#------------------------------------------------------------------------------ #$Date: 2021-08-04 14:09:36 +0300 (Wed, 04 Aug 2021) $ #$Revision: 267936 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564320.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_1564320 loop_ _publ_author_name 'Xu, Zhen' 'Climent, Cl\`audia' 'Brown, Christopher M.' 'Hean, Duane' 'Bardeen, Christopher J.' 'Casanova, David' 'Wolf, Michael O.' _publ_section_title ; Controlling ultralong room temperature phosphorescence in organic compounds with sulfur oxidation state. ; _journal_issue 1 _journal_name_full 'Chemical science' _journal_page_first 188 _journal_page_last 195 _journal_paper_doi 10.1039/d0sc04715e _journal_volume 12 _journal_year 2020 _chemical_formula_moiety 'C36 H24 N2 O2 S' _chemical_formula_sum 'C36 H24 N2 O2 S' _chemical_formula_weight 548.63 _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 2019-10-21 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-08-20 deposited with the CCDC. 2020-10-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 128.655(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 28.655(5) _cell_length_b 5.5039(11) _cell_length_c 20.506(4) _cell_measurement_reflns_used 3280 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 26.506 _cell_measurement_theta_min 2.856 _cell_volume 2525.6(9) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.15 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_unetI/netI 0.0630 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 9461 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.534 _diffrn_reflns_theta_min 1.820 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1915 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.8550. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.443 _exptl_crystal_description needle _exptl_crystal_F_000 1144 _exptl_crystal_size_max 0.309 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.285 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2616 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0454 _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^)+(0.0413P)^2^+1.3158P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.1030 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1834 _reflns_number_total 2616 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc04715e2.cif _cod_data_source_block mw372_0m_a _cod_original_cell_volume 2525.6(8) _cod_database_code 1564320 _shelx_shelxl_version_number 2017/1 _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 0.992 _shelx_estimated_absorpt_t_min 0.950 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18) ; _shelx_res_file ; TITL mw372_0m_a.res