#------------------------------------------------------------------------------ #$Date: 2019-11-29 20:36:01 +0200 (Fri, 29 Nov 2019) $ #$Revision: 244812 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239601.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_7239601 loop_ _publ_author_name 'Shen, Jie' 'Bai, Hongzhen' 'Zhou, Xinbo' 'Liu, Jiyong' 'Hu, Xiurong' 'Chu, Paul K.' 'Tang, Guping' _publ_section_title ; Spontaneous single-crystal to single-crystal transition with self-healing cracks involving solvent exchange ; _journal_issue 7 _journal_name_full CrystEngComm _journal_page_first 1102 _journal_paper_doi 10.1039/C8CE02110D _journal_volume 21 _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C27 H37 N3 O7 S, C2 H6 O' _chemical_formula_sum 'C29 H43 N3 O8 S' _chemical_formula_weight 593.72 _chemical_name_common 'darunavir ethanol solvate' _chemical_name_systematic '(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate ethanol solvate' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-08-24 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-08-24 deposited with the CCDC. 2019-02-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9846(5) _cell_length_b 16.6017(10) _cell_length_c 19.0274(10) _cell_measurement_reflns_used 26982 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 51.992 _cell_measurement_theta_min 6.382 _cell_volume 3154.0(3) _computing_cell_refinement 'PROCESS-AUTO (Rigaku,2006)' _computing_data_collection 'PROCESS-AUTO (Rigaku,2006)' _computing_data_reduction 'CrystalStructure (Rigaku,2007)' _computing_molecular_graphics 'Ortep3 for windows (Farrugia,1997) and Diamond (Brandengurg & Putz, 2005)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type R-AXIS-RAPID _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1089 _diffrn_reflns_av_unetI/netI 0.0931 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 26982 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.996 _diffrn_reflns_theta_min 3.191 _diffrn_source 'rotating anode' _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_correction_T_min 0.9313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_description chunk _exptl_crystal_F_000 1272 _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.290 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.050 _refine_ls_abs_structure_details ; Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 375 _refine_ls_number_reflns 6191 _refine_ls_number_restraints 13 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.1451 _refine_ls_R_factor_gt 0.0923 _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^)+(0.0523P)^2^+1.4336P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1391 _refine_ls_wR_factor_ref 0.1592 _reflns_Friedel_coverage 0.779 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 3911 _reflns_number_total 6191 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL dalunav in P 21 21 21 dl-ethy.res created by SHELXL-2018/3 at 13:36:02 on 24-Aug-2018 CELL 0.71073 9.9846 16.6017 19.0274 90 90 90 ZERR 4 0.0005 0.001 0.001 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 116 172 12 32 4 EQIV $1 0.5+X,0.5-Y,-Z EQIV $2 -X,0.5+Y,0.5-Z EQIV $3 -1+X,+Y,+Z EQIV $4 1-X,-0.5+Y,0.5-Z