data_exp_20422 _audit_creation_date 2019-04-09 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelxl_version_number 2013-2 _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_id_orcid ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H18 Br N O3 S' _chemical_formula_sum 'C24 H18 Br N O3 S' _chemical_formula_weight 480.36 _chemical_absolute_configuration rm _chemical_melting_point ? 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' _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. ; _space_group_crystal_system 'orthorhombic' _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 5.4770(2) _cell_length_b 17.2742(5) _cell_length_c 22.0070(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2082.10(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4660 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 61.6080 _cell_measurement_theta_min 3.2540 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 3.847 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67630 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43 (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 1.532 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_unetI/netI 0.0491 _diffrn_reflns_Laue_measured_fraction_full 0.878 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 16569 _diffrn_reflns_point_group_measured_fraction_full 0.872 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 67.684 _diffrn_reflns_theta_min 3.252 _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1903 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.878 _diffrn_measured_fraction_theta_max 1.000 _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 -62.00 39.00 1.00 8.00 -- -32.31 38.00 -30.00 101 2 \w -109.00 -60.00 1.00 8.00 -- -32.31-178.00 -90.00 49 3 \w 10.00 103.00 1.00 8.00 -- 32.31 57.00-180.00 93 4 \w -36.00 56.00 1.00 8.00 -- 32.31 -57.00 30.00 92 5 \w 57.00 85.00 1.00 8.00 -- 32.31 158.00-160.00 28 6 \w 23.00 77.00 1.00 8.00 -- 32.31 -99.00 -90.00 54 7 \w -12.00 14.00 1.00 8.00 -- 32.31 -99.00 -90.00 26 8 \w 60.00 116.00 1.00 19.50 -- 94.50 -64.00 30.00 56 9 \w 130.00 157.00 1.00 19.50 -- 94.50 64.00-150.00 27 10 \w 22.00 59.00 1.00 19.50 -- 94.50-112.00 30.00 37 11 \w 25.00 88.00 1.00 19.50 -- 94.50 -64.00 150.00 63 12 \w 128.00 155.00 1.00 19.50 -- 94.50 12.00 -30.00 27 13 \w 95.00 127.00 1.00 19.50 -- 94.50 -25.00-150.00 32 14 \w 25.00 52.00 1.00 19.50 -- 94.50 -50.00 30.00 27 15 \w 72.00 99.00 1.00 19.50 -- 94.50 64.00-150.00 27 16 \w 25.00 102.00 1.00 19.50 -- 94.50 -64.00-150.00 77 17 \w 26.00 53.00 1.00 19.50 -- 94.50-112.00 60.00 27 18 \w 33.00 136.00 1.00 19.50 -- 94.50 -92.00 30.00 103 19 \w 107.00 133.00 1.00 19.50 -- 94.50 38.00 120.00 26 20 \w 93.00 136.00 1.00 19.50 -- 94.50 64.00 0.00 43 21 \w 78.00 105.00 1.00 19.50 -- 94.50 -92.00 120.00 27 22 \w 22.00 70.00 1.00 19.50 -- 94.50 -77.00 -30.00 48 23 \w 20.00 134.00 1.00 19.50 -- 94.50 -25.00 0.00 114 24 \w 22.00 106.00 1.00 19.50 -- 94.50 12.00 -30.00 84 25 \w 51.00 101.00 1.00 19.50 -- 94.50 -92.00 -60.00 50 26 \w 39.00 76.00 1.00 19.50 -- 94.50 -25.00-150.00 37 27 \w 72.00 99.00 1.00 19.50 -- 94.50 -92.00-150.00 27 28 \w 78.00 119.00 