#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240792.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_2240792
loop_
_publ_author_name
'Kang, Gihaeng'
'Kim, Tae Ho'
'Jeon, Youngeun'
'Kim, Jineun'
_publ_section_title
;
 Crystal structure of [1,1'-biphenyl]-2,2'-dicarbonitrile
;
_journal_coeditor_code           WM5163
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o430
_journal_paper_doi               10.1107/S2056989015009561
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H8 N2'
_chemical_formula_moiety         'C14 H8 N2'
_chemical_formula_sum            'C14 H8 N2'
_chemical_formula_weight         204.22
_chemical_name_systematic
;
[1,1'-Biphenyl]-2,2'-dicarbonitrile
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.630(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7839(9)
_cell_length_b                   3.9451(2)
_cell_length_c                   16.6079(9)
_cell_measurement_reflns_used    1375
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.25
_cell_volume                     1012.93(10)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4708
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0420
_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)+(0.0584P)²+0.5212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                988
_reflns_number_total             1157
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm5163sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1012.93(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2240792
_cod_database_fobs_code          2240792
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
N N1 0.58879(7) 0.3650(3) 0.08819(7) 0.0323(3) Uani d . 1 1
C C1 0.53155(8) 0.2522(3) 0.11172(7) 0.0233(3) Uani d . 1 1
C C2 0.45640(7) 0.1152(3) 0.13725(7) 0.0206(3) Uani d . 1 1
C C3 0.37963(8) 0.1099(3) 0.07828(7) 0.0244(3) Uani d . 1 1
H H3 0.3791 0.1894 0.0242 0.029 Uiso calc R 1 1
C C4 0.30457(8) -0.0108(3) 0.09854(8) 0.0273(3) Uani d . 1 1
H H4 0.2522 -0.0139 0.0586 0.033 Uiso calc R 1 1
C C5 0.30609(8) -0.1274(3) 0.17741(8) 0.0257(3) Uani d . 1 1
H H5 0.2545 -0.2117 0.1914 0.031 Uiso calc R 1 1
C C6 0.38225(8) -0.1224(3) 0.23640(7) 0.0231(3) Uani d . 1 1
H H6 0.3819 -0.2037 0.2902 0.028 Uiso calc R 1 1
C C7 0.45930(7) -0.0004(3) 0.21832(7) 0.0196(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'
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
N1 C1 C2 . 176.92(12)
C3 C2 C7 . 121.34(11)
C3 C2 C1 . 116.62(10)
C7 C2 C1 . 122.02(10)
C4 C3 C2 . 120.04(11)
C4 C3 H3 . 120.0
C2 C3 H3 . 120.0
C3 C4 C5 . 119.57(11)
C3 C4 H4 . 120.2
C5 C4 H4 . 120.2
C4 C5 C6 . 120.68(11)
C4 C5 H5 . 119.7
C6 C5 H5 . 119.7
C5 C6 C7 . 121.38(11)
C5 C6 H6 . 119.3
C7 C6 H6 . 119.3
C6 C7 C2 . 116.99(11)
C6 C7 C7 2_655 120.90(12)
C2 C7 C7 2_655 122.09(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.1443(16)
C1 C2 . 1.4427(16)
C2 C3 . 1.3963(16)
C2 C7 . 1.4135(16)
C3 C4 . 1.3800(17)
C3 H3 . 0.9500
C4 C5 . 1.3839(18)
C4 H4 . 0.9500
C5 C6 . 1.3893(17)
C5 H5 . 0.9500
C6 C7 . 1.3957(16)
C6 H6 . 0.9500
C7 C7 2_655 1.488(2)
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_4
_geom_torsion
C7 C2 C3 C4 . -0.18(18)
C1 C2 C3 C4 . -178.65(11)
C2 C3 C4 C5 . -0.26(19)
C3 C4 C5 C6 . 0.34(19)
C4 C5 C6 C7 . 0.02(19)
C5 C6 C7 C2 . -0.44(17)
C5 C6 C7 C7 2_655 -179.21(9)
C3 C2 C7 C6 . 0.51(17)
C1 C2 C7 C6 . 178.91(11)
C3 C2 C7 C7 2_655 179.27(9)
C1 C2 C7 C7 2_655 -2.34(15)