DFIX 1.54 0.002 C28 C29 ISOR 0.0005 0.001 C28 C29 L.S. 30 PLAN 3 SIZE 0.16 0.2 0.47 TEMP 23 HTAB N2 O6_$1 HTAB N3 O4_$2 HTAB N3 O8_$3 HTAB O3 O8_$4 HTAB O8 O1 BOND $H CONF fmap 2 acta MERG 2 OMIT -3 52 REM REM REM WGHT 0.052300 1.433600 FVAR 0.35334 C1 1 0.316806 0.330570 0.226036 11.00000 0.03782 0.04028 = 0.04537 -0.00078 -0.00064 -0.00305 AFIX 23 H1A 2 0.249049 0.351161 0.194225 11.00000 -1.20000 H1B 2 0.277250 0.327283 0.272509 11.00000 -1.20000 AFIX 0 C2 1 0.357079 0.246338 0.202482 11.00000 0.03095 0.03850 = 0.04647 0.00632 -0.00255 0.00637 AFIX 13 H2 2 0.401127 0.251201 0.156651 11.00000 -1.20000 AFIX 0 C3 1 0.235680 0.192655 0.193285 11.00000 0.03599 0.03403 = 0.04173 0.00459 -0.00048 0.00056 AFIX 13 H3 2 0.191042 0.187567 0.238940 11.00000 -1.20000 AFIX 0 C4 1 0.021562 0.254293 0.164052 11.00000 0.03441 0.03450 = 0.04266 -0.00463 -0.00282 -0.00448 C5 1 -0.184875 0.304262 0.117558 11.00000 0.03302 0.05867 = 0.04542 -0.00074 0.00235 0.01546 AFIX 13 H5 2 -0.185862 0.338533 0.159491 11.00000 -1.20000 AFIX 0 C6 1 -0.217193 0.352649 0.051596 11.00000 0.06007 0.05189 = 0.06670 0.00183 -0.00713 0.00656 AFIX 23 H6A 2 -0.278822 0.396187 0.062082 11.00000 -1.20000 H6B 2 -0.136436 0.375020 0.031051 11.00000 -1.20000 AFIX 0 C7 1 -0.357267 0.241306 0.046716 11.00000 0.04508 0.07612 = 0.05442 -0.00582 -0.00514 0.01112 AFIX 13 H7 2 -0.450353 0.259899 0.048604 11.00000 -1.20000 AFIX 0 C8 1 -0.242016 0.124303 0.054727 11.00000 0.07328 0.05893 = 0.06270 -0.00408 -0.01063 0.00782 AFIX 23 H8A 2 -0.156427 0.139307 0.034470 11.00000 -1.20000 H8B 2 -0.251725 0.066222 0.052535 11.00000 -1.20000 AFIX 0 C9 1 -0.254054 0.154246 0.129463 11.00000 0.05547 0.06665 = 0.05243 0.00341 -0.00428 -0.01093 AFIX 23 H9A 2 -0.321615 0.124264 0.155108 11.00000 -1.20000 H9B 2 -0.169247 0.149914 0.154042 11.00000 -1.20000 AFIX 0 C10 1 -0.294762 0.241232 0.120589 11.00000 0.03189 0.07241 = 0.04462 -0.00230 0.00210 0.00200 AFIX 13 H10 2 -0.361932 0.256049 0.155849 11.00000 -1.20000 AFIX 0 C11 1 0.277818 0.107646 0.168823 11.00000 0.04872 0.03638 = 0.06884 -0.00005 -0.00142 -0.00106 AFIX 23 H11A 2 0.323834 0.112068 0.124091 11.00000 -1.20000 H11B 2 0.340460 0.085374 0.202597 11.00000 -1.20000 AFIX 0 C12 1 0.160741 0.050230 0.160787 11.00000 0.05475 0.02733 = 0.06442 0.00384 0.01407 0.00528 C13 1 0.105456 0.034066 0.096179 11.00000 0.06609 0.04906 = 0.06921 -0.00020 0.01331 -0.00878 AFIX 43 H13 2 0.138822 0.059922 0.056512 11.00000 -1.20000 AFIX 0 C14 1 0.000493 -0.020295 0.089168 11.00000 0.06362 0.06696 = 0.08386 -0.01997 0.00609 -0.01229 AFIX 43 H14 2 -0.035759 -0.031248 0.045171 11.00000 -1.20000 AFIX 0 C15 1 -0.048887 -0.057561 0.148018 11.00000 0.07221 0.06312 = 0.13393 -0.02083 0.03230 -0.02281 AFIX 43 H15 2 -0.118368 -0.094556 0.143810 11.00000 -1.20000 AFIX 0 C16 1 0.002783 -0.040908 0.212332 11.00000 0.10390 0.07677 = 0.09329 0.00545 0.02924 -0.03732 AFIX 43 H16 2 -0.032749 -0.065522 0.252082 11.00000 -1.20000 AFIX 0 C17 1 0.108091 0.012548 0.218900 11.00000 0.09712 0.05203 = 0.07167 0.00055 0.00357 -0.00775 AFIX 43 H17 2 0.143742 0.023156 0.263096 11.00000 -1.20000 AFIX 0 C18 1 0.448013 0.431556 0.295286 11.00000 0.05631 0.04927 = 0.05398 -0.00786 -0.00045 -0.00566 