#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:42:55 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270509 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158307.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_7158307 loop_ _publ_author_name 'Zeng, Wenlei' 'Yu, Aimin' 'Meng, Xiangtai' _publ_section_title ; Catalyst-controlled switchable [4 + 1], [4 + 3] and [3 + 2] domino reactions of azadienes and MBH carbonates: diverse synthesis of benzothiophene fused derivatives. ; _journal_issue 40 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8783 _journal_page_last 8788 _journal_paper_doi 10.1039/d1ob01702k _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C36 H29 Cl N2 O5 S2' _chemical_formula_sum 'C36 H29 Cl N2 O5 S2' _chemical_formula_weight 669.18 _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 2019-06-05 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-06-27 deposited with the CCDC. 2021-09-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.484(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.4201(12) _cell_length_b 11.3961(14) _cell_length_c 33.642(3) _cell_measurement_reflns_used 3351 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.4180 _cell_measurement_theta_min 2.7330 _cell_volume 3213.4(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)' _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_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _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 -72.00 -40.00 1.00 70.00 -- 30.00 54.00 -60.00 32 2 \w 1.00 27.00 1.00 70.00 -- 30.00 54.00 -60.00 26 3 \w -57.00 118.00 1.00 70.00 -- 30.00 54.00 60.00 175 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0316327000 _diffrn_orient_matrix_UB_12 -0.0277700000 _diffrn_orient_matrix_UB_13 -0.0164230000 _diffrn_orient_matrix_UB_21 0.0141175000 _diffrn_orient_matrix_UB_22 0.0557300000 _diffrn_orient_matrix_UB_23 -0.0082976000 _diffrn_orient_matrix_UB_31 0.0772342000 _diffrn_orient_matrix_UB_32 0.0010062000 _diffrn_orient_matrix_UB_33 0.0104577000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1894 _diffrn_reflns_av_unetI/netI 0.2852 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 10958 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.009 _diffrn_reflns_theta_max 25.009 _diffrn_reflns_theta_min 3.176 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.22713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.383 _exptl_crystal_description block _exptl_crystal_F_000 1392 _refine_diff_density_max 0.236 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.800 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 418 _refine_ls_number_reflns 5579 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.800 _refine_ls_R_factor_all 0.2175 _refine_ls_R_factor_gt 0.0829 _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^)] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1200 _refine_ls_wR_factor_ref 0.1726 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1840 _reflns_number_total 5579 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01702k2.cif _cod_data_source_block 13 _cod_depositor_comments 'Adding full bibliography for 7158307--7158313.cif.' _cod_database_code 7158307 _shelx_shelxl_version_number 2017/1 _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 99.54 