#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/45/2234540.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_2234540
loop_
_publ_author_name
'Rodrigues, V. H.'
'Hakimi, Mohammad'
'Motieiyan, Elham'
_publ_section_title
;
 Bis(2-aminopyridinium) 2,5-dicarboxybenzene-1,4-dicarboxylate
;
_journal_coeditor_code           BT5880
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1524
_journal_paper_doi               10.1107/S1600536812017254
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C5 H7 N2 +, C10 H4 O8 2-'
_chemical_formula_moiety         '2(C5 H7 N2 +), C10 H4 O8 2-'
_chemical_formula_sum            'C20 H18 N4 O8'
_chemical_formula_weight         442.38
_chemical_name_systematic
;
Bis(2-aminopyridinium) 2,5-dicarboxybenzene-1,4-dicarboxylate
;
_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                 99.535(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.01650(10)
_cell_length_b                   10.8098(4)
_cell_length_c                   21.4036(7)
_cell_measurement_reflns_used    7209
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.9290
_cell_measurement_theta_min      2.6785
_cell_volume                     916.45(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker--Nonius, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
;
Bruker--Nonius APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18838
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.755103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.014(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   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0373
_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)+(0.0519P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1652
_reflns_number_total             2209
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5880.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234540
_cod_database_fobs_code          2234540
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
N N1 1.1547(3) 0.04940(11) 0.38178(5) 0.0424(3) Uani d . 1 1
H H1A 1.040(4) 0.1095(15) 0.3993(8) 0.051 Uiso d . 1 1
C C1 1.1679(3) 0.04905(12) 0.32019(6) 0.0370(3) Uani d . 1 1
N N2 1.0229(4) 0.14007(12) 0.28496(6) 0.0511(3) Uani d . 1 1
H H2A 1.021(4) 0.1363(16) 0.2461(9) 0.061 Uiso d . 1 1
H H2B 0.916(5) 0.1990(16) 0.3019(9) 0.061 Uiso d . 1 1
C C3 1.3390(4) -0.04878(13) 0.29700(7) 0.0469(4) Uani d . 1 1
H H3 1.3508 -0.0532 0.2540 0.056 Uiso calc R 1 1
C C4 1.4882(4) -0.13741(15) 0.33704(9) 0.0569(4) Uani d . 1 1
H H4 1.6042 -0.2019 0.3215 0.068 Uiso calc R 1 1
C C5 1.4684(4) -0.13228(16) 0.40058(9) 0.0587(4) Uani d . 1 1
H H5 1.5712 -0.1922 0.4285 0.070 Uiso calc R 1 1
C C6 1.2984(4) -0.03922(15) 0.42096(7) 0.0523(4) Uani d . 1 1
H H6 1.2786 -0.0356 0.4636 0.063 Uiso calc R 1 1
C C7 0.7030(3) 0.40755(11) 0.52514(6) 0.0325(3) Uani d . 1 1
H H7 0.8444 0.3440 0.5427 0.039 Uiso calc R 1 1
C C8 0.5869(3) 0.40386(11) 0.46123(5) 0.0312(3) Uani d . 1 1
