#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230579.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_2230579
loop_
_publ_author_name
'Balakrishnan, B.'
'Praveen, C.'
'Seshadri, P. R.'
'Perumal, P. T.'
_publ_section_title
;
 5-(3-Methylphenyl)-3-phenyl-1,2-oxazole
;
_journal_coeditor_code           BT5513
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1575
_journal_paper_doi               10.1107/S1600536811020198
_journal_volume                  67
_journal_year                    2011
_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
;
5-(3-Methylphenyl)-3-phenyl-1,2-oxazole
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.8052(2)
_cell_length_b                   7.7010(3)
_cell_length_c                   27.4363(8)
_cell_measurement_reflns_used    14583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      1.48
_cell_volume                     1226.56(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       ω
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14583
_diffrn_reflns_theta_full        27.07
_diffrn_reflns_theta_max         27.07
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0547P)²+0.1446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                1302
_reflns_number_total             1599
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5513.cif
_cod_data_source_block           I
_cod_database_code               2230579
_cod_database_fobs_code          2230579
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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.3214(3) 0.4492(3) 0.09265(7) 0.0550(5) Uani d . 1 1 . .
O O 0.3690(3) 0.3988(3) 0.14108(6) 0.0662(5) Uani d . 1 1 . .
C C9 0.5947(4) 0.3630(3) 0.14404(8) 0.0492(6) Uani d . 1 1 . .
C C10 0.6819(4) 0.3105(3) 0.19162(8) 0.0471(5) Uani d . 1 1 . .
C C14 0.6336(4) 0.2897(3) 0.27920(8) 0.0498(5) Uani d . 1 1 . .
C C7 0.5182(4) 0.4406(3) 0.06915(8) 0.0505(5) Uani d . 1 1 . .
C C15 0.5545(4) 0.3395(3) 0.23393(8) 0.0491(5) Uani d . 1 1 . .
H H15 0.4121 0.3941 0.2315 0.059 Uiso calc R 1 1 . .
C C13 0.8460(4) 0.2078(3) 0.28208(9) 0.0553(6) Uani d . 1 1 . .
H H13 0.9016 0.1721 0.3123 0.066 Uiso calc R 1 1 . .
C C8 0.6941(4) 0.3875(3) 0.09969(8) 0.0526(6) Uani d . 1 1 . .
H H8 0.8483 0.3718 0.0916 0.063 Uiso calc R 1 1 . .
C C1 0.7032(5) 0.4368(3) -0.01203(9) 0.0650(7) Uani d . 1 1 . .
H H1 0.8257 0.3757 0.0015 0.078 Uiso calc R 1 1 . .
C C12 0.9760(5) 0.1786(3) 0.24080(10) 0.0603(6) Uani d . 1 1 . .
H H12 1.1181 0.1237 0.2434 0.072 Uiso calc R 1 1 . .
C C11 0.8968(4) 0.2303(3) 0.19575(10) 0.0556(6) Uani d . 1 1 . .
H H11 0.9863 0.2119 0.1681 0.067 Uiso calc R 1 1 . .
C C6 0.5200(4) 0.4874(3) 0.01707(8) 0.0506(5) Uani d . 1 1 . .
C C5 0.3401(5) 0.5778(3) -0.00369(9) 0.0627(7) Uani d . 1 1 . .
H H5 0.2162 0.6123 0.0155 0.075 Uiso calc R 1 1 . .
C C16 0.4918(5) 0.3241(4) 0.32435(9) 0.0708(8) Uani d . 1 1 . .
H H16A 0.4844 0.4469 0.3302 0.106 Uiso calc R 1 1 . .
H H16B 0.5620 0.2679 0.3518 0.106 Uiso calc R 1 1 . .
H H16C 0.3390 0.2795 0.3198 0.106 Uiso calc R 1 1 . .
C C4 0.3426(5) 0.6172(4) -0.05246(10) 0.0718(8) Uani d . 1 1 . .
H H4 0.2208 0.6784 -0.0662 0.086 Uiso calc R 1 1 . .
C C3 0.5239(5) 0.5667(4) -0.08088(10) 0.0739(8) Uani d . 1 1 . .
H H3 0.5248 0.5934 -0.1139 0.089 Uiso calc R 1 1 . .
C C2 0.7041(6) 0.4771(4) -0.06096(10) 0.0728(8) Uani d . 1 1 . .
H H2 0.8272 0.4432 -0.0804 0.087 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N O . . 106.11(18) ?
C9 O N . . 107.76(18) ?
O C9 C8 . . 109.4(2) ?
O C9 C10 . . 116.8(2) ?
C8 C9 C10 . . 133.8(2) ?
C15 C10 C11 . . 118.5(2) ?
