#------------------------------------------------------------------------------
#$Date: 2018-09-01 05:27:56 +0300 (Sat, 01 Sep 2018) $
#$Revision: 210295 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/98/1549872.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_1549872
loop_
_publ_author_name
'Dziuk, Błażej'
'Jezuita, Anna'
_publ_section_title
;
 2,2'-Bipyridin-1-ium hemioxalate oxalic acid monohydrate
;
_journal_coeditor_code           BT4073
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x181219
_journal_paper_doi               10.1107/S2414314618012191
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C10 H9 N2 +, 0.5C2 O4 2-, C2 H2 O4, H2 O'
_chemical_formula_moiety         'C10 H9 N2 +, 0.5(C2 O4 2-), C2 H2 O4, H2 O'
_chemical_formula_sum            'C13 H13 N2 O7'
_chemical_formula_weight         309.25
_chemical_name_common            '2,2'-Bipyridinium oxalate monohydrate'
_chemical_name_systematic
;
2,2'-Bipyridin-1-ium hemioxalate oxalic acid monohydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                85.545(5)
_cell_angle_beta                 86.177(5)
_cell_angle_gamma                75.248(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2618(4)
_cell_length_b                   8.9419(6)
_cell_length_c                   11.0001(7)
_cell_measurement_reflns_used    4712
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.996
_cell_measurement_theta_min      3.096
_cell_volume                     687.84(8)
_computing_cell_refinement
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4712
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.096
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.155
_refine_ls_extinction_coef       0.138(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2054
_reflns_number_total             2648
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4073sup1.cif
_cod_data_source_block           I
_cod_database_code               1549872
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
O O1 0.49365(11) 0.08583(10) 0.85141(7) 0.0386(2) Uani d 1
N N1 0.27452(14) 0.38740(12) 0.84585(10) 0.0408(3) Uani d 1
H H1 0.3370 0.2997 0.8775 0.049 Uiso calc 1
C C1 0.56889(16) 0.02093(13) 0.94780(10) 0.0294(3) Uani d 1
O O2 0.74212(11) -0.01433(10) 0.96493(8) 0.0465(3) Uani d 1
N N2 0.38268(15) 0.33461(12) 1.07479(10) 0.0406(3) Uani d 1
C C2 0.68092(17) 0.05604(14) 0.56545(11) 0.0349(3) Uani d 1
O O3 0.55452(14) 0.17018(12) 0.54737(8) 0.0594(3) Uani d 1
C C3 0.80116(17) -0.03224(15) 0.46116(10) 0.0339(3) Uani d 1
O O4 0.73101(12) -0.00942(11) 0.67194(7) 0.0470(3) Uani d 1
H H4 0.6457 0.0297 0.7370 0.056 Uiso d 1
C C4 0.21997(17) 0.50713(14) 0.91815(12) 0.0389(3) Uani d 1
C C5 0.11417(19) 0.64602(15) 0.86672(15) 0.0510(4) Uani d 1
H H5 0.0713 0.7310 0.9141 0.061 Uiso calc 1
O O5 0.91375(13) -0.15528(11) 0.47742(8) 0.0506(3) Uani d 1
C C6 0.0722(2) 0.65872(18) 0.74540(17) 0.0589(4) Uani d 1
H H6A 0.0006 0.7522 0.7113 0.071 Uiso calc 1
O O6 0.76264(12) 0.04452(10) 0.35664(7) 0.0453(3) Uani d 1
