#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:21:17 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288815 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247742.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_7247742 loop_ _publ_author_name 'Fan, Xin-Yang' 'Li, Jia-Cheng' 'Zhou, Ji-Jia' 'Zhou, Bo' 'Ye, Long-Wu' _publ_section_title ; Chiral Br\/onsted acid-catalyzed asymmetric dearomative spirocyclization of alkynyl thioethers ; _journal_issue 24 _journal_name_full 'Green Chemistry' _journal_page_first 10638 _journal_page_last 10643 _journal_paper_doi 10.1039/D3GC03222A _journal_volume 25 _journal_year 2023 _chemical_absolute_configuration rm _chemical_formula_moiety 'C24 H23 Br O S' _chemical_formula_sum 'C24 H23 Br O S' _chemical_formula_weight 439.39 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-07-09 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-08-18 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.82940(10) _cell_length_b 14.2435(2) _cell_length_c 20.7154(2) _cell_measurement_reflns_used 10178 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 74.4340 _cell_measurement_theta_min 3.7530 _cell_volume 2015.08(5) _computing_cell_refinement 'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4741 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _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 -83.00 -56.00 1.00 1.00 -- -40.50 125.00 -30.00 27 2 \w -108.00 -18.00 1.00 1.00 -- -40.50 -57.00 120.00 90 3 \w -64.00 30.00 1.00 1.00 -- -40.50 57.00 -90.00 94 4 \w -61.00 32.00 1.00 1.00 -- -40.50 37.00 60.00 93 5 \w 17.00 53.00 1.00 1.00 -- 43.04 -99.00 60.00 36 6 \w 99.00 178.00 1.00 1.20 -- 107.03 30.00 120.00 79 7 \w 39.00 133.00 1.00 1.20 -- 107.03 -77.00 30.00 94 8 \w 52.00 130.00 1.00 1.20 -- 107.03 -45.00 60.00 78 9 \w 111.00 177.00 1.00 1.20 -- 107.03 77.00 150.00 66 10 \w 109.00 175.00 1.00 1.20 -- 107.03 77.00-150.00 66 11 \w 62.00 110.00 1.00 1.20 -- 107.03-125.00-120.00 48 12 \w 127.00 153.00 1.00 1.20 -- 107.03 77.00-180.00 26 13 \w 68.00 107.00 1.00 1.20 -- 107.03 -94.00-150.00 39 14 \w 32.00 127.00 1.00 1.20 -- 107.03 -30.00 150.00 95 15 \w 100.00 127.00 1.00 1.20 -- 107.03 -45.00-180.00 27 16 \w 53.00 107.00 1.00 1.20 -- 107.03 -94.00 -90.00 54 17 \w 32.00 108.00 1.00 1.20 -- 107.03-102.00 0.56 76 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0242060000 _diffrn_orient_matrix_UB_12 -0.0807689000 _diffrn_orient_matrix_UB_13 0.0488649000 _diffrn_orient_matrix_UB_21 0.0337922000 _diffrn_orient_matrix_UB_22 0.0693186000 _diffrn_orient_matrix_UB_23 0.0559607000 _diffrn_orient_matrix_UB_31 -0.2217048000 _diffrn_orient_matrix_UB_32 0.0192946000 _diffrn_orient_matrix_UB_33 0.0032398000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.0302 