in C2/c mw372_0m_a.res created by SHELXL-2017/1 at 13:55:04 on 21-Oct-2019 REM Old TITL mw372_0m in C2/c REM SHELXT solution in C2/c REM R1 0.124, Rweak 0.006, Alpha 0.039, Orientation as input REM Formula found by SHELXT: C36 N2 O2 S CELL 0.71073 28.6551 5.5039 20.5059 90 128.655 90 ZERR 4 0.0051 0.0011 0.0038 0 0.005 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 144 96 8 8 4 L.S. 10 PLAN 20 SIZE 0.05 0.09 0.309 TEMP -173 BOND $H LIST 4 fmap 2 acta REM REM REM WGHT 0.041300 1.315800 FVAR 0.28981 S1 5 0.500000 -0.182388 0.250000 10.50000 0.02147 0.01457 = 0.01097 0.00000 0.00989 0.00000 O1 4 0.460252 -0.314628 0.256846 11.00000 0.02799 0.02018 = 0.01693 -0.00246 0.01451 -0.00780 N1 3 0.648807 0.437448 0.552122 11.00000 0.01760 0.02035 = 0.01398 -0.00385 0.00924 -0.00046 C1 1 0.701711 0.550085 0.579075 11.00000 0.01578 0.02134 = 0.01309 0.00171 0.00652 0.00275 C2 1 0.740256 0.488710 0.562930 11.00000 0.02083 0.02845 = 0.02120 -0.00368 0.01183 0.00220 AFIX 43 H2 2 0.731854 0.356372 0.527303 11.00000 -1.20000 AFIX 0 C3 1 0.791227 0.625215 0.600057 11.00000 0.02075 0.03411 = 0.02246 0.00359 0.01363 0.00412 AFIX 43 H3 2 0.818478 0.585399 0.589965 11.00000 -1.20000 AFIX 0 C4 1 0.803963 0.820297 0.652062 11.00000 0.02145 0.02819 = 0.01839 0.00268 0.00906 -0.00482 AFIX 43 H4 2 0.839171 0.913353 0.675992 11.00000 -1.20000 AFIX 0 C5 1 0.765992 0.878872 0.668936 11.00000 0.02744 0.02063 = 0.01348 -0.00005 0.00944 -0.00197 AFIX 43 H5 2 0.774615 1.011944 0.704427 11.00000 -1.20000 AFIX 0 C6 1 0.714861 0.741259 0.633499 11.00000 0.02017 0.01805 = 0.00918 0.00233 0.00562 0.00409 C7 1 0.668441 0.742245 0.641336 11.00000 0.01926 0.01716 = 0.00936 0.00246 0.00662 0.00276 C8 1 0.657646 0.891165 0.685666 11.00000 0.02830 0.01953 = 0.01222 -0.00066 0.00987 0.00039 AFIX 43 H8 2 0.684358 1.018996 0.719907 11.00000 -1.20000 AFIX 0 C9 1 0.607434 0.848353 0.678569 11.00000 0.02980 0.02748 = 0.01545 -0.00129 0.01554 0.00438 AFIX 43 H9 2 0.599248 0.948159 0.708150 11.00000 -1.20000 AFIX 0 C10 1 0.568544 0.661467 0.628823 11.00000 0.02346 0.02923 = 0.01785 0.00129 0.01386 0.00235 AFIX 43 H10 2 0.534268 0.635422 0.625332 11.00000 -1.20000 AFIX 0 C11 1 0.578197 0.511794 0.584116 11.00000 0.02208 0.01997 = 0.01493 -0.00249 0.00957 -0.00036 AFIX 43 H11 2 0.551247 0.384368 0.550029 11.00000 -1.20000 AFIX 0 C12 1 0.628588 0.555050 0.591026 11.00000 0.01883 0.01949 = 0.00912 0.00148 0.00681 0.00478 C13 1 0.613357 0.287984 0.480514 11.00000 0.01353 0.01670 = 0.01146 -0.00050 0.00563 0.00389 C14 1 0.582053 0.093139 0.478246 11.00000 0.02038 0.01662 = 0.01175 0.00310 0.00983 0.00345 AFIX 43 H14 2 0.585388 0.053991 0.526131 11.00000 -1.20000 AFIX 0 C15 1 