#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/72/2207274.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_2207274
loop_
_publ_author_name
'Yan-Guang Wang'
'Hui-Ying An'
'Zhi-Feng Lu'
'Lin Wu'
'Jian-Hua Xu'
_publ_section_title
;
 5-Benzylbenzene-1,2,4-tricarbonitrile
;
_journal_coeditor_code           JH6020
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3543
_journal_page_last               o3544
_journal_paper_doi               10.1107/S1600536805031260
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H9 N3'
_chemical_formula_moiety         'C16 H9 N3'
_chemical_formula_sum            'C16 H9 N3'
_chemical_formula_weight         243.26
_chemical_melting_point          421.2
_chemical_name_systematic
;
5-Benzylbenzene-1,2,4-tricarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 113.42(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.289(2)
_cell_length_b                   8.6380(17)
_cell_length_c                   14.193(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1270.0(5)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      288(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2622
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0301P)²+0.8P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                1560
_reflns_number_total             2493
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh6020.cif
_cod_data_source_block           I
_cod_original_cell_volume        1270.0(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207274
_cod_database_fobs_code          2207274
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
N1 0.5853(2) 0.8025(3) 0.02270(18) 0.0766(7) Uani d . 1 N
N2 0.9076(2) 1.1853(3) 0.57250(17) 0.0727(7) Uani d . 1 N
N3 1.0586(2) 1.2572(3) 0.36706(18) 0.0682(6) Uani d . 1 N
C1 0.1781(2) 1.0524(3) 0.1829(3) 0.0692(8) Uani d . 1 C
H1 0.1038 1.1111 0.1683 0.083 Uiso calc R 1 H
C2 0.2198(2) 1.0170(3) 0.1066(2) 0.0662(8) Uani d . 1 C
H2 0.1732 1.0514 0.0399 0.079 Uiso calc R 1 H
C3 0.3306(2) 0.9307(3) 0.12879(18) 0.0514(6) Uani d . 1 C
H3 0.3578 0.9070 0.0766 0.062 Uiso calc R 1 H
C4 0.4014(2) 0.8791(2) 0.22713(17) 0.0387(5) Uani d . 1 C
C5 0.3574(2) 0.9142(3) 0.30277(19) 0.0504(6) Uani d . 1 C
H5 0.4030 0.8792 0.3695 0.060 Uiso calc R 1 H
C6 0.2471(2) 1.0001(3) 0.2806(2) 0.0641(7) Uani d . 1 C
H6 0.2191 1.0231 0.3324 0.077 Uiso calc R 1 H
C7 0.5250(2) 0.7900(2) 0.25312(18) 0.0438(5) Uani d . 1 C
H7A 0.5164 0.7223 0.1963 0.053 Uiso calc R 1 H
H7B 0.5399 0.7258 0.3128 0.053 Uiso calc R 1 H
C8 0.63948(19) 0.8949(2) 0.27495(16) 0.0380(5) Uani d . 1 C
C9 0.6903(2) 0.9284(2) 0.20166(16) 0.0414(5) Uani d . 1 C
C10 0.7962(2) 1.0245(2) 0.22337(17) 0.0446(5) Uani d . 1 C
H10 0.8280 1.0441 0.1733 0.053 Uiso calc R 1 H
C11 0.85451(19) 1.0912(2) 0.31953(17) 0.0397(5) Uani d . 1 C
C12 0.8041(2) 1.0601(2) 0.39365(16) 0.0398(5) Uani d . 1 C
C13 0.6992(2) 0.9629(2) 0.37092(16) 0.0411(5) Uani d . 1 C
H13 0.6679 0.9425 0.4211 0.049 Uiso calc R 1 H
C14 0.6327(2) 0.8583(3) 0.10160(19) 0.0523(6) Uani d . 1 C
C15 0.8625(2) 1.1302(3) 0.49359(18) 0.0486(6) Uani d . 1 C
C16 0.9668(2) 1.1868(3) 0.34467(18) 0.0489(6) Uani d . 1 C
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
_geom_angle_publ_flag
C6 C1 C2 119.3(3) ?