AFIX 23 H18A 2 0.361685 0.451848 0.310560 11.00000 -1.20000 H18B 2 0.506645 0.477394 0.288026 11.00000 -1.20000 AFIX 0 C19 1 0.506074 0.378523 0.352364 11.00000 0.07252 0.05302 = 0.04595 -0.00104 -0.00359 -0.00167 AFIX 13 H19 2 0.448251 0.331213 0.357667 11.00000 -1.20000 AFIX 0 C20 1 0.505600 0.425077 0.421697 11.00000 0.13063 0.09689 = 0.05381 -0.01951 -0.00905 0.00257 AFIX 137 H20A 2 0.533662 0.390134 0.459103 11.00000 -1.50000 H20B 2 0.416801 0.444437 0.431125 11.00000 -1.50000 H20C 2 0.566040 0.469889 0.418396 11.00000 -1.50000 AFIX 0 C21 1 0.645851 0.349879 0.334926 11.00000 0.07621 0.07972 = 0.08931 -0.00526 -0.02748 0.00977 AFIX 137 H21A 2 0.645324 0.323647 0.289964 11.00000 -1.50000 H21B 2 0.675453 0.312625 0.370249 11.00000 -1.50000 H21C 2 0.705565 0.395171 0.333489 11.00000 -1.50000 AFIX 0 C22 1 0.315956 0.508917 0.148773 11.00000 0.03601 0.03993 = 0.04196 0.00355 0.00311 0.00229 C23 1 0.319326 0.583014 0.183648 11.00000 0.04557 0.03858 = 0.04804 -0.00133 0.00441 -0.00524 AFIX 43 H23 2 0.394650 0.597571 0.209441 11.00000 -1.20000 AFIX 0 C24 1 0.212982 0.633758 0.179968 11.00000 0.06492 0.03252 = 0.05726 -0.00835 0.00275 -0.00530 AFIX 43 H24 2 0.217511 0.683332 0.202605 11.00000 -1.20000 AFIX 0 C25 1 0.097966 0.613596 0.143377 11.00000 0.05378 0.04820 = 0.04063 0.00664 0.00247 0.00489 C26 1 0.093795 0.539230 0.109206 11.00000 0.05380 0.06158 = 0.04567 0.00165 -0.01114 -0.00192 AFIX 43 H26 2 0.017200 0.524273 0.084647 11.00000 -1.20000 AFIX 0 C27 1 0.201130 0.488150 0.111461 11.00000 0.05966 0.04422 = 0.04288 -0.00814 -0.00853 0.00748 AFIX 43 H27 2 0.197383 0.439137 0.087876 11.00000 -1.20000 AFIX 0 C28 1 0.623623 0.656579 0.055624 11.00000 0.15208 0.15197 = 0.15182 -0.00024 -0.00024 -0.00024 AFIX 23 H28A 2 0.529227 0.669753 0.059246 11.00000 -1.20000 H28B 2 0.633476 0.610291 0.024948 11.00000 -1.20000 AFIX 0 C29 1 0.702792 0.728673 0.026734 11.00000 0.21457 0.21469 = 0.21382 0.00019 0.00024 0.00070 AFIX 137 H29A 2 0.706539 0.770319 0.061682 11.00000 -1.50000 H29B 2 0.659257 0.748926 -0.014635 11.00000 -1.50000 H29C 2 0.792059 0.711829 0.015100 11.00000 -1.50000 AFIX 0 N1 3 0.431175 0.388250 0.228084 11.00000 0.04117 0.04137 = 0.04198 0.00260 -0.00391 -0.00391 N2 3 0.140801 0.226164 0.143796 11.00000 0.03153 0.04465 = 0.03494 0.00076 0.00446 0.00265 AFIX 43 H2A 2 0.161828 0.228025 0.099996 11.00000 -1.20000 AFIX 0 N3 3 -0.007324 0.666938 0.140007 11.00000 0.06225 0.06754 = 0.06825 -0.00356 -0.00383 0.01415 AFIX 3 H3A 2 -0.002774 0.707718 0.167777 11.00000 -1.20000 H3B 2 -0.087024 0.650528 0.130547 11.00000 -1.20000 AFIX 0 O1 4 0.570778 0.487897 0.165630 11.00000 0.04237 0.04790 = 0.08103 0.00638 0.00653 -0.00833 O2 4 0.442133 0.386293 0.098293 11.00000 0.06312 0.04870 = 0.04789 -0.00734 0.00797 0.00441 O3 4 0.450717 0.211183 0.250111 11.00000 0.04036 0.04756 = 0.07368 0.00387 -0.01598 0.00594 AFIX 147 H3C 2 0.412049 0.198327 0.286439 11.00000 -1.50000 AFIX 0 O4 4 -0.016782 0.263795 0.222963 11.00000 0.04071 0.06072 = 0.03863 -0.00282 0.00091 0.01103 O5 4 -0.053413 0.270211 0.105775 11.00000 0.03214 0.06524 = 0.03798 -0.00419 0.00097 0.01062 O6 4 -0.277670 0.294828 0.005208 11.00000 0.06345 0.08136 = 0.04927 -0.00020 -0.01007 