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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: C00C(H00C), C00H(H00H) 2.b Secondary CH2 refined with riding coordinates: C00Z(H00A,H00B) 2.c Aromatic/amide H refined with riding coordinates: C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010), C012(H012), C013(H013), C014(H014), C015(H015), C017(H017), C019(H019) 2.d Idealised Me refined as rotating group: C016(H01A,H01B,H01C), C018(H01D,H01E,H01F), C01A(H01G,H01H,H01I) ; _shelx_res_file ; TITL 13_a.res in P2(1)/n 13.res created by SHELXL-2017/1 at 13:21:01 on 05-Jun-2019 REM Old TITL 13 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.278, Rweak 0.134, Alpha 0.093, Orientation as input REM Formula found by SHELXT: C36 N2 O5 S Cl2 CELL 0.71073 8.4201 11.3961 33.6422 90 95.484 90 ZERR 4 0.0012 0.0014 0.0034 0 0.01 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O S UNIT 144 116 4 8 20 8 L.S. 20 0 0 PLAN 20 BOND $H list 4 fmap 2 53 acta OMIT -3 50.02 OMIT 0 1 3 OMIT 1 0 1 OMIT -1 1 1 OMIT -1 0 3 OMIT 0 1 4 OMIT 1 1 0 OMIT -1 1 2 OMIT 1 1 1 OMIT -2 5 13 OMIT -5 1 30 OMIT -3 1 25 OMIT 1 1 2 OMIT -7 3 21 OMIT -6 1 31 OMIT -8 4 22 OMIT -8 7 4 OMIT -6 1 33 OMIT -4 3 32 OMIT -4 4 32 OMIT -6 1 32 OMIT -4 4 31 OMIT -5 6 12 OMIT -4 4 33 OMIT -5 1 33 OMIT 3 10 18 OMIT -5 4 34 OMIT -8 7 7 OMIT -4 3 33 OMIT -7 6 11 OMIT -8 7 8 OMIT -6 0 32 OMIT -8 7 5 OMIT -5 5 12 OMIT -3 3 27 OMIT -6 1 34 OMIT -5 4 19 OMIT -8 6 11 OMIT -5 1 29 OMIT -7 8 2 OMIT -4 4 35 OMIT -8 7 6 OMIT -2 0 22 OMIT -5 4 33 OMIT -7 3 5 OMIT -1 9 16 OMIT -3 4 32 OMIT -3 3 26 OMIT -7 5 22 OMIT -7 5 21 OMIT -8 7 10 OMIT -5 0 29 OMIT -1 0 13 OMIT -7 7 11 OMIT 2 0 4 OMIT 2 1 4 OMIT 0 0 6 OMIT 1 3 1 OMIT -3 6 13 OMIT -1 2 4 REM REM REM WGHT 0.000000 FVAR 0.36544 S01 6 0.454170 0.253816 0.335885 11.00000 0.04944 0.04870 = 0.04086 0.00624 0.00106 -0.00544 S002 6 0.990189 0.435344 0.305591 11.00000 0.05021 0.05207 = 0.04743 -0.00419 0.00369 -0.00799 CL03 3 0.865907 -0.193427 0.533220 11.00000 0.10732 0.05575 = 0.06894 0.02284 -0.01090 0.01481 O004 5 0.923334 0.105873 0.377112 11.00000 0.06966 0.03831 = 0.05195 -0.00585 0.01242 0.00753 O005 5 0.415401 0.200967 0.297676 11.00000 0.06361 0.05966 = 0.04668 -0.01407 -0.00630 -0.00835 O006 5 0.745089 -0.015813 0.400034 11.00000 0.12006 0.02788 = 0.06248 -0.00255 0.03140 -0.01255 O007 5 0.397292 0.204143 0.370803 11.00000 0.06552 0.07064 = 0.04487 0.02023 0.00752 -0.01368 O008 5 0.560994 0.390366 0.452239 11.00000 0.11965 0.03502 = 0.05633 0.00412 0.00407 0.02982 N009 4 0.652822 0.246899 0.344585 11.00000 0.04261 0.03692 = 0.02432 -0.00260 0.00146 -0.00179 N00A 4 0.557564 0.262373 0.504426 11.00000 0.07159 0.04715 = 0.03448 -0.00390 0.00771 0.01146 C00B 1 0.747795 0.303045 0.317189 11.00000 0.03892 0.02799 = 0.03422 -0.00326 0.00325 0.01104 C00C 1 0.874477 0.361408 0.380712 11.00000 0.04679 0.02812 = 0.02745 0.00425 -0.00215 0.00905 AFIX 13 H00C 2 0.964647 0.310928 0.390045 11.00000 -1.20000 AFIX 0 C00D 1 0.757934 0.299853 0.274542 11.00000 0.05387 0.03560 = 0.02927 -0.00301 -0.00337 0.00255 C00E 1 0.597587 0.296989 0.468246 11.00000 0.05104 0.04409 = 0.04379 -0.00067 -0.00048 0.00243 C00F 1 0.867517 0.370126 0.336520 11.00000 0.04594 0.03205 = 0.03666 -0.00067 0.00383 0.00155 C00G 1 0.894252 0.478239 0.402324 11.00000 0.05746 0.02181 = 0.03522 -0.00890 0.00421 -0.00154 C00H 1 0.715138 0.292603 0.385684 11.00000 0.04310 0.02703 = 0.03079 -0.00289 0.00748 0.00691 AFIX 13 H00H 2 0.636888 0.347716 0.394765 11.00000 -1.20000 AFIX 0 C00I 1 0.704608 0.107572 0.484529 11.00000 0.04165 0.03550 = 0.03279 0.00407 0.00435 0.00452 C00J 1 0.688711 0.193393 0.452014 11.00000 0.04728 0.03845 = 0.03341 0.00336 0.00201 -0.00184 C00K 1 0.623445 0.150771 0.515112 11.00000 0.04470 0.04349 = 0.02660 -0.00490 0.00181 -0.01055 C00L 1 0.882166 0.372974 0.264337 11.00000 0.05349 0.04469 = 0.04193 -0.00007 -0.00609 -0.00006 C00M 1 0.770282 -0.056874 0.525782 11.00000 0.05288 0.04804 = 0.04147 0.01661 -0.00209 -0.00149 C00N 1 0.799464 0.080820 0.397297 11.00000 0.06529 0.03853 = 0.03437 -0.00315 -0.00517 0.01066 C00O 1 0.732927 0.190895 0.414635 11.00000 0.05218 0.03169 = 0.03458 -0.00369 0.00094 -0.00081 C00P 1 0.782730 0.001764 0.490372 11.00000 0.05348 0.04321 = 0.03471 0.01835 -0.00162 -0.00722 AFIX 43 H00P 2 0.842217 -0.029216 0.470952 11.00000 -1.20000 AFIX 0 C00Q 1 0.809494 0.577331 0.389181 11.00000 0.06999 0.03663 = 0.04865 0.00909 0.01017 0.01274 AFIX 43 H00Q 2 0.728473 0.571014 0.368477 11.00000 -1.20000 AFIX 0 C00R 1 0.915306 0.390222 0.224862 11.00000 0.06037 0.06254 = 0.04387 0.00220 0.01241 0.00260 AFIX 43 H00R 2 0.993327 0.443112 0.218644 11.00000 -1.20000 AFIX 0 C00S 1 0.401719 0.406228 0.333636 11.00000 0.03629 0.06013 = 0.03398 0.00537 0.00397 0.00058 C00T 1 1.011699 0.490896 0.434316 11.00000 0.09245 0.04416 = 0.04889 -0.01056 -0.01779 -0.00757 AFIX 43 H00T 2 1.070287 0.425820 0.443790 11.00000 -1.20000 AFIX 0 C00U 1 0.671737 0.234773 0.243518 11.00000 0.06170 0.05787 = 0.04291 -0.00759 -0.00585 -0.00261 AFIX 43 H00U 2 0.591461 0.183010 0.249131 11.00000 -1.20000 AFIX 0 C00V 1 0.682372 -0.015769 0.554635 11.00000 0.06017 0.06502 = 0.03590 0.01679 -0.00018 -0.01007 AFIX 43 H00V 2 0.672166 -0.060317 0.577412 11.00000 -1.20000 AFIX 0 C00W 1 0.412800 0.464919 0.298347 11.00000 0.04190 0.06697 = 0.06287 0.01201 0.02002 0.00984 AFIX 43 H00W 2 0.449174 0.427898 0.276308 11.00000 -1.20000 AFIX 0 C00X 1 0.844163 0.685855 0.406566 11.00000 0.12162 0.03469 = 0.06138 0.00302 0.01556 0.01014 AFIX 43 H00X 2 0.787351 0.751754 0.397111 11.00000 -1.20000 AFIX 0 C00Y 1 0.709488 0.250016 0.205386 11.00000 0.07185 0.07299 = 0.03512 -0.01067 0.00205 0.00815 AFIX 43 H00Y 2 0.653024 0.207455 0.185103 11.00000 -1.20000 AFIX 0 C00Z 1 0.994909 0.013185 0.354882 11.00000 0.08864 0.05518 = 0.06199 -0.01530 0.00462 0.01640 AFIX 23 H00A 2 1.093238 -0.013017 0.369580 11.00000 -1.20000 H00B 2 0.922701 -0.053194 0.351704 11.00000 -1.20000 AFIX 0 C010 1 0.347234 0.457630 0.366326 11.00000 0.04177 0.07972 = 0.05148 0.00277 -0.00445 0.01031 AFIX 43 H010 2 0.340202 0.415595 0.389788 11.00000 -1.20000 AFIX 0 C011 1 0.311677 0.638356 0.328966 11.00000 0.05039 0.04382 = 0.08431 -0.01118 0.01667 -0.00156 C012 1 0.828637 0.326302 0.195277 11.00000 0.07958 0.08461 = 0.03086 -0.00281 0.01006 0.00326 AFIX 43 H012 2 0.849781 0.334202 0.168778 11.00000 -1.20000 AFIX 0 C013 1 0.607383 0.093309 0.550091 11.00000 0.07710 0.06860 = 0.03828 -0.00072 0.00246 0.01100 AFIX 43 H013 2 0.549802 0.124989 0.569767 11.00000 -1.20000 AFIX 0 C014 1 0.960935 0.696878 0.437437 11.00000 0.11351 0.04569 = 0.06760 -0.02016 0.02790 -0.02330 AFIX 43 H014 2 0.985281 