#------------------------------------------------------------------------------ #$Date: 2021-11-02 03:50:02 +0200 (Tue, 02 Nov 2021) $ #$Revision: 270194 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158383.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_7158383 loop_ _publ_author_name 'Fuller, Rebecca Olivia' 'Taylor, Madeleine' 'Duggin, Margot' 'Bissember, Alex C.' 'Canty, Allan J.' 'Judd, Martyna' 'Cox, Nick' 'Moggach, Stephen A.' 'Turner, Gemma' _publ_section_title ; Enhanced Synthesis of oxo-Verdazyl Radicals Bearing Sterically-and Electronically-Diverse C3-Substitents ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01946E _journal_year 2021 _chemical_formula_moiety 'C25 H22 N4 O S2' _chemical_formula_sum 'C25 H22 N4 O S2' _chemical_formula_weight 458.58 _chemical_name_common 1,5-bis(thiophenyl)-2,4-bis(methylbenzyl)-carbohydrazide _chemical_name_systematic 1,5-bis(thiophenyl)-2,4-bis(methylbenzyl)-carbohydrazide _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-09-03 _audit_creation_method ; Olex2 1.5 (compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394) ; _audit_update_record ; 2021-09-30 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.812(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.9089(3) _cell_length_b 11.6130(2) _cell_length_c 10.5619(2) _cell_measurement_reflns_used 7219 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 74.9210 _cell_measurement_theta_min 4.4390 _cell_volume 2319.04(7) _computing_cell_refinement 'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.958 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 23.00 114.00 0.50 0.05 -- 45.57 77.00 90.00 182 2 \w 23.00 118.00 0.50 0.05 -- 45.57 77.00 -30.00 190 3 \w 34.00 119.00 0.50 0.05 -- 45.57 38.00 -90.00 170 4 \w 31.00 118.00 0.50 0.05 -- 45.57 55.00-153.00 174 5 \w 30.00 71.00 0.50 0.16 -- 102.29 -61.00 -60.00 82 6 \w 30.00 71.00 0.50 0.16 -- 102.29 -61.00-120.00 82 7 \w 30.00 71.00 0.50 0.16 -- 102.29 -61.00-150.00 82 8 \w 30.00 71.00 0.50 0.16 -- 102.29 -61.00 -30.00 82 9 \w 30.00 63.00 0.50 0.16 -- 102.29 -55.00 63.00 66 10 \w 30.00 71.00 0.50 0.16 -- 102.29 -61.00 90.00 82 11 \w 79.00 174.00 0.50 0.16 -- 102.29 78.00 60.00 190 12 \w 86.00 174.00 0.50 0.16 -- 102.29 61.00 0.00 176 13 \w 88.00 174.00 0.50 0.16 -- 102.29 55.00-153.00 172 14 \w -26.00 30.00 0.50 0.05 -- -45.57 19.00 -30.00 112 15 \w -71.00 -30.00 0.50 0.16 -- -102.29 61.00 60.00 82 16 \w -71.00 -30.00 0.50 0.16 -- -102.29 61.00 0.00 82 17 \w -26.00 30.00 0.50 0.05 -- -45.57 19.00 60.00 112 18 \w -71.00 -30.00 0.50 0.16 -- -102.29 61.00 -30.00 82 19 \w -71.00 -30.00 0.50 0.16 -- -102.29 61.00-120.00 82 20 \w -63.00 -30.00 0.50 0.16 -- -102.29 55.00-153.00 66 21 \w -174.00 -83.00 0.50 0.16 -- -102.29 -93.00-162.00 182 22 \w -174.00 -90.00 