#------------------------------------------------------------------------------ #$Date: 2024-08-05 22:38:29 +0300 (Mon, 05 Aug 2024) $ #$Revision: 293880 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571953.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_1571953 loop_ _publ_author_name 'Yan, Shen' 'Luan, Yuxuan' 'Xu, Hailiang' 'Fan, Hao' 'Martin, León' 'Gupta, Arvind Kumar' 'Linke, Heiner' 'Meyhofer, Edgar' 'Reddy, Pramod' 'Pauly, Fabian' 'Wärnmark, Kenneth' _publ_section_title ; How substituents tune quantum interference in meta-OPE3 molecular junctions to control thermoelectric transport. ; _journal_issue 29 _journal_name_full Nanoscale _journal_page_first 13905 _journal_page_last 13914 _journal_paper_doi 10.1039/d4nr02188f _journal_volume 16 _journal_year 2024 _chemical_formula_moiety 'C26 H17 N O4 S2' _chemical_formula_sum 'C26 H17 N O4 S2' _chemical_formula_weight 471.52 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-04-14 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2023-10-09 deposited with the CCDC. 2024-06-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.822(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7163(7) _cell_length_b 21.0713(9) _cell_length_c 10.6802(6) _cell_measurement_reflns_used 4113 _cell_measurement_temperature 293 _cell_measurement_theta_max 19.0630 _cell_measurement_theta_min 3.7970 _cell_volume 2353.0(3) _computing_cell_refinement 'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.903 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_unetI/netI 0.0869 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.903 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 48471 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.903 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.420 _diffrn_reflns_theta_min 3.494 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.331 _exptl_crystal_description plate _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.429 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 5887 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.2043 _refine_ls_R_factor_gt 0.0703 _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^)+(0.0973P)^2^+0.0079P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1802 _refine_ls_wR_factor_ref 0.2354 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2154 _reflns_number_total 5887 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4nr02188f2.cif _cod_data_source_block meta-OPE3_1 _cod_depositor_comments 'Adding full bibliography for 1571952--1571953.cif.' _cod_database_code 1571953 _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 0.970 _shelx_estimated_absorpt_t_min 0.931 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24) 3.