0.545914 -0.045131 0.406701 11.00000 0.01896 0.01413 = 0.01449 0.00236 0.00972 0.00080 AFIX 43 H15 2 0.523591 -0.176762 0.404670 11.00000 -1.20000 AFIX 0 C16 1 0.542496 0.009885 0.337815 11.00000 0.01585 0.01569 = 0.01191 0.00066 0.00771 0.00311 C17 1 0.573744 0.202861 0.339615 11.00000 0.01975 0.01778 = 0.01321 0.00178 0.01114 0.00189 AFIX 43 H17 2 0.571297 0.238397 0.292223 11.00000 -1.20000 AFIX 0 C18 1 0.608586 0.344506 0.410224 11.00000 0.01882 0.01743 = 0.01795 0.00089 0.01199 -0.00024 AFIX 43 H18 2 0.629361 0.480596 0.411092 11.00000 -1.20000 AFIX 0 HKLF 4 REM mw372_0m_a.res in C2/c REM R1 = 0.0454 for 1834 Fo > 4sig(Fo) and 0.0802 for all 2616 data REM 186 parameters refined using 0 restraints END WGHT 0.0414 1.3019 REM Highest difference peak 0.285, deepest hole -0.500, 1-sigma level 0.058 Q1 1 0.5298 -0.0800 0.3018 11.00000 0.05 0.28 Q2 1 0.7100 0.6424 0.6079 11.00000 0.05 0.27 Q3 1 0.5968 0.5663 0.5695 11.00000 0.05 0.25 Q4 1 0.4572 -0.2006 0.2261 11.00000 0.05 0.24 Q5 1 0.6926 0.7785 0.6364 11.00000 0.05 0.24 Q6 1 0.5800 0.2218 0.4596 11.00000 0.05 0.23 Q7 1 0.7458 0.7459 0.6699 11.00000 0.05 0.23 Q8 1 0.5785 -0.0161 0.4434 11.00000 0.05 0.22 Q9 1 0.5513 0.0623 0.4396 11.00000 0.05 0.22 Q10 1 0.6043 0.2154 0.3829 11.00000 0.05 0.21 Q11 1 0.7206 0.8477 0.6170 11.00000 0.05 0.20 Q12 1 0.8005 1.2005 0.6577 11.00000 0.05 0.20 Q13 1 0.5861 -0.1182 0.3278 11.00000 0.05 0.20 Q14 1 0.6853 0.4605 0.5787 11.00000 0.05 0.20 Q15 1 0.6205 0.8946 0.6632 11.00000 0.05 0.20 Q16 1 0.4976 -0.1761 0.3798 11.00000 0.05 0.20 Q17 1 0.5410 0.6993 0.6112 11.00000 0.05 0.20 Q18 1 0.6190 0.1334 0.4973 11.00000 0.05 0.19 Q19 1 0.5024 0.0980 0.4884 11.00000 0.05 0.19 Q20 1 0.5409 0.3206 0.2696 11.00000 0.05 0.18 ; _shelx_res_checksum 3427 _olex2_submission_special_instructions 'No special instructions were received' 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 0.500000 -0.18239(14) 0.250000 0.0158(2) Uani 1 2 d S T P . . O1 O 0.46025(6) -0.3146(3) 0.25685(8) 0.0214(4) Uani 1 1 d . . . . . N1 N 0.64881(7) 0.4374(3) 0.55212(9) 0.0177(4) Uani 1 1 d . . . . . C1 C 0.70171(9) 0.5501(4) 0.57907(11) 0.0184(5) Uani 1 1 d . . . . . C2 C 0.74026(9) 0.4887(4) 0.56293(12) 0.0244(5) Uani 1 1 d . . . . . H2 H 0.731854 0.356372 0.527303 0.029 Uiso 1 1 calc R . . . . C3 C 0.79123(10) 0.6252(4) 0.60006(12) 0.0257(5) Uani 1 1 d . . . . . H3 H 0.818478 0.585399 0.589965 0.031 Uiso 1 1 calc R . . . . C4 C 0.80396(10) 0.8203(4) 0.65206(12) 0.0250(5) Uani 1 1 d . . . . . H4 H 0.839171 0.913353 0.675992 0.030 Uiso 1 1 calc R . . . . C5 C 0.76599(9) 0.8789(4) 0.66894(11) 0.0228(5) Uani 1 1 d . . . . . H5 H 0.774615 1.011944 0.704427 0.027 Uiso 1 1 calc