#------------------------------------------------------------------------------ #$Date: 2023-11-11 01:57:02 +0200 (Sat, 11 Nov 2023) $ #$Revision: 287527 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247700.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_7247700 loop_ _publ_author_name 'Ahmed, Muhammad Naeem' 'Akhtar, Maheen' 'Andleeb, Hina' 'Bashir, Muhammad Adnan' 'Ibrahim, Mahmoud A. A.' 'Sidhom, Peter' 'Arshad, Ifzan' 'Tahir, Muhammad Nawaz' 'Gil, Diego Mauricio' 'Gomila, Rosa Maria' 'Frontera, Antonio' _publ_section_title ; Crystal engineering with 1,3,4-oxadiazoles derivatives: On the importance of CH···N and CH···\p interactions ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00944K _journal_year 2023 _chemical_formula_iupac 'C19 H20 N2 O S' _chemical_formula_moiety 'C19 H20 N2 O S' _chemical_formula_sum 'C19 H20 N2 O S' _chemical_formula_weight 324.43 _chemical_name_systematic ; 2-[(4-Tertbutylphenylmethyl)sulfanyl]-5-(phenyl)-1,3,4-oxadiazole ; _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-10-06 deposited with the CCDC. 2023-10-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.9410(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.50070(10) _cell_length_b 19.5547(2) _cell_length_c 8.63490(10) _cell_measurement_reflns_used 3204 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 76.398 _cell_measurement_theta_min 4.522 _cell_volume 1756.07(3) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 7.93 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RINC): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_unetI/netI 0.0134 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 21438 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.398 _diffrn_reflns_theta_min 4.522 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.672 _exptl_absorpt_correction_T_max 0.615 _exptl_absorpt_correction_T_min 0.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022) Empirical absorption correctionusing spherical harmonics, implimented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.185 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef 0.0062(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 3589 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0717P)^2^+0.1517P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1194 _refine_ls_wR_factor_ref 0.1225 _reflns_number_gt 3204 _reflns_number_total 3589 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d3ce00944k2.cif _cod_data_source_block 1_AUTO _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247700 _shelx_shelxl_version_number 2019/2 _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_min 0.584 _shelx_estimated_absorpt_t_max 0.710 _shelx_res_file ; TITL 1_auto_a.res in P2(1)/c light yellow rod shelx.res created by SHELXL-2019/2 