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 14232 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.402 _diffrn_reflns_theta_min 3.766 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.821 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic light white' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.448 _exptl_crystal_description plate _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.526 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.000(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 4078 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0258 _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^)+(0.0370P)^2^+0.4300P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.0655 _reflns_Friedel_coverage 0.723 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.978 _reflns_number_gt 3892 _reflns_number_total 4078 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03222a2.cif _cod_data_source_block exp_19291_auto _cod_depositor_comments 'Adding full bibliography for 7247742.cif.' _cod_database_code 7247742 _shelxl_version_number 2013-2 _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. ; _reflns_odcompleteness_completeness 99.95 _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 2.a Ternary CH refined with riding coordinates: C2(H2), C4(H4), C9(H9) 2.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B) 2.c Aromatic/amide H refined with riding coordinates: C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C22(H22), C23(H23), C24(H24) ; _shelx_res_file ; TITL exp_19291_auto_a.res in P2(1)2(1)2(1) REM Old TITL exp_19291_auto in P212121 #19 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.166, Rweak 0.039, Alpha 0.004, Orientation as input REM Flack x = 0.174 ( 0.010 ) from Parsons' quotients REM Formula found by SHELXT: C24 O2 Br CELL 1.54184 6.8294 14.2435 20.7154 90 90 90 ZERR 4 0.0001 0.0002 0.0002 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 Br O S UNIT 96 92 4 4 4 L.S. 10 PLAN 20 TEMP -173 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.037000 0.430000 FVAR 0.53483 BR27 3 0.559824 0.850425 0.641523 11.00000 0.03645 0.02067 = 0.03048 0.00766 -0.00567 -0.01317 S26 5 0.209361 0.747777 0.746446 11.00000 0.01756 0.01915 = 0.01911 -0.00232 -0.00027 0.00421 O25 4 0.426015 0.501135 0.696690 11.00000 0.01516 0.02124 = 0.02269 0.00234 -0.00080 0.00139 C1 1 0.596183 0.709222 0.787209 11.00000 0.01873 0.03658 = 0.01564 0.00194 0.00036 -0.00151 AFIX 23 H1A 2 0.632158 0.770193 0.767569 11.00000 -1.20000 H1B 2 0.609245 0.659889 0.753821 11.00000 -1.20000 AFIX 0 C2 1 0.733071 0.687743 0.843885 11.00000 0.01440 0.05021 = 0.01965 0.00626 -0.00164 -0.00335 AFIX 13 H2 2 0.871375 0.685383 