#------------------------------------------------------------------------------ #$Date: 2019-11-29 20:36:01 +0200 (Fri, 29 Nov 2019) $ #$Revision: 244812 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239600.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_7239600 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, 2(H2 O)' _chemical_formula_sum 'C27 H41 N3 O9 S' _chemical_formula_weight 583.69 _chemical_name_common 'darunavir dihydrate' _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 dihydrate ; _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 2018-07-26 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-07-27 deposited with the CCDC. 2019-01-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9965(5) _cell_length_b 16.5620(10) _cell_length_c 18.7532(11) _cell_measurement_reflns_used 22461 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 58.814 _cell_measurement_theta_min 6.446 _cell_volume 3104.8(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 0.885 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_unetI/netI 0.0410 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.885 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 22461 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.875 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.407 _diffrn_reflns_theta_min 3.223 _diffrn_source 'rotating anode' _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_T_max 0.9398 _exptl_absorpt_correction_T_min 0.9284 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_description chunk _exptl_crystal_F_000 1248 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.283 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 364 _refine_ls_number_reflns 7509 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0478 _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^)+(0.0533P)^2^+0.6587P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1060 _refine_ls_wR_factor_ref 0.1225 _reflns_Friedel_coverage 0.779 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.863 _reflns_number_gt 5472 _reflns_number_total 7509 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ce02110d2.cif _cod_data_source_block dlnw _cod_database_code 7239600 _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 0.940 _shelx_estimated_absorpt_t_min 0.928 _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, All O(H,H) groups 2.a Riding coordinates: N2(H2A), N3(H3A,H3B), O1W(H1WA,H1WB), O2W(H2WA,H2WB) 2.b Ternary CH refined with riding coordinates: C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C19(H19) 2.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) 2.