10 C11 N21 108.59(17) C10 C11 C12 130.50(18) N19 N17 C18 109.0(2) N19 N17 C16 121.30(19) C18 N17 C16 129.7(2) O42 C23 C7 118.67(17) C3 C23 O42 120.52(16) C3 C23 C7 120.71(18) N20 C1 C18 108.58(19) N20 C1 C2 121.2(2) C18 C1 C2 130.18(19) C23 C7 C8 120.72(18) C6 C7 C23 118.38(18) C6 C7 C8 120.89(17) C23 C3 C2 120.80(18) C4 C3 C23 118.97(17) C4 C3 C2 120.17(18) O27 C14 C13 119.76(17) O27 C14 C15 119.59(18) C13 C14 C15 120.58(19) N9 C10 C11 105.62(17) N9 C10 H10 127.2 C11 C10 H10 127.2 C14 C13 C12 121.2(2) C24 C13 C14 118.32(18) C24 C13 C12 120.5(2) N19 N20 C1 108.5(2) C14 C15 C16 121.18(19) C26 C15 C14 118.98(19) C26 C15 C16 119.79(18) C7 C6 H6 118.7 C5 C6 C7 122.67(18) C5 C6 H6 118.7 N9 C8 C7 112.61(15) N9 C8 H8A 109.1 N9 C8 H8B 109.1 C7 C8 H8A 109.1 C7 C8 H8B 109.1 H8A C8 H8B 107.8 N20 N19 N17 108.12(19) C15 C26 H26 118.9 C25 C26 C15 122.24(19) C25 C26 H26 118.9 O42 C41 H41A 109.9 O42 C41 H41B 109.9 O42 C41 C40 108.93(17) H41A C41 H41B 108.3 C40 C41 H41A 109.9 C40 C41 H41B 109.9 C3 C4 H4 118.7 C3 C4 C5 122.64(19) C5 C4 H4 118.7 C13 C24 H24 118.8 C13 C24 C25 122.5(2) C25 C24 H24 118.8 C26 C25 C24 117.1(2) C26 C25 C43 122.0(2) C24 C25 C43 120.9(2) N17 C18 C1 105.8(2) N17 C18 H18 127.1 C1 C18 H18 127.1 C1 C2 C3 112.03(17) C1 C2 H2A 109.2 C1 C2 H2B 109.2 C3 C2 H2A 109.2 C3 C2 H2B 109.2 H2A C2 H2B 107.9 C37 O36 C35 116.1(3) C6 C5 C4 116.57(19) C6 C5 C47 123.47(19) C4 C5 C47 120.0(2) C11 C12 C13 114.16(16) C11 C12 H12A 108.7 C11 C12 H12B 108.7 C13 C12 H12A 108.7 C13 C12 H12B 108.7 H12A C12 H12B 107.6 O39 C40 C41 108.18(17) O39 C40 H40A 110.1 O39 C40 H40B 110.1 C41 C40 H40A 110.1 C41 C40 H40B 110.1 H40A C40 H40B 108.4 N17 C16 C15 112.24(16) N17 C16 H16A 109.2 N17 C16 H16B 109.2 C15 C16 H16A 109.2 C15 C16 H16B 109.2 H16A C16 H16B 107.9 O39 C38 H38A 110.5 O39 C38 H38B 110.5 O39 C38 C37 106.1(2) H38A C38 H38B 108.7 C37 C38 H38A 110.5 C37 C38 H38B 110.5 C5 C47 C48 108.6(2) C49 C47 C5 112.0(2) C49 C47 C48 107.7(2) C50 C47 C5 109.0(2) C50 C47 C48 108.9(3) C50 C47 C49 110.5(3) C25 C43 C45 109.8(2) C25 C43 C46 108.7(3) C45 C43 C46 107.4(3) C29 C43 C25 112.2(3) C29 C43 C45 109.3(3) C29 C43 C46 109.4(4) C31 O30B C9B 77.4(4) C31 O30A C9A 152.3(5) O33 C34 H34A 109.3 O33 C34 H34B 109.3 O33 C34 C35 111.7(3) H34A C34 H34B 107.9 C35 C34 H34A 109.3 C35 C34 H34B 109.3 O33 C32 