#------------------------------------------------------------------------------ #$Date: 2024-08-14 04:52:55 +0300 (Wed, 14 Aug 2024) $ #$Revision: 294106 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312578.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_2312578 loop_ _publ_author_name 'Bosch, Eric' 'Bowling, Nathan P.' _publ_section_title ; Role of secondary interactions in a series of 2:1 halogen-bonded cocrystals formed between 4-(dimethylamino)pyridine and ditopic halogen-bond donors. ; _journal_coeditor_code VP3039 _journal_issue 9 _journal_name_full 'Acta crystallographica. Section C, Structural chemistry' _journal_paper_doi 10.1107/S205322962400771X _journal_volume 80 _journal_year 2024 _chemical_formula_iupac '2C7 H10 N2, C6 Br F4 I' _chemical_formula_moiety '2(C7 H10 N2), C6 Br F4 I' _chemical_formula_sum 'C20 H20 Br F4 I N4' _chemical_formula_weight 599.210 _chemical_name_systematic ; 4-(Dimethylamino)pyridine--1-bromo-4-iodo-2,3,5,6-tetrafluorobenzene (2/1) ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_primary dual _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 106.304(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.38980(10) _cell_length_b 16.2120(2) _cell_length_c 9.42360(10) _cell_measurement_reflns_used 6158 _cell_measurement_temperature 100.01(15) _cell_measurement_theta_max 77.1460 _cell_measurement_theta_min 2.6950 _cell_volume 1083.58(3) _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2023) ; _computing_data_collection ; CrysAlis PRO (Rigaku OD, 2023) ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2023) ; _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; olex2.refine (Bourhis et al., 2015) ; _computing_structure_solution ; SHELXT2018 (Sheldrick, 2015) ; _diffrn_ambient_temperature 100.01(15) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.9995 _diffrn_measured_fraction_theta_max 0.9970 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10454 _diffrn_reflns_theta_full 67.6840 _diffrn_reflns_theta_max 77.78 _diffrn_reflns_theta_min 5.46 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 14.213 _exptl_absorpt_correction_T_max 0.595 _exptl_absorpt_correction_T_min 0.357 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2023) ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.837 _exptl_crystal_description irregular _exptl_crystal_F_000 584.861 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.7481 _refine_diff_density_min -0.5799 _refine_ls_extinction_coef 0.00052(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.9978 