0.01163 O7 4 -0.350451 0.163903 0.019178 11.00000 0.07226 0.07205 = 0.06140 -0.01427 -0.01986 0.00564 O8 4 0.678949 0.639417 0.124581 11.00000 0.10347 0.08943 = 0.08226 0.01124 -0.02388 -0.02759 AFIX 147 H8 2 0.650898 0.595784 0.138407 11.00000 -1.50000 AFIX 0 S1 5 0.449140 0.441466 0.155864 11.00000 0.04175 0.03987 = 0.05232 -0.00058 0.00124 -0.00069 HKLF 4 REM dalunav in P 21 21 21 REM wR2 = 0.1592, GooF = S = 1.103, Restrained GooF = 1.102 for all data REM R1 = 0.0923 for 3911 Fo > 4sig(Fo) and 0.1451 for all 6191 data REM 375 parameters refined using 13 restraints END WGHT 0.0549 1.4350 REM Highest difference peak 0.290, deepest hole -0.306, 1-sigma level 0.050 Q1 1 0.5402 0.6970 0.0209 11.00000 0.05 0.29 Q2 1 0.3739 0.4814 0.1505 11.00000 0.05 0.23 Q3 1 0.6782 0.6473 0.0372 11.00000 0.05 0.22 REM The information below was added by Olex2. REM REM R1 = 0.0923 for 3911 Fo > 4sig(Fo) and 0.1451 for all 30521 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.29, deepest hole -0.31 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1451 REM R1_gt = 0.0923 REM wR_ref = 0.1592 REM GOOF = 1.103 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 30521 REM Reflections_gt = 3911 REM Parameters = n/a REM Hole = -0.31 REM Peak = 0.29 REM Flack = 0.01(5) ; _cod_data_source_file c8ce02110d2.cif _cod_data_source_block dl-ethy _cod_database_code 7239601 _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 0.976 _shelx_estimated_absorpt_t_min 0.931 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances C28-C29 1.54 with sigma of 0.002 3. Uiso/Uaniso restraints and constraints Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.0005 and sigma for terminal atoms of 0.001 4.a Riding coordinates: N3(H3A,H3B) 4.b Ternary CH refined with riding coordinates: C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C19(H19) 4.c Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A, H18B), C28(H28A,H28B) 4.d Aromatic/amide H refined with riding coordinates: C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C23(H23), C24(H24), C26(H26), C27(H27), N2(H2A) 4.e Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C) 4.f Idealised tetrahedral OH refined as rotating group: O3(H3C), O8(H8) ; _olex2_submission_original_sample_id DLNW-C2H5OH _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, 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_adp C1 C 0.3168(6) 0.3306(4) 0.2260(4) 0.0412(16) Uani 1 1 d . . H1A H 0.249049 0.351161 0.194225 0.049 Uiso 1 1 calc R . H1B H 0.277250 0.327283 0.272509 0.049 Uiso 1 1 calc R . C2 C 0.3571(6) 0.2463(4) 0.2025(3) 0.0386(15) Uani 1 1 d . . H2 H 0.401127 0.251201 0.156651 0.046 Uiso 1 1 calc R . C3 C 0.2357(6) 0.1927(4) 0.1933(3) 0.0372(15) Uani 1 1 d . . H3 H 0.191042 0.187567 0.238940 0.045 Uiso 1 1 calc R . C4 C 0.0216(6) 0.2543(4) 0.1641(3) 0.0372(15) Uani 1 1 d . . C5 C -0.1849(6) 0.3043(4) 0.1176(4) 0.0457(17) Uani 1 1 d . . H5 H -0.185862 0.338533 0.159491 0.055 Uiso 1 1 calc R . C6 C -0.2172(8) 0.3526(5) 0.0516(4) 0.060(2) Uani 1 1 d . . H6A H -0.278822 0.396187 0.062082 0.071 Uiso 1 1 calc R . H6B H -0.136436 0.375020 0.031051 0.071 Uiso 1 1 calc R . C7 C -0.3573(7) 0.2413(5) 0.0467(4) 0.059(2) Uani 1 1 d . . H7 H -0.450353 0.259899 0.048604 0.070 Uiso 1 1 calc R . C8 C -0.2420(8) 0.1243(5) 0.0547(4) 0.065(2) Uani 1 1 d . . H8A H -0.156427 0.139307 0.034470 0.078 Uiso 1 1 calc R . H8B H -0.251725 0.066222 0.052535 0.078 Uiso 1 1 calc R . C9 C -0.2541(7) 0.1542(5) 0.1295(4) 0.058(2) Uani 1 1 d . . H9A H -0.321615 0.124264 0.155108 0.070 Uiso 1 1 calc R . H9B H -0.169247 0.149914 0.154042 0.070 Uiso 1 1 calc R . C10 C -0.2948(6) 0.2412(4) 0.1206(3) 0.0496(18) Uani 1 1 d . . H10 H -0.361932 0.256049 0.155849 0.060 Uiso 1 1 calc R . C11 C 0.2778(7) 0.1076(4) 0.1688(4) 0.0513(18) Uani 1 1 d . . H11A H 0.323834 0.112068 0.124091 0.062 Uiso 1 1 calc R . H11B H 0.340460 0.085374 0.202597 0.062 Uiso 1 1 calc R . C12 C 0.1607(7) 0.0502(4) 0.1608(4) 0.0488(17) Uani 1 1 d . . C13 C 0.1055(8) 0.0341(4) 0.0962(4) 0.061(2) Uani 1 1 d . . H13 H 0.138822 0.059922 0.056512 0.074 Uiso 1 1 calc R . C14 C 0.0005(8) -0.0203(5) 0.0892(5) 0.071(2) Uani 1 1 d . . H14 H -0.035759 -0.031248 0.045171 0.086 Uiso 1 1 calc R . C15 C -0.0489(9) -0.0576(5) 0.1480(6) 0.090(3) Uani 1 1 d . . H15 H -0.118368 -0.094556 0.143810 0.108 Uiso 1 1 calc R . C16 C 0.0028(10) -0.0409(6) 0.2123(6) 0.091(3) Uani 1 1 d . . H16 H -0.032749 -0.065522 0.252082 0.110 Uiso 1 1 calc R . C17 C 0.1081(9) 0.0125(5) 0.2189(5) 0.074(2) Uani 1 1 d . . H17 H 0.143742 0.023156 0.263096 0.088 Uiso 1 1 calc R . C18 C 0.4480(7) 0.4316(4) 0.2953(3) 0.0532(18) Uani 1 1 d . . H18A H 0.361685 0.451848 0.310560 0.064 Uiso 1 1 calc R . H18B H 0.506645 0.477394 0.288026 0.064 Uiso 1 1 calc R . C19 C 0.5061(7) 0.3785(5) 0.3524(4) 0.0572(19) Uani 1 1 d . . H19 H 0.448251 0.331213 0.357667 0.069 Uiso 1 1 calc R . C20 C 0.5056(10) 0.4251(6) 0.4217(4) 0.094(3) Uani 1 1 d . . H20A H 0.533662 0.390134 0.459103 0.141 Uiso 1 1 calc GR . H20B H 0.416801 0.444437 0.431125 0.141 Uiso 1 1 calc GR . H20C H 0.566040 0.469889 0.418396 0.141 Uiso 1 1 calc GR . C21 C 0.6459(8) 0.3499(5) 0.3349(5) 0.082(3) Uani 1 1 d . . H21A H 0.645324 0.323647 0.289964 0.123 Uiso 1 1 calc GR . H21B H 0.675453 0.312625 0.370249 0.123 Uiso 1 1 calc GR . H21C H 0.705565 0.395171 0.333489 0.123 Uiso 1 1 calc GR . C22 C 0.3160(6) 0.5089(4) 0.1488(3) 0.0393(15) Uani 1 1 d . . C23 C 0.3193(7) 0.5830(4) 0.1836(3) 0.0441(17) Uani 1 1 d . . H23 H 0.394650 0.597571 0.209441 0.053 Uiso 1 1 calc R . C24 C 0.2130(7) 0.6338(4) 0.1800(4) 0.0516(19) Uani 1 1 d . . H24 H 0.217511 0.683332 0.202605 0.062 Uiso 1 1 calc R . C25 C 0.0980(7) 0.6136(4) 0.1434(3) 0.0475(17) Uani 1 1 d . . C26 C 0.0938(7) 0.5392(4) 0.1092(4) 0.0537(19) Uani 1 1 d . . H26 H 0.017200 0.524273 0.084647 0.064 Uiso 1 1 calc R . C27 C 0.2011(7) 0.4881(4) 0.1115(3) 0.0489(18) Uani 1 1 d . . H27 H 0.197383 0.439137 0.087876 0.059 Uiso 1 1 calc R . C28 C 0.6236(14) 0.6566(8) 0.0556(7) 0.152(5) Uani 1 1 d D U H28A H 0.529227 0.669753 0.059246 0.182 Uiso 1 1 calc R . H28B H 0.633476 0.610291 0.024948 0.182 Uiso 1 1 calc R . C29 C 0.7028(16) 0.7287(9) 0.0267(9) 0.214(7) Uani 1 1 d D U H29A H 0.706539 0.770319 0.061682 0.322 Uiso 1 1 calc GR . H29B H 0.659257 0.748926 -0.014635 0.322 Uiso 1 1 calc GR . H29C H 0.792059 0.711829 0.015100 0.322 Uiso 1 1 calc GR . N1 N 0.4312(5) 0.3882(3) 0.2281(3) 0.0415(13) Uani 1 1 d . . N2 N 0.1408(4) 0.2262(3) 0.1438(2) 0.0370(12) Uani 1 1 d . . H2A H 0.161828 0.228025 0.099996 0.044 Uiso 1 1 calc R . N3 N -0.0073(6) 0.6669(4) 0.1400(3) 0.0660(18) Uani 1 1 d . . H3A H -0.002774 0.707718 0.167777 0.079 Uiso 1 1 d R . H3B H -0.087024 0.650528 0.130547 0.079 Uiso 1 1 d R . O1 O 0.5708(4) 0.4879(3) 0.1656(3) 0.0571(13) Uani 1 1 d . . O2 O 0.4421(5) 0.3863(3) 0.0983(2) 0.0532(12) Uani 1 1 d . . O3 O 0.4507(4) 0.2112(3) 0.2501(2) 0.0539(12) Uani 1 1 d . . H3C H 0.412049 0.198327 0.286439 0.081 Uiso 1 1 calc GR . O4 O -0.0168(4) 0.2638(3) 0.2230(2) 0.0467(11) Uani 1 1 d . . O5 O -0.0534(4) 0.2702(3) 0.1058(2) 0.0451(11) Uani 1 1 d . . O6 O -0.2777(5) 0.2948(3) 0.0052(2) 0.0647(15) Uani 1 1 d . . O7 O -0.3505(5) 0.1639(3) 0.0192(3) 0.0686(15) Uani 1 1 d . . O8 O 0.6789(7) 0.6394(4) 0.1246(3) 0.0917(19) Uani 1 1 d . . H8 H 0.650898 0.595784 0.138407 0.138 Uiso 1 1 calc GR . S1 S 0.44914(17) 0.44147(10) 0.15586(9) 0.0446(4) Uani 1 1 d . . 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 C1 0.038(4) 0.040(4) 0.045(4) -0.001(3) -0.001(3) -0.003(3) C2 0.031(3) 0.039(4) 0.046(4) 0.006(3) -0.003(3) 0.006(3) C3 0.036(3) 0.034(4) 0.042(4) 0.005(3) 0.000(3) 0.001(3) C4 0.034(3) 0.035(4) 0.043(4) -0.005(3) -0.003(3) -0.004(3) C5 0.033(3) 0.059(5) 0.045(4) -0.001(4) 0.002(3) 0.015(3) C6 0.060(5) 0.052(5) 0.067(5) 0.002(4) -0.007(4) 0.007(4) C7 0.045(4) 0.076(6) 0.054(5) -0.006(5) -0.005(4) 0.011(4) C8 0.073(5) 0.059(5) 0.063(5) -0.004(4) -0.011(4) 0.008(4) C9 0.055(4) 0.067(5) 0.052(5) 0.003(4) -0.004(4) -0.011(4) C10 0.032(3) 0.072(5) 0.045(4) -0.002(4) 0.002(3) 0.002(4) C11 0.049(4) 0.036(4) 0.069(5) 0.000(4) -0.001(4) -0.001(3) C12 0.055(4) 0.027(3) 0.064(5) 0.004(4) 0.014(4) 0.005(3) C13 0.066(5) 0.049(5) 0.069(5) 0.000(4) 0.013(4) -0.009(4) C14 0.064(5) 0.067(6) 0.084(6) -0.020(5) 0.006(5) -0.012(5) C15 0.072(5) 0.063(5) 0.134(9) -0.021(6) 0.032(7) -0.023(5) C16 0.104(7) 0.077(7) 0.093(8) 0.005(6) 0.029(6) -0.037(6) C17 0.097(6) 0.052(5) 0.072(6) 0.001(5) 0.004(5) -0.008(5) C18 0.056(4) 0.049(4) 0.054(4) -0.008(4) 0.000(4) -0.006(4) C19 0.073(5) 0.053(5) 0.046(4) -0.001(4) -0.004(4) -0.002(4) C20 0.131(8) 0.097(8) 0.054(5) -0.020(5) -0.009(5) 0.003(6) C21 0.076(6) 0.080(6) 0.089(6) -0.005(5) -0.027(5) 0.010(5) C22 0.036(3) 0.040(4) 0.042(4) 0.004(3) 0.003(3) 0.002(3) C23 0.046(4) 0.039(4) 0.048(4) -0.001(3) 0.004(3) -0.005(3) C24 0.065(5) 0.033(4) 0.057(5) -0.008(3) 0.003(4) -0.005(4) C25 0.054(4) 0.048(4) 0.041(4) 0.007(4) 0.002(3) 0.005(4) C26 0.054(4) 0.062(5) 0.046(4) 0.002(4) -0.011(4) -0.002(4) C27 0.060(5) 0.044(4) 0.043(4) -0.008(3) -0.009(4) 0.007(4) C28 0.152(5) 0.152(5) 0.152(5) -0.0002(7) -0.0002(7) -0.0002(7) C29 0.215(7) 0.215(7) 0.214(7) 0.0002(14) 0.0002(14) 0.0007(14) N1 0.041(3) 0.041(3) 0.042(3) 0.003(3) -0.004(3) -0.004(3) N2 0.032(3) 0.045(3) 0.035(3) 0.001(3) 0.004(2) 0.003(2) N3 0.062(4) 0.068(4) 0.068(4) -0.004(4) -0.004(3) 0.014(3) O1 0.042(3) 0.048(3) 0.081(3) 0.006(3) 0.007(3) -0.008(2) O2 0.063(3) 0.049(3) 0.048(3) -0.007(2) 0.008(2) 0.004(3) O3 0.040(2) 0.048(3) 0.074(3) 0.004(3) -0.016(2) 0.006(2) O4 0.041(2) 0.061(3) 0.039(3) -0.003(2) 0.001(2) 0.011(2) O5 0.032(2) 0.065(3) 