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL AG_HX_97R1_a.res in P2(1)/c ag_hx_97r1_a.res created by SHELXL-2018/3 at 10:15:18 on 14-Apr-2021 REM Old TITL AG_HX_97R1 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.278, Rweak 0.121, Alpha 0.050, Orientation as input REM Formula found by SHELXT: C27 N O3 S2 CELL 0.71073 11.7163 21.0713 10.6802 90 116.822 90 ZERR 4 0.0007 0.0009 0.0006 0 0.008 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 104 68 4 16 8 ISOR 0.005 0.01 O2 O1 L.S. 20 PLAN 20 SIZE 0.28 0.2 0.12 TEMP 19.85 CONF BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.097300 0.007900 FVAR 0.36655 C1 1 0.036002 0.587793 -0.356398 11.00000 0.16696 0.08725 = 0.20121 0.02489 0.08516 0.01550 AFIX 137 H1A 2 0.099469 0.620642 -0.320657 11.00000 -1.50000 H1B 2 -0.034903 0.598671 -0.338577 11.00000 -1.50000 H1C 2 0.006882 0.583452 -0.455627 11.00000 -1.50000 AFIX 0 C2 1 0.094006 0.525300 -0.283945 11.00000 0.12017 0.08715 = 0.16094 -0.00915 0.08050 -0.01234 C3 1 0.128932 0.436350 -0.077745 11.00000 0.08269 0.09595 = 0.08789 -0.01707 0.03966 -0.00210 C4 1 0.107829 0.382558 -0.160669 11.00000 0.08436 0.09764 = 0.06670 -0.01148 0.02287 -0.00645 AFIX 43 H4 2 0.057100 0.385203 -0.257116 11.00000 -1.20000 AFIX 0 C5 1 0.161460 0.325647 -0.100906 11.00000 0.08234 0.09145 = 0.06529 -0.00925 0.02818 -0.00526 AFIX 43 H5 2 0.148079 0.290132 -0.157542 11.00000 -1.20000 AFIX 0 C6 1 0.235712 0.320348 0.043525 11.00000 0.06632 0.12244 = 0.05639 -0.00157 0.02843 -0.00700 C7 1 0.255055 0.374134 0.124282 11.00000 0.09140 0.14339 = 0.06383 -0.01688 0.03076 -0.01033 AFIX 43 H7 2 0.303591 0.371291 0.221062 11.00000 -1.20000 AFIX 0 C8 1 0.204591 0.431583 0.065521 11.00000 0.09056 0.12979 = 0.08317 -0.03483 0.03962 -0.00685 AFIX 43 H8 2 0.221181 0.467407 0.121931 11.00000 -1.20000 AFIX 0 C9 1 0.290778 0.260606 0.107380 11.00000 0.07426 0.12740 = 0.05627 0.01056 0.02661 -0.00601 C10 1 0.336210 0.211082 0.159186 11.00000 0.06838 0.12897 = 0.05790 0.00592 0.02667 -0.01293 C11 1 0.400009 0.155999 0.236104 11.00000 0.06863 0.10077 = 0.05873 0.00532 0.02691 -0.01713 C12 1 0.423999 0.100480 0.179053 11.00000 0.08573 0.10795 = 0.05607 -0.01113 0.03654 -0.03077 C13 1 0.494205 0.051176 0.261447 11.00000 0.11494 0.08919 = 0.08189 -0.01714 0.05673 -0.03007 AFIX 43 H13 2 0.508615 0.015233 0.220056 11.00000 -1.20000 AFIX 0 C14 1 0.543382 0.054553 0.404759 11.00000 0.10363 0.07658 = 0.07865 -0.00208 0.05115 -0.01418 AFIX 43 H14 2 0.591762 0.021225 0.460577 11.00000 -1.20000 AFIX 0 C15 1 0.520128 0.108709 0.466559 11.00000 