#------------------------------------------------------------------------------ #$Date: 2021-11-05 00:57:11 +0200 (Fri, 05 Nov 2021) $ #$Revision: 270305 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/92/7129200.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_7129200 loop_ _publ_author_name 'Ji, Kai' 'Lu, Ka' 'Huang, Jie' 'Li, Zi-Hao' 'Ding, Tong-Mei' 'Chen, Zhi-Min' _publ_section_title ; Br\/onsted Acid-Catalyzed Solvent-Controlled Regioselective Hydrothiolation and Diastereoselective Cascade Cyclization of Dienes ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC05383C _journal_year 2021 _chemical_formula_moiety 'C18 H20 S' _chemical_formula_sum 'C18 H20 S' _chemical_formula_weight 268.40 _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 direct _audit_creation_date 2021-05-07 _audit_creation_method ; Olex2 1.3-ac4 (compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739) ; _audit_update_record ; 2021-08-10 deposited with the CCDC. 2021-11-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.856(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 29.0653(6) _cell_length_b 5.67134(10) _cell_length_c 19.4203(4) _cell_measurement_reflns_used 5070 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 74.3310 _cell_measurement_theta_min 3.2460 _cell_volume 3029.43(11) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.947 _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 27.00 0.50 0.05 -- -48.70 19.00 30.00 100 2 \w -55.00 24.00 0.50 0.05 -- -48.70 82.00 -71.00 158 3 \w -59.00 -29.00 0.50 0.10 -- -101.00 61.00 -60.00 60 4 \w -75.00 -45.00 0.50 0.10 -- -101.00 82.00 -71.00 60 5 \w -120.00 -88.00 0.50 0.10 -- -101.00 -45.00-150.00 64 6 \w -118.00 -74.00 0.50 0.05 -- -48.70-125.00-120.00 88 7 \w -120.00 -95.00 0.50 0.05 -- -48.70-125.00 -60.00 50 8 \w -120.00 -84.00 0.50 0.05 -- -48.70-125.00 -90.00 72 9 \w -160.00 -97.00 0.50 0.10 -- -101.00 -45.00-120.00 126 10 \w -173.00 -97.00 0.50 0.10 -- -101.00 -61.00-150.00 152 11 \w -22.00 71.00 0.50 0.05 -- 48.70 -82.00 166.00 186 12 \w 44.00 123.00 0.50 0.10 -- 103.25 -82.00 166.00 158 13 \w 139.00 177.00 0.50 0.10 -- 103.25 15.00 30.00 76 14 \w 129.00 178.00 0.50 0.10 -- 103.25 30.00 60.00 98 15 \w 89.00 167.00 0.50 0.10 -- 103.25 82.00 -71.00 156 16 \w 93.00 124.00 0.50 0.10 -- 103.25 15.00 30.00 62 17 \w 91.00 116.00 0.50 0.10 -- 103.25 30.00 60.00 50 18 \w 69.00 96.00 0.50 0.10 -- 103.25 -94.00 -30.00 54 19 \w 32.00 57.00 0.50 0.10 -- 103.25 -61.00 -30.00 50 20 \w -159.00-129.00 0.50 0.10 -- -101.00 -82.00 166.00 60 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0362910000 _diffrn_orient_matrix_UB_12 0.1590057000 _diffrn_orient_matrix_UB_13 0.0562466000 _diffrn_orient_matrix_UB_21 -0.0001946000 _diffrn_orient_matrix_UB_22 0.1744451000 _diffrn_orient_matrix_UB_23 -0.0608670000 _diffrn_orient_matrix_UB_31 -0.0426718000 _diffrn_orient_matrix_UB_32 0.1344341000 _diffrn_orient_matrix_UB_33 0.0125383000 _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 0.0184 _diffrn_reflns_av_unetI/netI 0.0182 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.947 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 9077 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.947 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.958 _diffrn_reflns_theta_min 3.213 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'PhotonJet R (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.743 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.177 _exptl_crystal_description block _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.201 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 2955 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0392 _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^)+(0.0635P)^2^+1.0192P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1119 _refine_ls_wR_factor_ref 0.1176 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2515 _reflns_number_total 2955 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc05383c2.cif _cod_data_source_block chenzmjkw-175p _cod_database_code 7129200 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H S' _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 0.966 _shelx_estimated_absorpt_t_min 0.845 _diffrn_oxdiff_digest_frames ; 018f45d191cb2cab0e03bc33a8992db7de018800f5f ; _diffrn_oxdiff_digest_hkl ; 014a4b4800d76f1294e5841d9c3504e893b81d ; _reflns_odcompleteness_completeness 100.00 _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: C1(H1), C3(H3) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.c Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14) 2.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL ChenZMJKW-175P in C2/c #15 chenzmjkw-175p.res created by SHELXL-2018/3 at 15:11:29 on 07-May-2021 REM reset to C2/c #15 CELL 1.54184 29.065275 5.67134 19.420325 90 108.8557 90 ZERR 8 0.000615 0.000102 0.000406 0 0.0022 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H S UNIT 144 160 8 L.S. 20 PLAN 4 SIZE 0.1 0.05 0.02 TEMP 20(2) MORE -1 BOND $H CONF fmap 2 acta REM REM REM WGHT 0.063500 1.019200 FVAR 3.20760 S1 3 0.120466 0.558862 0.210855 11.00000 0.05854 0.06831 = 0.05597 0.00661 0.00570 -0.00051 C1 1 0.077877 0.316489 0.192121 11.00000 0.05359 0.08425 = 0.04891 -0.00987 0.01418 -0.00781 AFIX 13 H1 2 0.091119 0.183725 0.172229 11.00000 -1.20000 AFIX 0 C2 1 0.070493 0.242886 0.262428 11.00000 0.05065 0.09864 = 0.05485 -0.00237 0.01598 -0.00868 AFIX 23 H2A 2 0.044341 0.128262 0.251298 11.00000 -1.20000 H2B 2 0.059986 0.379699 0.283366 11.00000 -1.20000 AFIX 0 C3 1 0.115022 0.136471 0.320066 11.00000 0.05560 0.05405 = 0.05178 -0.00791 0.02135 -0.00391 AFIX 13 H3 2 0.117444 -0.027785 0.305947 11.00000 -1.20000 AFIX 0 C4 1 0.163660 0.253027 0.327335 11.00000 0.05000 0.05299 = 0.04432 -0.00688 0.01869 0.00182 C5 1 0.168685 0.440359 0.283445 11.00000 0.04873 0.05741 = 0.04355 -0.00450 0.01554 0.00072 C6 1 0.102785 0.130575 0.390691 11.00000 0.05036 0.04987 = 0.05243 0.00284 0.01864 0.00357 C7 1 0.114491 0.314627 0.439898 11.00000 0.05904 0.05595 = 0.05356 -0.00013 0.02218 0.00079 AFIX 43 H7 2 0.131717 0.443203 0.431254 11.00000 -1.20000 AFIX 0 C8 1 0.100816 0.309879 0.502211 11.00000 0.06965 0.07863 = 0.05136 -0.00156 0.02223 0.01166 AFIX 43 H8 2 0.109314 0.434073 0.535183 11.00000 -1.20000 AFIX 0 C9 1 0.074832 0.122751 0.515300 11.00000 0.07267 0.09473 = 0.06083 0.02065 0.03340 0.01756 AFIX 43 H9 2 0.065509 0.120349 0.556817 11.00000 -1.20000 AFIX 0 C10 1 0.062748 -0.060247 0.466795 11.00000 0.07476 0.07488 = 0.08520 0.02384 0.03829 0.00067 AFIX 43 H10 2 0.045184 -0.187455 0.475457 11.00000 -1.20000 AFIX 0 C11 1 0.076572 -0.056922 0.404763 11.00000 0.06801 0.05605 = 0.07605 0.00267 0.02918 -0.00406 AFIX 43 H11 2 0.068131 -0.182222 0.372195 11.00000 -1.20000 AFIX 0 C12 1 0.213743 0.545311 0.293284 11.00000 0.05531 0.06991 = 0.05132 0.00249 0.01848 -0.00560 AFIX 43 H12 2 0.215921 0.670186 0.263453 11.00000 -1.20000 AFIX 0 C13 1 0.255078 0.467872 0.346256 11.00000 0.04816 0.08086 = 0.05522 -0.00451 0.01794 -0.00237 C14 1 0.250712 0.274342 0.386941 11.00000 0.04995 0.07550 = 0.05393 0.00031 0.01461 0.00999 AFIX 43 H14 2 0.278564 0.214548 0.421204 11.00000 -1.20000 AFIX 0 C15 1 0.206431 0.165330 0.378790 11.00000 0.05493 0.05807 = 0.04886 -0.00134 0.01903 0.00766 C16 1 0.030953 0.400720 0.135886 11.00000 0.05864 0.14161 = 0.05678 0.00993 0.00473 -0.01174 AFIX 137 H16A 2 0.017687 0.529040 0.155668 11.00000 -1.50000 H16B 2 0.007965 0.273422 0.123501 11.00000 -1.50000 H16C 2 0.037620 0.452806 0.093035 11.00000 -1.50000 AFIX 0 C17 1 0.206353 -0.047426 0.425496 11.00000 0.07347 0.06657 = 0.06574 0.01063 0.02298 0.01629 AFIX 137 H17A 2 0.194141 -0.003336 0.464071 11.00000 -1.50000 H17B 2 0.238902 -0.106456 0.445843 11.00000 -1.50000 H17C 2 0.185966 -0.167754 0.396267 11.00000 -1.50000 AFIX 0 C18 1 0.303465 0.586601 0.358246 11.00000 0.05169 0.11623 = 0.08468 0.00480 0.01876 -0.01198 AFIX 137 H18A 2 0.300528 0.700013 0.320364 11.00000 -1.50000 H18B 2 0.327314 0.470444 0.357454 11.00000 -1.50000 H18C 2 0.313358 0.664933 0.404552 11.00000 -1.50000 AFIX 0 HKLF 4 REM ChenZMJKW-175P