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) 2.e Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C21(H21A,H21B,H21C) 2.f Idealised tetrahedral OH refined as rotating group: O3(H3C) ; _shelx_res_file ; TITL dlnw in P 21 21 21 dlnw.res created by SHELXL-2018/3 at 16:25:16 on 26-Jul-2018 CELL 0.71073 9.9965 16.562 18.7532 90 90 90 ZERR 4 0.0005 0.001 0.0011 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 108 164 12 36 4 EQIV $1 -0.5+X,1.5-Y,-Z EQIV $2 2-X,-0.5+Y,0.5-Z EQIV $3 1-X,0.5+Y,0.5-Z L.S. 10 PLAN 3 SIZE 0.4 0.46 0.48 TEMP 23 HTAB N2 O6_$1 HTAB N3 O1W_$2 HTAB N3 O4_$2 HTAB O1W O1_$3 HTAB O1W O2W HTAB O3 O1W BOND $H CONF fmap 2 acta MERG 2 REM REM REM WGHT 0.053300 0.658700 FVAR 0.53328 C1 1 0.686167 0.678805 0.229591 11.00000 0.03712 0.04134 = 0.04619 0.00024 -0.00016 0.00161 AFIX 23 H1A 2 0.755102 0.658155 0.198087 11.00000 -1.20000 H1B 2 0.724639 0.683669 0.276882 11.00000 -1.20000 AFIX 0 C2 1 0.643868 0.762453 0.203818 11.00000 0.03090 0.03791 = 0.04876 -0.00348 0.00072 0.00379 AFIX 13 H2 2 0.600413 0.755891 0.157335 11.00000 -1.20000 AFIX 0 C3 1 0.764116 0.818096 0.193548 11.00000 0.03384 0.03638 = 0.04140 -0.00376 -0.00067 0.00200 AFIX 13 H3 2 0.808320 0.825192 0.239768 11.00000 -1.20000 AFIX 0 C4 1 0.978391 0.753652 0.164948 11.00000 0.03311 0.03511 = 0.03938 0.00083 0.00366 -0.00202 C5 1 1.183496 0.700309 0.120551 11.00000 0.03730 0.05460 = 0.04188 0.00587 0.00289 0.01054 AFIX 13 H5 2 1.183645 0.666817 0.163631 11.00000 -1.20000 AFIX 0 C6 1 1.217407 0.651348 0.054950 11.00000 0.05522 0.05911 = 0.05685 -0.00161 0.01058 0.01071 AFIX 23 H6A 2 1.279027 0.608113 0.066722 11.00000 -1.20000 H6B 2 1.137254 0.628066 0.034283 11.00000 -1.20000 AFIX 0 C7 1 1.357825 0.762534 0.047332 11.00000 0.03979 0.06872 = 0.04742 0.00501 0.00512 0.00584 AFIX 13 H7 2 1.451067 0.744420 0.049467 11.00000 -1.20000 AFIX 0 C8 1 1.241755 0.880374 0.053263 11.00000 0.07234 0.05647 = 0.06129 0.00329 0.00787 0.01014 AFIX 23 H8A 2 1.155832 0.865433 0.033174 11.00000 -1.20000 H8B 2 1.252657 0.938439 0.049803 11.00000 -1.20000 AFIX 0 C9 1 1.253804 0.852101 0.130143 11.00000 0.05948 0.06332 = 0.04391 -0.00603 0.00772 -0.01012 AFIX 23 H9A 2 1.321280 0.882787 0.155584 11.00000 -1.20000 H9B 2 1.169087 0.857054 0.154981 11.00000 -1.20000 AFIX 0 C10 1 1.294723 0.764155 0.122730 11.00000 0.03794 0.06564 = 0.03785 0.00834 0.00160 0.00446 AFIX 13 H10 2 1.361634 0.750068 0.158840 11.00000 -1.20000 AFIX 0 C11 1 0.720310 0.901301 0.166287 11.00000 0.04538 0.03646 = 0.07553 0.00399 -0.00095 0.00297 AFIX 23 H11A 2 0.673526 0.894602 0.121360 11.00000 -1.20000 H11B 2 0.658046 0.924724 0.200139 11.00000 -1.20000 AFIX 0 C12 1 0.835823 0.959027 0.155522 11.00000 0.05155 0.03138 = 0.06717 0.00157 -0.00625 -0.00001 C13 1 0.884871 0.975587 0.088455 11.00000 0.07332 0.05134 = 0.07425 -0.00043 -0.00713 -0.01555 AFIX 43 H13 2 0.847242 0.950161 0.049049 11.00000 -1.20000 AFIX 0 C14 1 0.989805 1.029731 0.078646 11.00000 0.08627 0.06939 = 0.08836 0.01062 0.00029 -0.02249 AFIX 43 H14 2 1.021308 1.040477 0.032959 11.00000 -1.20000 AFIX 0 C15 1 1.046133 1.066839 0.135792 11.00000 0.07524 0.06650 = 0.12542 0.01985 -0.02152 -0.02779 AFIX 43 H15 2 1.115352 1.103655 0.129408 11.00000 -1.20000 AFIX 0 C16 1 1.000004 1.049555 0.203278 11.00000 0.10583 0.07267 = 0.10435 -0.00645 -0.03875 -0.03424 AFIX 43 H16 2 1.039710 1.074023 0.242577 11.00000 -1.20000 AFIX 0 C17 1 0.895784 0.996466 0.213169 11.00000 0.09424 0.06094 = 0.07055 -0.00184 -0.01243 -0.01448 AFIX 43 H17 2 0.865373 0.985655 0.259053 11.00000 -1.20000 AFIX 0 C18 1 0.558702 0.577103 0.300921 11.00000 0.06205 0.04539 = 0.05184 0.00740 0.00379 -0.00385 AFIX 23 H18A 2 0.645481 0.557660 0.316438 11.00000 -1.20000 H18B 2 0.501085 0.530605 0.294153 11.00000 -1.20000 AFIX 0 C19 1 0.499631 0.630939 0.358699 11.00000 0.08081 0.05518 = 0.04678 0.00326 0.00965 -0.00836 AFIX 13 H19 2 0.557136 0.678442 0.364288 11.00000 -1.20000 AFIX 0 C20 1 0.499155 0.583871 0.428917 11.00000 0.14569 0.10244 = 0.05262 0.01138 0.00965 0.00065 AFIX 137 H20A 2 0.449940 0.534570 0.422876 11.00000 -1.50000 H20B 2 0.457741 0.615914 0.465419 11.00000 -1.50000 H20C 2 0.589484 0.571603 0.442507 11.00000 -1.50000 AFIX 0 C21 1 0.360038 0.659069 0.339881 11.00000 0.08586 0.08046 = 0.10180 0.01409 0.04176 0.00862 AFIX 137 H21A 2 0.360678 0.682968 0.293244 11.00000 -1.50000 H21B 2 0.330762 0.698303 0.374179 11.00000 -1.50000 H21C 2 0.300096 0.613784 0.340277 11.00000 -1.50000 AFIX 0 C22 1 0.690900 0.499496 0.152013 11.00000 0.04650 0.04051 = 0.04026 0.00138 0.00033 -0.00131 C23 1 0.685306 0.423548 0.184535 11.00000 0.04977 0.04263 = 0.04663 0.00383 0.00312 -0.00517 AFIX 43 H23 2 0.609506 0.408435 0.210001 11.00000 -1.20000 AFIX 0 C24 1 0.791394 0.371241 0.178972 11.00000 0.06163 0.04040 = 0.04979 0.00883 0.00078 -0.00052 AFIX 43 H24 2 0.786452 0.320833 0.200665 11.00000 -1.20000 AFIX 0 C25 1 0.906795 0.392577 0.141189 11.00000 0.05935 0.04922 = 0.04050 -0.00255 -0.00184 0.00894 C26 1 0.911844 0.468714 0.109664 11.00000 0.05206 0.05423 = 0.04159 0.00465 0.00786 0.00146 AFIX 43 H26 2 0.988205 0.484096 0.084806 11.00000 -1.20000 AFIX 0 C27 1 0.805377 0.521913 0.114629 11.00000 0.06061 0.04399 = 0.03888 0.00520 0.00631 -0.00274 AFIX 43 H27 2 0.810315 0.572402 0.093085 11.00000 -1.20000 AFIX 0 N1 3 0.574047 0.619892 0.232153 11.00000 0.04337 0.03881 = 0.04415 0.00337 0.00282 -0.00301 N2 3 0.859980 0.783035 0.143975 11.00000 0.03236 0.04467 = 0.03575 -0.00140 -0.00156 0.00222 AFIX 3 H2A 2 0.833730 0.785185 0.093385 11.00000 -1.20000 AFIX 0 N3 3 1.009512 0.337204 0.133266 