#------------------------------------------------------------------------------ #$Date: 2024-06-21 03:11:35 +0300 (Fri, 21 Jun 2024) $ #$Revision: 292491 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571952.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_1571952 loop_ _publ_author_name 'W\"arnmark, Kenneth' 'Shen, Yan' 'Luan, Yuxuan' 'Xu, Hailiang' 'Fan, Hao' 'Martin, Leon' 'Gupta, Arvind Kumar' 'Linke, Heiner' 'Meyhofer, Edgar' 'Reddy, Pramod' 'Pauly, Fabian' _publ_section_title ; How Substituents Tune Quantum Interference in meta-OPE3 Molecular Junctions to Control Thermoelectric Transport ; _journal_name_full Nanoscale _journal_paper_doi 10.1039/D4NR02188F _journal_year 2024 _chemical_formula_moiety 'C28 H23 N O2 S2' _chemical_formula_sum 'C28 H23 N O2 S2' _chemical_formula_weight 469.59 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2021-03-23 _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 75.237(7) _cell_angle_beta 82.715(7) _cell_angle_gamma 71.385(8) _cell_formula_units_Z 2 _cell_length_a 8.6676(8) _cell_length_b 10.3090(8) _cell_length_c 15.1742(13) _cell_measurement_reflns_used 1652 _cell_measurement_temperature 295 _cell_measurement_theta_max 21.8730 _cell_measurement_theta_min 3.6180 _cell_volume 1241.0(2) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _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 295 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_unetI/netI 0.1052 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 12068 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.500 _diffrn_reflns_theta_min 3.347 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.257 _exptl_crystal_description block _exptl_crystal_F_000 492 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.176 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 5061 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.981 _refine_ls_R_factor_all 0.1609 _refine_ls_R_factor_gt 0.0584 _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^)+(0.0375P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.1383 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2156 _reflns_number_total 5061 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4nr02188f2.cif _cod_data_source_block ag_hx_24r1_a _cod_database_code 1571952 _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 0.963 _shelx_estimated_absorpt_t_min 0.919 _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.a Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C14(H14), C16(H16), C22(H22), C23(H23), C25(H25), C26(H26) 2.b Idealised Me refined as rotating group: C2(H2A,H2B,H2C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C28(H28A,H28B,H28C) ; _smtbx_masks_void_probe_radius 