in C2/c #15 REM wR2 = 0.1176, GooF = S = 1.071, Restrained GooF = 1.071 for all data REM R1 = 0.0392 for 2515 Fo > 4sig(Fo) and 0.0451 for all 2955 data REM 175 parameters refined using 0 restraints END WGHT 0.0635 1.0191 REM Highest difference peak 0.201, deepest hole -0.267, 1-sigma level 0.035 Q1 1 0.1033 0.5681 0.2422 11.00000 0.05 0.20 Q2 1 0.2989 0.7773 0.3569 11.00000 0.05 0.19 Q3 1 0.3148 0.5517 0.3114 11.00000 0.05 0.18 Q4 1 0.3322 0.5352 0.4060 11.00000 0.05 0.18 ; _shelx_res_checksum 40366 _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 1.607 _oxdiff_exptl_absorpt_empirical_full_min 0.833 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 0.12047(2) 0.55886(8) 0.21085(2) 0.06402(17) Uani 1 1 d . . . . . C1 C 0.07788(6) 0.3165(3) 0.19212(8) 0.0628(4) Uani 1 1 d . . . . . H1 H 0.091119 0.183725 0.172229 0.075 Uiso 1 1 calc R . . . . C2 C 0.07049(6) 0.2429(4) 0.26243(9) 0.0683(5) Uani 1 1 d . . . . . H2A H 0.044341 0.128262 0.251298 0.082 Uiso 1 1 calc R . . . . H2B H 0.059986 0.379699 0.283366 0.082 Uiso 1 1 calc R . . . . C3 C 0.11502(6) 0.1365(3) 0.32007(8) 0.0528(4) Uani 1 1 d . . . . . H3 H 0.117444 -0.027785 0.305947 0.063 Uiso 1 1 calc R . . . . C4 C 0.16366(5) 0.2530(3) 0.32734(7) 0.0483(3) Uani 1 1 d . . . . . C5 C 0.16868(5) 0.4404(3) 0.28345(8) 0.0497(3) Uani 1 1 d . . . . . C6 C 0.10278(5) 0.1306(3) 0.39069(8) 0.0504(3) Uani 1 1 d . . . . . C7 C 0.11449(6) 0.3146(3) 0.43990(8) 0.0552(4) Uani 1 1 d . . . . . H7 H 0.131717 0.443203 0.431254 0.066 Uiso 1 1 calc R . . . . C8 C 0.10082(7) 0.3099(3) 0.50221(9) 0.0659(5) Uani 1 1 d . . . . . H8 H 0.109314 0.434073 0.535183 0.079 Uiso 1 1 calc R . . . . C9 C 0.07483(7) 0.1228(4) 0.51530(10) 0.0732(5) Uani 1 1 d . . . . . H9 H 0.065509 0.120349 0.556817 0.088 Uiso 1 1 calc R . . . . C10 C 0.06275(7) -0.0602(4) 0.46679(12) 0.0753(5) Uani 1 1 d . . . . . H10 H 0.045184 -0.187455 0.475457 0.090 Uiso 1 1 calc R . . . . C11 C 0.07657(7) -0.0569(3) 0.40476(11) 0.0653(4) Uani 1 1 d . . . . . H11 H 0.068131 -0.182222 0.372195 0.078 Uiso 1 1 calc R . . . . C12 C 0.21374(6) 0.5453(3) 0.29328(9) 0.0585(4) Uani 1 1 d . . . . . H12 H 0.215921 0.670186 0.263453 0.070 Uiso 1 1 calc R . . . . C13 C 0.25508(6) 0.4679(3) 0.34626(9) 0.0611(4) Uani 1 1 d . . . . . C14 C 0.25071(6) 0.2743(3) 0.38694(9) 0.0603(4) Uani 1 1 d . . . . . H14 H 0.278564 0.214548 0.421204 0.072 Uiso 1 1 calc R . . . . C15 C 0.20643(5) 0.1653(3) 0.37879(8) 0.0534(4) Uani 1 1 d . . . . . C16 C 0.03095(7) 0.4007(5) 0.13589(10) 0.0890(7) Uani 1 1 d . . . . . H16A H 0.017687 0.529040 0.155668 0.134 Uiso 1 1 calc GR . . . . H16B H 0.007965 0.273422 0.123501 0.134 Uiso 1 1 calc GR . . . . H16C H 0.037620 0.452806 0.093035 0.134 