0.50 0.16 -- -102.29 -45.00 0.00 168 23 \w -176.00 -89.00 0.50 0.16 -- -102.29 -15.00 120.00 174 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0687489000 _diffrn_orient_matrix_UB_12 -0.0614416000 _diffrn_orient_matrix_UB_13 -0.0414248000 _diffrn_orient_matrix_UB_21 0.0023469000 _diffrn_orient_matrix_UB_22 0.0621000000 _diffrn_orient_matrix_UB_23 -0.1286845000 _diffrn_orient_matrix_UB_31 0.0437225000 _diffrn_orient_matrix_UB_32 -0.0998798000 _diffrn_orient_matrix_UB_33 -0.0545843000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_unetI/netI 0.0217 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.958 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10618 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.958 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.449 _diffrn_reflns_theta_min 4.468 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.276 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.313 _exptl_crystal_description block _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.345 _exptl_crystal_size_mid 0.242 _exptl_crystal_size_min 0.181 _refine_diff_density_max 0.317 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2302 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0330 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+1.3245P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.0939 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2154 _reflns_number_total 2302 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01946e2.cif _cod_data_source_block 12b _cod_original_cell_volume 2319.05(7) _cod_database_code 7158383 _chemical_oxdiff_formula 'C25 H22 N4 O S2' _chemical_oxdiff_usercomment 'Rebecca Fuller - Tasmania' _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B) 2.b Aromatic/amide H refined with riding coordinates: C9(H9), C5(H5), C1(H1), C11(H11), C3(H3), C12(H12), C2(H2), C13(H13), C4(H4) ; _shelx_res_file ; TITL bof19b_auto_a.res in C2/c bof19b_auto.res created by SHELXL-2018/3 at 09:15:23 on 03-Sep-2021 REM Old TITL BOF19b_auto in C2/c REM SHELXT solution in C2/c: R1 0.087, Rweak 0.067, Alpha 0.018 REM 0.520 for 116 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N4 O S2 CELL 1.54184 18.9089 11.613 10.5619 90 90.812 90 ZERR 4 0.0003 0.0002 0.0002 0 0.002 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 100 88 16 4 8 L.S. 20 PLAN 1 TEMP -173 CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.057700 1.324500 FVAR 0.37362 S1 5 0.387560 0.626848 0.703007 11.00000 0.02657 0.02251 = 0.02655 -0.00262 -0.00141 0.00162 O1 4 0.500000 0.116660 0.750000 10.50000 0.02655 0.01559 = 0.03011 0.00000 -0.00041 0.00000 N1 3 0.481490 0.282326 0.641692 11.00000 0.02107 0.01538 = 0.02296 -0.00115 -0.00118 0.00070 N2 3 0.451372 0.389678 0.654129 11.00000 0.01746 0.01525 = 0.02514 -0.00029 -0.00101 -0.00008 C8 1 0.500000 0.221447 0.750000 10.50000 0.01492 0.01886 = 0.02416 0.00000 0.00120 0.00000 C9 1 0.428678 0.440474 0.553594 11.00000 0.01994 0.01927 = 0.02269 -0.00030 -0.00055 -0.00292 AFIX 43 H9 2 0.433040 0.403930 0.473612 11.00000 -1.20000 AFIX 0 C6 1 0.412903 0.157223 0.489160 11.00000 0.02049 0.01414 = 0.02465 0.00276 -0.00192 0.00014 C7 1 0.481823 0.217373 0.523403 11.00000 0.01988 0.01778 = 0.02374 -0.00224 0.00181 -0.00090 AFIX 23 H7A 2 0.519745 0.158738 0.528988 11.00000 -1.20000 H7B 2 0.493856 0.270672 0.453797 11.00000 -1.20000 AFIX 0 C10 1 0.396436 0.553323 0.561628 11.00000 0.01794 0.01869 = 0.02512 0.00102 -0.00011 -0.00270 C5 1 0.350200 0.173750 0.553552 11.00000 0.02310 0.02124 = 0.03304 -0.00235 0.00183 -0.00087 AFIX 43 H5 2 0.348664 0.226572 0.622140 11.00000 -1.20000 AFIX 0 C1 1 0.414070 0.079400 0.388927 11.00000 0.02706 0.01918 = 0.02849 -0.00263 0.00266 -0.00321 AFIX 43 H1 2 0.456726 0.067380 0.344350 11.00000 -1.20000 AFIX 0 C11 1 0.368908 0.616147 0.462313 11.00000 0.02071 0.02251 = 0.02825 0.00442 -0.00047 -0.00224 AFIX 43 H11 2 0.369129 0.590714 0.376831 11.00000 -1.20000 AFIX 0 C3 1 0.290946 0.036273 0.417417 11.00000 0.02604 0.02135 = 0.04478 0.00394 -0.00861 -0.00749 AFIX 43 H3 2 0.249366 -0.004285 0.392667 11.00000 -1.20000 AFIX 0 C12 1 0.340160 0.722929 0.501090 11.00000 0.02011 0.02241 = 0.04093 0.00732 -0.00188 0.00057 AFIX 43 H12 2 0.318863 0.776639 0.444431 11.00000 -1.20000 AFIX 0 C2 1 0.353506 0.019165 0.353451 11.00000 0.03782 0.02036 = 0.03571 -0.00399 -0.00405 -0.00745 AFIX 43 H2 2 0.354999 -0.033924 0.285110 11.00000 -1.20000 AFIX 0 C13 1 0.346299 0.740259 0.627725 11.00000 0.02292 0.02115 = 0.04413 -0.00154 0.00075 0.00237 AFIX 43 H13 2 0.329769 0.807113 0.669867 11.00000 -1.20000 AFIX 0 C4 1 0.289477 0.113080 0.517889 11.00000 0.01978 0.02562 = 0.04677 0.00271 0.00118 -0.00047 AFIX 43 H4 2 0.246831 0.124431 0.562702 11.00000 -1.20000 AFIX 0 HKLF 4 REM bof19b_auto_a.res in C2/c REM wR2 = 0.0939, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0330 for 2154 Fo > 4sig(Fo) and 0.0348 for all 2302 data REM 146 parameters refined using 0 restraints END WGHT 0.0577 1.3245 REM Highest difference peak 0.317, deepest hole -0.264, 1-sigma level 0.047 Q1 1 0.4429 0.6287 0.7048 11.00000 0.05 0.32 ; _shelx_res_checksum 56720 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.381 _oxdiff_exptl_absorpt_empirical_full_min 0.815 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 0.38756(2) 0.62685(3) 0.70301(3) 0.02523(13) Uani 1 1 d . . . . . O1 O 0.500000 0.11666(10) 0.750000 0.0241(3) Uani 1 2 d S T P . . N1 N 0.48149(5) 0.28233(9) 0.64169(10) 0.0198(2) Uani 1 1 d . . . . . N2 N 0.45137(6) 0.38968(9) 0.65413(10) 0.0193(2) Uani 1 1 d . . . . . C8 C 0.500000 