1.2 _smtbx_masks_void_truncation_radius 1.2 _shelx_res_file ; TITL AG_HX_24R1_a.res in P-1 ag_hx_24r1_a.res created by SHELXL-2018/3 at 17:21:07 on 23-Mar-2021 REM Old TITL AG_HX_24R1 in P-1 REM SHELXT solution in P-1 REM R1 0.248, Rweak 0.041, Alpha 0.050, Orientation as input REM Formula found by SHELXT: C27 N2 O2 S2 CELL 0.71073 8.6676 10.309 15.1742 75.237 82.715 71.385 ZERR 2 0.0008 0.0008 0.0013 0.007 0.007 0.008 LATT 1 SFAC C H N O S UNIT 56 46 2 4 4 L.S. 24 PLAN 4 SIZE 0.36 0.22 0.16 TEMP 21.85 CONF MORE -1 BOND $H fmap 2 acta OMIT -3 53 REM REM REM WGHT 0.037500 FVAR 0.84243 C1 1 0.286200 1.640845 -0.093587 11.00000 0.05912 0.05983 = 0.11391 -0.01205 -0.00348 -0.01878 C2 1 0.286208 1.786469 -0.147446 11.00000 0.11905 0.05644 = 0.20119 0.01394 -0.02085 -0.04473 AFIX 137 H2A 2 0.266662 1.847897 -0.106478 11.00000 -1.50000 H2B 2 0.201953 1.822145 -0.190456 11.00000 -1.50000 H2C 2 0.390014 1.781619 -0.179524 11.00000 -1.50000 AFIX 0 C3 1 0.266987 1.377405 -0.089835 11.00000 0.07503 0.04519 = 0.04986 -0.00004 0.00160 -0.01228 C4 1 0.398427 1.284970 -0.041036 11.00000 0.05818 0.05630 = 0.07212 -0.00824 0.00550 -0.02050 AFIX 43 H4 2 0.496992 1.305226 -0.047713 11.00000 -1.20000 AFIX 0 C5 1 0.382906 1.162630 0.017574 11.00000 0.06008 0.05092 = 0.06890 -0.00148 -0.00787 -0.01093 AFIX 43 H5 2 0.470892 1.101914 0.051200 11.00000 -1.20000 AFIX 0 C6 1 0.237895 1.128799 0.027107 11.00000 0.06041 0.04250 = 0.05164 -0.00398 -0.00298 -0.01330 C7 1 0.109564 1.221921 -0.023448 11.00000 0.06274 0.05677 = 0.06518 0.00255 -0.00818 -0.01984 AFIX 43 H7 2 0.012019 1.200527 -0.018955 11.00000 -1.20000 AFIX 0 C8 1 0.122735 1.344583 -0.079825 11.00000 0.07098 0.05683 = 0.06382 0.00864 -0.01527 -0.00989 AFIX 43 H8 2 0.033447 1.406659 -0.111817 11.00000 -1.20000 AFIX 0 C9 1 0.219094 1.004364 0.090052 11.00000 0.05812 0.04797 = 0.06245 -0.00295 -0.00775 -0.01283 C10 1 0.196734 0.905093 0.144238 11.00000 0.05939 0.04721 = 0.06189 0.00020 -0.00982 -0.01600 C11 1 0.163708 0.789472 0.211152 11.00000 0.06014 0.04353 = 0.04816 -0.00018 -0.00813 -0.01483 C12 1 0.002540 0.795102 0.236955 11.00000 0.05444 0.04384 = 0.05698 -0.00171 -0.01422 -0.00788 AFIX 43 H12 2 -0.080461 0.872805 0.210152 11.00000 -1.20000 AFIX 0 C13 1 -0.037523 0.686695 0.302220 11.00000 0.04630 0.04714 = 0.05527 -0.00824 -0.00528 -0.00946 C14 1 0.091404 0.572818 0.342150 11.00000 0.06136 0.04374 = 0.05134 -0.00225 -0.00060 -0.01421 AFIX 43 H14 2 0.068505 0.499595 0.386495 11.00000 -1.20000 AFIX 0 C15 1 0.252527 0.567272 0.316771 11.00000 0.05566 0.04259 = 0.04818 -0.00767 -0.00628 -0.00793 C16 1 0.289628 0.675398 0.250855 11.00000 0.04891 0.05214 = 0.05570 -0.00248 -0.00596 -0.01580 AFIX 43 H16 2 0.397575 0.671421 0.233518 11.00000 -1.20000 AFIX 0 C17 1 -0.328976 0.812147 0.288065 11.00000 0.05523 0.07634 = 0.10113 -0.01976 -0.00370 -0.01116 AFIX 137 H17A 2 -0.308953 0.895807 0.294043 11.00000 -1.50000 H17B 2 -0.429570 0.804989 0.320497 11.00000 -1.50000 H17C 2 -0.336077 0.816344 0.224724 11.00000 -1.50000 AFIX 0 C18 1 -0.238041 0.575077 0.389179 11.00000 0.06493 0.08894 = 0.08257 0.00123 0.00893 -0.02850 AFIX 137 H18A 2 -0.182930 0.489389 0.369852 11.00000 -1.50000 H18B 2 -0.353680 0.591159 0.391302 11.00000 -1.50000 H18C 2 -0.205001 0.567708 0.448747 11.00000 -1.50000 AFIX 0 C19 1 0.381304 0.448143 0.360538 11.00000 0.05130 0.05018 = 0.05447 -0.00537 0.00206 -0.01708 C20 1 0.485001 0.349472 0.398457 11.00000 0.05293 0.05064 = 0.05194 -0.00159 -0.00058 -0.01158 C21 1 0.602193 0.228641 0.449351 11.00000 0.04491 0.05156 = 0.04965 -0.00184 -0.00491 -0.01054 C22 1 0.681090 0.242156 0.518609 11.00000 0.06334 0.04618 = 0.06404 -0.00765 -0.00585 -0.00971 AFIX 43 H22 2 0.666138 0.330792 0.528615 11.00000 -1.20000 AFIX 0 C23 1 0.782002 0.124967 0.573084 11.00000 0.06346 0.06963 = 0.06025 -0.01259 -0.01557 -0.01140 AFIX 43 H23 2 0.835232 0.135220 0.619220 11.00000 -1.20000 AFIX 0 C24 1 0.804205 -0.006969 0.559441 11.00000 0.04467 0.05496 = 0.06335 0.00073 -0.00979 -0.00090 C25 1 0.730940 -0.019499 0.488431 11.00000 0.07657 0.04792 = 0.09301 -0.01203 -0.02943 -0.00013 AFIX 43 H25 2 0.749138 -0.107791 0.477035 11.00000 -1.20000 AFIX 0 C26 1 0.630559 0.097258 0.433680 11.00000 0.07052 0.05653 = 0.08059 -0.01349 -0.03013 -0.00553 AFIX 43 H26 2 0.581674 0.087011 0.385776 11.00000 -1.20000 AFIX 0 C27 1 0.766054 -0.185919 0.722392 11.00000 0.07049 0.05961 = 0.06213 -0.01280 -0.01952 -0.00562 C28 1 0.826503 -0.317117 0.794637 11.00000 0.10213 0.05959 = 0.06332 -0.00324 -0.01938 0.00655 AFIX 137 H28A 2 0.869362 -0.295486 0.842601 11.00000 -1.50000 H28B 2 0.910790 -0.385010 0.768559 11.00000 -1.50000 H28C 2 0.738104 -0.354946 0.819058 11.00000 -1.50000 AFIX 0 N1 3 -0.196822 0.690504 0.325648 11.00000 0.04878 0.06105 = 0.09550 0.01035 -0.00313 -0.00979 O1 4 0.283297 1.603348 -0.012219 11.00000 0.11693 0.08222 = 0.11261 -0.02425 -0.00991 -0.03183 O2 4 0.630497 -0.107145 0.721835 11.00000 0.06194 0.08118 = 0.07906 -0.00273 -0.01014 0.00061 S1 5 0.285199 1.531895 -0.167201 11.00000 0.11122 0.06279 = 0.07466 0.01033 0.01015 -0.02627 S2 5 0.918885 -0.159053 0.634835 11.00000 0.05788 0.07276 = 0.08291 0.00646 -0.01064 0.00845 HKLF 4 REM AG_HX_24R1_a.res in P-1 REM wR2 = 0.1383, GooF = S = 0.981, Restrained GooF = 0.981 for all data REM R1 = 0.0584 for 2156 Fo > 4sig(Fo) and 0.1609 for all 5061 