#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225393.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_2225393
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-5-bromopyridinium 3-aminobenzoate
;
_journal_coeditor_code           TK2628
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o664
_journal_paper_doi               10.1107/S1600536810006288
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H6 Br N2 +, C7 H6 N O2 -'
_chemical_formula_moiety         'C5 H6 Br N2 +, C7 H6 N O2 -'
_chemical_formula_sum            'C12 H12 Br N3 O2'
_chemical_formula_weight         309.15
_chemical_name_systematic
;
2-Amino-5-bromopyridinium 3-aminobenzoate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.710(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1650(7)
_cell_length_b                   11.0431(7)
_cell_length_c                   11.9550(9)
_cell_measurement_reflns_used    4215
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.62
_cell_volume                     1228.71(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15251
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.343
_exptl_absorpt_correction_T_max  0.7079
_exptl_absorpt_correction_T_min  0.3321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blcok
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.542
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0846P)²+0.125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                2650
_reflns_number_total             3565
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2628.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

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 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225393
_cod_database_fobs_code          2225393
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_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.82844(3) 0.52926(3) 0.04268(3) 0.05749(15) Uani d . 1 . .
N N1 0.5198(2) 0.30649(19) 0.06832(17) 0.0383(4) Uani d . 1 . .
N N2 0.4208(3) 0.2756(2) 0.2082(2) 0.0499(5) Uani d . 1 . .
H H2A 0.3715 0.2168 0.1638 0.060 Uiso calc R 1 . .
H H2B 0.4125 0.2940 0.2749 0.060 Uiso calc R 1 . .
C C1 0.5087(2) 0.3373(2) 0.1739(2) 0.0378(5) Uani d . 1 . .
C C2 0.5959(3) 0.4328(3) 0.2429(2) 0.0442(5) Uani d . 1 . .
H H2 0.5897 0.4569 0.3151 0.053 Uiso calc R 1 . .
C C3 0.6892(3) 0.4899(2) 0.2043(3) 0.0448(5) Uani d . 1 . .
H H3 0.7469 0.5525 0.2502 0.054 Uiso calc R 1 . .
C C4 0.6971(2) 0.4537(2) 0.0954(2) 0.0387(5) Uani d . 1 . .
C C5 0.6125(2) 0.3619(2) 0.0294(2) 0.0387(5) Uani d . 1 . .
H H5 0.6183 0.3370 -0.0428 0.046 Uiso calc R 1 . .
O O1 0.3733(2) 1.13481(18) 0.91776(17) 0.0528(5) Uani d . 1 . .
O O2 0.2423(2) 1.11501(19) 1.02651(17) 0.0549(5) Uani d . 1 . .
N N3 -0.0679(3) 0.7483(2) 0.8606(3) 0.0677(7) Uani d . 1 . .
H H3A -0.1118 0.6865 0.8182 0.081 Uiso calc R 1 . .
H H3B -0.0901 0.7746 0.9185 0.081 Uiso calc R 1 . .
C C6 0.2439(3) 0.9284(2) 0.7774(2) 0.0426(5) Uani d . 1 . .
H H6 0.3115 0.9693 0.7576 0.051 Uiso calc R 1 . .
C C7 0.1775(3) 0.8250(3) 0.7134(2) 0.0477(6) Uani d . 1 . .
H H7 0.2012 0.7963 0.6508 0.057 Uiso calc R 1 . .
C C8 0.0755(3) 0.7644(2) 0.7426(2) 0.0461(6) Uani d . 1 . .
H H8 0.0315 0.6954 0.6992 0.055 Uiso calc R 1 . .
C C9 0.0388(3) 0.8058(2) 0.8355(2) 0.0445(5) Uani d . 1 . .
C C10 0.1058(3) 0.9094(2) 0.9004(2) 0.0412(5) Uani d . 1 . .
H H10 0.0820 0.9380 0.9630 0.049 Uiso calc R 1 . .
C C11 0.2085(3) 0.9701(2) 0.8712(2) 0.0375(5) Uani d . 1 . .
C C12 0.2807(3) 1.0815(2) 0.9441(2) 0.0399(5) Uani d . 1 . .
