#------------------------------------------------------------------------------ #$Date: 2020-12-05 07:25:49 +0200 (Sat, 05 Dec 2020) $ #$Revision: 259552 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022289.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2022289 loop_ _publ_author_name 'Rosiak, Damian' 'Okuniewski, Andrzej' 'Chojnacki, Jaros\/law' _publ_section_title ; The influence of the type of halogen substituent and its position on the molecular conformation, intermolecular interactions and crystal packing for a series of 1-benzoyl-3-(halogenophenyl)thioureas ; _journal_coeditor_code WP3011 _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first ; ; _journal_paper_doi 10.1107/S2053229620015594 _journal_volume 77 _journal_year 2021 _chemical_formula_iupac 'C14 H11 Br N2 O S' _chemical_formula_moiety 'C14 H11 Br N2 O S' _chemical_formula_sum 'C14 H11 Br N2 O S' _chemical_formula_weight 335.23 _chemical_name_common 1-Benzoyl-3-o-bromophenylthiourea _chemical_name_systematic ; 1-Benzoyl-3-(2-bromophenyl)thiourea ; _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_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 95.183(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.9592(4) _cell_length_b 15.142(2) _cell_length_c 22.250(2) _cell_measurement_reflns_used 7760 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.66 _cell_measurement_theta_min 2.69 _cell_volume 1328.4(3) _computing_cell_refinement ; X-AREA (Stoe & Cie, 2009) ; _computing_data_collection ; X-AREA (Stoe & Cie, 2009) ; _computing_data_reduction ; X-RED32 (Stoe & Cie, 2009) ; _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL2018 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 120 _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'Stoe IPDS 2T' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_radiation_monochromator 'parabolic x-ray mirror' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_unetI/netI 0.0541 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 7908 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.996 _diffrn_reflns_theta_min 2.690 _diffrn_source 'GeniX Mo, 0.05 x 0.05 mm2 microfocus' _diffrn_source_current 1.000 _diffrn_source_power 0.050 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 3.243 _exptl_absorpt_correction_T_max 0.8920 _exptl_absorpt_correction_T_min 0.3786 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; [X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.676 _exptl_crystal_description needle _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.034 _refine_diff_density_max 1.061 _refine_diff_density_min -1.475 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 3530 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0492 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.6126P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1270 _refine_ls_wR_factor_ref 0.1450 _reflns_number_gt 2917 _reflns_number_total 3566 _reflns_threshold_expression I>=2u(I) _cod_data_source_file wp3011sup1.cif _cod_data_source_block 4 _cod_database_code 2022289 _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_min 0.192 _shelx_estimated_absorpt_t_max 0.898 _shelx_hkl_file ; -4 4 -2 170.54 15.24 -4 4 -1 54.76 15.48 -4 4 0 120.28 16.29 -4 4 6 25.58 18.62 -4 4 7 2.98 18.62 -4 5 -6 9.85 17.35 -4 5 12 9.67 