#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/42/2234233.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_2234233
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Faidallah, Hassan M.'
'Sobahi, Tariq R.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (4Z)-4-Benzylidene-2-phenyl-1,3-oxazol-5(4H)-one
;
_journal_coeditor_code           HB6681
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1154
_journal_paper_doi               10.1107/S1600536812011579
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H13 N O2'
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_name_systematic
;
(4Z)-4-Benzylidene-2-phenyl-1,3-oxazol-5(4H)-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0827(6)
_cell_length_b                   7.7848(3)
_cell_length_c                   27.6527(16)
_cell_measurement_reflns_used    2443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5021
_cell_measurement_theta_min      2.6111
_cell_volume                     2601.1(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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 (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7121
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0438
_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)+(0.0430P)²+0.6059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                2206
_reflns_number_total             2990
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6681.cif
_cod_data_source_block           I
_cod_database_code               2234233
_cod_database_fobs_code          2234233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
O O1 0.70006(8) 0.51990(13) 0.55832(4) 0.0199(3) Uani d . 1 1
O O2 0.76383(9) 0.68781(14) 0.61933(4) 0.0270(3) Uani d . 1 1
N N1 0.53733(10) 0.42459(15) 0.58986(4) 0.0174(3) Uani d . 1 1
C C1 0.60411(12) 0.42309(18) 0.55339(6) 0.0176(3) Uani d . 1 1
C C2 0.69316(13) 0.59344(19) 0.60408(6) 0.0197(3) Uani d . 1 1
C C3 0.58820(12) 0.52949(18) 0.62455(6) 0.0176(3) Uani d . 1 1
C C4 0.55689(12) 0.56871(18) 0.67001(6) 0.0186(3) Uani d . 1 1
H H4 0.6050 0.6445 0.6868 0.022 Uiso calc R 1 1
C C5 0.46027(12) 0.51218(18) 0.69718(6) 0.0176(3) Uani d . 1 1
C C6 0.44944(13) 0.5668(2) 0.74539(6) 0.0220(4) Uani d . 1 1
H H6 0.5037 0.6409 0.7590 0.026 Uiso calc R 1 1
C C7 0.36046(14) 0.51376(19) 0.77344(6) 0.0238(4) Uani d . 1 1
H H7 0.3538 0.5520 0.8059 0.029 Uiso calc R 1 1
C C8 0.28135(14) 0.40496(19) 0.75395(6) 0.0233(4) Uani d . 1 1
H H8 0.2205 0.3683 0.7731 0.028 Uiso calc R 1 1
C C9 0.29095(13) 0.3493(2) 0.70625(6) 0.0226(4) Uani d . 1 1
H H9 0.2368 0.2741 0.6931 0.027 Uiso calc R 1 1
C C10 0.37888(12) 0.40289(19) 0.67789(6) 0.0200(3) Uani d . 1 1
H H10 0.3842 0.3656 0.6453 0.024 Uiso calc R 1 1
C C11 0.59187(12) 0.32991(18) 0.50822(5) 0.0169(3) Uani d . 1 1
C C12 0.67737(13) 0.3232(2) 0.47430(6) 0.0221(4) Uani d . 1 1
H H12 0.7441 0.3847 0.4799 0.027 Uiso calc R 1 1
C C13 0.66513(13) 0.2269(2) 0.43248(6) 0.0249(4) Uani d . 1 1
H H13 0.7241 0.2222 0.4098 0.030 Uiso calc R 1 1
C C14 0.56739(13) 0.13662(19) 0.42313(6) 0.0216(3) Uani d . 1 1
C C15 0.48133(13) 0.14847(19) 0.45658(6) 0.0211(3) Uani d . 1 1
H H15 0.4136 0.0906 0.4504 0.025 Uiso calc R 1 1
