#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:30:31 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252922 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157473.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_7157473 loop_ _publ_author_name 'Lin, Qifu' 'Yao, Yongqi' 'Yang, Wen' 'Tan, Yun' 'Chen, Shuqi' 'Chen, Donghan' 'Yang, Dingqiao' _publ_section_title ; Copper-catalyzed diastereoselective hydrothioetherification of oxa(aza)benzonorbornadienes. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3575 _journal_page_last 3584 _journal_paper_doi 10.1039/d0ob00659a _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C18 H18 O3 S' _chemical_formula_sum 'C18 H18 O3 S' _chemical_formula_weight 314.38 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-12-05 _audit_creation_method ; Olex2 1.3 (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _audit_update_record ; 2019-12-05 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.085(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.54660(10) _cell_length_b 9.9811(2) _cell_length_c 27.5422(5) _cell_measurement_reflns_used 4003 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 73.4690 _cell_measurement_theta_min 3.2240 _cell_volume 1524.50(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -88.00 -30.00 0.50 0.99 -- 0.00 -19.00 150.00 116 2 \w -38.00 25.00 0.50 0.99 -- 0.00 -77.00 30.00 126 3 \w -21.00 8.00 0.50 0.99 -- 0.00 -19.00 150.00 58 4 \w 72.00 155.00 0.50 3.97 -- 95.20 15.00 0.00 166 5 \w 73.00 145.00 0.50 3.97 -- 95.20 61.00-120.00 144 6 \w 17.00 43.00 0.50 3.97 -- 95.20 -45.00 90.00 52 7 \w 65.00 96.00 0.50 3.97 -- 95.20 -45.00-150.00 62 8 \w 50.00 115.00 0.50 3.97 -- 95.20 -45.00 90.00 130 9 \w 7.00 117.00 0.50 3.97 -- 95.20 -61.00 90.00 220 10 \w 80.00 106.00 0.50 3.97 -- 95.20 45.00-120.00 52 11 \w 46.00 112.00 0.50 3.97 -- 95.20 -30.00-150.00 132 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1129952000 _diffrn_orient_matrix_UB_12 0.1222776000 _diffrn_orient_matrix_UB_13 0.0249950000 _diffrn_orient_matrix_UB_21 0.0889830000 _diffrn_orient_matrix_UB_22 -0.0528064000 _diffrn_orient_matrix_UB_23 0.0497784000 _diffrn_orient_matrix_UB_31 0.2375248000 _diffrn_orient_matrix_UB_32 0.0779542000 _diffrn_orient_matrix_UB_33 -0.0055388000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_unetI/netI 0.0475 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 6733 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.479 _diffrn_reflns_theta_max 67.479 _diffrn_reflns_theta_min 3.210 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.971 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67995 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.370 _exptl_crystal_description needle _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.270 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2749 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0404 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+0.4318P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1143 _refine_ls_wR_factor_ref 0.1178 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2469 _reflns_number_total 2749 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00659a2.cif _cod_data_source_block wang_20191205 _cod_depositor_comments 'Adding full bibliography for 7157473.cif.' _cod_database_code 7157473 _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_max 0.962 _shelx_estimated_absorpt_t_min 0.756 _reflns_odcompleteness_completeness 99.90 _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: C007(H007), C00A(H00A), C00G(H00G) 2.b Secondary CH2 refined with riding coordinates: C00F(H00D,H00F) 2.c Aromatic/amide H refined with riding coordinates: C00B(H00B), C00C(H00C), C00E(H00E), C00H(H00H), C00J(H00L), C00K(H00M), C00L(H00N) 2.d Idealised Me refined as rotating group: C00I(H00I,H00J,H00K), C00M(H00O,H00P,H00Q) ; _shelx_res_file ; wang_20191205.res created by SHELXL-2014/7 TITL wang_20191205_a.res in P2(1)/n REM Old TITL wang_20191205 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.128, Rweak 0.006, Alpha 0.021, Orientation as input REM Formula found by SHELXT: C18 O3 Cl CELL 1.54184 5.5466 9.9811 27.5422 90 91.085 90 ZERR 4 0.0001 0.0002 0.0005 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H O S UNIT 72 72 12 4 L.S. 100 PLAN 5 SIZE 0.02 0.14 0.15 CONF BOND $H list 4 MORE -1 fmap 2 acta OMIT 0 135 REM REM REM WGHT 0.066400 0.431800 FVAR 0.62601 S01 4 1.121945 0.177302 0.529020 11.00000 0.02862 0.03678 = 0.01958 0.00379 0.00225 -0.00309 O002 3 0.339425 0.379541 0.293653 11.00000 0.02955 0.03757 = 0.02118 0.00095 0.00180 0.00658 O003 3 1.053481 0.412894 0.451808 11.00000 0.02835 0.02803 = 0.02121 -0.00200 0.00463 -0.00552 O004 3 0.652755 0.200996 0.270739 11.00000 0.03338 0.04024 = 0.01867 -0.00934 0.00166 0.00638 C005 1 0.713318 0.382799 0.404700 11.00000 0.02909 0.02420 = 0.01649 0.00014 0.00656 -0.00251 C006 1 0.678494 0.252197 0.316893 11.00000 0.02821 0.02701 = 0.01663 -0.00261 0.00598 -0.00305 C007 1 0.793663 0.432399 0.454355 11.00000 0.02940 0.02797 = 0.01926 -0.00300 0.00413 -0.00064 AFIX 13 H007 2 0.743004 0.523813 0.462198 11.00000 -1.20000 AFIX 0 C008 1 0.509237 0.351795 0.328902 11.00000 0.02592 0.02673 = 0.01749 0.00343 0.00399 -0.00137 C009 1 0.874632 0.281045 0.393634 11.00000 0.02630 0.02424 = 0.01686 0.00116 0.00552 -0.00154 C00A 1 1.044728 0.274090 0.437103 11.00000 0.02583 0.02677 = 0.01915 -0.00040 0.00481 -0.00225 AFIX 13 H00A 2 1.201785 0.233267 0.430835 11.00000 -1.20000 AFIX 0 C00B 1 0.525792 0.417568 0.373509 11.00000 0.02895 0.02448 = 0.02048 0.00063 0.00859 0.00264 AFIX 43 H00B 2 0.414244 0.482680 0.381968 11.00000 -1.20000 AFIX 0 C00C 1 0.858586 0.213416 0.349697 11.00000 0.02886 0.02310 = 0.02085 -0.00108 0.00603 0.00048 AFIX 43 H00C 2 0.964771 0.144461 0.342446 11.00000 -1.20000 AFIX 0 C00D 1 0.935611 0.139787 0.578796 11.00000 0.03280 0.02978 = 0.01954 0.00171 0.00196 0.00394 C00E 1 0.726868 0.063349 