25.95 -4 6 -9 7.61 11.92 -4 7 -12 -1.53 18.02 -3 2 -3 147.17 19.29 -3 3 -8 182.41 20.36 -3 3 13 25.71 22.13 -3 4 -11 114.56 13.57 -3 5 -14 38.16 16.79 -3 7 -17 2.57 11.54 -3 8 -19 49.85 15.76 -2 1 -6 1090.58 22.80 -2 2 -10 336.03 17.64 -2 3 -13 64.13 18.06 -2 7 24 9.68 42.34 -1 0 -3 652.73 30.48 -1 1 -9 1370.21 28.80 -1 3 -15 19.94 16.35 -1 5 -19 54.71 19.71 -1 7 -22 24.16 20.77 -1 9 27 24.04 28.60 0 2 14 46.22 19.86 0 4 19 5.99 20.07 0 8 25 347.73 28.41 0 9 26 9.56 27.37 1 1 4 3097.57 43.49 1 2 10 60.12 18.92 1 4 16 173.79 18.57 1 6 20 508.86 24.99 1 8 23 -0.22 20.55 1 9 24 59.09 27.86 3 6 6 366.58 20.99 3 10 16 20.91 17.75 4 10 -3 6.89 23.95 4 10 -2 -2.24 21.97 4 10 -1 8.79 22.23 4 10 0 267.67 24.49 4 10 2 141.45 21.18 4 10 3 39.78 17.62 4 11 -8 316.37 26.06 4 11 6 -0.72 21.38 4 12 -11 10.75 22.61 -5 7 1 -3.27 19.01 -5 7 4 5.87 20.97 -5 7 5 0.28 21.68 -4 4 -3 18.02 15.63 -4 5 -8 -24.78 17.67 -4 5 -7 15.06 11.80 -3 2 -5 25.02 19.79 -3 2 -4 462.70 17.76 -3 2 9 61.02 19.40 -3 3 -9 162.77 23.50 -3 4 -12 483.49 21.50 -3 6 -16 17.63 12.54 -2 1 10 16.16 24.64 -2 2 14 14.28 34.24 -2 4 -16 1067.54 23.93 -2 5 -18 21.06 18.81 -2 8 -22 7.86 19.21 -1 2 -13 84.55 18.49 0 1 -9 284.86 29.13 0 1 10 590.66 27.42 0 6 22 363.14 23.65 1 1 2 775.70 31.03 1 1 3 2295.32 40.67 1 3 13 351.96 21.96 1 5 18 43.32 15.86 1 7 21 13.41 22.73 2 3 4 44.09 18.16 2 6 15 117.27 18.48 2 7 17 1.74 13.67 2 11 22 119.88 28.37 3 6 4 40.66 18.45 3 6 5 195.37 14.88 3 7 9 21.07 14.32 3 8 11 5.44 20.55 3 9 -15 0.04 26.00 3 9 13 4.39 21.77 3 11 16 -5.26 26.91 4 11 -7 3.30 24.67 4 11 3 -5.71 24.88 4 12 7 46.21 23.57 -4 4 -5 205.94 18.38 -4 4 -4 32.20 16.04 -4 5 -9 16.10 16.49 -3 2 -6 280.68 20.45 -3 3 -10 73.99 20.36 -3 4 -13 522.69 21.32 -3 5 -15 12.29 17.11 -3 6 -17 83.68 16.93 -3 8 -20 23.66 18.36 -2 1 -7 135.71 12.16 -2 2 -11 428.46 14.29 -2 3 -14 36.85 16.89 -1 0 -4 0.87 15.71 -1 0 6 -2.24 29.50 -1 1 -10 1139.03 26.66 -1 3 -16 26.41 16.47 -1 4 -18 47.75 17.57 -1 5 -20 6.12 17.61 -1 8 -24 256.23 24.06 0 2 -13 181.63 22.94 0 3 16 121.34 20.39 0 4 -18 306.10 24.97 0 5 20 28.56 20.93 0 8 -24 126.66 23.17 0 9 -25 33.42 24.06 0 10 -26 200.17 26.89 1 1 0 3597.75 53.88 1 1 1 3464.66 53.42 1 2 9 41.49 19.73 1 4 15 171.88 19.67 1 5 -18 10.30 23.81 1 6 19 620.83 25.17 1 8 22 293.22 24.39 1 9 23 31.59 25.40 2 3 2 86.19 19.18 2 3 3 154.96 18.73 2 4 -10 845.68 32.55 2 5 12 -0.60 13.10 2 6 14 105.54 19.92 2 7 16 87.40 19.91 2 8 18 15.21 15.59 3 6 -5 113.45 20.33 3 6 1 24.44 18.31 3 6 2 225.38 19.47 3 6 3 -13.02 13.75 3 7 -10 2.64 20.03 3 7 7 80.82 21.19 3 7 8 4.33 14.73 3 10 14 6.60 23.64 4 11 -3 16.29 24.68 4 11 -2 109.43 24.83 4 11 -1 5.40 23.10 4 12 -9 -10.81 24.87 4 12 4 37.00 25.32 4 12 5 -0.68 26.04 -4 3 0 -3.48 17.85 -4 3 1 810.09 23.06 -4 4 -6 93.90 17.23 -4 5 -10 113.33 17.36 -4 5 14 -1.96 30.02 -4 6 -12 102.83 13.85 -4 7 -14 70.13 14.66 -3 2 -7 22.45 19.47 -3 2 10 166.73 22.33 -3 3 -11 30.09 19.67 -3 5 -16 -3.97 15.96 -3 7 -19 -11.65 17.80 -2 0 0 725.46 23.46 -2 0 1 -13.32 17.97 -2 0 2 550.34 22.27 -2 1 -8 224.27 12.50 -2 2 -12 167.54 15.99 -2 3 -15 -2.11 16.03 -2 4 -17 106.21 17.51 -2 5 -19 9.87 19.34 -2 8 -23 229.80 23.41 -1 0 -5 918.27 28.48 -1 3 17 5.49 24.35 -1 5 21 59.06 24.23 -1 7 -23 27.78 22.23 -1 7 24 3.51 25.29 -1 8 25 47.79 29.44 0 2 13 184.12 21.19 0 3 -16 94.34 25.58 0 4 18 328.79 23.85 