#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225685.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_2225685
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-5-methylpyridinium 4-hydroxybenzoate
;
_journal_coeditor_code           RZ2424
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o936
_journal_page_last               o937
_journal_paper_doi               10.1107/S1600536810009396
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H9 N2 +, C7 H5 O3 -'
_chemical_formula_moiety         'C6 H9 N2 +, C7 H5 O3 -'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_name_systematic
;
2-Amino-5-methylpyridinium 4-hydroxybenzoate
;
_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                 108.3970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9562(6)
_cell_length_b                   8.7876(4)
_cell_length_c                   11.3276(5)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      36.22
_cell_measurement_theta_min      6.53
_cell_volume                     1223.78(10)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20102
_diffrn_reflns_theta_full        35.00
_diffrn_reflns_theta_max         35.00
_diffrn_reflns_theta_min         6.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blcok
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0394
_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/[σ²(Fo²)+(0.0859P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                4662
_reflns_number_total             5326
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2424.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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225685
_cod_database_fobs_code          2225685
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
O O1 -0.07705(4) 1.29454(6) 0.44060(5) 0.01923(12) Uani d . 1 . .
O O2 0.23879(4) 0.85691(6) 0.26656(5) 0.01752(11) Uani d . 1 . .
O O3 0.34273(4) 0.90704(7) 0.45979(5) 0.02001(12) Uani d . 1 . .
C C7 0.17088(6) 1.07237(8) 0.50635(6) 0.01751(13) Uani d . 1 . .
C C8 0.08861(6) 1.16244(9) 0.52300(6) 0.01815(13) Uani d . 1 . .
C C9 0.00128(5) 1.20628(7) 0.42014(6) 0.01493(12) Uani d . 1 . .
C C10 -0.00280(5) 1.15864(8) 0.30079(6) 0.01519(12) Uani d . 1 . .
C C11 0.07897(5) 1.06554(8) 0.28576(6) 0.01482(12) Uani d . 1 . .
C C12 0.16699(5) 1.02150(7) 0.38786(6) 0.01410(11) Uani d . 1 . .
C C13 0.25438(5) 0.92210(8) 0.37051(6) 0.01435(12) Uani d . 1 . .
N N1 0.48836(5) 0.71343(7) 0.42194(5) 0.01544(11) Uani d . 1 . .
N N2 0.39201(5) 0.66496(8) 0.21647(6) 0.01851(12) Uani d . 1 . .
C C1 0.48185(5) 0.64504(7) 0.31296(6) 0.01461(12) Uani d . 1 . .
C C2 0.57195(6) 0.55617(8) 0.30846(6) 0.01732(13) Uani d . 1 . .
C C3 0.65954(6) 0.53911(8) 0.41374(7) 0.01848(13) Uani d . 1 . .
C C4 0.66298(5) 0.60787(8) 0.52806(6) 0.01614(12) Uani d . 1 . .
C C5 0.57535(5) 0.69542(8) 0.52670(6) 0.01641(12) Uani d . 1 . .
C C6 0.75785(6) 0.58625(10) 0.64330(7) 0.02191(14) Uani d . 1 . .
H H2A 0.5718(11) 0.5103(16) 0.2257(12) 0.027(3) Uiso d . 1 . .
H H3A 0.7256(12) 0.4762(18) 0.4148(13) 0.034(3) Uiso d . 1 . .
H H5A 0.5712(11) 0.7533(16) 0.5988(13) 0.027(3) Uiso d . 1 . .
H H6A 0.7657(12) 0.4804(19) 0.6662(14) 0.039(4) Uiso d . 1 . .
H H6B 0.8244(13) 0.6124(18) 0.6294(14) 0.038(4) Uiso d . 1 . .
H H6C 0.7483(13) 0.6507(19) 0.7124(16) 0.040(4) Uiso d . 1 . .
H H7A 0.2334(11) 1.0425(17) 0.5794(13) 0.029(3) Uiso d . 1 . .
H H8A 0.0899(13) 1.2010(18) 0.6068(15) 0.038(4) Uiso d . 1 . .
H H10A -0.0628(12) 1.1968(16) 0.2289(14) 0.030(3) Uiso d . 1 . .
H H11A 0.0758(10) 1.0333(15) 0.2012(11) 0.021(3) Uiso d . 1 . .
H H101 -0.1257(15) 1.3172(19) 0.3673(16) 0.045(4) Uiso d . 1 . .
H H1N1 0.4304(13) 0.7749(19) 0.4310(14) 0.038(4) Uiso d . 1 . .
H H1N2 0.3819(12) 0.6231(15) 0.1407(13) 0.028(3) Uiso d . 1 . .
H H2N2 0.3394(11) 0.7245(15) 0.2326(12) 0.025(3) Uiso d . 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'
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
C9 O1 H101 . . 108.4(11) ?
C8 C7 C12 . . 121.04(6) ?
C8 C7 H7A . . 119.8(8) ?
C12 C7 H7A . . 119.1(8) ?
C7 C8 C9 . . 119.89(6) ?
C7 C8 H8A . . 122.5(9) ?
C9 C8 H8A . . 117.6(9) ?
O1 C9 C8 . . 117.93(6) ?
O1 C9 C10 . . 122.31(6) ?
C8 C9 C10 . . 119.76(6) ?
C11 C10 C9 . . 119.73(6) ?
C11 C10 H10A . . 122.0(9) ?
C9 C10 H10A . . 118.2(9) ?
