#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206804.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_2206804 loop_ _publ_author_name 'Gustavo Portalone' _publ_section_title ; p-Bromoanilinium chloride ; _journal_coeditor_code TK6250 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3083 _journal_page_last o3085 _journal_paper_doi 10.1107/S160053680502595X _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C6 H7 Br N + , Cl -' _chemical_formula_moiety 'C6 H7 Br N + , Cl -' _chemical_formula_sum 'C6 H7 Br Cl N' _chemical_formula_weight 208.49 _chemical_name_systematic ; p-Bromoaniline hydrochloride ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 105.61(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.629(2) _cell_length_b 9.784(2) _cell_length_c 9.863(9) _cell_measurement_reflns_used 12 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 15 _cell_volume 802.0(8) _computing_cell_refinement XCS _computing_data_collection 'XCS (Colapietro et al., 1992)' _computing_data_reduction XCS _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.659 _diffrn_measured_fraction_theta_max 0.659 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4F' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.710689 _diffrn_reflns_av_R_equivalents 0.011 _diffrn_reflns_av_sigmaI/netI 0.003 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3628 _diffrn_reflns_theta_full 23.5 _diffrn_reflns_theta_max 23.5 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 5 _diffrn_standards_interval_time 33 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 5.372 _exptl_absorpt_correction_T_max 0.450 _exptl_absorpt_correction_T_min 0.396 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.57 _refine_diff_density_min -0.56 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.10 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 82 _refine_ls_number_reflns 781 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.10 _refine_ls_R_factor_all 0.030 _refine_ls_R_factor_gt 0.028 _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^)+(0.0331P)^2^+2.5739P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.071 _refine_ls_wR_factor_ref 0.072 _reflns_number_gt 781 _reflns_number_total 1113 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk6250.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2206804 _cod_database_fobs_code 2206804 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_occupancy _atom_site_type_symbol Br1 0.19329(7) 0.03645(7) 0.23311(6) 0.0576(2) Uani d 1 Br Cl1 -0.58919(15) 0.10949(14) -0.33157(14) 0.0387(3) Uani d 1 Cl N1 -0.4405(5) 0.3035(4) -0.0757(4) 0.0344(10) Uani d 1 N C1 -0.2878(6) 0.2405(5) -0.0004(5) 0.0332(12) Uani d 1 C C2 -0.1458(7) 0.2974(5) -0.0100(6) 0.0410(13) Uani d 1 C C3 -0.0016(6) 0.2370(6) 0.0610(6) 0.0449(14) Uani d 1 C C4 -0.0036(6) 0.1205(6) 0.1385(5) 0.0373(13) Uani d 1 C C5 -0.1465(7) 0.0654(5) 0.1464(5) 0.0430(14) Uani d 1 C C6 -0.2902(6) 0.1250(6) 0.0776(5) 0.0406(13) Uani d 1 C H2 -0.1498 0.3791 -0.0588 0.049 Uiso d 1 H H3 0.0876 0.2665 0.0544 0.055 Uiso d 1 H H5 -0.1501 -0.0052 0.1982 0.027 Uiso d 1 H H6 -0.3976 0.0821 0.0791 0.027 Uiso d 1 H H11 -0.5027 0.2471 -0.1450 0.041 Uiso d 1 H H12 -0.5017 0.3217 -0.0230 0.041 Uiso d 1 H H13 -0.4276 0.3826 -0.1075 0.041 Uiso d 1 H 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 0.0492(4) 0.0590(4) 0.0538(4) 0.0071(3) -0.0050(3) 0.0050(3) Cl1 0.0385(7) 0.0376(7) 0.0420(7) -0.0024(6) 0.0145(6) -0.0050(6) N1 0.037(2) 0.032(2) 0.034(2) -0.001(2) 0.0097(19) -0.002(2) C1 0.043(3) 0.031(3) 0.024(2) 0.000(2) 0.007(2) -0.004(2) C2 0.049(3) 0.036(3) 0.041(3) -0.002(3) 0.017(3) 0.007(2) C3 0.033(3) 0.052(4) 0.050(3) -0.003(3) 0.011(3) 0.002(3) C4 0.035(3) 0.043(3) 0.032(3) 0.004(3) 0.005(2) -0.004(3) C5 0.058(4) 0.037(3) 0.036(3) 0.004(3) 0.014(3) 0.010(2) C6 0.040(3) 0.043(3) 0.041(3) -0.006(3) 0.014(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 Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 N1 H11 112.7 ? C1 N1 H12 113.5 ? H11 N1 H12 104.0 ? C1 N1 H13 112.3 ? H11 N1 H13 112.1 ? H12 N1 H13 101.4 ? N1 C1 C2 119.5(5) yes N1 C1 C6 119.0(5) yes C2 C1 C6 121.5(5) yes C1 C2 C3 119.3(5) yes C1 C2 H2 118.4 ? C3 C2 H2 122.2 ? C2 C3 C4 119.4(5) yes C4 C3 H3 118.4 ? C2 C3 H3 122.1 ? Br1 C4 C5 120.3(4) yes Br1 C4 C3 119.4(4) yes C3 C4 C5 120.3(5) yes C4 C5 C6 120.9(5) yes C4 C5 H5 121.7 ? C6 C5 H5 117.4 ? C1 C6 C5 118.7(5) yes C1 C6 H6 119.9 ? C5 C6 H6 121.4 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C4 1.892(5) yes N1 C1 1.463(6) yes N1 H11 0.9292 ? N1 H12 0.8536 ? N1 H13 0.8538 ? C1 C2 1.372(7) yes C1 C6 1.371(7) yes C2 C3 1.385(8) yes C2 H2 0.9280 ? C3 C4 1.376(8) yes C3 H3 0.8407 ? C4 C5 1.367(8) yes C5 C6 1.373(7) yes C5 H5 0.8647 ? C6 H6 1.0211 ? 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 N1 H11 Cl1 . 0.93 2.24 3.143(5) 164 N1 H12 Cl1 4_566 0.85 2.31 3.136(5) 162 N1 H13 Cl1 2_454 0.85 2.31 3.161(4) 171 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 C6 C1 C2 C3 -0.1(8) N1 C1 C2 C3 -179.7(5) C1 C2 C3 C4 0.6(8) C2 C3 C4 C5 -0.5(8) C2 C3 C4 Br1 179.0(4) C3 C4 C5 C6 -0.2(8) Br1 C4 C5 C6 -179.7(4) C2 C1 C6 C5 -0.5(8) N1 C1 C6 C5 179.1(5) C4 C5 C6 C1 0.7(8)