0 5 -20 25.12 18.88 0 7 -23 -5.07 21.18 0 8 24 156.42 25.11 1 2 8 939.57 27.59 1 3 12 800.59 24.16 1 4 -16 221.87 30.65 1 5 17 75.16 13.47 1 6 -20 1.70 29.02 1 9 -24 222.07 32.53 1 10 -25 50.11 33.01 2 3 -3 991.83 27.99 2 3 -1 1925.95 33.33 2 3 0 468.22 22.80 2 3 1 1355.11 28.00 2 5 -13 12.43 25.58 2 8 17 666.61 23.26 3 6 -3 6.56 12.44 3 6 -2 183.59 17.58 3 6 -1 63.26 16.77 3 7 6 523.08 21.98 3 8 -12 277.55 27.87 3 8 9 31.81 20.34 3 9 11 0.57 21.64 3 11 15 114.22 19.09 3 12 16 186.29 24.58 4 12 -7 44.23 26.73 4 13 5 109.22 28.21 -5 6 -2 17.81 17.99 -5 6 0 26.59 18.82 -5 6 3 14.54 15.04 -5 6 4 2.88 20.95 -4 3 -3 86.26 15.70 -4 3 -2 14.86 17.02 -4 3 -1 233.84 14.72 -4 4 -8 73.62 17.53 -4 4 -7 195.49 13.92 -4 5 -11 14.07 16.93 -4 6 -13 44.33 13.75 -4 6 17 19.30 36.49 -3 1 -2 381.61 18.33 -3 1 1 391.52 14.56 -3 1 3 564.22 18.97 -3 2 -8 609.87 22.89 -3 3 -12 296.55 19.84 -3 4 -14 457.31 17.97 -3 6 -18 3.09 13.04 -3 7 -20 209.43 16.94 -2 0 -2 45.19 17.52 -2 0 -1 -6.14 12.26 -2 0 3 -2.88 15.75 -2 0 4 18.65 16.96 -2 1 -9 612.67 18.78 -2 6 -21 18.50 21.51 -1 0 -6 -10.97 20.31 -1 1 -11 893.29 24.24 -1 2 -14 152.12 14.03 -1 4 -19 222.08 18.14 -1 4 19 49.14 21.64 -1 6 -22 130.44 20.37 -1 9 26 7.20 27.50 0 6 -22 346.46 25.75 0 6 21 171.27 20.64 1 4 14 215.66 19.81 1 8 -23 21.01 27.81 1 11 24 15.30 26.52 2 7 15 32.98 18.04 2 9 18 12.44 21.86 2 11 20 31.39 25.22 3 7 4 621.63 21.76 3 9 -14 22.67 23.46 3 9 10 -8.60 20.49 4 12 1 42.78 18.54 4 13 -9 126.59 25.21 4 13 4 23.86 23.23 -5 6 7 5.12 19.97 -5 6 8 10.83 20.31 -4 3 -5 118.61 17.31 -4 3 -4 56.22 17.93 -4 3 8 54.83 25.58 -4 4 -9 19.64 17.57 -4 4 12 192.28 27.02 -4 7 19 31.42 38.96 -3 1 -4 17.29 15.44 -3 1 -3 477.62 18.58 -3 1 6 36.98 13.54 -3 2 -9 271.13 21.87 -3 4 -15 121.24 20.10 -3 6 -19 58.25 17.88 -2 0 -4 525.65 19.57 -2 0 -3 -5.26 11.27 -2 0 5 0.71 16.35 -2 1 -10 136.59 15.41 -2 2 -13 324.63 14.19 -2 3 -16 10.57 16.54 -2 4 -18 276.02 19.71 -2 5 -20 16.05 18.67 -2 7 -23 262.96 20.78 -2 8 -24 16.45 22.69 -1 1 11 1181.13 57.20 -1 3 -17 -0.86 16.81 -1 5 -21 9.14 19.63 -1 7 -24 16.12 18.76 -1 8 -25 7.75 22.38 -1 9 -26 29.48 25.85 0 1 -10 586.30 26.36 0 3 15 1328.87 30.18 0 5 19 11.07 23.49 0 7 22 9.19 21.77 1 2 7 143.47 20.91 1 3 11 -2.24 18.49 1 5 16 5.19 16.31 1 9 22 17.67 16.90 1 10 23 112.16 19.39 2 4 -9 334.00 25.58 2 6 12 288.47 18.40 3 7 2 260.13 19.81 3 7 3 137.78 18.82 3 8 -11 70.91 21.15 3 11 -17 70.09 28.00 3 12 14 71.31 24.91 4 13 -7 332.89 26.35 4 13 -6 38.53 25.78 4 13 -4 19.54 27.44 4 13 0 11.31 23.75 4 13 1 101.01 27.24 -5 5 1 34.43 16.93 -5 5 3 39.65 17.31 -5 6 9 12.83 20.28 -4 3 -6 -11.10 18.47 -4 3 9 194.63 27.13 -4 4 -10 84.51 17.25 -4 6 -15 -0.26 18.32 -3 1 -5 349.63 17.89 -3 2 -10 453.73 21.87 -3 3 -13 89.32 14.87 -3 4 -16 24.02 18.04 -3 5 -18 0.59 16.69 -2 0 -5 6.95 15.64 -2 1 11 36.92 24.60 -2 2 -14 170.21 16.44 -2 6 22 29.51 29.51 -1 0 -7 20.22 14.33 -1 1 -12 76.17 17.23 -1 2 -15 20.62 16.45 -1 6 -23 271.40 20.87 -1 6 22 116.20 22.32 0 2 -14 47.02 17.82 0 2 12 187.18 19.72 0 4 -19 14.81 19.48 0 4 17 -0.46 18.87 0 8 -25 429.18 24.80 0 8 23 390.07 25.03 0 9 24 11.02 23.42 0 10 25 12.47 27.67 1 4 13 240.28 20.53 2 9 17 2.69 16.20 2 12 20 28.74 24.87 3 7 -6 371.78 20.35 3 7 -4 117.43 19.44 3 7 -2 436.28 20.30 3 7 -1 389.66 20.06 3 7 0 1022.78 23.34 3 7 1 244.78 19.17 3 8 -10 459.77 25.29 3 8 5 