#------------------------------------------------------------------------------ #$Date: 2021-03-25 06:54:06 +0200 (Thu, 25 Mar 2021) $ #$Revision: 263304 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157989.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_7157989 loop_ _publ_author_name 'Chang, Li' 'Zhu, Guang-Yu' 'Yang, Ting' 'Zhao, Xiao-li' 'Shi, Min' 'Zhao, Mei-Xin' _publ_section_title ; Organocatalytic Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoacetates with Saccharin-Derived 1-Azadienes ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00115A _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C25 H19 Br N2 O4 S' _chemical_formula_sum 'C25 H19 Br N2 O4 S' _chemical_formula_weight 523.39 _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 2018-05-03 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492) ; _audit_update_record ; 2020-06-18 deposited with the CCDC. 2021-03-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.73540(10) _cell_length_b 18.2897(2) _cell_length_c 19.0257(2) _cell_measurement_reflns_used 15522 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 74.0150 _cell_measurement_theta_min 4.6420 _cell_volume 2343.75(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)' _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -58.00 1.00 1.00 -- 0.00 -38.00 90.00 30 2 \w -15.00 29.00 1.00 1.00 -- 0.00 38.00 60.00 44 3 \w -55.00 18.00 1.00 1.00 -- 0.00 -38.00 90.00 73 4 \w 64.00 89.00 1.00 1.00 -- 0.00 77.00-150.00 25 5 \w -57.00 19.00 1.00 1.00 -- 0.00 -38.00 0.00 76 6 \w -80.00 18.00 1.00 1.00 -- 0.00 -38.00-120.00 98 7 \w 6.00 52.00 1.00 2.00 -- 95.80 -45.00-120.00 46 8 \w 78.00 185.00 1.00 2.00 -- 95.80 30.00 60.00 107 9 \w 7.00 33.00 1.00 2.00 -- 95.80 -45.00 90.00 26 10 \w 76.00 102.00 1.00 2.00 -- 95.80 -82.00-150.00 26 11 \w 96.00 124.00 1.00 2.00 -- 95.80 -82.00 150.00 28 12 \w 7.00 120.00 1.00 2.00 -- 95.80 -61.00 60.00 113 13 \w 77.00 173.00 1.00 2.00 -- 95.80 15.00 30.00 96 14 \w 18.00 128.00 1.00 2.00 -- 95.80 -82.00 -60.00 110 15 \w 7.00 114.00 1.00 2.00 -- 95.80 -61.00 -60.00 107 16 \w 16.00 119.00 1.00 2.00 -- 95.80 -15.00 90.00 103 17 \w 46.00 105.00 1.00 2.00 -- 95.80 -61.00 150.00 59 18 \w 42.00 128.00 1.00 2.00 -- 95.80 -82.00 60.00 86 19 \w 100.00 128.00 1.00 2.00 -- 95.80 -82.00 90.00 28 20 \w 61.00 86.00 1.00 2.00 -- 95.80 -45.00 90.00 25 21 \w 73.00 98.00 1.00 2.00 -- 95.80 -82.00 30.00 25 22 \w 96.00 122.00 1.00 2.00 -- 95.80 -82.00 120.00 26 23 \w 77.00 102.00 1.00 2.00 -- 95.80 -82.00 133.99 25 24 \w 15.00 41.00 1.00 2.00 -- 95.80 -82.00 133.99 26 ; _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 0.0663078000 _diffrn_orient_matrix_UB_12 -0.0799646000 _diffrn_orient_matrix_UB_13 -0.0095926000 _diffrn_orient_matrix_UB_21 0.0023208000 _diffrn_orient_matrix_UB_22 