0.770332 0.448425 11.00000 -1.20000 AFIX 0 C015 1 1.041920 0.599957 0.452158 11.00000 0.11116 0.06047 = 0.06897 -0.01613 -0.02307 -0.01569 AFIX 43 H015 2 1.117305 0.606782 0.474113 11.00000 -1.20000 AFIX 0 C016 1 0.466555 0.335308 0.528574 11.00000 0.09301 0.07388 = 0.05620 0.00013 0.01860 0.01354 AFIX 137 H01A 2 0.450840 0.410870 0.516207 11.00000 -1.50000 H01B 2 0.523051 0.344421 0.554555 11.00000 -1.50000 H01C 2 0.364859 0.299451 0.531122 11.00000 -1.50000 AFIX 0 C017 1 0.366696 0.583366 0.297071 11.00000 0.06317 0.05902 = 0.07823 0.02391 0.01905 0.00455 AFIX 43 H017 2 0.373979 0.625648 0.273670 11.00000 -1.20000 AFIX 0 C018 1 1.027254 0.055191 0.316805 11.00000 0.14584 0.05798 = 0.09879 -0.01059 0.04104 0.01615 AFIX 137 H01D 2 0.928560 0.069485 0.300797 11.00000 -1.50000 H01E 2 1.088051 -0.002346 0.303942 11.00000 -1.50000 H01F 2 1.087049 0.126872 0.319898 11.00000 -1.50000 AFIX 0 C019 1 0.302520 0.575075 0.363400 11.00000 0.05068 0.07780 = 0.07746 -0.00838 -0.01225 0.01535 AFIX 43 H019 2 0.265359 0.611771 0.385402 11.00000 -1.20000 AFIX 0 C01A 1 0.253237 0.765458 0.325896 11.00000 0.06535 0.05564 = 0.18425 0.01308 0.02742 0.01876 AFIX 137 H01G 2 0.326967 0.815057 0.341608 11.00000 -1.50000 H01H 2 0.149990 0.770842 0.335645 11.00000 -1.50000 H01I 2 0.246088 0.790221 0.298508 11.00000 -1.50000 AFIX 0 HKLF 4 REM 13_a.res in P2(1)/n REM R1 = 0.0829 for 1840 Fo > 4sig(Fo) and 0.2175 for all 5579 data REM 418 parameters refined using 0 restraints END WGHT 0.0000 0.0000 REM Highest difference peak 0.236, deepest hole -0.306, 1-sigma level 0.060 Q1 1 0.8346 -0.0054 0.4973 11.00000 0.05 0.24 Q2 1 0.6696 0.4322 0.3579 11.00000 0.05 0.23 Q3 1 0.1694 0.3149 0.3385 11.00000 0.05 0.21 Q4 1 0.8812 -0.3043 0.5037 11.00000 0.05 0.21 Q5 1 0.2952 0.2453 0.3201 11.00000 0.05 0.20 Q6 1 1.0309 0.5228 0.2800 11.00000 0.05 0.20 Q7 1 0.5949 0.4245 0.5180 11.00000 0.05 0.20 Q8 1 0.3157 0.7915 0.2409 11.00000 0.05 0.20 Q9 1 0.6710 0.0637 0.2216 11.00000 0.05 0.19 Q10 1 0.5953 0.0782 0.6155 11.00000 0.05 0.19 Q11 1 0.7167 -0.2825 0.5442 11.00000 0.05 0.19 Q12 1 0.3322 0.6130 0.2417 11.00000 0.05 0.18 Q13 1 0.6593 -0.1021 0.5969 11.00000 0.05 0.18 Q14 1 0.8169 -0.1054 0.5614 11.00000 0.05 0.18 Q15 1 0.9368 0.5484 0.3208 11.00000 0.05 0.18 Q16 1 0.9876 0.5779 0.2232 11.00000 0.05 0.18 Q17 1 0.9515 0.5327 0.3824 11.00000 0.05 0.18 Q18 1 1.0819 0.5489 0.2001 11.00000 0.05 0.18 Q19 1 0.4602 0.1329 0.3200 11.00000 0.05 0.18 Q20 1 0.2138 0.2805 0.2886 11.00000 0.05 0.18 ; _shelx_res_checksum 47021 _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 2.836 _oxdiff_exptl_absorpt_empirical_full_min 0.427 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 0.4542(2) 0.25382(16) 0.33589(5) 0.0465(5) Uani 1 1 d . . . . . S002 S 0.9902(2) 0.43534(16) 0.30559(5) 0.0500(5) Uani 1 1 d . . . . . Cl03 Cl 0.8659(3) -0.19343(17) 0.53322(6) 0.0786(7) Uani 1 1 d . . . . . O004 O 0.9233(6) 0.1059(4) 0.37711(14) 0.0529(14) Uani 1 1 d . . . . . O005 O 0.4154(6) 0.2010(4) 0.29768(12) 0.0574(14) Uani 1 1 d . . . . . O006 O 0.7451(7) -0.0158(4) 0.40003(15) 0.0687(17) Uani 1 1 d . . . . . O007 O 0.3973(6) 0.2041(4) 0.37080(13) 0.0602(15) Uani 1 1 d . . . . . O008 O 0.5610(7) 0.3904(4) 0.45224(14) 0.0706(17) Uani 1 1 d . . . . . N009 N 0.6528(6) 0.2469(4) 0.34458(13) 0.0347(13) Uani 1 1 d . . . . . N00A N 