#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/46/2214675.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_2214675
loop_
_publ_author_name
'Ibrahim Uçar'
'Ahmet  Bulut'
'Orhan Büyükgüngör'
_publ_section_title
;
 Bis[2-(2-pyridylamino)pyridinium] squarate dihydrate
;
_journal_coeditor_code           HB2459
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3377
_journal_page_last               o3377
_journal_paper_doi               10.1107/S160053680703139X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '2C10 H10 N3 + , C4 O4 2- , 2H2 O'
_chemical_formula_moiety         '2C10 H10 N3 + , C4 O4 2- , 2H2 O'
_chemical_formula_sum            'C24 H24 N6 O6'
_chemical_formula_weight         492.50
_chemical_name_systematic
;
Bis[2-(2-pyridylamino)pyridinium] squarate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                74.34(3)
_cell_angle_beta                 87.26(2)
_cell_angle_gamma                71.85(4)
_cell_formula_units_Z            1
_cell_length_a                   8.072(2)
_cell_length_b                   8.493(3)
_cell_length_c                   8.833(2)
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.59
_cell_volume                     553.6(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'WinGX  (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6024
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.62
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             258.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.079(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0435
_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)+(0.0672P)²+0.0549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                2027
_reflns_number_total             2634
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2459.cif
_cod_data_source_block           I
_cod_database_code               2214675
_cod_database_fobs_code          2214675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.1787(2) -0.0003(2) 0.20087(18) 0.0525(4) Uani d . 1
H H1 0.1856 0.0817 0.1086 0.063 Uiso calc R 1
C C2 0.1266(2) -0.1349(2) 0.1916(2) 0.0562(4) Uani d . 1
H H2 0.1019 -0.1468 0.0942 0.067 Uiso calc R 1
C C3 0.1108(2) -0.2539(2) 0.3286(2) 0.0518(4) Uani d . 1
H H3 0.0732 -0.3457 0.3243 0.062 Uiso calc R 1
C C4 0.15007(19) -0.23637(18) 0.46912(19) 0.0440(3) Uani d . 1
H H4 0.1387 -0.3145 0.5625 0.053 Uiso calc R 1
C C5 0.20815(17) -0.09827(17) 0.47064(16) 0.0372(3) Uani d . 1
C C6 0.30437(17) 0.05217(16) 0.63285(16) 0.0367(3) Uani d . 1
C C7 0.3349(2) 0.05677(19) 0.78463(17) 0.0436(3) Uani d . 1
H H7 0.3259 -0.0310 0.8710 0.052 Uiso calc R 1
C C8 0.3784(2) 0.1927(2) 0.8039(2) 0.0519(4) Uani d . 1
H H8 0.3975 0.1990 0.9048 0.062 Uiso calc R 1
C C9 0.3944(2) 0.3214(2) 0.6754(2) 0.0535(4) Uani d . 1
H H9 0.4246 0.4142 0.6884 0.064 Uiso calc R 1
C C10 0.3654(2) 0.30938(19) 0.5314(2) 0.0495(4) Uani d . 1
H H10 0.3760 0.3954 0.4440 0.059 Uiso calc R 1
C C11 0.38626(17) 0.57812(16) -0.05777(14) 0.0344(3) Uani d . 1
C C12 0.43433(18) 0.42336(17) 0.07214(15) 0.0371(3) Uani d . 1
N N1 0.22009(17) 0.01827(15) 0.33788(14) 0.0430(3) Uani d . 1
N N2 0.25340(16) -0.07779(14) 0.60874(13) 0.0392(3) Uani d . 1
H H2A 0.2493 -0.1574 0.6917 0.047 Uiso calc R 1