0.0106646000 _diffrn_orient_matrix_UB_23 -0.0803072000 _diffrn_orient_matrix_UB_31 0.2189920000 _diffrn_orient_matrix_UB_32 0.0241309000 _diffrn_orient_matrix_UB_33 0.0037330000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_unetI/netI 0.0336 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 23450 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.073 _diffrn_reflns_theta_max 67.073 _diffrn_reflns_theta_min 4.648 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.514 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.33992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) 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 1.483 _exptl_crystal_description block _exptl_crystal_F_000 1064 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.35 _refine_diff_density_max 1.077 _refine_diff_density_min -0.832 _refine_diff_density_rms 0.062 _refine_ls_abs_structure_details ; Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.008(8) _refine_ls_extinction_coef 0.0026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 4171 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0488 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+2.4123P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1277 _refine_ls_wR_factor_ref 0.1286 _reflns_Friedel_coverage 0.734 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 4040 _reflns_number_total 4171 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00115a2.cif _cod_data_source_block exp_334 _cod_database_code 7157989 _shelx_shelxl_version_number 2016/6 _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 0.373 _shelx_estimated_absorpt_t_min 0.313 _reflns_odcompleteness_completeness 99.88 _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 N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C9(H9) 2.b Aromatic/amide H refined with riding coordinates: N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23) 2.c Idealised Me refined as rotating group: C25(H25A,H25B,H25C) ; _shelx_res_file ; TITL exp_334_a.res in P2(1)2(1)2(1) exp_334.res created by SHELXL-2016/6 at 09:50:48 on 03-May-2018 REM Old TITL exp_334 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.280, Rweak 0.125, Alpha 0.010, Orientation as input REM Flack x = 0.212 ( 0.008 ) from Parsons' quotients REM Formula found by SHELXT: C24 N3 O4 S2 CELL 1.54184 6.7354 18.2897 19.0257 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 N O S UNIT 100 76 4 8 16 4 L.S. 64 PLAN 6 SIZE 0.43 0.37 0.35 BOND $H list 4 fmap 2 53 ACTA SHEL 999 0.837 OMIT 0 1 14 OMIT 5 1 0 OMIT -4 1 14 OMIT 4 1 14 OMIT 4 3 4 OMIT 0 6 3 OMIT 0 6 4 REM REM REM WGHT 0.064000 2.412300 EXTI 0.002630 FVAR 0.60390 BR1 3 0.002265 0.485126 0.394131 11.00000 0.17439 0.10061 = 0.04604 0.02322 -0.01473 0.02677 S1 6 0.400965 0.140043 0.852180 11.00000 