#------------------------------------------------------------------------------
#$Date: 2023-11-10 21:21:08 +0200 (Fri, 10 Nov 2023) $
#$Revision: 287519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242024.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_2242024
loop_
_publ_author_name
'Zheng, Wen-Ni'
_publ_section_title
;
 Oxalic acid--pyridine-4-carbonitrile (1/2)
;
_journal_coeditor_code           YK2054
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1625
_journal_paper_doi               10.1107/S1600536812019137
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C6 H4 N2, C2 H2 O4'
_chemical_formula_moiety         '2(C6 H4 N2), C2 H2 O4'
_chemical_formula_sum            'C14 H10 N4 O4'
_chemical_formula_weight         298.26
_chemical_name_systematic
;
Oxalic acid--pyridine-4-carbonitrile (1/2)
;
_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                78.2580(10)
_cell_angle_beta                 85.3010(10)
_cell_angle_gamma                82.5470(10)
_cell_formula_units_Z            1
_cell_length_a                   3.6842(6)
_cell_length_b                   7.5816(5)
_cell_length_c                   12.45110(10)
_cell_measurement_reflns_used    1528
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.94
_cell_volume                     337.08(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 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      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku SCXmini Mercury2'
_diffrn_measurement_method       'ω scans CCD profile fitting'
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3634
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             154
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1528
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0358
_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)+(0.0650P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                1268
_reflns_number_total             1528
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2054sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2019-10-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C7 H5 N2 O2'
_cod_original_formula_weight         149.13
_cod_original_formula_moiety         'C6 H4 N2, 0.5(C2 H2 O4)'
_cod_original_formula_iupac          'C6 H4 N2, 0.5C2 H2 O4'
_cod_original_formula_units_Z            2
_cod_database_code               2242024
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_symmetry_multiplicity
O O1 0.8019(2) 0.10266(10) 0.37597(6) 0.0195(2) Uani d D 1 1
H H1 0.753(4) 0.2095(6) 0.3465(11) 0.029 Uiso d D 1 1
O O2 1.0250(2) 0.22804(10) 0.50208(6) 0.0196(2) Uani d . 1 1
N N1 0.6137(3) 0.43796(12) 0.27800(8) 0.0157(2) Uani d . 1 1
N N2 0.1419(3) 1.12502(13) 0.09513(8) 0.0207(2) Uani d . 1 1
C C4 0.5310(3) 0.75440(15) 0.28546(9) 0.0147(3) Uani d . 1 1
H H4A 0.5545 0.8461 0.3231 0.018 Uiso calc R 1 1
C C1 0.4759(3) 0.47781(15) 0.17793(9) 0.0158(3) Uani d . 1 1
H H1A 0.4592 0.3835 0.1417 0.019 Uiso calc R 1 1
C C3 0.3848(3) 0.79346(14) 0.18234(9) 0.0141(3) Uani d . 1 1
C C5 0.6404(3) 0.57355(15) 0.33014(9) 0.0152(3) Uani d . 1 1
H H5A 0.7362 0.5455 0.3992 0.018 Uiso calc R 1 1
C C2 0.3578(3) 0.65365(14) 0.12654(9) 0.0150(3) Uani d . 1 1
H H2A 0.2638 0.6777 0.0573 0.018 Uiso calc R 1 1
C C6 0.2532(3) 0.97886(14) 0.13355(9) 0.0161(3) Uani d . 1 1
C C7 0.9557(3) 0.09891(14) 0.46785(8) 0.0140(3) Uani 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_3
_geom_angle
C7 O1 H1 . 107.8(11)
C5 N1 C1 . 118.83(9)
C5 C4 C3 . 117.70(10)
C5 C4 H4A . 121.1
C3 C4 H4A . 121.1
N1 C1 C2 . 122.74(10)
N1 C1 H1A . 118.6
C2 C1 H1A . 118.6
C4 C3 C2 . 120.13(10)
C4 C3 C6 . 120.12(9)
C2 C3 C6 . 119.74(10)
N1 C5 C4 . 122.85(10)
N1 C5 H5A . 118.6
C4 C5 H5A . 118.6
C1 C2 C3 . 117.75(10)
C1 C2 H2A . 121.1
C3 C2 H2A . 121.1
N2 C6 C3 . 178.67(12)
O2 C7 O1 . 126.63(10)
O2 C7 C7 2_756 121.93(12)
O1 C7 C7 2_756 111.44(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.3113(12)
O1 H1 . 0.822(2)
O2 C7 . 1.2075(13)
N1 C5 . 1.3403(14)
N1 C1 . 1.3462(13)
N2 C6 . 1.1503(14)
C4 C5 . 1.3910(15)
C4 C3 . 1.3940(14)
C4 H4A . 0.9300
C1 C2 . 1.3871(15)
C1 H1A . 0.9300
C3 C2 . 1.3981(15)
C3 C6 . 1.4505(14)
C5 H5A . 0.9300
C2 H2A . 0.9300
C7 C7 2_756 1.557(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
O1 H1 N1 . 0.822(2) 1.797(3) 2.6173(12) 175.5(15)
C4 H4A O1 1_565 0.93 2.480 3.3640(13) 159.9

_cod_database_fobs_code 2242024
_cod_duplicate_entry 2235319