99.48 18.39 3 9 -13 28.01 24.93 3 10 10 24.06 21.46 3 11 12 -4.12 22.50 4 13 -3 210.77 20.67 4 13 -2 2.45 18.55 -5 5 -2 15.82 19.12 -5 5 -1 6.45 14.45 -5 5 6 1.58 17.12 -4 2 0 21.84 20.59 -4 3 -8 15.92 18.28 -4 3 -7 1.90 13.66 -4 4 -11 54.37 17.45 -4 4 13 36.02 23.97 -4 5 -14 25.47 17.41 -4 6 -16 24.96 18.47 -3 1 -7 106.39 16.41 -3 1 -6 16.73 11.51 -3 2 -11 206.83 19.73 -3 2 12 1336.12 36.78 -3 3 -14 82.73 20.27 -3 6 -20 77.64 19.39 -2 0 -6 19.32 11.27 -2 0 6 761.04 26.40 -2 1 -11 129.09 11.64 -2 3 -17 -4.11 16.03 -2 4 -19 325.86 19.30 -2 5 -21 32.31 18.97 -2 7 -24 5.71 20.23 -1 0 -8 -13.99 18.28 -1 2 14 76.82 24.38 -1 3 -18 -5.27 16.24 -1 4 -20 525.73 21.24 -1 7 23 21.97 24.49 -1 10 26 -6.48 30.71 0 1 8 2175.97 45.64 0 3 -17 109.04 19.26 0 5 -21 10.69 18.24 0 6 20 189.70 20.04 0 7 -24 12.95 20.40 1 2 6 4.16 12.56 1 3 10 291.09 18.53 1 5 15 575.65 21.35 1 6 17 419.30 17.46 1 7 -22 274.41 30.37 1 10 22 -10.82 19.90 1 11 23 18.48 19.35 2 4 -8 1041.82 29.26 2 4 3 6.78 16.84 2 4 4 38.08 12.08 2 7 13 83.78 16.98 2 8 -19 3.80 33.52 2 9 16 11.08 20.64 3 10 9 215.68 21.44 3 11 11 8.13 21.84 4 14 -3 7.13 23.31 -5 5 -6 11.93 16.88 -5 5 -5 2.96 18.81 -5 5 -4 3.05 13.62 -4 2 -3 314.77 21.48 -4 3 -9 -13.12 18.56 -4 3 10 96.91 23.71 -4 5 16 7.47 28.88 -4 6 18 109.86 38.81 -3 1 -8 365.61 18.36 -3 2 -12 311.53 19.69 -3 3 -15 26.13 20.65 -3 4 -17 148.61 14.65 -2 0 -7 0.70 10.45 -2 1 -12 482.27 17.55 -2 2 -15 208.58 13.28 -2 6 -23 9.45 20.87 -1 2 -16 1456.37 24.65 -1 5 -22 6.92 18.91 -1 5 20 180.61 22.81 -1 7 -25 39.32 20.93 -1 8 -26 56.26 23.53 -1 8 24 343.48 25.91 -1 9 25 13.34 24.29 0 0 -3 -1.67 26.86 0 1 -11 1068.24 30.74 0 3 14 251.52 22.89 0 5 18 451.01 25.95 0 6 -23 12.18 24.35 1 2 5 124.38 19.40 1 4 12 7.72 17.49 1 12 23 137.36 27.17 2 4 2 127.32 18.00 2 5 -12 805.37 31.33 2 7 12 172.92 19.87 2 10 17 60.13 16.30 2 12 19 73.95 18.02 3 9 -12 7.97 19.93 3 10 8 -12.06 19.91 3 11 -16 77.50 27.57 -5 4 2 4.45 15.82 -5 5 9 80.04 30.13 -4 2 -6 45.57 20.15 -4 3 -10 19.08 18.21 -4 4 -13 144.18 14.40 -4 4 14 70.19 27.21 -4 5 -16 222.12 17.40 -3 0 -1 36.15 13.49 -3 0 0 6.49 13.19 -3 0 1 84.33 14.44 -3 1 -9 94.00 17.27 -3 2 -13 -5.76 19.39 -3 3 -16 72.72 17.26 -3 4 -18 44.08 19.48 -3 5 -20 -8.06 18.68 -2 0 -8 722.33 16.27 -2 0 7 3.42 16.41 -2 1 -13 113.18 15.16 -2 2 -16 177.31 17.07 -2 3 -18 17.43 12.63 -2 4 -20 80.77 13.66 -2 5 -22 6.55 19.88 -2 7 23 92.77 30.21 -1 0 -9 566.81 18.50 -1 3 -19 84.24 17.58 -1 4 -21 136.11 18.41 -1 4 18 10.03 21.99 -1 6 -24 55.39 21.45 0 0 -4 3393.87 70.94 0 2 -15 41.99 17.86 0 4 16 50.76 19.05 0 8 22 19.61 21.01 0 9 23 107.48 23.26 0 10 24 52.41 23.62 1 3 9 90.59 13.78 1 5 14 61.56 17.23 1 6 16 85.82 12.91 1 10 21 504.64 26.05 2 4 0 37.10 17.53 2 4 1 4.74 16.58 2 12 18 121.72 21.89 3 8 -7 -4.07 18.43 3 8 -6 684.14 23.61 3 8 -1 5.02 17.71 3 8 0 63.27 18.46 3 8 1 141.49 17.18 3 9 -11 -5.67 23.03 3 9 5 62.05 16.94 3 10 -14 184.68 22.24 3 11 9 55.46 21.05 3 12 -17 269.13 32.23 3 12 11 203.11 17.26 3 14 13 19.11 18.57 -5 4 -4 18.03 18.08 -5 4 -3 59.44 18.35 -5 4 -2 10.45 14.27 -5 4 3 -4.57 13.50 -5 4 4 22.35 19.51 -5 4 5 5.50 19.49 -5 5 10 19.83 28.77 -4 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1394.88 7.37 1 -5 -1 1117.88 7.54 1 6 -18 78.93 6.03 2 -18 -10 9.29 3.78 2 -17 -9 17.29 3.51 2 -16 -8 197.54 4.07 2 -14 -7 931.62 5.86 2 -11 -6 90.06 