at 14:15:32 on 05-Oct-2023 CELL 1.54184 10.5007 19.5547 8.6349 90.000 97.941 90.000 ZERR 4.00 0.0001 0.0002 0.0001 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 76 80 8 4 4 ACTA L.S. 40 MERG 2 MORE -1 FMAP 2 PLAN 10 BOND $H HTAB CONF LIST 4 TEMP 23.00 SIZE 0.36 0.24 0.22 DFIX 1.51 0.01 C10 C11A C10 C12A C10 C13A DANG 2.50 0.02 C11A C12A C12A C13A C13A C11A DFIX 1.51 0.01 C10 C11B C10 C12B C10 C13B DANG 2.50 0.02 C11B C12B C12B C13B C13B C11B EADP C11A C11B EADP C12A C12B EADP C13A C13B MPLA 6 C14 C15 C16 C17 C18 C19 MPLA 6 C1 C2 N1 N2 O1 S1 MPLA 7 C3 C4 C5 C6 C7 C8 C9 MPLA 6 C14 C15 C16 C17 C18 C19 WGHT 0.071700 0.151700 EXTI 0.006165 FVAR 0.78786 0.86914 S1 5 0.376259 0.085938 0.902868 11.00000 0.10253 0.05667 = 0.05655 -0.00616 -0.01017 0.00235 O1 4 0.503908 0.083085 1.191499 11.00000 0.07622 0.04930 = 0.05485 0.00007 -0.00430 0.00280 N1 3 0.462162 0.187771 1.105694 11.00000 0.09413 0.05361 = 0.05764 0.00055 -0.01156 0.00377 N2 3 0.526669 0.191163 1.259874 11.00000 0.08954 0.05266 = 0.05830 -0.00118 -0.01089 0.00344 C1 1 0.451081 0.124101 1.072523 11.00000 0.06804 0.05351 = 0.05001 0.00097 0.00105 0.00311 C2 1 0.548527 0.129631 1.305114 11.00000 0.05529 0.05206 = 0.05252 -0.00259 0.00341 0.00131 C3 1 0.318720 0.164587 0.804798 11.00000 0.09702 0.05891 = 0.05551 0.00045 -0.01130 -0.00386 AFIX 23 H3A 2 0.270313 0.190481 0.872702 11.00000 -1.20000 H3B 2 0.391843 0.192078 0.785663 11.00000 -1.20000 AFIX 0 C4 1 0.234807 0.151253 0.652015 11.00000 0.07634 0.05694 = 0.05079 -0.00026 -0.00225 -0.00427 C5 1 0.273650 0.171914 0.513475 11.00000 0.06098 0.06020 = 0.05918 0.00100 0.00240 -0.00717 AFIX 43 H5 2 0.355624 0.189978 0.513883 11.00000 -1.20000 AFIX 0 C6 1 0.192231 0.166152 0.373435 11.00000 0.06245 0.06402 = 0.04874 0.00378 0.00793 -0.00607 AFIX 43 H6 2 0.220898 0.180673 0.281678 11.00000 -1.20000 AFIX 0 C7 1 0.069564 0.139435 0.366114 11.00000 0.05900 0.06696 = 0.04966 -0.00145 0.00555 -0.00266 C8 1 0.032902 0.117582 0.506580 11.00000 0.06906 0.11470 = 0.05698 0.00316 0.00903 -0.02715 AFIX 43 H8 2 -0.048367 0.098653 0.506399 11.00000 -1.20000 AFIX 0 C9 1 0.113276 0.123139 0.645693 11.00000 0.09034 0.10716 = 0.04948 0.00574 0.01109 -0.02550 AFIX 43 H9 2 0.085507 0.107729 0.737274 11.00000 -1.20000 AFIX 0 C10 1 -0.023151 0.135313 0.214088 11.00000 0.06400 0.09696 = 0.05653 0.00042 -0.00079 -0.00915 PART 1 C11A 1 0.040688 0.148669 0.071569 21.00000 0.08914 0.20397 = 0.04516 0.00617 -0.00047 -0.02266 AFIX 33 H11A 2 -0.021908 0.145429 -0.020326 21.00000 -1.50000 H11B 2 0.077561 0.193675 0.078060 21.00000 -1.50000 H11C 2 0.107180 0.115432 0.065963 21.00000 -1.50000 AFIX 0 C12A 1 -0.090255 0.065717 0.203357 21.00000 0.15455 0.15267 = 0.07840 -0.00986 -0.01920 -0.07672 AFIX 33 H12A 2 -0.130208 0.058373 0.295479 21.00000 -1.50000 