#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225392.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_2225392
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-5-chloropyridinium 4-hydroxybenzoate
;
_journal_coeditor_code           TK2625
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o557
_journal_paper_doi               10.1107/S1600536810004265
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H6 Cl N2 + , C7 H5 O3 -'
_chemical_formula_moiety         'C5 H6 Cl N2 + , C7 H5 O3 -'
_chemical_formula_sum            'C12 H11 Cl N2 O3'
_chemical_formula_weight         266.68
_chemical_name_systematic
;
2-Amino-5-chloropyridinium 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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 116.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0893(3)
_cell_length_b                   11.7612(4)
_cell_length_c                   11.6634(3)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      2.3
_cell_volume                     1242.74(7)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.020
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12446
_diffrn_reflns_theta_full        30.1
_diffrn_reflns_theta_max         30.1
_diffrn_reflns_theta_min         2.3
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.040
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.2067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.110
_reflns_number_gt                2663
_reflns_number_total             3630
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2625.cif
_cod_data_source_block           I
_cod_original_cell_volume        1242.74(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225392
_cod_database_fobs_code          2225392
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
Cl Cl1 0.21064(4) 0.98776(4) -0.17272(4) 0.06226(15) Uani d . 1 . .
N N1 0.51321(13) 0.78671(10) 0.07645(11) 0.0444(3) Uani d . 1 . .
N N2 0.63089(16) 0.77385(14) 0.29586(13) 0.0574(3) Uani d . 1 . .
C C1 0.53134(15) 0.82441(12) 0.19187(13) 0.0439(3) Uani d . 1 . .
C C2 0.44186(16) 0.91497(14) 0.19530(14) 0.0510(4) Uani d . 1 . .
C C3 0.34358(17) 0.96337(14) 0.08507(15) 0.0512(4) Uani d . 1 . .
C C4 0.33162(14) 0.92372(13) -0.03259(13) 0.0454(3) Uani d . 1 . .
C C5 0.41534(15) 0.83516(13) -0.03444(13) 0.0454(3) Uani d . 1 . .
O O1 0.00092(13) 0.66336(10) 0.45630(11) 0.0579(3) Uani d . 1 . .
O O2 0.34526(13) 1.11961(9) 0.47186(9) 0.0567(3) Uani d . 1 . .
O O3 0.22698(11) 1.09176(8) 0.26301(8) 0.0463(2) Uani d . 1 . .
C C6 0.21056(18) 0.92410(14) 0.51840(13) 0.0531(4) Uani d . 1 . .
C C7 0.14592(19) 0.82697(15) 0.53591(13) 0.0563(4) Uani d . 1 . .
C C8 0.06192(15) 0.75826(12) 0.43312(13) 0.0438(3) Uani d . 1 . .
C C9 0.04555(15) 0.78713(12) 0.31209(12) 0.0426(3) Uani d . 1 . .
C C10 0.11107(14) 0.88452(12) 0.29507(12) 0.0397(3) Uani d . 1 . .
C C11 0.19355(14) 0.95522(12) 0.39715(11) 0.0392(3) Uani d . 1 . .
C C12 0.25875(14) 1.06243(12) 0.37582(12) 0.0398(3) Uani d . 1 . .
H H2A 0.4538(17) 0.9382(14) 0.2769(16) 0.059(5) Uiso d . 1 . .
H H3A 0.283(2) 1.0251(15) 0.0866(17) 0.064(5) Uiso d . 1 . .
H H5A 0.4139(17) 0.8021(14) -0.1096(16) 0.060(5) Uiso d . 1 . .
H H6A 0.2676(19) 0.9721(15) 0.5889(17) 0.065(5) Uiso d . 1 . .
H H7A 0.1571(19) 0.8087(16) 0.6168(18) 0.068(5) Uiso d . 1 . .
H H9A -0.0099(17) 0.7369(13) 0.2417(15) 0.054(4) Uiso d . 1 . .
H H10A 0.1007(16) 0.9043(13) 0.2125(15) 0.048(4) Uiso d . 1 . .
H H1O1 -0.053(2) 0.6331(17) 0.386(2) 0.073(6) Uiso d . 1 . .
H H1N1 0.575(2) 0.7250(16) 0.0689(18) 0.076(6) Uiso d . 1 . .
H H1N2 0.6509(19) 0.8050(16) 0.3681(18) 0.062(5) Uiso d . 1 . .
H H2N2 0.689(2) 0.7177(19) 0.2877(19) 0.080(6) 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C5 . . 122.24(12) ?
C1 N1 H1N1 . . 121.1(11) ?
C5 N1 H1N1 . . 116.5(11) ?
C1 N2 H1N2 . . 117.6(12) ?
C1 N2 H2N2 . . 119.3(13) ?
H1N2 N2 H2N2 . . 121.8(18) ?
N2 C1 N1 . . 118.66(13) ?
N2 C1 C2 . . 123.35(13) ?
N1 C1 C2 . . 117.98(13) ?
C3 C2 C1 . . 120.07(13) ?
