#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/73/2207346.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_2207346
loop_
_publ_author_name
'Amoore, Jarrod J. M.'
'Kepert, Cameron J.'
_publ_section_title
;
 4-(4-Pyridylamino)pyridinium isophthalate
;
_journal_coeditor_code           SJ6139
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3937
_journal_page_last               o3938
_journal_paper_doi               10.1107/S160053680503463X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 N3 H10 +, C8 H5 O4 -'
_chemical_formula_moiety         'C10 N3 H10 +, C8 H5 O4 -'
_chemical_formula_sum            'C18 H15 N3 O4'
_chemical_formula_weight         337.33
_chemical_name_systematic
;
4-(4-Pyridylamino)pyridinium isophthalate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.787(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3246(18)
_cell_length_b                   15.134(3)
_cell_length_c                   11.655(2)
_cell_measurement_reflns_used    936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.9285
_cell_measurement_theta_min      2.6595
_cell_volume                     1566.1(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1997)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and MERCURY (Version 1.4; Bruno et al., 2002)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15761
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         138
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.899528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick 1996)'
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular polygon'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0367
_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)+(0.0457P)²+0.7162P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                3246
_reflns_number_total             3742
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6139.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 

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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2207346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 0.34974(10) 0.11099(5) 0.41885(8) 0.02368(19) Uani d . 1 O
O2 0.19178(10) 0.10254(6) 0.52802(8) 0.0259(2) Uani d . 1 O
O3 0.63653(11) 0.39044(6) 0.44486(8) 0.0295(2) Uani d . 1 O
H3A 0.6894 0.4285 0.4241 0.044 Uiso calc R 1 H
O4 0.67686(11) 0.47818(6) 0.60559(9) 0.0320(2) Uani d . 1 O
N1 0.20141(12) 0.48577(7) 0.62266(10) 0.0246(2) Uani d . 1 N
N2 -0.23674(11) 0.05480(6) 0.62987(9) 0.0222(2) Uani d . 1 N
H2A -0.2714 0.0011 0.6096 0.027 Uiso calc R 1 H
N3 -0.08474(11) 0.30872(6) 0.72439(9) 0.0211(2) Uani d . 1 N
H3B -0.1206 0.3313 0.7796 0.025 Uiso calc R 1 H
C1 0.18105(14) 0.48763(8) 0.73191(11) 0.0247(3) Uani d . 1 C
H1 0.2327 0.5314 0.7878 0.030 Uiso calc R 1 H
C2 0.08894(14) 0.42925(8) 0.76701(11) 0.0230(2) Uani d . 1 C
H2B 0.0780 0.4332 0.8452 0.028 Uiso calc R 1 H
C3 0.01176(12) 0.36414(7) 0.68646(10) 0.0196(2) Uani d . 1 C
C4 0.03145(13) 0.36225(8) 0.57240(11) 0.0228(2) Uani d . 1 C
H4 -0.0195 0.3198 0.5142 0.027 Uiso calc R 1 H
C5 0.12717(14) 0.42383(8) 0.54597(11) 0.0242(2) Uani d . 1 C
H5 0.1406 0.4217 0.4684 0.029 Uiso calc R 1 H
C6 -0.12665(14) 0.08682(8) 0.58937(11) 0.0234(2) Uani d . 1 C
H6 -0.0859 0.0504 0.5407 0.028 Uiso calc R 1 H
C7 -0.07177(13) 0.17079(8) 0.61657(10) 0.0219(2) Uani d . 1 C