0.828115 11.00000 -1.20000 AFIX 0 C3 1 0.713283 0.764967 0.894780 11.00000 0.03715 0.03861 = 0.02580 0.00693 -0.01400 -0.01783 AFIX 23 H3A 2 0.802588 0.751830 0.931325 11.00000 -1.20000 H3B 2 0.750574 0.826189 0.875786 11.00000 -1.20000 AFIX 0 C4 1 0.502187 0.769471 0.919118 11.00000 0.04806 0.02139 = 0.01773 -0.00456 -0.00414 -0.00337 AFIX 13 H4 2 0.490315 0.820106 0.952328 11.00000 -1.20000 AFIX 0 C5 1 0.678934 0.593409 0.874073 11.00000 0.02480 0.03769 = 0.01615 0.00100 -0.00025 0.01043 AFIX 23 H5A 2 0.768453 0.579378 0.910403 11.00000 -1.20000 H5B 2 0.692222 0.542847 0.841575 11.00000 -1.20000 AFIX 0 C6 1 0.365095 0.791093 0.862243 11.00000 0.03467 0.01753 = 0.02011 -0.00480 0.00146 0.00025 AFIX 23 H6A 2 0.399868 0.852466 0.842963 11.00000 -1.20000 H6B 2 0.227961 0.794417 0.877566 11.00000 -1.20000 AFIX 0 C7 1 0.385626 0.712918 0.811328 11.00000 0.01847 0.01892 = 0.01480 -0.00263 0.00027 -0.00049 C8 1 0.329810 0.618732 0.841780 11.00000 0.02266 0.01716 = 0.01957 -0.00177 0.00182 -0.00004 AFIX 23 H8A 2 0.339931 0.568216 0.809126 11.00000 -1.20000 H8B 2 0.192742 0.621177 0.857244 11.00000 -1.20000 AFIX 0 C9 1 0.467325 0.597605 0.898493 11.00000 0.02691 0.01841 = 0.01703 0.00097 -0.00151 -0.00110 AFIX 13 H9 2 0.431200 0.535812 0.918070 11.00000 -1.20000 AFIX 0 C10 1 0.446834 0.674908 0.949265 11.00000 0.03351 0.02540 = 0.01626 0.00021 0.00116 0.00347 AFIX 23 H10A 2 0.533796 0.661409 0.986358 11.00000 -1.20000 H10B 2 0.310227 0.677211 0.965176 11.00000 -1.20000 AFIX 0 C11 1 0.296476 0.698837 0.673911 11.00000 0.01304 0.01541 = 0.01854 0.00167 -0.00216 0.00196 C12 1 0.425266 0.736409 0.632096 11.00000 0.01587 0.01716 = 0.02124 0.00503 -0.00366 -0.00078 C13 1 0.448680 0.679357 0.574594 11.00000 0.01320 0.02257 = 0.01586 0.00644 -0.00334 0.00134 C14 1 0.568398 0.690205 0.520501 11.00000 0.01553 0.03416 = 0.02062 0.00984 0.00153 0.00011 AFIX 43 H14 2 0.654067 0.742441 0.516569 11.00000 -1.20000 AFIX 0 C15 1 0.558190 0.622072 0.472560 11.00000 0.01871 0.04706 = 0.01760 0.00385 0.00393 0.00258 AFIX 43 H15 2 0.638666 0.627566 0.435346 11.00000 -1.20000 AFIX 0 C16 1 0.312189 0.535281 0.532492 11.00000 0.02209 0.02593 = 0.01904 -0.00084 -0.00131 0.00023 AFIX 43 H16 2 0.225486 0.483429 0.536360 11.00000 -1.20000 AFIX 0 C17 1 0.430932 0.545474 0.478377 11.00000 0.02476 0.03767 = 0.02057 -0.00528 0.00117 0.00411 AFIX 43 H17 2 0.425602 0.499885 0.444949 11.00000 -1.20000 AFIX 0 C18 1 0.323499 0.602493 0.580508 11.00000 0.01122 0.02048 = 0.01531 0.00377 0.00010 0.00133 C19 1 0.211053 0.609017 0.643500 11.00000 0.01279 0.01662 = 0.01384 0.00101 0.00034 0.00018 C20 1 -0.005306 0.624037 0.630281 11.00000 0.01444 0.01965 = 0.01679 0.00086 -0.00137 0.00247 AFIX 43 H20 2 -0.043661 0.672636 0.601530 11.00000 -1.20000 AFIX 0 C21 1 0.255417 0.523899 0.687109 11.00000 0.01505 0.01550 = 0.01383 -0.00253 -0.00113 0.00106 C22 1 0.091682 0.473908 0.716440 11.00000 0.01975 0.01613 = 0.01872 0.00238 -0.00074 -0.00195 AFIX 43 H22 2 0.116940 0.424064 0.745753 11.00000 -1.20000 AFIX 0 C23 1 -0.094542 0.497240 0.702657 11.00000 0.01634 0.02171 = 0.02009 0.00070 0.00258 -0.00553 AFIX 43 H23 2 -0.197863 0.463965 0.723135 11.00000 -1.20000 AFIX 0 C24 1 -0.142488 0.571459 0.657600 11.00000 0.01269 0.02376 = 0.01976 -0.00161 -0.00050 0.00133 AFIX 43 H24 2 -0.275963 0.582817 0.647315 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_19291_auto_a.res in P2(1)2(1)2(1) REM R1 = 0.0258 for 3892 Fo > 4sig(Fo) and 0.0275 for all 4078 data REM 244 parameters refined using 0 restraints END WGHT 0.0368 0.4304 REM Highest difference peak 0.526, deepest hole -0.287, 1-sigma level 0.053 Q1 1 0.0932 0.4165 0.7919 11.00000 0.05 0.53 Q2 1 0.4525 0.8584 0.6726 11.00000 0.05 0.47 Q3 1 -0.1245 0.4922 0.5606 11.00000 0.05 0.31 Q4 1 0.4358 0.8579 0.6171 11.00000 0.05 0.29 Q5 1 0.1032 0.6119 0.6379 11.00000 0.05 0.27 Q6 1 0.6870 0.8435 0.6609 11.00000 0.05 0.26 Q7 1 0.3134 0.7337 0.6432 11.00000 0.05 0.25 Q8 1 0.4407 0.7159 0.5963 11.00000 0.05 0.23 Q9 1 0.0893 0.7358 0.7569 11.00000 0.05 0.22 Q10 1 -0.0010 0.4952 0.7147 11.00000 0.05 0.22 Q11 1 0.4510 0.7078 0.6670 11.00000 0.05 0.22 Q12 1 0.4891 0.7162 0.7988 11.00000 0.05 0.21 Q13 1 -0.0506 0.5804 0.6315 11.00000 0.05 0.21 Q14 1 0.7010 0.6413 0.8616 11.00000 0.05 0.21 Q15 1 0.4600 0.7208 0.9364 11.00000 0.05 0.21 Q16 1 0.4913 0.5149 0.4185 11.00000 0.05 0.20 Q17 1 -0.0075 0.7043 0.7152 11.00000 0.05 0.19 Q18 1 0.5728 0.5979 0.8916 11.00000 0.05 0.19 Q19 1 0.2567 0.6433 0.6649 11.00000 0.05 0.19 Q20 1 0.5521 0.8550 0.5957 11.00000 0.05 0.19 ; _shelx_res_checksum 47785 _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 2.002 _oxdiff_exptl_absorpt_empirical_full_min 0.629 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br27 Br 0.55982(5) 0.85043(2) 0.64152(2) 0.02920(11) Uani 1 1 d . . . . . S26 S 0.20936(11) 0.74778(5) 0.74645(3) 0.01861(15) Uani 1 1 d . . . . . O25 O 0.4260(3) 0.50114(15) 0.69669(10) 0.0197(4) Uani 1 1 d . . . . . C1 C 0.5962(5) 0.7092(3) 0.78721(15) 0.0236(7) Uani 1 1 d . . . . . H1A H 0.6322 0.7702 0.7676 0.028 Uiso 1 1 calc R . . . . H1B H 0.6092 0.6599 0.7538 0.028 Uiso 1 1 calc R . . . . C2 C 0.7331(5) 0.6877(3) 0.84389(15) 0.0281(8) Uani 1 1 d . . . . . H2 H 0.8714 0.6854 0.8281 0.034 Uiso 1 1 calc R . . . . C3 C 0.7133(5) 0.7650(3) 0.89478(17) 0.0339(9) Uani 1 1 d . . . . . H3A H 0.8026 0.7518 0.9313 0.041 Uiso 1 1 calc R . . . . H3B H 0.7506 0.8262 0.8758 0.041 Uiso 1 1 calc R . . . . C4 C 0.5022(5) 0.7695(2) 0.91912(16) 0.0291(8) Uani 