#------------------------------------------------------------------------------ #$Date: 2019-11-08 03:01:04 +0200 (Fri, 08 Nov 2019) $ #$Revision: 224942 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058768.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_7058768 loop_ _publ_author_name 'Hayashi, Satoko' 'Uegaito, Manabu' 'Nishide, Taro' 'Tanaka, Eiichiro' 'Nakanishi, Waro' 'Sasamori, Takahiro' 'Tokitoh, Norihiro' 'Minoura, Mao' _publ_section_title ; Nature of the E⋯E′ interactions (E, E′ = O, S, Se, and Te) at naphthalene 1,8-positions with fine details of the structures: experimental and theoretical investigations ; _journal_issue 36 _journal_name_full 'New Journal of Chemistry' _journal_page_first 14224 _journal_paper_doi 10.1039/C9NJ02198A _journal_volume 43 _journal_year 2019 _chemical_formula_moiety 'C22 H16 O S' _chemical_formula_sum 'C22 H16 O S' _chemical_formula_weight 328.41 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-07-25 deposited with the CCDC. 2019-08-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.9933(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2047(2) _cell_length_b 15.2729(3) _cell_length_c 13.0590(3) _cell_measurement_reflns_used 14140 _cell_measurement_temperature 103(2) _cell_measurement_theta_max 25.5 _cell_measurement_theta_min 2.82 _cell_volume 1634.18(6) _computing_cell_refinement CrystalClear _computing_data_collection CrystalClear _computing_data_reduction CrystalClear _computing_molecular_graphics 'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)' _computing_publication_material 'Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 103(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_unetI/netI 0.0244 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14140 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.240 _diffrn_reflns_theta_max 25.496 _diffrn_reflns_theta_min 2.821 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.335 _exptl_crystal_description prismatic _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.605 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3020 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0357 _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^)+(0.0503P)^2^+0.8980P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0966 _refine_ls_wR_factor_ref 0.0993 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2668 _reflns_number_total 3020 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj02198a2.cif _cod_data_source_block 3a_PhO-PhS-Nap _cod_depositor_comments 'Adding full bibliography for 