11.00000 0.06693 0.06714 = 0.06506 0.00826 0.00855 0.01983 AFIX 3 H3A 2 1.084562 0.354774 0.125396 11.00000 -1.20000 H3B 2 1.014522 0.301234 0.166276 11.00000 -1.20000 AFIX 0 O1 4 0.436033 0.518739 0.169601 11.00000 0.04477 0.05386 = 0.07348 -0.00337 -0.00439 -0.00874 O2 4 0.561581 0.621117 0.101365 11.00000 0.06378 0.05230 = 0.04906 0.00576 -0.00535 0.00525 O1W 4 0.674272 0.863068 0.379397 11.00000 0.10965 0.10524 = 0.09204 0.00311 0.01059 0.03029 AFIX 3 H1WA 2 0.649662 0.910788 0.378607 11.00000 -1.50000 H1WB 2 0.648102 0.842918 0.417087 11.00000 -1.50000 AFIX 0 O3 4 0.5 ; 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 C1 C 0.6862(3) 0.67881(19) 0.22959(18) 0.0415(7) Uani 1 1 d . H1A H 0.755102 0.658155 0.198087 0.050 Uiso 1 1 calc R H1B H 0.724639 0.683669 0.276882 0.050 Uiso 1 1 calc R C2 C 0.6439(3) 0.76245(19) 0.20382(17) 0.0392(7) Uani 1 1 d . H2 H 0.600413 0.755891 0.157335 0.047 Uiso 1 1 calc R C3 C 0.7641(3) 0.81810(18) 0.19355(16) 0.0372(7) Uani 1 1 d . H3 H 0.808320 0.825192 0.239768 0.045 Uiso 1 1 calc R C4 C 0.9784(3) 0.75365(18) 0.16495(16) 0.0359(6) Uani 1 1 d . C5 C 1.1835(3) 0.7003(2) 0.12055(17) 0.0446(8) Uani 1 1 d . H5 H 1.183645 0.666817 0.163631 0.054 Uiso 1 1 calc R C6 C 1.2174(4) 0.6513(3) 0.0549(2) 0.0571(9) Uani 1 1 d . H6A H 1.279027 0.608113 0.066722 0.068 Uiso 1 1 calc R H6B H 1.137254 0.628066 0.034283 0.068 Uiso 1 1 calc R C7 C 1.3578(3) 0.7625(2) 0.04733(18) 0.0520(9) Uani 1 1 d . H7 H 1.451067 0.744420 0.049467 0.062 Uiso 1 1 calc R C8 C 1.2418(4) 0.8804(3) 0.0533(2) 0.0634(10) Uani 1 1 d . H8A H 1.155832 0.865433 0.033174 0.076 Uiso 1 1 calc R H8B H 1.252657 0.938439 0.049803 0.076 Uiso 1 1 calc R C9 C 1.2538(4) 0.8521(2) 0.13014(19) 0.0556(9) Uani 1 1 d . H9A H 1.321280 0.882787 0.155584 0.067 Uiso 1 1 calc R H9B H 1.169087 0.857054 0.154981 0.067 Uiso 1 1 calc R C10 C 1.2947(3) 0.7642(2) 0.12273(17) 0.0471(8) Uani 1 1 d . H10 H 1.361634 0.750068 0.158840 0.057 Uiso 1 1 calc R C11 C 0.7203(3) 0.9013(2) 0.1663(2) 0.0525(8) Uani 1 1 d . H11A H 0.673526 0.894602 0.121360 0.063 Uiso 1 1 calc R H11B H 0.658046 0.924724 0.200139 0.063 Uiso 1 1 calc R C12 C 0.8358(3) 0.95903(19) 0.1555(2) 0.0500(8) Uani 1 1 d . C13 C 0.8849(4) 0.9756(3) 0.0885(2) 0.0663(11) Uani 1 1 d . H13 H 0.847242 0.950161 0.049049 0.080 Uiso 1 1 calc R C14 C 0.9898(5) 1.0297(3) 0.0786(3) 0.0813(14) Uani 1 1 d . H14 H 1.021308 1.040477 0.032959 0.098 Uiso 1 1 calc R C15 C 1.0461(5) 1.0668(3) 0.1358(3) 0.0891(15) Uani 1 1 d . H15 H 1.115352 1.103655 0.129408 0.107 Uiso 1 1 calc R C16 C 1.0000(5) 1.0496(3) 0.2033(3) 0.0943(17) Uani 1 1 d . H16 H 1.039710 1.074023 0.242577 0.113 Uiso 1 1 calc R C17 C 0.8958(5) 0.9965(3) 0.2132(2) 0.0752(12) Uani 1 1 d . H17 H 0.865373 0.985655 