0.573644 11.00000 0.03490 0.03729 = 0.02253 0.00221 0.00296 -0.00175 AFIX 43 H00E 2 0.677389 0.033110 0.543110 11.00000 -1.20000 AFIX 0 C00F 1 0.725015 0.324872 0.492061 11.00000 0.02699 0.03538 = 0.01672 -0.00081 0.00484 -0.00163 AFIX 23 H00D 2 0.559014 0.296097 0.487629 11.00000 -1.20000 H00F 2 0.749306 0.357151 0.525011 11.00000 -1.20000 AFIX 0 C00G 1 0.904311 0.210783 0.479965 11.00000 0.02976 0.02988 = 0.01665 0.00091 0.00218 -0.00470 AFIX 13 H00G 2 0.819435 0.129029 0.469832 11.00000 -1.20000 AFIX 0 C00H 1 1.007696 0.185044 0.624835 11.00000 0.04258 0.03488 = 0.02330 -0.00130 0.00001 0.00368 AFIX 43 H00H 2 1.145689 0.237266 0.628525 11.00000 -1.20000 AFIX 0 C00I 1 0.174683 0.485587 0.303474 11.00000 0.03140 0.04008 = 0.02732 0.00699 0.00519 0.00872 AFIX 137 H00I 2 0.066066 0.496869 0.276229 11.00000 -1.50000 H00J 2 0.262710 0.567176 0.308962 11.00000 -1.50000 H00K 2 0.084485 0.464030 0.331837 11.00000 -1.50000 AFIX 0 C00J 1 0.592981 0.032397 0.614047 11.00000 0.03713 0.04829 = 0.03145 0.00926 0.00999 -0.00070 AFIX 43 H00L 2 0.452908 -0.018148 0.610479 11.00000 -1.20000 AFIX 0 C00K 1 0.872160 0.151706 0.665268 11.00000 0.05744 0.04088 = 0.01938 -0.00016 0.00514 0.01230 AFIX 43 H00M 2 0.921109 0.180581 0.696008 11.00000 -1.20000 AFIX 0 C00L 1 0.665748 0.075979 0.659626 11.00000 0.04765 0.04902 = 0.02478 0.00915 0.01466 0.01014 AFIX 43 H00N 2 0.575185 0.054153 0.686577 11.00000 -1.20000 AFIX 0 C00M 1 0.854328 0.130174 0.252414 11.00000 0.03656 0.05634 = 0.02637 -0.01631 0.00420 0.00793 AFIX 137 H00O 2 0.831271 0.115423 0.218197 11.00000 -1.50000 H00P 2 0.869426 0.045511 0.268730 11.00000 -1.50000 H00Q 2 0.998244 0.181820 0.257955 11.00000 -1.50000 AFIX 0 HKLF 4 REM wang_20191205_a.res in P2(1)/n REM R1 = 0.0404 for 2469 Fo > 4sig(Fo) and 0.0441 for all 2749 data REM 201 parameters refined using 0 restraints END WGHT 0.0666 0.4293 REM Highest difference peak 0.270, deepest hole -0.395, 1-sigma level 0.058 Q1 1 0.9882 0.2349 0.4570 11.00000 0.05 0.27 Q2 1 0.7840 0.3274 0.3972 11.00000 0.05 0.26 Q3 1 0.8134 0.1340 0.5734 11.00000 0.05 0.26 Q4 1 1.2213 0.0773 0.5348 11.00000 0.05 0.25 Q5 1 0.9715 0.1848 0.5090 11.00000 0.05 0.25 ; _shelx_res_checksum 86135 _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 1.413 _oxdiff_exptl_absorpt_empirical_full_min 0.617 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 S01 S 1.12194(8) 0.17730(5) 0.52902(2) 0.02831(17) Uani 1 1 d . . . . . O002 O 0.3394(2) 0.37954(13) 0.29365(4) 0.0294(3) Uani 1 1 d . . . . . O003 O 1.0535(2) 0.41289(12) 0.45181(4) 0.0258(3) Uani 1 1 d . . . . . O004 O 0.6528(2) 0.20100(13) 0.27074(4) 0.0307(3) Uani 1 1 d . . . . . C005 C 0.7133(3) 0.38280(17) 0.40470(6) 0.0232(4) Uani 1 1 d . . . . . C006 C 0.6785(3) 0.25220(17) 0.31689(6) 0.0239(4) Uani 1 1 d . . . . . C007 C 0.7937(3) 0.43240(18) 0.45435(6) 0.0255(4) Uani 1 1 d . . . . . H007 H 0.7430 0.5238 0.4622 0.031 Uiso 1 1 calc R U . . . C008 C 0.5092(3) 0.35179(17) 0.32890(6) 0.0233(4) Uani 1 1 d . . . . . C009 C 0.8746(3) 0.28105(17) 0.39363(6) 0.0224(4) Uani 1 1 d . . . . . C00A C 1.0447(3) 0.27409(18) 0.43710(6) 0.0239(4) Uani 1 1 d . . . . . H00A H 1.2018 0.2333 0.4308 0.029 Uiso 1 1 calc R U . . . C00B C 0.5258(3) 0.41757(17) 0.37351(6) 0.0245(4) Uani 1 1 d . . . . . H00B H 0.4142 0.4827 0.3820 0.029 Uiso 1 1 calc R U . . . C00C C 0.8586(3) 0.21342(18) 0.34970(6) 0.0242(4) Uani 1 1 d . . . . . H00C H 0.9648 0.1445 0.3424 0.029 Uiso 1 1 calc R U . . . C00D C 0.9356(3) 0.13979(19) 0.57880(6) 0.0274(4) Uani 1 1 d . . . . . C00E C 0.7269(3) 0.0633(2) 0.57364(7) 0.0315(4) Uani 1 1 d . . . . . H00E H 0.6774 0.0331 0.5431 0.038 Uiso 1 1 calc R U . . . C00F C 0.7250(3) 0.32487(18) 0.49206(6) 0.0263(4) Uani 1 1 d . . . . . H00D H 0.5590 0.2961 0.4876 0.032 Uiso 1 1 calc R U . . . H00F H 0.7493 0.3572 0.5250 0.032 Uiso 1 1 calc R U . . . C00G C 0.9043(3) 0.21078(19) 0.47997(6) 0.0254(4) Uani 1 1 d . . . . . H00G H 0.8194 0.1290 0.4698 0.030 Uiso 1 1 calc R U . . . C00H C 1.0077(4) 0.1850(2) 0.62484(7) 0.0336(4) Uani 1 1 d . . . . . H00H H 1.1457 0.2373 0.6285 0.040 Uiso 1 1 calc R U . . . C00I C 0.1747(4) 0.4856(2) 0.30347(7) 0.0329(4) Uani 1 1 d . . . . . H00I H 0.0661 0.4969 0.2762 0.049 Uiso 1 1 calc R U . . . H00J H 0.2627 0.5672 0.3090 0.049 Uiso 1 1 calc R U . . . H00K H 0.0845 0.4640 0.3318 0.049 Uiso 1 1 calc R U . . . C00J C 0.5930(4) 0.0324(2) 0.61405(8) 0.0388(5) Uani 1 1 d . . . . . H00L H 0.4529 -0.0181 0.6105 0.047 Uiso 1 1 calc R U . . . C00K C 0.8722(4) 0.1517(2) 0.66527(7) 0.0392(5) Uani 1 1 d . . . . . H00M H 0.9211 0.1806 0.6960 0.047 Uiso 1 1 calc R U . . . C00L C 0.6657(4) 0.0760(2) 0.65963(7) 0.0403(5) Uani 1 1 d . . . . . H00N H 0.5752 0.0542 0.6866 0.048 Uiso 1 1 calc R U . . . C00M C 0.8543(4) 0.1302(2) 0.25241(7) 0.0397(5) Uani 1 1 d . . . . . H00O H 0.8313 0.1154 0.2182 0.060 Uiso 1 1 calc R U . . . H00P H 0.8694 0.0455 0.2687 0.060 Uiso 1 1 calc R U . . . H00Q H 0.9982 0.1818 0.2580 0.060 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 S01 0.0286(3) 0.0368(3) 0.0196(3) 0.00379(17) 0.00225(18) -0.00309(17) O002 0.0296(7) 0.0376(7) 0.0212(6) 0.0009(5) 0.0018(5) 0.0066(5) O003 0.0283(6) 0.0280(6) 0.0212(6) -0.0020(5) 0.0046(5) -0.0055(5) O004 0.0334(7) 0.0402(7) 0.0187(6) -0.0093(5) 0.0017(5) 0.0064(6) C005 0.0291(9) 0.0242(8) 0.0165(8) 0.0001(6) 0.0066(7) -0.0025(7) C006 0.0282(9) 0.0270(9) 0.0166(8) -0.0026(7) 0.0060(7) -0.0031(7) C007 0.0294(9) 0.0280(9) 0.0193(9) -0.0030(7) 0.0041(7) -0.0006(7) C008 0.0259(8) 0.0267(9) 0.0175(8) 0.0034(7) 0.0040(6) -0.0014(7) C009 0.0263(9) 0.0242(8) 0.0169(8) 0.0012(7) 0.0055(7) -0.0015(7) C00A 0.0258(8) 0.0268(9) 0.0192(8) -0.0004(7) 0.0048(7) -0.0023(7) C00B 0.0289(9) 0.0245(9) 0.0205(9) 0.0006(7) 0.0086(7) 0.0026(7) C00C 0.0289(9) 0.0231(8) 0.0208(9) -0.0011(7) 0.0060(7) 0.0005(7) C00D 0.0328(9) 0.0298(9) 0.0195(9) 0.0017(7) 0.0020(7) 0.0039(7) C00E 0.0349(10) 0.0373(10) 0.0225(9) 0.0022(8) 0.0030(7) -0.0018(8) C00F 0.0270(9) 0.0354(10) 