data REM 302 parameters refined using 0 restraints END WGHT 0.0375 0.0000 REM Highest difference peak 0.176, deepest hole -0.222, 1-sigma level 0.040 Q1 1 0.2737 1.5198 -0.1816 11.00000 0.05 0.18 Q2 1 0.9618 -0.3237 0.7935 11.00000 0.05 0.17 Q3 1 0.7827 -0.4188 0.7719 11.00000 0.05 0.17 Q4 1 0.4825 1.5690 -0.1424 11.00000 0.05 0.16 ; _shelx_res_checksum 15895 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2862(4) 1.6408(4) -0.0936(3) 0.0789(13) Uani 1 1 d . . . . . C2 C 0.2862(5) 1.7865(4) -0.1474(3) 0.1281(19) Uani 1 1 d . . . . . H2A H 0.266662 1.847897 -0.106478 0.192 Uiso 1 1 calc R U . . . H2B H 0.201953 1.822145 -0.190456 0.192 Uiso 1 1 calc R U . . . H2C H 0.390014 1.781619 -0.179524 0.192 Uiso 1 1 calc R U . . . C3 C 0.2670(5) 1.3774(3) -0.0898(2) 0.0606(10) Uani 1 1 d . . . . . C4 C 0.3984(4) 1.2850(3) -0.0410(2) 0.0634(10) Uani 1 1 d . . . . . H4 H 0.496992 1.305226 -0.047713 0.076 Uiso 1 1 calc R U . . . C5 C 0.3829(4) 1.1626(3) 0.0176(2) 0.0632(10) Uani 1 1 d . . . . . H5 H 0.470892 1.101914 0.051200 0.076 Uiso 1 1 calc R U . . . C6 C 0.2379(4) 1.1288(3) 0.0271(2) 0.0533(9) Uani 1 1 d . . . . . C7 C 0.1096(4) 1.2219(3) -0.0234(2) 0.0638(10) Uani 1 1 d . . . . . H7 H 0.012019 1.200527 -0.018955 0.077 Uiso 1 1 calc R U . . . C8 C 0.1227(5) 1.3446(4) -0.0798(2) 0.0693(11) Uani 1 1 d . . . . . H8 H 0.033447 1.406659 -0.111817 0.083 Uiso 1 1 calc R U . . . C9 C 0.2191(4) 1.0044(3) 0.0901(2) 0.0583(9) Uani 1 1 d . . . . . C10 C 0.1967(4) 0.9051(3) 0.1442(2) 0.0579(9) Uani 1 1 d . . . . . C11 C 0.1637(4) 0.7895(3) 0.2112(2) 0.0522(9) Uani 1 1 d . . . . . C12 C 0.0025(4) 0.7951(3) 0.2370(2) 0.0542(9) Uani 1 1 d . . . . . H12 H -0.080461 0.872805 0.210152 0.065 Uiso 1 1 calc R U . . . C13 C -0.0375(4) 0.6867(3) 0.3022(2) 0.0511(8) Uani 1 1 d . . . . . C14 C 0.0914(4) 0.5728(3) 0.3422(2) 0.0544(9) Uani 1 1 d . . . . . H14 H 0.068505 0.499595 0.386495 0.065 Uiso 1 1 calc R U . . . C15 C 0.2525(4) 0.5673(3) 0.3168(2) 0.0506(8) Uani 1 1 d . . . . . C16 C 0.2896(4) 0.6754(3) 0.2509(2) 0.0536(9) Uani 1 1 d . . . . . H16 H 0.397575 0.671421 0.233518 0.064 Uiso 1 1 calc R U . . . C17 C -0.3290(4) 0.8121(4) 0.2881(2) 0.0797(12) Uani 1 1 d . . . . . H17A H -0.308953 0.895807 0.294043 0.120 Uiso 1 1 calc R U . . . H17B H -0.429570 0.804989 0.320497 0.120 Uiso 1 1 calc R U . . . H17C H -0.336077 0.816344 0.224724 0.120 Uiso 1 1 calc R U . . . C18 C -0.2380(4) 0.5751(4) 0.3892(2) 0.0826(12) Uani 1 1 d . . . . . H18A H -0.182930 0.489389 0.369852 0.124 Uiso 1 1 calc R U . . . H18B H -0.353680 0.591159 0.391302 0.124 Uiso 1 1 calc R U . . . H18C H -0.205001 0.567708 0.448747 0.124 Uiso 1 1 calc R U . . . C19 C 0.3813(4) 0.4481(3) 0.3605(2) 