Uiso 1 1 calc GR . . . . C17 C 0.20635(7) -0.0474(3) 0.42550(10) 0.0685(5) Uani 1 1 d . . . . . H17A H 0.194141 -0.003336 0.464071 0.103 Uiso 1 1 calc GR . . . . H17B H 0.238902 -0.106456 0.445843 0.103 Uiso 1 1 calc GR . . . . H17C H 0.185966 -0.167754 0.396267 0.103 Uiso 1 1 calc GR . . . . C18 C 0.30347(7) 0.5866(4) 0.35825(13) 0.0850(6) Uani 1 1 d . . . . . H18A H 0.300528 0.700013 0.320364 0.127 Uiso 1 1 calc GR . . . . H18B H 0.327314 0.470444 0.357454 0.127 Uiso 1 1 calc GR . . . . H18C H 0.313358 0.664933 0.404552 0.127 Uiso 1 1 calc GR . . . . 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 0.0585(3) 0.0683(3) 0.0560(3) 0.00661(18) 0.00570(18) -0.00051(18) C1 0.0536(9) 0.0843(12) 0.0489(8) -0.0099(8) 0.0142(7) -0.0078(8) C2 0.0507(9) 0.0986(13) 0.0549(9) -0.0024(9) 0.0160(7) -0.0087(9) C3 0.0556(8) 0.0540(8) 0.0518(8) -0.0079(7) 0.0213(7) -0.0039(7) C4 0.0500(8) 0.0530(8) 0.0443(7) -0.0069(6) 0.0187(6) 0.0018(6) C5 0.0487(8) 0.0574(9) 0.0436(7) -0.0045(6) 0.0155(6) 0.0007(6) C6 0.0504(8) 0.0499(8) 0.0524(8) 0.0028(6) 0.0186(6) 0.0036(6) C7 0.0590(9) 0.0560(9) 0.0536(8) -0.0001(7) 0.0222(7) 0.0008(7) C8 0.0697(10) 0.0786(12) 0.0514(8) -0.0016(8) 0.0222(8) 0.0117(9) C9 0.0727(11) 0.0947(14) 0.0608(10) 0.0206(10) 0.0334(9) 0.0176(10) C10 0.0748(12) 0.0749(12) 0.0852(13) 0.0238(10) 0.0383(10) 0.0007(9) C11 0.0680(10) 0.0561(10) 0.0760(11) 0.0027(8) 0.0292(9) -0.0041(8) C12 0.0553(9) 0.0699(10) 0.0513(8) 0.0025(7) 0.0185(7) -0.0056(8) C13 0.0482(8) 0.0809(11) 0.0552(9) -0.0045(8) 0.0179(7) -0.0024(8) C14 0.0500(8) 0.0755(11) 0.0539(8) 0.0003(8) 0.0146(7) 0.0100(8) C15 0.0549(8) 0.0581(9) 0.0489(8) -0.0013(7) 0.0190(6) 0.0077(7) C16 0.0586(10) 0.142(2) 0.0568(10) 0.0099(12) 0.0047(8) -0.0117(12) C17 0.0735(11) 0.0666(11) 0.0657(10) 0.0106(8) 0.0230(9) 0.0163(9) C18 0.0517(10) 0.1162(18) 0.0847(13) 0.0048(12) 0.0188(9) -0.0120(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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 C5 S1 C1 100.74(8) . . ? S1 C1 H1 109.5 . . ? C2 C1 S1 108.49(12) . . ? C2 C1 H1 109.5 . . ? C2 C1 C16 112.31(15) . . ? C16 C1 S1 107.60(15) . . ? C16 C1 H1 109.5 . . ? C1 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C1 C2 C3 115.85(14) . . ? H2A C2 H2B 107.4 . . ? C3 C2 H2A 108.3 . . ? C3 C2 H2B 108.3 . . ? C2 C3 H3 106.8 . . ? C4 C3 C2 115.78(14) . . ? C4 C3 H3 106.8 . . ? C6 C3 C2 106.13(12) . . ? C6 C3 H3 106.8 . . ? C6 C3 C4 113.89(12) . . ? C5 C4 C3 123.29(13) . . ? C5 C4 C15 117.25(14) . . ? C15 C4 C3 119.42(14) . . ? C4 C5 S1 124.23(11) . . ? C12 C5 S1 114.48(12) . . ? C12 C5 C4 121.27(14) . . ? C7 C6 C3 121.93(14) . . ? C7 C6 C11 118.14(15) . . ? C11 C6 C3 119.82(15) . . ? C6 C7 H7 119.6 . . ? C6 