1 1 d . . . . . H4 H 0.4903 0.8201 0.9523 0.035 Uiso 1 1 calc R . . . . C5 C 0.6789(5) 0.5934(3) 0.87407(15) 0.0262(7) Uani 1 1 d . . . . . H5A H 0.7685 0.5794 0.9104 0.031 Uiso 1 1 calc R . . . . H5B H 0.6922 0.5428 0.8416 0.031 Uiso 1 1 calc R . . . . C6 C 0.3651(5) 0.7911(2) 0.86224(16) 0.0241(6) Uani 1 1 d . . . . . H6A H 0.3999 0.8525 0.8430 0.029 Uiso 1 1 calc R . . . . H6B H 0.2280 0.7944 0.8776 0.029 Uiso 1 1 calc R . . . . C7 C 0.3856(4) 0.7129(2) 0.81133(14) 0.0174(6) Uani 1 1 d . . . . . C8 C 0.3298(5) 0.6187(2) 0.84178(14) 0.0198(6) Uani 1 1 d . . . . . H8A H 0.3399 0.5682 0.8091 0.024 Uiso 1 1 calc R . . . . H8B H 0.1927 0.6212 0.8572 0.024 Uiso 1 1 calc R . . . . C9 C 0.4673(5) 0.5976(2) 0.89849(14) 0.0208(6) Uani 1 1 d . . . . . H9 H 0.4312 0.5358 0.9181 0.025 Uiso 1 1 calc R . . . . C10 C 0.4468(6) 0.6749(2) 0.94927(14) 0.0251(7) Uani 1 1 d . . . . . H10A H 0.5338 0.6614 0.9864 0.030 Uiso 1 1 calc R . . . . H10B H 0.3102 0.6772 0.9652 0.030 Uiso 1 1 calc R . . . . C11 C 0.2965(4) 0.6988(2) 0.67391(14) 0.0157(6) Uani 1 1 d . . . . . C12 C 0.4253(4) 0.73641(19) 0.63210(13) 0.0181(6) Uani 1 1 d . . . . . C13 C 0.4487(5) 0.6794(2) 0.57459(13) 0.0172(6) Uani 1 1 d . . . . . C14 C 0.5684(5) 0.6902(2) 0.52050(14) 0.0234(6) Uani 1 1 d . . . . . H14 H 0.6541 0.7424 0.5166 0.028 Uiso 1 1 calc R . . . . C15 C 0.5582(5) 0.6221(3) 0.47256(15) 0.0278(7) Uani 1 1 d . . . . . H15 H 0.6387 0.6276 0.4353 0.033 Uiso 1 1 calc R . . . . C16 C 0.3122(5) 0.5353(2) 0.53249(15) 0.0224(7) Uani 1 1 d . . . . . H16 H 0.2255 0.4834 0.5364 0.027 Uiso 1 1 calc R . . . . C17 C 0.4309(5) 0.5455(3) 0.47838(15) 0.0277(7) Uani 1 1 d . . . . . H17 H 0.4256 0.4999 0.4449 0.033 Uiso 1 1 calc R . . . . C18 C 0.3235(4) 0.6025(2) 0.58051(14) 0.0157(6) Uani 1 1 d . . . . . C19 C 0.2111(4) 0.60902(19) 0.64350(14) 0.0144(5) Uani 1 1 d . . . . . C20 C -0.0053(4) 0.6240(2) 0.63028(14) 0.0170(6) Uani 1 1 d . . . . . H20 H -0.0437 0.6726 0.6015 0.020 Uiso 1 1 calc R . . . . C21 C 0.2554(4) 0.5239(2) 0.68711(14) 0.0148(6) Uani 1 1 d . . . . . C22 C 0.0917(5) 0.4739(2) 0.71644(14) 0.0182(6) Uani 1 1 d . . . . . H22 H 0.1169 0.4241 0.7458 0.022 Uiso 1 1 calc R . . . . C23 C -0.0945(4) 0.4972(2) 0.70266(15) 0.0194(6) Uani 1 1 d . . . . . H23 H -0.1979 0.4640 0.7231 0.023 Uiso 1 1 calc R . . . . C24 C -0.1425(5) 0.5715(2) 0.65760(14) 0.0187(6) Uani 1 1 d . . . . . H24 H -0.2760 0.5828 0.6473 0.022 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 Br27 0.0365(2) 0.02067(16) 0.03048(17) 0.00766(14) -0.00567(16) -0.01317(14) S26 0.0176(3) 0.0191(3) 0.0191(3) -0.0023(3) -0.0003(3) 0.0042(3) O25 0.0152(10) 0.0212(10) 0.0227(10) 0.0023(8) -0.0008(9) 0.0014(9) C1 0.0187(17) 0.0366(17) 0.0156(14) 0.0019(13) 0.0004(12) -0.0015(14) C2 