1.00 19.50 -- 94.50 50.00-150.00 41 29 \w 46.00 71.00 1.00 19.50 -- 94.50 -92.00-150.00 25 30 \w 76.00 119.00 1.00 19.50 -- 94.50 -50.00 30.00 43 31 \w 26.00 67.00 1.00 19.50 -- 94.50-112.00 90.00 41 32 \w 87.00 163.00 1.00 19.50 -- 94.50 38.00-180.00 76 33 \w 136.00 165.00 1.00 19.50 -- 94.50 64.00 90.00 29 34 \w 138.00 165.00 1.00 19.50 -- 94.50 50.00-120.00 27 35 \w 31.00 88.00 1.00 19.50 -- 94.50 -64.00-120.00 57 36 \w 60.00 85.00 1.00 19.50 -- 94.50 -64.00 -30.00 25 37 \w 29.00 56.00 1.00 19.50 -- 94.50 -92.00 60.00 27 38 \w 56.00 114.00 1.00 19.50 -- 94.50 -93.00-177.54 58 39 \w 102.00 128.00 1.00 15.00 -- 94.50 178.00 0.00 26 40 \w 72.00 98.00 1.00 15.00 -- 94.50 38.00 -60.00 26 41 \w 103.00 129.00 1.00 15.00 -- 94.50 38.00 -60.00 26 42 \w 103.00 128.00 1.00 15.00 -- 94.50 -77.00 30.00 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0389928000 _diffrn_orient_matrix_UB_12 0.0031686000 _diffrn_orient_matrix_UB_13 -0.0692793000 _diffrn_orient_matrix_UB_21 -0.1553737000 _diffrn_orient_matrix_UB_22 0.0742072000 _diffrn_orient_matrix_UB_23 -0.0032985000 _diffrn_orient_matrix_UB_31 0.2312183000 _diffrn_orient_matrix_UB_32 0.0493688000 _diffrn_orient_matrix_UB_33 0.0094528000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance Ultra (Cu) X-ray Source' _reflns_Friedel_coverage 0.695 _reflns_Friedel_fraction_full 0.864 _reflns_Friedel_fraction_max 0.998 _reflns_number_gt 3066 _reflns_number_total 3290 _reflns_odcompleteness_completeness 88.60 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (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)' _refine_diff_density_max 0.665 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.058 _refine_ls_abs_structure_details ; Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.027(15) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 3290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0420 _refine_ls_restrained_S_all 1.051 _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^)+(0.0636P)^2^+0.2954P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1114 _refine_ls_wR_factor_ref 0.1163 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C13(H13) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23) 2.c Idealised Me refined as rotating group: C24(H24A,H24B,H24C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 0.97588(15) 0.30358(5) 0.23386(3) 0.0837(3) Uani 1 1 d . . . . . S1 S 0.2154(3) 0.37543(7) 0.44604(5) 0.0422(3) Uani 1 1 d . . . . . O1 O 0.0327(8) 0.4265(2) 0.42396(17) 0.0526(9) Uani 1 1 d . . . . . O2 O 0.1543(7) 0.3046(2) 0.47542(16) 0.0502(9) Uani 1 1 d . . . . . O3 O 0.7997(11) 0.3690(2) 0.84603(18) 0.0710(13) Uani 1 1 d . . . . . N006 N 0.3745(8) 0.4263(2) 0.49701(18) 0.0435(10) Uani 1 1 d . . . . . C1 C 0.4249(11) 0.3555(3) 0.3878(2) 0.0440(12) Uani 1 1 d . . . . . C2 C 0.5874(12) 0.2950(3) 0.3944(2) 0.0518(13) Uani 1 1 d . . . . . H2 H 0.5843 0.2643 0.4291 0.062 Uiso 1 1 calc R . . . . C3 C 0.7555(12) 0.2806(3) 0.3485(3) 0.0585(15) Uani 1 1 d . . . . . H3 H 0.8697 0.2411 0.3525 0.070 Uiso 1 1 calc R . . . . C4 C 0.7506(12) 0.3251(4) 0.2979(3) 0.0564(15) Uani 1 1 d . . . . . C5 C 0.5900(15) 0.3846(4) 0.2903(3) 