0.5576(7) 0.2624(5) 0.50443(16) 0.0509(16) Uani 1 1 d . . . . . C00B C 0.7478(8) 0.3030(5) 0.31719(17) 0.0337(16) Uani 1 1 d . . . . . C00C C 0.8745(8) 0.3614(5) 0.38071(16) 0.0345(16) Uani 1 1 d . . . . . H00C H 0.964647 0.310928 0.390045 0.041 Uiso 1 1 calc R . . . . C00D C 0.7579(8) 0.2999(5) 0.27454(18) 0.0401(18) Uani 1 1 d . . . . . C00E C 0.5976(9) 0.2970(6) 0.4682(2) 0.0466(19) Uani 1 1 d . . . . . C00F C 0.8675(8) 0.3701(5) 0.33652(18) 0.0382(17) Uani 1 1 d . . . . . C00G C 0.8943(8) 0.4782(5) 0.40232(18) 0.0382(17) Uani 1 1 d . . . . . C00H C 0.7151(7) 0.2926(5) 0.38568(16) 0.0334(16) Uani 1 1 d . . . . . H00H H 0.636888 0.347716 0.394765 0.040 Uiso 1 1 calc R . . . . C00I C 0.7046(8) 0.1076(5) 0.48453(18) 0.0366(17) Uani 1 1 d . . . . . C00J C 0.6887(8) 0.1934(6) 0.45201(18) 0.0398(17) Uani 1 1 d . . . . . C00K C 0.6234(8) 0.1508(6) 0.51511(18) 0.0384(17) Uani 1 1 d . . . . . C00L C 0.8822(9) 0.3730(6) 0.26434(19) 0.0474(19) Uani 1 1 d . . . . . C00M C 0.7703(9) -0.0569(6) 0.5258(2) 0.0479(19) Uani 1 1 d . . . . . C00N C 0.7995(10) 0.0808(6) 0.3973(2) 0.0467(19) Uani 1 1 d . . . . . C00O C 0.7329(8) 0.1909(5) 0.41464(18) 0.0397(18) Uani 1 1 d . . . . . C00P C 0.7827(8) 0.0018(6) 0.49037(18) 0.0442(19) Uani 1 1 d . . . . . H00P H 0.842217 -0.029216 0.470952 0.053 Uiso 1 1 calc R . . . . C00Q C 0.8095(9) 0.5773(6) 0.3892(2) 0.051(2) Uani 1 1 d . . . . . H00Q H 0.728473 0.571014 0.368477 0.062 Uiso 1 1 calc R . . . . C00R C 0.9153(9) 0.3902(6) 0.2249(2) 0.055(2) Uani 1 1 d . . . . . H00R H 0.993327 0.443112 0.218644 0.066 Uiso 1 1 calc R . . . . C00S C 0.4017(8) 0.4062(6) 0.33364(19) 0.0434(18) Uani 1 1 d . . . . . C00T C 1.0117(9) 0.4909(6) 0.43432(19) 0.063(2) Uani 1 1 d . . . . . H00T H 1.070287 0.425820 0.443790 0.076 Uiso 1 1 calc R . . . . C00U C 0.6717(9) 0.2348(6) 0.24352(19) 0.055(2) Uani 1 1 d . . . . . H00U H 0.591461 0.183010 0.249131 0.066 Uiso 1 1 calc R . . . . C00V C 0.6824(9) -0.0158(7) 0.5546(2) 0.054(2) Uani 1 1 d . . . . . H00V H 0.672166 -0.060317 0.577412 0.065 Uiso 1 1 calc R . . . . C00W C 0.4128(8) 0.4649(6) 0.2983(2) 0.056(2) Uani 1 1 d . . . . . H00W H 0.449174 0.427898 0.276308 0.068 Uiso 1 1 calc R . . . . C00X C 0.8442(11) 0.6859(6) 0.4066(2) 0.072(3) Uani 1 1 d . . . . . H00X H 0.787351 0.751754 0.397111 0.087 Uiso 1 1 calc R . . . . C00Y C 0.7095(10) 0.2500(7) 0.2054(2) 0.060(2) Uani 1 1 d . . . . . H00Y H 0.653024 0.207455 0.185103 0.072 Uiso 1 1 calc R . . . . C00Z C 0.9949(10) 0.0132(7) 0.3549(2) 0.069(3) Uani 1 1 d . . . . . H00A H 1.093238 -0.013017 0.369580 0.083 Uiso 1 1 calc R . . . . H00B H 0.922701 -0.053194 0.351704 0.083 Uiso 1 1 calc R . . . . C010 C 0.3472(8) 0.4576(7) 0.3663(2) 0.058(2) Uani 1 1 d . . . . . H010 H 0.340202 0.415595 0.389788 0.070 Uiso 1 1 calc R . . . . C011 C 0.3117(9) 0.6384(7) 0.3290(3) 0.059(2) Uani 1 1 d . . . . . C012 C 0.8286(10) 0.3263(7) 0.1953(2) 0.065(2) Uani 1 1 d . . . . . H012 H 0.849781 0.334202 0.168778 0.078 Uiso 1 1 calc R . . . . C013 C 0.6074(9) 0.0933(7) 0.5501(2) 0.062(2) Uani 1 1 d . . . . . H013 H 0.549802 0.124989 0.569767 0.074 Uiso 1 1 calc R . . . . C014 C 0.9609(12) 0.6969(7) 0.4374(2) 0.074(3) Uani 1 1 d . . . . . H014 H 0.985281 0.770332 0.448425 0.089 Uiso 1 1 calc R . . . . C015 C 1.0419(11) 0.6000(7) 0.4522(2) 0.082(3) Uani 1 1 d . . . . . H015 H 