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 17 _refine_ls_number_parameters 142 _refine_ls_number_reflns 2300 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.9974 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0341 _refine_ls_shift/su_max -0.0003 _refine_ls_shift/su_mean 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+7.3962P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.0800 _reflns_number_gt 2252 _reflns_number_total 2300 _reflns_threshold_expression I>=2u(I) _iucr_refine_instructions_details ; TITL eb_a_188_1_auto_a.res in P2(1)/c CELL 1.54184 7.3898 16.212 9.4236 90 106.304 90 ZERR 2 0.0001 0.0002 0.0001 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br F I N UNIT 40 40 2 8 2 8 DFIX 1.85 C8 Br1 DFIX 2.09 C8 I1 EADP Br1 I1 L.S. 10 PLAN 20 0 0 SIZE 0.05 0.08 0.12 TEMP -173 CONF BOND FMAP 2 1 53 LIST 4 1 MORE -1 BOND $H ACTA EXTI 0.000517 WGHT 0 7.396198 FVAR 0.352459 REM REM REM PART 2 Br1 3 0.59714 0.19937 0.51922 10.50000 0.01840 0.00755 0.01871 = -0.00060 0.00365 -0.00090 PART 0 F1 4 0.85158 0.05177 0.50859 11.00000 0.01428 0.02284 0.02576 = -0.00076 0.00627 -0.00280 F2 4 0.77553 -0.10968 0.49315 11.00000 0.01772 0.01876 0.03138 = -0.00144 0.00767 0.00417 N2 6 0.82910 0.61742 0.51795 11.00000 0.03051 0.01714 0.02023 = -0.00002 0.00415 -0.00494 N1 6 0.68384 0.36793 0.53764 11.00000 0.01741 0.02319 0.02573 = 0.00116 0.00511 0.00080 C9 1 0.67587 0.02705 0.50396 11.00000 0.01522 0.01902 0.01398 = 0.00145 0.00147 -0.00407 C8 1 0.54000 0.08564 0.50673 11.00000 0.01754 0.01463 0.01698 = -0.00032 0.00421 -0.00137 C3 1 0.78139 0.53697 0.52506 11.00000 0.01866 0.01876 0.01910 = -0.00313 0.00858 -0.00017 C4 1 0.83295 0.49144 0.65847 11.00000 0.01999 0.01936 0.01968 = -0.00103 0.00583 0.00027 AFIX 43 H4 2 0.90346 0.51675 0.74781 11.00000 -1.20000 AFIX 0 C10 1 0.63743 -0.05620 0.49656 11.00000 0.01771 0.01746 0.01671 = 0.00050 0.00570 0.00230 C1 1 0.63202 0.41224 0.41110 11.00000 0.02216 0.02569 0.01802 = -0.00350 0.00545 0.00028 AFIX 43 H1 2 0.55832 0.38523 0.32469 11.00000 -1.20000 AFIX 0 C5 1 0.77957 0.40978 0.65724 11.00000 0.02330 0.02185 0.01939 = 0.00088 0.00618 0.00204 AFIX 43 H5 2 0.81366 0.38106 0.74880 11.00000 -1.20000 AFIX 0 C2 1 0.67808 0.49345 0.39831 11.00000 0.02390 0.01998 0.01538 = 0.00058 0.00408 -0.00028 AFIX 43 H2 2 0.64072 0.52015 0.30488 11.00000 -1.20000 AFIX 0 C6 1 0.77495 0.66159 0.37881 11.00000 0.03331 0.01940 0.02507 = 0.00212 0.01013 0.00005 AFIX 137 H6a 2 0.82614 0.63322 0.30671 11.00000 -1.50000 H6b 2 0.63714 0.66353 0.34182 11.00000 -1.50000 H6c 2 0.82495 0.71789 0.39374 11.00000 -1.50000 