0.05594 0.02168 = 0.07184 0.00757 -0.00135 0.00699 O1 5 0.283249 0.119095 0.911326 11.00000 0.07844 0.05116 = 0.09002 0.03197 0.00897 -0.00362 O2 5 0.441958 0.083666 0.801836 11.00000 0.09305 0.03190 = 0.11272 -0.02192 -0.02101 0.02207 O3 5 -0.055621 0.450236 0.788349 11.00000 0.05970 0.04595 = 0.07339 -0.00306 0.02751 -0.00039 O4 5 0.134795 0.539057 0.746218 11.00000 0.06800 0.02802 = 0.06589 -0.01022 0.01229 0.00167 N1 4 0.306346 0.209584 0.810106 11.00000 0.04407 0.01968 = 0.05345 0.00305 -0.00179 0.00065 N2 4 0.416409 0.438588 0.719587 11.00000 0.03462 0.02371 = 0.04597 0.00571 -0.00128 -0.00379 AFIX 43 H2 2 0.477975 0.475797 0.702595 11.00000 -1.20000 AFIX 0 C1 1 0.608442 0.255806 0.857517 11.00000 0.04216 0.03599 = 0.03845 0.00226 0.00252 0.00264 C2 1 0.750309 0.305129 0.880592 11.00000 0.05668 0.05673 = 0.05238 0.00418 -0.01509 -0.01046 AFIX 43 H2A 2 0.745898 0.353816 0.866581 11.00000 -1.20000 AFIX 0 C3 1 0.899207 0.280331 0.925079 11.00000 0.05473 0.09696 = 0.06111 0.00604 -0.01687 -0.01009 AFIX 43 H3 2 0.994749 0.313121 0.940944 11.00000 -1.20000 AFIX 0 C4 1 0.909075 0.208535 0.946292 11.00000 0.05880 0.09830 = 0.06112 0.00803 -0.01446 0.02601 AFIX 43 H4 2 1.011444 0.193137 0.975565 11.00000 -1.20000 AFIX 0 C5 1 0.764499 0.158555 0.923711 11.00000 0.07577 0.05487 = 0.06522 0.00746 -0.00845 0.02416 AFIX 43 H5 2 0.768193 0.109760 0.937399 11.00000 -1.20000 AFIX 0 C6 1 0.618503 0.184488 0.880902 11.00000 0.04916 0.04020 = 0.05213 0.00525 0.00223 0.01438 C7 1 0.425799 0.266260 0.812531 11.00000 0.03910 0.02430 = 0.03737 -0.00164 -0.00052 0.00333 C8 1 0.380924 0.329923 0.773016 11.00000 0.03967 0.02295 = 0.03664 -0.00309 -0.00437 -0.00255 C9 1 0.191446 0.339070 0.730039 11.00000 0.03370 0.02072 = 0.03669 0.00054 -0.00069 -0.00342 AFIX 13 H9 2 0.076223 0.333598 0.761050 11.00000 -1.20000 AFIX 0 C10 1 0.207903 0.421848 0.705643 11.00000 0.03696 0.01980 = 0.03806 0.00090 -0.00313 -0.00304 C11 1 0.499499 0.389184 0.761829 11.00000 0.03258 0.02803 = 0.04030 -0.00720 -0.00281 0.00161 AFIX 43 H11 2 0.624971 0.394562 0.781567 11.00000 -1.20000 AFIX 0 C12 1 0.172702 0.286167 0.669260 11.00000 0.05050 0.02225 = 0.03890 0.00105 -0.00795 -0.00934 C13 1 0.336667 0.254464 0.638061 11.00000 0.06237 0.03603 = 0.05145 -0.01028 0.00162 -0.00150 AFIX 43 H13 2 0.462655 0.263650 0.656008 11.00000 -1.20000 AFIX 0 C14 1 0.314730 0.208584 0.579600 11.00000 0.10492 0.04298 = 0.05221 -0.01375 0.01536 -0.00485 AFIX 43 H14 2 0.426096 0.187621 0.558890 11.00000 -1.20000 AFIX 0 C15 1 0.131543 0.194624 0.553085 11.00000 0.13682 0.05017 = 0.04516 -0.00727 -0.01379 -0.03389 AFIX 43 H15 2 0.117489 0.164337 0.514137 11.00000 -1.20000 AFIX 0 C16 1 -0.031097 0.224927 0.583492 11.00000 0.10005 0.05680 = 0.06343 0.00839 -0.03686 -0.03392 AFIX 43 H16 2 -0.156171 0.215135 