1.117305 0.606782 0.474113 0.099 Uiso 1 1 calc R . . . . C016 C 0.4666(10) 0.3353(7) 0.5286(2) 0.074(3) Uani 1 1 d . . . . . H01A H 0.450840 0.410870 0.516207 0.110 Uiso 1 1 calc GR . . . . H01B H 0.523051 0.344421 0.554555 0.110 Uiso 1 1 calc GR . . . . H01C H 0.364859 0.299451 0.531122 0.110 Uiso 1 1 calc GR . . . . C017 C 0.3667(9) 0.5834(7) 0.2971(3) 0.066(2) Uani 1 1 d . . . . . H017 H 0.373979 0.625648 0.273670 0.079 Uiso 1 1 calc R . . . . C018 C 1.0273(12) 0.0552(7) 0.3168(3) 0.099(3) Uani 1 1 d . . . . . H01D H 0.928560 0.069485 0.300797 0.148 Uiso 1 1 calc GR . . . . H01E H 1.088051 -0.002346 0.303942 0.148 Uiso 1 1 calc GR . . . . H01F H 1.087049 0.126872 0.319898 0.148 Uiso 1 1 calc GR . . . . C019 C 0.3025(9) 0.5751(8) 0.3634(3) 0.070(3) Uani 1 1 d . . . . . H019 H 0.265359 0.611771 0.385402 0.084 Uiso 1 1 calc R . . . . C01A C 0.2532(9) 0.7655(6) 0.3259(3) 0.101(3) Uani 1 1 d . . . . . H01G H 0.326967 0.815057 0.341608 0.151 Uiso 1 1 calc GR . . . . H01H H 0.149990 0.770842 0.335645 0.151 Uiso 1 1 calc GR . . . . H01I H 0.246088 0.790221 0.298508 0.151 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 S01 0.0494(12) 0.0487(11) 0.0409(10) 0.0062(10) 0.0011(9) -0.0054(10) S002 0.0502(13) 0.0521(11) 0.0474(10) -0.0042(10) 0.0037(9) -0.0080(10) Cl03 0.107(2) 0.0558(12) 0.0689(13) 0.0228(12) -0.0109(13) 0.0148(13) O004 0.070(4) 0.038(3) 0.052(3) -0.006(3) 0.012(3) 0.008(3) O005 0.064(4) 0.060(3) 0.047(3) -0.014(3) -0.006(3) -0.008(3) O006 0.120(5) 0.028(3) 0.062(3) -0.003(3) 0.031(3) -0.013(3) O007 0.066(4) 0.071(3) 0.045(3) 0.020(3) 0.008(3) -0.014(3) O008 0.120(5) 0.035(3) 0.056(3) 0.004(3) 0.004(3) 0.030(3) N009 0.043(3) 0.037(3) 0.024(3) -0.003(3) 0.001(2) -0.002(3) N00A 0.072(5) 0.047(4) 0.034(3) -0.004(3) 0.008(3) 0.011(3) C00B 0.039(4) 0.028(3) 0.034(3) -0.003(3) 0.003(3) 0.011(3) C00C 0.047(4) 0.028(3) 0.027(3) 0.004(3) -0.002(3) 0.009(3) C00D 0.054(5) 0.036(4) 0.029(3) -0.003(3) -0.003(3) 0.003(4) C00E 0.051(5) 0.044(4) 0.044(4) -0.001(4) 0.000(4) 0.002(4) C00F 0.046(5) 0.032(4) 0.037(4) -0.001(3) 0.004(3) 0.002(3) C00G 0.057(5) 0.022(3) 0.035(4) -0.009(3) 0.004(3) -0.002(3) C00H 0.043(4) 0.027(3) 0.031(3) -0.003(3) 0.007(3) 0.007(3) C00I 0.042(5) 0.035(4) 0.033(4) 0.004(3) 0.004(3) 0.005(3) C00J 0.047(5) 0.038(4) 0.033(4) 0.003(3) 0.002(3) -0.002(4) C00K 0.045(5) 0.043(4) 0.027(3) -0.005(4) 0.002(3) -0.011(4) C00L 0.053(5) 0.045(4) 0.042(4) 0.000(4) -0.006(4) 0.000(4) C00M 0.053(5) 0.048(4) 0.041(4) 0.017(4) -0.002(4) -0.001(4) C00N 0.065(6) 0.039(4) 0.034(4) -0.003(4) -0.005(4) 0.011(4) C00O 0.052(5) 0.032(4) 0.035(4) -0.004(3) 0.001(3) -0.001(3) C00P 0.053(5) 0.043(4) 0.035(4) 0.018(4) -0.002(3) -0.007(4) C00Q 0.070(6) 0.037(4) 0.049(4) 0.009(4) 0.010(4) 0.013(4) C00R 0.060(6) 0.063(5) 0.044(4) 0.002(4) 0.012(4) 0.003(4) C00S 0.036(5) 0.060(5) 0.034(4) 0.005(4) 0.004(3) 0.001(4) C00T 0.092(7) 0.044(4) 0.049(4) -0.011(4) -0.018(4) -0.008(5) C00U 0.062(5) 0.058(5) 0.043(4) -0.008(4) -0.006(4) -0.003(4) C00V 0.060(6) 0.065(5) 0.036(4) 0.017(4) 0.000(4) -0.010(4) C00W 0.042(5) 0.067(5) 0.063(5) 0.012(5) 0.020(4) 0.010(4) C00X 0.122(9) 0.035(5) 0.061(5) 0.003(4) 0.016(5) 0.010(5) C00Y 0.072(6) 0.073(6) 0.035(4) -0.011(5) 0.002(4) 0.008(5) C00Z 0.089(7) 0.055(5) 0.062(5) -0.015(5) 0.005(5) 0.016(5) C010 0.042(5) 0.080(6) 0.051(5) 