0.259053 0.090 Uiso 1 1 calc R C18 C 0.5587(4) 0.5771(2) 0.30092(18) 0.0531(8) Uani 1 1 d . H18A H 0.645481 0.557660 0.316438 0.064 Uiso 1 1 calc R H18B H 0.501085 0.530605 0.294153 0.064 Uiso 1 1 calc R C19 C 0.4996(4) 0.6309(3) 0.35870(19) 0.0609(10) Uani 1 1 d . H19 H 0.557136 0.678442 0.364288 0.073 Uiso 1 1 calc R C20 C 0.4992(7) 0.5839(4) 0.4289(2) 0.1002(18) Uani 1 1 d . H20A H 0.449940 0.534570 0.422876 0.150 Uiso 1 1 calc GR H20B H 0.457741 0.615914 0.465419 0.150 Uiso 1 1 calc GR H20C H 0.589484 0.571603 0.442507 0.150 Uiso 1 1 calc GR C21 C 0.3600(5) 0.6591(3) 0.3399(3) 0.0894(15) Uani 1 1 d . H21A H 0.360678 0.682968 0.293244 0.134 Uiso 1 1 calc GR H21B H 0.330762 0.698303 0.374179 0.134 Uiso 1 1 calc GR H21C H 0.300096 0.613784 0.340277 0.134 Uiso 1 1 calc GR C22 C 0.6909(3) 0.4995(2) 0.15201(17) 0.0424(7) Uani 1 1 d . C23 C 0.6853(3) 0.4235(2) 0.18453(17) 0.0463(8) Uani 1 1 d . H23 H 0.609506 0.408435 0.210001 0.056 Uiso 1 1 calc R C24 C 0.7914(4) 0.3712(2) 0.17897(18) 0.0506(8) Uani 1 1 d . H24 H 0.786452 0.320833 0.200665 0.061 Uiso 1 1 calc R C25 C 0.9068(4) 0.3926(2) 0.14119(17) 0.0497(8) Uani 1 1 d . C26 C 0.9118(3) 0.4687(2) 0.10966(17) 0.0493(8) Uani 1 1 d . H26 H 0.988205 0.484096 0.084806 0.059 Uiso 1 1 calc R C27 C 0.8054(3) 0.5219(2) 0.11463(17) 0.0478(8) Uani 1 1 d . H27 H 0.810315 0.572402 0.093085 0.057 Uiso 1 1 calc R N1 N 0.5740(3) 0.61989(16) 0.23215(14) 0.0421(6) Uani 1 1 d . N2 N 0.8600(2) 0.78303(16) 0.14398(13) 0.0376(6) Uani 1 1 d . H2A H 0.833730 0.785185 0.093385 0.045 Uiso 1 1 d R N3 N 1.0095(3) 0.3372(2) 0.13327(18) 0.0664(9) Uani 1 1 d . H3A H 1.084562 0.354774 0.125396 0.080 Uiso 1 1 d R H3B H 1.014522 0.301234 0.166276 0.080 Uiso 1 1 d R O1 O 0.4360(2) 0.51874(15) 0.16960(14) 0.0574(6) Uani 1 1 d . O2 O 0.5616(3) 0.62112(15) 0.10136(12) 0.0550(6) Uani 1 1 d . O1W O 0.6743(4) 0.8631(2) 0.37940(19) 0.1023(12) Uani 1 1 d . H1WA H 0.649662 0.910788 0.378607 0.153 Uiso 1 1 d R H1WB H 0.648102 0.842918 0.417087 0.153 Uiso 1 1 d R O3 O 0.5498(2) 0.79793(15) 0.25064(13) 0.0549(6) Uani 1 1 d . H3C H 0.587674 0.812013 0.287387 0.082 Uiso 1 1 calc GR O2W O 0.5989(13) 0.7852(4) 0.5112(3) 0.282(6) Uani 1 1 d . H2WA H 0.661889 0.753653 0.503529 0.422 Uiso 1 1 d R H2WB H 0.526799 0.797633 0.493319 0.422 Uiso 1 1 d R O4 O 1.0146(2) 0.74417(15) 0.22605(11) 0.0457(5) Uani 1 1 d . O5 O 1.05338(19) 0.73494(14) 0.10744(10) 0.0441(5) Uani 1 1 d . O6 O 1.2778(3) 0.70701(18) 0.00672(13) 0.0621(7) Uani 1 1 d . O7 O 1.3492(3) 0.83879(18) 0.01784(14) 0.0663(8) Uani 1 1 d . S1 S 0.55557(8) 0.56597(5) 0.15967(4) 0.0438(2) 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 0.0371(16) 0.0413(19) 0.0462(17) 0.0002(14) -0.0002(13) 0.0016(13) C2 0.0309(14) 0.0379(17) 