C10 C11 C12 . . 121.02(6) ?
C10 C11 H11A . . 119.2(7) ?
C12 C11 H11A . . 119.7(7) ?
C11 C12 C7 . . 118.53(6) ?
C11 C12 C13 . . 120.53(6) ?
C7 C12 C13 . . 120.94(6) ?
O2 C13 O3 . . 122.08(6) ?
O2 C13 C12 . . 118.84(6) ?
O3 C13 C12 . . 119.08(6) ?
C1 N1 C5 . . 122.65(6) ?
C1 N1 H1N1 . . 121.6(9) ?
C5 N1 H1N1 . . 115.7(9) ?
C1 N2 H1N2 . . 123.5(9) ?
C1 N2 H2N2 . . 114.9(8) ?
H1N2 N2 H2N2 . . 121.6(12) ?
N2 C1 N1 . . 118.50(6) ?
N2 C1 C2 . . 123.94(6) ?
N1 C1 C2 . . 117.56(6) ?
C3 C2 C1 . . 119.59(6) ?
C3 C2 H2A . . 121.2(8) ?
C1 C2 H2A . . 119.2(8) ?
C2 C3 C4 . . 121.81(6) ?
C2 C3 H3A . . 122.2(8) ?
C4 C3 H3A . . 116.0(8) ?
C5 C4 C3 . . 116.31(6) ?
C5 C4 C6 . . 122.13(6) ?
C3 C4 C6 . . 121.56(6) ?
N1 C5 C4 . . 122.03(6) ?
N1 C5 H5A . . 114.7(8) ?
C4 C5 H5A . . 123.2(8) ?
C4 C6 H6A . . 110.2(9) ?
C4 C6 H6B . . 111.2(9) ?
H6A C6 H6B . . 104.7(13) ?
C4 C6 H6C . . 109.8(9) ?
H6A C6 H6C . . 111.4(13) ?
H6B C6 H6C . . 109.5(13) ?
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
O1 C9 . 1.3541(8) ?
O1 H101 . 0.893(18) ?
O2 C13 . 1.2670(8) ?
O3 C13 . 1.2728(8) ?
C7 C8 . 1.3875(9) ?
C7 C12 . 1.4004(9) ?
C7 H7A . 0.993(14) ?
C8 C9 . 1.3978(9) ?
C8 H8A . 1.003(15) ?
C9 C10 . 1.4003(9) ?
C10 C11 . 1.3909(9) ?
C10 H10A . 0.990(15) ?
C11 C12 . 1.3984(9) ?
C11 H11A . 0.987(12) ?
C12 C13 . 1.4912(9) ?
N1 C1 . 1.3516(8) ?
N1 C5 . 1.3636(9) ?
N1 H1N1 . 0.956(16) ?
N2 C1 . 1.3331(9) ?
N2 H1N2 . 0.904(14) ?
N2 H2N2 . 0.922(14) ?
C1 C2 . 1.4187(9) ?
C2 C3 . 1.3705(10) ?
C2 H2A . 1.020(13) ?
C3 C4 . 1.4169(10) ?
C3 H3A . 1.016(15) ?
C4 C5 . 1.3675(9) ?
C4 C6 . 1.4962(10) ?
C5 H5A . 0.978(14) ?
C6 H6A . 0.963(16) ?
C6 H6B . 0.952(16) ?
C6 H6C . 1.006(17) ?
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 H1N1 O3 . 0.957(17) 1.726(17) 2.6738(9) 170.4(15) yes
N2 H1N2 O3 4_575 0.905(14) 1.967(14) 2.8443(9) 162.9(13) yes
N2 H2N2 O2 . 0.922(14) 1.876(14) 2.7962(9) 176.1(13) yes
O1 H101 O2 2_555 0.892(18) 1.779(18) 2.6635(8) 170.7(19) yes
C3 H3A O2 2_645 1.016(16) 2.476(15) 3.1887(9) 126.7(10) 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
C12 C7 C8 C9 . . . . -1.35(11) ?
C7 C8 C9 O1 . . . . -179.81(6) ?
C7 C8 C9 C10 . . . . 0.17(11) ?
O1 C9 C10 C11 . . . . -178.73(6) ?
C8 C9 C10 C11 . . . . 1.29(10) ?
C9 C10 C11 C12 . . . . -1.60(10) ?
C10 C11 C12 C7 . . . . 0.44(10) ?
C10 C11 C12 C13 . . . . -179.77(6) ?
C8 C7 C12 C11 . . . . 1.05(11) ?
C8 C7 C12 C13 . . . . -178.74(6) ?
C11 C12 C13 O2 . . . . -12.12(10) ?
C7 C12 C13 O2 . . . . 167.67(6) ?
C11 C12 C13 O3 . . . . 166.93(6) ?
C7 C12 C13 O3 . . . . -13.29(10) ?
C5 N1 C1 N2 . . . . 177.71(6) ?
C5 N1 C1 C2 . . . . -2.43(10) ?
N2 C1 C2 C3 . . . . -178.20(7) ?
N1 C1 C2 C3 . . . . 1.94(10) ?
C1 C2 C3 C4 . . . . 0.08(11) ?
C2 C3 C4 C5 . . . . -1.66(11) ?
C2 C3 C4 C6 . . . . 178.74(7) ?
C1 N1 C5 C4 . . . . 0.83(11) ?
C3 C4 C5 N1 . . . . 1.25(10) ?
C6 C4 C5 N1 . . . . -179.16(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656059