0.0532(9) Uani 1 1 d . . . . . C20 C 0.4850(4) 0.3495(3) 0.3985(2) 0.0549(9) Uani 1 1 d . . . . . C21 C 0.6022(4) 0.2286(4) 0.4494(2) 0.0513(8) Uani 1 1 d . . . . . C22 C 0.6811(4) 0.2422(3) 0.5186(2) 0.0602(9) Uani 1 1 d . . . . . H22 H 0.666138 0.330792 0.528615 0.072 Uiso 1 1 calc R U . . . C23 C 0.7820(4) 0.1250(4) 0.5731(2) 0.0658(10) Uani 1 1 d . . . . . H23 H 0.835232 0.135220 0.619220 0.079 Uiso 1 1 calc R U . . . C24 C 0.8042(4) -0.0070(4) 0.5594(2) 0.0598(10) Uani 1 1 d . . . . . C25 C 0.7309(4) -0.0195(4) 0.4884(3) 0.0754(11) Uani 1 1 d . . . . . H25 H 0.749138 -0.107791 0.477035 0.091 Uiso 1 1 calc R U . . . C26 C 0.6306(4) 0.0973(4) 0.4337(2) 0.0705(10) Uani 1 1 d . . . . . H26 H 0.581674 0.087011 0.385776 0.085 Uiso 1 1 calc R U . . . C27 C 0.7661(5) -0.1859(4) 0.7224(2) 0.0662(10) Uani 1 1 d . . . . . C28 C 0.8265(4) -0.3171(3) 0.7946(2) 0.0831(12) Uani 1 1 d . . . . . H28A H 0.869362 -0.295486 0.842601 0.125 Uiso 1 1 calc R U . . . H28B H 0.910790 -0.385010 0.768559 0.125 Uiso 1 1 calc R U . . . H28C H 0.738104 -0.354946 0.819058 0.125 Uiso 1 1 calc R U . . . N1 N -0.1968(3) 0.6905(3) 0.3256(2) 0.0755(9) Uani 1 1 d . . . . . O1 O 0.2833(4) 1.6033(3) -0.0122(2) 0.1026(10) Uani 1 1 d . . . . . O2 O 0.6305(3) -0.1071(3) 0.72184(16) 0.0818(8) Uani 1 1 d . . . . . S1 S 0.28520(13) 1.53190(10) -0.16720(7) 0.0891(4) Uani 1 1 d . . . . . S2 S 0.91888(11) -0.15905(10) 0.63483(7) 0.0820(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 0.059(3) 0.060(3) 0.114(4) -0.012(3) -0.003(3) -0.019(2) C2 0.119(4) 0.056(3) 0.201(5) 0.014(3) -0.021(3) -0.045(3) C3 0.075(3) 0.045(2) 0.050(2) 0.0000(17) 0.0016(19) -0.0123(19) C4 0.058(2) 0.056(2) 0.072(2) -0.008(2) 0.005(2) -0.0205(19) C5 0.060(2) 0.051(2) 0.069(2) -0.0015(18) -0.0079(18) -0.0109(18) C6 0.060(2) 0.043(2) 0.052(2) -0.0040(16) -0.0030(18) -0.0133(18) C7 0.063(2) 0.057(2) 0.065(2) 0.0025(19) -0.0082(19) -0.0198(19) C8 0.071(3) 0.057(2) 0.064(2) 0.0086(19) -0.015(2) -0.010(2) C9 0.058(2) 0.048(2) 0.062(2) -0.0030(18) -0.0078(18) -0.0128(18) C10 0.059(2) 0.047(2) 0.062(2) 0.0002(18) -0.0098(18) -0.0160(18) C11 0.060(2) 0.044(2) 0.0482(19) -0.0002(16) -0.0081(17) -0.0148(18) C12 0.054(2) 0.044(2) 0.057(2) -0.0017(17) -0.0142(18) -0.0079(17) C13 0.046(2) 0.047(2) 0.055(2) -0.0082(17) -0.0053(17) -0.0095(17) C14 0.061(2) 0.044(2) 0.051(2) -0.0023(16) -0.0006(18) -0.0142(18) C15 0.056(2) 0.043(2) 0.048(2) -0.0077(16) -0.0063(17) -0.0079(17) C16 0.049(2) 0.052(2) 0.056(2) -0.0025(17) -0.0060(17) -0.0158(18) C17 0.055(2) 0.076(3) 0.101(3) -0.020(2) -0.004(2) -0.011(2) C18 0.065(3) 0.089(3) 0.083(3) 0.001(2) 0.009(2) -0.028(2) C19 0.051(2) 0.050(2) 0.054(2) -0.0054(18) 