0.0167(8) -0.0008(7) 0.0048(7) -0.0016(7) C00G 0.0298(9) 0.0299(9) 0.0167(8) 0.0009(7) 0.0022(7) -0.0047(7) C00H 0.0426(11) 0.0349(10) 0.0233(9) -0.0013(8) 0.0000(8) 0.0037(8) C00I 0.0314(10) 0.0401(11) 0.0273(10) 0.0070(8) 0.0052(8) 0.0087(8) C00J 0.0371(11) 0.0483(12) 0.0314(10) 0.0093(9) 0.0100(9) -0.0007(9) C00K 0.0574(13) 0.0409(11) 0.0194(9) -0.0002(8) 0.0051(9) 0.0123(10) C00L 0.0477(12) 0.0490(12) 0.0248(10) 0.0091(9) 0.0147(9) 0.0101(10) C00M 0.0366(11) 0.0563(13) 0.0264(10) -0.0163(9) 0.0042(8) 0.0079(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' 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 C00D S01 C00G 102.95(8) . . ? C008 O002 C00I 116.75(14) . . ? C00A O003 C007 96.53(12) . . ? C006 O004 C00M 116.35(14) . . ? C009 C005 C007 104.90(15) . . ? C00B C005 C007 133.27(16) . . ? C00B C005 C009 121.82(16) . . ? O004 C006 C008 114.88(15) . . ? O004 C006 C00C 123.95(15) . . ? C00C C006 C008 121.15(16) . . ? O003 C007 C005 100.80(13) . . ? O003 C007 H007 115.0 . . ? O003 C007 C00F 101.30(14) . . ? C005 C007 H007 115.0 . . ? C005 C007 C00F 107.93(14) . . ? C00F C007 H007 115.0 . . ? O002 C008 C006 115.37(15) . . ? O002 C008 C00B 124.25(16) . . ? C00B C008 C006 120.35(16) . . ? C005 C009 C00A 104.73(14) . . ? C00C C009 C005 121.03(16) . . ? C00C C009 C00A 134.21(16) . . ? O003 C00A C009 101.26(14) . . ? O003 C00A H00A 115.0 . . ? O003 C00A C00G 101.01(13) . . ? C009 C00A H00A 115.0 . . ? C009 C00A C00G 107.75(14) . . ? C00G C00A H00A 115.0 . . ? C005 C00B C008 117.78(16) . . ? C005 C00B H00B 121.1 . . ? C008 C00B H00B 121.1 . . ? C006 C00C H00C 121.1 . . ? C009 C00C C006 117.73(16) . . ? C009 C00C H00C 121.1 . . ? C00E C00D S01 122.22(14) . . ? C00E C00D C00H 119.54(18) . . ? C00H C00D S01 118.20(15) . . ? C00D C00E H00E 120.1 . . ? C00J C00E C00D 119.89(19) . . ? C00J C00E H00E 120.1 . . ? C007 C00F H00D 111.5 . . ? C007 C00F H00F 111.5 . . ? C007 C00F C00G 101.43(13) . . ? H00D C00F H00F 109.3 . . ? C00G C00F H00D 111.5 . . ? C00G C00F H00F 111.5 . . ? S01 C00G H00G 111.5 . . ? C00A C00G S01 107.55(12) . . ? C00A C00G H00G 111.5 . . ? C00F C00G S01 113.13(12) . . ? C00F C00G C00A 101.32(14) . . ? C00F C00G H00G 111.5 . . ? C00D C00H H00H 120.1 . . ? C00K C00H C00D 119.9(2) . . ? C00K C00H H00H 120.1 . . ? O002 C00I H00I 109.5 . . ? O002 C00I H00J 109.5 . . ? O002 C00I H00K 109.5 . . ? H00I C00I H00J 109.5 . . ? H00I C00I H00K 109.5 . . ? H00J C00I H00K 109.5 . . ? C00E C00J H00L 119.7 . . ? C00L C00J C00E 120.5(2) . . ? C00L C00J H00L 119.7 . . ? C00H C00K H00M 120.0 . . ? C00L C00K C00H 120.0(2) . . ? C00L C00K H00M 120.0 . . ? C00J C00L H00N 119.9 . . ? C00K C00L C00J 120.19(18) . . ? C00K C00L H00N 119.9 . . ? O004 C00M H00O 109.5 . . ? O004 C00M H00P 109.5 . . ? O004 C00M H00Q 109.5 . . ? H00O C00M H00P 109.5 . . ? H00O C00M H00Q 109.5 . . ? H00P C00M H00Q 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 S01 C00D 1.7724(18) . ? S01 C00G 1.8255(18) . ? O002 C008 1.368(2) . ? O002 C00I 1.428(2) . ? O003 