#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/71/2237179.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_2237179
loop_
_publ_author_name
'Thanigaimani, Kaliyaperumal'
'Farhadikoutenaei, Abbas'
'Arshad, Suhana'
'Razak, Ibrahim Abdul'
_publ_section_title
;
 2-Amino-5-methylpyridinium 4-chlorobenzoate
;
_journal_coeditor_code           IS5231
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o134
_journal_page_last               o135
_journal_paper_doi               10.1107/S1600536812051021
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H9 N2 +, C7 H4 Cl O2 -'
_chemical_formula_moiety         'C6 H9 N2 +, C7 H4 Cl O2 -'
_chemical_formula_sum            'C13 H13 Cl N2 O2'
_chemical_formula_weight         264.70
_chemical_name_systematic
;
2-Amino-5-methylpyridinium 4-chlorobenzoate
;
_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                 102.335(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8510(6)
_cell_length_b                   10.7707(8)
_cell_length_c                   12.2123(7)
_cell_measurement_reflns_used    3497
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.55
_cell_volume                     1265.84(14)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17572
_diffrn_reflns_theta_full        32.76
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         2.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9630
_exptl_absorpt_correction_T_min  0.8762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0608P)²+0.1513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                2976
_reflns_number_total             4628
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5231.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237179
_cod_database_fobs_code          2237179
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_symmetry_multiplicity
Cl Cl1 -0.02173(5) 0.82984(4) 0.23669(4) 0.07093(17) Uani d . 1 1
O O1 0.41482(11) 0.36071(10) 0.43150(8) 0.0468(2) Uani d . 1 1
O O2 0.29316(12) 0.37788(10) 0.56405(8) 0.0521(3) Uani d . 1 1
N N1 0.54982(12) 0.32374(10) 0.06443(9) 0.0384(2) Uani d . 1 1
N N2 0.44920(16) 0.28252(14) 0.21480(12) 0.0534(3) Uani d . 1 1
C C1 0.53584(14) 0.34947(12) 0.16960(11) 0.0393(3) Uani d . 1 1
C C2 0.61705(15) 0.44688(14) 0.22692(12) 0.0462(3) Uani d . 1 1
H H2A 0.6104 0.4672 0.2996 0.055 Uiso calc R 1 1
C C3 0.70468(15) 0.51067(14) 0.17600(13) 0.0490(3) Uani d . 1 1
H H3A 0.7581 0.5743 0.2148 0.059 Uiso calc R 1 1
C C4 0.71723(14) 0.48309(13) 0.06545(12) 0.0452(3) Uani d . 1 1
C C5 0.63774(14) 0.38868(13) 0.01390(11) 0.0416(3) Uani d . 1 1
H H5A 0.6435 0.3675 -0.0588 0.050 Uiso calc R 1 1
C C6 0.81460(18) 0.55543(18) 0.01020(17) 0.0643(4) Uani d . 1 1
H H6A 0.8137 0.5209 -0.0624 0.096 Uiso calc R 1 1
H H6B 0.9070 0.5510 0.0555 0.096 Uiso calc R 1 1
H H6C 0.7853 0.6406 0.0022 0.096 Uiso calc R 1 1
C C7 0.14475(15) 0.57790(14) 0.46421(12) 0.0449(3) Uani d . 1 1
H H7A 0.1323 0.5510 0.5338 0.054 Uiso calc R 1 1
C C8 0.06266(16) 0.67279(15) 0.40995(14) 0.0530(4) Uani d . 1 1
H H8A -0.0053 0.7091 0.4420 0.064 Uiso calc R 1 1