H H6 0.8398 -0.0028 0.2934 0.054 Uiso d 1
C C7 0.1354(2) 0.53431(19) 0.67463(15) 0.0591(4) Uani d 1
H H7 0.1098 0.5430 0.5923 0.071 Uiso calc 1
O O7 0.94612(12) -0.06711(10) 0.16511(7) 0.0440(3) Uani d 1
H H7A 1.0359 -0.0334 0.1317 0.053 Uiso d 1
H H7B 0.8673 -0.0478 0.0991 0.053 Uiso d 1
C C8 0.2373(2) 0.39662(18) 0.72765(14) 0.0524(4) Uani d 1
H H8 0.2802 0.3104 0.6817 0.063 Uiso calc 1
C C9 0.27939(17) 0.47844(14) 1.04566(12) 0.0377(3) Uani d 1
C C10 0.2316(2) 0.59226(17) 1.12833(15) 0.0546(4) Uani d 1
H H10 0.1623 0.6917 1.1047 0.066 Uiso calc 1
C C11 0.2885(2) 0.5560(2) 1.24680(16) 0.0633(4) Uani d 1
H H11 0.2570 0.6305 1.3043 0.076 Uiso calc 1
C C12 0.3922(2) 0.40849(19) 1.27819(14) 0.0563(4) Uani d 1
H H12 0.4313 0.3805 1.3574 0.068 Uiso calc 1
C C13 0.43656(19) 0.30303(16) 1.18919(13) 0.0481(4) Uani d 1
H H13 0.5086 0.2037 1.2104 0.058 Uiso calc 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C8 N1 C4 . 123.91(11)
C8 N1 H1 . 118.0
C4 N1 H1 . 118.0
O2 C1 O1 . 125.34(10)
O2 C1 C1 2_657 118.21(12)
O1 C1 C1 2_657 116.44(12)
C13 N2 C9 . 117.25(12)
O3 C2 O4 . 125.59(12)
O3 C2 C3 . 122.43(11)
O4 C2 C3 . 111.97(10)
O5 C3 O6 . 126.36(12)
O5 C3 C2 . 122.97(11)
O6 C3 C2 . 110.67(11)
C2 O4 H4 . 114.2
N1 C4 C5 . 117.27(13)
N1 C4 C9 . 116.89(11)
C5 C4 C9 . 125.84(13)
C6 C5 C4 . 120.14(15)
C6 C5 H5 . 119.9
C4 C5 H5 . 119.9
C7 C6 C5 . 120.36(13)
C7 C6 H6A . 119.8
C5 C6 H6A . 119.8
C3 O6 H6 . 112.1
C6 C7 C8 . 118.73(15)
C6 C7 H7 . 120.6
C8 C7 H7 . 120.6
H7A O7 H7B . 98.0
N1 C8 C7 . 119.56(14)
N1 C8 H8 . 120.2
C7 C8 H8 . 120.2
N2 C9 C10 . 122.62(13)
N2 C9 C4 . 115.25(12)
C10 C9 C4 . 122.13(12)
C9 C10 C11 . 118.92(14)
C9 C10 H10 . 120.5
C11 C10 H10 . 120.5
C12 C11 C10 . 118.99(14)
C12 C11 H11 . 120.5
C10 C11 H11 . 120.5
C11 C12 C13 . 118.18(15)
C11 C12 H12 . 120.9
C13 C12 H12 . 120.9
N2 C13 C12 . 124.03(13)
N2 C13 H13 . 118.0
C12 C13 H13 . 118.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2569(13)
N1 C8 . 1.3375(17)
N1 C4 . 1.3453(17)
N1 H1 . 0.8600
C1 O2 . 1.2401(13)
C1 C1 2_657 1.559(2)
N2 C13 . 1.3306(16)
N2 C9 . 1.3402(15)
C2 O3 . 1.1997(14)
C2 O4 . 1.2996(13)
C2 C3 . 1.5355(18)
C3 O5 . 1.2007(14)
C3 O6 . 1.3014(13)
O4 H4 . 0.9417
C4 C5 . 1.3841(17)
C4 C9 . 1.4791(19)
C5 C6 . 1.378(2)
C5 H5 . 0.9300
C6 C7 . 1.371(2)
C6 H6A . 0.9300
O6 H6 . 0.9224
C7 C8 . 1.3733(19)
C7 H7 . 0.9300
O7 H7A . 0.8379
O7 H7B . 0.9327
C8 H8 . 0.9300
C9 C10 . 1.380(2)
C10 C11 . 1.383(2)
C10 H10 . 0.9300
C11 C12 . 1.373(2)
C11 H11 . 0.9300
C12 C13 . 1.378(2)
C12 H12 . 0.9300
C13 H13 . 0.9300
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
O7 H7A O2 2_756 0.84 1.99 2.8192(12) 170.0
N1 H1 O1 . 0.86 1.99 2.7586(13) 147.9
O4 H4 O1 . 0.94 1.64 2.5795(11) 176.0
O4 H4 O2 . 0.94 2.62 3.2259(12) 122.4
O6 H6 O7 . 0.92 1.63 2.5467(11) 169.4
O7 H7B O2 1_554 0.93 1.75 2.6802(12) 173.7
C8 H8 O3 . 0.93 2.52 3.3132(18) 143.5
C10 H10 O7 1_466 0.93 2.43 3.2562(17) 147.6
C13 H13 O6 1_556 0.93 2.59 3.3876(16) 143.8

_cod_database_fobs_code 1549872