0.07107 0.07954 = 0.05740 0.00369 0.03052 -0.01265 C16 1 0.450461 0.157828 0.382459 11.00000 0.06906 0.09049 = 0.05990 -0.00824 0.03458 -0.01649 AFIX 43 H16 2 0.436219 0.193682 0.424237 11.00000 -1.20000 AFIX 0 C17 1 0.567345 0.114482 0.615010 11.00000 0.07138 0.08005 = 0.06632 0.00223 0.03051 -0.00864 C18 1 0.602154 0.121746 0.738222 11.00000 0.07055 0.07252 = 0.06460 -0.00057 0.02759 -0.00632 C19 1 0.641848 0.130582 0.885315 11.00000 0.06760 0.07601 = 0.05556 0.00296 0.02498 -0.00698 C20 1 0.609018 0.185415 0.932934 11.00000 0.08784 0.08264 = 0.06176 0.00828 0.02733 0.01416 AFIX 43 H20 2 0.560889 0.216554 0.869262 11.00000 -1.20000 AFIX 0 C21 1 0.647264 0.194075 1.074078 11.00000 0.08625 0.08621 = 0.06940 0.00214 0.03346 0.01314 AFIX 43 H21 2 0.623648 0.230848 1.104629 11.00000 -1.20000 AFIX 0 C22 1 0.720060 0.148997 1.170695 11.00000 0.07155 0.08205 = 0.06376 0.01029 0.03119 -0.00599 C23 1 0.751678 0.094509 1.122543 11.00000 0.09072 0.07719 = 0.07328 0.02188 0.03113 -0.00038 AFIX 43 H23 2 0.800018 0.063463 1.186360 11.00000 -1.20000 AFIX 0 C24 1 0.713371 0.085159 0.982687 11.00000 0.08368 0.07380 = 0.07133 0.00422 0.03175 0.00247 AFIX 43 H24 2 0.735626 0.047845 0.952617 11.00000 -1.20000 AFIX 0 C25 1 0.868782 0.226784 1.392929 11.00000 0.08447 0.11539 = 0.06245 -0.00562 0.04102 0.00693 C26 1 0.937021 0.241156 1.545998 11.00000 0.10432 0.18091 = 0.05820 -0.02020 0.03266 0.00266 AFIX 137 H26A 2 1.014733 0.263624 1.566393 11.00000 -1.50000 H26B 2 0.956876 0.202223 1.598270 11.00000 -1.50000 H26C 2 0.883383 0.266873 1.571865 11.00000 -1.50000 AFIX 0 N1 3 0.371112 0.092918 0.027165 11.00000 0.13910 0.13049 = 0.07067 -0.00540 0.05083 -0.01415 O1 4 0.410007 0.052822 -0.020380 11.00000 0.26627 0.13739 = 0.09767 -0.02841 0.09065 -0.01866 O2 4 0.293166 0.127769 -0.045704 11.00000 0.24126 0.30959 = 0.07708 -0.01135 0.03362 0.09863 O3 4 0.154313 0.490558 -0.317761 11.00000 0.18493 0.11517 = 0.19143 0.01756 0.12899 0.01547 O4 4 0.878704 0.258122 1.305885 11.00000 0.15522 0.12268 = 0.07542 -0.01620 0.06073 -0.04107 S1 5 0.054583 0.509642 -0.145985 11.00000 0.11962 0.10499 = 0.14034 -0.02209 0.06591 0.00757 S2 5 0.771349 0.158003 1.352552 11.00000 0.10553 0.12900 = 0.06073 0.01290 0.04101 -0.01380 HKLF 4 REM AG_HX_97R1_a.res in P2(1)/c REM wR2 = 0.2354, GooF = S = 1.005, Restrained GooF = 1.055 for all data REM R1 = 0.0703 for 2154 Fo > 4sig(Fo) and 0.2043 for all 5887 data REM 300 parameters refined using 12 restraints END WGHT 0.0973 0.0079 REM Highest difference peak 0.429, deepest hole -0.247, 1-sigma level 0.038 Q1 1 0.3790 0.1574 -0.0397 11.00000 0.05 0.43 Q2 1 0.2846 0.0600 -0.0506 11.00000 0.05 