0.0675(18) Uani 1 1 d . . . . . H5 H 0.5906 0.4137 0.2547 0.081 Uiso 1 1 calc R . . . . C6 C 0.4267(13) 0.4009(4) 0.3363(2) 0.0578(15) Uani 1 1 d . . . . . H6 H 0.3188 0.4422 0.3326 0.069 Uiso 1 1 calc R . . . . C7 C 0.5486(10) 0.3949(3) 0.5358(2) 0.0412(11) Uani 1 1 d . . . . . H7 H 0.5724 0.3427 0.5442 0.049 Uiso 1 1 calc R . . . . C8 C 0.6768(10) 0.4550(3) 0.5587(2) 0.0392(10) Uani 1 1 d . . . . . C9 C 0.5807(10) 0.5249(2) 0.5339(2) 0.0390(11) Uani 1 1 d . . . . . C10 C 0.3974(10) 0.5073(3) 0.4947(2) 0.0425(11) Uani 1 1 d . . . . . H10 H 0.3064 0.5415 0.4712 0.051 Uiso 1 1 calc R . . . . C11 C 0.7191(10) 0.5902(3) 0.5588(2) 0.0404(11) Uani 1 1 d . . . . . C12 C 0.9005(9) 0.5604(3) 0.5967(2) 0.0399(11) Uani 1 1 d . . . . . C13 C 0.8847(10) 0.4717(3) 0.6014(2) 0.0406(11) Uani 1 1 d . . . . . H13 H 1.0344 0.4493 0.5846 0.049 Uiso 1 1 calc R . . . . C14 C 1.0644(11) 0.6090(3) 0.6246(2) 0.0493(12) Uani 1 1 d . . . . . H14 H 1.1874 0.5890 0.6492 0.059 Uiso 1 1 calc R . . . . C15 C 1.0449(12) 0.6880(3) 0.6159(3) 0.0543(13) Uani 1 1 d . . . . . H15 H 1.1543 0.7213 0.6348 0.065 Uiso 1 1 calc R . . . . C16 C 0.8643(11) 0.7175(3) 0.5792(2) 0.0510(14) Uani 1 1 d . . . . . H16 H 0.8543 0.7708 0.5736 0.061 Uiso 1 1 calc R . . . . C17 C 0.6981(12) 0.6701(3) 0.5507(2) 0.0457(12) Uani 1 1 d . . . . . H17 H 0.5748 0.6908 0.5266 0.055 Uiso 1 1 calc R . . . . C18 C 0.8539(10) 0.4431(2) 0.6667(2) 0.0388(11) Uani 1 1 d . . . . . C19 C 1.0269(14) 0.3995(4) 0.6936(3) 0.0706(18) Uani 1 1 d . . . . . H19 H 1.1638 0.3848 0.6714 0.085 Uiso 1 1 calc R . . . . C20 C 1.0051(17) 0.3759(4) 0.7543(3) 0.079(2) Uani 1 1 d . . . . . H20 H 1.1285 0.3468 0.7722 0.095 Uiso 1 1 calc R . . . . C21 C 0.8063(13) 0.3952(3) 0.7867(2) 0.0499(13) Uani 1 1 d . . . . . C22 C 0.6291(13) 0.4382(4) 0.7608(3) 0.0642(17) Uani 1 1 d . . . . . H22 H 0.4910 0.4519 0.7829 0.077 Uiso 1 1 calc R . . . . C23 C 0.6552(13) 0.4621(4) 0.7000(3) 0.0641(17) Uani 1 1 d . . . . . H23 H 0.5326 0.4918 0.6823 0.077 Uiso 1 1 calc R . . . . C24 C 0.6060(18) 0.3917(4) 0.8828(3) 0.083(3) Uani 1 1 d . . . . . H24A H 0.4553 0.3740 0.8655 0.125 Uiso 1 1 calc GR . . . . H24B H 0.6034 0.4472 0.8858 0.125 Uiso 1 1 calc GR . . . . H24C H 0.6257 0.3698 0.9226 0.125 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 0.0763(5) 0.1143(6) 0.0603(4) -0.0260(4) 0.0219(4) -0.0266(5) S1 0.0545(7) 0.0386(5) 0.0336(6) 0.0000(4) -0.0029(5) -0.0076(5) O1 0.058(2) 0.0503(18) 0.0496(19) -0.0003(15) -0.0082(19) -0.0002(18) O2 0.062(2) 0.0455(18) 0.0428(18) 0.0029(15) -0.0004(17) -0.0151(18) O3 0.115(4) 0.058(2) 0.040(2) 0.0114(17) 0.002(2) 0.020(3) N006 0.060(3) 0.0362(19) 0.034(2) -0.0010(16) -0.004(2) -0.0005(18) C1 0.061(3) 0.039(2) 0.031(2) -0.0007(18) -0.004(2) -0.013(2) C2 0.074(4) 0.046(3) 0.035(2) -0.001(2) -0.002(3) -0.002(3) C3 0.065(4) 0.057(3) 0.053(3) -0.013(3) -0.003(3) 0.000(3) C4 0.057(4) 0.070(3) 0.042(3) -0.010(3) 0.003(3) -0.016(3) C5 0.088(5) 0.081(4) 0.033(3) 0.009(3) 0.009(3) -0.012(4) C6 0.075(4) 0.058(3) 0.041(3) 0.008(2) -0.006(3) 0.005(3) C7 0.056(3) 0.039(2) 0.029(2) 0.0003(18) 0.002(2) 0.002(2) C8 0.054(3) 0.034(2) 0.029(2) -0.0044(17) 0.004(2) 0.003(2) C9 0.054(3) 