##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-02-10
_journal_date_accepted     2010-02-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      3
_journal_page_first     o664
_journal_page_last     o664
_journal_paper_category     QO
_journal_coeditor_code     TK2628
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
2-Amino-5-bromopyridinium 3-aminobenzoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Madhukar Hemamalini' ?
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Amino-5-bromopyridinium 3-aminobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H6 Br N2 +, C7 H6 N O2 -'
_chemical_formula_sum     'C12 H12 Br N3 O2'
_chemical_formula_iupac     'C5 H6 Br N2 +, C7 H6 N O2 -'
_chemical_formula_weight     309.15
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     10.1650(7)
_cell_length_b     11.0431(7)
_cell_length_c     11.9550(9)
_cell_angle_alpha     90.00
_cell_angle_beta     113.710(2)
_cell_angle_gamma     90.00
_cell_volume     1228.71(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4215
_cell_measurement_theta_min     2.62
_cell_measurement_theta_max     26.79
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'blcok'
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.39
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.671
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     620
_exptl_absorpt_coefficient_mu     3.343
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.3321
_exptl_absorpt_correction_T_max     0.7079
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     15251
_diffrn_reflns_av_R_equivalents     0.0337
_diffrn_reflns_av_sigmaI/netI     0.0312
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3565
_reflns_number_gt     2650
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0586
_refine_ls_R_factor_gt     0.0374
_refine_ls_wR_factor_gt     0.1149
_refine_ls_wR_factor_ref     0.1372
_refine_ls_goodness_of_fit_ref     1.057
_refine_ls_restrained_S_all     1.057
_refine_ls_number_reflns     3565
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0846P)²+0.125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.508
_refine_diff_density_min     -0.542
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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_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 0.0532(2) 0.0605(2) 0.0637(2) -0.01495(12) 0.02867(15) -0.00314(12)
    N1 0.0453(10) 0.0357(10) 0.0354(9) -0.0041(8) 0.0179(8) -0.0056(8)
    N2 0.0630(14) 0.0513(13) 0.0451(11) -0.0075(10) 0.0320(10) -0.0064(10)
    C1 0.0432(11) 0.0364(12) 0.0346(10) 0.0035(9) 0.0165(8) -0.0018(9)
    C2 0.0519(13) 0.0432(13) 0.0391(12) 0.0008(11) 0.0200(10) -0.0102(10)
    C3 0.0454(13) 0.0388(12) 0.0480(13) -0.0018(10) 0.0167(10) -0.0113(10)
    C4 0.0357(11) 0.0374(12) 0.0438(12) -0.0006(8) 0.0168(9) -0.0014(9)
    C5 0.0427(11) 0.0401(13) 0.0356(11) -0.0004(9) 0.0183(9) -0.0031(9)
    O1 0.0679(12) 0.0533(12) 0.0469(10) -0.0214(9) 0.0332(9) -0.0119(8)
    O2 0.0784(13) 0.0500(11) 0.0479(10) -0.0120(9) 0.0376(10) -0.0104(8)
    N3 0.0686(16) 0.0571(16) 0.094(2) -0.0195(13) 0.0496(15) -0.0166(15)
    C6 0.0455(12) 0.0433(13) 0.0412(12) -0.0013(10) 0.0196(9) -0.0006(10)
    C7 0.0490(13) 0.0480(15) 0.0467(13) 0.0038(11) 0.0198(10) -0.0063(11)
    C8 0.0443(13) 0.0380(13) 0.0508(14) 0.0026(10) 0.0137(10) -0.0052(11)
    C9 0.0384(11) 0.0407(13) 0.0546(14) 0.0005(9) 0.0191(10) 0.0024(11)
    C10 0.0430(12) 0.0389(13) 0.0457(12) 0.0005(9) 0.0221(10) 0.0008(10)
    C11 0.0422(11) 0.0334(12) 0.0353(11) 0.0024(8) 0.0139(9) 0.0034(9)
    C12 0.0493(13) 0.0365(12) 0.0336(10) -0.0017(9) 0.0163(9) 0.0021(9)
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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_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_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_
    _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
