#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224516.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_2224516
loop_
_publ_author_name
'Kang, Tai-Ran'
'Chen, Lian-Mei'
_publ_section_title
;
 (E)-2-(1,3-Diphenylallylidene)malononitrile
;
_journal_coeditor_code           XU2673
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3164
_journal_paper_doi               10.1107/S1600536809048338
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H12 N2'
_chemical_formula_moiety         'C18 H12 N2'
_chemical_formula_sum            'C18 H12 N2'
_chemical_formula_weight         256.30
_chemical_name_systematic
;
(E)-2-(1,3-Diphenylallylidene)malononitrile
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.457(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1658(6)
_cell_length_b                   14.8852(9)
_cell_length_c                   8.1959(7)
_cell_measurement_reflns_used    5219
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1731
_cell_measurement_theta_min      2.9788
_cell_volume                     1407.85(17)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13329
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0388P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0815
_reflns_number_gt                1735
_reflns_number_total             2880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu2673.cif
_cod_data_source_block           I
_cod_original_cell_volume        1407.85(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224516
_cod_database_fobs_code          2224516
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_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
C C8 1.02337(9) 0.42702(8) 0.80790(16) 0.0520(3) Uani d . 1 . .
H H8 0.9756 0.4731 0.7487 0.062 Uiso calc R 1 . .
C C9 1.14221(9) 0.42886(8) 0.80802(15) 0.0468(3) Uani d . 1 . .
C C16 1.17980(10) 0.50107(7) 0.73655(16) 0.0492(3) Uani d U 1 . .
C C10 1.22053(10) 0.35243(7) 0.87880(15) 0.0466(3) Uani d . 1 . .
C C7 0.97483(10) 0.36634(8) 0.88354(15) 0.0492(3) Uani d . 1 . .
H H7 1.0225 0.3211 0.9464 0.059 Uiso calc R 1 . .
C C4 0.76990(10) 0.41976(8) 0.76497(17) 0.0578(3) Uani d . 1 . .
H H4 0.7914 0.4586 0.6915 0.069 Uiso calc R 1 . .
C C6 0.81719(11) 0.30629(8) 0.98007(17) 0.0564(3) Uani d . 1 . .
H H6 0.8706 0.2677 1.0531 0.068 Uiso calc R 1 . .
C C5 0.85340(9) 0.36488(7) 0.87593(15) 0.0461(3) Uani d . 1 . .
C C1 0.70315(12) 0.30433(9) 0.97724(19) 0.0679(4) Uani d . 1 . .
H H1 0.6804 0.2649 1.0484 0.081 Uiso calc R 1 . .
C C2 0.62347(11) 0.36058(9) 0.86948(19) 0.0679(4) Uani d . 1 . .
H H2 0.5470 0.3601 0.8692 0.082 Uiso calc R 1 . .
C C11 1.32866(10) 0.36506(8) 0.99982(17) 0.0572(3) Uani d . 1 . .
H H11 1.3530 0.4227 1.0384 0.069 Uiso calc R 1 . .
C C3 0.65660(11) 0.41749(9) 0.76217(18) 0.0651(4) Uani d . 1 . .
H H3 0.6021 0.4547 0.6873 0.078 Uiso calc R 1 . .
C C17 1.29300(11) 0.50807(8) 0.71970(17) 0.0578(3) Uani d U 1 . .
C C14 1.25937(13) 0.19431(9) 0.8861(2) 0.0751(4) Uani d . 1 . .
H H14 1.2363 0.1364 0.8474 0.090 Uiso calc R 1 . .
C C15 1.18644(11) 0.26573(8) 0.82240(18) 0.0604(4) Uani d . 1 . .
H H15 1.1142 0.2559 0.7414 0.073 Uiso calc R 1 . .
C C13 1.36577(13) 0.20804(10) 1.0064(2) 0.0778(5) Uani d . 1 . .
H H13 1.4144 0.1595 1.0492 0.093 Uiso calc R 1 . .
C C12 1.40048(12) 0.29275(10) 1.06346(19) 0.0707(4) Uani d . 1 . .
H H12 1.4726 0.3018 1.1453 0.085 Uiso calc R 1 . .
C C18 1.10284(11) 0.57361(9) 0.66242(17) 0.0544(3) Uani d U 1 . .
N N2 1.03886(10) 0.62944(8) 0.60031(16) 0.0742(4) Uani d . 1 . .
N N1 1.38156(11) 0.51654(8) 0.70138(18) 0.0851(4) Uani 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 C8 C9 . . 127.01(11) ?
C7 C8 H8 . . 116.5 ?
C9 C8 H8 . . 116.5 ?