0.003(5) -0.004(4) 0.010(4) C011 0.050(5) 0.044(5) 0.084(6) -0.011(5) 0.017(5) -0.002(4) C012 0.080(7) 0.085(6) 0.031(4) -0.003(5) 0.010(4) 0.003(5) C013 0.077(6) 0.069(6) 0.038(4) -0.001(4) 0.002(4) 0.011(5) C014 0.114(8) 0.046(5) 0.068(6) -0.020(5) 0.028(6) -0.023(5) C015 0.111(8) 0.060(5) 0.069(6) -0.016(5) -0.023(6) -0.016(6) C016 0.093(7) 0.074(6) 0.056(5) 0.000(5) 0.019(5) 0.014(5) C017 0.063(6) 0.059(5) 0.078(6) 0.024(5) 0.019(5) 0.005(5) C018 0.146(10) 0.058(6) 0.099(7) -0.011(6) 0.041(7) 0.016(6) C019 0.051(6) 0.078(6) 0.077(6) -0.008(6) -0.012(5) 0.015(5) C01A 0.065(7) 0.056(5) 0.184(10) 0.013(7) 0.027(7) 0.019(5) 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' Cl Cl 0.1484 0.1585 '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 _geom_angle_publ_flag O005 S01 N009 106.0(3) . . ? O005 S01 C00S 109.7(3) . . ? O007 S01 O005 120.5(3) . . ? O007 S01 N009 104.2(3) . . ? O007 S01 C00S 108.6(3) . . ? N009 S01 C00S 106.9(3) . . ? C00F S002 C00L 90.4(3) . . ? C00N O004 C00Z 119.3(6) . . ? C00B N009 S01 118.6(4) . . ? C00B N009 C00H 105.5(5) . . ? C00H N009 S01 113.3(4) . . ? C00E N00A C00K 111.4(6) . . ? C00E N00A C016 122.2(6) . . ? C00K N00A C016 126.3(6) . . ? N009 C00B C00D 136.0(6) . . ? C00F C00B N009 111.9(5) . . ? C00F C00B C00D 111.9(6) . . ? C00F C00C H00C 108.4 . . ? C00F C00C C00G 114.4(5) . . ? C00F C00C C00H 100.8(5) . . ? C00G C00C H00C 108.4 . . ? C00G C00C C00H 116.2(5) . . ? C00H C00C H00C 108.4 . . ? C00L C00D C00B 110.1(6) . . ? C00L C00D C00U 118.0(6) . . ? C00U C00D C00B 131.8(7) . . ? O008 C00E N00A 125.3(7) . . ? O008 C00E C00J 128.9(7) . . ? N00A C00E C00J 105.8(6) . . ? C00B C00F S002 114.4(5) . . ? C00B C00F C00C 113.1(6) . . ? C00C C00F S002 132.2(5) . . ? C00Q C00G C00C 122.2(6) . . ? C00Q C00G C00T 117.8(6) . . ? C00T C00G C00C 119.8(6) . . ? N009 C00H C00C 107.3(5) . . ? N009 C00H H00H 108.6 . . ? C00C C00H H00H 108.6 . . ? C00O C00H N009 109.1(5) . . ? C00O C00H C00C 114.6(5) . . ? C00O C00H H00H 108.6 . . ? C00K C00I C00J 107.6(6) . . ? C00P C00I C00J 134.4(6) . . ? C00P C00I C00K 118.0(6) . . ? C00I C00J C00E 105.1(5) . . ? C00O C00J C00E 122.7(6) . . ? C00O C00J C00I 132.1(6) . . ? C00I C00K N00A 109.9(6) . . ? C013 C00K N00A 125.4(7) . . ? C013 C00K C00I 124.7(7) . . ? C00D C00L S002 113.1(5) . . ? C00R C00L S002 124.4(6) . . ? C00R C00L C00D 122.5(6) . . ? C00P C00M Cl03 118.7(6) . . ? C00V C00M Cl03 118.5(6) . . ? C00V C00M C00P 122.8(7) . . ? O004 C00N C00O 110.9(6) . . ? O006 C00N O004 124.1(7) . . ? O006 C00N C00O 125.0(8) . . ? C00H C00O C00N 113.9(5) . . ? C00J C00O C00H 124.5(6) . . ? C00J C00O C00N 121.6(6) . . ? C00I C00P H00P 120.9 . . ? C00M C00P C00I 118.2(7) . . ? C00M C00P H00P 120.9 . . ? C00G C00Q H00Q 119.6 . . ? C00G C00Q C00X 120.7(7) . . ? C00X C00Q H00Q 119.6 . . ? C00L C00R H00R 121.0 . . ? C012 C00R C00L 118.0(7) . . ? C012 C00R H00R 121.0 . . ? C00W C00S S01 118.1(6) . . ? C010 C00S S01 118.9(6) . . ? C010 C00S C00W 122.9(7) . . ? C00G C00T H00T 119.7 . . ? C015 C00T C00G 120.7(7) . . ? C015 C00T H00T 119.7 . . ? C00D C00U H00U 120.8 . . ? C00Y C00U C00D 118.4(7) . . ? C00Y C00U H00U 120.8 . . ? C00M C00V H00V 120.0 . . ? C00M C00V C013 120.0(7) . . ? C013 C00V H00V 120.0 . . ? C00S C00W H00W 121.5 . . ? C00S C00W C017 116.9(7) . . ? C017 C00W H00W 121.5 . . ? C00Q C00X H00X 119.7 . . ? C014 