0.033(2) 0.030(2) 0.0006(17) 0.005(2) -0.002(2) C10 0.057(3) 0.037(2) 0.033(2) 0.0010(19) -0.005(2) 0.004(2) C11 0.053(3) 0.037(2) 0.031(2) -0.0019(18) 0.008(2) -0.002(2) C12 0.048(3) 0.042(2) 0.030(2) -0.0015(18) 0.005(2) -0.005(2) C13 0.048(3) 0.037(2) 0.037(2) -0.0044(19) 0.004(2) 0.004(2) C14 0.051(3) 0.051(3) 0.046(3) 0.001(2) -0.001(2) -0.007(3) C15 0.063(3) 0.050(3) 0.050(3) -0.002(2) -0.002(3) -0.019(3) C16 0.073(4) 0.035(2) 0.045(3) 0.000(2) 0.010(3) -0.006(2) C17 0.063(3) 0.040(2) 0.034(2) 0.0003(19) 0.006(2) -0.002(2) C18 0.052(3) 0.030(2) 0.034(2) -0.0048(17) 0.000(2) 0.003(2) C19 0.076(4) 0.075(4) 0.061(3) 0.016(3) 0.012(3) 0.039(4) C20 0.097(5) 0.082(4) 0.058(3) 0.029(3) -0.001(4) 0.036(4) C21 0.081(4) 0.035(2) 0.034(2) 0.0014(19) -0.001(3) 0.010(3) C22 0.074(4) 0.074(4) 0.045(3) 0.013(3) 0.016(3) 0.029(3) C23 0.068(4) 0.079(4) 0.045(3) 0.013(3) 0.007(3) 0.033(3) C24 0.136(7) 0.078(4) 0.036(3) 0.007(3) 0.013(4) 0.021(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C4 1.910(6) . ? S1 O1 1.420(4) . ? S1 O2 1.424(4) . ? S1 N006 1.670(4) . ? S1 C1 1.755(6) . ? O3 C21 1.382(6) . ? O3 C24 1.392(10) . ? N006 C7 1.389(7) . ? N006 C10 1.406(6) . ? C1 C2 1.380(8) . ? C1 C6 1.379(8) . ? C2 C3 1.389(9) . ? C3 C4 1.352(9) . ? C4 C5 1.364(10) . ? C5 C6 1.380(9) . ? C7 C8 1.351(7) . ? C8 C9 1.426(7) . ? C8 C13 1.504(8) . ? C9 C10 1.358(8) . ? C9 C11 1.465(7) . ? C11 C12 1.396(8) . ? C11 C17 1.398(7) . ? C12 C13 1.539(6) . ? C12 C14 1.374(8) . ? C13 C18 1.528(7) . ? C14 C15 1.382(8) . ? C15 C16 1.374(9) . ? C16 C17 1.376(8) . ? C18 C19 1.347(8) . ? C18 C23 1.353(8) . ? C19 C20 1.403(9) . ? C20 C21 1.344(10) . ? C21 C22 1.348(9) . ? C22 C23 1.409(8) . ? 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 121.6(3) . . ? O1 S1 N006 105.7(2) . . ? O1 S1 C1 109.4(2) . . ? O2 S1 N006 105.6(2) . . ? O2 S1 C1 108.5(2) . . ? N006 S1 C1 104.6(2) . . ? C21 O3 C24 118.5(5) . . ? C7 N006 S1 124.5(3) . . ? C7 N006 C10 110.4(4) . . ? C10 N006 S1 123.1(3) . . ? C2 C1 S1 119.5(4) . . ? C6 C1 S1 119.5(5) . . ? C6 C1 C2 120.9(5) . . ? C1 C2 C3 119.0(5) . . ? C4 C3 C2 119.0(6) . . ? C3 C4 Br1 119.0(5) . . ? C3 C4 C5 122.8(6) . . ? C5 C4 Br1 118.2(4) . . ? C4 C5 C6 118.8(5) . . ? C1 C6 C5 119.4(6) . . ? C8 C7 N006 106.7(4) . . ? C7 C8 C9 108.3(5) . . ? C7 C8 C13 140.7(4) . . ? C9 C8 C13 111.0(4) . . ? C8 C9 C11 108.5(4) . . ? C10 C9 C8 109.1(4) . . ? C10 C9 C11 142.4(5) . . ? C9 C10 N006 105.4(4) . . ? C12 C11 C9 108.0(4) . . ? C12 C11 C17 119.9(5) . . ? C17 C11 C9 132.1(5) . . ? C11 C12 C13 111.5(4) . . ? C14 C12 C11 120.5(4) . . ? C14 C12 C13 128.0(5) . . ? C8 C13 C12 101.0(4) . . ? C8 C13 C18 116.2(4) . . ? C18 C13 C12 113.0(4) . . ? C12 C14 C15 119.3(6) . . ? C16 C15 C14 120.3(5) . . ? C15 C16 C17 121.5(5) . . ? C16 C17 C11 118.4(5) . . ? C19 C18 C13 121.0(5) . . ? C19 C18 C23 117.6(5) . . ? C23 C18 C13 121.3(5) . . ? C18 C19 C20 121.4(6) . . ? C21 C20 C19 120.1(6) . . ? C20 C21 O3 116.1(6) . . ? C20 C21 C22 119.8(5) . . ? C22 C21 O3 124.1(6) . . ? C21 C22 C23 119.4(6) . . ? C18 C23 C22 121.7(6) . . ? _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 1.964 _oxdiff_exptl_absorpt_empirical_full_min 0.490