C15 C10 C9 . . 121.2(2) ?
C11 C10 C9 . . 120.4(2) ?
C15 C14 C13 . . 118.3(2) ?
C15 C14 C16 . . 120.6(2) ?
C13 C14 C16 . . 121.2(2) ?
N C7 C8 . . 111.1(2) ?
N C7 C6 . . 118.0(2) ?
C8 C7 C6 . . 130.9(2) ?
C14 C15 C10 . . 121.9(2) ?
C14 C15 H15 . . 119.0 ?
C10 C15 H15 . . 119.0 ?
C12 C13 C14 . . 120.9(2) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C9 C8 C7 . . 105.7(2) ?
C9 C8 H8 . . 127.2 ?
C7 C8 H8 . . 127.2 ?
C2 C1 C6 . . 120.1(3) ?
C2 C1 H1 . . 120.0 ?
C6 C1 H1 . . 120.0 ?
C11 C12 C13 . . 120.5(2) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C12 C11 C10 . . 119.9(2) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C5 C6 C1 . . 119.0(2) ?
C5 C6 C7 . . 121.3(2) ?
C1 C6 C7 . . 119.7(2) ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C3 C2 . . 120.3(3) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C2 C1 . . 120.0(3) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
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
N C7 . 1.314(3) ?
N O . 1.412(2) ?
O C9 . 1.341(3) ?
C9 C8 . 1.360(3) ?
C9 C10 . 1.457(3) ?
C10 C15 . 1.394(3) ?
C10 C11 . 1.397(3) ?
C14 C15 . 1.379(3) ?
C14 C13 . 1.387(3) ?
C14 C16 . 1.511(3) ?
C7 C8 . 1.383(3) ?
C7 C6 . 1.474(3) ?
C15 H15 . 0.9300 ?
C13 C12 . 1.379(4) ?
C13 H13 . 0.9300 ?
C8 H8 . 0.9300 ?
C1 C2 . 1.378(4) ?
C1 C6 . 1.386(3) ?
C1 H1 . 0.9300 ?
C12 C11 . 1.378(3) ?
C12 H12 . 0.9300 ?
C11 H11 . 0.9300 ?
C6 C5 . 1.378(3) ?
C5 C4 . 1.372(4) ?
C5 H5 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C4 C3 . 1.366(4) ?
C4 H4 . 0.9300 ?
C3 C2 . 1.367(4) ?
C3 H3 . 0.9300 ?
C2 H2 . 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
C15 H15 O . 0.9300 2.4900 2.803(3) 100.00 ?
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 N O C9 . . . . 0.3(3) ?
N O C9 C8 . . . . -0.2(3) ?
N O C9 C10 . . . . 179.04(18) ?
O C9 C10 C15 . . . . -16.3(3) ?
C8 C9 C10 C15 . . . . 162.8(3) ?
O C9 C10 C11 . . . . 164.0(2) ?
C8 C9 C10 C11 . . . . -16.9(4) ?
O N C7 C8 . . . . -0.2(3) ?
O N C7 C6 . . . . -179.81(18) ?
C13 C14 C15 C10 . . . . -0.3(3) ?
C16 C14 C15 C10 . . . . 179.6(2) ?
C11 C10 C15 C14 . . . . -0.8(3) ?
C9 C10 C15 C14 . . . . 179.6(2) ?
C15 C14 C13 C12 . . . . 0.7(3) ?
C16 C14 C13 C12 . . . . -179.2(2) ?
O C9 C8 C7 . . . . 0.1(3) ?
C10 C9 C8 C7 . . . . -179.0(2) ?
N C7 C8 C9 . . . . 0.1(3) ?
C6 C7 C8 C9 . . . . 179.6(2) ?
C14 C13 C12 C11 . . . . -0.1(4) ?
C13 C12 C11 C10 . . . . -1.0(4) ?
C15 C10 C11 C12 . . . . 1.4(3) ?
C9 C10 C11 C12 . . . . -178.9(2) ?
C2 C1 C6 C5 . . . . 0.1(4) ?
C2 C1 C6 C7 . . . . 178.7(3) ?
N C7 C6 C5 . . . . 16.0(3) ?
C8 C7 C6 C5 . . . . -163.5(3) ?
N C7 C6 C1 . . . . -162.6(2) ?
C8 C7 C6 C1 . . . . 17.9(4) ?
C1 C6 C5 C4 . . . . -0.1(4) ?
C7 C6 C5 C4 . . . . -178.7(2) ?
C6 C5 C4 C3 . . . . 0.1(4) ?
C5 C4 C3 C2 . . . . -0.2(4) ?
C4 C3 C2 C1 . . . . 0.2(4) ?
C6 C1 C2 C3 . . . . -0.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656750
