#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225216.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_2225216
loop_
_publ_author_name
'Cui, Li-Jing'
'Chen, Xin-Yuan'
_publ_section_title
;
 Isonicotinonitrile--benzoic acid (1/1)
;
_journal_coeditor_code           DN2532
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o722
_journal_paper_doi               10.1107/S1600536810003442
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H4 N2, C7 H6 O2'
_chemical_formula_moiety         'C6 H4 N2, C7 H6 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_chemical_name_systematic
;
Isonicotinonitrile--benzoic acid (1/1)
;
_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                85.26(3)
_cell_angle_beta                 76.44(3)
_cell_angle_gamma                62.79(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4274(15)
_cell_length_b                   7.7389(15)
_cell_length_c                   11.668(2)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.16
_cell_volume                     579.6(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       ω
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6025
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0589
_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)+(0.0699P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                1346
_reflns_number_total             2646
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2532.cif
_cod_data_source_block           I
_cod_database_code               2225216
_cod_database_fobs_code          2225216
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
O O1 0.3710(2) 0.8106(2) 0.47118(13) 0.0701(5) Uani d . 1 . .
H H1 0.4865 0.8033 0.4202 0.105 Uiso d R 1 . .
O O2 0.5897(2) 0.6595(2) 0.58797(14) 0.0824(5) Uani d . 1 . .
N N1 0.7138(3) 0.8082(2) 0.32068(15) 0.0578(5) Uani d . 1 . .
C C1 0.2396(3) 0.7201(3) 0.65759(17) 0.0491(5) Uani d . 1 . .
C C7 0.4176(3) 0.7263(3) 0.56976(18) 0.0529(5) Uani d . 1 . .
C C9 1.0739(3) 0.7156(3) 0.29472(19) 0.0615(6) Uani d . 1 . .
H H9 1.1922 0.6611 0.3257 0.074 Uiso calc R 1 . .
C C6 0.0455(3) 0.7920(3) 0.63365(19) 0.0595(6) Uani d . 1 . .
H H6 0.0224 0.8473 0.5614 0.071 Uiso calc R 1 . .
C C11 0.9010(3) 0.8656(3) 0.13992(18) 0.0584(6) Uani d . 1 . .
H H11 0.9012 0.9140 0.0643 0.070 Uiso calc R 1 . .
C C8 0.8875(3) 0.7304(3) 0.35995(18) 0.0610(6) Uani d . 1 . .
H H8 0.8827 0.6831 0.4359 0.073 Uiso calc R 1 . .
C C10 1.0797(3) 0.7841(3) 0.18209(18) 0.0503(5) Uani d . 1 . .
C C2 0.2716(3) 0.6398(3) 0.76576(18) 0.0616(6) Uani d . 1 . .
H H2 0.4022 0.5920 0.7825 0.074 Uiso calc R 1 . .
C C12 0.7228(3) 0.8737(3) 0.21192(19) 0.0612(6) Uani d . 1 . .
H H12 0.6022 0.9278 0.1832 0.073 Uiso calc R 1 . .
C C13 1.2710(3) 0.7712(3) 0.1076(2) 0.0642(6) Uani d . 1 . .
C C5 -0.1155(4) 0.7817(3) 0.7179(2) 0.0717(7) Uani d . 1 . .
H H5 -0.2463 0.8285 0.7015 0.086 Uiso calc R 1 . .
N N2 1.4213(3) 0.7615(3) 0.04740(19) 0.0934(8) Uani d . 1 . .
C C4 -0.0823(4) 0.7023(3) 0.8254(2) 0.0762(7) Uani d . 1 . .
H H4 -0.1913 0.6979 0.8821 0.091 Uiso calc R 1 . .
C C3 0.1099(4) 0.6302(3) 0.8492(2) 0.0719(7) Uani d . 1 . .
H H3 0.1325 0.5747 0.9215 0.086 Uiso calc R 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
_geom_angle_publ_flag
C7 O1 H1 . . 110.0 ?
C12 N1 C8 . . 117.62(18) ?
C6 C1 C2 . . 119.62(19) ?
C6 C1 C7 . . 121.69(18) ?
C2 C1 C7 . . 118.69(18) ?
O2 C7 O1 . . 123.03(18) ?
O2 C7 C1 . . 122.61(18) ?
O1 C7 C1 . . 114.36(18) ?
C8 C9 C10 . . 117.7(2) ?
C8 C9 H9 . . 121.2 ?
C10 C9 H9 . . 121.2 ?
C1 C6 C5 . . 119.7(2) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C12 C11 C10 . . 118.44(19) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
N1 C8 C9 . . 123.7(2) ?
N1 C8 H8 . . 118.2 ?
C9 C8 H8 . . 118.2 ?
C9 C10 C11 . . 119.40(19) ?
C9 C10 C13 . . 120.88(19) ?
C11 C10 C13 . . 119.72(19) ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
N1 C12 C11 . . 123.1(2) ?
N1 C12 H12 . . 118.4 ?
C11 C12 H12 . . 118.4 ?
N2 C13 C10 . . 179.1(3) ?
C4 C5 C6 . . 120.2(2) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C3 C4 C5 . . 120.2(2) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C3 C2 . . 120.0(2) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
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
O1 C7 . 1.313(2) ?
O1 H1 . 0.9025 ?
O2 C7 . 1.205(2) ?
N1 C12 . 1.325(3) ?
N1 C8 . 1.326(3) ?
C1 C6 . 1.377(3) ?
C1 C2 . 1.383(3) ?
C1 C7 . 1.488(3) ?
C9 C8 . 1.373(3) ?
C9 C10 . 1.375(3) ?
C9 H9 . 0.9300 ?
C6 C5 . 1.388(3) ?
C6 H6 . 0.9300 ?
C11 C12 . 1.368(3) ?
C11 C10 . 1.376(3) ?
C11 H11 . 0.9300 ?
C8 H8 . 0.9300 ?
C10 C13 . 1.446(3) ?
C2 C3 . 1.384(3) ?
C2 H2 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 N2 . 1.144(3) ?
C5 C4 . 1.375(3) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.363(3) ?
C4 H4 . 0.9300 ?
C3 H3 . 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
O1 H1 N1 . 0.90 1.83 2.726(2) 175.5
C8 H8 O2 . 0.93 2.53 3.222(3) 131.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656014