C007 1.457(2) . ? O003 C00A 1.444(2) . ? O004 C006 1.375(2) . ? O004 C00M 1.423(2) . ? C005 C007 1.514(2) . ? C005 C009 1.391(2) . ? C005 C00B 1.381(3) . ? C006 C008 1.411(2) . ? C006 C00C 1.389(3) . ? C007 H007 0.9800 . ? C007 C00F 1.546(2) . ? C008 C00B 1.394(2) . ? C009 C00A 1.512(2) . ? C009 C00C 1.387(2) . ? C00A H00A 0.9800 . ? C00A C00G 1.560(2) . ? C00B H00B 0.9300 . ? C00C H00C 0.9300 . ? C00D C00E 1.392(3) . ? C00D C00H 1.397(3) . ? C00E H00E 0.9300 . ? C00E C00J 1.384(3) . ? C00F H00D 0.9700 . ? C00F H00F 0.9700 . ? C00F C00G 1.552(3) . ? C00G H00G 0.9800 . ? C00H H00H 0.9300 . ? C00H C00K 1.396(3) . ? C00I H00I 0.9600 . ? C00I H00J 0.9600 . ? C00I H00K 0.9600 . ? C00J H00L 0.9300 . ? C00J C00L 1.382(3) . ? C00K H00M 0.9300 . ? C00K C00L 1.378(3) . ? C00L H00N 0.9300 . ? C00M H00O 0.9600 . ? C00M H00P 0.9600 . ? C00M H00Q 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 S01 C00D C00E C00J 177.38(16) . . . . ? S01 C00D C00H C00K -176.76(15) . . . . ? O002 C008 C00B C005 -177.23(15) . . . . ? O003 C007 C00F C00G -35.20(16) . . . . ? O003 C00A C00G S01 -83.39(14) . . . . ? O003 C00A C00G C00F 35.53(16) . . . . ? O004 C006 C008 O002 2.2(2) . . . . ? O004 C006 C008 C00B -175.91(15) . . . . ? O004 C006 C00C C009 174.98(16) . . . . ? C005 C007 C00F C00G 70.19(17) . . . . ? C005 C009 C00A O003 -33.25(16) . . . . ? C005 C009 C00A C00G 72.30(17) . . . . ? C005 C009 C00C C006 1.0(3) . . . . ? C006 C008 C00B C005 0.7(2) . . . . ? C007 O003 C00A C009 52.51(13) . . . . ? C007 O003 C00A C00G -58.31(14) . . . . ? C007 C005 C009 C00A -0.03(17) . . . . ? C007 C005 C009 C00C -178.68(15) . . . . ? C007 C005 C00B C008 178.25(17) . . . . ? C007 C00F C00G S01 114.83(13) . . . . ? C007 C00F C00G C00A 0.00(17) . . . . ? C008 C006 C00C C009 -3.5(2) . . . . ? C009 C005 C007 O003 32.90(16) . . . . ? C009 C005 C007 C00F -72.85(17) . . . . ? C009 C005 C00B C008 -3.2(2) . . . . ? C009 C00A C00G S01 170.88(12) . . . . ? C009 C00A C00G C00F -70.20(17) . . . . ? C00A O003 C007 C005 -52.34(14) . . . . ? C00A O003 C007 C00F 58.62(14) . . . . ? C00A C009 C00C C006 -177.20(17) . . . . ? C00B C005 C007 O003 -148.41(18) . . . . ? C00B C005 C007 C00F 105.8(2) . . . . ? C00B C005 C009 C00A -178.91(15) . . . . ? C00B C005 C009 C00C 2.4(3) . . . . ? C00C C006 C008 O002 -179.20(15) . . . . ? C00C C006 C008 C00B 2.7(3) . . . . ? C00C C009 C00A O003 145.13(19) . . . . ? C00C C009 C00A C00G -109.3(2) . . . . ? C00D S01 C00G C00A 168.32(12) . . . . ? C00D S01 C00G C00F 57.28(14) . . . . ? C00D C00E C00J C00L -0.5(3) . . . . ? C00D C00H C00K C00L -1.0(3) . . . . ? C00E C00D C00H C00K 0.9(3) . . . . ? C00E C00J C00L C00K 0.4(3) . . . . ? C00G S01 C00D C00E 39.98(18) . . . . ? C00G S01 C00D C00H -142.39(15) . . . . ? C00H C00D C00E C00J -0.2(3) . . . . ? C00H C00K C00L C00J 0.3(3) . . . . ? C00I O002 C008 C006 -176.24(15) . . . . ? C00I O002 C008 C00B 1.8(2) . . . . ? C00M O004 C006 C008 162.89(17) . . . . ? C00M O004 C006 C00C -15.7(2) . . . . ?