7058768--7058773.cif.' _cod_database_code 7058768 _shelx_shelxl_version_number 2014/7 _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 0.942 _shelx_estimated_absorpt_t_max 0.980 _shelx_res_file ; 3a_re.res created by SHELXL-2014/7 TITL 3a_re REM Yadorkari-X generated CELL 0.71069 8.2047 15.2729 13.0590 90.0000 92.9933 90.0000 ZERR 4.0 0.0002 0.0003 0.0003 0.0000 0.0008 0.0000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z REM SPGR P21/c monoclinic SFAC C H O S UNIT 88 64 4 4 SIZE 0.30 0.20 0.10 TEMP -170.0 L.S. 10 FMAP 2 PLAN -25 ACTA CONF LIST 4 WPDB -1 BOND $H MERG 2 OMIT -10.000000 51.000000 OMIT 0 1 1 OMIT -1 3 1 OMIT -1 0 2 OMIT 1 1 2 OMIT 2 1 1 OMIT 2 2 1 OMIT 0 4 0 OMIT 3 0 2 OMIT 1 2 2 OMIT 2 2 2 OMIT 0 2 2 OMIT 0 2 0 WGHT 0.050300 0.898000 FVAR 6.94827 S1 4 0.132621 -0.090877 0.684001 11.00000 0.02334 0.01573 = 0.01889 -0.00066 0.00346 -0.00099 C1 1 0.183137 -0.169552 0.590610 11.00000 0.01872 0.01698 = 0.01963 -0.00040 0.00384 -0.00115 C2 1 0.095183 -0.175715 0.496493 11.00000 0.02052 0.02064 = 0.02188 0.00113 0.00099 0.00071 AFIX 43 H1 2 0.014518 -0.133187 0.477821 11.00000 -1.20000 AFIX 0 C3 1 0.125887 -0.244217 0.430146 11.00000 0.02694 0.02607 = 0.02135 -0.00296 0.00252 -0.00409 AFIX 43 H2 2 0.068099 -0.247705 0.365315 11.00000 -1.20000 AFIX 0 C4 1 0.241071 -0.307633 0.458559 11.00000 0.03355 0.01931 = 0.02836 -0.00299 0.01162 -0.00144 AFIX 43 H3 2 0.260657 -0.354953 0.413613 11.00000 -1.20000 AFIX 0 C5 1 0.327072 -0.301883 0.552115 11.00000 0.02917 0.02093 = 0.03094 0.00555 0.01009 0.00741 AFIX 43 H4 2 0.405253 -0.345524 0.571442 11.00000 -1.20000 AFIX 0 C6 1 0.299932 -0.232691 0.618084 11.00000 0.02219 0.02504 = 0.02026 0.00497 0.00161 0.00173 AFIX 43 H5 2 0.360846 -0.228422 0.681779 11.00000 -1.20000 AFIX 0 C7 1 0.211224 0.009289 0.635505 11.00000 0.01391 0.01601 = 0.02050 0.00183 -0.00144 0.00078 C8 1 0.283633 0.013092 0.542704 11.00000 0.01912 0.01855 = 0.02122 -0.00063 -0.00041 0.00229 AFIX 43 H6 2 0.287753 -0.038338 0.502005 11.00000 -1.20000 AFIX 0 C9 1 0.351692 0.091203 0.506592 11.00000 0.01827 0.02558 = 0.02033 0.00423 0.00331 0.00388 AFIX 43 H7 2 0.399351 0.091900 0.441844 11.00000 -1.20000 AFIX 0 C10 1 0.349684 0.165710 0.563786 11.00000 0.01799 0.01960 = 0.02494 0.00614 0.00228 -0.00074 AFIX 43 H8 2 0.398710 0.217598 0.539641 11.00000 -1.20000 AFIX 0 C11 1 0.274550 0.166220 0.659488 11.00000 0.01405 0.01748 = 0.02150 0.00260 -0.00175 0.00047 C12 1 0.269889 0.244426 0.717781 11.00000 0.02067 0.01705 = 0.02704 0.00182 -0.00200 -0.00208 AFIX 43 H9 2 0.321412 0.295606 0.693698 11.00000 -1.20000 