R . . . . C6 C 0.71486(9) 0.7413(4) 0.63350(11) 0.0182(5) Uani 1 1 d . . . . . C7 C 0.66844(9) 0.7422(4) 0.64134(11) 0.0168(5) Uani 1 1 d . . . . . C8 C 0.65765(9) 0.8912(4) 0.68567(11) 0.0219(5) Uani 1 1 d . . . . . H8 H 0.684358 1.018996 0.719907 0.026 Uiso 1 1 calc R . . . . C9 C 0.60743(10) 0.8484(4) 0.67857(11) 0.0233(5) Uani 1 1 d . . . . . H9 H 0.599248 0.948159 0.708150 0.028 Uiso 1 1 calc R . . . . C10 C 0.56854(9) 0.6615(4) 0.62882(11) 0.0229(5) Uani 1 1 d . . . . . H10 H 0.534268 0.635422 0.625332 0.027 Uiso 1 1 calc R . . . . C11 C 0.57820(9) 0.5118(4) 0.58412(11) 0.0204(5) Uani 1 1 d . . . . . H11 H 0.551247 0.384368 0.550029 0.024 Uiso 1 1 calc R . . . . C12 C 0.62859(9) 0.5551(4) 0.59103(11) 0.0171(5) Uani 1 1 d . . . . . C13 C 0.61336(8) 0.2880(4) 0.48051(11) 0.0154(5) Uani 1 1 d . . . . . C14 C 0.58205(9) 0.0931(4) 0.47825(11) 0.0164(5) Uani 1 1 d . . . . . H14 H 0.585388 0.053991 0.526131 0.020 Uiso 1 1 calc R . . . . C15 C 0.54591(9) -0.0451(4) 0.40670(11) 0.0164(5) Uani 1 1 d . . . . . H15 H 0.523591 -0.176762 0.404670 0.020 Uiso 1 1 calc R . . . . C16 C 0.54250(9) 0.0099(4) 0.33782(11) 0.0151(5) Uani 1 1 d . . . . . C17 C 0.57374(9) 0.2029(4) 0.33962(11) 0.0163(5) Uani 1 1 d . . . . . H17 H 0.571297 0.238397 0.292223 0.020 Uiso 1 1 calc R . . . . C18 C 0.60859(9) 0.3445(4) 0.41022(11) 0.0177(5) Uani 1 1 d . . . . . H18 H 0.629361 0.480596 0.411092 0.021 Uiso 1 1 calc R . . . . 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 0.0215(4) 0.0146(4) 0.0110(3) 0.000 0.0099(3) 0.000 O1 0.0280(8) 0.0202(9) 0.0169(7) -0.0025(6) 0.0145(6) -0.0078(7) N1 0.0176(9) 0.0204(10) 0.0140(8) -0.0038(7) 0.0092(7) -0.0005(8) C1 0.0158(10) 0.0213(12) 0.0131(9) 0.0017(8) 0.0065(8) 0.0027(10) C2 0.0208(12) 0.0284(14) 0.0212(10) -0.0037(10) 0.0118(9) 0.0022(11) C3 0.0208(11) 0.0341(15) 0.0225(10) 0.0036(10) 0.0136(9) 0.0041(11) C4 0.0215(12) 0.0282(14) 0.0184(10) 0.0027(10) 0.0091(9) -0.0048(11) C5 0.0274(12) 0.0206(13) 0.0135(9) -0.0001(9) 0.0094(9) -0.0020(11) C6 0.0202(11) 0.0181(12) 0.0092(9) 0.0023(8) 0.0056(9) 0.0041(10) C7 0.0193(11) 0.0172(12) 0.0094(9) 0.0025(8) 0.0066(8) 0.0028(9) C8 0.0283(12) 0.0195(12) 0.0122(9) -0.0007(8) 0.0099(9) 0.0004(11) C9 0.0298(12) 0.0275(14) 0.0154(9) -0.0013(9) 0.0155(9) 0.0044(11) C10 0.0235(12) 0.0292(14) 0.0179(10) 0.0013(10) 0.0139(9) 0.0023(11) C11 0.0221(11) 0.0200(13) 0.0149(9) -0.0025(8) 0.0096(9) -0.0004(10) C12 0.0188(11) 0.0195(12) 0.0091(8) 0.0015(8) 0.0068(8) 0.0048(10) C13 0.0135(10) 0.0167(11) 0.0115(9) -0.0005(8) 0.0056(8) 0.0039(9) C14 0.0204(11) 0.0166(11) 0.0118(9) 0.0031(8) 0.0098(8) 0.0035(10) C15 0.0190(10) 0.0141(11) 0.0145(9) 0.0024(8) 0.0097(8) 0.0008(10) C16 0.0158(10) 0.0157(11) 0.0119(8) 0.0007(8) 0.0077(8) 0.0031(10) C17 0.0198(11) 0.0178(12) 0.0132(9) 0.0018(8) 0.0111(8) 0.0019(10) C18 0.0188(11) 0.0174(12) 0.0180(9) 0.0009(9) 0.0120(9) -0.0002(10) 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 O1 S1 O1 118.84(12) 2_655 . ? O1 S1 C16 106.83(8) . . ? O1 S1 C16 108.75(8) 2_655 . ? O1 S1 C16 108.75(8) . 