H12B 2 -0.154538 0.064737 0.112802 21.00000 -1.50000 H12C 2 -0.028140 0.030357 0.195055 21.00000 -1.50000 AFIX 0 C13A 1 -0.127562 0.190129 0.221917 21.00000 0.08719 0.18775 = 0.09644 0.00715 -0.01294 0.03735 AFIX 33 H13A 2 -0.169364 0.182338 0.312435 21.00000 -1.50000 H13B 2 -0.088600 0.234635 0.228677 21.00000 -1.50000 H13C 2 -0.189749 0.187554 0.129515 21.00000 -1.50000 AFIX 0 PART 2 C11B 1 0.031987 0.080046 0.111546 -21.00000 0.08914 0.20397 = 0.04516 0.00617 -0.00047 -0.02266 AFIX 33 H11D 2 0.120597 0.089967 0.104852 -21.00000 -1.50000 H11E 2 0.025431 0.035819 0.158050 -21.00000 -1.50000 H11F 2 -0.016102 0.080310 0.008571 -21.00000 -1.50000 AFIX 0 C12B 1 -0.160759 0.118238 0.221809 -21.00000 0.15455 0.15267 = 0.07840 -0.00986 -0.01920 -0.07672 AFIX 33 H12D 2 -0.207350 0.117453 0.118022 -21.00000 -1.50000 H12E 2 -0.166035 0.074152 0.269424 -21.00000 -1.50000 H12F 2 -0.197344 0.152133 0.282943 -21.00000 -1.50000 AFIX 0 C13B 1 -0.021163 0.203574 0.124128 -21.00000 0.08719 0.18775 = 0.09644 0.00715 -0.01294 0.03735 AFIX 33 H13D 2 0.066188 0.216163 0.116916 -21.00000 -1.50000 H13E 2 -0.067472 0.198295 0.020919 -21.00000 -1.50000 H13F 2 -0.060972 0.238653 0.178685 -21.00000 -1.50000 PART 0 AFIX 0 C14 1 0.611393 0.105579 1.456000 11.00000 0.05206 0.05862 = 0.05481 0.00157 0.00131 0.00036 C15 1 0.637718 0.152195 1.577327 11.00000 0.07718 0.06438 = 0.06550 -0.00474 -0.00574 0.00226 AFIX 43 H15 2 0.615800 0.197984 1.561386 11.00000 -1.20000 AFIX 0 C16 1 0.696125 0.130572 1.720764 11.00000 0.09899 0.09147 = 0.06384 -0.00911 -0.01706 -0.00483 AFIX 43 H16 2 0.713410 0.161642 1.802509 11.00000 -1.20000 AFIX 0 C17 1 0.729353 0.062481 1.743857 11.00000 0.09816 0.10090 = 0.06854 0.01790 -0.02047 0.00014 AFIX 43 H17 2 0.769078 0.047978 1.841261 11.00000 -1.20000 AFIX 0 C18 1 0.704291 0.016537 1.624929 11.00000 0.09127 0.07087 = 0.08296 0.01743 -0.01266 0.00642 AFIX 43 H18 2 0.727490 -0.029059 1.641357 11.00000 -1.20000 AFIX 0 C19 1 0.644631 0.037383 1.480214 11.00000 0.07272 0.05912 = 0.06497 0.00223 -0.00297 0.00310 AFIX 43 H19 2 0.626815 0.005899 1.399403 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_auto_a.res in P2(1)/c light yellow rod REM wR2 = 0.1225, GooF = S = 1.090, Restrained GooF = 1.099 for all data REM R1 = 0.0405 for 3204 Fo > 4sig(Fo) and 0.0435 for all 3589 data REM 219 parameters refined using 12 restraints END WGHT 0.0716 0.1515 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.185, deepest hole -0.201, 1-sigma level 0.047 Q1 1 -0.0656 0.2160 0.1753 11.00000 0.05 0.19 Q2 1 -0.0076 0.0545 0.1465 11.00000 0.05 0.18 Q3 1 0.0665 0.0843 0.0781 11.00000 0.05 0.17 Q4 1 0.5403 0.2239 1.2873 11.00000 0.05 0.15 Q5 1 0.6861 0.0386 1.6869 11.00000 0.05 0.15 Q6 1 0.6631 0.0274 1.5653 11.00000 0.05 0.15 Q7 1 0.3413 0.2033 0.8410 