AFIX 0 C13 1 0.192754 0.247584 0.807881 11.00000 0.02438 0.01784 = 0.02527 -0.00337 -0.00408 0.00116 AFIX 43 H10 2 0.190072 0.300624 0.845757 11.00000 -1.20000 AFIX 0 C14 1 0.117332 0.171852 0.844241 11.00000 0.02141 0.02287 = 0.01780 -0.00103 -0.00109 0.00267 AFIX 43 H11 2 0.062075 0.174021 0.906332 11.00000 -1.20000 AFIX 0 C15 1 0.123135 0.095156 0.790702 11.00000 0.01420 0.01863 = 0.01886 0.00409 -0.00236 -0.00116 C16 1 0.201378 0.087918 0.696012 11.00000 0.01307 0.01679 = 0.01839 0.00207 -0.00284 0.00104 O1 3 0.056851 0.020081 0.834483 11.00000 0.01563 0.02521 = 0.01611 0.00187 0.00162 -0.00310 C17 1 -0.113470 0.012616 0.830798 11.00000 0.01800 0.01758 = 0.01718 -0.00410 0.00232 0.00093 C18 1 -0.212219 0.045441 0.750769 11.00000 0.02276 0.02679 = 0.01666 0.00122 0.00237 0.00214 AFIX 43 H12 2 -0.166358 0.077101 0.696658 11.00000 -1.20000 AFIX 0 C19 1 -0.379514 0.031423 0.750687 11.00000 0.02236 0.02723 = 0.02342 -0.00160 -0.00181 0.00323 AFIX 43 H13 2 -0.448344 0.053310 0.695780 11.00000 -1.20000 AFIX 0 C20 1 -0.447240 -0.014280 0.830082 11.00000 0.01879 0.02135 = 0.03286 -0.00483 0.00204 -0.00184 AFIX 43 H14 2 -0.561785 -0.023475 0.829713 11.00000 -1.20000 AFIX 0 C21 1 -0.346054 -0.046368 0.909909 11.00000 0.02900 0.01820 = 0.02519 -0.00014 0.00675 -0.00385 AFIX 43 H15 2 -0.391769 -0.077327 0.964609 11.00000 -1.20000 AFIX 0 C22 1 -0.178489 -0.033549 0.910405 11.00000 0.02617 0.01677 = 0.01800 0.00005 -0.00099 0.00036 AFIX 43 H16 2 -0.109222 -0.056158 0.964679 11.00000 -1.20000 AFIX 0 HKLF 4 REM 3a_re REM R1 = 0.0357 for 2668 Fo > 4sig(Fo) and 0.0404 for all 3020 data REM 217 parameters refined using 0 restraints END WGHT 0.0503 0.8980 REM Highest difference peak 0.605, deepest hole -0.424, 1-sigma level 0.061 Q1 1 0.0786 -0.0335 0.8359 11.00000 0.05 0.61 Q2 1 0.1569 -0.0396 0.6434 11.00000 0.05 0.25 Q3 1 -0.1687 0.0456 0.8057 11.00000 0.05 0.24 Q4 1 -0.3897 -0.0162 0.8854 11.00000 0.05 0.23 Q5 1 0.1903 0.0451 0.6656 11.00000 0.05 0.23 Q6 1 -0.1550 -0.0007 0.8791 11.00000 0.05 0.21 Q7 1 0.1476 -0.4137 0.3917 11.00000 0.05 0.21 Q8 1 0.2715 -0.2962 0.5900 11.00000 0.05 0.20 Q9 1 0.2915 0.1998 0.6970 11.00000 0.05 0.20 Q10 1 0.2009 -0.2665 0.4441 11.00000 0.05 0.19 Q11 1 0.1620 -0.2837 0.4573 11.00000 0.05 0.19 Q12 1 0.2812 0.2351 0.7737 11.00000 0.05 0.19 Q13 1 0.3283 -0.2652 0.5789 11.00000 0.05 0.19 Q14 1 0.2465 0.1299 0.6757 11.00000 0.05 0.19 Q15 1 -0.2765 -0.0258 0.9144 11.00000 0.05 0.19 Q16 1 0.1552 0.1307 0.8276 11.00000 0.05 0.19 Q17 1 0.1861 -0.1168 0.6009 11.00000 0.05 0.18 Q18 1 -0.2025 0.0687 0.7464 11.00000 0.05 0.17 Q19 1 -0.1495 -0.0305 0.8450 11.00000 0.05 0.17 Q20 1 0.0379 -0.0366 0.6433 11.00000 0.05 0.17 Q21 1 -0.4125 0.0145 0.8047 11.00000 0.05 0.17 Q22 1 0.3132 0.1640 0.6190 11.00000 0.05 0.17 Q23 1 0.5135 0.0958 0.3400 11.00000 0.05 0.17 Q24 1 -0.1170 -0.0854 0.4286 11.00000 0.05 0.16 Q25 1 -0.2727 0.0693 0.7676 11.00000 0.05 0.16 ; _shelx_res_checksum 59252 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 S1 S 0.13262(5) -0.09088(3) 0.68400(3) 0.01923(14) Uani 1 1 d . . C1 C 0.18314(19) -0.16955(10) 0.59061(12) 0.0183(3) Uani 1 1 d . . C2 C 0.0952(2) -0.17571(11) 0.49649(13) 0.0210(4) Uani 1 1 d . . H1 H 0.0145 -0.1332 0.4778 0.025 Uiso 1 1 calc R U C3 C 0.1259(2) -0.24422(11) 0.43015(13) 0.0247(4) Uani 1 1 d . . H2 H 0.0681 -0.2477 0.3653 0.030 Uiso 1 1 calc R U C4 C 0.2411(2) -0.30763(11) 0.45856(14) 0.0267(4) Uani 1 1 d . . H3 H 0.2607 -0.3550 0.4136 0.032 Uiso 1 1 calc R U C5 C 0.3271(2) -0.30188(11) 0.55211(14) 0.0267(4) Uani 1 1 d . . H4 H 0.4053 -0.3455 0.5714 0.032 Uiso 1 1 calc R U C6 C 0.2999(2) -0.23269(11) 0.61808(13) 0.0225(4) Uani 1 1 d . . H5 H 0.3608 -0.2284 0.6818 0.027 Uiso 1 1 calc R U C7 C 0.21122(19) 0.00929(10) 0.63551(12) 0.0169(3) Uani 1 1 d . . C8 C 0.28363(19) 0.01309(11) 0.54270(12) 0.0197(3) Uani 1 1 d . . H6 H 0.2878 -0.0383 0.5020 0.024 Uiso 1 1 calc R U C9 C 0.3517(2) 0.09120(11) 0.50659(13) 0.0213(4) Uani 1 1 d . . H7 H 0.3994 0.0919 0.4418 0.026 Uiso 1 1 calc R U C10 C 0.34968(19) 0.16571(11) 0.56379(13) 0.0208(4) Uani 1 1 d . . H8 H 0.3987 0.2176 0.5396 0.025 Uiso 1 1 calc R U C11 C 0.27455(18) 0.16622(10) 0.65949(12) 0.0178(3) Uani 1 1 d . . C12 C 0.2699(2) 0.24443(11) 0.71778(13) 0.0217(4) Uani 1 1 d . . H9 H 0.3214 0.2956 0.6937 0.026 Uiso 1 1 calc R U C13 C 0.1928(2) 0.24758(11) 0.80788(13) 0.0227(4) Uani 1 1 d . . H10 H 0.1901 0.3006 0.8458 0.027 Uiso 1 1 calc R U C14 C 0.1173(2) 0.17185(11) 0.84424(12) 0.0208(4) Uani 1 1 d . . H11 H 0.0621 0.1740 0.9063 0.025 Uiso 1 1 calc R U C15 C 0.12313(19) 0.09516(10) 0.79070(12) 0.0173(3) Uani 1 1 d . . C16 C 0.20138(18) 0.08792(10) 0.69601(12) 0.0162(3) Uani 1 1 d . . O1 O 0.05685(13) 0.02008(7) 0.83448(8) 0.0190(3) Uani 1 1 d . . C17 C -0.11347(19) 0.01262(10) 0.83080(12) 0.0175(3) Uani 1 1 d . . C18 C -0.2122(2) 0.04544(11) 0.75077(12) 0.0220(4) Uani 1 1 d . . H12 H -0.1664 0.0771 0.6967 0.026 Uiso 1 1 calc R U C19 C -0.3795(2) 0.03142(11) 0.75069(13) 0.0244(4) Uani 1 1 d . . H13 H -0.4483 0.0533 0.6958 0.029 Uiso 1 1 calc R U C20 C -0.4472(2) -0.01428(11) 0.83008(14) 0.0243(4) Uani 1 1 d . . H14 H -0.5618 -0.0235 0.8297 0.029 Uiso 1 1 calc