H32A 109.2 O33 C32 H32B 109.2 O33 C32 C31 112.1(3) H32A C32 H32B 107.9 C31 C32 H32A 109.2 C31 C32 H32B 109.2 O36 C37 C38 114.5(3) O36 C37 H37A 108.6 O36 C37 H37B 108.6 C38 C37 H37A 108.6 C38 C37 H37B 108.6 H37A C37 H37B 107.6 C47 C48 H48A 109.5 C47 C48 H48B 109.5 C47 C48 H48C 109.5 H48A C48 H48B 109.5 H48A C48 H48C 109.5 H48B C48 H48C 109.5 O36 C35 C34 118.0(3) O36 C35 H35A 107.8 O36 C35 H35B 107.8 C34 C35 H35A 107.8 C34 C35 H35B 107.8 H35A C35 H35B 107.1 C47 C49 H49A 109.5 C47 C49 H49B 109.5 C47 C49 H49C 109.5 H49A C49 H49B 109.5 H49A C49 H49C 109.5 H49B C49 H49C 109.5 O27 C28A H28A 110.4 O27 C28A H28B 110.4 O27 C28A C9B 106.5(5) H28A C28A H28B 108.6 C9B C28A H28A 110.4 C9B C28A H28B 110.4 O27 C28B H28C 110.4 O27 C28B H28D 110.4 H28C C28B H28D 108.6 C9A C28B O27 106.7(6) C9A C28B H28C 110.4 C9A C28B H28D 110.4 C43 C45 H45A 109.5 C43 C45 H45B 109.5 C43 C45 H45C 109.5 H45A C45 H45B 109.5 H45A C45 H45C 109.5 H45B C45 H45C 109.5 C47 C50 H50A 109.5 C47 C50 H50B 109.5 C47 C50 H50C 109.5 H50A C50 H50B 109.5 H50A C50 H50C 109.5 H50B C50 H50C 109.5 O30B C31 H31A 111.6 O30B C31 H31B 111.6 O30A C31 C32 123.7(5) O30A C31 H31C 106.4 O30A C31 H31D 106.4 C32 C31 O30B 100.7(4) C32 C31 H31A 111.6 C32 C31 H31B 111.6 C32 C31 H31C 106.4 C32 C31 H31D 106.4 H31A C31 H31B 109.4 H31C C31 H31D 106.5 C43 C46 H46A 109.5 C43 C46 H46B 109.5 C43 C46 H46C 109.5 H46A C46 H46B 109.5 H46A C46 H46C 109.5 H46B C46 H46C 109.5 O30A C9A C28B 96.1(7) O30A C9A H9AA 112.5 O30A C9A H9AB 112.5 C28B C9A H9AA 112.5 C28B C9A H9AB 112.5 H9AA C9A H9AB 110.0 O30B C9B H9BA 113.7 O30B C9B H9BB 113.7 C28A C9B O30B 89.7(5) C28A C9B H9BA 113.7 C28A C9B H9BB 113.7 H9BA C9B H9BB 110.9 C43 C29 H29A 109.5 C43 C29 H29B 109.5 C43 C29 H29C 109.5 H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O42 C23 1.392(2) O42 C41 1.439(2) O27 C14 1.385(3) O27 C28A 1.461(8) O27 C28B 1.497(8) O39 C40 1.410(3) O39 C38 1.415(3) N9 N22 1.338(2) N9 C10 1.350(3) N9 C8 1.476(3) N22 N21 1.314(3) N21 C11 1.354(3) O33 C34 1.401(4) O33 C32 1.412(4) C11 C10 1.352(3) C11 C12 1.486(3) N17 N19 1.346(3) N17 C18 1.353(3) N17 C16 1.472(3) C23 C7 1.397(2) C23 C3 1.387(3) C1 N20 1.345(3) C1 C18 1.359(3) C1 C2 1.481(3) C7 C6 1.394(3) C7 C8 1.509(3) C3 C4 1.384(3) C3 C2 1.518(3) C14 C13 1.392(3) C14 C15 1.398(3) C10 H10 0.9300 C13 C24 1.391(3) C13 