#------------------------------------------------------------------------------ #$Date: 2015-08-31 12:02:20 +0300 (Mon, 31 Aug 2015) $ #$Revision: 153832 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/77/7117728.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_7117728 loop_ _publ_author_name 'Yin-Wei Sun' 'Xiang-Ying Tang' 'Min Shi' _publ_section_title ; A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles ; _journal_name_full Chem.Commun. _journal_page_first 13937 _journal_paper_doi 10.1039/C5cc05808B _journal_volume 51 _journal_year 2015 _chemical_formula_moiety '2(C31 H29 N2 O6 S2)' _chemical_formula_sum 'C62 H58 N4 O12 S4' _chemical_formula_weight 1179.36 _chemical_name_systematic ; ? ; _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 _atom_sites_solution_primary direct _audit_creation_date 2015-06-11 _audit_creation_method ; Olex2 1.2 (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _audit_update_record ; 2015-06-13 deposited with the CCDC. 2015-07-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.647(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 18.1593(16) _cell_length_b 10.1358(9) _cell_length_c 15.6691(13) _cell_measurement_reflns_used 3798 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.99 _cell_measurement_theta_min 2.24 _cell_volume 2882.8(4) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_unetI/netI 0.0555 _diffrn_reflns_laue_measured_fraction_full 0.999 _diffrn_reflns_laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 28610 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 30.684 _diffrn_reflns_theta_min 2.244 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6912 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0521 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.9264. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas . _exptl_crystal_description block _exptl_crystal_F_000 1236 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.469 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 373 _refine_ls_number_reflns 8867 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.986 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0529 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.1459P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1261 _refine_ls_wR_factor_ref 0.1590 _reflns_Friedel_coverage 0.000 _reflns_friedel_fraction_full . _reflns_friedel_fraction_max . _reflns_number_gt 4377 _reflns_number_total 8867 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5cc05808b2.cif _cod_data_source_block dm15482 _cod_database_code 7117728 _shelxl_version_number 2014-3 _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 0.973 _shelx_estimated_absorpt_t_min 0.955 _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 Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C13(H13A,H13B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29), C30(H30) 2.