#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:57:23 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259315 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241572
loop_
_publ_author_name
'Lombard, Jean'
'Smith, Vincent J.'
'le Roex, Tanya'
'Haynes, Delia A.'
_publ_section_title
;
 Crystallisation of organic salts by sublimation: salt formation from the
 gas phase
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7826
_journal_page_last               7831
_journal_paper_doi               10.1039/D0CE01470B
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C10 H10 N2, 2(C2 H O4)'
_chemical_formula_sum            'C14 H12 N2 O8'
_chemical_formula_weight         336.26
_chemical_name_common            '4,4-bipyridinium bis(hydrogen oxalate)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                116.121(1)
_cell_angle_beta                 96.721(1)
_cell_angle_gamma                98.409(1)
_cell_formula_units_Z            1
_cell_length_a                   3.7614(3)
_cell_length_b                   9.8932(7)
_cell_length_c                   10.4498(7)
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.35
_cell_volume                     338.11(4)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_molecular_graphics
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5441
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.412
_diffrn_reflns_theta_min         2.217
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             174
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0409
_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)+(0.0767P)²+0.0605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1462
_reflns_number_total             1679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01470b2.cif
_cod_data_source_block           2a_RT
_cod_database_code               7241572
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3229(3) 0.12529(12) 0.42171(11) 0.0425(3) Uani 1 1 d . . . . .
H1 H 0.172(6) 0.056(2) 0.435(2) 0.058(6) Uiso 1 1 d . . . . .
O2 O 0.6625(3) 0.36032(12) 0.54678(12) 0.0467(3) Uani 1 1 d . . . . .
C3 C 0.4549(4) 0.25376(15) 0.54385(14) 0.0294(3) Uani 1 1 d . . . . .
C4 C 0.3274(4) 0.25881(14) 0.68123(13) 0.0268(3) Uani 1 1 d . . . . .
O5 O 0.1096(3) 0.14192(11) 0.66370(11) 0.0415(3) Uani 1 1 d . . . . .
O6 O 0.4552(3) 0.38024(11) 0.79675(11) 0.0364(3) Uani 1 1 d . . . . .
N7 N 0.9346(3) 0.63060(12) 0.84844(12) 0.0279(3) Uani 1 1 d . . . . .
H7 H 0.758(6) 0.523(3) 0.810(3) 0.068(7) Uiso 1 1 d . . . . .
C8 C 1.0442(4) 0.68630(15) 0.76027(15) 0.0357(3) Uani 1 1 d . . . . .
H8 H 0.970693 0.626659 0.659852 0.043 Uiso 1 1 calc R U . . .
C9 C 1.2661(4) 0.83206(15) 0.81813(14) 0.0312(3) Uani 1 1 d . . . . .
H9 H 1.339803 0.870800 0.756594 0.037 Uiso 1 1 calc R U . . .
C10 C 1.3800(3) 0.92120(12) 0.96810(12) 0.0209(3) Uani 1 1 d . . . . .
C11 C 1.2596(4) 0.85835(14) 1.05600(14) 0.0278(3) Uani 1 1 d . . . . .
H11 H 1.330802 0.914617 1.156784 0.033 Uiso 1 1 calc R U . . .
C12 C 1.0345(4) 0.71241(14) 0.99282(14) 0.0287(3) Uani 1 1 d . . . . .
H12 H 0.952329 0.671073 1.051376 0.034 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 111.8(14) . . ?
O2 C3 O1 121.10(12) . . ?
O2 C3 C4 122.69(12) . . ?
O1 C3 C4 116.22(11) . . ?
O5 C4 O6 127.51(12) . . ?
O5 C4 C3 116.53(11) . . ?
O6 C4 C3 115.96(11) . . ?
C12 N7 C8 121.73(11) . . ?
C12 N7 H7 115.4(14) . . ?
C8 N7 H7 122.8(14) . . ?
N7 C8 C9 120.11(12) . . ?
N7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 120.23(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 117.73(11) . . ?
C9 C10 C10 120.72(13) . 2_877 ?
C11 C10 C10 121.55(13) . 2_877 ?
C12 C11 C10 119.85(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N7 C12 C11 120.35(12) . . ?
N7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3152(15) . ?
O1 H1 0.89(2) . ?
O2 C3 1.2029(16) . ?
C3 C4 1.5488(19) . ?
C4 O5 1.2422(15) . ?
C4 O6 1.2449(15) . ?
N7 C12 1.3326(17) . ?
N7 C8 1.3387(18) . ?
N7 H7 1.04(2) . ?
C8 C9 1.3797(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.3902(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.3976(16) . ?
C10 C10 1.491(2) 2_877 ?
C11 C12 1.3818(17) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O5 0.89(2) 2.21(2) 2.6857(14) 112.7(17) . yes
O1 H1 O5 0.89(2) 1.84(2) 2.5993(14) 142(2) 2_556 yes
N7 H7 O6 1.04(2) 1.62(3) 2.6392(14) 163(2) . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 O5 179.28(13) . . . . ?
O1 C3 C4 O5 -0.65(19) . . . . ?
O2 C3 C4 O6 -0.6(2) . . . . ?
O1 C3 C4 O6 179.49(12) . . . . ?
C12 N7 C8 C9 -0.1(2) . . . . ?
N7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C8 C9 C10 C10 179.94(14) . . . 2_877 ?
C9 C10 C11 C12 -0.15(19) . . . . ?
C10 C10 C11 C12 179.41(13) 2_877 . . . ?
C8 N7 C12 C11 -0.6(2) . . . . ?
C10 C11 C12 N7 0.7(2) . . . . ?
