#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224748.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_2224748
loop_
_publ_author_name
'Han, Lu'
'Luo, Huan-Mian'
'Meng, Qiu-Hui'
'Luo, Yi-Fan'
'Zeng, Rong-Hua'
_publ_section_title
;
 4-(4-Pyridyl)pyridinium 3',4,4'-tricarboxybiphenyl-3-carboxylate
 dihydrate
;
_journal_coeditor_code           RZ2388
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o68
_journal_page_last               o69
_journal_paper_doi               10.1107/S1600536809050831
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H9 N2 +, C16 H9 O8 -, 2H2 O'
_chemical_formula_moiety         'C10 H9 N2 +, C16 H9 O8 -, 2(H2 O)'
_chemical_formula_sum            'C26 H22 N2 O10'
_chemical_formula_weight         522.46
_chemical_name_systematic
;
4-(4-Pyridyl)pyridinium 3',4,4'-tricarboxybiphenyl-3-carboxylate 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           SHELXL-97
_cell_angle_alpha                90.7920(11)
_cell_angle_beta                 106.4850(13)
_cell_angle_gamma                107.1180(15)
_cell_formula_units_Z            1
_cell_length_a                   7.1955(8)
_cell_length_b                   8.9350(10)
_cell_length_c                   9.8847(11)
_cell_measurement_reflns_used    2061
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.40
_cell_volume                     579.09(11)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2990
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.252
_refine_ls_extinction_coef       0.071(9)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0386
_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)+(0.0562P)²+0.2257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1818
_reflns_number_total             2050
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2388.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2224748
_cod_database_fobs_code          2224748
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4881(3) 1.01415(19) 0.18864(18) 0.0405(4) Uani d . 1 . .
H H1 0.5318 1.1230 0.2095 0.049 Uiso calc R 1 . .
C C2 0.4740(2) 0.94960(17) 0.05542(16) 0.0321(4) Uani d . 1 . .
C C3 0.4103(3) 0.78512(18) 0.03012(17) 0.0361(4) Uani d . 1 . .
H H3 0.4008 0.7393 -0.0576 0.043 Uiso calc R 1 . .
C C4 0.3611(2) 0.68843(17) 0.13133(17) 0.0333(4) Uani d . 1 . .
C C5 0.3102(3) 0.51258(19) 0.09704(18) 0.0397(4) Uani d . 1 . .
C C6 0.3725(2) 0.75584(18) 0.26291(16) 0.0344(4) Uani d . 1 . .
C C7 0.3003(3) 0.65386(19) 0.36673(18) 0.0389(4) Uani d . 1 . .
C C8 0.4384(3) 0.91911(19) 0.28990(18) 0.0407(4) Uani d . 1 . .
H H8 0.4490 0.9650 0.3779 0.049 Uiso calc R 1 . .
C C9 0.9236(3) -0.1318(2) 0.19327(19) 0.0447(4) Uani d . 1 . .
H H9 0.8726 -0.2254 0.1336 0.054 Uiso calc R 1 . .
C C10 0.9232(3) -0.13691(19) 0.33220(18) 0.0412(4) Uani d . 1 . .
H H10 0.8722 -0.2331 0.3647 0.049 Uiso calc R 1 . .
C C11 0.9987(2) 0.00096(18) 0.42445(17) 0.0351(4) Uani d . 1 . .
C C12 1.0714(3) 0.1400(2) 0.3674(2) 0.0490(5) Uani d . 1 . .
H H12 1.1234 0.2355 0.4243 0.059 Uiso calc R 1 . .
C C13 1.0666(3) 0.1367(2) 0.2273(2) 0.0524(5) Uani d . 1 . .
H H13 1.1151 0.2311 0.1914 0.063 Uiso calc R 1 . .
N N1 0.9947(2) 0.00297(17) 0.14119(15) 0.0428(4) Uani d D 1 . .
H H1A 0.997(7) 0.004(5) 0.049(2) 0.051 Uiso d PD 0.50 . .
O O1 0.4404(2) 0.44851(15) 0.14281(16) 0.0572(4) Uani d . 1 . .
O O3 0.1949(2) 0.51807(15) 0.33352(14) 0.0596(4) Uani d . 1 . .
O O4 0.3524(3) 0.72538(16) 0.49433(14) 0.0647(5) Uani d D 1 . .
