#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/34/2223477.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_2223477
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 Pyridine-3-carbonitrile--chloranilic acid--acetonitrile (2/1/2)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2467
_journal_paper_doi               10.1107/S1600536809036605
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C6 H4 N2, C6 H2 Cl2 O4, 2C2 H3 N'
_chemical_formula_moiety         '2(C6 H4 N2), C6 H2 Cl2 O4, 2(C2 H3 N)'
_chemical_formula_sum            'C22 H16 Cl2 N6 O4'
_chemical_formula_weight         499.31
_chemical_name_common
;
Pyridine-3-carbonitrile--chloranilic acid (2/1) acetonitrile disolvate
;
_chemical_name_systematic
;
Pyridine-3-carbonitrile--chloranilic acid--acetonitrile (2/1/2)
;
_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
_cell_angle_alpha                105.302(4)
_cell_angle_beta                 90.0058(14)
_cell_angle_gamma                90.847(5)
_cell_formula_units_Z            1
_cell_length_a                   3.91269(16)
_cell_length_b                   10.8937(9)
_cell_length_c                   13.5966(5)
_cell_measurement_reflns_used    6412
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     558.93(6)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7721
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256.00
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0348
_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)+(0.0495P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2592
_reflns_number_total             3232
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2901.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C22 H16 Cl2 N6 O4 '
_cod_database_code               2223477
_cod_database_fobs_code          2223477
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
Cl Cl1 0.74850(9) -0.11634(3) 0.17747(2) 0.02647(10) Uani d . 1 . .
O O1 1.1404(3) -0.24034(9) -0.00816(7) 0.0278(2) Uani d . 1 . .
O O2 0.6357(3) 0.14675(10) 0.16065(7) 0.0294(2) Uani d . 1 . .
N N1 0.4384(3) 0.38133(11) 0.18840(9) 0.0268(2) Uani d . 1 . .
N N2 0.2005(4) 0.63890(12) 0.52232(10) 0.0347(3) Uani d . 1 . .
N N3 -0.2867(4) 0.85277(13) 0.41743(11) 0.0400(3) Uani d . 1 . .
C C1 1.0708(3) -0.12968(12) -0.00163(9) 0.0213(2) Uani d . 1 . .
C C2 0.8789(3) -0.04984(12) 0.08193(9) 0.0208(2) Uani d . 1 . .
C C3 0.8076(3) 0.07272(12) 0.08605(9) 0.0215(2) Uani d . 1 . .
C C4 0.3922(4) 0.43073(12) 0.28796(10) 0.0254(3) Uani d . 1 . .
H H4 0.4423 0.3805 0.3335 0.031 Uiso calc R 1 . .
C C5 0.2725(3) 0.55390(12) 0.32762(10) 0.0233(3) Uani d . 1 . .
C C6 0.1973(4) 0.62808(13) 0.26185(10) 0.0265(3) Uani d . 1 . .
H H6 0.1169 0.7124 0.2871 0.032 Uiso calc R 1 . .
C C7 0.2431(4) 0.57525(13) 0.15812(11) 0.0281(3) Uani d . 1 . .
H H7 0.1922 0.6227 0.1106 0.034 Uiso calc R 1 . .
C C8 0.3640(4) 0.45244(13) 0.12482(10) 0.0270(3) Uani d . 1 . .
H H8 0.3956 0.4171 0.0537 0.032 Uiso calc R 1 . .
C C9 0.2324(4) 0.60218(13) 0.43620(10) 0.0263(3) Uani d . 1 . .
C C10 -0.2753(4) 0.87366(14) 0.50394(12) 0.0310(3) Uani d . 1 . .
C C11 -0.2586(4) 0.90013(16) 0.61421(12) 0.0365(3) Uani d . 1 . .
H H11A -0.0933 0.8436 0.6332 0.055 Uiso calc R 1 . .
H H11B -0.4846 0.8857 0.6406 0.055 Uiso calc R 1 . .
H H11C -0.1869 0.9889 0.6432 0.055 Uiso calc R 1 . .