C C9 0.7148(3) 0.29317(12) 0.42838(6) 0.0380(3) Uani d . 1 1
O O1 0.6529(3) 0.28618(10) 0.36938(5) 0.0588(3) Uani d . 1 1
O O2 0.8806(3) 0.21344(9) 0.45984(5) 0.0591(3) Uani d . 1 1
C C10 0.3760(3) 0.50071(11) 0.43487(5) 0.0315(3) Uani d . 1 1
C C11 0.2130(3) 0.52081(12) 0.36717(6) 0.0386(3) Uani d . 1 1
O O3 0.0283(3) 0.60888(10) 0.35332(5) 0.0571(3) Uani d . 1 1
O O4 0.2721(3) 0.44339(10) 0.32502(4) 0.0556(3) Uani d . 1 1
H H4A 0.448(5) 0.3738(17) 0.3439(8) 0.067 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'
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
C1 N1 C6 . . 122.39(13)
C1 N1 H1A . . 121.0(10)
C6 N1 H1A . . 116.6(10)
N2 C1 N1 . . 118.70(13)
N2 C1 C3 . . 124.06(13)
N1 C1 C3 . . 117.24(13)
C1 N2 H2A . . 117.8(12)
C1 N2 H2B . . 120.4(12)
H2A N2 H2B . . 121.5(17)
C4 C3 C1 . . 120.15(14)
C4 C3 H3 . . 119.9
C1 C3 H3 . . 119.9
C3 C4 C5 . . 120.25(15)
C3 C4 H4 . . 119.9
C5 C4 H4 . . 119.9
C6 C5 C4 . . 118.13(15)
C6 C5 H5 . . 120.9
C4 C5 H5 . . 120.9
C5 C6 N1 . . 121.83(15)
C5 C6 H6 . . 119.1
N1 C6 H6 . . 119.1
C8 C7 C10 . 3_666 124.36(12)
C8 C7 H7 . . 117.8
C10 C7 H7 3_666 . 117.8
C7 C8 C10 . . 117.52(11)
C7 C8 C9 . . 113.54(11)
C10 C8 C9 . . 128.93(11)
O2 C9 O1 . . 120.93(12)
O2 C9 C8 . . 119.73(11)
O1 C9 C8 . . 119.33(12)
C7 C10 C8 3_666 . 118.12(11)
C7 C10 C11 3_666 . 112.67(11)
C8 C10 C11 . . 129.20(11)
O3 C11 O4 . . 121.18(12)
O3 C11 C10 . . 119.99(12)
O4 C11 C10 . . 118.83(12)
C11 O4 H4A . . 112.5(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.3281(17)
N1 C6 . 1.3392(19)
N1 H1A . 0.913(16)
C1 N2 . 1.3154(19)
C1 C3 . 1.3964(19)
N2 H2A . 0.831(19)
N2 H2B . 0.880(19)
C3 C4 . 1.357(2)
C3 H3 . 0.9300
C4 C5 . 1.377(2)
C4 H4 . 0.9300
C5 C6 . 1.329(2)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 C8 . 1.3707(17)
C7 C10 3_666 1.3809(17)
C7 H7 . 0.9300
C8 C10 . 1.4049(18)
C8 C9 . 1.5197(17)
C9 O2 . 1.2212(16)
C9 O1 . 1.2483(16)
C10 C7 3_666 1.3809(17)
C10 C11 . 1.5037(17)
C11 O3 . 1.2133(17)
C11 O4 . 1.2811(16)
O4 H4A . 1.06(2)
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
N1 H1A O2 . 0.913(16) 1.904(17) 2.7852(15) 161.6(15)
N1 H1A O1 . 0.913(16) 2.478(16) 3.2413(16) 141.4(13)
N2 H2A O3 2_645 0.831(19) 2.125(19) 2.9520(17) 173.0(17)
N2 H2B O1 . 0.880(19) 2.14(2) 2.9759(17) 157.6(16)
O4 H4A O1 . 1.06(2) 1.31(2) 2.3766(15) 176.8(17)
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_4
_geom_torsion
C6 N1 C1 N2 . . -179.42(13)
C6 N1 C1 C3 . . 0.14(19)
N2 C1 C3 C4 . . 178.46(14)
N1 C1 C3 C4 . . -1.1(2)
C1 C3 C4 C5 . . 0.8(2)
C3 C4 C5 C6 . . 0.5(2)
C4 C5 C6 N1 . . -1.4(2)
C1 N1 C6 C5 . . 1.1(2)
C10 C7 C8 C10 3_666 . 0.60(19)
C10 C7 C8 C9 3_666 . 179.58(11)
C7 C8 C9 O2 . . 5.76(17)
C10 C8 C9 O2 . . -175.39(13)
C7 C8 C9 O1 . . -173.10(12)
C10 C8 C9 O1 . . 5.7(2)
C7 C8 C10 C7 . 3_666 -0.56(18)
C9 C8 C10 C7 . 3_666 -179.36(11)
C7 C8 C10 C11 . . -179.96(11)
C9 C8 C10 C11 . . 1.2(2)
C7 C10 C11 O3 3_666 . -1.71(17)
C8 C10 C11 O3 . . 177.72(13)
C7 C10 C11 O4 3_666 . 178.55(12)
C8 C10 C11 O4 . . -2.01(19)