0.0488(17) -0.0035(14) 0.0007(11) 0.0038(12) C3 0.0338(15) 0.0364(17) 0.0414(16) -0.0038(13) -0.0007(12) 0.0020(12) C4 0.0331(14) 0.0351(16) 0.0394(16) 0.0008(14) 0.0037(11) -0.0020(11) C5 0.0373(16) 0.055(2) 0.0419(17) 0.0059(16) 0.0029(13) 0.0105(14) C6 0.055(2) 0.059(2) 0.057(2) -0.0016(18) 0.0106(16) 0.0107(18) C7 0.0398(17) 0.069(3) 0.0474(19) 0.0050(18) 0.0051(13) 0.0058(17) C8 0.072(3) 0.056(2) 0.061(2) 0.0033(19) 0.0079(19) 0.010(2) C9 0.059(2) 0.063(2) 0.0439(19) -0.0060(17) 0.0077(15) -0.0101(18) C10 0.0379(16) 0.066(2) 0.0379(17) 0.0083(16) 0.0016(12) 0.0045(16) C11 0.0454(18) 0.0365(17) 0.076(2) 0.0040(18) -0.0010(17) 0.0030(14) C12 0.0516(19) 0.0314(17) 0.067(2) 0.0016(17) -0.0062(17) 0.0000(13) C13 0.073(3) 0.051(2) 0.074(3) 0.000(2) -0.007(2) -0.016(2) C14 0.086(3) 0.069(3) 0.088(3) 0.011(3) 0.000(2) -0.022(3) C15 0.075(3) 0.066(3) 0.125(4) 0.020(3) -0.022(3) -0.028(3) C16 0.106(4) 0.073(4) 0.104(4) -0.006(3) -0.039(3) -0.034(3) C17 0.094(3) 0.061(3) 0.071(3) -0.002(2) -0.012(2) -0.014(2) C18 0.062(2) 0.045(2) 0.052(2) 0.0074(16) 0.0038(16) -0.0039(18) C19 0.081(3) 0.055(2) 0.047(2) 0.0033(17) 0.0097(17) -0.008(2) C20 0.146(5) 0.102(4) 0.053(3) 0.011(3) 0.010(3) 0.001(4) C21 0.086(3) 0.080(3) 0.102(4) 0.014(3) 0.042(3) 0.009(3) C22 0.0465(17) 0.0405(18) 0.0403(17) 0.0014(14) 0.0003(13) -0.0013(14) C23 0.0498(18) 0.043(2) 0.0466(18) 0.0038(15) 0.0031(13) -0.0052(15) C24 0.062(2) 0.0404(19) 0.050(2) 0.0088(15) 0.0008(15) -0.0005(16) C25 0.059(2) 0.049(2) 0.0405(18) -0.0025(15) -0.0018(14) 0.0089(16) C26 0.052(2) 0.054(2) 0.0416(18) 0.0047(16) 0.0079(14) 0.0015(16) C27 0.061(2) 0.044(2) 0.0389(18) 0.0052(15) 0.0063(14) -0.0027(16) N1 0.0434(14) 0.0388(15) 0.0442(14) 0.0034(12) 0.0028(11) -0.0030(12) N2 0.0324(12) 0.0447(16) 0.0357(13) -0.0014(11) -0.0016(9) 0.0022(10) N3 0.067(2) 0.067(2) 0.065(2) 0.0083(17) 0.0086(15) 0.0198(17) O1 0.0448(13) 0.0539(15) 0.0735(16) -0.0034(13) -0.0044(12) -0.0087(11) O2 0.0638(15) 0.0523(15) 0.0491(13) 0.0058(11) -0.0054(12) 0.0053(12) O1W 0.110(3) 0.105(3) 0.092(2) 0.003(2) 0.011(2) 0.030(2) O3 0.0427(12) 0.0512(15) 0.0708(17) -0.0062(13) 0.0144(11) 0.0074(11) O2W 0.519(18) 0.168(7) 0.158(6) 0.010(5) 0.002(8) -0.043(9) O4 0.0428(11) 0.0583(15) 0.0362(12) 0.0026(11) -0.0014(8) 0.0094(10) O5 0.0314(10) 0.0644(15) 0.0364(11) -0.0007(10) 0.0015(8) 0.0078(10) O6 0.0643(16) 0.0776(19) 0.0444(14) -0.0032(13) 0.0124(11) 0.0057(14) O7 0.0734(18) 0.0697(19) 0.0559(16) 0.0172(14) 0.0210(13) 0.0103(14) S1 0.0431(4) 0.0416(4) 0.0467(4) 0.0022(4) -0.0027(3) -0.0013(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 113.4(2) C1 C2 H2 107.7 C3 C2 C1 111.7(2) C3 C2 H2 107.7 O3 C2 C1 111.4(3) O3 C2 H2 107.7 O3 C2 C3 110.5(2) C2 C3 H3 108.4 C2 C3 C11 111.1(2) C11 C3 H3 108.4 N2 C3 C2 111.0(2) N2 C3 H3 108.4 N2 C3 C11 109.5(3) N2 C4 O5 109.9(2) O4 C4 N2 126.1(3) O4 C4 O5 124.1(2) C6 C5 H5 111.5 C6 C5 C10 103.2(3) C10 C5 H5 111.5 O5 C5 H5 111.5 O5 C5 C6 106.1(3) O5 C5 C10 112.6(3) C5 C6 H6A 110.7 C5 C6 H6B 110.7 H6A C6 H6B 108.8 O6 C6 C5 105.3(3) O6 C6 H6A 110.7 O6 C6 H6B 110.7 C10 C7 H7 110.8 O6 C7 H7 110.8 O6 C7 C10 105.5(3) O7 C7 H7 110.8 O7 C7 C10 108.9(3) O7 C7 O6 109.8(3) H8A C8 H8B 109.1 C9 C8 H8A 111.1 C9 C8 H8B 111.1 O7 C8 H8A 111.1 O7 C8 H8B 111.1 O7 C8 C9 103.4(3) C8 C9 H9A 111.1 C8 C9 H9B 111.1 H9A C9 H9B 109.1 C10 C9 C8 103.3(3) C10 C9 H9A 111.1 C10 C9 H9B 111.1 C5 C10 C7 105.0(3) C5 C10 H10 110.4 C7 C10 H10 110.4 C9 C10 C5 117.9(3) C9 C10 C7 102.1(3) C9 C10 H10 110.4 C3 C11 H11A 108.9 C3 C11 H11B 108.9 H11A C11 H11B 107.7 C12 C11 C3 113.2(3) C12 C11 H11A 108.9 C12 C11 H11B 108.9 C13 C12 C11 121.3(3) C13 C12 C17 118.0(4) C17 C12 C11 120.7(4) C12 C13 H13 119.4 C12 C13 C14 121.1(4) C14 C13 H13 119.4 C13 C14 H14 120.0 C15 C14 C13 120.0(5) C15 C14 H14 120.0 C14 C15 H15 120.2 C14 C15 C16 119.5(4) C16 C15 H15 120.2 C15 C16 H16 119.7 C17 C16 C15 120.7(5) C17 C16 H16 119.7 C12 C17 H17 119.7 C16 C17 C12 120.6(4) C16 C17 H17 119.7 H18A C18 H18B 107.9 C19 C18 H18A 109.1 C19 C18 H18B 109.1 N1 C18 H18A 109.1 N1 C18 H18B 109.1 N1 C18 C19 112.3(3) C18 C19 H19 108.6 C18 C19 C20 108.4(4) C20 C19 H19 108.6 C21 C19 C18 111.8(4) C21 C19 H19 108.6 C21 C19 C20 110.8(4) 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 119.9(2) C27 C22 C23 119.5(3) C27 C22 S1 120.6(3) C22 C23 H23 119.9 C24 C23 C22 120.2(3) C24 C23 H23 119.9 C23 C24 H24 119.5 C23 C24 C25 121.1(3) C25 C24 H24 119.5 C26 C25 C24 118.2(3) N3 C25 C24 119.9(3) N3 C25 C26 121.8(3) C25 C26 H26 119.4 C27 C26 C25 121.3(3) C27 C26 H26 119.4 C22 C27 H27 120.1 C26 C27 C22 119.7(3) C26 C27 H27 120.1 C1 N1 S1 114.6(2) C18 N1 C1 114.9(3) C18 N1 S1 116.8(2) C3 N2 H2A 115.2 C4 N2 C3 122.6(3) C4 N2 H2A 122.1 C25 N3 H3A 117.6 C25 N3 H3B 115.1 H3A N3 H3B 108.8 H1WA O1W H1WB 107.9 C2 O3 H3C 109.5 H2WA O2W H2WB 138.9 C4 O5 C5 117.1(2) C6 O6 C7 108.2(3) C7 O7 C8 107.4(3) N1 S1 C22 108.91(15) O1 S1 C22 108.07(15) O1 S1 N1 106.41(14) O2 S1 C22 107.91(15) O2 S1 N1 106.41(14) O2 S1 O1 118.82(15) 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 1.527(4) C1 N1 1.487(4) C2 H2 0.9800 C2 C3 1.527(4) C2 O3 1.414(4) C3 H3 0.9800 C3 C11 1.534(4) C3 N2 1.456(4) C4 N2 1.339(4) C4 O4 1.212(3) C4 O5 1.349(3) C5 H5 0.9800 C5 C6 1.512(5) C5 C10 1.535(5) C5 O5 1.443(4) C6 H6A 0.9700 C6 H6B 0.9700 C6 O6 1.425(5) C7 H7 0.9800 C7 C10 1.549(4) C7 O6 1.438(5) C7 O7 1.381(5) C8 H8A 0.9700 C8 H8B 0.9700 C8 C9 1.521(5) C8 O7 1.439(5) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.519(5) C10 H10 0.9800 