N N3 0.32133(16) 0.17666(14) 0.50969(14) 0.0415(3) Uani d . 1
O O1 0.24748(14) 0.67258(13) -0.12805(13) 0.0494(3) Uani d . 1
O O2 0.35589(16) 0.33000(16) 0.15768(15) 0.0639(4) Uani d . 1
O O3 0.0043(2) 0.4689(2) 0.2011(2) 0.0858(5) Uani d D 1
H H3A -0.058(3) 0.426(3) 0.163(3) 0.088(8) Uiso d D 1
H H3B 0.105(3) 0.435(3) 0.171(3) 0.095(8) Uiso d D 1
H H1A 0.282(3) 0.132(2) 0.392(2) 0.064(5) 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'
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
N1 C1 C2 . . 122.13(16)
N1 C1 H1 . . 118.9
C2 C1 H1 . . 118.9
C1 C2 C3 . . 119.11(15)
C1 C2 H2 . . 120.4
C3 C2 H2 . . 120.4
C4 C3 C2 . . 119.71(15)
C4 C3 H3 . . 120.1
C2 C3 H3 . . 120.1
C3 C4 C5 . . 118.45(15)
C3 C4 H4 . . 120.8
C5 C4 H4 . . 120.8
N1 C5 N2 . . 117.87(12)
N1 C5 C4 . . 121.56(13)
N2 C5 C4 . . 120.57(13)
N3 C6 N2 . . 119.44(13)
N3 C6 C7 . . 120.33(13)
N2 C6 C7 . . 120.22(12)
C8 C7 C6 . . 118.39(14)
C8 C7 H7 . . 120.8
C6 C7 H7 . . 120.8
C7 C8 C9 . . 120.69(15)
C7 C8 H8 . . 119.7
C9 C8 H8 . . 119.7
C10 C9 C8 . . 118.38(14)
C10 C9 H9 . . 120.8
C8 C9 H9 . . 120.8
C9 C10 N3 . . 121.90(15)
C9 C10 H10 . . 119.0
N3 C10 H10 . . 119.0
O1 C11 C12 . 2_665 134.52(12)
O1 C11 C12 . . 134.30(13)
C12 C11 C12 2_665 . 91.18(11)
O1 C11 C11 . 2_665 179.69(14)
C12 C11 C11 2_665 2_665 45.73(8)
C12 C11 C11 . 2_665 45.45(8)
O2 C12 C11 . 2_665 135.38(13)
O2 C12 C11 . . 135.79(14)
C11 C12 C11 2_665 . 88.82(11)
C1 N1 C5 . . 118.99(13)
C1 N1 H1A . . 138.1(8)
C5 N1 H1A . . 102.9(8)
C5 N2 C6 . . 128.48(12)
C5 N2 H2A . . 115.8
C6 N2 H2A . . 115.8
C6 N3 C10 . . 120.29(13)
C6 N3 H1A . . 103.3(8)
C10 N3 H1A . . 136.4(8)
H3A O3 H3B . . 108(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.333(2)
C1 C2 . 1.358(3)
C1 H1 . 0.9300
C2 C3 . 1.382(3)
C2 H2 . 0.9300
C3 C4 . 1.353(2)
C3 H3 . 0.9300
C4 C5 . 1.395(2)
C4 H4 . 0.9300
C5 N1 . 1.3366(18)
C5 N2 . 1.3596(18)
C6 N3 . 1.3323(18)
C6 N2 . 1.3605(18)
C6 C7 . 1.388(2)
C7 C8 . 1.360(2)
C7 H7 . 0.9300
C8 C9 . 1.380(2)
C8 H8 . 0.9300
C9 C10 . 1.340(2)
C9 H9 . 0.9300
C10 N3 . 1.3441(19)
C10 H10 . 0.9300
C11 O1 . 1.2335(17)
C11 C12 2_665 1.4440(19)
C11 C12 . 1.4511(17)
C12 O2 . 1.2426(16)
C12 C11 2_665 1.4440(19)
N1 H1A . 1.415(19)
N2 H2A . 0.8600
N3 H1A . 1.28(2)
O3 H3A . 0.832(17)
O3 H3B . 0.834(17)
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
N2 H2A O1 1_546 0.86 1.84 2.7008(17) 178.0
O3 H3A O1 2_565 0.832(17) 2.031(18) 2.8382(19) 163(2)
N3 H1A N1 . 1.28(2) 1.415(19) 2.5857(18) 147.8(15)
O3 H3B O2 . 0.834(17) 1.951(18) 2.765(2) 165(3)
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
N1 C1 C2 C3 . . 2.0(3)
C1 C2 C3 C4 . . -1.1(2)
C2 C3 C4 C5 . . -0.9(2)
C3 C4 C5 N1 . . 2.1(2)
C3 C4 C5 N2 . . -178.34(13)
N3 C6 C7 C8 . . 1.4(2)
N2 C6 C7 C8 . . -177.22(14)
C6 C7 C8 C9 . . -1.0(2)
C7 C8 C9 C10 . . 0.3(3)
C8 C9 C10 N3 . . 0.1(3)
O1 C11 C12 O2 . . 0.8(3)
C12 C11 C12 O2 2_665 . -178.9(2)
C11 C11 C12 O2 2_665 . -178.9(2)
O1 C11 C12 C11 . 2_665 179.75(19)
C12 C11 C12 C11 2_665 2_665 0.0
C2 C1 N1 C5 . . -0.8(2)
N2 C5 N1 C1 . . 179.13(13)
C4 C5 N1 C1 . . -1.3(2)
N1 C5 N2 C6 . . 2.9(2)
C4 C5 N2 C6 . . -176.63(13)
N3 C6 N2 C5 . . -2.9(2)
C7 C6 N2 C5 . . 175.82(13)
N2 C6 N3 C10 . . 177.57(13)
C7 C6 N3 C10 . . -1.1(2)
C9 C10 N3 C6 . . 0.3(2)