0.29 Q3 1 0.2556 0.1171 -0.0331 11.00000 0.05 0.18 Q4 1 -0.0098 0.5567 -0.2270 11.00000 0.05 0.16 Q5 1 0.5763 0.1502 0.6812 11.00000 0.05 0.14 Q6 1 1.0355 0.2016 1.5797 11.00000 0.05 0.14 Q7 1 0.8165 0.2650 1.3014 11.00000 0.05 0.13 Q8 1 0.8844 0.2106 1.5923 11.00000 0.05 0.13 Q9 1 0.5893 0.0080 0.2448 11.00000 0.05 0.13 Q10 1 0.5655 -0.0125 0.2756 11.00000 0.05 0.13 Q11 1 0.2136 0.5009 -0.2431 11.00000 0.05 0.13 Q12 1 0.7094 0.1939 1.2945 11.00000 0.05 0.12 Q13 1 -0.0704 0.6001 -0.4408 11.00000 0.05 0.12 Q14 1 0.0979 0.5637 -0.1805 11.00000 0.05 0.12 Q15 1 0.6619 0.1589 0.9133 11.00000 0.05 0.12 Q16 1 0.7457 0.1286 1.1550 11.00000 0.05 0.12 Q17 1 0.5593 0.0949 0.6994 11.00000 0.05 0.12 Q18 1 0.0109 0.5020 -0.2794 11.00000 0.05 0.11 Q19 1 0.7701 0.2302 1.5283 11.00000 0.05 0.11 Q20 1 0.2541 0.2222 0.0851 11.00000 0.05 0.11 ; _shelx_res_checksum 71850 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0360(6) 0.5878(2) -0.3564(6) 0.151(2) Uani 1 1 d . . . . . H1A H 0.099469 0.620642 -0.320657 0.227 Uiso 1 1 calc R U . . . H1B H -0.034903 0.598671 -0.338577 0.227 Uiso 1 1 calc R U . . . H1C H 0.006882 0.583452 -0.455627 0.227 Uiso 1 1 calc R U . . . C2 C 0.0940(5) 0.5253(2) -0.2839(6) 0.1163(15) Uani 1 1 d . . . . . C3 C 0.1289(4) 0.43635(19) -0.0777(5) 0.0884(11) Uani 1 1 d . . . . . C4 C 0.1078(4) 0.3826(2) -0.1607(4) 0.0871(11) Uani 1 1 d . . . . . H4 H 0.057100 0.385203 -0.257116 0.105 Uiso 1 1 calc R U . . . C5 C 0.1615(3) 0.32565(19) -0.1009(4) 0.0816(11) Uani 1 1 d . . . . . H5 H 0.148079 0.290132 -0.157542 0.098 Uiso 1 1 calc R U . . . C6 C 0.2357(3) 0.3203(2) 0.0435(4) 0.0814(11) Uani 1 1 d . . . . . C7 C 0.2551(4) 0.3741(3) 0.1243(4) 0.1011(13) Uani 1 1 d . . . . . H7 H 0.303591 0.371291 0.221062 0.121 Uiso 1 1 calc R U . . . C8 C 0.2046(4) 0.4316(3) 0.0655(5) 0.1010(13) Uani 1 1 d . . . . . H8 H 0.221181 0.467407 0.121931 0.121 Uiso 1 1 calc R U . . . C9 C 0.2908(4) 0.2606(3) 0.1074(4) 0.0870(12) Uani 1 1 d . . . . . C10 C 0.3362(4) 0.2111(2) 0.1592(4) 0.0858(12) Uani 1 1 d . . . . . C11 C 0.4000(3) 0.1560(2) 0.2361(4) 0.0767(10) Uani 1 1 d . . . . . C12 C 0.4240(4) 0.1005(2) 0.1791(4) 0.0815(11) Uani 1 1 d . . . . . C13 C 0.4942(4) 0.0512(2) 0.2614(5) 0.0907(12) Uani 1 1 d . . . . . H13 H 0.508615 0.015233 0.220056 0.109 Uiso 1 1 calc R U . . . C14 C 0.5434(4) 0.05455(18) 0.4048(4) 0.0825(11) Uani 1 1 d . . . . . H14 H 0.591762 0.021225 0.460577 0.099 Uiso 1 1 calc R U . . . C15 C 0.5201(3) 0.10871(17) 0.4666(3) 0.0688(9) Uani 1 1 d . . . . . C16 C 0.4505(3) 0.15783(18) 0.3825(4) 0.0711(9) Uani 1 1 d . . . . . H16 H 0.436219 0.193682 0.424237 0.085 Uiso 1 1 calc R U . . . C17 C 