C6 C1 H1 120.4 ?
C2 C1 H1 120.4 ?
C1 C2 C3 120.2(3) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
C4 C3 C2 121.0(2) ?
C4 C3 H3 119.5 ?
C2 C3 H3 119.5 ?
C3 C4 C5 118.2(2) ?
C3 C4 C7 121.5(2) ?
C5 C4 C7 120.4(2) ?
C6 C5 C4 120.8(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
C1 C6 C5 120.6(3) ?
C1 C6 H6 119.7 ?
C5 C6 H6 119.7 ?
C4 C7 C8 112.26(17) yes
C4 C7 H7A 109.2 ?
C8 C7 H7A 109.2 ?
C4 C7 H7B 109.2 ?
C8 C7 H7B 109.2 ?
H7A C7 H7B 107.9 ?
C13 C8 C9 117.26(19) ?
C13 C8 C7 119.9(2) ?
C9 C8 C7 122.80(19) ?
C10 C9 C8 122.0(2) ?
C10 C9 C14 118.9(2) ?
C8 C9 C14 119.2(2) ?
C11 C10 C9 120.0(2) ?
C11 C10 H10 120.0 ?
C9 C10 H10 120.0 ?
C10 C11 C12 118.8(2) ?
C10 C11 C16 120.8(2) ?
C12 C11 C16 120.3(2) ?
C13 C12 C11 120.4(2) ?
C13 C12 C15 120.0(2) ?
C11 C12 C15 119.6(2) ?
C12 C13 C8 121.6(2) ?
C12 C13 H13 119.2 ?
C8 C13 H13 119.2 ?
N1 C14 C9 178.8(3) ?
N2 C15 C12 179.4(3) ?
N3 C16 C11 177.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C14 1.138(3) ?
N2 C15 1.135(3) ?
N3 C16 1.133(3) ?
C1 C6 1.369(4) ?
C1 C2 1.376(4) ?
C1 H1 0.9300 ?
C2 C3 1.381(3) ?
C2 H2 0.9300 ?
C3 C4 1.378(3) ?
C3 H3 0.9300 ?
C4 C5 1.384(3) ?
C4 C7 1.505(3) yes
C5 C6 1.374(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.506(3) yes
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C13 1.387(3) ?
C8 C9 1.403(3) ?
C9 C10 1.385(3) ?
C9 C14 1.440(3) yes
C10 C11 1.384(3) ?
C10 H10 0.9300 ?
C11 C12 1.407(3) ?
C11 C16 1.434(3) yes
C12 C13 1.381(3) ?
C12 C15 1.439(3) yes
C13 H13 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
_geom_hbond_publ_flag
C1 H1 N2 4_485 0.93 2.73 3.621(3) 161 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
C6 C1 C2 C3 -0.4(4)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 0.9(3)
C2 C3 C4 C7 -177.7(2)
C3 C4 C5 C6 -1.0(3)
C7 C4 C5 C6 177.7(2)
C2 C1 C6 C5 0.4(4)
C4 C5 C6 C1 0.3(4)
C3 C4 C7 C8 84.3(3)
C5 C4 C7 C8 -94.3(2)
C4 C7 C8 C13 81.2(2)
C4 C7 C8 C9 -98.9(2)
C13 C8 C9 C10 0.4(3)
C7 C8 C9 C10 -179.6(2)
C13 C8 C9 C14 178.92(19)
C7 C8 C9 C14 -1.0(3)
C8 C9 C10 C11 -0.4(3)
C14 C9 C10 C11 -178.9(2)
C9 C10 C11 C12 -0.2(3)
C9 C10 C11 C16 177.9(2)
C10 C11 C12 C13 0.8(3)
C16 C11 C12 C13 -177.3(2)
C10 C11 C12 C15 -179.2(2)
C16 C11 C12 C15 2.7(3)
C11 C12 C13 C8 -0.8(3)
C15 C12 C13 C8 179.2(2)
C9 C8 C13 C12 0.2(3)
C7 C8 C13 C12 -179.79(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127063
