#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/34/2233468.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_2233468
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Goh, Jia Hao'
'Fun, Hoong-Kun'
_publ_section_title
;
 Bis(2,3-diaminopyridinium) phthalate dihydrate
;
_journal_coeditor_code           HB6574
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o402
_journal_paper_doi               10.1107/S1600536811055838
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C5 H8 N3 +, C8 H4 O4 -, 2H2 O'
_chemical_formula_moiety         '2(C5 H8 N3 +), (C8 H4 O4 -), 2(H2 O)'
_chemical_formula_sum            'C18 H24 N6 O6'
_chemical_formula_weight         420.43
_chemical_name_common
;
Bis(2,3-Diaminopyridinium) phthalate dihydrate
;
_chemical_name_systematic
;
Bis(2,3-diaminopyridinium) benzene-1,2-dicarboxylate dihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.194(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.795(5)
_cell_length_b                   13.083(4)
_cell_length_c                   11.012(4)
_cell_measurement_reflns_used    3390
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.79
_cell_measurement_theta_min      2.80
_cell_volume                     2059.1(12)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10343
_diffrn_reflns_theta_full        29.93
_diffrn_reflns_theta_max         29.93
_diffrn_reflns_theta_min         2.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0426
_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)+(0.0653P)²+0.7423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2148
_reflns_number_total             2955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6574.cif
_cod_data_source_block           I
_cod_original_cell_volume        2059.2(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2233468
_cod_database_fobs_code          2233468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
_atom_site_symmetry_multiplicity
N N1 0.23077(8) 0.94380(9) 1.03746(11) 0.0227(3) Uani d 1 1
N N2 0.30262(8) 0.94315(10) 0.89459(13) 0.0256(3) Uani d 1 1
N N3 0.17815(10) 0.78666(11) 0.74285(14) 0.0330(3) Uani d 1 1
C C1 0.23819(9) 0.90400(10) 0.93023(13) 0.0192(3) Uani d 1 1
C C2 0.17516(9) 0.82430(9) 0.85688(13) 0.0210(3) Uani d 1 1
C C3 0.11106(9) 0.79131(11) 0.90331(14) 0.0249(3) Uani d 1 1
C C4 0.10585(11) 0.83570(13) 1.01540(15) 0.0313(3) Uani d 1 1
C C5 0.16621(11) 0.91224(13) 1.08149(15) 0.0310(3) Uani d 1 1
O O1 0.43751(6) 0.07071(7) 0.10193(9) 0.0225(2) Uani d 1 1
O O2 0.32273(6) 0.12167(7) 0.15491(9) 0.0225(2) Uani d 1 1
C C6 0.45346(10) 0.41720(10) 0.20469(14) 0.0242(3) Uani d 1 1
C C7 0.40590(9) 0.32537(10) 0.16012(13) 0.0201(3) Uani d 1 1
C C8 0.45249(8) 0.23274(9) 0.20552(12) 0.0160(2) Uani d 1 1
C C9 0.40094(8) 0.13405(9) 0.15149(12) 0.0168(2) Uani d 1 1
O O1W 0.45043(8) 0.10881(8) 0.86130(12) 0.0315(3) Uani d 1 1
H H1 0.3388(12) 0.3242(12) 0.0959(17) 0.028(4) Uiso d 1 1
H H2 0.0692(11) 0.7346(13) 0.8557(17) 0.026(4) Uiso d 1 1
H H3 0.4209(12) 0.4807(14) 0.1749(17) 0.032(4) Uiso d 1 1
H H4 0.1689(13) 0.9496(15) 1.160(2) 0.043(5) Uiso d 1 1