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C) ; _shelx_res_file ; TITL dm15482 in P2(1)/c CELL 0.71073 18.1593 10.1358 15.6691 90 91.647 90 ZERR 2 0.0016 0.0009 0.0013 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 124 116 8 24 8 L.S. 6 PLAN -10 0 0 SIZE 0.12 0.15 0.2 TEMP 23 BOND $H MORE -1 wpdb -1 CONF fmap 2 acta 52 OMIT 1 0 0 OMIT -2 1 10 OMIT 0 1 8 OMIT -1 1 6 OMIT 9 3 0 REM REM REM WGHT 0.071800 0.145900 FVAR 0.09972 S1 5 0.641365 -0.028494 -0.070228 11.00000 0.04613 0.04480 = 0.04756 0.00845 -0.00429 0.00011 S2 5 0.912790 -0.243037 -0.091825 11.00000 0.04077 0.07202 = 0.07227 -0.01308 -0.00492 0.00500 O1 4 0.563464 -0.019368 -0.081992 11.00000 0.04730 0.06790 = 0.07125 0.00788 -0.01588 0.00784 O2 4 0.688593 0.025132 -0.132112 11.00000 0.07638 0.05774 = 0.04944 0.01554 0.00440 -0.00529 O3 4 0.892893 -0.276525 -0.007607 11.00000 0.06087 0.07443 = 0.06691 0.00147 -0.01128 0.00411 O4 4 0.975581 -0.300863 -0.129063 11.00000 0.04705 0.09948 = 0.11234 -0.03056 0.00083 0.01515 O5 4 0.785773 -0.581843 -0.001966 11.00000 0.05818 0.10467 = 0.10692 -0.01530 -0.00289 0.00401 O6 4 0.697283 -0.493426 0.075382 11.00000 0.06977 0.06475 = 0.05515 -0.00097 -0.01567 0.00659 N1 3 0.661125 -0.186416 -0.063578 11.00000 0.03938 0.04087 = 0.04579 0.00115 0.00276 -0.00476 N2 3 0.842464 -0.282566 -0.157133 11.00000 0.04543 0.06602 = 0.06072 -0.01758 0.00073 -0.00039 C1 1 0.617571 -0.262094 -0.001993 11.00000 0.04832 0.04384 = 0.04553 0.00056 0.00494 -0.00751 AFIX 23 H1A 2 0.568871 -0.223398 0.001167 11.00000 -1.20000 H1B 2 0.641152 -0.256025 0.054206 11.00000 -1.20000 AFIX 0 C2 1 0.610373 -0.403264 -0.026507 11.00000 0.04454 0.04194 = 0.03980 0.00044 0.00354 -0.00425 C3 1 0.557255 -0.455798 -0.089974 11.00000 0.04114 0.04507 = 0.03955 0.00032 0.00497 -0.00484 C4 1 0.507138 -0.391864 -0.143442 11.00000 0.05066 0.05244 = 0.04909 0.00558 0.00224 -0.00101 AFIX 43 H4 2 0.504117 -0.300272 -0.143935 11.00000 -1.20000 AFIX 0 C5 1 0.461342 -0.467405 -0.196467 11.00000 0.05019 0.08537 = 0.04755 0.00064 -0.00238 -0.00196 AFIX 43 H5 2 0.426737 -0.426098 -0.232285 11.00000 -1.20000 AFIX 0 C6 1 0.466696 -0.602641 -0.196493 11.00000 0.05817 0.07833 = 0.05639 -0.01524 0.00296 -0.01940 AFIX 43 H6 2 0.435836 -0.651452 -0.232844 11.00000 -1.20000 AFIX 0 C7 1 0.516757 -0.667374 -0.143864 11.00000 0.06338 0.05451 = 0.05464 -0.01158 0.01412 -0.01558 AFIX 43 H7 2 0.519978 -0.758940 -0.144462 11.00000 -1.20000 AFIX 0 C8 1 0.562308 -0.593217 -0.089913 11.00000 0.04896 0.04448 = 0.04546 -0.00204 0.01199 -0.00616 C9 1 0.620561 -0.634885 -0.026099 11.00000 0.06898 0.03620 = 0.05264 0.00243 -0.00089 0.00113 AFIX 43 H9 2 0.636370 -0.719420 -0.011533 11.00000 -1.20000 AFIX 0 C10 1 0.646527 -0.505648 0.007900 11.00000 0.05149 0.05115 = 0.04316 0.00180 -0.00307 -0.00055 C11 1 0.767423 -0.537039 0.063156 11.00000 0.06263 0.05025 = 0.08545 0.00670 -0.01897 0.00122 C12 1 0.814632 -0.516832 0.140646 11.00000 0.10248 0.07631 = 0.12607 -0.00702 -0.06449 0.00791 AFIX 137 H12A 2 0.831671 -0.427188 0.142425 11.00000 -1.50000 H12B 2 0.856131 -0.575399 0.139333 11.00000 -1.50000 H12C 2 0.786711 -0.534806 0.190433 11.00000 -1.50000 AFIX 0 C13 1 0.740529 -0.217030 -0.059358 11.00000 0.04059 0.04582 = 0.04775 0.00066 -0.00153 -0.00194 AFIX 23 H13A 2 