#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2225365.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_2225365
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-5-bromopyridine--benzoic acid (1/1)
;
_journal_coeditor_code           RZ2420
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o663
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H5 Br N2, C7 H6 O2'
_chemical_formula_moiety         'C5 H5 Br N2, C7 H6 O2'
_chemical_formula_sum            'C12 H11 Br N2 O2'
_chemical_formula_weight         295.14
_chemical_name_systematic
;
2-Amino-5-bromopyridine--benzoic acid (1/1)
;
_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                 97.016(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.5614(16)
_cell_length_b                   5.1769(5)
_cell_length_c                   12.3613(11)
_cell_measurement_reflns_used    3648
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.96
_cell_measurement_theta_min      3.76
_cell_volume                     1178.91(19)
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w 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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19825
_diffrn_reflns_theta_full        35.91
_diffrn_reflns_theta_max         35.91
_diffrn_reflns_theta_min         3.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.477
_exptl_absorpt_correction_T_max  0.7879
_exptl_absorpt_correction_T_min  0.2275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.248
_refine_diff_density_min         -0.499
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0450
_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/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                3709
_reflns_number_total             5495
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    rz2420.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2225365
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
Br Br1 0.470134(11) 0.30630(5) 0.886018(18) 0.02683(8) Uani d . 1
N N1 0.31375(10) -0.1799(3) 0.73265(14) 0.0191(3) Uani d . 1
N N2 0.25884(11) -0.2217(4) 0.55605(15) 0.0252(4) Uani d . 1
H H2A 0.2364 -0.3558 0.5758 0.030 Uiso calc R 1
H H2B 0.2519 -0.1704 0.4894 0.030 Uiso calc R 1
C C1 0.30452(10) -0.0928(4) 0.62906(16) 0.0188(3) Uani d . 1
C C2 0.34283(11) 0.1260(4) 0.59759(17) 0.0214(4) Uani d . 1
H H2 0.3351 0.1861 0.5262 0.026 Uiso calc R 1
C C3 0.39160(12) 0.2490(4) 0.67336(19) 0.0231(4) Uani d . 1
H H3 0.4172 0.3930 0.6543 0.028 Uiso calc R 1
C C4 0.40175(11) 0.1516(4) 0.78013(17) 0.0210(4) Uani d . 1
C C5 0.36211(11) -0.0591(4) 0.80675(16) 0.0206(4) Uani d . 1
H H5 0.3688 -0.1204 0.8780 0.025 Uiso calc R 1
O O1 0.23842(7) 0.4732(3) 0.82571(10) 0.0188(3) Uani d . 1
H H1 0.2668 0.5550 0.7929 0.028 Uiso calc R 1
O O2 0.19345(9) 0.3546(3) 0.65709(11) 0.0217(3) Uani d . 1
C C7 0.13808(11) 0.1436(4) 0.91317(15) 0.0186(4) Uani d . 1
H H7 0.1616 0.2660 0.9600 0.022 Uiso calc R 1
C C8 0.09178(11) -0.0370(4) 0.95201(16) 0.0215(4) Uani d . 1
H H8 0.0842 -0.0341 1.0250 0.026 Uiso calc R 1
C C9 0.05710(11) -0.2199(4) 0.88304(18) 0.0215(4) Uani d . 1
H H9 0.0265 -0.3401 0.9097 0.026 Uiso calc R 1
C C10 0.06795(12) -0.2244(4) 0.77347(18) 0.0217(4) Uani d . 1
H H10 0.0446 -0.3477 0.7269 0.026 Uiso calc R 1
C C11 0.11352(10) -0.0450(4) 0.73404(15) 0.0191(3) Uani d . 1
H H11 0.1205 -0.0473 0.6608 0.023 Uiso calc R 1