AFIX 0 C7 1 0.92792 0.66203 0.65210 11.00000 0.03644 0.02037 0.02692 = -0.00469 0.00413 -0.00852 AFIX 137 H7a 2 0.85281 0.66034 0.72280 11.00000 -1.50000 H7b 2 1.05071 0.63616 0.69621 11.00000 -1.50000 H7c 2 0.94650 0.71952 0.62722 11.00000 -1.50000 AFIX 0 PART 2 I1 5 0.60492 0.21223 0.51970 10.50000 0.01840 0.00755 0.01871 = -0.00060 0.00365 -0.00090 HKLF 4 END Q1 1 0.6 0.05 0.53125 11 0.05 0.75 Q2 1 0.68 0.183333 0.46875 11 0.05 0.74 REM The information below was added by Olex2. REM REM R1 = 0.0341 for 2252 Fo > 4sig(Fo) and 0.0348 for all 2300 data REM 142 parameters refined using 2 restraints REM Highest difference peak 0.7481, deepest hole -0.5799 REM Mean Shift 0.0000, Max Shift -0.0003. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0348 REM R1_gt = 0.0341 REM wR_ref = 0.0800 REM GOOF = 0.9978 REM Shift_max = -0.0003 REM Shift_mean = 0.0000 REM Reflections_all = 2300 REM Reflections_gt = 2252 REM Parameters = 142 REM Hole = -0.5799 REM Peak = 0.7481 REM Flack = n/a ; _cod_data_source_file vp3039sup1.cif _cod_data_source_block 2DMAP.IBTFB _cod_database_code 2312578 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-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_occupancy _atom_site_disorder_group Br Br1 0.5971(11) 0.1994(3) 0.5192(9) 0.0152(3) Uani 0.500000 2 F F1 0.8516(3) 0.05177(14) 0.5086(3) 0.0208(5) Uani 1.000000 . F F2 0.7755(3) -0.10968(14) 0.4932(3) 0.0225(5) Uani 1.000000 . N N2 0.8291(5) 0.6174(2) 0.5179(4) 0.0232(7) Uani 1.000000 . N N1 0.6838(5) 0.3679(2) 0.5376(4) 0.0223(7) Uani 1.000000 . C C9 0.6759(5) 0.0271(2) 0.5040(4) 0.0166(7) Uani 1.000000 . C C8 0.5400(5) 0.0856(2) 0.5067(4) 0.0165(7) Uani 1.000000 . C C3 0.7814(5) 0.5370(2) 0.5251(4) 0.0182(7) Uani 1.000000 . C C4 0.8329(5) 0.4914(2) 0.6585(4) 0.0196(8) Uani 1.000000 . H H4 0.9035(5) 0.5168(2) 0.7478(4) 0.0236(9) Uiso 1.000000 . C C10 0.6374(5) -0.0562(2) 0.4966(4) 0.0171(7) Uani 1.000000 . C C1 0.6320(6) 0.4122(3) 0.4111(4) 0.0220(8) Uani 1.000000 . H H1 0.5583(6) 0.3852(3) 0.3247(4) 0.0264(10) Uiso 1.000000 . C C5 0.7796(6) 0.4098(3) 0.6572(5) 0.0215(8) Uani 1.000000 . H H5 0.8137(6) 0.3811(3) 0.7488(5) 0.0258(10) Uiso 1.000000 . C C2 0.6781(6) 0.4934(2) 0.3983(4) 0.0200(8) Uani 1.000000 . H H2 0.6407(6) 0.5202(2) 0.3049(4) 0.0241(9) Uiso 1.000000 . C C6 0.7750(6) 0.6616(3) 0.3788(5) 0.0255(9) Uani 1.000000 . H H6a 0.826(4) 0.6332(11) 0.3067(12) 0.0383(13) Uiso 1.000000 . H H6b 0.6371(6) 0.6635(18) 0.3418(19) 0.0383(13) Uiso 1.000000 . H H6c 0.825(4) 0.7179(7) 0.3937(9) 0.0383(13) Uiso 1.000000 . C C7 0.9279(7) 0.6620(3) 0.6521(5) 