0.749580 -0.286831 -0.018025 11.00000 -1.20000 H13B 2 0.767618 -0.139567 -0.040108 11.00000 -1.20000 AFIX 0 C14 1 0.767703 -0.259056 -0.143621 11.00000 0.04202 0.04027 = 0.05210 -0.00311 -0.00006 -0.00236 C15 1 0.731588 -0.286867 -0.217797 11.00000 0.05206 0.06282 = 0.05856 -0.01243 -0.00587 -0.00246 AFIX 43 H15 2 0.680862 -0.282096 -0.227236 11.00000 -1.20000 AFIX 0 C16 1 0.783490 -0.324555 -0.279046 11.00000 0.07644 0.07122 = 0.05488 -0.01888 0.00104 -0.00459 AFIX 43 H16 2 0.772618 -0.348600 -0.335285 11.00000 -1.20000 AFIX 0 C17 1 0.850146 -0.319701 -0.242547 11.00000 0.06463 0.07078 = 0.06763 -0.02472 0.01467 -0.00200 AFIX 43 H17 2 0.894244 -0.337750 -0.268949 11.00000 -1.20000 AFIX 0 C18 1 0.666204 0.038813 0.030163 11.00000 0.04445 0.03629 = 0.04992 0.00404 0.00142 0.00438 C19 1 0.618363 0.030759 0.097239 11.00000 0.04090 0.05024 = 0.06659 -0.00115 0.00857 0.00244 AFIX 43 H19 2 0.571481 -0.004727 0.088876 11.00000 -1.20000 AFIX 0 C20 1 0.641242 0.076055 0.176451 11.00000 0.05968 0.06139 = 0.06226 -0.00803 0.01807 0.00477 AFIX 43 H20 2 0.609191 0.070667 0.221557 11.00000 -1.20000 AFIX 0 C21 1 0.710440 0.129242 0.190752 11.00000 0.06875 0.05302 = 0.05638 -0.01072 0.00625 0.00469 C22 1 0.756725 0.138719 0.122277 11.00000 0.05103 0.04783 = 0.06408 -0.00454 -0.00061 -0.00416 AFIX 43 H22 2 0.803316 0.175449 0.130540 11.00000 -1.20000 AFIX 0 C23 1 0.735151 0.094846 0.042178 11.00000 0.04477 0.04126 = 0.05649 0.00097 0.00755 -0.00264 AFIX 43 H23 2 0.766623 0.102831 -0.003323 11.00000 -1.20000 AFIX 0 C24 1 0.735265 0.173219 0.279391 11.00000 0.09997 0.10911 = 0.06512 -0.02543 0.00636 -0.00946 AFIX 137 H24A 2 0.703272 0.241839 0.298568 11.00000 -1.50000 H24B 2 0.784813 0.205972 0.277865 11.00000 -1.50000 H24C 2 0.733440 0.099715 0.317910 11.00000 -1.50000 AFIX 0 C25 1 0.919955 -0.071279 -0.098802 11.00000 0.03599 0.07378 = 0.05905 -0.00819 -0.00273 -0.00267 C26 1 0.909730 0.006898 -0.028201 11.00000 0.04462 0.07191 = 0.05868 -0.00509 0.00321 -0.00482 AFIX 43 H26 2 0.897425 -0.031085 0.023503 11.00000 -1.20000 AFIX 0 C27 1 0.917802 0.141133 -0.034585 11.00000 0.04925 0.07682 = 0.07496 -0.01062 0.00589 -0.00773 AFIX 43 H27 2 0.911692 0.192911 0.013697 11.00000 -1.20000 AFIX 0 C28 1 0.934605 0.201276 -0.110002 11.00000 0.04141 0.07687 = 0.09457 0.00489 -0.00476 -0.00939 C29 1 0.944212 0.121104 -0.180246 11.00000 0.06472 0.10843 = 0.07567 0.02020 -0.00235 -0.02038 AFIX 43 H29 2 0.955846 0.159608 -0.232019 11.00000 -1.20000 AFIX 0 C30 1 0.937129 -0.013041 -0.175912 11.00000 0.06441 0.09955 = 0.05940 -0.00874 0.00114 -0.01373 AFIX 43 H30 2 0.943750 -0.064721 -0.224130 11.00000 -1.20000 AFIX 0 C31 1 0.943540 0.348494 -0.115784 11.00000 0.07195 0.08537 = 0.13974 0.02201 0.00224 -0.01246 AFIX 137 H31A 2 0.928782 0.388405 -0.063409 11.00000 -1.50000 H31B 2 0.913337 0.381707 -0.162264 11.00000 -1.50000 H31C 2 0.994205 0.369341 -0.125369 11.00000 -1.50000 AFIX 0 HKLF 4 REM dm15482 in P2(1)/c REM R1 = 0.0529 for 4377 Fo > 4sig(Fo) and 0.1249 for all 8867 data REM 373 parameters refined using 0 restraints END WGHT 0.0715 0.1608 REM Highest difference