0.565048 11.00000 -1.20000 AFIX 0 C17 1 -0.013813 0.270464 0.641883 11.00000 0.06007 0.03860 = 0.05411 0.00625 -0.01810 -0.01597 AFIX 43 H17 2 -0.126824 0.290309 0.662495 11.00000 -1.20000 AFIX 0 C18 1 0.155407 0.437548 0.628953 11.00000 0.04427 0.02005 = 0.03790 -0.00159 -0.00207 0.00345 C19 1 0.299706 0.432436 0.577603 11.00000 0.05643 0.05098 = 0.04159 0.00598 0.01115 0.01168 AFIX 43 H19 2 0.428209 0.419120 0.590092 11.00000 -1.20000 AFIX 0 C20 1 0.255910 0.446892 0.507451 11.00000 0.09551 0.05504 = 0.03688 0.00496 0.01012 0.01677 AFIX 43 H20 2 0.353966 0.444014 0.473148 11.00000 -1.20000 AFIX 0 C21 1 0.064726 0.465485 0.490091 11.00000 0.10117 0.03486 = 0.04041 0.00469 -0.00322 0.01325 C22 1 -0.078777 0.471654 0.538746 11.00000 0.06496 0.05024 = 0.05239 0.00348 -0.01526 0.01127 AFIX 43 H22 2 -0.206555 0.485415 0.525779 11.00000 -1.20000 AFIX 0 C23 1 -0.033692 0.457106 0.609302 11.00000 0.05442 0.04688 = 0.04320 -0.00131 -0.00279 0.00878 AFIX 43 H23 2 -0.132750 0.460724 0.643177 11.00000 -1.20000 AFIX 0 C24 1 0.078221 0.470472 0.752505 11.00000 0.03753 0.02579 = 0.03989 -0.00277 -0.00826 -0.00220 C25 1 0.030372 0.594077 0.786944 11.00000 0.09189 0.04171 = 0.08834 -0.03069 -0.00423 0.02518 AFIX 137 H25A 2 -0.098385 0.602310 0.766803 11.00000 -1.50000 H25B 2 0.104711 0.638858 0.786438 11.00000 -1.50000 H25C 2 0.015741 0.577445 0.834521 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_334_a.res in P2(1)2(1)2(1) REM R1 = 0.0488 for 4040 Fo > 4sig(Fo) and 0.0499 for all 4171 data REM 300 parameters refined using 0 restraints END WGHT 0.0640 2.4117 REM Highest difference peak 1.077, deepest hole -0.832, 1-sigma level 0.062 Q1 1 0.0978 0.5242 0.4018 11.00000 0.05 1.08 Q2 1 -0.1214 0.4933 0.4119 11.00000 0.05 0.77 Q3 1 0.0043 0.4740 0.3813 11.00000 0.05 0.27 Q4 1 -0.0809 0.4146 0.4130 11.00000 0.05 0.21 Q5 1 0.5162 0.1807 0.8425 11.00000 0.05 0.21 Q6 1 0.1333 0.6074 0.8215 11.00000 0.05 0.20 ; _shelx_res_checksum 238 _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 2.305 _oxdiff_exptl_absorpt_empirical_full_min 0.538 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 Br1 Br 0.0023(2) 0.48513(5) 0.39413(4) 0.1070(5) Uani 1 1 d . . . . . S1 S 0.4010(2) 0.14004(6) 0.85218(8) 0.0498(4) Uani 1 1 d . . . . . O1 O 0.2832(8) 0.1191(2) 0.9113(3) 0.0732(13) Uani 1 1 d . . . . . O2 O 0.4420(8) 0.0837(2) 0.8018(3) 0.0792(15) Uani 1 1 d . . . . . O3 O -0.0556(6) 0.4502(2) 0.7883(2) 0.0597(11) Uani 1 1 d . . . . . O4 O 0.1348(6) 0.53906(18) 0.7462(2) 0.0540(10) Uani 1 1 d . . . . . N1 N 0.3063(6) 0.20958(19) 0.8101(2) 0.0391(9) Uani 1 1 d . . . . . N2 N 0.4164(5) 0.43859(19) 0.7196(2) 0.0348(8) Uani 1 1 d . . . . . H2 H 0.477975 0.475797 0.702595 0.042 Uiso 1 1 calc R . . . . C1 C 0.6084(7) 0.2558(3) 0.8575(3) 0.0389(10) Uani 1 1 d . . . . . C2 C 