C C16 0.49287(12) 0.24313(18) 0.49867(6) 0.0195(3) Uani d . 1 1
H H16 0.4335 0.2491 0.5211 0.023 Uiso calc R 1 1
C C17 0.55537(15) 0.0289(2) 0.37818(6) 0.0292(4) Uani d . 1 1
H H17A 0.5060 -0.0682 0.3848 0.044 Uiso calc R 1 1
H H17B 0.6282 -0.0144 0.3684 0.044 Uiso calc R 1 1
H H17C 0.5241 0.0990 0.3521 0.044 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 0.0033 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'
O O 0.0106 0.0060 '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 O1 C1 105.22(11)
C1 N1 C3 105.41(12)
N1 C1 O1 116.08(13)
N1 C1 C11 127.78(14)
O1 C1 C11 116.13(13)
O2 C2 O1 121.84(14)
O2 C2 C3 133.00(15)
O1 C2 C3 105.16(12)
C4 C3 N1 130.33(14)
C4 C3 C2 121.51(14)
N1 C3 C2 108.12(13)
C3 C4 C5 129.62(14)
C3 C4 H4 115.2
C5 C4 H4 115.2
C10 C5 C6 118.55(14)
C10 C5 C4 123.23(14)
C6 C5 C4 118.21(14)
C7 C6 C5 120.80(15)
C7 C6 H6 119.6
C5 C6 H6 119.6
C8 C7 C6 119.90(15)
C8 C7 H7 120.1
C6 C7 H7 120.1
C7 C8 C9 120.05(15)
C7 C8 H8 120.0
C9 C8 H8 120.0
C10 C9 C8 120.41(15)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C5 120.29(15)
C9 C10 H10 119.9
C5 C10 H10 119.9
C12 C11 C16 119.18(14)
C12 C11 C1 121.42(14)
C16 C11 C1 119.39(13)
C13 C12 C11 120.13(15)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 121.08(15)
C12 C13 H13 119.5
C14 C13 H13 119.5
C15 C14 C13 118.27(15)
C15 C14 C17 120.80(15)
C13 C14 C17 120.93(15)
C16 C15 C14 121.17(15)
C16 C15 H15 119.4
C14 C15 H15 119.4
C15 C16 C11 120.13(14)
C15 C16 H16 119.9
C11 C16 H16 119.9
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3913(19)
O1 C1 1.3895(18)
O2 C2 1.2028(18)
N1 C1 1.2915(19)
N1 C3 1.4017(19)
C1 C11 1.452(2)
C2 C3 1.475(2)
C3 C4 1.348(2)
C4 C5 1.456(2)
C4 H4 0.9500
C5 C10 1.406(2)
C5 C6 1.405(2)
C6 C7 1.388(2)
C6 H6 0.9500
C7 C8 1.386(2)
C7 H7 0.9500
C8 C9 1.393(2)
C8 H8 0.9500
C9 C10 1.385(2)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.396(2)
C11 C16 1.399(2)
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.399(2)
C13 H13 0.9500
C14 C15 1.395(2)
C14 C17 1.507(2)
C15 C16 1.385(2)
C15 H15 0.9500
C16 H16 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 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
C7 H7 O2 6_557 0.95 2.56 3.463(2) 158
C6 H6 Cg1 4_656 0.95 2.93 3.8311(17) 158
C9 H9 Cg1 7_545 0.95 2.92 3.6532(17) 135
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
C3 N1 C1 O1 -0.47(16)
C3 N1 C1 C11 178.31(14)
C2 O1 C1 N1 -0.24(16)
C2 O1 C1 C11 -179.16(12)
C1 O1 C2 O2 -179.03(14)
C1 O1 C2 C3 0.80(14)
C1 N1 C3 C4 -176.66(15)
C1 N1 C3 C2 0.95(15)
O2 C2 C3 C4 -3.4(3)
O1 C2 C3 C4 176.76(13)
O2 C2 C3 N1 178.70(16)
O1 C2 C3 N1 -1.10(15)
N1 C3 C4 C5 0.6(3)
C2 C3 C4 C5 -176.76(14)
C3 C4 C5 C10 -1.3(2)
C3 C4 C5 C6 177.19(15)
C10 C5 C6 C7 0.1(2)
C4 C5 C6 C7 -178.48(14)
C5 C6 C7 C8 0.3(2)
C6 C7 C8 C9 -0.2(2)
C7 C8 C9 C10 -0.4(2)
C8 C9 C10 C5 0.9(2)
C6 C5 C10 C9 -0.7(2)
C4 C5 C10 C9 177.79(14)
N1 C1 C11 C12 -171.85(15)
O1 C1 C11 C12 6.9(2)
N1 C1 C11 C16 7.3(2)
O1 C1 C11 C16 -173.88(12)
C16 C11 C12 C13 -2.1(2)
C1 C11 C12 C13 177.12(14)
C11 C12 C13 C14 0.7(2)
C12 C13 C14 C15 1.2(2)
C12 C13 C14 C17 -178.58(14)
C13 C14 C15 C16 -1.7(2)
C17 C14 C15 C16 178.08(14)
C14 C15 C16 C11 0.3(2)
C12 C11 C16 C15 1.6(2)
C1 C11 C16 C15 -177.63(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1267693