H H5 0.3138(13) 0.9165(14) 0.8275(19) 0.033(5) Uiso d 1 1
H H6 0.2697(12) 1.0029(15) 1.0806(18) 0.036(5) Uiso d 1 1
H H7 0.3468(13) 0.9879(15) 0.9506(19) 0.039(5) Uiso d 1 1
H H8 0.0557(13) 0.8149(14) 1.044(2) 0.042(5) Uiso d 1 1
H H9 0.1404(14) 0.7328(17) 0.712(2) 0.046(5) Uiso d 1 1
H H10 0.2265(14) 0.7967(14) 0.723(2) 0.040(5) Uiso d 1 1
H H11 0.4555(16) 0.1035(17) 0.950(3) 0.064(7) Uiso d 1 1
H H12 0.4828(16) 0.0542(18) 0.850(2) 0.062(7) 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 C5 . . 123.61(12)
C1 N1 H6 . . 117.6(11)
C5 N1 H6 . . 118.5(10)
C1 N2 H5 . . 122.2(12)
C1 N2 H7 . . 120.2(11)
H5 N2 H7 . . 116.0(16)
C2 N3 H9 . . 111.0(13)
C2 N3 H10 . . 122.9(13)
H9 N3 H10 . . 121.6(18)
N2 C1 N1 . . 118.16(12)
N2 C1 C2 . . 123.13(12)
N1 C1 C2 . . 118.67(12)
N3 C2 C3 . . 122.93(12)
N3 C2 C1 . . 119.54(12)
C3 C2 C1 . . 117.49(12)
C2 C3 C4 . . 121.61(13)
C2 C3 H2 . . 118.0(10)
C4 C3 H2 . . 120.4(10)
C5 C4 C3 . . 119.14(13)
C5 C4 H8 . . 119.7(11)
C3 C4 H8 . . 121.0(11)
C4 C5 N1 . . 119.44(14)
C4 C5 H4 . . 126.7(11)
N1 C5 H4 . . 113.8(11)
C6 C6 C7 2_655 . 120.25(8)
C6 C6 H3 2_655 . 119.9(10)
C7 C6 H3 . . 119.8(10)
C6 C7 C8 . . 120.03(12)
C6 C7 H1 . . 121.1(10)
C8 C7 H1 . . 118.9(10)
C7 C8 C8 . 2_655 119.70(7)
C7 C8 C9 . . 119.26(11)
C8 C8 C9 2_655 . 120.95(6)
O1 C9 O2 . . 124.30(11)
O1 C9 C8 . . 117.67(11)
O2 C9 C8 . . 117.99(11)
H11 O1W H12 . . 105.6(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.3404(17)
N1 C5 . 1.3663(18)
N1 H6 . 0.98(2)
N2 C1 . 1.3388(17)
N2 H5 . 0.899(19)
N2 H7 . 0.92(2)
N3 C2 . 1.3683(19)
N3 H9 . 0.89(2)
N3 H10 . 0.89(2)
C1 C2 . 1.4304(18)
C2 C3 . 1.383(2)
C3 C4 . 1.398(2)
C3 H2 . 0.983(17)
C4 C5 . 1.360(2)
C4 H8 . 1.01(2)
C5 H4 . 0.98(2)
O1 C9 . 1.2596(15)
O2 C9 . 1.2623(15)
C6 C6 2_655 1.382(3)
C6 C7 . 1.3910(19)
C6 H3 . 0.959(18)
C7 C8 . 1.3954(17)
C7 H1 . 0.993(17)
C8 C8 2_655 1.400(2)
C8 C9 . 1.5072(17)
O1W H11 . 0.95(3)
O1W H12 . 0.91(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
_geom_hbond_publ_flag
N2 H5 O2 6_566 0.90(2) 2.03(2) 2.9155(19) 169.0(18) yes
N1 H6 O2 1_566 0.98(2) 1.790(19) 2.7565(18) 170.3(19) yes
N2 H7 O1 1_566 0.92(2) 1.99(2) 2.8976(19) 168.1(19) yes
N3 H9 O1W 4_556 0.89(2) 2.09(2) 2.978(2) 179(3) yes
N3 H10 O2 6_566 0.89(2) 2.23(2) 3.078(2) 158.8(17) yes
O1W H11 O1 1_556 0.95(3) 1.86(3) 2.7878(18) 165(3) yes
O1W H12 O1 5_656 0.92(2) 1.99(2) 2.8641(18) 158.2(19) yes
C3 H2 O1W 3_455 0.984(17) 2.516(18) 3.369(2) 145.0(14) yes
C4 H8 Cg1 4_556 1.01(2) 2.76(2) 3.629(2) 144.3(15) yes
C6 H3 Cg2 7_566 0.959(18) 2.568(18) 3.497(2) 163.4(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_4
_geom_torsion
C5 N1 C1 N2 . . 178.22(13)
C5 N1 C1 C2 . . 0.2(2)
N2 C1 C2 N3 . . -1.5(2)
N1 C1 C2 N3 . . 176.36(12)
N2 C1 C2 C3 . . -179.27(13)
N1 C1 C2 C3 . . -1.39(18)
N3 C2 C3 C4 . . -175.91(14)
C1 C2 C3 C4 . . 1.8(2)
C2 C3 C4 C5 . . -0.9(2)
C3 C4 C5 N1 . . -0.3(2)
C1 N1 C5 C4 . . 0.6(2)
C6 C6 C7 C8 2_655 . -0.9(2)
C6 C7 C8 C8 . 2_655 -0.9(2)
C6 C7 C8 C9 . . -177.35(12)
C7 C8 C9 O1 . . 126.40(13)
C8 C8 C9 O1 2_655 . -50.01(19)
C7 C8 C9 O2 . . -51.38(16)
C8 C8 C9 O2 2_655 . 132.22(15)