H7 0.0060 0.1923 0.5870 0.026 Uiso calc R 1 H
C8 -0.13196(12) 0.22486(7) 0.68888(10) 0.0186(2) Uani d . 1 C
C9 -0.24476(13) 0.18829(7) 0.73203(10) 0.0198(2) Uani d . 1 C
H9 -0.2863 0.2223 0.7827 0.024 Uiso calc R 1 H
C10 -0.29427(13) 0.10423(8) 0.70116(10) 0.0213(2) Uani d . 1 C
H10 -0.3705 0.0802 0.7304 0.026 Uiso calc R 1 H
C11 0.46110(12) 0.27514(7) 0.52942(10) 0.0192(2) Uani d . 1 C
H11 0.4780 0.2627 0.4547 0.023 Uiso calc R 1 H
C12 0.52574(13) 0.34998(7) 0.59467(10) 0.0204(2) Uani d . 1 C
C13 0.50560(13) 0.36639(8) 0.70637(11) 0.0233(2) Uani d . 1 C
H13 0.5499 0.4171 0.7513 0.028 Uiso calc R 1 H
C14 0.42108(14) 0.30888(8) 0.75221(11) 0.0236(2) Uani d . 1 C
H14 0.4101 0.3193 0.8295 0.028 Uiso calc R 1 H
C15 0.35235(13) 0.23600(8) 0.68506(10) 0.0214(2) Uani d . 1 C
H15 0.2917 0.1978 0.7156 0.026 Uiso calc R 1 H
C16 0.37188(12) 0.21845(7) 0.57293(10) 0.0184(2) Uani d . 1 C
C17 0.61995(13) 0.41295(8) 0.54945(11) 0.0228(2) Uani d . 1 C
C18 0.29773(13) 0.13812(7) 0.50157(10) 0.0185(2) Uani d . 1 C
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
C17 O3 H3A 109.5
C5 N1 C1 117.08(10)
C6 N2 C10 120.50(10)
C6 N2 H2A 119.7
C10 N2 H2A 119.7
C8 N3 C3 129.89(10)
C8 N3 H3B 115.1
C3 N3 H3B 115.1
N1 C1 C2 123.29(11)
N1 C1 H1 118.4
C2 C1 H1 118.4
C1 C2 C3 119.45(11)
C1 C2 H2B 120.3
C3 C2 H2B 120.3
C4 C3 N3 125.00(11)
C4 C3 C2 117.57(11)
N3 C3 C2 117.35(10)
C5 C4 C3 118.54(11)
C5 C4 H4 120.7
C3 C4 H4 120.7
N1 C5 C4 124.07(11)
N1 C5 H5 118.0
C4 C5 H5 118.0
N2 C6 C7 121.62(11)
N2 C6 H6 119.2
C7 C6 H6 119.2
C6 C7 C8 119.23(11)
C6 C7 H7 120.4
C8 C7 H7 120.4
N3 C8 C7 124.80(10)
N3 C8 C9 117.60(10)
C7 C8 C9 117.53(10)
C10 C9 C8 120.09(11)
C10 C9 H9 120.0
C8 C9 H9 120.0
N2 C10 C9 121.00(11)
N2 C10 H10 119.5
C9 C10 H10 119.5
C16 C11 C12 120.54(11)
C16 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 119.68(11)
C13 C12 C17 118.47(10)
C11 C12 C17 121.84(11)
C14 C13 C12 120.20(11)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 119.99(11)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C16 120.47(11)
C14 C15 H15 119.8
C16 C15 H15 119.8
C11 C16 C15 119.05(10)
C11 C16 C18 121.14(10)
C15 C16 C18 119.81(10)
O4 C17 O3 123.57(11)
O4 C17 C12 122.35(11)
O3 C17 C12 114.07(10)
O2 C18 O1 124.29(11)
O2 C18 C16 118.37(10)
O1 C18 C16 117.33(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C18 1.2724(14)
O2 C18 1.2439(14)
O3 C17 1.3195(15)
O3 H3A 0.8400
O4 C17 1.2132(15)
N1 C5 1.3337(16)
N1 C1 1.3438(16)
N2 C6 1.3445(16)
N2 C10 1.3454(16)
N2 H2A 0.8800
N3 C8 1.3654(15)
N3 C3 1.3970(14)
N3 H3B 0.8800
C1 C2 1.3785(17)
C1 H1 0.9500
C2 C3 1.3992(16)
C2 H2B 0.9500
C3 C4 1.3966(16)
C4 C5 1.3886(17)
C4 H4 0.9500
C5 H5 0.9500
C6 C7 1.3705(17)
C6 H6 0.9500
C7 C8 1.4085(16)
C7 H7 0.9500
C8 C9 1.4102(16)
C9 C10 1.3637(17)
C9 H9 0.9500
C10 H10 0.9500
C11 C16 1.3939(15)
C11 C12 1.3945(16)
C11 H11 0.9500
C12 C13 1.3931(17)
C12 C17 1.4969(16)
C13 C14 1.3861(17)
C13 H13 0.9500
C14 C15 1.3905(17)
C14 H14 0.9500
C15 C16 1.3990(16)
C15 H15 0.9500
C16 C18 1.5153(15)
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 H2A O1 3_556 0.88 1.84 2.7134(14) 174 yes
O3 H3A N1 3_666 0.84 1.83 2.6720(14) 178 yes
N3 H3B O1 4_566 0.88 1.94 2.7987(13) 166 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
C7 C8 C3 C4 32.47(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127008