0.7503(9) 0.3051(3) 0.8806(3) 0.0553(14) Uani 1 1 d . . . . . H2A H 0.745898 0.353816 0.866581 0.066 Uiso 1 1 calc R . . . . C3 C 0.8992(10) 0.2803(5) 0.9251(4) 0.0709(18) Uani 1 1 d . . . . . H3 H 0.994749 0.313121 0.940944 0.085 Uiso 1 1 calc R . . . . C4 C 0.9091(11) 0.2085(5) 0.9463(4) 0.073(2) Uani 1 1 d . . . . . H4 H 1.011444 0.193137 0.975565 0.087 Uiso 1 1 calc R . . . . C5 C 0.7645(10) 0.1586(4) 0.9237(4) 0.0653(17) Uani 1 1 d . . . . . H5 H 0.768193 0.109760 0.937399 0.078 Uiso 1 1 calc R . . . . C6 C 0.6185(8) 0.1845(3) 0.8809(3) 0.0472(12) Uani 1 1 d . . . . . C7 C 0.4258(7) 0.2663(2) 0.8125(2) 0.0336(9) Uani 1 1 d . . . . . C8 C 0.3809(7) 0.3299(2) 0.7730(2) 0.0331(9) Uani 1 1 d . . . . . C9 C 0.1914(7) 0.3391(2) 0.7300(2) 0.0304(9) Uani 1 1 d . . . . . H9 H 0.076223 0.333598 0.761050 0.036 Uiso 1 1 calc R . . . . C10 C 0.2079(7) 0.4218(2) 0.7056(2) 0.0316(9) Uani 1 1 d . . . . . C11 C 0.4995(7) 0.3892(2) 0.7618(2) 0.0336(9) Uani 1 1 d . . . . . H11 H 0.624971 0.394562 0.781567 0.040 Uiso 1 1 calc R . . . . C12 C 0.1727(8) 0.2862(2) 0.6693(2) 0.0372(10) Uani 1 1 d . . . . . C13 C 0.3367(9) 0.2545(3) 0.6381(3) 0.0500(13) Uani 1 1 d . . . . . H13 H 0.462655 0.263650 0.656008 0.060 Uiso 1 1 calc R . . . . C14 C 0.3147(13) 0.2086(3) 0.5796(3) 0.0667(18) Uani 1 1 d . . . . . H14 H 0.426096 0.187621 0.558890 0.080 Uiso 1 1 calc R . . . . C15 C 0.1315(16) 0.1946(4) 0.5531(3) 0.077(2) Uani 1 1 d . . . . . H15 H 0.117489 0.164337 0.514137 0.093 Uiso 1 1 calc R . . . . C16 C -0.0311(13) 0.2249(4) 0.5835(4) 0.073(2) Uani 1 1 d . . . . . H16 H -0.156171 0.215135 0.565048 0.088 Uiso 1 1 calc R . . . . C17 C -0.0138(9) 0.2705(3) 0.6419(3) 0.0509(13) Uani 1 1 d . . . . . H17 H -0.126824 0.290309 0.662495 0.061 Uiso 1 1 calc R . . . . C18 C 0.1554(7) 0.4375(2) 0.6290(2) 0.0341(10) Uani 1 1 d . . . . . C19 C 0.2997(9) 0.4324(3) 0.5776(3) 0.0497(13) Uani 1 1 d . . . . . H19 H 0.428209 0.419120 0.590092 0.060 Uiso 1 1 calc R . . . . C20 C 0.2559(11) 0.4469(3) 0.5075(3) 0.0625(17) Uani 1 1 d . . . . . H20 H 0.353966 0.444014 0.473148 0.075 Uiso 1 1 calc R . . . . C21 C 0.0647(11) 0.4655(3) 0.4901(3) 0.0588(16) Uani 1 1 d . . . . . C22 C -0.0788(10) 0.4717(3) 0.5387(3) 0.0559(14) Uani 1 1 d . . . . . H22 H -0.206555 0.485415 0.525779 0.067 Uiso 1 1 calc R . . . . C23 C -0.0337(8) 0.4571(3) 0.6093(3) 0.0482(12) Uani 1 1 d . . . . . H23 H -0.132750 0.460724 0.643177 0.058 Uiso 1 1 calc R . . . . C24 C 0.0782(7) 0.4705(2) 0.7525(2) 0.0344(10) Uani 1 1 d . . . . . C25 C 0.0304(12) 0.5941(3) 0.7869(4) 0.074(2) Uani 1 1 d . . . . . H25A H -0.098385 0.602310 0.766803 0.111 Uiso 1 1 calc GR . . . . H25B H 0.104711 0.638858 0.786438 0.111 Uiso 1 1 calc GR . . . . H25C H 0.015741 0.577445 0.834521 0.111 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 Br1 