3.50 2 -10 -6 591.63 5.02 2 -9 -6 155.17 3.65 2 -6 -7 250.91 4.04 2 0 -13 -1.17 3.95 2 2 -18 62.16 4.68 3 -12 -19 11.06 3.85 3 -11 -19 117.04 4.11 3 -11 -18 54.47 3.52 3 -10 -19 10.38 3.57 3 -10 -18 8.41 3.11 3 -9 -19 5.30 3.34 3 -8 -20 14.74 3.68 3 -8 -19 2.21 3.51 3 -7 -21 32.90 4.00 3 -7 -20 136.16 4.25 3 -6 -25 9.59 3.95 3 -6 -24 3.81 3.86 3 -6 -23 6.94 3.63 3 -6 -22 2.27 3.87 3 -6 -21 0.46 3.26 -5 -5 5 162.95 5.02 -5 -3 4 136.79 4.44 -5 3 -2 6.33 3.45 -5 5 -5 3.41 2.53 -4 -10 8 33.71 5.95 -4 -9 8 56.31 5.23 -4 -5 7 53.47 4.50 -4 -3 6 18.57 3.61 -4 0 4 10.59 3.42 -4 1 3 99.92 3.88 -4 2 2 68.32 3.43 -4 5 -2 581.23 4.82 -4 6 -4 121.08 3.55 -4 7 -6 14.35 2.90 -4 8 -9 249.60 3.92 -4 9 -13 11.20 3.39 -4 9 -12 4.67 2.39 -3 -6 8 352.87 7.10 -3 1 4 350.56 4.22 -3 2 3 22.22 2.39 -3 8 -7 70.40 3.29 -3 10 -14 17.22 3.26 -3 10 -13 284.74 3.33 -2 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43.42 2.80 -5 5 -6 17.88 2.65 -4 4 -1 68.39 3.02 -4 5 -3 -5.49 3.30 -4 7 -7 13.60 3.24 -4 8 -10 39.04 3.44 -3 -2 6 279.81 5.29 -3 4 0 186.12 3.67 -3 7 -5 301.79 3.90 -3 9 -11 4.53 2.96 -3 10 -16 18.98 3.47 -3 10 -15 58.73 3.08 -2 -1 5 27.69 3.81 -2 4 0 47.06 2.69 -2 9 -11 17.20 2.93 -2 10 -15 36.15 3.05 -1 -20 4 74.10 4.90 -1 -13 7 36.06 4.15 -1 -9 7 115.10 4.85 -1 -5 6 2.61 6.53 -1 6 -5 7.77 2.61 -1 8 -10 88.62 3.54 -1 10 -25 40.35 3.33 -1 10 -24 16.61 3.27 0 -17 3 103.79 4.09 0 -15 4 107.48 3.84 0 5 -7 134.81 4.41 0 8 -16 108.27 5.02 1 -20 -3 84.08 4.05 1 -17 -1 -3.95 3.30 1 -11 1 310.20 4.16 1 -6 0 1303.97 8.03 2 -17 -7 55.70 3.52 2 -15 -6 41.55 3.50 2 -13 -5 79.02 3.31 2 -11 -5 11.89 3.33 2 -10 -5 117.55 3.76 2 -9 -5 7.69 3.06 2 -6 -6 523.14 5.11 2 3 -24 0.53 5.38 2 3 -23 486.36 9.82 3 -13 -17 5.47 2.75 3 -12 -16 33.20 3.73 3 -10 -16 -0.80 3.42 3 -9 -16 24.93 3.66 3 -8 -17 176.66 3.40 3 -8 -16 55.43 3.37 3 -7 -17 -0.71 3.54 3 -6 -19 180.63 4.35 3 -6 -18 50.62 3.34 3 -5 -21 129.14 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20.15 4.51 -4 0 -8 124.48 4.77 -4 1 -11 186.58 5.09 -4 2 -18 8.62 4.92 -4 2 -17 18.32 4.47 -4 2 -16 45.43 3.84 -3 -5 4 35.74 5.15 -3 -4 3 36.02 4.67 -3 -3 2 786.70 7.54 -3 4 -15 127.28 4.33 -2 0 0 872.27 8.64 -2 5 -14 0.16 3.84 -2 5 -13 11.48 2.71 -1 -16 10 4.82 7.27 -1 6 -25 34.80 4.48 -1 6 -24 65.79 4.70 -1 6 -18 3.52 3.98 -1 6 -17 402.67 5.67 0 -12 9 80.68 5.31 0 -9 8 632.74 8.42 0 -7 7 854.96 10.66 0 6 -24 362.71 6.25 0 6 -23 15.03 4.36 0 6 -22 357.17 6.37 0 6 -21 159.05 5.23 0 6 -20 189.28 5.40 1 -19 7 14.61 5.73 1 -11 7 314.68 5.51 1 -7 5 232.56 4.69 1 5 -26 7.95 5.08 2 -11 4 515.43 6.40 2 -9 3 1448.67 8.06 2 -7 2 79.12 4.37 2 -6 1 22.39 3.00 2 -3 -2 302.43 4.98 3 -17 0 95.30 5.83 3 -16 0 114.43 5.90 3 -15 0 17.37 3.89 3 -14 0 1.46 5.24 3 -13 0 558.91 6.71 3 -10 -1 6.71 4.52 3 -7 -3 56.03 4.65 3 -6 -4 13.04 4.10 3 -5 -5 629.47 6.76 3 -3 -8 16.21 4.08 3 0 -15 436.38 7.89 4 -13 -7 352.35 7.20 4 -11 -8 308.88 6.13 4 -10 -9 4.89 3.86 4 -7 -12 17.57 5.32 4 -6 -13 72.19 5.13 4 -5 -16 1.87 5.37 4 -5 -15 36.19 4.86 4 -4 -19 56.79 5.99 -5 -6 -5 168.33 5.11 -4 -10 4 1.67 5.18 -4 -7 2 341.76 6.72 -4 -6 1 123.77 5.36 -4 -5 0 466.31 6.93 -4 -2 -4 122.49 4.34 -4 0 -9 -5.06 4.72 -4 1 -13 9.79 4.60 -4 1 -12 35.11 3.47 -3 0 -3 8.66 4.14 -3 3 -11 44.26 3.96 -3 4 -22 8.06 3.21 -3 4 -20 48.04 3.90 -3 4 -19 17.42 3.86 -3 4 -18 53.93 3.31 -3 4 -17 