0.0289(9) Uani 1.000000 . H H7a 0.853(2) 0.6603(19) 0.7228(16) 0.0433(14) Uiso 1.000000 . H H7b 1.051(2) 0.6362(13) 0.696(2) 0.0433(14) Uiso 1.000000 . H H7c 0.946(4) 0.7195(6) 0.6272(8) 0.0433(14) Uiso 1.000000 . I I1 0.6049(7) 0.21223(17) 0.5197(5) 0.0152(3) Uani 0.500000 2 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 0.0184(4) 0.0075(9) 0.01871(18) -0.0009(7) 0.0037(2) -0.0006(7) F1 0.0143(10) 0.0228(12) 0.0258(12) -0.0028(9) 0.0063(9) -0.0008(9) F2 0.0177(11) 0.0188(11) 0.0314(13) 0.0042(9) 0.0077(9) -0.0014(9) N2 0.0305(18) 0.0171(16) 0.0202(17) -0.0049(14) 0.0042(14) 0.0000(13) N1 0.0174(15) 0.0232(18) 0.0257(18) 0.0008(13) 0.0051(13) 0.0012(14) C9 0.0152(16) 0.0190(19) 0.0140(17) -0.0041(14) 0.0015(13) 0.0014(14) C8 0.0175(17) 0.0146(17) 0.0170(18) -0.0014(14) 0.0042(14) -0.0003(14) C3 0.0187(17) 0.0188(18) 0.0191(18) -0.0002(15) 0.0086(15) -0.0031(15) C4 0.0200(18) 0.0194(19) 0.0197(19) 0.0003(15) 0.0058(15) -0.0010(15) C10 0.0177(17) 0.0175(18) 0.0167(18) 0.0023(14) 0.0057(14) 0.0005(14) C1 0.0222(19) 0.026(2) 0.0180(19) 0.0003(16) 0.0055(15) -0.0035(16) C5 0.0233(19) 0.022(2) 0.0194(19) 0.0020(16) 0.0062(15) 0.0009(15) C2 0.0239(19) 0.0200(19) 0.0154(18) -0.0003(15) 0.0041(15) 0.0006(15) C6 0.033(2) 0.019(2) 0.025(2) 0.0001(17) 0.0101(18) 0.0021(16) C7 0.036(2) 0.020(2) 0.027(2) -0.0085(18) 0.0041(19) -0.0047(17) I1 0.0184(4) 0.0075(9) 0.01871(18) -0.0009(7) 0.0037(2) -0.0006(7) loop_ _atom_type_symbol _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_dispersion_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090 41.43280 2.95570 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' -0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' C 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870 51.65120 0.21560 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' F 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150 26.14760 0.27760 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.07537 0.05506 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' H 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236 57.79970 0.00304 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' I 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600 66.87760 4.07120 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' -0.19206 6.94430 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' N 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750 0.58260 -11.52900 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' loop_ _diffrn_refln_index_h _diffrn_refln_index_k _diffrn_refln_index_l 0 0 -1 0 0 -2 0 