0.22145(15) 0.750000 0.0193(4) Uani 1 2 d S T P . . C9 C 0.42868(6) 0.44047(11) 0.55359(12) 0.0206(3) Uani 1 1 d . . . . . H9 H 0.433040 0.403930 0.473612 0.025 Uiso 1 1 calc R U . . . C6 C 0.41290(7) 0.15722(10) 0.48916(12) 0.0198(3) Uani 1 1 d . . . . . C7 C 0.48182(6) 0.21737(11) 0.52340(12) 0.0205(3) Uani 1 1 d . . . . . H7A H 0.519745 0.158738 0.528988 0.025 Uiso 1 1 calc R U . . . H7B H 0.493856 0.270672 0.453797 0.025 Uiso 1 1 calc R U . . . C10 C 0.39644(6) 0.55332(11) 0.56163(12) 0.0206(3) Uani 1 1 d . . . . . C5 C 0.35020(7) 0.17375(11) 0.55355(13) 0.0258(3) Uani 1 1 d . . . . . H5 H 0.348664 0.226572 0.622140 0.031 Uiso 1 1 calc R U . . . C1 C 0.41407(7) 0.07940(11) 0.38893(13) 0.0249(3) Uani 1 1 d . . . . . H1 H 0.456726 0.067380 0.344350 0.030 Uiso 1 1 calc R U . . . C11 C 0.36891(7) 0.61615(11) 0.46231(13) 0.0238(3) Uani 1 1 d . . . . . H11 H 0.369129 0.590714 0.376831 0.029 Uiso 1 1 calc R U . . . C3 C 0.29095(8) 0.03627(12) 0.41742(15) 0.0308(3) Uani 1 1 d . . . . . H3 H 0.249366 -0.004285 0.392667 0.037 Uiso 1 1 calc R U . . . C12 C 0.34016(7) 0.72293(12) 0.50109(14) 0.0278(3) Uani 1 1 d . . . . . H12 H 0.318863 0.776639 0.444431 0.033 Uiso 1 1 calc R U . . . C2 C 0.35351(8) 0.01917(12) 0.35345(14) 0.0313(3) Uani 1 1 d . . . . . H2 H 0.354999 -0.033924 0.285110 0.038 Uiso 1 1 calc R U . . . C13 C 0.34630(7) 0.74026(12) 0.62773(15) 0.0294(3) Uani 1 1 d . . . . . H13 H 0.329769 0.807113 0.669867 0.035 Uiso 1 1 calc R U . . . C4 C 0.28948(8) 0.11308(12) 0.51789(16) 0.0307(3) Uani 1 1 d . . . . . H4 H 0.246831 0.124431 0.562702 0.037 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 0.0266(2) 0.0225(2) 0.0265(2) -0.00262(11) -0.00141(14) 0.00162(11) O1 0.0266(7) 0.0156(6) 0.0301(7) 0.000 -0.0004(5) 0.000 N1 0.0211(5) 0.0154(5) 0.0230(5) -0.0011(4) -0.0012(4) 0.0007(4) N2 0.0175(5) 0.0152(5) 0.0251(5) -0.0003(4) -0.0010(4) -0.0001(4) C8 0.0149(8) 0.0189(8) 0.0242(8) 0.000 0.0012(6) 0.000 C9 0.0199(6) 0.0193(6) 0.0227(6) -0.0003(5) -0.0006(5) -0.0029(5) C6 0.0205(6) 0.0141(5) 0.0247(6) 0.0028(5) -0.0019(5) 0.0001(5) C7 0.0199(6) 0.0178(6) 0.0237(6) -0.0022(5) 0.0018(5) -0.0009(5) C10 0.0179(6) 0.0187(6) 0.0251(6) 0.0010(5) -0.0001(5) -0.0027(5) C5 0.0231(7) 0.0212(6) 0.0330(7) -0.0023(5) 0.0018(5) -0.0009(5) C1 0.0271(7) 0.0192(6) 0.0285(7) -0.0026(5) 0.0027(5) -0.0032(5) C11 0.0207(6) 0.0225(6) 0.0282(7) 0.0044(5) -0.0005(5) -0.0022(5) C3 0.0260(7) 0.0214(7) 0.0448(8) 0.0039(6) -0.0086(6) -0.0075(5) C12 0.0201(6) 0.0224(6) 0.0409(8) 0.0073(6) -0.0019(6) 0.0006(5) C2 0.0378(8) 0.0204(6) 0.0357(7) -0.0040(5) -0.0040(6) -0.0075(6) C13 0.0229(7) 0.0212(6) 0.0441(8) -0.0015(6) 0.0008(6) 0.0024(5) C4 0.0198(7) 0.0256(7) 0.0468(9) 0.0027(6) 0.0012(6) -0.0005(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 C13 S1 C10 91.59(7) . . ? N2 N1 C8 118.88(10) . . ? N2 N1 C7 123.79(10) . . ? C8 N1 C7 116.04(10) . . ? C9 N2 N1 118.10(11) . . ? O1 C8 N1 120.68(8) . . ? O1 C8 N1 120.68(7) . 