C C9 0.08322(14) 0.71276(13) 0.30744(12) 0.0452(3) Uani d . 1 1
C C10 0.18420(16) 0.66134(13) 0.25949(12) 0.0452(3) Uani d . 1 1
H H10A 0.1978 0.6902 0.1909 0.054 Uiso calc R 1 1
C C11 0.26556(14) 0.56587(12) 0.31472(11) 0.0399(3) Uani d . 1 1
H H11A 0.3344 0.5309 0.2830 0.048 Uiso calc R 1 1
C C12 0.24526(12) 0.52207(11) 0.41692(10) 0.0336(2) Uani d . 1 1
C C13 0.32454(13) 0.41235(11) 0.47546(10) 0.0356(3) Uani d . 1 1
H H1N1 0.4981(19) 0.2561(18) 0.0206(15) 0.067(5) Uiso d . 1 1
H H2N2 0.393(2) 0.227(2) 0.1687(17) 0.075(6) Uiso d . 1 1
H H1N2 0.4328(19) 0.3062(17) 0.2770(17) 0.060(5) Uiso d . 1 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'
Cl Cl 0.1484 0.1585 '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 122.05(12)
C1 N1 H1N1 121.7(10)
C5 N1 H1N1 116.2(10)
C1 N2 H2N2 117.2(12)
C1 N2 H1N2 118.2(13)
H2N2 N2 H1N2 122.3(17)
N2 C1 N1 119.39(13)
N2 C1 C2 123.06(13)
N1 C1 C2 117.55(13)
C3 C2 C1 119.92(13)
C3 C2 H2A 120.0
C1 C2 H2A 120.0
C2 C3 C4 121.78(13)
C2 C3 H3A 119.1
C4 C3 H3A 119.1
C5 C4 C3 116.24(13)
C5 C4 C6 122.81(14)
C3 C4 C6 120.95(14)
C4 C5 N1 122.46(13)
C4 C5 H5A 118.8
N1 C5 H5A 118.8
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C12 121.22(13)
C8 C7 H7A 119.4
C12 C7 H7A 119.4
C9 C8 C7 118.80(13)
C9 C8 H8A 120.6
C7 C8 H8A 120.6
C10 C9 C8 121.41(13)
C10 C9 Cl1 119.23(12)
C8 C9 Cl1 119.36(11)
C9 C10 C11 119.16(13)
C9 C10 H10A 120.4
C11 C10 H10A 120.4
C10 C11 C12 120.66(12)
C10 C11 H11A 119.7
C12 C11 H11A 119.7
C7 C12 C11 118.71(12)
C7 C12 C13 119.06(11)
C11 C12 C13 122.18(11)
O2 C13 O1 124.56(12)
O2 C13 C12 116.49(11)
O1 C13 C12 118.93(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.7390(14)
O1 C13 1.2619(16)
O2 C13 1.2436(16)
N1 C1 1.3495(16)
N1 C5 1.3596(18)
N1 H1N1 0.98(2)
N2 C1 1.3245(19)
N2 H2N2 0.92(2)
N2 H1N2 0.85(2)
C1 C2 1.4113(19)
C2 C3 1.354(2)
C2 H2A 0.9300
C3 C4 1.413(2)
C3 H3A 0.9300
C4 C5 1.3539(19)
C4 C6 1.503(2)
C5 H5A 0.9300
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.382(2)
C7 C12 1.3856(18)
C7 H7A 0.9300
C8 C9 1.379(2)
C8 H8A 0.9300
C9 C10 1.374(2)
C10 C11 1.3870(18)
C10 H10A 0.9300
C11 C12 1.3881(18)
C11 H11A 0.9300
C12 C13 1.5097(16)
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
N2 H1N2 O1 . 0.85(2) 2.02(2) 2.8654(18) 174.1(19) yes
N1 H1N1 O1 4_565 0.98(2) 1.75(2) 2.7255(14) 174.1(16) yes
N2 H2N2 O2 4_565 0.92(2) 1.83(2) 2.7437(17) 172.7(18) yes
C2 H2A O2 3_666 0.93 2.40 3.1459(18) 137 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 -179.57(13)
C5 N1 C1 C2 -0.37(19)
N2 C1 C2 C3 179.28(15)
N1 C1 C2 C3 0.1(2)
C1 C2 C3 C4 0.4(2)
C2 C3 C4 C5 -0.6(2)
C2 C3 C4 C6 179.69(15)
C3 C4 C5 N1 0.3(2)
C6 C4 C5 N1 -179.95(14)
C1 N1 C5 C4 0.1(2)
C12 C7 C8 C9 -0.7(2)
C7 C8 C9 C10 -0.8(2)
C7 C8 C9 Cl1 178.64(12)
C8 C9 C10 C11 1.0(2)
Cl1 C9 C10 C11 -178.43(11)
C9 C10 C11 C12 0.3(2)
C8 C7 C12 C11 2.0(2)
C8 C7 C12 C13 -175.35(13)
C10 C11 C12 C7 -1.8(2)
C10 C11 C12 C13 175.48(12)
C7 C12 C13 O2 0.45(17)
C11 C12 C13 O2 -176.81(12)
C7 C12 C13 O1 179.13(12)
C11 C12 C13 O1 1.87(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658284