0 -3 0 0 4 0 0 -4 0 0 -5 0 0 5 0 0 6 0 0 6 0 0 6 0 0 6 0 0 7 0 0 7 0 0 7 0 0 8 0 0 8 0 0 9 0 0 10 0 0 10 0 0 11 0 1 0 0 -1 -1 0 1 -2 0 -1 -2 0 -1 3 0 1 -3 0 -1 -3 0 1 -4 0 -1 4 0 -1 -4 0 1 5 0 -1 5 0 -1 -5 0 -1 6 0 1 6 0 -1 6 0 -1 -6 0 -1 6 0 -1 6 0 1 6 0 -1 6 0 1 7 0 -1 7 0 -1 7 0 -1 7 0 1 7 0 -1 7 0 1 8 0 -1 8 0 1 8 0 -1 8 0 -1 8 0 -1 9 0 1 9 0 -1 9 0 1 10 0 -1 10 0 1 10 0 1 11 0 2 0 0 -2 -1 0 -2 -2 0 -2 -3 0 -2 3 0 -2 4 0 -2 -4 0 -2 5 0 -2 -5 0 -2 6 0 -2 -6 0 2 6 0 -2 6 0 -2 6 0 2 6 0 -2 6 0 -2 7 0 -2 7 0 -2 -7 0 2 7 0 -2 7 0 2 7 0 -2 7 0 -2 8 0 2 8 0 -2 8 0 2 8 0 -2 9 0 2 9 0 -2 9 0 -2 10 0 2 10 0 -2 10 0 -2 10 0 -2 11 0 2 11 0 3 0 0 -3 -1 0 -3 -2 0 -3 -3 0 -3 3 0 -3 -4 0 -3 4 0 -3 -4 0 -3 5 0 -3 -5 0 -3 6 0 -3 -6 0 3 6 0 -3 6 0 -3 6 0 -3 6 0 -3 6 0 -3 6 0 -3 7 0 -3 7 0 -3 -7 0 3 7 0 -3 7 0 3 7 0 -3 7 0 -3 7 0 -3 8 0 3 8 0 3 8 0 -3 8 0 -3 9 0 3 9 0 -3 10 0 -3 10 0 3 10 0 -3 11 0 3 11 0 3 11 0 4 0 0 -4 -1 0 4 -1 0 -4 -2 0 -4 -3 0 -4 3 0 -4 -4 0 -4 4 0 -4 5 0 -4 -5 0 -4 6 0 -4 6 0 -4 6 0 -4 6 0 4 6 0 -4 6 0 -4 -6 0 -4 7 0 -4 7 0 4 7 0 -4 -7 0 4 7 0 -4 7 0 -4 7 0 -4 7 0 -4 8 0 4 8 0 -4 8 0 -4 8 0 -4 8 0 4 8 0 -4 9 0 4 9 0 -4 10 0 4 10 0 -4 10 0 -4 10 0 4 10 0 4 11 0 -4 11 0 5 0 0 -5 -1 0 5 -1 0 -5 -2 0 -5 -3 0 -5 -4 0 -5 -5 0 -5 6 0 5 6 0 -5 6 0 -5 6 0 -5 6 0 -5 -6 0 -5 -7 0 5 7 0 -5 7 0 -5 7 0 -5 7 0 -5 7 0 5 7 0 -5 7 0 5 8 0 -5 8 0 5 8 0 -5 8 0 -5 8 0 5 8 0 -5 8 0 -5 8 0 -5 9 0 -5 9 0 5 9 0 -5 9 0 -5 10 0 5 10 0 -5 10 0 -5 10 0 5 10 0 5 11 0 6 0 0 6 -1 0 -6 -1 0 6 -2 0 -6 -2 0 -6 -3 0 -6 -4 0 -6 -5 0 -6 5 0 -6 -5 0 -6 -6 0 -6 6 0 -6 6 0 6 6 0 -6 6 0 -6 6 0 -6 -7 0 -6 7 0 -6 7 0 6 7 0 -6 7 0 -6 7 0 -6 7 0 6 8 0 -6 8 0 -6 8 0 -6 8 0 -6 8 0 6 8 0 -6 8 0 6 9 0 -6 9 0 -6 9 0 -6 9 0 -6 9 0 6 9 0 6 10 0 -6 10 0 6 10 0 6 10 0 -6 10 0 -6 10 0 -7 0 0 7 -1 0 -7 -1 0 -7 -2 0 7 -2 0 -7 2 0 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4 -9 2 4 -9 2 4 -9 2 3 -9 2 3 -9 -2 2 -9 2 2 -9 -2 1 -9 2 1 -9 2 1 -9 3 5 -9 3 5 -9 -3 4 -9 3 4 -9 3 4 -9 3 3 -9 3 3 -9 -3 2 -9 -3 1 -9 4 5 -9 4 4 -9 -4 4 -9 4 3 -9 4 3 -9 -4 2 -9 5 4 -9 -5 3 -9 -5 2 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 -2 -1 0.0415 -1 0 2 0.0459 -1 1 2 0.0529 0 2 1 0.0468 1 -1 -2 0.0469 -1 2 1 0.0621 1 2 -1 0.0414 0 -2 1 0.0433 0 2 -1 0.0441 2 0 -1 0.0372 -2 0 1 0.0519 -2 1 0 0.0447 2 -1 0 0.0267 -2 2 -1 0.0411 -2 0 -1 0.0322 1 1 -2 0.0381 -2 -1 -1 0.0310 2 1 1 0.0213 0 0 -1 0.0343 -1 -2 0 0.0423 1 -1 -1 0.0457 0 -4 1 0.0502 2 5 -3 0.0419 -1 -5 2 0.0472 -3 5 -1 0.0433 3 -4 2 0.0277 0 -3 -4 0.0388 0 2 3 0.0420 -1 -5 0 0.0490 1 5 0 0.0350 0 5 1 0.0464 4 -1 3 0.0177 0 0 1 0.0339 -3 -3 5 0.0417 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 C6 N2 C3 . . 120.7(3) ? C7 N2 C3 . . 120.4(3) ? C7 N2 C6 . . 118.8(3) ? C5 N1 C1 . . 115.2(4) ? C8 C9 F1 . . 119.4(3) ? C10 C9 F1 . . 118.4(3) ? C10 C9 C8 . . 122.1(3) ? C9 C8 Br1 . . 121.3(4) ? C10 C8 Br1 3_656 . 122.1(4) ? C10 C8 C9 3_656 . 116.6(3) ? I1 C8 C9 . . 121.0(3) ? I1 C8 C10 . 3_656 122.4(3) ? C4 C3 N2 . . 122.4(4) ? C2 C3 N2 . . 121.6(4) ? C2 C3 C4 . . 115.9(4) ? H4 C4 C3 . . 120.4(2) ? C5 C4 C3 . . 119.2(4) ? C5 C4 H4 . . 120.4(2) ? C9 C10 F2 . . 119.0(3) ? C8 C10 F2 3_656 . 119.7(3) ? C8 C10 C9 3_656 . 121.2(4) ? H1 C1 N1 . . 117.6(2) ? C2 C1 N1 . . 124.8(4) ? C2 C1 H1 . . 117.6(2) ? C4 C5 N1 . . 125.2(4) ? H5 C5 N1 . . 117.4(2) ? H5 C5 C4 . . 117.4(2) ? C1 C2 C3 . . 119.5(4) ? H2 C2 C3 . . 120.2(2) ? H2 C2 C1 . . 120.2(2) ? H6a C6 N2 . . 109.5 ? H6b C6 N2 . . 109.5 ? H6b C6 H6a . . 109.5 ? H6c C6 N2 . . 109.5 ? H6c C6 H6a . . 109.5 ? H6c C6 H6b . . 109.5 ? H7a C7 N2 . . 109.5 ? H7b C7 N2 . . 109.5 ? H7b C7 H7a . . 109.5 ? H7c C7 N2 . . 109.5 ? H7c C7 H7a . . 109.5 ? H7c C7 H7b . . 109.5 ? 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 C8 . 1.888(6) ? Br1 I1 . 0.216(8) ? F1 C9 . 1.348(4) ? F2 C10 . 1.346(4) ? N2 C3 . 1.358(5) ? N2 C6 . 1.448(5) ? N2 C7 . 1.462(5) ? N1 C1 . 1.352(5) ? N1 C5 . 1.336(5) ? C9 C8 . 1.388(5) ? C9 C10 . 1.377(5) ? C8 C10 3_656 1.387(5) ? C8 I1 . 2.103(5) ? C3 C4 . 1.415(6) ? C3 C2 . 1.413(5) ? C4 H4 . 0.9500 ? C4 C5 . 1.380(6) ? C1 H1 . 0.9500 ? C1 C2 . 1.373(6) ? C5 H5 . 0.9500 ? C2 H2 . 0.9500 ? C6 H6a . 0.9800 ? C6 H6b . 0.9800 ? C6 H6c . 0.9800 ? C7 H7a . 0.9800 ? C7 H7b . 0.9800 ? C7 H7c . 0.9800 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br1 C8 C9 F1 . . . . -0.8(4) ? Br1 C8 C9 C10 . . . . 179.3(4) ? Br1 C8 C10 F2 . . 3_656 3_656 1.1(5) ? Br1 C8 C10 C9 . . 3_656 3_656 -179.2(4) ? F1 C9 C8 C10 . . . 3_656 -179.3(3) ? F1 C9 C8 I1 . . . . -0.5(4) ? F1 C9 C10 F2 . . . . -0.5(4) ? F1 C9 C10 C8 . . . 3_656 179.2(3) ? F2 C10 C9 C8 . . . . 179.5(3) ? F2 C10 C8 C9 . . 3_656 3_656 -179.6(3) ? F2 C10 C8 I1 . . 3_656 3_656 -0.8(4) ? N2 C3 C4 C5 . . . . -179.9(4) ? N2 C3 C2 C1 . . . . -179.6(4) ? N1 C1 C2 C3 . . . . -2.4(5) ? N1 C5 C4 C3 . . . . 1.4(5) ? C9 C8 C10 C9 . . 3_656 3_656 -0.7(3) ? C9 C10 C8 C9 . . 3_656 3_656 0.7(4) ? C9 C10 C8 I1 . . 3_656 3_656 179.5(3) ? loop_ _restr_distance_atom_site_label_1 _restr_distance_atom_site_label_2 _restr_distance_site_symmetry_2 _restr_distance_target _restr_distance_target_weight_param C8 Br1 1 1.8500 0.0200 C8 I1 1 2.0900 0.0200 _cod_database_fobs_code 2312578