peak 0.469, deepest hole -0.397, 1-sigma level 0.052 Q1 1 0.5973 -0.6790 0.0264 11.00000 0.05 0.47 Q2 1 0.6667 -0.6918 -0.0543 11.00000 0.05 0.42 Q3 1 0.9588 0.3547 -0.1934 11.00000 0.05 0.19 Q4 1 0.7594 -0.2520 -0.1068 11.00000 0.05 0.18 Q5 1 0.6569 0.0207 -0.0179 11.00000 0.05 0.18 Q6 1 0.7606 -0.0119 -0.1241 11.00000 0.05 0.17 Q7 1 0.6791 0.0533 -0.1511 11.00000 0.05 0.17 Q8 1 0.8471 -0.3317 -0.1936 11.00000 0.05 0.17 Q9 1 0.6514 0.0237 0.0765 11.00000 0.05 0.17 Q10 1 0.5232 -0.6395 -0.0966 11.00000 0.05 0.16 ; _shelx_res_checksum 50102 _olex2_submission_special_instructions 'No special instructions were received' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.64137(3) -0.02849(5) -0.07023(3) 0.04627(15) Uani 1 1 d . . . . . S2 S 0.91279(3) -0.24304(7) -0.09182(4) 0.06181(19) Uani 1 1 d . . . . . O1 O 0.56346(9) -0.01937(16) -0.08199(10) 0.0625(4) Uani 1 1 d . . . . . O2 O 0.68859(10) 0.02513(16) -0.13211(10) 0.0611(4) Uani 1 1 d . . . . . O3 O 0.89289(10) -0.27652(18) -0.00761(11) 0.0677(5) Uani 1 1 d . . . . . O4 O 0.97558(9) -0.3009(2) -0.12906(13) 0.0863(6) Uani 1 1 d . . . . . O5 O 0.78577(11) -0.5818(2) -0.00197(16) 0.0900(6) Uani 1 1 d . . . . . O6 O 0.69728(10) -0.49343(16) 0.07538(10) 0.0636(5) Uani 1 1 d . . . . . N1 N 0.66113(9) -0.18642(16) -0.06358(10) 0.0420(4) Uani 1 1 d . . . . . N2 N 0.84246(10) -0.2826(2) -0.15713(12) 0.0574(5) Uani 1 1 d . . . . . C1 C 0.61757(12) -0.2621(2) -0.00199(13) 0.0458(5) Uani 1 1 d . . . . . H1A H 0.5689 -0.2234 0.0012 0.055 Uiso 1 1 calc R . . . . H1B H 0.6412 -0.2560 0.0542 0.055 Uiso 1 1 calc R . . . . C2 C 0.61037(11) -0.4033(2) -0.02651(12) 0.0420(5) Uani 1 1 d . . . . . C3 C 0.55725(11) -0.4558(2) -0.08997(12) 0.0418(5) Uani 1 1 d . . . . . C4 C 0.50714(12) -0.3919(2) -0.14344(13) 0.0507(5) Uani 1 1 d . . . . . H4 H 0.5041 -0.3003 -0.1439 0.061 Uiso 1 1 calc R . . . . C5 C 0.46134(13) -0.4674(3) -0.19647(14) 0.0611(6) Uani 1 1 d . . . . . H5 H 0.4267 -0.4261 -0.2323 0.073 Uiso 1 1 calc R . . . . C6 C 0.46670(14) -0.6026(3) -0.19649(15) 0.0643(7) Uani 1 1 d . . . . . H6 H 0.4358 -0.6515 -0.2328 0.077 Uiso 1 1 calc R . . . . C7 C 0.51676(14) -0.6674(2) -0.14386(14) 0.0573(6) Uani 1 1 d . . . . . H7 H 0.5200 -0.7589 -0.1445 0.069 Uiso 1 1 calc R . . . . C8 C 0.56231(12) -0.5932(2) -0.08991(13) 0.0461(5) Uani 1 1 d . . . . . C9 C 0.62056(14) -0.6349(2) -0.02610(14) 0.0527(6) Uani 1 1 d . . . . . H9 H 0.6364 -0.7194 -0.0115 0.063 Uiso 1 1 calc R . . . . C10 C 0.64653(13) -0.5056(2) 0.00790(13) 0.0487(5) Uani 1 1 d . . . . . C11 C 0.76742(16) -0.5370(3) 0.0632(2) 0.0665(7) Uani 1 1 d . . . . . C12 C 0.8146(2) -0.5168(3) 0.1406(2) 0.1029(12) Uani 1 1 d . . . . . H12A H 0.8317 -0.4272 0.1424 0.154 Uiso 1 1 calc GR . . . . H12B H 0.8561 -0.5754 0.1393 0.154 Uiso 1 1 calc GR . . . . H12C H 0.7867 -0.5348 0.1904 0.154 Uiso 1 1 calc GR . . . . C13 C 0.74053(11) -0.2170(2) -0.05936(13) 0.0448(5) Uani 1 1 d . . . . . H13A H 0.7496 -0.2868 -0.0180 0.054 Uiso 1 1 calc R . . . . H13B H 0.7676 -0.1396 -0.0401 0.054 Uiso 1 1 calc R . . . . C14 C 0.76770(11) -0.2591(2) -0.14362(13) 