11.00000 0.05 0.15 Q8 1 0.4378 0.2141 1.0788 11.00000 0.05 0.13 Q9 1 0.6091 0.0691 1.4738 11.00000 0.05 0.13 Q10 1 0.5682 -0.0021 1.3877 11.00000 0.05 0.12 ; _shelx_res_checksum 63255 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 S1 S 0.37626(4) 0.08594(2) 0.90287(4) 0.07390(18) Uani 1 1 d . . . . . O1 O 0.50391(10) 0.08308(4) 1.19150(11) 0.0614(3) Uani 1 1 d . . . . . N1 N 0.46216(13) 0.18777(6) 1.10569(14) 0.0705(3) Uani 1 1 d . . . . . N2 N 0.52667(13) 0.19116(6) 1.25987(14) 0.0688(3) Uani 1 1 d . . . . . C1 C 0.45108(13) 0.12410(7) 1.07252(15) 0.0579(3) Uani 1 1 d . . . . . C2 C 0.54853(12) 0.12963(6) 1.30511(14) 0.0537(3) Uani 1 1 d . . . . . C3 C 0.31872(17) 0.16459(8) 0.80480(17) 0.0725(4) Uani 1 1 d . . . . . H3A H 0.270313 0.190481 0.872702 0.087 Uiso 1 1 calc R U . . . H3B H 0.391843 0.192078 0.785663 0.087 Uiso 1 1 calc R U . . . C4 C 0.23481(14) 0.15125(7) 0.65202(16) 0.0624(3) Uani 1 1 d . . . . . C5 C 0.27365(13) 0.17191(7) 0.51348(16) 0.0607(3) Uani 1 1 d . . . . . H5 H 0.355624 0.189978 0.513883 0.073 Uiso 1 1 calc R U . . . C6 C 0.19223(13) 0.16615(7) 0.37343(15) 0.0584(3) Uani 1 1 d . . . . . H6 H 0.220898 0.180673 0.281678 0.070 Uiso 1 1 calc R U . . . C7 C 0.06956(13) 0.13944(7) 0.36611(15) 0.0587(3) Uani 1 1 d . . . . . C8 C 0.03290(15) 0.11758(10) 0.50658(18) 0.0802(5) Uani 1 1 d . . . . . H8 H -0.048367 0.098653 0.506399 0.096 Uiso 1 1 calc R U . . . C9 C 0.11328(17) 0.12314(10) 0.64569(18) 0.0822(5) Uani 1 1 d . . . . . H9 H 0.085507 0.107729 0.737274 0.099 Uiso 1 1 calc R U . . . C10 C -0.02315(14) 0.13531(9) 0.21409(17) 0.0734(4) Uani 1 1 d D . . . . C11A C 0.0407(2) 0.14867(19) 0.0716(2) 0.1137(10) Uani 0.869(3) 1 d D . P A 1 H11A H -0.021908 0.145429 -0.020326 0.171 Uiso 0.869(3) 1 calc R U P A 1 H11B H 0.077561 0.193675 0.078060 0.171 Uiso 0.869(3) 1 calc R U P A 1 H11C H 0.107180 0.115432 0.065963 0.171 Uiso 0.869(3) 1 calc R U P A 1 C12A C -0.0903(3) 0.06572(17) 0.2034(3) 0.1319(13) Uani 0.869(3) 1 d D . P A 1 H12A H -0.130208 0.058373 0.295479 0.198 Uiso 0.869(3) 1 calc R U P A 1 H12B H -0.154538 0.064737 0.112802 0.198 Uiso 0.869(3) 1 calc R U P A 1 H12C H -0.028140 0.030357 0.195055 0.198 Uiso 0.869(3) 1 calc R U P A 1 C13A C -0.1276(2) 0.19013(18) 0.2219(3) 0.1262(11) Uani 0.869(3) 1 d D . P A 1 H13A H -0.169364 0.182338 0.312435 0.189 Uiso 0.869(3) 1 calc R U P A 1 H13B H -0.088600 0.234635 0.228677 0.189 Uiso 0.869(3) 1 calc R U P A 1 H13C H -0.189749 0.187554 0.129515 0.189 Uiso 0.869(3) 1 calc R U P A 1 C11B C 0.0320(14) 0.0800(7) 0.1115(15) 0.1137(10) Uani 0.131(3) 1 d D . P A 2 H11D H 0.120597 0.089967 0.104852 0.171 Uiso 0.131(3) 1 calc R U P A 2 H11E H 0.025431 0.035819 0.158050 0.171 Uiso 0.131(3) 1 calc R U P A 2 H11F H -0.016102 0.080310 0.008571 0.171 Uiso 0.131(3) 1 calc R U P A 2 