#------------------------------------------------------------------------------ #$Date: 2022-10-04 19:16:05 +0100 (Tue, 04 Oct 2022) $ #$Revision: 278330 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500129.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_3500129 loop_ _publ_author_name 'Lautmann, Michael' 'Maris, Thierry' 'Wuest, James D.' _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. (2008). Acta Cryst. A64, 112-122. ; _publ_section_title ; 2,2',4,4'-tetrabromodiphenylamine ; _journal_name_full 'Personal communication to COD' _journal_year 2022 _chemical_absolute_configuration . _chemical_formula_moiety 'C12 H7 Br4 N' _chemical_formula_sum 'C12 H7 Br4 N' _chemical_formula_weight 484.83 _chemical_name_common 2,2',4,4'-tetrabromodiphenylamine _chemical_name_systematic ; Benzenamine, 2,4-dibromo-N-(2,4-dibromophenyl)- ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2022-10-04 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 105.352(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.8662(7) _cell_length_b 3.9711(3) _cell_length_c 17.3372(12) _cell_measurement_reflns_used 6850 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 68.821 _cell_measurement_theta_min 2.643 _cell_volume 655.03(8) _computing_cell_refinement 'SAINT v7.06A (Bruker, 2003)' _computing_data_collection 'SMART (Bruker, 2003)' _computing_data_reduction 'SAINT v7.06A (Bruker, 2003)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 200.15 _diffrn_detector_area_resol_mean 5.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.0073 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1680 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.811 _diffrn_reflns_theta_min 2.643 _diffrn_source_current 25.0 _diffrn_source_power 1.0 _diffrn_source_voltage 40.0 _exptl_absorpt_coefficient_mu 14.795 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.420775 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.1421 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.4208. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.458 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 452 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.012 _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. ; _refine_diff_density_max 0.668 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.152 _refine_ls_abs_structure_details ; No quotients, so Flack parameter determined by classical intensity fit ; _refine_ls_abs_structure_Flack 0.12(5) _refine_ls_extinction_coef 0.0044(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 1680 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0353 _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^)+(0.0825P)^2^+0.5256P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.0997 _refine_special_details ; Refined as a 2-component twin. 1. Twinned data refinement Scales: 0.646(3) 0.354(3) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C6(H6), N7(H7), C9(H9), C10(H10), C12(H12) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full 0.000 _reflns_Friedel_fraction_max 0.000 _reflns_number_gt 1677 _reflns_number_total 1680 _reflns_special_details ; _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. Completness statistics refer to single and composite reflections containing twin component 1 only. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jiw987.cif _cod_data_source_block jiw987 _cod_database_code 3500129 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, 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 Br4 Br 0.14073(8) 0.1527(3) 0.57457(4) 0.0371(3) Uani 1 1 d . . . . . Br3 Br 0.72001(8) 0.1536(3) 0.59364(4) 0.0366(3) Uani 1 1 d . . . . . Br2 Br 0.23506(8) 0.6341(3) 1.08767(4) 0.0395(3) Uani 1 1 d . . . . . Br1 Br -0.02300(7) 0.8528(3) 0.75952(4) 0.0339(3) Uani 1 1 d . . . . . C1 C 0.2349(8) 0.584(2) 0.9783(4) 0.0302(16) Uani 1 1 d . . . . . C2 C 0.3453(8) 0.419(3) 0.9605(4) 0.0330(19) Uani 1 1 d . . . . . H2 H 0.418658 0.325162 1.001930 0.040 Uiso 1 1 calc R U . . . C3 C 0.3479(7) 0.390(2) 0.8800(4) 0.0287(16) Uani 1 1 d . . . . . H3 H 0.423156 0.274263 0.866990 0.034 Uiso 1 1 calc R U . . . C4 C 0.2411(7) 0.530(2) 0.8191(4) 0.0286(15) Uani 1 1 d . . . . . C5 C 0.1290(7) 0.683(2) 0.8416(4) 0.0285(15) Uani 1 1 d . . . . . C6 C 0.1242(7) 0.712(2) 0.9199(4) 0.0306(17) Uani 1 1 d . . . . . H6 H 0.046813 0.816710 0.933174 0.037 Uiso 1 1 calc R U . . . N7 N 0.2399(6) 0.504(2) 0.7388(4) 0.0366(17) Uani 1 1 d . . . . . H7 H 0.158454 0.538381 0.703861 0.044 Uiso 1 1 calc R U . . . C8 C 0.3522(8) 0.430(2) 0.7076(4) 0.0298(17) Uani 1 1 d . . . . . C9 C 0.4900(8) 0.519(3) 0.7443(4) 0.0310(17) Uani 1 1 d . . . . . H9 H 0.510242 0.636269 0.793857 0.037 Uiso 1 1 calc R U . . . C10 C 0.5997(7) 0.442(2) 0.7107(4) 0.0307(18) Uani 1 1 d . . . . . H10 H 0.693520 0.501807 0.737492 0.037 Uiso 1 1 calc R U . . . C11 C 0.5714(8) 0.279(2) 0.6394(4) 0.0305(18) Uani 1 1 d . . . . . C12 C 0.4353(8) 0.194(2) 0.5986(4) 0.0288(16) Uani 1 1 d . . . . . H12 H 0.416540 0.083544 0.548217 0.035 Uiso 1 1 calc R U . . . C13 C 0.3270(8) 0.272(2) 0.6324(4) 0.0288(17) Uani 1 1 d . . . . . 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 Br4 0.0293(4) 0.0508(5) 0.0267(4) -0.0051(4) -0.0006(3) -0.0047(5) Br3 0.0342(4) 0.0505(5) 0.0261(4) 0.0035(4) 0.0100(3) 0.0068(4) Br2 0.0429(5) 0.0534(6) 0.0226(4) -0.0034(5) 0.0093(3) -0.0040(5) Br1 0.0264(4) 0.0439(5) 0.0286(4) 0.0037(4) 0.0021(3) 0.0036(4) C1 0.032(3) 0.037(4) 0.021(3) -0.002(3) 0.006(3) -0.003(4) C2 0.030(4) 0.044(5) 0.022(3) 0.004(4) 0.002(3) -0.001(4) C3 0.028(3) 0.033(4) 0.025(3) 0.000(4) 0.007(3) -0.001(4) C4 0.026(3) 0.034(4) 0.027(3) 0.001(3) 0.008(3) -0.003(3) C5 0.025(3) 0.031(4) 0.025(3) 0.002(4) 0.000(3) 0.004(3) C6 0.026(4) 0.034(4) 0.031(4) -0.001(3) 0.006(3) -0.002(4) N7 0.029(3) 0.056(5) 0.020(3) -0.005(3) -0.001(2) 0.003(4) C8 0.030(4) 0.039(4) 0.019(3) -0.003(3) 0.003(3) -0.003(3) C9 0.038(4) 0.037(4) 0.019(3) 0.000(3) 0.009(3) 0.003(4) C10 0.026(3) 