#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202329.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_2202329 loop_ _publ_author_name 'Jones, Peter G.' 'Lozano, Virginia' _publ_section_title ; A second polymorph of 2,5-dibromoanilinium bromide ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1092 _journal_page_last o1094 _journal_paper_doi 10.1107/S160053680301465X _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C6 H6 Br2 N 1+ , Br 1-' _chemical_formula_moiety 'C6 H6 Br2 N 1+ , Br 1-' _chemical_formula_sum 'C6 H6 Br3 N' _chemical_formula_weight 331.85 _chemical_name_systematic ; 2,5-dibromoanilinium bromide ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 106.815(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.3640(12) _cell_length_b 6.5476(11) _cell_length_c 8.5472(12) _cell_measurement_reflns_used 3592 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 30.5 _cell_measurement_theta_min 2.5 _cell_volume 448.07(12) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 133(2) _diffrn_detector_area_resol_mean 8.192 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\w and \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7449 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.04 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 13.432 _exptl_absorpt_correction_T_max 0.494 _exptl_absorpt_correction_T_min 0.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 308 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.879 _refine_diff_density_min -1.270 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 1408 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0298 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0487P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.0743 _reflns_number_gt 1200 _reflns_number_total 1408 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6297.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/m' _cod_database_code 2202329 _cod_database_fobs_code 2202329 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' loop_ _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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Br1 1.07907(4) 0.2500 0.21456(4) 0.02239(12) Uani d S 1 . . Br Br2 0.56532(5) 0.2500 0.66742(5) 0.02522(12) Uani d S 1 . . Br N 0.6968(4) 0.2500 0.0977(4) 0.0191(6) Uani d SD 1 . . N H01 0.581(3) 0.2500 0.063(5) 0.031(12) Uiso d SD 1 . . H H02 0.728(3) 0.137(4) 0.051(3) 0.023(7) Uiso d D 1 . . H C1 0.7619(4) 0.2500 0.2757(4) 0.0185(7) Uani d S 1 . . C C2 0.9341(4) 0.2500 0.3492(4) 0.0183(6) Uani d S 1 . . C C3 0.9960(5) 0.2500 0.5177(4) 0.0214(7) Uani d S 1 . . C H3 1.1133 0.2500 0.5678 0.026 Uiso calc SR 1 . . H C4 0.8878(5) 0.2500 0.6142(4) 0.0215(7) Uani d S 1 . . C H4 0.9299 0.2500 0.7300 0.026 Uiso calc SR 1 . . H C5 0.7166(4) 0.2500 0.5378(4) 0.0180(7) Uani d S 1 . . C C6 0.6497(4) 0.2500 0.3687(4) 0.0186(7) Uani d S 1 . . C H6 0.5325 0.2500 0.3186 0.022 Uiso calc SR 1 . . H Br3 0.29461(4) 0.2500 -0.05871(4) 0.01974(11) Uani d S 1 . . Br 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 0.01748(19) 0.0247(2) 0.0264(2) 0.000 0.00854(14) 0.000 Br2 0.0254(2) 0.0306(2) 0.0221(2) 0.000 0.01067(14) 0.000 N 0.0181(14) 0.0202(15) 0.0185(13) 0.000 0.0046(11) 0.000 C1 0.0192(16) 0.0145(16) 0.0208(16) 0.000 0.0041(13) 0.000 C2 0.0172(16) 0.0153(16) 0.0221(16) 0.000 0.0054(12) 0.000 C3 0.0172(16) 0.0197(17) 0.0241(17) 0.000 0.0011(13) 0.000 C4 0.0271(18) 0.0172(17) 0.0180(16) 0.000 0.0031(13) 0.000 C5 0.0177(16) 0.0182(16) 0.0193(16) 0.000 0.0071(13) 0.000 C6 0.0183(16) 0.0165(16) 0.0201(16) 0.000 0.0041(13) 0.000 Br3 0.01522(17) 0.02049(19) 0.02266(18) 0.000 0.00412(13) 0.000 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' N N 0.0061 0.0033 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 C1 C2 121.4(3) C6 C1 N 119.0(3) C2 C1 N 119.7(3) C3 C2 C1 119.8(3) C3 C2 Br1 121.3(3) C1 C2 Br1 119.0(3) C2 C3 C4 120.4(3) C3 C4 C5 118.7(3) C6 C5 C4 122.5(3) C6 C5 Br2 118.0(3) C4 C5 Br2 119.5(3) C5 C6 C1 117.3(3) C1 N H01 112(3) C1 N H02 112.8(17) H01 N H02 105(2) C2 C3 H3 119.8 C4 C3 H3 119.8 C3 C4 H4 120.7 C5 C4 H4 120.7 C5 C6 H6 121.4 C1 C6 H6 121.4 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 C2 . 1.898(4) ? Br2 C5 . 1.908(3) ? N C1 . 1.460(4) ? C1 C6 . 1.394(5) ? C1 C2 . 1.394(5) ? C2 C3 . 1.382(5) ? C3 C4 . 1.390(5) ? C4 C5 . 1.391(5) ? C5 C6 . 1.391(5) ? N H01 . 0.93(3) ? N H02 . 0.92(2) ? C3 H3 . 0.9500 ? C4 H4 . 0.9500 ? C6 H6 . 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 N H01 Br3 . 0.93(3) 2.32(3) 3.240(3) 173(4) N H02 Br3 3_655 0.92(2) 2.54(3) 3.2936(6) 139(2) C3 H3 Br3 1_656 0.95 3.11 3.757(4) 126.6 C4 H4 Br3 1_656 0.95 3.06 3.727(4) 128.3