#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202157.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_2202157 loop_ _publ_author_name 'Holmes, Brian T.' 'Padgett, Clifford W.' 'Pennington, William T.' _publ_section_title ; 2-Amino-6-bromopyridinium bromide ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o862 _journal_page_last o864 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C5 H6 Br N2 1+, Br 1-' _chemical_formula_moiety 'C5 H6 Br N2 1+, Br 1-' _chemical_formula_structural 'C5 H6 Br2 N2' _chemical_formula_sum 'C5 H6 Br2 N2' _chemical_formula_weight 253.94 _chemical_name_common '2-amino-6-bromo-pyridinium bromide' _chemical_name_systematic ' 2-amino-6-bromo-pyridinium bromide' _space_group_IT_number 64 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-C 2ac 2' _symmetry_space_group_name_H-M 'C m c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 6.9230(10) _cell_length_b 11.616(2) _cell_length_c 19.413(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.015 _cell_measurement_theta_min 2.5 _cell_volume 1561.1(5) _computing_cell_refinement 'AFC7 Diffractometer Control Software' _computing_data_collection ; AFC7 Diffractometer Control Software (Molecular Structure Corporation/Rigaku, 1997) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation/Rigaku, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku AFC-7' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source '18 kW rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 750 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.10 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 10.300 _exptl_absorpt_correction_T_max 0.291 _exptl_absorpt_correction_T_min 0.082 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(TEXSAN; Molecular Structure Corporation/Rigaku, 1997)' _exptl_crystal_colour Brown _exptl_crystal_density_diffrn 2.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.208 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.801 _refine_diff_density_min -0.808 _refine_ls_extinction_coef 0.0020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 56 _refine_ls_number_reflns 750 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0397 _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^)+(0.0873P)^2^+0.9155P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1062 _refine_ls_wR_factor_ref 0.1162 _reflns_number_gt 580 _reflns_number_total 750 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file om6141.cif _[local]_cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (11 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202157 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, 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 0.0000 0.49775(7) 0.37388(4) 0.0633(4) Uani d S 1 . . Br Br2 0.0000 0.29335(7) 0.17222(3) 0.0522(4) Uani d S 1 . . Br N1 0.0000 0.2665(5) 0.3446(3) 0.0436(14) Uani d S 1 . . N H1 0.0000 0.2937 0.3034 0.052 Uiso calc SR 1 . . H N2 0.0000 0.0845(6) 0.2980(3) 0.067(2) Uani d S 1 . . N H2 0.0000 0.0081 0.3058 0.081 Uiso d SR 1 . . H H3 0.0000 0.0963 0.2522 0.081 Uiso d SR 1 . . H C1 0.0000 0.3411(7) 0.3973(3) 0.0467(17) Uani d S 1 . . C C2 0.0000 0.3044(8) 0.4623(4) 0.062(2) Uani d S 1 . . C H2A 0.0000 0.3561 0.4989 0.074 Uiso calc SR 1 . . H C3 0.0000 0.1852(9) 0.4736(4) 0.070(3) Uani d S 1 . . C H3A 0.0000 0.1572 0.5185 0.084 Uiso calc SR 1 . . H C4 0.0000 0.1105(7) 0.4206(4) 0.060(2) Uani d S 1 . . C H4A 0.0000 0.0317 0.4289 0.071 Uiso calc SR 1 . . H C5 0.0000 0.1523(6) 0.3526(3) 0.0471(18) Uani d S 1 . . C 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 0.1028(8) 0.0406(6) 0.0463(6) 0.000 0.000 -0.0061(4) Br2 0.0752(6) 0.0443(5) 0.0370(5) 0.000 0.000 0.0026(3) N1 0.063(4) 0.036(3) 0.031(3) 0.000 0.000 0.002(3) N2 0.129(6) 0.035(4) 0.038(3) 0.000 0.000 -0.005(3) C1 0.066(5) 0.038(4) 0.036(3) 0.000 0.000 -0.007(3) C2 0.096(6) 0.057(5) 0.032(3) 0.000 0.000 -0.007(4) C3 0.105(7) 0.071(6) 0.034(4) 0.000 0.000 0.012(4) C4 0.098(7) 0.038(4) 0.042(4) 0.000 0.000 0.015(4) C5 0.059(4) 0.041(5) 0.041(4) 0.000 0.000 -0.001(3) 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 C1 . 1.876(8) y N1 C5 . 1.336(10) y N1 C1 . 1.341(8) y N1 H1 . 0.8600 ? N2 C5 . 1.320(9) y N2 H2 . 0.9000 ? N2 H3 . 0.9001 ? C1 C2 . 1.331(10) y C2 C3 . 1.402(12) y C2 H2A . 0.9300 ? C3 C4 . 1.346(11) y C3 H3A . 0.9300 ? C4 C5 . 1.406(9) y C4 H4A . 0.9300 ? Br1 Br2 10_566 3.5484(13) y 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C1 . 123.5(6) y C5 N1 H1 . 118.3 ? C1 N1 H1 . 118.3 ? C5 N2 H2 . 117.0 ? C5 N2 H3 . 134.6 ? H2 N2 H3 . 108.4 ? C2 C1 N1 . 121.1(7) y C2 C1 Br1 . 122.7(6) y N1 C1 Br1 . 116.2(5) y C1 C2 C3 . 117.6(7) y C1 C2 H2A . 121.2 ? C3 C2 H2A . 121.2 ? C4 C3 C2 . 121.1(7) y C4 C3 H3A . 119.4 ? C2 C3 H3A . 119.4 ? C3 C4 C5 . 119.7(8) y C3 C4 H4A . 120.2 ? C5 C4 H4A . 120.2 ? N2 C5 N1 . 119.9(6) y N2 C5 C4 . 123.2(7) y N1 C5 C4 . 116.9(7) y C1 Br1 Br2 10_566 179.43(19) y 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 N2 H3 Br1 10_556 0.90 2.70 3.486(7) 146 N2 H2 Br2 10_556 0.90 2.53 3.431(7) 180 N1 H1 Br2 . 0.86 2.55 3.360(5) 158 C2 H2A Br1 9_566 0.93 3.00 3.923(8) 174 C3 H3A Br2 2 0.93 3.04 3.864(7) 149 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 C5 N1 C1 C2 0.000(3) C5 N1 C1 Br1 180.0 N1 C1 C2 C3 0.000(3) Br1 C1 C2 C3 180.000(2) C1 C2 C3 C4 0.000(3) C2 C3 C4 C5 0.000(3) C1 N1 C5 N2 180.0000(10) C1 N1 C5 C4 0.000(2) C3 C4 C5 N2 180.000(2) C3 C4 C5 N1 0.000(2) _cod_database_fobs_code 2202157