#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225927.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_2225927
loop_
_publ_author_name
'Baldaniya, Bharat B.'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene]methyl}phenyl
 acetate
;
_journal_coeditor_code           LH5032
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1175
_journal_paper_doi               10.1107/S1600536810014911
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H13 N O4'
_chemical_formula_moiety         'C18 H13 N O4'
_chemical_formula_sum            'C18 H13 N O4'
_chemical_formula_weight         307.29
_chemical_name_systematic
;
4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene]methyl}phenyl
acetate
;
_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
_cell_angle_beta                 98.025(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3507(15)
_cell_length_b                   3.9443(9)
_cell_length_c                   28.527(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      20.0
_cell_volume                     1487.5(5)
_computing_cell_refinement       'XCAD4 (Harms & Wocadlo, 1996)'
_computing_data_collection       'XCAD4 (Harms & Wocadlo, 1996)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       '2θ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            2593
_diffrn_reflns_theta_full        64.9
_diffrn_reflns_theta_max         64.9
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  3600
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_coef       0.0081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0834P)²+0.1813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.123
_refine_ls_wR_factor_ref         0.140
_reflns_number_gt                1795
_reflns_number_total             2491
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5032.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225927
_cod_database_fobs_code          2225927
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
O O1 0.98210(13) -0.0744(6) 0.36427(7) 0.0805(7) Uani d . 1 . .
O O2 0.96858(10) -0.3277(4) 0.43327(5) 0.0501(4) Uani d . 1 . .
O O3 0.36614(12) 0.4187(5) 0.44993(6) 0.0606(5) Uani d . 1 . .
O O4 0.32332(10) 0.1834(4) 0.37774(5) 0.0466(4) Uani d . 1 . .
N N1 0.47109(13) -0.0534(5) 0.36494(6) 0.0430(5) Uani d . 1 . .
C C1 1.12156(18) -0.3904(7) 0.40327(10) 0.0628(7) Uani d . 1 . .
H H1A 1.1314 -0.5250 0.3763 0.094 Uiso calc R 1 . .
H H1B 1.1304 -0.5297 0.4311 0.094 Uiso calc R 1 . .
H H1C 1.1700 -0.2091 0.4069 0.094 Uiso calc R 1 . .
C C2 1.01799(17) -0.2475(7) 0.39635(9) 0.0496(6) Uani d . 1 . .
C C3 0.86835(15) -0.2184(6) 0.43289(8) 0.0425(5) Uani d . 1 . .
C C4 0.79303(16) -0.3064(6) 0.39696(8) 0.0447(6) Uani d . 1 . .
H H4 0.8082 -0.4318 0.3713 0.054 Uiso calc R 1 . .
C C5 0.69517(15) -0.2074(6) 0.39935(7) 0.0414(5) Uani d . 1 . .
H H5 0.6442 -0.2660 0.3751 0.050 Uiso calc R 1 . .
C C6 0.67139(15) -0.0187(6) 0.43805(7) 0.0388(5) Uani d . 1 . .
C C7 0.74930(16) 0.0581(6) 0.47402(8) 0.0453(6) Uani d . 1 . .
H H7 0.7348 0.1787 0.5003 0.054 Uiso calc R 1 . .
C C8 0.84763(16) -0.0399(6) 0.47180(7) 0.0479(6) Uani d . 1 . .
H H8 0.8990 0.0138 0.4962 0.057 Uiso calc R 1 . .
C C9 0.57088(15) 0.1106(6) 0.44158(7) 0.0406(5) Uani d . 1 . .
H H9 0.5640 0.2187 0.4699 0.049 Uiso calc R 1 . .
C C10 0.48645(15) 0.0971(6) 0.40999(7) 0.0396(5) Uani d . 1 . .
C C11 0.39108(16) 0.2560(6) 0.41824(8) 0.0435(5) Uani d . 1 . .
C C12 0.37851(15) 0.0018(6) 0.34861(7) 0.0410(5) Uani d . 1 . .