141.51 3.81 -2 1 -2 210.23 5.51 -2 2 -4 312.98 5.41 -2 4 -10 709.55 6.35 -2 5 -26 82.29 4.90 -2 5 -25 58.64 4.93 -2 5 -15 55.74 4.21 -1 1 -1 3426.06 18.57 -1 3 -5 2.54 3.23 -1 4 -8 280.10 5.76 -1 6 -23 260.94 5.28 -1 6 -21 289.47 5.46 -1 6 -20 544.47 6.40 1 -16 8 23.28 4.82 1 -8 6 140.94 4.85 2 -16 5 38.44 5.06 2 -15 5 63.86 5.13 2 -10 4 565.60 6.50 2 -8 3 529.19 6.30 3 -12 0 33.56 3.91 3 -11 0 15.72 4.69 3 -8 -2 55.18 3.49 3 -4 -6 79.02 4.70 4 -13 -6 27.76 5.07 4 -12 -7 48.02 4.39 4 -11 -7 3.71 5.41 4 -10 -8 39.41 4.96 4 -9 -9 60.74 4.02 4 -8 -10 2.26 3.51 4 -7 -11 121.65 5.78 4 -6 -12 486.37 6.85 4 -5 -14 6.70 4.88 4 -4 -18 326.96 6.92 -4 1 -14 196.85 4.41 -2 5 -16 32.57 2.85 -1 2 -3 1831.97 12.82 1 -4 3 639.87 7.50 2 -18 5 51.63 4.27 3 -17 1 45.87 4.24 3 -16 1 45.48 4.47 3 -15 1 618.27 6.75 3 -14 1 9.62 4.05 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 8728 _shelx_res_file ; TITL g72_a.res in P2(1)/n g72.res created by SHELXL-2018/1 at 12:26:47 on 09-Jul-2020 REM Old TITL G72 LIGAND REM SHELXT solution in P2(1)/n REM R1 0.077, Rweak 0.005, Alpha 0.028, Orientation as input REM Formula found by SHELXT: C14 Br N2 O S CELL 0.71073 3.9592 15.1421 22.2497 90 95.183 90 ZERR 4 0.0004 0.0021 0.0022 0 0.008 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br N O S UNIT 56 44 4 8 4 4 EQIV $1 1-X,1-Y,1-Z L.S. 20 PLAN 5 SIZE 0.034 0.05 0.76 TEMP -153.15 HTAB N2 O1 HTAB N1 S1_$1 BOND $H list 4 MORE -1 fmap 2 acta MERG 2 OMIT -2 58 OMIT -5 3 2 OMIT 1 17 14 REM REM REM WGHT 0.096700 0.612600 FVAR 0.43008 BR1 3 0.833620 0.344330 0.770916 11.00000 0.02142 0.01716 = 0.01984 0.00192 0.00254 0.00371 S1 6 0.625920 0.549608 0.586435 11.00000 0.02045 0.01486 = 0.01472 0.00159 0.00201 -0.00404 O1 5 0.270650 0.274190 0.628561 11.00000 0.05525 0.01629 = 0.01788 0.00271 0.00431 -0.00787 N1 4 0.356236 0.391298 0.566528 11.00000 0.02256 0.01298 = 0.01293 0.00087 0.00181 -0.00177 AFIX 43 H1 2 0.353938 0.406926 0.528399 11.00000 -1.20000 AFIX 0 N2 4 0.407961 0.435706 0.666601 11.00000 0.02440 0.01391 = 0.01368 0.00136 0.00297 -0.00346 AFIX 43 H2 2 0.329777 0.382603 0.673484 11.00000 -1.20000 AFIX 0 C26 1 0.661584 0.461422 0.768824 11.00000 0.01362 0.01629 = 0.01879 0.00224 0.00211 -0.00091 C21 1 0.474750 0.492245 0.717078 11.00000 0.01627 0.01590 = 0.01470 0.00267 0.00503 -0.00127 C23 1 0.393370 0.630141 0.768534 11.00000 0.02034 0.01408 = 0.02320 -0.00031 0.00723 -0.00318 AFIX 43 H23 2 0.297239 0.687607 0.768823 11.00000 -1.20000 AFIX 0 C25 1 0.722968 0.514556 0.819928 11.00000 0.01850 0.02288 = 0.01513 -0.00228 -0.00055 -0.00170 AFIX 43 H25 2 0.853494 0.492943 0.854762 11.00000 -1.20000 AFIX 0 C22 1 0.335187 0.577361 0.717319 11.00000 0.01868 0.01575 = 0.01831 0.00067 0.00340 -0.00278 AFIX 43 H22 2 0.201802 0.598914 0.682784 11.00000 -1.20000 AFIX 0 C1 1 0.453635 0.456184 0.609403 11.00000 0.01408 0.01416 = 0.01358 -0.00054 -0.00016 0.00035 C11 1 0.154574 0.251673 0.522899 11.00000 0.02007 0.01344 = 0.01517 0.00067 0.00470 -0.00392 C14 1 -0.050994 0.146569 0.424032 11.00000 0.02315 0.02329 = 0.02040 -0.00737 0.00529 -0.00731 AFIX 43 H14 2 -0.119601 0.110393 0.390232 11.00000 -1.20000 AFIX 0 C24 1 0.589801 0.599791 0.819047 11.00000 0.02255 0.01867 = 0.01974 -0.00481 0.00572 -0.00287 AFIX 43 H24 2 0.633754 0.637177 0.853146 11.00000 -1.20000 AFIX 0 C16 1 -0.031302 0.288566 