0.1744(11) 0.1006(7) 0.0460(4) 0.0232(4) -0.0147(5) 0.0268(7) S1 0.0559(7) 0.0217(5) 0.0718(9) 0.0076(5) -0.0013(7) 0.0070(5) O1 0.078(3) 0.051(2) 0.090(3) 0.032(2) 0.009(3) -0.004(2) O2 0.093(3) 0.0319(19) 0.113(4) -0.022(2) -0.021(3) 0.022(2) O3 0.060(2) 0.046(2) 0.073(3) -0.0031(18) 0.028(2) -0.0004(18) O4 0.068(2) 0.0280(16) 0.066(2) -0.0102(16) 0.0123(19) 0.0017(16) N1 0.044(2) 0.0197(17) 0.053(2) 0.0030(17) -0.0018(19) 0.0006(16) N2 0.0346(18) 0.0237(16) 0.046(2) 0.0057(15) -0.0013(16) -0.0038(15) C1 0.042(2) 0.036(2) 0.038(2) 0.0023(19) 0.003(2) 0.0026(19) C2 0.057(3) 0.057(3) 0.052(3) 0.004(3) -0.015(3) -0.010(3) C3 0.055(3) 0.097(5) 0.061(4) 0.006(4) -0.017(3) -0.010(4) C4 0.059(4) 0.098(5) 0.061(4) 0.008(4) -0.014(3) 0.026(4) C5 0.076(4) 0.055(4) 0.065(4) 0.007(3) -0.008(3) 0.024(3) C6 0.049(3) 0.040(3) 0.052(3) 0.005(2) 0.002(2) 0.014(2) C7 0.039(2) 0.024(2) 0.037(2) -0.0016(17) -0.0005(19) 0.0033(18) C8 0.040(2) 0.0229(19) 0.037(2) -0.0031(17) -0.0044(19) -0.0026(17) C9 0.034(2) 0.0207(18) 0.037(2) 0.0005(17) -0.0007(18) -0.0034(16) C10 0.037(2) 0.0198(19) 0.038(2) 0.0009(16) -0.0031(19) -0.0030(17) C11 0.0326(19) 0.0280(19) 0.040(2) -0.0072(17) -0.0028(19) 0.0016(17) C12 0.050(3) 0.0222(19) 0.039(2) 0.0010(18) -0.008(2) -0.0093(19) C13 0.062(3) 0.036(2) 0.051(3) -0.010(2) 0.002(3) -0.002(2) C14 0.105(5) 0.043(3) 0.052(3) -0.014(3) 0.015(4) -0.005(3) C15 0.137(7) 0.050(3) 0.045(3) -0.007(3) -0.014(4) -0.034(4) C16 0.100(6) 0.057(4) 0.063(4) 0.008(3) -0.037(4) -0.034(4) C17 0.060(3) 0.039(3) 0.054(3) 0.006(2) -0.018(3) -0.016(2) C18 0.044(2) 0.0200(18) 0.038(2) -0.0016(17) -0.0021(19) 0.0034(17) C19 0.056(3) 0.051(3) 0.042(3) 0.006(2) 0.011(2) 0.012(3) C20 0.096(5) 0.055(3) 0.037(3) 0.005(3) 0.010(3) 0.017(3) C21 0.101(5) 0.035(3) 0.040(3) 0.005(2) -0.003(3) 0.013(3) C22 0.065(3) 0.050(3) 0.052(3) 0.003(2) -0.015(3) 0.011(3) C23 0.054(3) 0.047(3) 0.043(3) -0.001(2) -0.003(2) 0.009(2) C24 0.038(2) 0.026(2) 0.040(2) -0.0028(17) -0.008(2) -0.0022(18) C25 0.092(5) 0.042(3) 0.088(5) -0.031(3) -0.004(4) 0.025(3) 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' N N 0.0311 0.0180 '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 O1 S1 O2 116.1(3) . . ? O1 S1 N1 112.2(3) . . ? O1 S1 C6 109.9(3) . . ? O2 S1 N1 107.9(3) . . ? O2 S1 C6 112.2(3) . . ? N1 S1 C6 96.7(2) . . ? C24 O4 C25 118.1(5) . . ? C7 N1 S1 111.0(3) . . ? C10 N2 H2 124.1 . . ? C11 N2 H2 124.1 . . ? C11 N2 C10 111.8(4) . . ? C2 C1 C7 131.2(4) . . ? C6 C1 C2 118.7(5) . . ? C6 C1 C7 110.0(4) . . ? C1 C2 H2A 120.7 . . ? C1 C2 C3 118.6(6) . . ? C3 C2 H2A 120.7 . . ? C2 C3 H3 119.1 . . ? C4 C3 C2 121.7(7) . . ? C4 C3 H3 119.1 . . ? C3 C4 H4 120.0 . . ? C3 C4 C5 119.9(6) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 121.4 . . ? C6 C5 C4 117.2(6) . . ? C6 C5 H5 121.4 . . ? C1 C6 S1 107.2(4) . . ? C5 C6 S1 128.7(5) . . ? C5 C6 C1 123.9(6) . . ? N1 C7 C1 114.8(4) . . ? N1 C7 C8 119.9(4) . . ? C8 C7 C1 125.3(4) . . ? C7 C8 C9 123.5(4) . . ? C11 C8 C7 127.6(4) . . ? C11 C8 C9 108.6(4) . . ? C8 C9 H9 109.2 . . ? C8 C9 C10 101.7(3) . . ? C10 C9 H9 109.2 . . ? C12 C9 C8 114.2(4) . . ? C12 C9 H9 109.2 . . ? C12 C9 C10 113.1(4) . . ? N2 C10 C9 102.3(3) . . ? N2 C10 C18 110.9(4) . . ? N2 C10 C24 108.7(3) . . ? C18 C10 C9 116.2(3) . . ? C18 C10 C24 108.3(3) . . ? C24 C10 C9 110.1(4) . . ? N2 C11 C8 112.8(4) . . ? N2 C11 H11 123.6 . . ? C8 C11 H11 123.6 . . ? C13 C12 C9 122.0(4) . . ? C13 C12 C17 118.3(5) . . ? C17 C12 C9 119.6(5) . . ? C12 C13 H13 119.7 . . ? C12 C13 C14 120.5(6) . . ? C14 C13 H13 119.7 . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.2(7) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 120.0 . . ? C16 C15 C14 119.9(6) . . ? C16 C15 H15 120.0 . . ? C15 C16 H16 119.4 . . ? C15 C16 C17 121.1(7) . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 119.9(6) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C10 120.0(4) . . ? C23 C18 C10 121.5(4) . . ? C23 C18 C19 118.5(5) . . ? C18 C19 H19 119.5 . . ? C18 C19 C20 121.1(6) . . ? C20 C19 H19 119.5 . . ? C19 C20 H20 120.8 . . ? C21 C20 C19 118.5(6) . . ? C21 C20 H20 120.8 . . ? C20 C21 Br1 118.9(5) . . ? C22 C21 Br1 119.0(5) . . ? C22 C21 C20 122.0(5) . . ? C21 C22 H22 120.4 . . ? C21 C22 C23 119.2(6) . . ? C23 C22 H22 120.4 . . ? C18 C23 C22 120.7(5) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? O3 C24 O4 124.6(4) . . ? O3 C24 C10 125.8(4) . . ? O4 C24 C10 109.6(4) . . ? O4 C25 H25A 109.5 . . ? O4 C25 H25B 109.5 . . ? O4 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 Br1 C21 1.908(6) . ? S1 O1 1.429(5) . ? S1 O2 1.434(5) . ? S1 N1 1.632(4) . ? S1 C6 1.762(6) . ? O3 C24 1.189(6) . ? O4 C24 1.316(6) . ? O4 C25 1.452(7) . ? N1 C7 1.313(6) . ? N2 H2 0.8600 . ? N2 C10 1.462(6) . ? N2 C11 1.333(6) . ? C1 C2 1.385(8) . ? C1 C6 1.380(7) . ? C1 C7 1.511(7) . ? C2 H2A 0.9300 . ? C2 C3 1.388(9) . ? C3 H3 0.9300 . ? C3 C4 1.375(11) . ? C4 H4 0.9300 . ? C4 C5 1.403(11) . ? C5 H5 0.9300 . ? C5 C6 1.362(8) . ? C7 C8 1.419(6) . ? C8 C9 1.525(6) . ? C8 C11 1.363(6) . ? C9 H9 0.9800 . ? C9 C10 1.587(6) . ? C9 C12 1.513(6) . ? C10 C18 1.529(6) . ? C10 C24 1.533(6) . ? C11 H11 0.9300 . ? C12 C13 1.381(8) . ? C12 C17 1.390(8) . ? C13 H13 0.9300 . ? C13 C14 1.401(8) . ? C14 H14 0.9300 . ? C14 C15 1.357(12) . ? C15 H15 0.9300 . ? C15 C16 1.357(12) . ? C16 H16 0.9300 . ? C16 C17 1.393(9) . ? C17 H17 0.9300 . ? C18 C19 1.381(7) . ? C18 C23 1.375(7) . ? C19 H19 0.9300 . ? C19 C20 1.392(8) . ? C20 H20 0.9300 . ? C20 C21 1.372(10) . ? C21 C22 1.343(10) . ? C22 H22 0.9300 . ? C22 C23 1.402(8) . ? C23 H23 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ?