#------------------------------------------------------------------------------ #$Date: 2019-06-14 03:11:14 +0300 (Fri, 14 Jun 2019) $ #$Revision: 215939 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/14/1551409.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_1551409 loop_ _publ_author_name 'Teng, Qi' 'Thirupathi, Nuligonda' 'Tung, Chen-Ho' 'Xu, Zhenghu' _publ_section_title ; Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC02341K _journal_year 2019 _chemical_formula_moiety 'C16 H14 O2 S' _chemical_formula_sum 'C16 H14 O2 S' _chemical_formula_weight 270.33 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-05-25 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2018-06-06 deposited with the CCDC. 2019-06-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.8959(3) _cell_length_b 10.2141(4) _cell_length_c 19.1396(8) _cell_measurement_reflns_used 3189 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 76.1970 _cell_measurement_theta_min 4.3410 _cell_volume 1348.11(10) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 298(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 28.5714 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.968 _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 -118.00 -35.00 1.00 0.11 -- -48.45 -77.00-164.00 83 2 \w -156.00 -94.00 1.00 0.70 -- -86.25 -53.00 -33.00 62 3 \w 85.00 130.00 1.00 0.70 -- 107.75 -77.00-164.00 45 4 \w 35.00 106.00 1.00 0.70 -- 107.75 -96.00 100.00 71 5 \w 46.00 120.00 1.00 0.11 -- 48.45 19.00 90.00 74 6 \w 93.00 177.00 1.00 0.70 -- 107.75 125.00 -30.00 84 7 \w 38.00 71.00 1.00 0.70 -- 107.75 -19.00-150.00 33 8 \w 76.00 116.00 1.00 0.70 -- 107.75 -19.00-150.00 40 9 \w 95.00 175.00 1.00 0.70 -- 107.75 125.00 150.00 80 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'Mitegen 50um' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1825970000 _diffrn_orient_matrix_UB_12 0.0099451000 _diffrn_orient_matrix_UB_13 0.0460786000 _diffrn_orient_matrix_UB_21 0.0673778000 _diffrn_orient_matrix_UB_22 0.1352226000 _diffrn_orient_matrix_UB_23 0.0263045000 _diffrn_orient_matrix_UB_31 -0.1093349000 _diffrn_orient_matrix_UB_32 0.0663071000 _diffrn_orient_matrix_UB_33 -0.0605312000 _diffrn_radiation_collimation 0.3 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_unetI/netI 0.0407 _diffrn_reflns_Laue_measured_fraction_full 0.968 _diffrn_reflns_Laue_measured_fraction_max 0.968 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 5263 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 67.061 _diffrn_reflns_theta_max 67.061 _diffrn_reflns_theta_min 4.908 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 24.0 _diffrn_source_power 1.2 _diffrn_source_target Mo _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 2.085 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.332 _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.327 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details ; Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.029(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2312 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0527 _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^)+(0.1030P)^2^+0.8530P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1440 _refine_ls_wR_factor_ref 0.1821 _reflns_Friedel_coverage 0.685 _reflns_Friedel_fraction_full 0.948 _reflns_Friedel_fraction_max 0.948 _reflns_number_gt 2079 _reflns_number_total 2312 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc02341k2.cif _cod_data_source_block 180525a _cod_database_code 1551409 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula CO _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 0.979 _shelx_estimated_absorpt_t_min 0.903 _diffrn_oxdiff_ac3_digest_frames ; 01f5cff7a8522e95e54da3877783e526b800572907f ; _diffrn_oxdiff_ac3_digest_hkl ; 01df111c561538a5e1023adf1463007ac0e654 ; _reflns_odcompleteness_completeness 96.39 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C10(H10) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C11(H11A,H11B) 2.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C7(H7), C15(H15), C16(H16) 2.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _shelx_res_file ; 180525a.res created by SHELXL-2014/7 TITL 180525a_a.res in P2(1)2(1)2(1) REM Old TITL 180525a_a.res in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.357, Rweak 0.161, Alpha 0.002, Orientation as input REM Flack x = -0.485 ( 0.121 ) from Parsons' quotients REM Formula found by SHELXT: C16 O3 CELL 1.54184 6.8959 10.2141 19.1396 90 90 90 ZERR 4 0.0003 0.0004 0.0008 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O S UNIT 64 56 8 4 L.S. 10 PLAN 20 SIZE 0.05 0.02 0.01 TEMP 25(2) BOND $H list 4 fmap 2 acta SHEL 999 0.837 REM REM REM WGHT 0.103000 0.853000 FVAR 10.01640 C1 1 0.031660 0.179206 0.606551 11.00000 0.06856 0.04743 = 0.05195 0.01511 -0.00502 -0.00907 AFIX 43 H1 2 0.021949 0.116940 0.641830 11.00000 -1.20000 AFIX 0 C2 1 0.069781 0.149056 0.539562 11.00000 0.06669 0.04164 = 0.05911 -0.00419 -0.00745 0.00482 AFIX 43 H2 2 0.093223 0.063470 0.525296 11.00000 -1.20000 AFIX 0 C3 1 0.072224 0.258766 0.490428 11.00000 0.04637 0.03477 = 0.05222 0.01425 0.01289 0.00723 AFIX 43 H3 2 0.090172 0.255422 0.442303 11.00000 -1.20000 AFIX 0 C4 1 0.039915 0.375996 0.534073 11.00000 0.04202 0.03990 = 0.04459 0.00801 -0.00192 -0.00510 C5 1 0.030848 0.506757 0.509710 11.00000 0.05087 0.04584 = 0.05213 0.01344 0.00223 -0.00741 C6 1 0.025102 0.616921 0.488568 11.00000 0.05590 0.04933 = 0.04326 0.01402 -0.00125 -0.00349 C7 1 0.006899 0.750655 0.467431 11.00000 0.05681 0.03692 = 0.04846 0.00723 0.00657 0.00245 AFIX 43 H7 2 -0.015567 0.812357 0.502234 11.00000 -1.20000 AFIX 0 C8 1 0.019464 0.793909 0.402150 11.00000 0.03621 0.03051 = 0.04640 0.00383 0.00197 0.00190 C9 1 -0.018135 0.935569 0.381385 11.00000 0.05821 0.03512 = 0.04339 0.00313 0.00171 0.01110 AFIX 23 H9A 2 -0.129509 0.970401 0.406138 11.00000 -1.20000 H9B 2 0.093856 0.989857 0.391438 11.00000 -1.20000 AFIX 0 C10 1 0.052556 0.718092 0.335120 11.00000 0.03852 0.02535 = 0.04766 0.00005 -0.00324 -0.00094 AFIX 13 H10 2 -0.064486 0.667084 0.324998 11.00000 -1.20000 AFIX 0 C11 1 0.227178 0.625323 0.333709 11.00000 0.04089 0.02839 = 0.05183 -0.00257 -0.00276 0.00269 AFIX 23 H11A 2 0.221835 0.569783 0.374773 11.00000 -1.20000 H11B 2 0.215991 0.569135 0.293051 11.00000 -1.20000 AFIX 0 C12 1 0.419655 0.690898 0.331774 11.00000 0.04199 0.03732 = 0.04867 -0.00253 -0.00184 0.00626 C13 1 0.069603 0.828016 0.280182 11.00000 0.04894 0.03278 = 0.03853 -0.00100 -0.00412 0.00682 C14 1 -0.005321 0.792200 0.208589 11.00000 0.07247 0.06481 = 0.04604 -0.00604 -0.02077 0.01373 AFIX 137 H14A 2 0.018931 0.863014 0.176788 11.00000 -1.50000 H14B 2 -0.142259 0.775941 0.211092 11.00000 -1.50000 H14C 2 0.059714 0.714867 0.192355 11.00000 -1.50000 AFIX 0 C15 1 0.271354 0.881779 0.276862 11.00000 0.05148 0.03559 = 0.03707 0.00320 0.00646 -0.00032 AFIX 43 H15 2 0.287878 0.962932 0.255651 11.00000 -1.20000 AFIX 0 C16 1 0.427925 0.823280 0.301629 11.00000 0.04226 0.03901 = 0.05123 -0.00036 0.00595 -0.00576 AFIX 43 H16 2 0.546226 0.866885 0.299956 11.00000 -1.20000 AFIX 0 O1 3 -0.054467 0.930303 0.307734 11.00000 0.05551 0.03798 = 0.04472 0.00405 -0.00127 0.01617 O2 3 0.567009 0.635516 0.350688 11.00000 0.04586 0.06190 = 0.11908 0.02013 -0.01140 0.01139 S1 4 0.003494 0.339556 0.620089 11.00000 0.09375 0.04793 = 0.05112 0.00498 0.00135 -0.00929 HKLF 4 REM 180525a_a.res in P2(1)2(1)2(1) REM R1 = 0.0527 for 2079 Fo > 4sig(Fo) and 0.0640 for all 2312 data REM 173 parameters refined using 0 restraints END WGHT 0.1055 0.8090 REM Highest difference peak 0.327, deepest hole -0.442, 1-sigma level 0.070 Q1 1 0.0204 0.2991 0.5016 11.00000 0.05 0.33 Q2 1 0.0243 0.2396 0.4853 11.00000 0.05 0.29 Q3 1 0.5010 0.8620 0.3816 11.00000 0.05 0.28 Q4 1 -0.0666 0.8387 0.1656 11.00000 0.05 0.24 Q5 1 -0.0596 0.0591 0.6034 11.00000 0.05 0.19 Q6 1 -0.0707 0.7363 0.1859 11.00000 0.05 0.19 Q7 1 0.5091 0.9660 0.3617 11.00000 0.05 0.19 Q8 1 -0.0689 0.1343 0.6437 11.00000 0.05 0.19 Q9 1 -0.0337 0.5532 0.4774 11.00000 0.05 0.19 Q10 1 -0.1219 0.2233 0.4960 11.00000 0.05 0.19 Q11 1 -0.0327 0.1641 0.6706 11.00000 0.05 0.18 Q12 1 0.0605 0.7538 0.1799 11.00000 0.05 0.18 Q13 1 0.2253 0.9593 0.3820 11.00000 0.05 0.18 Q14 1 0.2425 0.2379 0.4622 11.00000 0.05 0.18 Q15 1 0.1303 0.4731 0.2625 11.00000 0.05 0.18 Q16 1 0.1859 -0.0611 0.5013 11.00000 0.05 0.18 Q17 1 -0.0696 1.0089 0.4054 11.00000 0.05 0.17 Q18 1 0.0589 0.8728 0.1673 11.00000 0.05 0.17 Q19 1 0.0669 0.2432 0.6204 11.00000 0.05 0.17 Q20 1 0.0022 0.4258 0.5188 11.00000 0.05 0.17 ; _shelx_res_checksum 44264 _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 1.543 _oxdiff_exptl_absorpt_empirical_full_min 0.737 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 C1 C 0.0317(10) 0.1792(6) 0.6066(3) 0.0560(14) Uani 1 1 d . H1 H 0.0219 0.1169 0.6418 0.067 Uiso 1 1 calc R C2 C 0.0698(10) 0.1491(6) 0.5396(3) 0.0558(14) Uani 1 1 d . H2 H 0.0932 0.0635 0.5253 0.067 Uiso 1 1 calc R C3 C 0.0722(8) 0.2588(5) 0.4904(3) 0.0445(12) Uani 1 1 d . H3 H 0.0902 0.2554 0.4423 0.053 Uiso 1 1 calc R C4 C 0.0399(7) 0.3760(5) 0.5341(3) 0.0422(11) Uani 1 1 d . C5 C 0.0308(9) 0.5068(5) 0.5097(3) 0.0496(13) Uani 1 1 d . C6 C 0.0251(9) 0.6169(5) 0.4886(3) 0.0495(13) Uani 1 1 d . C7 C 0.0069(9) 0.7507(5) 0.4674(3) 0.0474(11) Uani 1 1 d . H7 H -0.0156 0.8124 0.5022 0.057 Uiso 1 1 calc R C8 C 0.0195(7) 0.7939(4) 0.4022(3) 0.0377(10) Uani 1 1 d . C9 C -0.0181(8) 0.9356(5) 0.3814(2) 0.0456(11) Uani 1 1 d . H9A H -0.1295 0.9704 0.4061 0.055 Uiso 1 1 calc R H9B H 0.0939 0.9899 0.3914 0.055 Uiso 1 1 calc R C10 C 0.0526(7) 0.7181(4) 0.3351(3) 0.0372(10) Uani 1 1 d . H10 H -0.0645 0.6671 0.3250 0.045 Uiso 1 1 calc R C11 C 0.2272(7) 0.6253(4) 0.3337(3) 0.0404(11) Uani 1 1 d . H11A H 0.2218 0.5698 0.3748 0.048 Uiso 1 1 calc R H11B H 0.2160 0.5691 0.2931 0.048 Uiso 1 1 calc R C12 C 0.4197(7) 0.6909(5) 0.3318(3) 0.0427(11) Uani 1 1 d . C13 C 0.0696(8) 0.8280(5) 0.2802(2) 0.0401(11) Uani 1 1 d . C14 C -0.0053(11) 0.7922(6) 0.2086(3) 0.0611(15) Uani 1 1 d . H14A H 0.0189 0.8630 0.1768 0.092 Uiso 1 1 calc GR H14B H -0.1423 0.7759 0.2111 0.092 Uiso 1 1 calc GR H14C H 0.0597 0.7149 0.1924 0.092 Uiso 1 1 calc GR C15 C 0.2714(8) 0.8818(5) 0.2769(3) 0.0414(11) Uani 1 1 d . H15 H 0.2879 0.9629 0.2557 0.050 Uiso 1 1 calc R C16 C 0.4279(8) 0.8233(5) 0.3016(3) 0.0442(11) Uani 1 1 d . H16 H 0.5462 0.8669 0.3000 0.053 Uiso 1 1 calc R O1 O -0.0545(5) 0.9303(3) 0.30773(18) 0.0461(9) Uani 1 1 d . O2 O 0.5670(6) 0.6355(5) 0.3507(3) 0.0756(15) Uani 1 1 d . S1 S 0.0035(3) 0.33956(14) 0.62009(7) 0.0643(5) 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 0.069(4) 0.047(3) 0.052(3) 0.015(2) -0.005(3) -0.009(3) C2 0.067(3) 0.042(3) 0.059(3) -0.004(2) -0.007(3) 0.005(3) C3 0.046(3) 0.035(2) 0.052(3) 0.014(2) 0.013(2) 0.007(2) C4 0.042(2) 0.040(2) 0.045(2) 0.008(2) -0.002(2) -0.005(2) C5 0.051(3) 0.046(3) 0.052(3) 0.013(2) 0.002(3) -0.007(2) C6 0.056(3) 0.049(3) 0.043(2) 0.014(2) -0.001(2) -0.003(2) C7 0.057(3) 0.037(2) 0.048(3) 0.007(2) 0.007(3) 0.002(2) C8 0.036(2) 0.031(2) 0.046(2) 0.0038(18) 0.002(2) 0.0019(17) C9 0.058(3) 0.035(2) 0.043(2) 0.0031(19) 0.002(3) 0.011(2) C10 0.039(2) 0.025(2) 0.048(2) 0.0001(18) -0.003(2) -0.0009(17) C11 0.041(2) 0.028(2) 0.052(3) -0.003(2) -0.003(2) 0.0027(18) C12 0.042(2) 0.037(2) 0.049(3) -0.003(2) -0.002(2) 0.006(2) C13 0.049(3) 0.033(2) 0.039(2) -0.0010(19) -0.004(2) 0.007(2) C14 0.072(4) 0.065(3) 0.046(3) -0.006(2) -0.021(3) 0.014(3) C15 0.051(3) 0.036(2) 0.037(2) 0.003(2) 0.006(2) 0.000(2) C16 0.042(2) 0.039(2) 0.051(3) 0.000(2) 0.006(2) -0.006(2) O1 0.056(2) 0.0380(18) 0.0447(18) 0.0040(14) -0.0013(16) 0.0162(16) O2 0.046(2) 0.062(3) 0.119(4) 0.020(3) -0.011(2) 0.0114(19) S1 0.0937(12) 0.0479(8) 0.0511(8) 0.0050(6) 0.0013(8) -0.0093(8) 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' 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 C2 C1 H1 123.4 C2 C1 S1 113.3(4) S1 C1 H1 123.4 C1 C2 H2 122.0 C1 C2 C3 116.1(5) C3 C2 H2 122.0 C2 C3 H3 127.6 C2 C3 C4 104.8(4) C4 C3 H3 127.6 C3 C4 S1 113.0(3) C5 C4 C3 125.8(5) C5 C4 S1 121.1(4) C6 C5 C4 179.2(7) C5 C6 C7 175.5(6) C6 C7 H7 117.3 C8 C7 C6 125.3(5) C8 C7 H7 117.3 C7 C8 C9 123.4(5) C7 C8 C10 129.5(4) C10 C8 C9 106.9(4) C8 C9 H9A 110.8 C8 C9 H9B 110.8 H9A C9 H9B 108.9 O1 C9 C8 104.5(4) O1 C9 H9A 110.8 O1 C9 H9B 110.8 C8 C10 H10 108.4 C8 C10 C11 116.7(4) C8 C10 C13 102.5(3) C11 C10 H10 108.4 C11 C10 C13 112.2(4) C13 C10 H10 108.4 C10 C11 H11A 108.5 C10 C11 H11B 108.5 H11A C11 H11B 107.5 C12 C11 C10 115.0(4) C12 C11 H11A 108.5 C12 C11 H11B 108.5 C16 C12 C11 117.3(4) O2 C12 C11 121.9(5) O2 C12 C16 120.7(5) C14 C13 C10 114.6(4) C15 C13 C10 111.5(4) C15 C13 C14 111.6(5) O1 C13 C10 103.4(4) O1 C13 C14 107.6(4) O1 C13 C15 107.4(4) C13 C14 H14A 109.5 C13 C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15 117.3 C16 C15 C13 125.3(5) C16 C15 H15 117.3 C12 C16 H16 119.2 C15 C16 C12 121.6(5) C15 C16 H16 119.2 C9 O1 C13 106.4(3) C1 S1 C4 92.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 H1 0.9300 C1 C2 1.345(9) C1 S1 1.670(6) C2 H2 0.9300 C2 C3 1.463(8) C3 H3 0.9300 C3 C4 1.477(7) C4 C5 1.416(7) C4 S1 1.706(5) C5 C6 1.196(7) C6 C7 1.430(7) C7 H7 0.9300 C7 C8 1.328(7) C8 C9 1.523(6) C8 C10 1.516(7) C9 H9A 0.9700 C9 H9B 0.9700 C9 O1 1.433(6) C10 H10 0.9800 C10 C11 1.533(6) C10 C13 1.543(7) C11 H11A 0.9700 C11 H11B 0.9700 C11 C12 1.487(7) C12 C16 1.471(7) C12 O2 1.218(7) C13 C14 1.509(7) C13 C15 1.497(8) C13 O1 1.450(6) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 H15 0.9300 C15 C16 1.322(8) C16 H16 0.9300