0.472801 11.00000 0.01565 0.01704 = 0.01884 -0.00066 0.00240 -0.00235 AFIX 43 H16 2 -0.084947 0.349728 0.472294 11.00000 -1.20000 AFIX 0 C12 1 0.234441 0.161781 0.524232 11.00000 0.02200 0.01549 = 0.01965 0.00097 0.00011 0.00031 AFIX 43 H12 2 0.353727 0.136073 0.558862 11.00000 -1.20000 AFIX 0 C10 1 0.263319 0.305340 0.577665 11.00000 0.02511 0.01331 = 0.01729 0.00191 0.00231 -0.00188 C13 1 0.134961 0.110608 0.473520 11.00000 0.02618 0.01583 = 0.02685 -0.00289 0.00578 -0.00195 AFIX 43 H13 2 0.196328 0.049976 0.473065 11.00000 -1.20000 AFIX 0 C15 1 -0.138267 0.235427 0.423433 11.00000 0.02069 0.02293 = 0.01640 -0.00060 0.00032 -0.00302 AFIX 43 H15 2 -0.269855 0.259882 0.389659 11.00000 -1.20000 AFIX 0 HKLF 4 REM g72_a.res in P2(1)/n REM R1 = 0.0492 for 2917 Fo > 4sig(Fo) and 0.0626 for all 3530 data REM 172 parameters refined using 0 restraints END WGHT 0.0967 0.6126 REM Highest difference peak 1.061, deepest hole -1.475, 1-sigma level 0.177 Q1 1 0.5502 0.3225 0.7595 11.00000 0.05 1.06 Q2 1 0.5843 0.3805 0.7492 11.00000 0.05 0.99 Q3 1 1.1395 0.3395 0.7808 11.00000 0.05 0.97 Q4 1 1.0604 0.3839 0.7981 11.00000 0.05 0.97 Q5 1 0.9585 0.2983 0.7379 11.00000 0.05 0.87 ; _shelx_res_checksum 56368 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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.83362(8) 0.34433(2) 0.77092(2) 0.01943(14) Uani d 1 . . S S1 0.6259(2) 0.54961(5) 0.58644(4) 0.01665(18) Uani d 1 . . O O1 0.2706(9) 0.27419(16) 0.62856(12) 0.0297(6) Uani d 1 . . N N1 0.3562(7) 0.39130(16) 0.56653(12) 0.0161(5) Uani d 1 . . H H1 0.353938 0.406926 0.528399 0.019 Uiso calc 1 . . N N2 0.4080(8) 0.43571(16) 0.66660(13) 0.0173(5) Uani d 1 . . H H2 0.329777 0.382603 0.673484 0.021 Uiso calc 1 . . C C26 0.6616(8) 0.46142(19) 0.76882(15) 0.0162(6) Uani d 1 . . C C21 0.4747(8) 0.49224(19) 0.71708(14) 0.0154(6) Uani d 1 . . C C23 0.3934(9) 0.6301(2) 0.76853(16) 0.0189(6) Uani d 1 . . H H23 0.297239 0.687607 0.768823 0.023 Uiso calc 1 . . C C25 0.7230(8) 0.5146(2) 0.81993(15) 0.0190(6) Uani d 1 . . H H25 0.853494 0.492943 0.854762 0.023 Uiso calc 1 . . C C22 0.3352(8) 0.5774(2) 0.71732(15) 0.0175(6) Uani d 1 . . H H22 0.201802 0.598914 0.682784 0.021 Uiso calc 1 . . C C1 0.4536(8) 0.45618(19) 0.60940(14) 0.0140(5) Uani d 1 . . C C11 0.1546(8) 0.25167(18) 0.52290(14) 0.0160(6) Uani d 1 . . C C14 -0.0510(9) 0.1466(2) 0.42403(17) 0.0221(7) Uani d 1 . . H H14 -0.119601 0.110393 0.390232 0.026 Uiso calc 1 . . C C24 0.5898(9) 0.5998(2) 0.81905(16) 0.0201(6) Uani d 1 . . H H24 0.633754 0.637177 0.853146 0.024 Uiso calc 1 . . C C16 -0.0313(8) 0.2886(2) 0.47280(15) 0.0171(6) Uani d 1 . . H H16 -0.084947 0.349728 0.472294 0.021 Uiso calc 1 . . C C12 0.2344(9) 0.16178(19) 0.52423(16) 0.0192(6) Uani d 1 . . H H12 0.353727 0.136073 0.558862 0.023 Uiso calc 1 . . C C10 0.2633(9) 0.30534(19) 0.57767(15) 0.0185(6) Uani d 1 . . C C13 0.1350(9) 0.1106(2) 0.47352(17) 0.0227(7) Uani d 1 . . H H13 0.196328 0.049976 0.473065 0.027 Uiso calc 1 . . C C15 -0.1383(9) 0.2354(2) 0.42343(15) 0.0201(6) Uani d 1 . . H H15 -0.269855 0.259882 0.389659 0.024 Uiso calc 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0214(2) 0.01716(18) 0.0198(2) 0.00371(10) 0.00254(13) 0.00192(10) S1 0.0205(4) 0.0149(3) 0.0147(4) -0.0040(2) 0.0020(3) 0.0016(2) O1 0.0553(19) 0.0163(11) 0.0179(12) -0.0079(11) 