0.038(2) -0.004(2) 0.001(2) 0.011(2) O6 0.063(3) 0.081(4) 0.049(3) 0.000(3) -0.010(3) 0.012(3) O7 0.072(3) 0.072(4) 0.061(3) -0.014(3) -0.020(3) 0.006(3) O8 0.103(5) 0.089(5) 0.082(4) 0.011(4) -0.024(4) -0.028(4) S1 0.0417(9) 0.0399(9) 0.0523(10) -0.0006(9) 0.0012(8) -0.0007(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 H1A C1 H1B 107.7 C2 C1 H1A 108.9 C2 C1 H1B 108.9 N1 C1 H1A 108.9 N1 C1 H1B 108.9 N1 C1 C2 113.3(5) C1 C2 H2 107.7 C3 C2 C1 111.3(5) C3 C2 H2 107.7 O3 C2 C1 111.2(5) O3 C2 H2 107.7 O3 C2 C3 110.9(5) C2 C3 H3 108.2 C2 C3 C11 110.8(5) C11 C3 H3 108.2 N2 C3 C2 111.9(5) N2 C3 H3 108.2 N2 C3 C11 109.5(5) N2 C4 O5 108.8(5) O4 C4 N2 127.0(6) O4 C4 O5 124.1(5) C6 C5 H5 111.2 C10 C5 H5 111.2 C10 C5 C6 104.0(6) O5 C5 H5 111.2 O5 C5 C6 105.7(5) O5 C5 C10 113.1(5) C5 C6 H6A 110.9 C5 C6 H6B 110.9 H6A C6 H6B 109.0 O6 C6 C5 104.0(6) O6 C6 H6A 110.9 O6 C6 H6B 110.9 C10 C7 H7 110.6 O6 C7 H7 110.6 O6 C7 C10 106.2(6) O7 C7 H7 110.6 O7 C7 C10 108.9(6) O7 C7 O6 109.8(6) H8A C8 H8B 109.0 C9 C8 H8A 111.1 C9 C8 H8B 111.1 O7 C8 H8A 111.1 O7 C8 H8B 111.1 O7 C8 C9 103.5(6) C8 C9 H9A 111.1 C8 C9 H9B 111.1 H9A C9 H9B 109.1 C10 C9 C8 103.3(6) C10 C9 H9A 111.1 C10 C9 H9B 111.1 C5 C10 C7 105.0(6) C5 C10 H10 110.4 C7 C10 H10 110.4 C9 C10 C5 118.0(5) C9 C10 C7 102.3(6) C9 C10 H10 110.4 C3 C11 H11A 108.9 C3 C11 H11B 108.9 H11A C11 H11B 107.7 C12 C11 C3 113.3(5) C12 C11 H11A 108.9 C12 C11 H11B 108.9 C13 C12 C11 121.5(7) C13 C12 C17 118.5(7) C17 C12 C11 120.0(7) C12 C13 H13 119.5 C12 C13 C14 121.0(8) C14 C13 H13 119.5 C13 C14 H14 120.5 C15 C14 C13 119.1(8) C15 C14 H14 120.5 C14 C15 H15 119.7 C16 C15 C14 120.5(8) C16 C15 H15 119.7 C15 C16 H16 119.9 C15 C16 C17 120.1(9) C17 C16 H16 119.9 C12 C17 C16 120.7(8) C12 C17 H17 119.7 C16 C17 H17 119.7 H18A C18 H18B 107.8 C19 C18 H18A 109.1 C19 C18 H18B 109.1 N1 C18 H18A 109.1 N1 C18 H18B 109.1 N1 C18 C19 112.4(6) C18 C19 H19 108.3 C18 C19 C20 108.9(6) C20 C19 H19 108.3 C21 C19 C18 112.3(7) C21 C19 H19 108.3 C21 C19 C20 110.6(7) C19 C20 H20A 109.5 C19 C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C19 C21 H21A 109.5 C19 C21 H21B 109.5 C19 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C23 C22 S1 120.7(5) C27 C22 C23 118.7(6) C27 C22 S1 120.6(5) C22 C23 H23 119.9 C24 C23 C22 120.2(6) C24 C23 H23 119.9 C23 C24 H24 119.2 C23 C24 C25 121.7(6) C25 C24 H24 119.2 C24 C25 C26 118.2(6) N3 C25 C24 120.1(6) N3 C25 C26 121.6(7) C25 C26 H26 119.7 C27 C26 C25 120.7(6) C27 C26 H26 119.7 C22 C27 H27 119.7 C26 C27 C22 120.5(6) C26 C27 H27 119.7 H28A C28 H28B 108.7 C29 C28 H28A 110.5 C29 C28 H28B 110.5 O8 C28 H28A 110.5 O8 C28 H28B 110.5 O8 C28 C29 106.3(11) C28 C29 H29A 109.5 C28 C29 H29B 109.5 C28 C29 H29C 109.5 H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 C1 N1 S1 114.0(4) C18 N1 C1 115.0(5) C18 N1 S1 116.7(4) C3 N2 H2A 119.0 C4 N2 C3 122.0(5) C4 N2 H2A 119.0 C25 N3 H3A 116.0 C25 N3 H3B 120.8 H3A N3 H3B 115.3 C2 O3 H3C 109.5 C4 O5 C5 116.6(4) C7 O6 C6 108.0(5) C7 O7 C8 106.4(5) C28 O8 H8 109.5 N1 S1 C22 109.1(3) O1 S1 C22 107.9(3) O1 S1 N1 105.7(3) O2 S1 C22 108.4(3) O2 S1 N1 106.9(3) O2 S1 O1 118.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 H1A 0.9700 C1 H1B 0.9700 C1 C2 1.523(8) C1 N1 1.491(7) C2 H2 0.9800 C2 C3 1.515(8) C2 O3 1.427(7) C3 H3 0.9800 C3 C11 1.544(8) C3 N2 1.447(7) C4 N2 1.336(7) C4 O4 1.195(7) C4 O5 1.364(7) C5 H5 0.9800 C5 C6 1.525(9) C5 C10 1.517(9) C5 O5 1.447(7) C6 H6A 0.9700 C6 H6B 0.9700 C6 O6 1.437(8) C7 H7 0.9800 C7 C10 1.538(9) C7 O6 1.430(8) C7 O7 1.389(9) C8 H8A 0.9700 C8 H8B 0.9700 C8 C9 1.511(10) C8 O7 1.436(8) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.510(10) C10 H10 0.9800 C11 H11A 0.9700 C11 H11B 0.9700 C11 C12 1.516(9) C12 C13 1.374(10) C12 C17 1.375(10) C13 H13 0.9300 C13 C14 1.389(10) C14 H14 0.9300 C14 C15 1.371(12) C15 H15 0.9300 C15 C16 1.357(12) C16 H16 0.9300 C16 C17 1.382(11) C17 H17 0.9300 C18 H18A 0.9700 C18 H18B 0.9700 C18 C19 1.514(9) C18 N1 1.477(8) C19 H19 0.9800 C19 C20 1.529(10) C19 C21 1.511(11) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C22 C23 1.398(8) C22 C27 1.392(8) C22 S1 1.744(6) C23 H23 0.9300 C23 C24 1.357(9) C24 H24 0.9300 C24 C25 1.384(9) C25 C26 1.396(9) C25 N3 1.376(8) C26 H26 0.9300 C26 C27 1.367(9) C27 H27 0.9300 C28 H28A 0.9700 C28 H28B 0.9700 C28 C29 1.536(3) C28 O8 1.452(13) C29 H29A 0.9600 C29 H29B 0.9600 C29 H29C 0.9600 N1 S1 1.643(5) N2 H2A 0.8600 N3 H3A 0.8600 N3 H3B 0.8602 O1 S1 1.450(5) O2 S1 1.430(4) O3 H3C 0.8200 O8 H8 0.8200 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2A O6 0.86 2.13 2.970(7) 167.4 3 yes N3 H3A O4 0.86 2.29 3.073(8) 152.1 4 yes N3 H3B O8 0.86 2.35 3.179(9) 163.0 1_455 yes O3 H3C O8 0.82 2.16 2.963(9) 168.1 4_645 yes O8 H8 O1 0.82 2.03 2.847(7) 175.2 . yes 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 C1 C2 C3 C11 179.5(5) C1 C2 C3 N2 57.1(7) C1 N1 S1 C22 69.2(5) C1 N1 S1 O1 -175.1(4) C1 N1 S1 O2 -47.8(5) C2 C1 N1 C18 -127.3(6) C2 C1 N1 S1 94.0(6) C2 C3 C11 C12 178.3(6) C2 C3 N2 C4 -110.6(6) C3 C11 C12 C13 99.7(8) C3 C11 C12 C17 -80.7(8) C5 C6 O6 C7 36.7(7) C6 C5 C10 C7 16.0(7) C6 C5 C10 C9 129.0(6) C6 C5 O5 C4 152.9(5) C8 C9 C10 C5 -91.7(7) C8 C9 C10 C7 22.8(7) C9 C8 O7 C7 38.6(7) C10 C5 C6 O6 -31.8(7) C10 C5 O5 C4 -93.9(6) C10 C7 O6 C6 -26.4(7) C10 C7 O7 C8 -24.1(8) C11 C3 N2 C4 126.2(6) C11 C12 C13 C14 178.3(6) C11 C12 C17 C16 -179.0(7) C12 C13 C14 C15 0.6(12) C13 C12 C17 C16 0.6(11) C13 C14 C15 C16 0.8(14) C14 C15 C16 C17 -1.5(15) C15 C16 C17 C12 0.8(14) C17 C12 C13 C14 -1.3(11) C18 N1 S1 C22 -68.8(5) C18 N1 S1 O1 47.0(5) C18 N1 S1 O2 174.3(5) C19 C18 N1 C1 74.6(7) C19 C18 N1 S1 -147.9(5) C22 C23 C24 C25 1.4(10) C23 C22 C27 C26 -0.2(10) C23 C22 S1 N1 83.8(5) C23 C22 S1 O1 -30.5(6) C23 C22 S1 O2 -160.2(5) C23 C24 C25 C26 -0.6(10) C23 C24 C25 N3 -179.2(6) C24 C25 C26 C27 -0.5(10) C25 C26 C27 C22 0.9(10) C27 C22 C23 C24 -1.0(9) C27 C22 S1 N1 -92.6(6) C27 C22 S1 O1 153.1(5) C27 C22 S1 O2 23.4(6) N1 C1 C2 C3 -173.5(5) N1 C1 C2 O3 62.2(7) N1 C18 C19 C20 -173.8(7) N1 C18 C19 C21 63.4(8) N2 C3 C11 C12 -57.9(7) N2 C4 O5 C5 -177.7(5) N3 C25 C26 C27 178.0(6) O3 C2 C3 C11 -56.1(7) O3 C2 C3 N2 -178.5(5) O4 C4 N2 C3 8.5(9) O4 C4 O5 C5 3.0(9) O5 C4 N2 C3 -170.7(5) O5 C5 C6 O6 87.5(6) O5 C5 C10 C7 -98.1(6) O5 C5 C10 C9 14.9(8) O6 C7 C10 C5 5.3(7) O6 C7 C10 C9 -118.5(6) O6 C7 O7 C8 91.9(6) O7 C7 C10 C5 123.5(6) O7 C7 C10 C9 -0.2(7) O7 C7 O6 C6 -144.0(5) O7 C8 C9 C10 -37.8(7) S1 C22 C23 C24 -177.5(5) S1 C22 C27 C26 176.3(5)