C12B C -0.1608(10) 0.1182(11) 0.222(2) 0.1319(13) Uani 0.131(3) 1 d D . P A 2 H12D H -0.207350 0.117453 0.118022 0.198 Uiso 0.131(3) 1 calc R U P A 2 H12E H -0.166035 0.074152 0.269424 0.198 Uiso 0.131(3) 1 calc R U P A 2 H12F H -0.197344 0.152133 0.282943 0.198 Uiso 0.131(3) 1 calc R U P A 2 C13B C -0.0212(15) 0.2036(6) 0.124(2) 0.1262(11) Uani 0.131(3) 1 d D . P A 2 H13D H 0.066188 0.216163 0.116916 0.189 Uiso 0.131(3) 1 calc R U P A 2 H13E H -0.067472 0.198295 0.020919 0.189 Uiso 0.131(3) 1 calc R U P A 2 H13F H -0.060972 0.238653 0.178685 0.189 Uiso 0.131(3) 1 calc R U P A 2 C14 C 0.61139(12) 0.10558(7) 1.45600(15) 0.0557(3) Uani 1 1 d . . . . . C15 C 0.63772(15) 0.15220(8) 1.57733(18) 0.0705(4) Uani 1 1 d . . . . . H15 H 0.615800 0.197984 1.561386 0.085 Uiso 1 1 calc R U . . . C16 C 0.69612(19) 0.13057(10) 1.7208(2) 0.0874(5) Uani 1 1 d . . . . . H16 H 0.713410 0.161642 1.802509 0.105 Uiso 1 1 calc R U . . . C17 C 0.72935(19) 0.06248(11) 1.7439(2) 0.0922(5) Uani 1 1 d . . . . . H17 H 0.769078 0.047978 1.841261 0.111 Uiso 1 1 calc R U . . . C18 C 0.70429(17) 0.01654(9) 1.6249(2) 0.0840(5) Uani 1 1 d . . . . . H18 H 0.727490 -0.029059 1.641357 0.101 Uiso 1 1 calc R U . . . C19 C 0.64463(14) 0.03738(7) 1.48021(17) 0.0668(4) Uani 1 1 d . . . . . H19 H 0.626815 0.005899 1.399403 0.080 Uiso 1 1 calc R U . . . 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 S1 0.1025(3) 0.0567(2) 0.0565(2) -0.00616(13) -0.01017(19) 0.00235(16) O1 0.0762(6) 0.0493(5) 0.0548(5) 0.0001(3) -0.0043(4) 0.0028(4) N1 0.0941(8) 0.0536(6) 0.0576(6) 0.0006(5) -0.0116(6) 0.0038(6) N2 0.0895(8) 0.0527(6) 0.0583(6) -0.0012(5) -0.0109(6) 0.0034(5) C1 0.0680(7) 0.0535(7) 0.0500(6) 0.0010(5) 0.0010(5) 0.0031(5) C2 0.0553(6) 0.0521(6) 0.0525(6) -0.0026(5) 0.0034(5) 0.0013(5) C3 0.0970(11) 0.0589(8) 0.0555(8) 0.0005(6) -0.0113(7) -0.0039(7) C4 0.0763(8) 0.0569(7) 0.0508(7) -0.0003(5) -0.0023(6) -0.0043(6) C5 0.0610(7) 0.0602(7) 0.0592(7) 0.0010(6) 0.0024(6) -0.0072(6) C6 0.0625(7) 0.0640(8) 0.0487(6) 0.0038(5) 0.0079(5) -0.0061(6) C7 0.0590(7) 0.0670(8) 0.0497(7) -0.0014(5) 0.0056(5) -0.0027(6) C8 0.0691(9) 0.1147(13) 0.0570(8) 0.0032(8) 0.0090(7) -0.0272(9) C9 0.0903(11) 0.1072(13) 0.0495(7) 0.0057(8) 0.0111(7) -0.0255(9) C10 0.0640(8) 0.0970(12) 0.0565(8) 0.0004(7) -0.0008(6) -0.0092(7) C11A 0.0891(14) 0.204(3) 0.0452(9) 0.0062(13) -0.0005(9) -0.0227(17) C12A 0.155(3) 0.153(3) 0.0784(14) -0.0099(17) -0.0192(15) -0.077(2) C13A 0.0872(15) 0.188(3) 0.0964(17) 0.0072(18) -0.0129(12) 0.0374(18) C11B 0.0891(14) 0.204(3) 0.0452(9) 0.0062(13) -0.0005(9) -0.0227(17) C12B 0.155(3) 0.153(3) 0.0784(14) -0.0099(17) -0.0192(15) -0.077(2) C13B 0.0872(15) 0.188(3) 0.0964(17) 0.0072(18) -0.0129(12) 0.0374(18) C14 0.0521(6) 0.0586(7) 0.0548(7) 0.0016(5) 0.0013(5) 0.0004(5) C15 0.0772(9) 