2_656 ? N1 C8 N1 118.63(15) 2_656 . ? N2 C9 H9 119.9 . . ? N2 C9 C10 120.24(12) . . ? C10 C9 H9 119.9 . . ? C5 C6 C7 123.77(12) . . ? C5 C6 C1 119.01(12) . . ? C1 C6 C7 117.20(11) . . ? N1 C7 C6 115.32(10) . . ? N1 C7 H7A 108.4 . . ? N1 C7 H7B 108.4 . . ? C6 C7 H7A 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C9 C10 S1 122.89(10) . . ? C11 C10 S1 110.88(10) . . ? C11 C10 C9 126.22(12) . . ? C6 C5 H5 119.9 . . ? C6 C5 C4 120.23(13) . . ? C4 C5 H5 119.9 . . ? C6 C1 H1 119.7 . . ? C2 C1 C6 120.67(13) . . ? C2 C1 H1 119.7 . . ? C10 C11 H11 123.6 . . ? C10 C11 C12 112.76(13) . . ? C12 C11 H11 123.6 . . ? C2 C3 H3 120.3 . . ? C2 C3 C4 119.48(13) . . ? C4 C3 H3 120.3 . . ? C11 C12 H12 123.6 . . ? C13 C12 C11 112.78(12) . . ? C13 C12 H12 123.6 . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.19(13) . . ? C3 C2 H2 119.9 . . ? S1 C13 H13 124.0 . . ? C12 C13 S1 111.98(11) . . ? C12 C13 H13 124.0 . . ? C5 C4 H4 119.8 . . ? C3 C4 C5 120.42(14) . . ? C3 C4 H4 119.8 . . ? 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 C10 1.7303(13) . ? S1 C13 1.7199(14) . ? O1 C8 1.217(2) . ? N1 N2 1.3777(14) . ? N1 C8 1.3855(14) . ? N1 C7 1.4595(15) . ? N2 C9 1.2832(17) . ? C9 H9 0.9500 . ? C9 C10 1.4484(18) . ? C6 C7 1.5178(16) . ? C6 C5 1.3885(19) . ? C6 C1 1.3924(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C10 C11 1.3741(18) . ? C5 H5 0.9500 . ? C5 C4 1.3944(19) . ? C1 H1 0.9500 . ? C1 C2 1.3889(19) . ? C11 H11 0.9500 . ? C11 C12 1.4168(19) . ? C3 H3 0.9500 . ? C3 C2 1.385(2) . ? C3 C4 1.387(2) . ? C12 H12 0.9500 . ? C12 C13 1.356(2) . ? C2 H2 0.9500 . ? C13 H13 0.9500 . ? C4 H4 0.9500 . ? 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 S1 C10 C11 C12 -0.57(15) . . . . ? N1 N2 C9 C10 179.86(10) . . . . ? N2 N1 C8 O1 150.98(7) . . . . ? N2 N1 C8 N1 -29.02(7) . . . 2_656 ? N2 N1 C7 C6 -78.22(14) . . . . ? N2 C9 C10 S1 0.96(17) . . . . ? N2 C9 C10 C11 -178.75(12) . . . . ? C8 N1 N2 C9 -173.79(10) . . . . ? C8 N1 C7 C6 88.60(12) . . . . ? C9 C10 C11 C12 179.17(12) . . . . ? C6 C5 C4 C3 -0.4(2) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? C7 N1 N2 C9 -7.32(17) . . . . ? C7 N1 C8 O1 -16.52(11) . . . . ? C7 N1 C8 N1 163.48(11) . . . 2_656 ? C7 C6 C5 C4 -178.52(12) . . . . ? C7 C6 C1 C2 178.70(12) . . . . ? C10 S1 C13 C12 -0.41(11) . . . . ? C10 C11 C12 C13 0.27(17) . . . . ? C5 C6 C7 N1 8.78(17) . . . . ? C5 C6 C1 C2 0.1(2) . . . . ? C1 C6 C7 N1 -169.75(11) . . . . ? C1 C6 C5 C4 0.0(2) . . . . ? C11 C12 C13 S1 0.16(15) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C13 S1 C10 C9 -179.19(11) . . . . ? C13 S1 C10 C11 0.56(10) . . . . ? C4 C3 C2 C1 -0.7(2) . . . . ?