H H1 0.4617 0.2439 0.0129 0.048 Uiso d R 1 . .
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'
O O 0.0106 0.0060 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 122.5(2) ?
C5 N1 H1 . . 113.7 ?
C1 N1 H1 . . 123.8 ?
C1 N2 H2A . . 120.0 ?
C1 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
N2 C1 N1 . . 118.8(2) ?
N2 C1 C2 . . 123.5(2) ?
N1 C1 C2 . . 117.7(2) ?
C3 C2 C1 . . 120.4(2) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 119.5(2) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C5 C4 C3 . . 119.7(2) ?
C5 C4 Br1 . . 120.33(18) ?
C3 C4 Br1 . . 119.97(19) ?
N1 C5 C4 . . 120.3(2) ?
N1 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C9 N3 H3A . . 120.0 ?
C9 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C11 C6 C7 . . 119.5(2) ?
C11 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C6 C7 C8 . . 120.2(2) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C9 C8 C7 . . 120.8(2) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 N3 . . 120.6(2) ?
C8 C9 C10 . . 119.2(2) ?
N3 C9 C10 . . 120.2(2) ?
C9 C10 C11 . . 120.1(2) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C6 C11 C10 . . 120.3(2) ?
C6 C11 C12 . . 120.8(2) ?
C10 C11 C12 . . 118.9(2) ?
O2 C12 O1 . . 124.2(2) ?
O2 C12 C11 . . 117.4(2) ?
O1 C12 C11 . . 118.4(2) ?
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 C4 . 1.885(2) ?
N1 C5 . 1.353(3) ?
N1 C1 . 1.355(3) ?
N1 H1 . 0.9745 ?
N2 C1 . 1.313(3) ?
N2 H2A . 0.8600 ?
N2 H2B . 0.8600 ?
C1 C2 . 1.410(4) ?
C2 C3 . 1.365(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.395(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.358(3) ?
C5 H5 . 0.9300 ?
O1 C12 . 1.254(3) ?
O2 C12 . 1.252(3) ?
N3 C9 . 1.390(3) ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
C6 C11 . 1.387(3) ?
C6 C7 . 1.389(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.391(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.384(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.396(4) ?
C10 C11 . 1.398(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.515(3) ?
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
_geom_hbond_publ_flag
N1 H1 O1 1_544 0.9800 1.6500 2.626(3) 176.00 yes
N2 H2A O2 1_544 0.8600 1.9900 2.826(3) 165.00 yes
N2 H2B O1 4_575 0.8600 2.0600 2.909(3) 170.00 yes
N3 H3B O2 3_577 0.8600 2.2600 3.028(4) 148.00 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 N2 . . . . -177.0(2) ?
C5 N1 C1 C2 . . . . 1.5(3) ?
N2 C1 C2 C3 . . . . 177.4(3) ?
N1 C1 C2 C3 . . . . -1.0(4) ?
C1 C2 C3 C4 . . . . 0.4(4) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C2 C3 C4 Br1 . . . . -178.6(2) ?
C1 N1 C5 C4 . . . . -1.3(4) ?
C3 C4 C5 N1 . . . . 0.7(4) ?
Br1 C4 C5 N1 . . . . 178.99(18) ?
C11 C6 C7 C8 . . . . 0.5(4) ?
C6 C7 C8 C9 . . . . -0.1(4) ?
C7 C8 C9 N3 . . . . 176.9(3) ?
C7 C8 C9 C10 . . . . -0.2(4) ?
C8 C9 C10 C11 . . . . 0.0(4) ?
N3 C9 C10 C11 . . . . -177.1(3) ?
C7 C6 C11 C10 . . . . -0.7(4) ?
C7 C6 C11 C12 . . . . 179.1(2) ?
C9 C10 C11 C6 . . . . 0.4(4) ?
C9 C10 C11 C12 . . . . -179.3(2) ?
C6 C11 C12 O2 . . . . 179.1(2) ?
C10 C11 C12 O2 . . . . -1.2(3) ?
C6 C11 C12 O1 . . . . -0.2(4) ?
C10 C11 C12 O1 . . . . 179.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656038