H H4A 0.3092 0.6627 0.5465 0.097 Uiso calc RD 1 . .
O O1W 0.2145(3) 0.5413(2) 0.66452(17) 0.0799(6) Uani d . 1 . .
H H1W 0.3004 0.5290 0.7356 0.120 Uiso d R 1 . .
H H2W 0.1031 0.5241 0.6817 0.120 Uiso d R 1 . .
O O2 0.1336(2) 0.43770(14) 0.01377(15) 0.0520(4) Uani d D 1 . .
H H2A 0.040(8) 0.490(8) 0.001(8) 0.078 Uiso d PD 0.50 . .
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
_geom_angle_publ_flag
C8 C1 C2 . . 121.02(15) ?
C8 C1 H1 . . 119.5 ?
C2 C1 H1 . . 119.5 ?
C1 C2 C3 . . 117.26(15) ?
C1 C2 C2 . 2_675 121.74(17) ?
C3 C2 C2 . 2_675 121.00(17) ?
C4 C3 C2 . . 122.24(15) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C4 C6 . . 119.43(14) ?
C3 C4 C5 . . 117.83(14) ?
C6 C4 C5 . . 122.62(14) ?
O1 C5 O2 . . 122.14(16) ?
O1 C5 C4 . . 119.75(16) ?
O2 C5 C4 . . 117.99(15) ?
C8 C6 C4 . . 118.80(15) ?
C8 C6 C7 . . 121.15(14) ?
C4 C6 C7 . . 119.90(14) ?
O3 C7 O4 . . 123.27(16) ?
O3 C7 C6 . . 122.33(15) ?
O4 C7 C6 . . 114.33(14) ?
C1 C8 C6 . . 121.24(15) ?
C1 C8 H8 . . 119.4 ?
C6 C8 H8 . . 119.4 ?
N1 C9 C10 . . 122.24(16) ?
N1 C9 H9 . . 118.9 ?
C10 C9 H9 . . 118.9 ?
C9 C10 C11 . . 120.39(16) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 116.23(16) ?
C10 C11 C11 . 2_756 121.63(18) ?
C12 C11 C11 . 2_756 122.14(18) ?
C13 C12 C11 . . 120.36(16) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
N1 C13 C12 . . 122.31(17) ?
N1 C13 H13 . . 118.8 ?
C12 C13 H13 . . 118.8 ?
C13 N1 C9 . . 118.47(15) ?
C13 N1 H1A . . 120(3) ?
C9 N1 H1A . . 121(3) ?
C7 O4 H4A . . 109.5 ?
H1W O1W H2W . . 109.1 ?
C5 O2 H2A . . 115(5) ?
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
C1 C8 . 1.378(2) ?
C1 C2 . 1.395(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.400(2) ?
C2 C2 2_675 1.488(3) ?
C3 C4 . 1.385(2) ?
C3 H3 . 0.9300 ?
C4 C6 . 1.397(2) ?
C4 C5 . 1.514(2) ?
C5 O1 . 1.222(2) ?
C5 O2 . 1.277(2) ?
C6 C8 . 1.391(2) ?
C6 C7 . 1.484(2) ?
C7 O3 . 1.209(2) ?
C7 O4 . 1.307(2) ?
C8 H8 . 0.9300 ?
C9 N1 . 1.334(2) ?
C9 C10 . 1.375(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.392(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.392(2) ?
C11 C11 2_756 1.489(3) ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 N1 . 1.334(2) ?
C13 H13 . 0.9300 ?
N1 H1A . 0.921(18) ?
O4 H4A . 0.8200 ?
O1W H1W . 0.8263 ?
O1W H2W . 0.8370 ?
O2 H2A . 0.911(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
N1 H1A N1 2_755 0.921(18) 1.894(19) 2.814(3) 177(4)
O4 H4A O1W . 0.82 1.75 2.5657(19) 175.5
O1W H1W O1 2_666 0.83 1.86 2.642(2) 157.0
O1W H2W O3 2_566 0.84 2.03 2.841(2) 164.7
O2 H2A O2 2_565 0.911(19) 1.54(2) 2.446(3) 173(7)
C3 H3 O1 2_665 0.93 2.54 3.270(2) 135.4
C13 H13 O2 1_655 0.93 2.57 3.448(2) 158.6
C9 H9 O2 2_655 0.93 2.36 3.246(2) 159.6