0.0021(17) -0.0171(18) C20 0.053(2) 0.051(2) 0.052(2) -0.0016(18) -0.0006(17) -0.0116(18) C21 0.045(2) 0.052(2) 0.050(2) -0.0018(18) -0.0049(17) -0.0105(17) C22 0.063(2) 0.046(2) 0.064(2) -0.0076(18) -0.0058(19) -0.0097(18) C23 0.063(2) 0.070(3) 0.060(2) -0.013(2) -0.0156(18) -0.011(2) C24 0.045(2) 0.055(2) 0.063(2) 0.0007(19) -0.0098(18) -0.0009(17) C25 0.077(3) 0.048(2) 0.093(3) -0.012(2) -0.029(2) 0.000(2) C26 0.071(3) 0.057(2) 0.081(3) -0.013(2) -0.030(2) -0.006(2) C27 0.070(3) 0.060(2) 0.062(2) -0.013(2) -0.020(2) -0.006(2) C28 0.102(3) 0.060(2) 0.063(2) -0.003(2) -0.019(2) 0.007(2) N1 0.0488(19) 0.061(2) 0.096(2) 0.0104(17) -0.0031(17) -0.0098(16) O1 0.117(3) 0.082(2) 0.113(2) -0.024(2) -0.010(2) -0.0318(17) O2 0.0619(17) 0.0812(18) 0.0791(18) -0.0027(14) -0.0101(14) 0.0006(14) S1 0.1112(9) 0.0628(7) 0.0747(7) 0.0103(6) 0.0101(6) -0.0263(6) S2 0.0579(6) 0.0728(7) 0.0829(7) 0.0065(6) -0.0106(5) 0.0085(5) 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 C2 C1 S1 111.1(3) . . ? O1 C1 C2 125.3(4) . . ? O1 C1 S1 123.6(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 S1 120.7(3) . . ? C8 C3 C4 119.2(3) . . ? C8 C3 S1 120.1(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4 120.1 . . ? C4 C5 H5 119.5 . . ? C4 C5 C6 121.0(3) . . ? C6 C5 H5 119.5 . . ? C5 C6 C9 121.3(3) . . ? C7 C6 C5 117.9(3) . . ? C7 C6 C9 120.8(3) . . ? C6 C7 H7 119.3 . . ? C8 C7 C6 121.4(3) . . ? C8 C7 H7 119.3 . . ? C3 C8 H8 119.7 . . ? C7 C8 C3 120.6(3) . . ? C7 C8 H8 119.7 . . ? C10 C9 C6 176.7(4) . . ? C9 C10 C11 177.5(4) . . ? C12 C11 C10 118.7(3) . . ? C16 C11 C10 121.0(3) . . ? C16 C11 C12 120.4(3) . . ? C11 C12 H12 119.3 . . ? C11 C12 C13 121.4(3) . . ? C13 C12 H12 119.3 . . ? C12 C13 C14 117.4(3) . . ? N1 C13 C12 121.3(3) . . ? N1 C13 C14 121.3(3) . . ? C13 C14 H14 119.4 . . ? C15 C14 C13 121.3(3) . . ? C15 C14 H14 119.4 . . ? C14 C15 C19 119.2(3) . . ? C16 C15 C14 120.4(3) . . ? C16 C15 C19 120.4(3) . . ? C11 C16 C15 119.2(3) . . ? C11 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? C20 C19 C15 178.4(3) . . ? C19 C20 C21 176.1(3) . . ? C22 C21 C20 120.2(3) . . ? C26 C21 C20 120.9(3) . . ? C26 C21 C22 118.8(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.8 . . ? C22 C23 H23 119.8 . . ? C24 C23 C22 120.3(4) . . ? C24 C23 H23 119.8 . . ? C23 C24 S2 120.8(3) . . ? C25 C24 C23 119.0(3) . . ? C25 C24 S2 120.2(3) . . ? C24 C25 H25 119.6 . . ? C24 C25 C26 120.8(4) . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 120.5(4) . . ? C21 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C28 C27 S2 112.7(3) . . ? O2 C27 C28 124.5(3) . . ? O2 C27 S2 122.8(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C13 N1 C17 120.8(3) . . ? C13 N1 C18 121.3(3) . . ? C18 N1 C17 117.9(3) . . ? C3 S1 C1 102.52(19) . . ? C24 S2 C27 100.49(16) . . ? 