C C12 0.14884(10) 0.1389(4) 0.80347(15) 0.0163(3) Uani d . 1
C C13 0.19580(10) 0.3321(4) 0.75609(15) 0.0163(3) Uani d . 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 0.02372(11) 0.02522(13) 0.03212(12) -0.00568(8) 0.00565(8) -0.00818(9)
N1 0.0222(7) 0.0160(8) 0.0196(7) -0.0029(6) 0.0045(6) -0.0009(6)
N2 0.0331(9) 0.0235(9) 0.0182(7) -0.0074(8) 0.0000(7) 0.0037(7)
C1 0.0201(8) 0.0154(8) 0.0212(8) 0.0012(7) 0.0041(7) 0.0016(7)
C2 0.0221(8) 0.0194(9) 0.0239(8) 0.0008(7) 0.0076(7) 0.0056(8)
C3 0.0208(8) 0.0181(9) 0.0320(10) -0.0006(7) 0.0097(8) 0.0032(8)
C4 0.0191(8) 0.0176(9) 0.0268(9) -0.0005(7) 0.0053(7) -0.0045(7)
C5 0.0220(8) 0.0194(9) 0.0208(8) -0.0005(8) 0.0043(7) 0.0011(7)
O1 0.0209(6) 0.0193(7) 0.0159(6) -0.0052(6) 0.0013(5) 0.0003(5)
O2 0.0310(7) 0.0199(7) 0.0145(5) -0.0032(6) 0.0043(5) 0.0000(5)
C7 0.0219(8) 0.0183(9) 0.0153(7) -0.0007(7) 0.0010(6) 0.0010(7)
C8 0.0225(8) 0.0226(10) 0.0199(8) -0.0018(8) 0.0041(7) 0.0052(8)
C9 0.0207(8) 0.0165(9) 0.0277(9) -0.0007(7) 0.0043(7) 0.0054(8)
C10 0.0218(8) 0.0168(9) 0.0266(9) -0.0009(7) 0.0027(7) -0.0033(8)
C11 0.0214(8) 0.0171(9) 0.0190(8) 0.0013(7) 0.0033(6) -0.0029(7)
C12 0.0176(7) 0.0141(8) 0.0173(7) 0.0018(6) 0.0031(6) 0.0008(6)
C13 0.0191(8) 0.0143(8) 0.0158(7) 0.0022(7) 0.0028(6) 0.0002(6)
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
C1 N1 C5 118.98(18)
C1 N2 H2A 120.0
C1 N2 H2B 120.0
H2A N2 H2B 120.0
N2 C1 N1 118.04(19)
N2 C1 C2 120.74(19)
N1 C1 C2 121.21(19)
C3 C2 C1 119.56(19)
C3 C2 H2 120.2
C1 C2 H2 120.2
C2 C3 C4 118.38(19)
C2 C3 H3 120.8
C4 C3 H3 120.8
C5 C4 C3 119.6(2)
C5 C4 Br1 120.26(16)
C3 C4 Br1 120.10(16)
N1 C5 C4 122.22(19)
N1 C5 H5 118.9
C4 C5 H5 118.9
C13 O1 H1 109.5
C8 C7 C12 119.37(19)
C8 C7 H7 120.3
C12 C7 H7 120.3
C9 C8 C7 120.53(18)
C9 C8 H8 119.7
C7 C8 H8 119.7
C8 C9 C10 120.01(19)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 119.9(2)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.26(18)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C7 119.95(18)
C11 C12 C13 118.04(16)
C7 C12 C13 121.98(18)
O2 C13 O1 123.04(18)
O2 C13 C12 120.31(18)
O1 C13 C12 116.65(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.887(2)
N1 C1 1.349(3)
N1 C5 1.355(3)
N2 C1 1.339(3)
N2 H2A 0.8600
N2 H2B 0.8600
C1 C2 1.417(3)
C2 C3 1.377(3)
C2 H2 0.9300
C3 C4 1.404(3)
C3 H3 0.9300
C4 C5 1.378(3)
C5 H5 0.9300
O1 C13 1.317(2)
O1 H1 0.8200
O2 C13 1.225(2)
C7 C8 1.394(3)
C7 C12 1.395(2)
C7 H7 0.9300
C8 C9 1.380(3)
C8 H8 0.9300
C9 C10 1.394(3)
C9 H9 0.9300
C10 C11 1.384(3)
C10 H10 0.9300
C11 C12 1.391(3)
C11 H11 0.9300
C12 C13 1.493(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
O1 H1 N1 1_565 0.8200 1.8300 2.626(2) 162.00 yes
N2 H2A O2 1_545 0.8600 2.0200 2.866(3) 167.00 yes
N2 H2B O1 4_565 0.8600 2.2500 3.105(2) 171.00 yes
C7 H7 O2 4_566 0.9300 2.5100 3.064(2) 118.00 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
C5 N1 C1 N2 177.14(19)
C5 N1 C1 C2 -1.8(3)
N2 C1 C2 C3 -177.5(2)
N1 C1 C2 C3 1.4(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -1.2(3)
C2 C3 C4 Br1 178.02(16)
C1 N1 C5 C4 0.6(3)
C3 C4 C5 N1 0.9(3)
Br1 C4 C5 N1 -178.36(15)
C12 C7 C8 C9 0.3(3)
C7 C8 C9 C10 -0.3(3)
C8 C9 C10 C11 -0.1(3)
C9 C10 C11 C12 0.4(3)
C10 C11 C12 C7 -0.3(3)
C10 C11 C12 C13 -178.42(19)
C8 C7 C12 C11 0.0(3)
C8 C7 C12 C13 177.99(19)
C11 C12 C13 O2 12.0(3)
C7 C12 C13 O2 -166.00(19)
C11 C12 C13 O1 -168.26(18)
C7 C12 C13 O1 13.7(3)