0.0448(5) Uani 1 1 d . . . . . C15 C 0.73159(14) -0.2869(2) -0.21780(14) 0.0580(6) Uani 1 1 d . . . . . H15 H 0.6809 -0.2821 -0.2272 0.070 Uiso 1 1 calc R . . . . C16 C 0.78349(16) -0.3246(3) -0.27905(16) 0.0675(7) Uani 1 1 d . . . . . H16 H 0.7726 -0.3486 -0.3353 0.081 Uiso 1 1 calc R . . . . C17 C 0.85015(15) -0.3197(3) -0.24255(16) 0.0674(7) Uani 1 1 d . . . . . H17 H 0.8942 -0.3378 -0.2689 0.081 Uiso 1 1 calc R . . . . C18 C 0.66620(11) 0.03881(19) 0.03016(13) 0.0435(5) Uani 1 1 d . . . . . C19 C 0.61836(12) 0.0308(2) 0.09724(15) 0.0524(5) Uani 1 1 d . . . . . H19 H 0.5715 -0.0047 0.0889 0.063 Uiso 1 1 calc R . . . . C20 C 0.64124(14) 0.0761(2) 0.17645(16) 0.0608(6) Uani 1 1 d . . . . . H20 H 0.6092 0.0707 0.2216 0.073 Uiso 1 1 calc R . . . . C21 C 0.71044(15) 0.1292(2) 0.19075(15) 0.0593(6) Uani 1 1 d . . . . . C22 C 0.75672(13) 0.1387(2) 0.12228(15) 0.0544(6) Uani 1 1 d . . . . . H22 H 0.8033 0.1754 0.1305 0.065 Uiso 1 1 calc R . . . . C23 C 0.73515(12) 0.0948(2) 0.04218(14) 0.0474(5) Uani 1 1 d . . . . . H23 H 0.7666 0.1028 -0.0033 0.057 Uiso 1 1 calc R . . . . C24 C 0.73526(19) 0.1732(3) 0.27939(17) 0.0913(10) Uani 1 1 d . . . . . H24A H 0.7033 0.2418 0.2986 0.137 Uiso 1 1 calc GR . . . . H24B H 0.7848 0.2060 0.2779 0.137 Uiso 1 1 calc GR . . . . H24C H 0.7334 0.0997 0.3179 0.137 Uiso 1 1 calc GR . . . . C25 C 0.91996(12) -0.0713(3) -0.09880(15) 0.0564(6) Uani 1 1 d . . . . . C26 C 0.90973(13) 0.0069(3) -0.02820(16) 0.0584(6) Uani 1 1 d . . . . . H26 H 0.8974 -0.0311 0.0235 0.070 Uiso 1 1 calc R . . . . C27 C 0.91780(14) 0.1411(3) -0.03459(18) 0.0669(7) Uani 1 1 d . . . . . H27 H 0.9117 0.1929 0.0137 0.080 Uiso 1 1 calc R . . . . C28 C 0.93461(13) 0.2013(3) -0.1100(2) 0.0711(7) Uani 1 1 d . . . . . C29 C 0.94421(16) 0.1211(4) -0.1802(2) 0.0830(9) Uani 1 1 d . . . . . H29 H 0.9558 0.1596 -0.2320 0.100 Uiso 1 1 calc R . . . . C30 C 0.93713(16) -0.0130(3) -0.17591(17) 0.0745(8) Uani 1 1 d . . . . . H30 H 0.9437 -0.0647 -0.2241 0.089 Uiso 1 1 calc R . . . . C31 C 0.94354(18) 0.3485(3) -0.1158(2) 0.0990(10) Uani 1 1 d . . . . . H31A H 0.9288 0.3884 -0.0634 0.149 Uiso 1 1 calc GR . . . . H31B H 0.9133 0.3817 -0.1623 0.149 Uiso 1 1 calc GR . . . . H31C H 0.9942 0.3693 -0.1254 0.149 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 0.0461(3) 0.0448(3) 0.0476(3) 0.0085(2) -0.0043(2) 0.0001(2) S2 0.0408(3) 0.0720(4) 0.0723(4) -0.0131(3) -0.0049(3) 0.0050(3) O1 0.0473(9) 0.0679(11) 0.0712(10) 0.0079(8) -0.0159(8) 0.0078(8) O2 0.0764(12) 0.0577(10) 0.0494(9) 0.0155(8) 0.0044(8) -0.0053(8) O3 0.0609(11) 0.0744(12) 0.0669(11) 0.0015(9) -0.0113(8) 0.0041(9) O4 0.0470(10) 0.0995(15) 0.1123(15) -0.0306(12) 0.0008(10) 0.0152(10) O5 0.0582(12) 0.1047(17) 0.1069(16) -0.0153(14) -0.0029(11) 0.0040(11) O6 0.0698(12) 0.0647(11) 0.0552(10) -0.0010(8) -0.0157(8) 0.0066(8) N1 0.0394(9) 0.0409(10) 0.0458(9) 0.0012(7) 0.0028(7) -0.0048(7) N2 0.0454(11) 0.0660(13) 0.0607(12) -0.0176(10) 0.0007(9) -0.0004(9) C1 0.0483(12) 0.0438(12) 0.0455(11) 0.0006(9) 0.0049(9) -0.0075(9) C2 0.0445(11) 0.0419(12) 0.0398(10) 0.0004(9) 0.0035(9) -0.0043(9) C3 