0.041(5) 0.025(3) 0.006(4) 0.007(3) -0.006(4) C11 0.031(4) 0.041(5) 0.021(3) 0.005(3) 0.010(3) 0.004(3) C12 0.036(4) 0.031(4) 0.017(3) 0.000(3) 0.001(3) -0.001(4) C13 0.031(3) 0.039(5) 0.012(3) 0.006(3) -0.001(3) 0.004(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' 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 C2 C1 Br2 118.7(5) . . C6 C1 Br2 119.1(6) . . C6 C1 C2 122.2(7) . . C1 C2 H2 120.5 . . C1 C2 C3 119.0(7) . . C3 C2 H2 120.5 . . C2 C3 H3 119.7 . . C4 C3 C2 120.7(7) . . C4 C3 H3 119.7 . . C3 C4 C5 117.1(7) . . N7 C4 C3 122.1(7) . . N7 C4 C5 120.7(7) . . C4 C5 Br1 118.0(5) . . C6 C5 Br1 119.0(6) . . C6 C5 C4 123.0(7) . . C1 C6 H6 121.0 . . C5 C6 C1 117.9(7) . . C5 C6 H6 121.0 . . C4 N7 H7 116.2 . . C8 N7 C4 127.6(6) . . C8 N7 H7 116.2 . . N7 C8 C13 119.5(6) . . C9 C8 N7 123.7(7) . . C9 C8 C13 116.7(7) . . C8 C9 H9 119.1 . . C8 C9 C10 121.9(7) . . C10 C9 H9 119.1 . . C9 C10 H10 120.3 . . C11 C10 C9 119.5(7) . . C11 C10 H10 120.3 . . C10 C11 Br3 120.5(6) . . C10 C11 C12 121.3(7) . . C12 C11 Br3 118.2(6) . . C11 C12 H12 120.6 . . C13 C12 C11 118.8(7) . . C13 C12 H12 120.6 . . C8 C13 Br4 120.5(6) . . C12 C13 Br4 117.8(5) . . C12 C13 C8 121.7(7) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br4 C13 1.906(7) . Br3 C11 1.909(7) . Br2 C1 1.907(7) . Br1 C5 1.897(7) . C1 C2 1.375(11) . C1 C6 1.375(10) . C2 H2 0.9500 . C2 C3 1.408(10) . C3 H3 0.9500 . C3 C4 1.394(10) . C4 C5 1.406(11) . C4 N7 1.393(9) . C5 C6 1.374(10) . C6 H6 0.9500 . N7 H7 0.8800 . N7 C8 1.386(10) . C8 C9 1.386(11) . C8 C13 1.409(10) . C9 H9 0.9500 . C9 C10 1.393(10) . C10 H10 0.9500 . C10 C11 1.357(11) . C11 C12 1.384(11) . C12 H12 0.9500 . C12 C13 1.384(11) . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C6 H6 Br2 0.95 2.99 3.892(7) 159.7 2_557 yes N7 H7 Br1 0.88 2.57 3.044(7) 114.6 . yes C10 H10 Br1 0.95 3.06 3.946(7) 156.5 1_655 yes C12 H12 Br3 0.95 3.00 3.918(8) 161.9 2_646 yes 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Br3 C11 C12 C13 177.6(7) . . . . Br2 C1 C2 C3 -178.1(7) . . . . Br2 C1 C6 C5 177.7(7) . . . . Br1 C5 C6 C1 179.3(7) . . . . C1 C2 C3 C4 0.7(14) . . . . C2 C1 C6 C5 -2.8(13) . . . . C2 C3 C4 C5 -3.1(12) . . . . C2 C3 C4 N7 -179.5(9) . . . . C3 C4 C5 Br1 -176.4(6) . . . . C3 C4 C5 C6 2.8(13) . . . . C3 C4 N7 C8 -19.1(15) . . . . C4 C5 C6 C1 0.1(13) . . . . C4 N7 C8 C9 -31.2(16) . . . . C4 N7 C8 C13 152.2(9) . . . . C5 C4 N7 C8 164.6(9) . . . . C6 C1 C2 C3 2.5(14) . . . . N7 C4 C5 Br1 0.0(11) . . . . N7 C4 C5 C6 179.2(9) . . . . N7 C8 C9 C10 -179.7(9) . . . . N7 C8 C13 Br4 -1.0(12) . . . . N7 C8 C13 C12 179.8(9) . . . . C8 C9 C10 C11 1.1(15) . . . . C9 C8 C13 Br4 -177.8(7) . . . . C9 C8 C13 C12 3.1(13) . . . . C9 C10 C11 Br3 -177.5(7) . . . . C9 C10 C11 C12 1.1(14) . . . . C10 C11 C12 C13 -1.1(13) . . . . C11 C12 C13 Br4 179.7(6) . . . . C11 C12 C13 C8 -1.1(13) . . . . C13 C8 C9 C10 -3.1(13) . . . . loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.646(3) 2 0.354(3) _cod_database_fobs_code 3500129