0.0144(15) 0.050(2) 0.0197(16) 0.0063(14) -0.0016(12) -0.0033(14) C3 0.037(2) 0.039(2) 0.0258(17) 0.0069(15) -0.0140(15) -0.0178(17) C4 0.048(2) 0.0214(16) 0.0177(14) -0.0046(12) -0.0041(13) -0.0034(14) C5 0.0248(18) 0.0377(19) 0.0162(15) 0.0010(13) -0.0003(12) 0.0104(14) C6 0.0347(17) 0.0175(14) 0.0201(14) -0.0048(13) 0.0015(14) 0.0003(12) C7 0.0185(15) 0.0189(14) 0.0148(13) -0.0026(11) 0.0003(11) -0.0005(11) C8 0.0227(16) 0.0172(14) 0.0196(15) -0.0018(11) 0.0018(12) 0.0000(11) C9 0.0269(18) 0.0184(14) 0.0170(14) 0.0010(11) -0.0015(13) -0.0011(13) C10 0.0335(18) 0.0254(16) 0.0163(13) 0.0002(11) 0.0012(14) 0.0035(14) C11 0.0130(14) 0.0154(14) 0.0185(14) 0.0017(11) -0.0022(11) 0.0020(11) C12 0.0159(13) 0.0172(13) 0.0212(14) 0.0050(11) -0.0037(12) -0.0008(11) C13 0.0132(14) 0.0226(14) 0.0159(13) 0.0064(11) -0.0033(12) 0.0013(12) C14 0.0155(15) 0.0342(16) 0.0206(14) 0.0098(12) 0.0015(14) 0.0001(14) C15 0.0187(15) 0.047(2) 0.0176(14) 0.0039(13) 0.0039(13) 0.0026(15) C16 0.0221(17) 0.0259(16) 0.0190(15) -0.0008(12) -0.0013(12) 0.0002(13) C17 0.0248(17) 0.0377(18) 0.0206(15) -0.0053(13) 0.0012(15) 0.0041(16) C18 0.0112(14) 0.0205(14) 0.0153(13) 0.0038(11) 0.0001(11) 0.0013(11) C19 0.0128(13) 0.0166(13) 0.0138(12) 0.0010(11) 0.0003(12) 0.0002(10) C20 0.0144(14) 0.0196(14) 0.0168(14) 0.0009(10) -0.0014(10) 0.0025(10) C21 0.0151(15) 0.0155(13) 0.0138(13) -0.0025(11) -0.0011(11) 0.0011(11) C22 0.0198(16) 0.0161(13) 0.0187(14) 0.0024(11) -0.0007(12) -0.0019(11) C23 0.0163(16) 0.0217(14) 0.0201(14) 0.0007(11) 0.0026(11) -0.0055(12) C24 0.0127(14) 0.0238(16) 0.0198(15) -0.0016(12) -0.0005(11) 0.0013(11) 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' Br Br -0.6763 1.2805 '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 C11 S26 C7 106.90(14) . . ? H1A C1 H1B 108.2 . . ? C2 C1 H1A 109.8 . . ? C2 C1 H1B 109.8 . . ? C7 C1 H1A 109.8 . . ? C7 C1 H1B 109.8 . . ? C7 C1 C2 109.4(3) . . ? C1 C2 H2 109.4 . . ? C3 C2 C1 109.3(3) . . ? C3 C2 H2 109.4 . . ? C5 C2 C1 110.0(3) . . ? C5 C2 H2 109.4 . . ? C5 C2 C3 109.2(3) . . ? C2 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C4 C3 C2 109.9(3) . . ? C4 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C3 C4 H4 109.5 . . ? C3 C4 C6 109.3(3) . . ? C3 C4 C10 109.3(3) . . ? C6 C4 H4 109.5 . . ? C10 C4 H4 109.5 . . ? C10 C4 C6 109.8(3) . . ? C2 C5 H5A 109.8 . . ? C2 C5 H5B 109.8 . . ? C2 C5 C9 109.2(3) . . ? H5A C5 H5B 108.3 . . ? C9 C5 H5A 109.8 . . ? C9 C5 H5B 109.8 . . ? C4 C6 H6A 109.9 . . ? C4 C6 H6B 109.9 . . ? C4 C6 C7 109.0(3) . . ? H6A C6 H6B 108.3 . . ? C7 C6 H6A 109.9 . . ? C7 C6 H6B 109.9 . . ? C1 C7 S26 112.4(2) . . ? C1 C7 C6 109.6(3) . . ? C1 C7 C8 109.9(3) . . ? C6 C7 S26 104.0(2) . . ? C8 C7 S26 111.6(2) . . ? C8 C7 C6 