0.0644(8) 0.0655(8) -0.0047(6) -0.0057(7) 0.0023(6) C16 0.0990(12) 0.0915(12) 0.0638(9) -0.0091(8) -0.0171(8) -0.0048(9) C17 0.0982(12) 0.1009(13) 0.0685(10) 0.0179(9) -0.0205(9) 0.0001(10) C18 0.0913(11) 0.0709(9) 0.0830(10) 0.0174(8) -0.0127(8) 0.0064(8) C19 0.0727(8) 0.0591(8) 0.0650(8) 0.0022(6) -0.0030(6) 0.0031(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 C1 S1 C3 96.44(6) . . ? C1 O1 C2 102.25(10) . . ? C1 N1 N2 105.92(11) . . ? C2 N2 N1 106.70(11) . . ? N1 C1 O1 112.95(11) . . ? N1 C1 S1 128.69(10) . . ? O1 C1 S1 118.34(9) . . ? N2 C2 O1 112.17(11) . . ? N2 C2 C14 128.25(12) . . ? O1 C2 C14 119.58(11) . . ? C4 C3 S1 112.24(10) . . ? C4 C3 H3A 109.2 . . ? S1 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? S1 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C9 117.69(13) . . ? C5 C4 C3 120.21(13) . . ? C9 C4 C3 121.92(14) . . ? C4 C5 C6 120.88(12) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 121.93(12) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 C7 C8 116.41(12) . . ? C6 C7 C10 122.62(12) . . ? C8 C7 C10 120.95(12) . . ? C9 C8 C7 121.88(14) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C4 121.19(14) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? C12B C10 C7 118.7(7) . . ? C11A C10 C7 113.06(13) . . ? C11A C10 C12A 111.0(2) . . ? C7 C10 C12A 109.47(16) . . ? C11A C10 C13A 108.4(2) . . ? C7 C10 C13A 107.39(15) . . ? C12A C10 C13A 107.3(2) . . ? C12B C10 C13B 107.2(9) . . ? C7 C10 C13B 109.6(6) . . ? C12B C10 C11B 107.9(8) . . ? C7 C10 C11B 106.4(5) . . ? C13B C10 C11B 106.3(8) . . ? C10 C11A H11A 109.5 . . ? C10 C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10 C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C10 C12A H12A 109.5 . . ? C10 C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C10 C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C10 C13A H13A 109.5 . . ? C10 C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C10 C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C10 C11B H11D 109.5 . . ? C10 C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C10 C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C10 C12B H12D 109.5 . . ? C10 C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C10 C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C10 C13B H13D 109.5 . . ? C10 C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C10 C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C19 C14 C15 119.88(13) . . ? C19 C14 C2 121.29(12) . . ? C15 C14 C2 118.83(12) . . ? C16 C15 C14 119.82(15) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.96(16) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 120.48(15) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.27(16) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 119.60(14) . . ? C18 C19 H19 120.2 . . ? C14 C19 H19 120.2 . . ? 