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 C2 1.515(5) . ? C1 O1 1.196(4) . ? C1 S1 1.777(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.384(4) . ? C3 C8 1.377(4) . ? C3 S1 1.761(3) . ? C4 H4 0.9300 . ? C4 C5 1.381(4) . ? C5 H5 0.9300 . ? C5 C6 1.389(4) . ? C6 C7 1.381(4) . ? C6 C9 1.433(4) . ? C7 H7 0.9300 . ? C7 C8 1.364(4) . ? C8 H8 0.9300 . ? C9 C10 1.191(4) . ? C10 C11 1.436(4) . ? C11 C12 1.389(4) . ? C11 C16 1.387(4) . ? C12 H12 0.9300 . ? C12 C13 1.395(4) . ? C13 C14 1.402(4) . ? C13 N1 1.372(4) . ? C14 H14 0.9300 . ? C14 C15 1.388(4) . ? C15 C16 1.388(4) . ? C15 C19 1.446(4) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 N1 1.447(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C18 N1 1.440(3) . ? C19 C20 1.193(4) . ? C20 C21 1.442(4) . ? C21 C22 1.382(4) . ? C21 C26 1.374(4) . ? C22 H22 0.9300 . ? C22 C23 1.381(4) . ? C23 H23 0.9300 . ? C23 C24 1.377(4) . ? C24 C25 1.370(5) . ? C24 S2 1.770(3) . ? C25 H25 0.9300 . ? C25 C26 1.379(4) . ? C26 H26 0.9300 . ? C27 C28 1.498(4) . ? C27 O2 1.196(3) . ? C27 S2 1.788(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 C2 C1 S1 C3 -175.0(3) . . . . ? C3 C4 C5 C6 1.4(5) . . . . ? C4 C3 C8 C7 -0.8(5) . . . . ? C4 C3 S1 C1 -74.6(3) . . . . ? C4 C5 C6 C7 -0.4(5) . . . . ? C4 C5 C6 C9 -177.9(3) . . . . ? C5 C6 C7 C8 -1.2(5) . . . . ? C6 C7 C8 C3 1.8(5) . . . . ? C8 C3 C4 C5 -0.8(5) . . . . ? C8 C3 S1 C1 107.9(3) . . . . ? C9 C6 C7 C8 176.3(3) . . . . ? C10 C11 C12 C13 -179.4(3) . . . . ? C10 C11 C16 C15 178.5(3) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C11 C12 C13 N1 -178.0(3) . . . . ? C12 C11 C16 C15 -0.2(5) . . . . ? C12 C13 C14 C15 -0.9(5) . . . . ? C12 C13 N1 C17 -4.5(5) . . . . ? C12 C13 N1 C18 176.5(3) . . . . ? C13 C14 C15 C16 0.1(5) . . . . ? C13 C14 C15 C19 179.5(3) . . . . ? C14 C13 N1 C17 176.3(3) . . . . ? C14 C13 N1 C18 -2.7(5) . . . . ? C14 C15 C16 C11 0.4(5) . . . . ? C16 C11 C12 C13 -0.7(5) . . . . ? C19 C15 C16 C11 -178.9(3) . . . . ? C20 C21 C22 C23 174.0(3) . . . . ? C20 C21 C26 C25 -173.8(3) . . . . ? C21 C22 C23 C24 -0.5(5) . . . . ? C22 C21 C26 C25 2.5(5) . . . . ? C22 C23 C24 C25 3.1(5) . . . . ? C22 C23 C24 S2 -174.5(2) . . . . ? C23 C24 C25 C26 -2.8(5) . . . . ? C23 C24 S2 C27 84.4(3) . . . . ? C24 C25 C26 C21 0.0(5) . . . . ? C25 C24 S2 C27 -93.1(3) . . . . ? C26 C21 C22 C23 -2.3(5) . . . . ? C28 C27 S2 C24 176.0(3) . . . . ? N1 C13 C14 C15 178.3(3) . . . . ? O1 C1 S1 C3 3.4(4) . . . . ? O2 C27 S2 C24 -3.5(4) . . . . ? S1 C3 C4 C5 -178.4(3) . . . . ? S1 C3 C8 C7 176.8(3) . . . . ? S2 C24 C25 C26 174.7(3) . . . . ?