0.0043(12) 0.0027(9) N1 0.0226(13) 0.0130(10) 0.0129(12) -0.0018(9) 0.0018(10) 0.0009(9) N2 0.0244(13) 0.0139(10) 0.0137(12) -0.0035(9) 0.0030(11) 0.0014(9) C26 0.0136(12) 0.0163(12) 0.0188(15) -0.0009(10) 0.0021(12) 0.0022(11) C21 0.0163(13) 0.0159(12) 0.0147(14) -0.0013(10) 0.0050(11) 0.0027(10) C23 0.0203(14) 0.0141(13) 0.0232(16) -0.0032(11) 0.0072(13) -0.0003(11) C25 0.0185(14) 0.0229(14) 0.0151(14) -0.0017(11) -0.0005(12) -0.0023(11) C22 0.0187(14) 0.0157(12) 0.0183(14) -0.0028(10) 0.0034(12) 0.0007(11) C1 0.0141(12) 0.0142(12) 0.0136(13) 0.0004(9) -0.0002(11) -0.0005(10) C11 0.0201(13) 0.0134(12) 0.0152(14) -0.0039(10) 0.0047(12) 0.0007(10) C14 0.0232(16) 0.0233(15) 0.0204(16) -0.0073(12) 0.0053(14) -0.0074(12) C24 0.0225(15) 0.0187(13) 0.0197(15) -0.0029(11) 0.0057(13) -0.0048(11) C16 0.0157(13) 0.0170(12) 0.0188(15) -0.0023(10) 0.0024(12) -0.0007(11) C12 0.0220(15) 0.0155(13) 0.0197(16) 0.0003(10) 0.0001(13) 0.0010(11) C10 0.0251(15) 0.0133(13) 0.0173(15) -0.0019(10) 0.0023(13) 0.0019(10) C13 0.0262(16) 0.0158(13) 0.0268(17) -0.0019(12) 0.0058(14) -0.0029(12) C15 0.0207(15) 0.0229(14) 0.0164(15) -0.0030(11) 0.0003(12) -0.0006(11) 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' Br Br -0.2901 2.4595 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 H1 . . 116.5 ? C10 N1 H1 . . 116.5 ? C10 N1 C1 . . 126.9(3) ? C21 N2 H2 . . 117.2 ? C1 N2 H2 . . 117.2 ? C1 N2 C21 . . 125.6(3) ? C21 C26 Br1 . . 119.8(2) ? C21 C26 C25 . . 121.4(3) ? C25 C26 Br1 . . 118.9(2) ? C26 C21 N2 . . 120.0(3) ? C26 C21 C22 . . 119.0(3) ? C22 C21 N2 . . 120.8(3) ? C22 C23 H23 . . 119.6 ? C24 C23 H23 . . 119.6 ? C24 C23 C22 . . 120.8(3) ? C26 C25 H25 . . 120.5 ? C24 C25 C26 . . 119.0(3) ? C24 C25 H25 . . 120.5 ? C21 C22 H22 . . 120.2 ? C23 C22 C21 . . 119.6(3) ? C23 C22 H22 . . 120.2 ? N1 C1 S1 . . 118.8(2) ? N2 C1 S1 . . 125.5(2) ? N2 C1 N1 . . 115.7(3) ? C16 C11 C12 . . 120.6(3) ? C16 C11 C10 . . 121.7(3) ? C12 C11 C10 . . 117.7(3) ? C13 C14 H14 . . 119.9 ? C13 C14 C15 . . 120.3(3) ? C15 C14 H14 . . 119.9 ? C23 C24 C25 . . 120.2(3) ? C23 C24 H24 . . 119.9 ? C25 C24 H24 . . 119.9 ? C11 C16 H16 . . 120.1 ? C11 C16 C15 . . 119.9(3) ? C15 C16 H16 . . 120.1 ? C11 C12 H12 . . 120.8 ? C13 C12 C11 . . 118.5(3) ? C13 C12 H12 . . 120.8 ? O1 C10 N1 . . 123.0(3) ? O1 C10 C11 . . 121.7(3) ? N1 C10 C11 . . 115.3(3) ? C14 C13 C12 . . 121.1(3) ? C14 C13 H13 . . 119.4 ? C12 C13 H13 . . 119.4 ? C14 C15 C16 . . 119.6(3) ? C14 C15 H15 . . 120.2 ? C16 C15 H15 . . 120.2 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C26 . 1.898(3) ? S1 C1 . 1.671(3) ? O1 C10 . 1.225(4) ? N1 H1 . 0.8800 ? N1 C1 . 1.399(4) ? N1 C10 . 1.381(4) ? N2 H2 . 0.8800 ? N2 C21 . 1.418(4) ? N2 C1 . 1.338(4) ? C26 C21 . 1.392(5) ? C26 C25 . 1.396(4) ? C21 C22 . 1.402(4) ? C23 H23 . 0.9500 ? C23 C22 . 1.394(5) ? C23 C24 . 1.386(5) ? C25 H25 . 0.9500 ? C25 C24 . 1.394(5) ? C22 H22 . 0.9500 ? C11 C16 . 1.396(5) ? C11 C12 . 1.397(4) ? C11 C10 . 1.495(4) ? C14 H14 . 0.9500 ? C14 C13 . 1.380(6) ? C14 C15 . 1.389(5) ? C24 H24 . 0.9500 ? C16 H16 . 0.9500 ? C16 C15 . 1.396(5) ? C12 H12 . 0.9500 ? C12 C13 . 1.396(5) ? C13 H13 . 0.9500 ? C15 H15 . 0.9500 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 S1 3_666 0.88 2.65 3.526(3) 177.4 yes N2 H2 O1 . 0.88 1.93 2.629(4) 135.8 yes _cod_database_fobs_code 2022289