R U C21 C -0.3461(2) -0.04637(11) 0.90991(13) 0.0239(4) Uani 1 1 d . . H15 H -0.3918 -0.0773 0.9646 0.029 Uiso 1 1 calc R U C22 C -0.1785(2) -0.03355(10) 0.91041(12) 0.0204(3) Uani 1 1 d . . H16 H -0.1092 -0.0562 0.9647 0.024 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 0.0233(2) 0.0157(2) 0.0189(2) -0.00066(14) 0.00346(16) -0.00099(15) C1 0.0187(8) 0.0170(8) 0.0196(8) -0.0004(6) 0.0038(6) -0.0012(6) C2 0.0205(8) 0.0206(8) 0.0219(8) 0.0011(6) 0.0010(6) 0.0007(7) C3 0.0269(9) 0.0261(9) 0.0214(9) -0.0030(7) 0.0025(7) -0.0041(7) C4 0.0335(10) 0.0193(8) 0.0284(9) -0.0030(7) 0.0116(8) -0.0014(7) C5 0.0292(9) 0.0209(9) 0.0309(10) 0.0056(7) 0.0101(8) 0.0074(7) C6 0.0222(8) 0.0250(9) 0.0203(8) 0.0050(7) 0.0016(7) 0.0017(7) C7 0.0139(7) 0.0160(8) 0.0205(8) 0.0018(6) -0.0014(6) 0.0008(6) C8 0.0191(8) 0.0185(8) 0.0212(8) -0.0006(6) -0.0004(6) 0.0023(6) C9 0.0183(8) 0.0256(9) 0.0203(8) 0.0042(7) 0.0033(6) 0.0039(6) C10 0.0180(8) 0.0196(8) 0.0249(8) 0.0061(7) 0.0023(6) -0.0007(6) C11 0.0140(7) 0.0175(8) 0.0215(8) 0.0026(6) -0.0017(6) 0.0005(6) C12 0.0207(8) 0.0171(8) 0.0270(9) 0.0018(7) -0.0020(7) -0.0021(6) C13 0.0244(9) 0.0178(8) 0.0253(9) -0.0034(7) -0.0041(7) 0.0012(7) C14 0.0214(8) 0.0229(8) 0.0178(8) -0.0010(6) -0.0011(6) 0.0027(7) C15 0.0142(7) 0.0186(8) 0.0189(8) 0.0041(6) -0.0024(6) -0.0012(6) C16 0.0131(7) 0.0168(8) 0.0184(8) 0.0021(6) -0.0028(6) 0.0010(6) O1 0.0156(5) 0.0252(6) 0.0161(5) 0.0019(4) 0.0016(4) -0.0031(4) C17 0.0180(8) 0.0176(8) 0.0172(8) -0.0041(6) 0.0023(6) 0.0009(6) C18 0.0228(9) 0.0268(9) 0.0167(8) 0.0012(7) 0.0024(6) 0.0021(7) C19 0.0224(9) 0.0272(9) 0.0234(9) -0.0016(7) -0.0018(7) 0.0032(7) C20 0.0188(8) 0.0214(8) 0.0329(10) -0.0048(7) 0.0020(7) -0.0018(7) C21 0.0290(9) 0.0182(8) 0.0252(9) -0.0001(7) 0.0067(7) -0.0039(7) C22 0.0262(9) 0.0168(8) 0.0180(8) 0.0001(6) -0.0010(6) 0.0004(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' 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 C1 S1 C7 103.54(7) C6 C1 C2 119.82(15) C6 C1 S1 118.25(12) C2 C1 S1 121.45(13) C3 C2 C1 119.84(15) C3 C2 H1 120.1 C1 C2 H1 120.1 C2 C3 C4 120.06(16) C2 C3 H2 120.0 C4 C3 H2 120.0 C5 C4 C3 120.04(16) C5 C4 H3 120.0 C3 C4 H3 120.0 C4 C5 C6 120.40(16) C4 C5 H4 119.8 C6 C5 H4 119.8 C5 C6 C1 119.83(16) C5 C6 H5 120.1 C1 C6 H5 120.1 C8 C7 C16 119.06(14) C8 C7 S1 121.82(12) C16 C7 S1 119.12(12) C7 C8 C9 121.77(15) C7 C8 H6 119.1 C9 C8 H6 119.1 C10 C9 C8 120.51(15) C10 C9 H7 119.7 C8 C9 H7 119.7 C9 C10 C11 120.32(15) C9 C10 H8 119.8 C11 C10 H8 119.8 C12 C11 C10 120.10(14) C12 C11 C16 120.10(15) C10 C11 C16 119.80(14) C13 