0.5673(3) 0.11448(16) 0.6150(4) 0.0728(9) Uani 1 1 d . . . . . C18 C 0.6022(3) 0.12175(16) 0.7382(4) 0.0703(9) Uani 1 1 d . . . . . C19 C 0.6418(3) 0.13058(17) 0.8853(3) 0.0675(9) Uani 1 1 d . . . . . C20 C 0.6090(3) 0.18541(18) 0.9329(4) 0.0798(10) Uani 1 1 d . . . . . H20 H 0.560889 0.216554 0.869262 0.096 Uiso 1 1 calc R U . . . C21 C 0.6473(3) 0.19407(18) 1.0741(4) 0.0812(10) Uani 1 1 d . . . . . H21 H 0.623648 0.230848 1.104629 0.097 Uiso 1 1 calc R U . . . C22 C 0.7201(3) 0.14900(19) 1.1707(4) 0.0722(9) Uani 1 1 d . . . . . C23 C 0.7517(3) 0.09451(18) 1.1225(4) 0.0826(10) Uani 1 1 d . . . . . H23 H 0.800018 0.063463 1.186360 0.099 Uiso 1 1 calc R U . . . C24 C 0.7134(3) 0.08516(17) 0.9827(4) 0.0775(10) Uani 1 1 d . . . . . H24 H 0.735626 0.047845 0.952617 0.093 Uiso 1 1 calc R U . . . C25 C 0.8688(3) 0.2268(2) 1.3929(4) 0.0845(11) Uani 1 1 d . . . . . C26 C 0.9370(4) 0.2412(2) 1.5460(4) 0.1160(15) Uani 1 1 d . . . . . H26A H 1.014733 0.263624 1.566393 0.174 Uiso 1 1 calc R U . . . H26B H 0.956876 0.202223 1.598270 0.174 Uiso 1 1 calc R U . . . H26C H 0.883383 0.266873 1.571865 0.174 Uiso 1 1 calc R U . . . N1 N 0.3711(5) 0.0929(2) 0.0272(4) 0.1121(12) Uani 1 1 d . . . . . O1 O 0.4100(5) 0.05282(19) -0.0204(4) 0.1639(16) Uani 1 1 d . U . . . O2 O 0.2932(5) 0.1278(3) -0.0457(4) 0.224(3) Uani 1 1 d . U . . . O3 O 0.1543(4) 0.49056(17) -0.3178(4) 0.1472(13) Uani 1 1 d . . . . . O4 O 0.8787(3) 0.25812(15) 1.3059(3) 0.1145(10) Uani 1 1 d . . . . . S1 S 0.05458(12) 0.50964(6) -0.14598(14) 0.1189(5) Uani 1 1 d . . . . . S2 S 0.77135(10) 0.15800(6) 1.35255(10) 0.0971(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 0.167(5) 0.087(3) 0.201(6) 0.025(3) 0.085(4) 0.016(3) C2 0.120(4) 0.087(3) 0.161(5) -0.009(3) 0.081(3) -0.012(3) C3 0.083(3) 0.096(3) 0.088(3) -0.017(2) 0.040(2) -0.002(2) C4 0.084(3) 0.098(3) 0.067(2) -0.011(2) 0.0229(19) -0.006(2) C5 0.082(2) 0.091(3) 0.065(3) -0.009(2) 0.028(2) -0.005(2) C6 0.066(2) 0.122(3) 0.056(2) -0.002(2) 0.0284(19) -0.007(2) C7 0.091(3) 0.143(4) 0.064(3) -0.017(3) 0.031(2) -0.010(3) C8 0.091(3) 0.130(4) 0.083(3) -0.035(3) 0.040(3) -0.007(3) C9 0.074(3) 0.127(4) 0.056(2) 0.011(3) 0.027(2) -0.006(3) C10 0.068(2) 0.129(4) 0.058(2) 0.006(3) 0.0267(19) -0.013(3) C11 0.069(2) 0.101(3) 0.059(2) 0.005(2) 0.0269(18) -0.017(2) C12 0.086(3) 0.108(3) 0.056(2) -0.011(2) 0.037(2) -0.031(2) C13 0.115(3) 0.089(3) 0.082(3) -0.017(2) 0.057(3) -0.030(3) C14 0.104(3) 0.077(3) 0.079(3) -0.002(2) 0.051(2) -0.014(2) C15 0.071(2) 0.080(2) 0.057(2) 0.004(2) 0.0305(18) -0.0127(19) C16 0.069(2) 0.090(3) 0.060(2) -0.008(2) 0.0346(18) -0.0165(19) C17 0.071(2) 0.080(2) 0.066(2) 0.002(2) 