#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/40/2234053.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_2234053
loop_
_publ_author_name
'Abdel-Aziz, Alaa A.-M.'
'El-Azab, Adel S.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-Oxo-2,4-diphenylbutanenitrile
;
_journal_coeditor_code           XU5469
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o736
_journal_paper_doi               10.1107/S1600536812006137
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H13 N O'
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_chemical_name_systematic
;
4-Oxo-2,4-diphenylbutanenitrile
;
_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                 99.217(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2158(3)
_cell_length_b                   8.9244(2)
_cell_length_c                   9.7553(2)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0181
_cell_measurement_theta_min      3.1468
_cell_volume                     1221.65(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4625
_diffrn_reflns_theta_full        76.21
_diffrn_reflns_theta_max         76.21
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0364
_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)+(0.0480P)²+0.3439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2187
_reflns_number_total             2496
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5469.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234053
_cod_database_fobs_code          2234053
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_symmetry_multiplicity
O O1 0.36576(6) 0.21438(10) 0.43914(9) 0.0285(2) Uani d . 1 1
N N1 0.17432(7) 0.10500(12) 0.59790(12) 0.0279(2) Uani d . 1 1
C C1 0.49902(8) 0.30995(13) 0.59134(12) 0.0208(2) Uani d . 1 1
C C2 0.53560(8) 0.42071(14) 0.68608(12) 0.0247(3) Uani d . 1 1
H H2 0.4947 0.4960 0.7124 0.030 Uiso calc R 1 1
C C3 0.63208(9) 0.42086(16) 0.74205(13) 0.0298(3) Uani d . 1 1
H H3 0.6570 0.4966 0.8062 0.036 Uiso calc R 1 1
C C4 0.69199(8) 0.31074(16) 0.70442(13) 0.0299(3) Uani d . 1 1
H H4 0.7575 0.3102 0.7441 0.036 Uiso calc R 1 1
C C5 0.65640(9) 0.20143(15) 0.60905(14) 0.0297(3) Uani d . 1 1
H H5 0.6976 0.1268 0.5826 0.036 Uiso calc R 1 1
C C6 0.56030(9) 0.20125(14) 0.55228(13) 0.0252(3) Uani d . 1 1
H H6 0.5361 0.1267 0.4865 0.030 Uiso calc R 1 1
C C7 0.39562(8) 0.30324(13) 0.53106(12) 0.0205(2) Uani d . 1 1
C C8 0.32829(7) 0.40714(13) 0.59087(12) 0.0201(2) Uani d . 1 1
H H8 0.3436 0.5120 0.5698 0.024 Uiso calc R 1 1
H H8B 0.3386 0.3957 0.6931 0.024 Uiso calc R 1 1
C C9 0.22257(7) 0.37701(13) 0.53382(12) 0.0198(2) Uani d . 1 1
H H9 0.2119 0.3901 0.4307 0.024 Uiso calc R 1 1
C C10 0.19687(8) 0.22196(13) 0.56679(12) 0.0211(2) Uani d . 1 1
C C11 0.15783(7) 0.48444(12) 0.59617(12) 0.0187(2) Uani d . 1 1
C C12 0.11047(8) 0.59901(13) 0.51696(12) 0.0218(2) Uani d . 1 1
H H12 0.1195 0.6126 0.4233 0.026 Uiso calc R 1 1
C C13 0.04974(8) 0.69400(13) 0.57491(13) 0.0232(3) Uani d . 1 1