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 S1 C1 1.7327(13) . ? S1 C3 1.8183(15) . ? O1 C1 1.3598(15) . ? O1 C2 1.3724(15) . ? N1 C1 1.2793(17) . ? N1 N2 1.4094(17) . ? N2 C2 1.2761(16) . ? C2 C14 1.4549(17) . ? C3 C4 1.5046(18) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.3768(19) . ? C4 C9 1.384(2) . ? C5 C6 1.3857(18) . ? C5 H5 0.9300 . ? C6 C7 1.3833(19) . ? C6 H6 0.9300 . ? C7 C8 1.390(2) . ? C7 C10 1.5246(19) . ? C8 C9 1.374(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C12B 1.493(9) . ? C10 C11A 1.503(2) . ? C10 C12A 1.529(3) . ? C10 C13A 1.541(3) . ? C10 C13B 1.546(9) . ? C10 C11B 1.558(8) . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? C13A H13A 0.9600 . ? C13A H13B 0.9600 . ? C13A H13C 0.9600 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? C12B H12D 0.9600 . ? C12B H12E 0.9600 . ? C12B H12F 0.9600 . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 0.9600 . ? C14 C19 1.3870(19) . ? C14 C15 1.3874(19) . ? C15 C16 1.371(2) . ? C15 H15 0.9300 . ? C16 C17 1.384(3) . ? C16 H16 0.9300 . ? C17 C18 1.362(3) . ? C17 H17 0.9300 . ? C18 C19 1.380(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? 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 N1 N2 C2 0.07(17) . . . . ? N2 N1 C1 O1 -0.50(17) . . . . ? N2 N1 C1 S1 177.76(11) . . . . ? C2 O1 C1 N1 0.70(15) . . . . ? C2 O1 C1 S1 -177.76(9) . . . . ? C3 S1 C1 N1 -2.43(16) . . . . ? C3 S1 C1 O1 175.75(11) . . . . ? N1 N2 C2 O1 0.38(16) . . . . ? N1 N2 C2 C14 -179.24(12) . . . . ? C1 O1 C2 N2 -0.64(15) . . . . ? C1 O1 C2 C14 179.01(11) . . . . ? C1 S1 C3 C4 -174.65(12) . . . . ? S1 C3 C4 C5 -115.41(14) . . . . ? S1 C3 C4 C9 69.71(19) . . . . ? C9 C4 C5 C6 1.5(2) . . . . ? C3 C4 C5 C6 -173.56(13) . . . . ? C4 C5 C6 C7 -0.2(2) . . . . ? C5 C6 C7 C8 -1.0(2) . . . . ? C5 C6 C7 C10 177.52(14) . . . . ? C6 C7 C8 C9 1.0(3) . . . . ? C10 C7 C8 C9 -177.60(17) . . . . ? C7 C8 C9 C4 0.3(3) . . . . ? C5 C4 C9 C8 -1.6(3) . . . . ? C3 C4 C9 C8 173.42(17) . . . . ? C6 C7 C10 C12B -168.5(10) . . . . ? C8 C7 C10 C12B 9.9(10) . . . . ? C6 C7 C10 C11A 12.3(3) . . . . ? C8 C7 C10 C11A -169.2(2) . . . . ? C6 C7 C10 C12A 136.7(2) . . . . ? C8 C7 C10 C12A -44.9(3) . . . . ? C6 C7 C10 C13A -107.2(2) . . . . ? C8 C7 C10 C13A 71.3(2) . . . . ? C6 C7 C10 C13B -45.0(7) . . . . ? C8 C7 C10 C13B 133.5(7) . . . . ? C6 C7 C10 C11B 69.6(7) . . . . ? C8 C7 C10 C11B -111.9(7) . . . . ? N2 C2 C14 C19 -170.61(15) . . . . ? O1 C2 C14 C19 9.80(19) . . . . ? N2 C2 C14 C15 9.6(2) . . . . ? O1 C2 C14 C15 -169.97(12) . . . . ? C19 C14 C15 C16 -0.2(2) . . . . ? C2 C14 C15 C16 179.57(15) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? C17 C18 C19 C14 0.6(3) . . . . ? C15 C14 C19 C18 -0.3(2) . . . . ? C2 C14 C19 C18 179.92(14) . . . . ?