0.0305(19) -0.0086(18) C18 0.071(2) 0.073(2) 0.065(2) -0.0006(19) 0.0276(18) -0.0063(17) C19 0.068(2) 0.076(2) 0.056(2) 0.0030(19) 0.0250(17) -0.0070(18) C20 0.088(2) 0.083(3) 0.062(2) 0.0083(19) 0.027(2) 0.014(2) C21 0.086(2) 0.086(3) 0.069(2) 0.002(2) 0.033(2) 0.013(2) C22 0.072(2) 0.082(3) 0.064(2) 0.010(2) 0.0312(18) -0.006(2) C23 0.091(3) 0.077(3) 0.073(3) 0.022(2) 0.031(2) 0.000(2) C24 0.084(2) 0.074(2) 0.071(3) 0.004(2) 0.032(2) 0.002(2) C25 0.084(2) 0.115(3) 0.062(2) -0.006(2) 0.041(2) 0.007(2) C26 0.104(3) 0.181(5) 0.058(2) -0.020(3) 0.033(2) 0.003(3) N1 0.139(3) 0.130(4) 0.071(3) -0.005(3) 0.051(3) -0.014(3) O1 0.266(5) 0.137(3) 0.098(3) -0.028(2) 0.091(3) -0.019(3) O2 0.241(5) 0.310(6) 0.077(3) -0.011(3) 0.034(3) 0.099(5) O3 0.185(3) 0.115(3) 0.191(4) 0.018(2) 0.129(3) 0.015(2) O4 0.155(3) 0.123(2) 0.0754(18) -0.0162(17) 0.0607(19) -0.0411(19) S1 0.1196(10) 0.1050(9) 0.1403(12) -0.0221(8) 0.0659(9) 0.0076(7) S2 0.1055(8) 0.1290(9) 0.0607(6) 0.0129(6) 0.0410(6) -0.0138(6) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C1 C2 S1 111.2(4) . . ? O3 C2 C1 124.9(5) . . ? O3 C2 S1 123.9(4) . . ? C4 C3 S1 122.6(3) . . ? C8 C3 C4 119.1(4) . . ? C8 C3 S1 118.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 119.6 . . ? C4 C5 C6 120.8(4) . . ? C6 C5 H5 119.6 . . ? C5 C6 C9 121.2(4) . . ? C7 C6 C5 118.1(4) . . ? C7 C6 C9 120.7(4) . . ? C6 C7 H7 119.2 . . ? C8 C7 C6 121.6(4) . . ? C8 C7 H7 119.2 . . ? C3 C8 H8 120.0 . . ? C7 C8 C3 120.0(4) . . ? C7 C8 H8 120.0 . . ? C10 C9 C6 179.5(4) . . ? C9 C10 C11 173.1(4) . . ? C12 C11 C10 125.8(3) . . ? C16 C11 C10 118.0(4) . . ? C16 C11 C12 116.2(4) . . ? C11 C12 N1 120.3(4) . . ? C13 C12 C11 122.2(3) . . ? C13 C12 N1 117.5(4) . . ? C12 C13 H13 119.8 . . ? C12 C13 C14 120.3(4) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 120.2 . . ? C13 C14 C15 119.5(4) . . ? C15 C14 H14 120.2 . . ? C14 C15 C17 122.0(3) . . ? C16 C15 C14 119.3(3) . . ? C16 C15 C17 118.7(3) . . ? C11 C16 H16 118.8 . . ? C15 C16 C11 122.5(3) . . ? C15 C16 H16 118.8 . . ? C18 C17 C15 176.5(4) . . ? C17 C18 C19 179.1(4) . . ? C20 C19 C18 120.2(3) . . ? C24 C19 C18 121.4(3) . . ? C24 C19 C20 118.4(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C20 C21 H21 119.5 . . ? C20 C21 C22 120.9(3) . . ? C22 C21 H21 119.5 . . ? C21 C22 S2 122.5(3) . . ? C23 C22 C21 118.4(3) . . ? C23 C22 S2 119.1(3) . . ? C22 C23 H23 119.4 . . ? C24 C23 C22 121.2(3) . . ? C24 C23 H23 119.4 . . ? C19 C24 H24 119.6 . . ? C23 C24 C19 120.7(3) . . ? C23 C24 H24 119.6 . . ? C26 C25 S2 113.6(3) . . ? O4 C25 C26 123.5(4) . . ? O4 C25 S2 122.9(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1 N1 C12 