0.0411(11) 0.0451(12) 0.0396(10) 0.0003(9) 0.0050(9) -0.0048(9) C4 0.0507(13) 0.0524(14) 0.0491(12) 0.0056(10) 0.0022(10) -0.0010(10) C5 0.0502(14) 0.085(2) 0.0476(13) 0.0006(13) -0.0024(10) -0.0020(13) C6 0.0582(16) 0.078(2) 0.0564(14) -0.0152(13) 0.0030(12) -0.0194(13) C7 0.0634(15) 0.0545(15) 0.0546(13) -0.0116(11) 0.0141(12) -0.0156(12) C8 0.0490(12) 0.0445(12) 0.0455(11) -0.0020(9) 0.0120(9) -0.0062(9) C9 0.0690(15) 0.0362(12) 0.0526(13) 0.0024(10) -0.0009(11) 0.0011(10) C10 0.0515(13) 0.0512(13) 0.0432(11) 0.0018(9) -0.0031(10) -0.0005(10) C11 0.0626(17) 0.0502(15) 0.085(2) 0.0067(14) -0.0190(15) 0.0012(12) C12 0.102(3) 0.076(2) 0.126(3) -0.0070(19) -0.064(2) 0.0079(18) C13 0.0406(11) 0.0458(12) 0.0478(11) 0.0007(9) -0.0015(9) -0.0019(9) C14 0.0420(11) 0.0403(12) 0.0521(12) -0.0031(9) -0.0001(9) -0.0024(9) C15 0.0521(13) 0.0628(15) 0.0586(14) -0.0124(11) -0.0059(11) -0.0025(11) C16 0.0764(18) 0.0712(18) 0.0549(14) -0.0189(12) 0.0010(13) -0.0046(14) C17 0.0646(17) 0.0708(18) 0.0676(16) -0.0247(13) 0.0147(13) -0.0020(13) C18 0.0444(12) 0.0363(11) 0.0499(12) 0.0040(9) 0.0014(9) 0.0044(9) C19 0.0409(12) 0.0502(13) 0.0666(15) -0.0011(11) 0.0086(10) 0.0024(10) C20 0.0597(15) 0.0614(16) 0.0623(15) -0.0080(12) 0.0181(12) 0.0048(12) C21 0.0687(17) 0.0530(14) 0.0564(14) -0.0107(11) 0.0063(12) 0.0047(12) C22 0.0510(13) 0.0478(13) 0.0641(14) -0.0045(11) -0.0006(11) -0.0042(10) C23 0.0448(12) 0.0413(12) 0.0565(13) 0.0010(10) 0.0076(10) -0.0026(9) C24 0.100(2) 0.109(3) 0.0651(17) -0.0254(16) 0.0064(16) -0.0095(19) C25 0.0360(11) 0.0738(16) 0.0590(14) -0.0082(12) -0.0027(10) -0.0027(11) C26 0.0446(13) 0.0719(18) 0.0587(14) -0.0051(12) 0.0032(11) -0.0048(11) C27 0.0493(14) 0.0768(19) 0.0750(17) -0.0106(15) 0.0059(12) -0.0077(12) C28 0.0414(13) 0.0769(19) 0.095(2) 0.0049(17) -0.0048(13) -0.0094(12) C29 0.0647(18) 0.108(3) 0.0757(19) 0.0202(19) -0.0023(14) -0.0204(17) C30 0.0644(18) 0.100(2) 0.0594(16) -0.0087(15) 0.0011(13) -0.0137(15) C31 0.072(2) 0.085(2) 0.140(3) 0.022(2) 0.002(2) -0.0125(17) 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' N N 0.0061 0.0033 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 S1 N1 106.60(9) . . O1 S1 C18 108.56(10) . . O2 S1 O1 120.23(10) . . O2 S1 N1 106.32(9) . . O2 S1 C18 108.49(10) . . N1 S1 C18 105.71(9) . . O3 S2 O4 120.76(13) . . O3 S2 N2 107.64(10) . . O3 S2 C25 108.51(11) . . O4 S2 N2 105.01(11) . . O4 S2 C25 108.82(12) . . N2 S2 C25 104.99(11) . . C11 O6 C10 117.73(19) . . C1 N1 S1 115.25(13) . . C13 N1 S1 114.79(13) . . C13 N1 C1 113.71(16) . . C14 N2 S2 126.64(15) . . C14 N2 C17 108.28(19) . . C17 N2 S2 123.84(17) . . N1 C1 H1A 109.2 . . N1 C1 H1B 109.2 . . N1 C1 C2 112.04(16) . . H1A C1 H1B 107.9 . . C2 C1 H1A 109.2 . . C2 C1 H1B 109.2 . . C3 C2 C1 125.20(19) . . C10 C2 C1 127.3(2) . . C10 C2 C3 107.36(19) . . C4 C3 C2 130.6(2) . . C4 C3 C8 120.7(2) . . C8 C3 C2 108.67(18) . . C3 C4 H4 120.7 . . C3 C4 C5 118.5(2) . . C5 C4 H4 120.7 . . C4 C5 H5 119.7 . . C6 C5 C4 120.6(2) . . C6 C5 H5 119.7 . . C5 C6 H6 119.3 . . C5 C6 C7 121.4(2) . . C7 C6 H6 119.3 . . C6 C7 H7 120.7 . . C6 C7 C8 