C00X C00Q 120.6(8) . . ? C014 C00X H00X 119.7 . . ? C00U C00Y H00Y 118.4 . . ? C00U C00Y C012 123.2(7) . . ? C012 C00Y H00Y 118.4 . . ? O004 C00Z H00A 109.6 . . ? O004 C00Z H00B 109.6 . . ? H00A C00Z H00B 108.2 . . ? C018 C00Z O004 110.1(7) . . ? C018 C00Z H00A 109.6 . . ? C018 C00Z H00B 109.6 . . ? C00S C010 H010 121.1 . . ? C00S C010 C019 117.8(8) . . ? C019 C010 H010 121.1 . . ? C017 C011 C019 118.3(8) . . ? C017 C011 C01A 120.9(8) . . ? C019 C011 C01A 120.7(8) . . ? C00R C012 C00Y 119.7(7) . . ? C00R C012 H012 120.2 . . ? C00Y C012 H012 120.2 . . ? C00K C013 C00V 116.1(7) . . ? C00K C013 H013 121.9 . . ? C00V C013 H013 121.9 . . ? C00X C014 H014 120.0 . . ? C015 C014 C00X 120.0(8) . . ? C015 C014 H014 120.0 . . ? C00T C015 H015 120.0 . . ? C014 C015 C00T 120.1(7) . . ? C014 C015 H015 120.0 . . ? N00A C016 H01A 109.5 . . ? N00A C016 H01B 109.5 . . ? N00A C016 H01C 109.5 . . ? H01A C016 H01B 109.5 . . ? H01A C016 H01C 109.5 . . ? H01B C016 H01C 109.5 . . ? C00W C017 H017 118.9 . . ? C011 C017 C00W 122.2(8) . . ? C011 C017 H017 118.9 . . ? C00Z C018 H01D 109.5 . . ? C00Z C018 H01E 109.5 . . ? C00Z C018 H01F 109.5 . . ? H01D C018 H01E 109.5 . . ? H01D C018 H01F 109.5 . . ? H01E C018 H01F 109.5 . . ? C010 C019 H019 119.1 . . ? C011 C019 C010 121.9(8) . . ? C011 C019 H019 119.1 . . ? C011 C01A H01G 109.5 . . ? C011 C01A H01H 109.5 . . ? C011 C01A H01I 109.5 . . ? H01G C01A H01H 109.5 . . ? H01G C01A H01I 109.5 . . ? H01H C01A H01I 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 O005 1.429(4) . ? S01 O007 1.427(4) . ? S01 N009 1.672(5) . ? S01 C00S 1.792(7) . ? S002 C00F 1.705(7) . ? S002 C00L 1.737(6) . ? Cl03 C00M 1.759(7) . ? O004 C00N 1.329(8) . ? O004 C00Z 1.458(8) . ? O006 C00N 1.200(8) . ? O008 C00E 1.219(7) . ? N009 C00B 1.428(7) . ? N009 C00H 1.523(6) . ? N00A C00E 1.352(8) . ? N00A C00K 1.420(8) . ? N00A C016 1.434(8) . ? C00B C00D 1.446(8) . ? C00B C00F 1.378(8) . ? C00C H00C 0.9800 . ? C00C C00F 1.486(7) . ? C00C C00G 1.519(7) . ? C00C C00H 1.577(8) . ? C00D C00L 1.405(9) . ? C00D C00U 1.422(8) . ? C00E C00J 1.536(9) . ? C00G C00Q 1.386(8) . ? C00G C00T 1.398(8) . ? C00H H00H 0.9800 . ? C00H C00O 1.512(8) . ? C00I C00J 1.464(8) . ? C00I C00K 1.379(8) . ? C00I C00P 1.379(8) . ? C00J C00O 1.345(8) . ? C00K C013 1.365(8) . ? C00L C00R 1.397(8) . ? C00M C00P 1.379(8) . ? C00M C00V 1.359(9) . ? C00N C00O 1.513(8) . ? C00P H00P 0.9300 . ? C00Q H00Q 0.9300 . ? C00Q C00X 1.387(9) . ? C00R H00R 0.9300 . ? C00R C012 1.384(9) . ? C00S C00W 1.374(8) . ? C00S C010 1.364(9) . ? C00T H00T 0.9300 . ? C00T C015 1.393(9) . ? C00U H00U 0.9300 . ? C00U C00Y 1.362(8) . ? C00V H00V 0.9300 . ? C00V C013 1.396(9) . ? C00W H00W 0.9300 . ? C00W C017 1.404(9) . ? C00X H00X 0.9300 . ? C00X C014 1.366(10) . ? C00Y H00Y 0.9300 . ? C00Y C012 1.394(10) . ? C00Z H00A 0.9700 . ? C00Z H00B 0.9700 . ? C00Z C018 1.418(9) . ? C010 H010 0.9300 . ? C010 C019 1.391(10) . ? C011 C017 1.362(10) . ? C011 C019 1.373(10) . ? C011 C01A 1.530(9) . ? C012 H012 0.9300 . ? C013 H013 0.9300 . ? C014 H014 0.9300 . ? C014 C015 1.366(10) . ? C015 H015 0.9300 . ? C016 H01A 0.9600 . ? C016 H01B 0.9600 . ? C016 H01C 0.9600 . ? C017 H017 0.9300 . ? C018 H01D 0.9600 . ? C018 H01E 0.9600 . ? C018 H01F 0.9600 . ? C019 H019 0.9300 . ? C01A H01G 0.9600 . ? C01A H01H 0.9600 . ? C01A H01I 0.9600 . ?