C12 1.522(3) N20 N19 1.318(3) C15 C26 1.386(3) C15 C16 1.506(3) C6 H6 0.9300 C6 C5 1.391(3) C8 H8A 0.9700 C8 H8B 0.9700 C26 H26 0.9300 C26 C25 1.386(3) C41 H41A 0.9700 C41 H41B 0.9700 C41 C40 1.496(3) C4 H4 0.9300 C4 C5 1.399(3) C24 H24 0.9300 C24 C25 1.400(3) C25 C43 1.531(3) C18 H18 0.9300 C2 H2A 0.9700 C2 H2B 0.9700 O36 C37 1.377(4) O36 C35 1.421(4) C5 C47 1.530(3) C12 H12A 0.9700 C12 H12B 0.9700 C40 H40A 0.9700 C40 H40B 0.9700 C16 H16A 0.9700 C16 H16B 0.9700 C38 H38A 0.9700 C38 H38B 0.9700 C38 C37 1.504(4) C47 C48 1.537(4) C47 C49 1.526(4) C47 C50 1.523(4) C43 C45 1.533(4) C43 C46 1.546(5) C43 C29 1.503(5) O30B C31 1.729(9) O30B C9B 1.902(8) O30A C31 1.232(6) O30A C9A 1.415(9) C34 H34A 0.9700 C34 H34B 0.9700 C34 C35 1.482(5) C32 H32A 0.9700 C32 H32B 0.9700 C32 C31 1.454(5) C37 H37A 0.9700 C37 H37B 0.9700 C48 H48A 0.9600 C48 H48B 0.9600 C48 H48C 0.9600 C35 H35A 0.9700 C35 H35B 0.9700 C49 H49A 0.9600 C49 H49B 0.9600 C49 H49C 0.9600 C28A H28A 0.9700 C28A H28B 0.9700 C28A C9B 1.538(10) C28B H28C 0.9700 C28B H28D 0.9700 C28B C9A 1.448(9) C45 H45A 0.9600 C45 H45B 0.9600 C45 H45C 0.9600 C50 H50A 0.9600 C50 H50B 0.9600 C50 H50C 0.9600 C31 H31A 0.9700 C31 H31B 0.9700 C31 H31C 0.9700 C31 H31D 0.9700 C46 H46A 0.9600 C46 H46B 0.9600 C46 H46C 0.9600 C9A H9AA 0.9700 C9A H9AB 0.9700 C9B H9BA 0.9700 C9B H9BB 0.9700 C29 H29A 0.9600 C29 H29B 0.9600 C29 H29C 0.9600 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 6.4029 3.5692 -4.4597 -0.6113 0.4677 0.6385 -5.7475 6.5985 0.8681 0.0090 -0.0021 -1.0000 6.1312 3.6198 1.1369 -0.7502 0.0186 0.6609 1.8936 -2.1971 10.2826 -0.2985 -0.8454 0.4430 0.7629 -0.9259 -11.9049 0.3333 0.9428 0.0091 1.2658 -8.6231 7.9214 0.2293 -0.7707 0.5945 2.7013 5.7038 -10.5032 -0.2845 0.9586 0.0090 0.8662 -10.7373 5.9795 0.4510 -0.6545 0.6069 -0.7028 -12.1007 4.1829 0.7133 -0.5462 0.4392 -3.7265 10.3170 -1.3029 -0.3285 0.2508 -0.9106 -1.1075 -12.7143 1.0391 0.8730 -0.3083 0.3779 6.5520 2.9267 -1.6646 -0.6605 0.2342 0.7134 -0.0825 12.8760 -0.7797 -0.7962 0.2810 -0.5358 -0.6163 -12.5020 -2.4307 0.9179 -0.0232 0.3960 -0.3706 11.4045 5.5779 -0.8578 -0.2551 -0.4463 0.1606 -8.7499 -8.6503 0.7908 0.5444 0.2798 -0.7002 9.1173 8.4671 -0.7663 -0.5277 -0.3664 0.1215 -4.8274 -10.8916 0.6056 0.7903 0.0934 5.7264 -6.6952 -0.9755 0.0019 0.0088 1.0000