C11 H11A 0.9700 C11 H11B 0.9700 C11 C12 1.513(5) C12 C13 1.377(6) C12 C17 1.383(5) C13 H13 0.9300 C13 C14 1.392(6) C14 H14 0.9300 C14 C15 1.358(7) C15 H15 0.9300 C15 C16 1.377(7) C16 H16 0.9300 C16 C17 1.376(6) C17 H17 0.9300 C18 H18A 0.9700 C18 H18B 0.9700 C18 C19 1.522(5) C18 N1 1.479(4) C19 H19 0.9800 C19 C20 1.530(6) C19 C21 1.513(6) 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 1.399(5) C22 C27 1.392(4) C22 S1 1.750(3) C23 H23 0.9300 C23 C24 1.373(5) C24 H24 0.9300 C24 C25 1.399(5) C25 C26 1.394(5) C25 N3 1.385(4) C26 H26 0.9300 C26 C27 1.385(5) C27 H27 0.9300 N1 S1 1.637(3) N2 H2A 0.9850 N3 H3A 0.8181 N3 H3B 0.8606 O1 S1 1.440(2) O2 S1 1.426(2) O1W H1WA 0.8279 O1W H1WB 0.8242 O3 H3C 0.8200 O2W H2WA 0.8302 O2W H2WB 0.8210 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 0.98 1.96 2.948(3) 178.0 3_465 yes N3 H3A O1W 0.82 2.42 3.199(5) 160.4 4_745 yes N3 H3B O4 0.86 2.25 3.065(4) 158.4 4_745 yes O1W H1WA O1 0.83 2.18 2.951(5) 155.2 4_655 yes O1W H1WB O2W 0.82 2.07 2.888(8) 174.4 . yes O3 H3C O1W 0.82 2.11 2.923(5) 172.6 . 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 178.9(3) C1 C2 C3 N2 56.9(3) C1 N1 S1 C22 69.1(2) C1 N1 S1 O1 -174.7(2) C1 N1 S1 O2 -47.0(2) C2 C1 N1 C18 -128.2(3) C2 C1 N1 S1 92.4(3) C2 C3 C11 C12 179.7(3) C2 C3 N2 C4 -108.3(3) C3 C11 C12 C13 103.0(4) C3 C11 C12 C17 -76.6(4) C5 C6 O6 C7 36.9(4) C6 C5 C10 C7 16.2(3) C6 C5 C10 C9 129.0(3) C6 C5 O5 C4 154.5(3) C8 C9 C10 C5 -91.5(3) C8 C9 C10 C7 22.9(3) C9 C8 O7 C7 37.6(4) C10 C5 C6 O6 -32.1(3) C10 C5 O5 C4 -93.3(3) C10 C7 O6 C6 -25.7(4) C10 C7 O7 C8 -22.9(4) C11 C3 N2 C4 128.8(3) C11 C12 C13 C14 179.0(4) C11 C12 C17 C16 -179.4(4) C12 C13 C14 C15 0.4(7) C13 C12 C17 C16 1.0(6) C13 C14 C15 C16 1.0(8) C14 C15 C16 C17 -1.4(8) C15 C16 C17 C12 0.4(8) C17 C12 C13 C14 -1.4(6) C18 N1 S1 C22 -69.5(3) C18 N1 S1 O1 46.8(3) C18 N1 S1 O2 174.4(2) C19 C18 N1 C1 74.2(4) C19 C18 N1 S1 -147.4(3) C22 C23 C24 C25 0.2(5) C23 C22 C27 C26 0.4(5) C23 C22 S1 N1 88.0(3) C23 C22 S1 O1 -27.2(3) C23 C22 S1 O2 -156.9(3) C23 C24 C25 C26 0.5(5) C23 C24 C25 N3 -176.7(3) C24 C25 C26 C27 -0.7(5) C25 C26 C27 C22 0.3(5) C27 C22 C23 C24 -0.7(5) C27 C22 S1 N1 -91.1(3) C27 C22 S1 O1 153.7(3) C27 C22 S1 O2 24.1(3) N1 C1 C2 C3 -173.3(2) N1 C1 C2 O3 62.6(3) N1 C18 C19 C20 -175.1(4) N1 C18 C19 C21 62.5(4) N2 C3 C11 C12 -57.4(4) N2 C4 O5 C5 -178.4(3) N3 C25 C26 C27 176.4(3) O3 C2 C3 C11 -56.5(4) O3 C2 C3 N2 -178.5(2) O4 C4 N2 C3 8.5(5) O4 C4 O5 C5 1.1(4) O5 C4 N2 C3 -172.0(3) O5 C5 C6 O6 86.5(3) O5 C5 C10 C7 -97.7(3) O5 C5 C10 C9 15.1(4) O6 C7 C10 C5 4.6(3) O6 C7 C10 C9 -118.9(3) O6 C7 O7 C8 92.2(3) O7 C7 C10 C5 122.4(3) O7 C7 C10 C9 -1.1(4) O7 C7 O6 C6 -142.9(3) O7 C8 C9 C10 -37.1(4) S1 C22 C23 C24 -179.7(3) S1 C22 C27 C26 179.5(3)