120.3(5) . . ? O2 N1 C12 119.2(5) . . ? O2 N1 O1 120.5(5) . . ? C3 S1 C2 104.1(2) . . ? C22 S2 C25 102.57(17) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 C2 1.523(7) . ? C2 O3 1.181(5) . ? C2 S1 1.763(6) . ? C3 C4 1.390(5) . ? C3 C8 1.383(5) . ? C3 S1 1.761(4) . ? C4 H4 0.9300 . ? C4 C5 1.371(5) . ? C5 H5 0.9300 . ? C5 C6 1.392(5) . ? C6 C7 1.380(6) . ? C6 C9 1.438(6) . ? C7 H7 0.9300 . ? C7 C8 1.369(6) . ? C8 H8 0.9300 . ? C9 C10 1.189(6) . ? C10 C11 1.424(6) . ? C11 C12 1.405(5) . ? C11 C16 1.400(4) . ? C12 C13 1.370(6) . ? C12 N1 1.461(5) . ? C13 H13 0.9300 . ? C13 C14 1.373(5) . ? C14 H14 0.9300 . ? C14 C15 1.405(5) . ? C15 C16 1.372(4) . ? C15 C17 1.429(5) . ? C16 H16 0.9300 . ? C17 C18 1.199(4) . ? C18 C19 1.435(4) . ? C19 C20 1.385(5) . ? C19 C24 1.383(5) . ? C20 H20 0.9300 . ? C20 C21 1.377(4) . ? C21 H21 0.9300 . ? C21 C22 1.378(5) . ? C22 C23 1.375(5) . ? C22 S2 1.765(4) . ? C23 H23 0.9300 . ? C23 C24 1.366(5) . ? C24 H24 0.9300 . ? C25 C26 1.491(5) . ? C25 O4 1.188(4) . ? C25 S2 1.774(4) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? N1 O1 1.178(5) . ? N1 O2 1.157(5) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 S1 C3 179.7(3) . . . . ? C3 C4 C5 C6 1.2(5) . . . . ? C4 C3 C8 C7 -1.6(6) . . . . ? C4 C3 S1 C2 -54.7(4) . . . . ? C4 C5 C6 C7 -0.8(5) . . . . ? C4 C5 C6 C9 179.1(3) . . . . ? C5 C6 C7 C8 -0.8(6) . . . . ? C6 C7 C8 C3 2.0(6) . . . . ? C8 C3 C4 C5 0.0(6) . . . . ? C8 C3 S1 C2 129.6(3) . . . . ? C9 C6 C7 C8 179.3(4) . . . . ? C10 C11 C12 C13 175.2(3) . . . . ? C10 C11 C12 N1 -6.4(5) . . . . ? C10 C11 C16 C15 -176.0(3) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? C11 C12 N1 O1 165.5(4) . . . . ? C11 C12 N1 O2 -12.5(7) . . . . ? C12 C11 C16 C15 0.4(5) . . . . ? C12 C13 C14 C15 0.7(5) . . . . ? C13 C12 N1 O1 -16.0(6) . . . . ? C13 C12 N1 O2 166.0(5) . . . . ? C13 C14 C15 C16 -1.2(5) . . . . ? C13 C14 C15 C17 179.1(3) . . . . ? C14 C15 C16 C11 0.6(5) . . . . ? C16 C11 C12 C13 -0.9(5) . . . . ? C16 C11 C12 N1 177.6(3) . . . . ? C17 C15 C16 C11 -179.6(3) . . . . ? C18 C19 C20 C21 -179.8(3) . . . . ? C18 C19 C24 C23 179.3(3) . . . . ? C19 C20 C21 C22 0.9(5) . . . . ? C20 C19 C24 C23 -0.6(5) . . . . ? C20 C21 C22 C23 -1.2(5) . . . . ? C20 C21 C22 S2 180.0(3) . . . . ? C21 C22 C23 C24 0.6(5) . . . . ? C21 C22 S2 C25 -62.1(3) . . . . ? C22 C23 C24 C19 0.3(5) . . . . ? C23 C22 S2 C25 119.1(3) . . . . ? C24 C19 C20 C21 0.1(5) . . . . ? C26 C25 S2 C22 -173.6(3) . . . . ? N1 C12 C13 C14 -178.1(3) . . . . ? O3 C2 S1 C3 1.9(6) . . . . ? O4 C25 S2 C22 6.2(4) . . . . ? S1 C3 C4 C5 -175.7(3) . . . . ? S1 C3 C8 C7 174.3(3) . . . . ? S2 C22 C23 C24 179.5(3) . . . . ?