118.6(2) . . C8 C7 H7 120.7 . . C3 C8 C9 109.12(18) . . C7 C8 C3 120.2(2) . . C7 C8 C9 130.7(2) . . C8 C9 H9 129.2 . . C10 C9 C8 101.65(18) . . C10 C9 H9 129.2 . . O6 C10 C9 123.28(19) . . C2 C10 O6 123.2(2) . . C2 C10 C9 113.2(2) . . O5 C11 O6 122.4(3) . . O5 C11 C12 126.5(3) . . O6 C11 C12 111.1(3) . . C11 C12 H12A 109.5 . . C11 C12 H12B 109.5 . . C11 C12 H12C 109.5 . . H12A C12 H12B 109.5 . . H12A C12 H12C 109.5 . . H12B C12 H12C 109.5 . . N1 C13 H13A 109.3 . . N1 C13 H13B 109.3 . . N1 C13 C14 111.71(17) . . H13A C13 H13B 107.9 . . C14 C13 H13A 109.3 . . C14 C13 H13B 109.3 . . N2 C14 C13 122.11(19) . . C15 C14 N2 106.49(19) . . C15 C14 C13 131.4(2) . . C14 C15 H15 125.6 . . C14 C15 C16 108.9(2) . . C16 C15 H15 125.6 . . C15 C16 H16 125.8 . . C17 C16 C15 108.4(2) . . C17 C16 H16 125.8 . . N2 C17 H17 126.0 . . C16 C17 N2 107.9(2) . . C16 C17 H17 126.0 . . C19 C18 S1 120.31(17) . . C23 C18 S1 119.23(16) . . C23 C18 C19 120.4(2) . . C18 C19 H19 120.5 . . C20 C19 C18 119.0(2) . . C20 C19 H19 120.5 . . C19 C20 H20 119.1 . . C19 C20 C21 121.8(2) . . C21 C20 H20 119.1 . . C20 C21 C22 118.1(2) . . C20 C21 C24 120.6(2) . . C22 C21 C24 121.2(2) . . C21 C22 H22 119.3 . . C23 C22 C21 121.3(2) . . C23 C22 H22 119.3 . . C18 C23 H23 120.4 . . C22 C23 C18 119.3(2) . . C22 C23 H23 120.4 . . C21 C24 H24A 109.5 . . C21 C24 H24B 109.5 . . C21 C24 H24C 109.5 . . H24A C24 H24B 109.5 . . H24A C24 H24C 109.5 . . H24B C24 H24C 109.5 . . C26 C25 S2 120.7(2) . . C26 C25 C30 119.5(3) . . C30 C25 S2 119.8(2) . . C25 C26 H26 120.2 . . C27 C26 C25 119.6(2) . . C27 C26 H26 120.2 . . C26 C27 H27 119.0 . . C28 C27 C26 122.0(3) . . C28 C27 H27 119.0 . . C27 C28 C29 117.4(3) . . C27 C28 C31 121.3(3) . . C29 C28 C31 121.2(3) . . C28 C29 H29 119.0 . . C30 C29 C28 122.0(3) . . C30 C29 H29 119.0 . . C25 C30 H30 120.3 . . C29 C30 C25 119.3(3) . . C29 C30 H30 120.3 . . C28 C31 H31A 109.5 . . C28 C31 H31B 109.5 . . C28 C31 H31C 109.5 . . H31A C31 H31B 109.5 . . H31A C31 H31C 109.5 . . H31B C31 H31C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O1 1.4243(17) . S1 O2 1.4209(16) . S1 N1 1.6430(17) . S1 C18 1.761(2) . S2 O3 1.4193(18) . S2 O4 1.4221(17) . S2 N2 1.662(2) . S2 C25 1.749(3) . O5 C11 1.174(3) . O6 C10 1.388(3) . O6 C11 1.367(3) . N1 C1 1.480(2) . N1 C13 1.475(3) . N2 C14 1.400(3) . N2 C17 1.401(3) . C1 H1A 0.9700 . C1 H1B 0.9700 . C1 C2 1.486(3) . C2 C3 1.466(3) . C2 C10 1.334(3) . C3 C4 1.381(3) . C3 C8 1.396(3) . C4 H4 0.9300 . C4 C5 1.389(3) . C5 H5 0.9300 . C5 C6 1.374(4) . C6 H6 0.9300 . C6 C7 1.376(4) . C7 H7 0.9300 . C7 C8 1.387(3) . C8 C9 1.495(3) . C9 H9 0.9300 . C9 C10 1.486(3) . C11 C12 1.480(4) . C12 H12A 0.9600 . C12 H12B 0.9600 . C12 H12C 0.9600 . C13 H13A 0.9700 . C13 H13B 0.9700 . C13 C14 1.485(3) . C14 C15 1.348(3) . C15 H15 0.9300 . C15 C16 1.417(3) . C16 H16 0.9300 . C16 C17 1.325(4) . C17 H17 0.9300 . C18 C19 1.385(3) . C18 C23 1.383(3) . C19 H19 0.9300 . C19 C20 1.376(3) . C20 H20 0.9300 . C20 C21 1.380(3) . C21 C22 1.385(3) . C21 C24 1.515(3) . C22 H22 0.9300 . C22 C23 1.378(3) . C23 H23 0.9300 . C24 H24A 0.9600 . C24 H24B 0.9600 . C24 H24C 0.9600 . C25 C26 1.378(3) . C25 C30 1.388(3) . C26 H26 0.9300 . C26 C27 1.372(3) . C27 H27 0.9300 . C27 C28 1.372(4) . C28 C29 1.383(4) . C28 C31 1.504(4) . C29 H29 0.9300 . C29 C30 1.368(4) . C30 H30 0.9300 . C31 H31A 0.9600 . C31 H31B 0.9600 . C31 H31C 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 S1 N1 C1 C2 152.55(15) . . . . S1 N1 C13 C14 -99.93(17) . . . . S1 C18 C19 C20 175.57(18) . . . . S1 C18 C23 C22 -175.24(16) . . . . S2 N2 C14 C13 -12.1(3) . . . . S2 N2 C14 C15 170.13(18) . . . . S2 N2 C17 C16 -170.6(2) . . . . S2 C25 C26 C27 178.05(19) . . . . S2 C25 C30 C29 -178.6(2) . . . . O1 S1 N1 C1 -50.50(16) . . . . O1 S1 N1 C13 174.47(14) . . . . O1 S1 C18 C19 31.1(2) . . . . O1 S1 C18 C23 -151.57(17) . . . . O2 S1 N1 C1 -179.90(14) . . . . O2 S1 N1 C13 45.07(16) . . . . O2 S1 C18 C19 163.33(17) . . . . O2 S1 C18 C23 -19.3(2) . . . . O3 S2 N2 C14 43.5(2) . . . . O3 S2 N2 C17 -150.7(2) . . . . O3 S2 C25 C26 2.5(2) . . . . O3 S2 C25 C30 -178.39(19) . . . . O4 S2 N2 C14 173.4(2) . . . . O4 S2 N2 C17 -20.8(2) . . . . O4 S2 C25 C26 -130.6(2) . . . . O4 S2 C25 C30 48.5(2) . . . . N1 S1 C18 C19 -82.98(18) . . . . N1 S1 C18 C23 94.37(18) . . . . N1 C1 C2 C3 -81.1(2) . . . . N1 C1 C2 C10 103.6(2) . . . . N1 C13 C14 N2 174.52(18) . . . . N1 C13 C14 C15 -8.3(3) . . . . N2 S2 C25 C26 117.38(19) . . . . N2 S2 C25 C30 -63.5(2) . . . . N2 C14 C15 C16 -1.6(3) . . . . C1 N1 C13 C14 124.34(18) . . . . C1 C2 C3 C4 4.5(3) . . . . C1 C2 C3 C8 -174.53(18) . . . . C1 C2 C10 O6 1.1(3) . . . . C1 C2 C10 C9 174.22(19) . . . . C2 C3 C4 C5 -178.2(2) . . . . C2 C3 C8 C7 179.09(18) . . . . C2 C3 C8 C9 -0.7(2) . . . . C3 C2 C10 O6 -174.82(19) . . . . C3 C2 C10 C9 -1.7(2) . . . . C3 C4 C5 C6 -1.0(3) . . . . C3 C8 C9 C10 -0.2(2) . . . . C4 C3 C8 C7 0.0(3) . . . . C4 C3 C8 C9 -179.84(19) . . . . C4 C5 C6 C7 0.6(3) . . . . C5 C6 C7 C8 0.1(3) . . . . C6 C7 C8 C3 -0.4(3) . . . . C6 C7 C8 C9 179.4(2) . . . . C7 C8 C9 C10 180.0(2) . . . . C8 C3 C4 C5 0.7(3) . . . . C8 C9 C10 O6 174.33(19) . . . . C8 C9 C10 C2 1.2(2) . . . . C10 O6 C11 O5 1.1(4) . . . . C10 O6 C11 C12 179.9(2) . . . . C10 C2 C3 C4 -179.5(2) . . . . C10 C2 C3 C8 1.5(2) . . . . C11 O6 C10 C2 -121.8(2) . . . . C11 O6 C10 C9 65.8(3) . . . . C13 N1 C1 C2 -71.9(2) . . . . C13 C14 C15 C16 -179.1(2) . . . . C14 N2 C17 C16 -2.5(3) . . . . C14 C15 C16 C17 0.0(3) . . . . C15 C16 C17 N2 1.6(3) . . . . C17 N2 C14 C13 -179.7(2) . . . . C17 N2 C14 C15 2.5(3) . . . . C18 S1 N1 C1 64.91(16) . . . . C18 S1 N1 C13 -70.12(15) . . . . C18 C19 C20 C21 0.0(4) . . . . C19 C18 C23 C22 2.1(3) . . . . C19 C20 C21 C22 1.3(4) . . . . C19 C20 C21 C24 -177.5(3) . . . . C20 C21 C22 C23 -0.9(4) . . . . C21 C22 C23 C18 -0.8(3) . . . . C23 C18 C19 C20 -1.7(3) . . . . C24 C21 C22 C23 177.9(2) . . . . C25 S2 N2 C14 -72.0(2) . . . . C25 S2 N2 C17 93.9(2) . . . . C25 C26 C27 C28 1.2(4) . . . . C26 C25 C30 C29 0.5(4) . . . . C26 C27 C28 C29 -0.8(4) . . . . C26 C27 C28 C31 -179.8(2) . . . . C27 C28 C29 C30 0.3(4) . . . . C28 C29 C30 C25 -0.2(4) . . . . C30 C25 C26 C27 -1.0(4) . . . . C31 C28 C29 C30 179.2(3) . . . .