H H13 0.0177 0.7726 0.5207 0.028 Uiso calc R 1 1
C C14 0.03583(8) 0.67459(13) 0.71113(13) 0.0224(2) Uani d . 1 1
H H14 -0.0067 0.7384 0.7496 0.027 Uiso calc R 1 1
C C15 0.08427(8) 0.56136(13) 0.79140(12) 0.0234(2) Uani d . 1 1
H H15 0.0755 0.5483 0.8852 0.028 Uiso calc R 1 1
C C16 0.14544(8) 0.46762(12) 0.73418(12) 0.0211(2) Uani d . 1 1
H H16 0.1792 0.3913 0.7895 0.025 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 C6 119.34(11)
C2 C1 C7 121.85(10)
C6 C1 C7 118.81(11)
C3 C2 C1 119.96(11)
C3 C2 H2 120.0
C1 C2 H2 120.0
C4 C3 C2 120.21(12)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.15(11)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 119.88(12)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 120.44(12)
C5 C6 H6 119.8
C1 C6 H6 119.8
O1 C7 C1 121.29(10)
O1 C7 C8 120.89(10)
C1 C7 C8 117.79(10)
C7 C8 C9 113.21(9)
C7 C8 H8 108.9
C9 C8 H8 108.9
C7 C8 H8B 108.9
C9 C8 H8B 108.9
H8 C8 H8B 107.7
C10 C9 C11 108.43(9)
C10 C9 C8 110.20(9)
C11 C9 C8 111.29(9)
C10 C9 H9 109.0
C11 C9 H9 109.0
C8 C9 H9 109.0
N1 C10 C9 176.20(12)
C12 C11 C16 119.46(10)
C12 C11 C9 120.78(10)
C16 C11 C9 119.76(10)
C11 C12 C13 119.93(11)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 120.41(11)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.79(11)
C13 C14 H14 120.1
C15 C14 H14 120.1
C16 C15 C14 119.82(11)
C16 C15 H15 120.1
C14 C15 H15 120.1
C15 C16 C11 120.55(10)
C15 C16 H16 119.7
C11 C16 H16 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2212(14)
N1 C10 1.1470(16)
C1 C2 1.3956(17)
C1 C6 1.3970(16)
C1 C7 1.4944(15)
C2 C3 1.3926(17)
C2 H2 0.9500
C3 C4 1.3879(19)
C3 H3 0.9500
C4 C5 1.386(2)
C4 H4 0.9500
C5 C6 1.3894(17)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.5151(15)
C8 C9 1.5403(14)
C8 H8 0.9900
C8 H8B 0.9900
C9 C10 1.4796(16)
C9 C11 1.5217(14)
C9 H9 1.0000
C11 C12 1.3889(16)
C11 C16 1.3936(16)
C12 C13 1.3929(16)
C12 H12 0.9500
C13 C14 1.3853(17)
C13 H13 0.9500
C14 C15 1.3914(16)
C14 H14 0.9500
C15 C16 1.3868(16)
C15 H15 0.9500
C16 H16 0.9500
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
C3 H3 N1 2_656 0.95 2.62 3.3669(17) 136
C8 H8b O1 4_566 0.99 2.56 3.5246(14) 163
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 -0.85(18)
C7 C1 C2 C3 178.58(11)
C1 C2 C3 C4 -0.31(19)
C2 C3 C4 C5 1.11(19)
C3 C4 C5 C6 -0.74(19)
C4 C5 C6 C1 -0.44(19)
C2 C1 C6 C5 1.23(18)
C7 C1 C6 C5 -178.23(11)
C2 C1 C7 O1 173.35(11)
C6 C1 C7 O1 -7.21(17)
C2 C1 C7 C8 -8.53(16)
C6 C1 C7 C8 170.91(10)
O1 C7 C8 C9 5.29(15)
C1 C7 C8 C9 -172.83(9)
C7 C8 C9 C10 59.99(12)
C7 C8 C9 C11 -179.69(9)
C10 C9 C11 C12 -130.84(11)
C8 C9 C11 C12 107.79(12)
C10 C9 C11 C16 48.89(13)
C8 C9 C11 C16 -72.47(13)
C16 C11 C12 C13 -1.27(16)
C9 C11 C12 C13 178.47(10)
C11 C12 C13 C14 -0.31(17)
C12 C13 C14 C15 1.28(17)
C13 C14 C15 C16 -0.67(17)
C14 C15 C16 C11 -0.91(17)
C12 C11 C16 C15 1.88(17)
C9 C11 C16 C15 -177.85(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 86061