C C13 0.32449(17) -0.1052(6) 0.30296(8) 0.0449(6) Uani d . 1 . .
C C14 0.22131(19) -0.0575(7) 0.29152(9) 0.0566(7) Uani d . 1 . .
H H14 0.1849 0.0484 0.3129 0.068 Uiso calc R 1 . .
C C15 0.1725(2) -0.1672(8) 0.24835(10) 0.0686(8) Uani d . 1 . .
H H15 0.1030 -0.1381 0.2409 0.082 Uiso calc R 1 . .
C C16 0.2258(2) -0.3186(7) 0.21650(9) 0.0692(8) Uani d . 1 . .
H H16 0.1924 -0.3929 0.1875 0.083 Uiso calc R 1 . .
C C17 0.3283(2) -0.3612(7) 0.22719(9) 0.0673(8) Uani d . 1 . .
H H17 0.3644 -0.4603 0.2051 0.081 Uiso calc R 1 . .
C C18 0.3783(2) -0.2584(7) 0.27036(8) 0.0567(7) Uani d . 1 . .
H H18 0.4477 -0.2913 0.2777 0.068 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O2 C3 . . 119.26(17) ?
C12 O4 C11 . . 105.40(16) ?
C12 N1 C10 . . 105.77(17) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 O2 . . 123.0(2) ?
O1 C2 C1 . . 126.2(2) ?
O2 C2 C1 . . 110.7(2) ?
C8 C3 C4 . . 121.5(2) ?
C8 C3 O2 . . 116.73(19) ?
C4 C3 O2 . . 121.6(2) ?
C5 C4 C3 . . 119.5(2) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C7 C6 C5 . . 117.93(19) ?
C7 C6 C9 . . 118.43(19) ?
C5 C6 C9 . . 123.59(19) ?
C8 C7 C6 . . 121.6(2) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C3 C8 C7 . . 118.7(2) ?
C3 C8 H8 . . 120.6 ?
C7 C8 H8 . . 120.6 ?
C10 C9 C6 . . 129.6(2) ?
C10 C9 H9 . . 115.2 ?
C6 C9 H9 . . 115.2 ?
C9 C10 N1 . . 129.26(19) ?
C9 C10 C11 . . 122.8(2) ?
N1 C10 C11 . . 107.96(18) ?
O3 C11 O4 . . 121.40(19) ?
O3 C11 C10 . . 133.7(2) ?
O4 C11 C10 . . 104.85(18) ?
N1 C12 O4 . . 115.99(18) ?
N1 C12 C13 . . 127.46(19) ?
O4 C12 C13 . . 116.54(18) ?
C14 C13 C18 . . 119.5(2) ?
C14 C13 C12 . . 121.5(2) ?
C18 C13 C12 . . 119.0(2) ?
C15 C14 C13 . . 119.9(3) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C16 C15 C14 . . 120.3(3) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 C17 . . 120.1(2) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.5(3) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C13 . . 119.7(3) ?
C17 C18 H18 . . 120.2 ?
C13 C18 H18 . . 120.2 ?
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
O1 C2 . 1.188(3) ?
O2 C2 . 1.356(3) ?
O2 C3 . 1.404(2) ?
O3 C11 . 1.193(3) ?
O4 C12 . 1.385(2) ?
O4 C11 . 1.394(3) ?
N1 C12 . 1.277(3) ?
N1 C10 . 1.404(3) ?
C1 C2 . 1.481(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C8 . 1.375(3) ?
C3 C4 . 1.376(3) ?
C4 C5 . 1.374(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.404(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(3) ?
C6 C9 . 1.452(3) ?
C7 C8 . 1.378(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.343(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.468(3) ?
C12 C13 . 1.460(3) ?
C13 C14 . 1.384(3) ?
C13 C18 . 1.390(3) ?
C14 C15 . 1.380(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.367(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.371(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.377(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 714931
