#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218485.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_2218485
loop_
_publ_author_name
'Shen, Hong'
'Nie, Jing-Jing'
'Xu, Duan-Jun'
_publ_section_title
;
 2-Amino-4-methylpyridinium 4-aminobenzoate
;
_journal_coeditor_code           NG2457
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1129
_journal_paper_doi               10.1107/S1600536808014839
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C6 H9 N2 +, C7 H6 N O2 -'
_chemical_formula_moiety         'C6 H9 N2 +, C7 H6 N O2 -'
_chemical_formula_sum            'C13 H15 N3 O2'
_chemical_formula_weight         245.28
_chemical_name_systematic
;
2-Amino-4-methylpyridinium 4-aminobenzoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5734(14)
_cell_length_b                   8.8154(16)
_cell_length_c                   25.374(5)
_cell_measurement_reflns_used    2654
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.0
_cell_volume                     1246.7(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14099
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.123
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0373
_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)+(0.0449P)²+0.1505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                1126
_reflns_number_total             1451
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2457.cif
_cod_data_source_block           I
_cod_original_cell_volume        1246.6(5)
_cod_database_code               2218485
_cod_database_fobs_code          2218485
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
N N1 -0.5107(5) 0.2323(3) 0.74214(9) 0.0710(7) Uani d . 1
H H1A -0.4459 0.1947 0.7712 0.106 Uiso d R 1
H H1B -0.6362 0.1981 0.7267 0.106 Uiso d R 1
N N2 0.5736(4) 0.8834(2) 0.61196(7) 0.0520(6) Uani d . 1
H H2N 0.4548 0.8231 0.6256 0.078 Uiso d R 1
N N3 0.4308(5) 0.8308(3) 0.52906(8) 0.0660(7) Uani d . 1
H H3A 0.4443 0.8528 0.4934 0.099 Uiso d R 1
H H3B 0.3098 0.7766 0.5454 0.099 Uiso d R 1
O O1 0.0737(4) 0.6432(2) 0.57815(6) 0.0692(6) Uani d . 1
O O2 0.2584(3) 0.6999(2) 0.65310(6) 0.0562(5) Uani d . 1
C C1 -0.0644(4) 0.5269(3) 0.65687(9) 0.0451(6) Uani d . 1
C C2 -0.0117(4) 0.4843(3) 0.70832(9) 0.0497(6) Uani d . 1
H H2 0.1249 0.5233 0.7244 0.060 Uiso calc R 1
C C3 -0.1565(5) 0.3857(3) 0.73617(9) 0.0523(7) Uani d . 1
H H3 -0.1139 0.3568 0.7702 0.063 Uiso calc R 1
C C4 -0.3654(5) 0.3295(3) 0.71361(9) 0.0488(6) Uani d . 1
C C5 -0.4210(5) 0.3741(3) 0.66250(10) 0.0581(7) Uani d . 1
H H5 -0.5612 0.3388 0.6468 0.070 Uiso calc R 1
C C6 -0.2727(5) 0.4694(3) 0.63474(10) 0.0550(7) Uani d . 1
H H6 -0.3129 0.4960 0.6004 0.066 Uiso calc R 1
C C7 0.0980(5) 0.6303(3) 0.62688(9) 0.0479(6) Uani d . 1
C C8 0.5886(5) 0.9037(3) 0.55940(9) 0.0482(6) Uani d . 1
C C9 0.7670(5) 1.0014(3) 0.53990(10) 0.0520(6) Uani d . 1
H H9 0.7815 1.0156 0.5037 0.062 Uiso calc R 1
C C10 0.9189(5) 1.0757(3) 0.57306(10) 0.0551(7) Uani d . 1
C C11 0.8960(6) 1.0501(3) 0.62760(11) 0.0668(8) Uani d . 1
H H11 0.9977 1.0989 0.6512 0.080 Uiso calc R 1
C C12 0.7262(6) 0.9547(3) 0.64526(10) 0.0636(8) Uani d . 1
H H12 0.7131 0.9372 0.6813 0.076 Uiso calc R 1
C C13 1.1031(6) 1.1849(3) 0.55251(12) 0.0742(8) Uani d . 1
H H13A 1.1123 1.1766 0.5148 0.111 Uiso calc R 1
H H13B 1.2567 1.1615 0.5676 0.111 Uiso calc R 1
H H13C 1.0582 1.2865 0.5619 0.111 Uiso calc 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C4 N1 H1A 115.4
C4 N1 H1B 117.1
H1A N1 H1B 125.7
C8 N2 C12 121.1(2)
C8 N2 H2N 119.7
C12 N2 H2N 119.2
C8 N3 H3A 114.1
C8 N3 H3B 118.1
H3A N3 H3B 127.2
C6 C1 C2 117.3(2)
C6 C1 C7 121.7(2)
C2 C1 C7 121.0(2)
C3 C2 C1 121.8(2)
C3 C2 H2 119.1
C1 C2 H2 119.1
C2 C3 C4 120.2(2)
C2 C3 H3 119.9
C4 C3 H3 119.9
N1 C4 C3 119.7(2)
N1 C4 C5 122.2(2)
C3 C4 C5 118.1(2)
C6 C5 C4 121.1(3)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 121.4(2)
C5 C6 H6 119.3
C1 C6 H6 119.3
O1 C7 O2 123.4(2)
O1 C7 C1 119.6(2)
O2 C7 C1 117.0(2)
N3 C8 N2 117.8(2)
N3 C8 C9 124.0(2)
N2 C8 C9 118.3(2)
C10 C9 C8 121.1(2)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 118.3(3)
C9 C10 C13 121.3(2)
C11 C10 C13 120.4(3)
C12 C11 C10 119.5(3)
C12 C11 H11 120.3
C10 C11 H11 120.3
C11 C12 N2 121.7(2)
C11 C12 H12 119.1
N2 C12 H12 119.1
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 1.384(3) ?
N1 H1A 0.8846 ?
N1 H1B 0.8568 ?
N2 C8 1.348(3) ?
N2 C12 1.354(3) ?
N2 H2N 0.9167 ?
N3 C8 1.334(3) ?
N3 H3A 0.9287 ?
N3 H3B 0.9252 ?
O1 C7 1.249(3) y
O2 C7 1.272(3) y
C1 C6 1.385(4) ?
C1 C2 1.390(3) ?
C1 C7 1.494(3) ?
C2 C3 1.381(3) ?
C2 H2 0.9300 ?
C3 C4 1.389(3) ?
C3 H3 0.9300 ?
C4 C5 1.390(3) ?
C5 C6 1.373(4) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C8 C9 1.405(4) ?
C9 C10 1.361(4) ?
C9 H9 0.9300 ?
C10 C11 1.408(4) ?
C10 C13 1.501(4) ?
C11 C12 1.343(4) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
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 H1A O2 4_546 0.89 2.19 3.021(3) 157 y
N2 H2N O2 . 0.92 1.69 2.606(3) 174 y
N3 H3A O1 3_566 0.93 1.95 2.844(3) 160 y
N3 H3B O1 . 0.92 1.95 2.872(3) 174 y
C3 H3 O2 4_546 0.93 2.52 3.301(3) 142 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655508