109.2(2) . . ? C7 C8 H8A 109.8 . . ? C7 C8 H8B 109.8 . . ? C7 C8 C9 109.6(3) . . ? H8A C8 H8B 108.2 . . ? C9 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? C5 C9 C8 109.4(2) . . ? C5 C9 H9 109.4 . . ? C8 C9 H9 109.4 . . ? C10 C9 C5 110.0(3) . . ? C10 C9 C8 109.2(3) . . ? C10 C9 H9 109.4 . . ? C4 C10 H10A 109.8 . . ? C4 C10 H10B 109.8 . . ? C9 C10 C4 109.3(3) . . ? C9 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C12 C11 S26 127.8(2) . . ? C12 C11 C19 108.3(3) . . ? C19 C11 S26 123.4(2) . . ? C11 C12 Br27 126.7(2) . . ? C11 C12 C13 112.2(3) . . ? C13 C12 Br27 121.1(2) . . ? C14 C13 C12 131.4(3) . . ? C18 C13 C12 107.5(3) . . ? C18 C13 C14 121.1(3) . . ? C13 C14 H14 121.1 . . ? C15 C14 C13 117.8(3) . . ? C15 C14 H14 121.1 . . ? C14 C15 H15 119.5 . . ? C14 C15 C17 120.9(3) . . ? C17 C15 H15 119.5 . . ? C17 C16 H16 120.8 . . ? C18 C16 H16 120.8 . . ? C18 C16 C17 118.4(3) . . ? C15 C17 H17 119.6 . . ? C16 C17 C15 120.8(3) . . ? C16 C17 H17 119.6 . . ? C13 C18 C19 109.7(3) . . ? C16 C18 C13 121.0(3) . . ? C16 C18 C19 129.3(3) . . ? C11 C19 C21 109.8(2) . . ? C18 C19 C11 102.2(2) . . ? C18 C19 C20 110.3(2) . . ? C18 C19 C21 110.9(2) . . ? C20 C19 C11 109.0(2) . . ? C20 C19 C21 114.1(2) . . ? C19 C20 H20 119.0 . . ? C24 C20 C19 122.1(3) . . ? C24 C20 H20 119.0 . . ? O25 C21 C19 119.3(3) . . ? O25 C21 C22 122.2(3) . . ? C22 C21 C19 118.5(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.5 . . ? C22 C23 H23 119.0 . . ? C22 C23 C24 122.1(3) . . ? C24 C23 H23 119.0 . . ? C20 C24 C23 121.8(3) . . ? C20 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? 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 Br27 C12 1.876(3) . ? S26 C7 1.871(3) . ? S26 C11 1.760(3) . ? O25 C21 1.226(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.532(4) . ? C1 C7 1.523(4) . ? C2 H2 1.0000 . ? C2 C3 1.530(5) . ? C2 C5 1.527(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.529(5) . ? C4 H4 1.0000 . ? C4 C6 1.536(5) . ? C4 C10 1.532(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C9 1.532(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.540(4) . ? C7 C8 1.531(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.534(4) . ? C9 H9 1.0000 . ? C9 C10 1.529(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.345(4) . ? C11 C19 1.541(4) . ? C12 C13 1.451(4) . ? C13 C14 1.396(4) . ? C13 C18 1.394(4) . ? C14 H14 0.9500 . ? C14 C15 1.390(5) . ? C15 H15 0.9500 . ? C15 C17 1.400(5) . ? C16 H16 0.9500 . ? C16 C17 1.391(5) . ? C16 C18 1.383(4) . ? C17 H17 0.9500 . ? C18 C19 1.517(4) . ? C19 C20 1.518(4) . ? C19 C21 1.542(4) . ? C20 H20 0.9500 . ? C20 C24 1.326(4) . ? C21 C22 1.458(4) . ? C22 H22 0.9500 . ? C22 C23 1.345(5) . ? C23 H23 0.9500 . ? C23 C24 1.448(4) . ? C24 H24 0.9500 . ?