2_655 ? O1 S1 C16 106.83(8) 2_655 2_655 ? C16 S1 C16 106.19(13) 2_655 . ? C1 N1 C12 107.61(16) . . ? C1 N1 C13 124.64(16) . . ? C12 N1 C13 125.07(17) . . ? N1 C1 C6 109.53(18) . . ? C2 C1 N1 129.21(19) . . ? C2 C1 C6 121.2(2) . . ? C1 C2 H2 121.1 . . ? C3 C2 C1 117.8(2) . . ? C3 C2 H2 121.1 . . ? C2 C3 H3 119.1 . . ? C2 C3 C4 121.7(2) . . ? C4 C3 H3 119.1 . . ? C3 C4 H4 119.8 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C4 C5 H5 120.5 . . ? C4 C5 C6 119.0(2) . . ? C6 C5 H5 120.5 . . ? C1 C6 C7 106.53(18) . . ? C5 C6 C1 119.86(19) . . ? C5 C6 C7 133.59(19) . . ? C8 C7 C6 132.3(2) . . ? C8 C7 C12 120.14(19) . . ? C12 C7 C6 107.53(17) . . ? C7 C8 H8 120.8 . . ? C9 C8 C7 118.3(2) . . ? C9 C8 H8 120.8 . . ? C8 C9 H9 119.6 . . ? C8 C9 C10 120.9(2) . . ? C10 C9 H9 119.6 . . ? C9 C10 H10 119.1 . . ? C11 C10 C9 121.9(2) . . ? C11 C10 H10 119.1 . . ? C10 C11 H11 121.3 . . ? C12 C11 C10 117.3(2) . . ? C12 C11 H11 121.3 . . ? C7 C12 N1 108.79(17) . . ? C11 C12 N1 129.71(19) . . ? C11 C12 C7 121.48(18) . . ? C14 C13 N1 121.13(17) . . ? C14 C13 C18 119.75(17) . . ? C18 C13 N1 119.08(19) . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.30(18) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 120.3 . . ? C14 C15 C16 119.4(2) . . ? C16 C15 H15 120.3 . . ? C15 C16 S1 118.27(16) . . ? C17 C16 S1 120.94(14) . . ? C17 C16 C15 120.72(18) . . ? C16 C17 H17 120.1 . . ? C16 C17 C18 119.87(18) . . ? C18 C17 H17 120.1 . . ? C13 C18 H18 120.0 . . ? C17 C18 C13 119.9(2) . . ? C17 C18 H18 120.0 . . ? 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 O1 1.4305(14) 2_655 ? S1 O1 1.4306(14) . ? S1 C16 1.7623(19) 2_655 ? S1 C16 1.7624(19) . ? N1 C1 1.393(3) . ? N1 C12 1.403(2) . ? N1 C13 1.415(2) . ? C1 C2 1.379(3) . ? C1 C6 1.403(3) . ? C2 H2 0.9500 . ? C2 C3 1.374(3) . ? C3 H3 0.9500 . ? C3 C4 1.392(3) . ? C4 H4 0.9500 . ? C4 C5 1.370(3) . ? C5 H5 0.9500 . ? C5 C6 1.385(3) . ? C6 C7 1.436(3) . ? C7 C8 1.395(3) . ? C7 C12 1.399(3) . ? C8 H8 0.9500 . ? C8 C9 1.373(3) . ? C9 H9 0.9500 . ? C9 C10 1.386(3) . ? C10 H10 0.9500 . ? C10 C11 1.383(3) . ? C11 H11 0.9500 . ? C11 C12 1.381(3) . ? C13 C14 1.380(3) . ? C13 C18 1.395(3) . ? C14 H14 0.9500 . ? C14 C15 1.381(3) . ? C15 H15 0.9500 . ? C15 C16 1.387(3) . ? C16 C17 1.375(3) . ? C17 H17 0.9500 . ? C17 C18 1.377(3) . ? C18 H18 0.9500 . ?