C12 C11 121.26(15) C13 C12 H9 119.4 C11 C12 H9 119.4 C12 C13 C14 119.59(15) C12 C13 H10 120.2 C14 C13 H10 120.2 C15 C14 C13 120.31(16) C15 C14 H11 119.8 C13 C14 H11 119.8 C14 C15 O1 117.86(14) C14 C15 C16 122.63(14) O1 C15 C16 119.41(13) C15 C16 C11 116.08(14) C15 C16 C7 125.44(14) C11 C16 C7 118.48(14) C17 O1 C15 117.37(12) C18 C17 C22 121.21(15) C18 C17 O1 122.74(14) C22 C17 O1 115.99(14) C17 C18 C19 118.99(16) C17 C18 H12 120.5 C19 C18 H12 120.5 C18 C19 C20 120.69(16) C18 C19 H13 119.7 C20 C19 H13 119.7 C21 C20 C19 119.41(16) C21 C20 H14 120.3 C19 C20 H14 120.3 C20 C21 C22 120.47(16) C20 C21 H15 119.8 C22 C21 H15 119.8 C17 C22 C21 119.22(15) C17 C22 H16 120.4 C21 C22 H16 120.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.7765(16) S1 C7 1.7889(16) C1 C6 1.393(2) C1 C2 1.396(2) C2 C3 1.390(2) C2 H1 0.9500 C3 C4 1.390(3) C3 H2 0.9500 C4 C5 1.381(3) C4 H3 0.9500 C5 C6 1.389(2) C5 H4 0.9500 C6 H5 0.9500 C7 C8 1.378(2) C7 C16 1.442(2) C8 C9 1.409(2) C8 H6 0.9500 C9 C10 1.362(2) C9 H7 0.9500 C10 C11 1.422(2) C10 H8 0.9500 C11 C12 1.418(2) C11 C16 1.431(2) C12 C13 1.366(3) C12 H9 0.9500 C13 C14 1.406(2) C13 H10 0.9500 C14 C15 1.366(2) C14 H11 0.9500 C15 O1 1.4035(19) C15 C16 1.427(2) O1 C17 1.4004(19) C17 C18 1.383(2) C17 C22 1.386(2) C18 C19 1.389(2) C18 H12 0.9500 C19 C20 1.390(3) C19 H13 0.9500 C20 C21 1.388(3) C20 H14 0.9500 C21 C22 1.388(2) C21 H15 0.9500 C22 H16 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 C7 S1 C1 C6 111.69(13) C7 S1 C1 C2 -76.27(15) C6 C1 C2 C3 -0.8(2) S1 C1 C2 C3 -172.67(13) C1 C2 C3 C4 1.6(3) C2 C3 C4 C5 -1.0(3) C3 C4 C5 C6 -0.4(3) C4 C5 C6 C1 1.2(3) C2 C1 C6 C5 -0.6(2) S1 C1 C6 C5 171.55(13) C1 S1 C7 C8 2.81(15) C1 S1 C7 C16 -176.00(12) C16 C7 C8 C9 1.6(2) S1 C7 C8 C9 -177.26(12) C7 C8 C9 C10 0.9(2) C8 C9 C10 C11 -1.8(2) C9 C10 C11 C12 -178.73(15) C9 C10 C11 C16 0.3(2) C10 C11 C12 C13 177.32(15) C16 C11 C12 C13 -1.7(2) C11 C12 C13 C14 0.5(2) C12 C13 C14 C15 1.0(2) C13 C14 C15 O1 175.16(14) C13 C14 C15 C16 -1.2(2) C14 C15 C16 C11 0.0(2) O1 C15 C16 C11 -176.32(13) C14 C15 C16 C7 -179.68(15) O1 C15 C16 C7 4.0(2) C12 C11 C16 C15 1.4(2) C10 C11 C16 C15 -177.60(14) C12 C11 C16 C7 -178.88(14) C10 C11 C16 C7 2.1(2) C8 C7 C16 C15 176.69(15) S1 C7 C16 C15 -4.5(2) C8 C7 C16 C11 -3.0(2) S1 C7 C16 C11 175.84(11) C14 C15 O1 C17 76.08(17) C16 C15 O1 C17 -107.41(16) C15 O1 C17 C18 32.7(2) C15 O1 C17 C22 -150.15(14) C22 C17 C18 C19 -0.1(2) O1 C17 C18 C19 176.86(15) C17 C18 C19 C20 0.5(3) C18 C19 C20 C21 -0.2(3) C19 C20 C21 C22 -0.4(3) C18 C17 C22 C21 -0.5(2) O1 C17 C22 C21 -177.68(14) C20 C21 C22 C17 0.8(2)