C16 C9 C8 . . 118.92(10) ?
C16 C9 C10 . . 120.68(10) ?
C8 C9 C10 . . 120.36(10) ?
C9 C16 C17 . . 124.07(10) ?
C9 C16 C18 . . 120.73(10) ?
C17 C16 C18 . . 115.09(10) ?
C11 C10 C15 . . 118.66(11) ?
C11 C10 C9 . . 121.57(11) ?
C15 C10 C9 . . 119.77(11) ?
C8 C7 C5 . . 125.53(11) ?
C8 C7 H7 . . 117.2 ?
C5 C7 H7 . . 117.2 ?
C3 C4 C5 . . 121.17(12) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C1 C6 C5 . . 121.10(12) ?
C1 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C5 C4 . . 117.56(10) ?
C6 C5 C7 . . 119.86(11) ?
C4 C5 C7 . . 122.57(11) ?
C2 C1 C6 . . 119.99(12) ?
C2 C1 H1 . . 120.0 ?
C6 C1 H1 . . 120.0 ?
C3 C2 C1 . . 119.97(12) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C12 C11 C10 . . 120.54(12) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C2 C3 C4 . . 120.18(12) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
N1 C17 C16 . . 177.09(14) ?
C13 C14 C15 . . 120.38(13) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C10 . . 120.15(13) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
C12 C13 C14 . . 120.22(13) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C13 C12 C11 . . 120.06(14) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
N2 C18 C16 . . 177.74(14) ?
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
C8 C7 . 1.3344(15) ?
C8 C9 . 1.4457(14) ?
C8 H8 . 0.9300 ?
C9 C16 . 1.3701(15) ?
C9 C10 . 1.4795(15) ?
C16 C17 . 1.4308(16) ?
C16 C18 . 1.4323(18) ?
C10 C11 . 1.3869(16) ?
C10 C15 . 1.3892(16) ?
C7 C5 . 1.4590(15) ?
C7 H7 . 0.9300 ?
C4 C3 . 1.3718(16) ?
C4 C5 . 1.3932(16) ?
C4 H4 . 0.9300 ?
C6 C1 . 1.3805(16) ?
C6 C5 . 1.3861(15) ?
C6 H6 . 0.9300 ?
C1 C2 . 1.3706(19) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.3703(18) ?
C2 H2 . 0.9300 ?
C11 C12 . 1.3804(17) ?
C11 H11 . 0.9300 ?
C3 H3 . 0.9300 ?
C17 N1 . 1.1409(14) ?
C14 C13 . 1.372(2) ?
C14 C15 . 1.3773(18) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C13 C12 . 1.364(2) ?
C13 H13 . 0.9300 ?
C12 H12 . 0.9300 ?
C18 N2 . 1.1423(15) ?
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
C7 C8 C9 C16 . . . . -174.10(11) ?
C7 C8 C9 C10 . . . . 8.02(18) ?
C8 C9 C16 C17 . . . . -176.08(12) ?
C10 C9 C16 C17 . . . . 1.80(17) ?
C8 C9 C16 C18 . . . . -0.14(17) ?
C10 C9 C16 C18 . . . . 177.74(12) ?
C16 C9 C10 C11 . . . . 53.38(16) ?
C8 C9 C10 C11 . . . . -128.77(12) ?
C16 C9 C10 C15 . . . . -125.93(12) ?
C8 C9 C10 C15 . . . . 51.92(15) ?
C9 C8 C7 C5 . . . . -177.82(12) ?
C1 C6 C5 C4 . . . . -1.80(17) ?
C1 C6 C5 C7 . . . . 179.11(12) ?
C3 C4 C5 C6 . . . . 1.64(17) ?
C3 C4 C5 C7 . . . . -179.30(12) ?
C8 C7 C5 C6 . . . . -170.60(11) ?
C8 C7 C5 C4 . . . . 10.37(18) ?
C5 C6 C1 C2 . . . . 0.38(19) ?
C6 C1 C2 C3 . . . . 1.3(2) ?
C15 C10 C11 C12 . . . . -0.38(18) ?
C9 C10 C11 C12 . . . . -179.70(11) ?
C1 C2 C3 C4 . . . . -1.44(19) ?
C5 C4 C3 C2 . . . . -0.05(19) ?
C13 C14 C15 C10 . . . . 0.4(2) ?
C11 C10 C15 C14 . . . . -0.09(18) ?
C9 C10 C15 C14 . . . . 179.25(11) ?
C15 C14 C13 C12 . . . . -0.3(2) ?
C14 C13 C12 C11 . . . . -0.2(2) ?
C10 C11 C12 C13 . . . . 0.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743872