C3 C2 H2A . . 123.3(10) ?
C1 C2 H2A . . 116.6(10) ?
C2 C3 C4 . . 120.00(14) ?
C2 C3 H3A . . 120.6(11) ?
C4 C3 H3A . . 119.4(11) ?
C5 C4 C3 . . 119.20(13) ?
C5 C4 Cl1 . . 120.66(11) ?
C3 C4 Cl1 . . 120.14(11) ?
C4 C5 N1 . . 120.45(13) ?
C4 C5 H5A . . 125.1(10) ?
N1 C5 H5A . . 114.5(10) ?
C8 O1 H1O1 . . 108.3(14) ?
C7 C6 C11 . . 120.90(13) ?
C7 C6 H6A . . 120.6(11) ?
C11 C6 H6A . . 118.5(11) ?
C6 C7 C8 . . 120.42(13) ?
C6 C7 H7A . . 119.5(11) ?
C8 C7 H7A . . 120.1(11) ?
O1 C8 C7 . . 117.77(12) ?
O1 C8 C9 . . 122.79(12) ?
C7 C8 C9 . . 119.43(13) ?
C10 C9 C8 . . 119.92(12) ?
C10 C9 H9A . . 121.4(10) ?
C8 C9 H9A . . 118.7(10) ?
C9 C10 C11 . . 121.19(12) ?
C9 C10 H10A . . 120.2(9) ?
C11 C10 H10A . . 118.7(9) ?
C10 C11 C6 . . 118.13(13) ?
C10 C11 C12 . . 120.30(11) ?
C6 C11 C12 . . 121.56(12) ?
O3 C12 O2 . . 122.55(12) ?
O3 C12 C11 . . 118.55(11) ?
O2 C12 C11 . . 118.89(11) ?
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
Cl1 C4 . 1.7241(15) ?
N1 C1 . 1.3511(17) ?
N1 C5 . 1.3595(18) ?
N1 H1N1 . 0.99(2) ?
N2 C1 . 1.3271(19) ?
N2 H1N2 . 0.858(19) ?
N2 H2N2 . 0.91(2) ?
C1 C2 . 1.408(2) ?
C2 C3 . 1.356(2) ?
C2 H2A . 0.946(16) ?
C3 C4 . 1.403(2) ?
C3 H3A . 0.953(18) ?
C4 C5 . 1.347(2) ?
C5 H5A . 0.953(17) ?
O1 C8 . 1.3581(17) ?
O1 H1O1 . 0.83(2) ?
O2 C12 . 1.2682(15) ?
O3 C12 . 1.2577(15) ?
C6 C7 . 1.375(2) ?
C6 C11 . 1.3963(18) ?
C6 H6A . 0.954(18) ?
C7 C8 . 1.384(2) ?
C7 H7A . 0.925(19) ?
C8 C9 . 1.3892(19) ?
C9 C10 . 1.3798(19) ?
C9 H9A . 0.965(16) ?
C10 C11 . 1.3889(18) ?
C10 H10A . 0.950(15) ?
C11 C12 . 1.4929(19) ?
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 H1O1 O3 2_545 0.84(2) 1.91(2) 2.7132(15) 160(2) yes
N1 H1N1 O2 2_645 0.99(2) 1.66(2) 2.6320(18) 169.2(18) yes
N2 H1N2 O2 3_676 0.857(19) 2.051(19) 2.8972(18) 169(2) yes
N2 H2N2 O3 2_645 0.92(2) 1.93(2) 2.825(2) 167(2) yes
C3 H3A O3 . 0.95(2) 2.488(19) 3.181(2) 129.5(14) 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
C5 N1 C1 N2 . . . . -178.89(13) ?
C5 N1 C1 C2 . . . . 1.8(2) ?
N2 C1 C2 C3 . . . . 179.25(15) ?
N1 C1 C2 C3 . . . . -1.5(2) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . 2.1(2) ?
C2 C3 C4 Cl1 . . . . -178.10(12) ?
C3 C4 C5 N1 . . . . -1.8(2) ?
Cl1 C4 C5 N1 . . . . 178.38(11) ?
C1 N1 C5 C4 . . . . -0.2(2) ?
C11 C6 C7 C8 . . . . -0.3(3) ?
C6 C7 C8 O1 . . . . 179.94(15) ?
C6 C7 C8 C9 . . . . 1.2(2) ?
O1 C8 C9 C10 . . . . -179.65(13) ?
C7 C8 C9 C10 . . . . -0.9(2) ?
C8 C9 C10 C11 . . . . -0.2(2) ?
C9 C10 C11 C6 . . . . 1.0(2) ?
C9 C10 C11 C12 . . . . -177.69(12) ?
C7 C6 C11 C10 . . . . -0.8(2) ?
C7 C6 C11 C12 . . . . 177.90(15) ?
C10 C11 C12 O3 . . . . 5.95(19) ?
C6 C11 C12 O3 . . . . -172.73(13) ?
C10 C11 C12 O2 . . . . -173.19(12) ?
C6 C11 C12 O2 . . . . 8.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656037