H H2 0.596(7) 0.226(3) 0.152(2) 0.082(9) Uiso d . 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'
Cl Cl 0.1484 0.1585 '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
C3 O2 H2 . . 114.0(17) ?
C4 N1 C8 . . 118.49(11) ?
O1 C1 C2 . . 123.93(12) ?
O1 C1 C3 . 2_755 117.75(11) ?
C2 C1 C3 . 2_755 118.31(10) ?
C3 C2 C1 . . 121.90(11) ?
C3 C2 Cl1 . . 120.77(10) ?
C1 C2 Cl1 . . 117.33(9) ?
O2 C3 C2 . . 123.08(12) ?
O2 C3 C1 . 2_755 117.14(11) ?
C2 C3 C1 . 2_755 119.78(11) ?
N1 C4 C5 . . 122.13(12) ?
N1 C4 H4 . . 118.9 ?
C5 C4 H4 . . 118.9 ?
C6 C5 C4 . . 119.46(12) ?
C6 C5 C9 . . 121.20(12) ?
C4 C5 C9 . . 119.34(12) ?
C7 C6 C5 . . 117.96(12) ?
C7 C6 H6 . . 121.0 ?
C5 C6 H6 . . 121.0 ?
C8 C7 C6 . . 119.07(12) ?
C8 C7 H7 . . 120.5 ?
C6 C7 H7 . . 120.5 ?
N1 C8 C7 . . 122.88(13) ?
N1 C8 H8 . . 118.6 ?
C7 C8 H8 . . 118.6 ?
N2 C9 C5 . . 179.14(15) ?
N3 C10 C11 . . 179.69(18) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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
Cl1 C2 . 1.7200(13) ?
O1 C1 . 1.2201(15) ?
O2 C3 . 1.3099(15) ?
O2 H2 . 0.91(3) ?
N1 C4 . 1.3316(17) ?
N1 C8 . 1.3387(18) ?
N2 C9 . 1.1406(18) ?
N3 C10 . 1.138(2) ?
C1 C2 . 1.4521(17) ?
C1 C3 2_755 1.5153(18) ?
C2 C3 . 1.3546(17) ?
C3 C1 2_755 1.5153(18) ?
C4 C5 . 1.3955(18) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3884(18) ?
C5 C9 . 1.4399(18) ?
C6 C7 . 1.3883(19) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3848(19) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C10 C11 . 1.451(2) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
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
O2 H2 N1 . 0.92(3) 1.75(3) 2.6111(17) 154(3)
O2 H2 O1 2_755 0.92(3) 2.25(3) 2.6824(14) 108(2)
C4 H4 N2 2_666 0.95 2.46 3.292(2) 146
C6 H6 N3 . 0.95 2.57 3.385(2) 144
C7 H7 O1 1_465 0.95 2.48 3.4248(18) 172
C11 H11A N2 . 0.98 2.62 3.341(2) 130
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 179.96(13) ?
C3 C1 C2 C3 2_755 . . . -0.1(2) ?
O1 C1 C2 Cl1 . . . . 0.78(18) ?
C3 C1 C2 Cl1 2_755 . . . -179.23(9) ?
C1 C2 C3 O2 . . . . -179.86(12) ?
Cl1 C2 C3 O2 . . . . -0.72(19) ?
C1 C2 C3 C1 . . . 2_755 0.1(2) ?
Cl1 C2 C3 C1 . . . 2_755 179.21(9) ?
C8 N1 C4 C5 . . . . -0.6(2) ?
N1 C4 C5 C6 . . . . 0.2(2) ?
N1 C4 C5 C9 . . . . -179.19(13) ?
C4 C5 C6 C7 . . . . 0.4(2) ?
C9 C5 C6 C7 . . . . 179.82(13) ?
C5 C6 C7 C8 . . . . -0.6(2) ?
C4 N1 C8 C7 . . . . 0.4(2) ?
C6 C7 C8 N1 . . . . 0.3(2) ?