C7 C8 120.77(16) . . ? C8 C7 H7 119.6 . . ? C7 C8 H8 119.8 . . ? C9 C8 C7 120.33(17) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 120.2 . . ? C10 C9 C8 119.52(16) . . ? C10 C9 H9 120.2 . . ? C9 C10 H10 119.8 . . ? C9 C10 C11 120.34(17) . . ? C11 C10 H10 119.8 . . ? C6 C11 C10 120.90(17) . . ? C6 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C5 C12 H12 119.3 . . ? C13 C12 C5 121.36(16) . . ? C13 C12 H12 119.3 . . ? C12 C13 C14 117.47(15) . . ? C12 C13 C18 121.20(18) . . ? C14 C13 C18 121.32(17) . . ? C13 C14 H14 118.6 . . ? C13 C14 C15 122.74(15) . . ? C15 C14 H14 118.6 . . ? C4 C15 C17 122.37(15) . . ? C14 C15 C4 119.71(15) . . ? C14 C15 C17 117.91(15) . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 1.8064(18) . ? S1 C5 1.7681(15) . ? C1 H1 0.9800 . ? C1 C2 1.508(2) . ? C1 C16 1.523(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.535(2) . ? C3 H3 0.9800 . ? C3 C4 1.525(2) . ? C3 C6 1.525(2) . ? C4 C5 1.399(2) . ? C4 C15 1.410(2) . ? C5 C12 1.394(2) . ? C6 C7 1.381(2) . ? C6 C11 1.386(2) . ? C7 H7 0.9300 . ? C7 C8 1.391(2) . ? C8 H8 0.9300 . ? C8 C9 1.373(3) . ? C9 H9 0.9300 . ? C9 C10 1.369(3) . ? C10 H10 0.9300 . ? C10 C11 1.388(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C12 C13 1.377(2) . ? C13 C14 1.382(3) . ? C13 C18 1.508(2) . ? C14 H14 0.9300 . ? C14 C15 1.390(2) . ? C15 C17 1.510(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C1 C2 C3 -66.0(2) . . . . ? S1 C5 C12 C13 -178.11(13) . . . . ? C1 S1 C5 C4 -20.73(14) . . . . ? C1 S1 C5 C12 157.71(12) . . . . ? C1 C2 C3 C4 39.6(2) . . . . ? C1 C2 C3 C6 167.01(16) . . . . ? C2 C3 C4 C5 -2.0(2) . . . . ? C2 C3 C4 C15 -179.70(14) . . . . ? C2 C3 C6 C7 -91.52(18) . . . . ? C2 C3 C6 C11 84.47(19) . . . . ? C3 C4 C5 S1 -3.3(2) . . . . ? C3 C4 C5 C12 178.37(14) . . . . ? C3 C4 C15 C14 -178.42(13) . . . . ? C3 C4 C15 C17 2.5(2) . . . . ? C3 C6 C7 C8 176.84(14) . . . . ? C3 C6 C11 C10 -176.53(16) . . . . ? C4 C3 C6 C7 37.0(2) . . . . ? C4 C3 C6 C11 -146.97(15) . . . . ? C4 C5 C12 C13 0.4(2) . . . . ? C5 S1 C1 C2 51.65(14) . . . . ? C5 S1 C1 C16 173.39(13) . . . . ? C5 C4 C15 C14 3.7(2) . . . . ? C5 C4 C15 C17 -175.40(14) . . . . ? C5 C12 C13 C14 3.2(3) . . . . ? C5 C12 C13 C18 -178.11(17) . . . . ? C6 C3 C4 C5 -125.44(15) . . . . ? C6 C3 C4 C15 56.84(19) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C7 C6 C11 C10 -0.4(3) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C6 0.0(3) . . . . ? C11 C6 C7 C8 0.8(2) . . . . ? C12 C13 C14 C15 -3.3(3) . . . . ? C13 C14 C15 C4 -0.2(2) . . . . ? C13 C14 C15 C17 179.00(16) . . . . ? C15 C4 C5 S1 174.49(11) . . . . ? C15 C4 C5 C12 -3.9(2) . . . . ? C16 C1 C2 C3 175.21(17) . . . . ? C18 C13 C14 C15 177.98(17) . . . . ?