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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222962.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_2222962
loop_
_publ_author_name
'Loghmani-Khouzani, Hossein'
'Hajiheidari, Dariush'
'Robinson, Ward T.'
'Abdul Rahman, Noorsaadah'
'Kia, Reza'
_publ_section_title
;
 2-(1,3-Benzoxazol-2-ylsulfanyl)-1-phenylethanone
;
_journal_coeditor_code           AT2859
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2287
_journal_paper_doi               10.1107/S1600536809033960
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H11 N O2 S'
_chemical_formula_moiety         'C15 H11 N O2 S'
_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_weight         269.31
_chemical_melting_point          398
_chemical_name_systematic
;
2-(1,3-Benzoxazol-2-ylsulfanyl)-1-phenylethanone
;
_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                   4.8580(2)
_cell_length_b                   14.0780(5)
_cell_length_c                   18.6840(7)
_cell_measurement_reflns_used    4173
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.62
_cell_volume                     1277.82(8)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13902
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.8855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.188
_refine_ls_abs_structure_details 'Flack (1983), 1514 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0404
_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)+(0.0487P)²+0.1389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                3175
_reflns_number_total             3659
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2859.cif
_cod_data_source_block           I
_cod_database_code               2222962
_cod_database_fobs_code          2222962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
S S1 0.01065(10) 0.44145(3) 0.66514(2) 0.02920(11) Uani d . 1 . .
O O1 0.3102(3) 0.29909(9) 0.71157(6) 0.0295(3) Uani d . 1 . .
N N1 0.4022(3) 0.33643(10) 0.59627(7) 0.0250(3) Uani d . 1 . .
C C1 0.5079(4) 0.23556(11) 0.68726(8) 0.0262(3) Uani d . 1 . .
C C2 0.6325(4) 0.16254(14) 0.72375(10) 0.0346(4) Uani d . 1 . .
H H2A 0.5895 0.1480 0.7710 0.042 Uiso calc R 1 . .
C C3 0.8271(4) 0.11206(14) 0.68500(10) 0.0366(4) Uani d . 1 . .
H H3A 0.9193 0.0621 0.7071 0.044 Uiso calc R 1 . .
C C4 0.8889(4) 0.13370(13) 0.61400(10) 0.0341(4) Uani d . 1 . .
H H4A 1.0209 0.0980 0.5900 0.041 Uiso calc R 1 . .
C C5 0.7576(4) 0.20749(13) 0.57839(9) 0.0292(4) Uani d . 1 . .
H H5A 0.7982 0.2218 0.5310 0.035 Uiso calc R 1 . .
C C6 0.5639(3) 0.25876(12) 0.61651(8) 0.0244(3) Uani d . 1 . .
C C7 0.2612(3) 0.35517(12) 0.65300(8) 0.0251(3) Uani d . 1 . .
C C8 -0.0098(4) 0.47588(12) 0.57236(8) 0.0289(3) Uani d . 1 . .
H H8A 0.1664 0.5008 0.5567 0.035 Uiso calc R 1 . .
H H8B -0.0536 0.4209 0.5432 0.035 Uiso calc R 1 . .
C C9 -0.2291(3) 0.55059(12) 0.56314(9) 0.0266(3) Uani d . 1 . .
C C10 -0.2762(4) 0.58747(12) 0.48943(9) 0.0264(3) Uani d . 1 . .
C C11 -0.4792(4) 0.65637(12) 0.47888(10) 0.0337(4) Uani d . 1 . .
H H11A -0.5823 0.6780 0.5175 0.040 Uiso calc R 1 . .
C C12 -0.5275(5) 0.69250(13) 0.41129(11) 0.0396(5) Uani d . 1 . .
H H12A -0.6630 0.7383 0.4045 0.048 Uiso calc R 1 . .
C C13 -0.3744(4) 0.66049(14) 0.35363(11) 0.0397(5) Uani d . 1 . .
H H13A -0.4070 0.6850 0.3082 0.048 Uiso calc R 1 . .
C C14 -0.1733(4) 0.59220(15) 0.36330(10) 0.0375(4) Uani d . 1 . .
H H14A -0.0713 0.5707 0.3244 0.045 Uiso calc R 1 . .
C C15 -0.1237(4) 0.55572(14) 0.43100(10) 0.0312(4) Uani d . 1 . .
H H15A 0.0120 0.5099 0.4374 0.037 Uiso calc R 1 . .
O O2 -0.3588(3) 0.57915(10) 0.61422(7) 0.0390(3) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 S1 C8 . . 95.81(8) ?
C7 O1 C1 . . 103.29(12) ?
C7 N1 C6 . . 103.67(14) ?
C2 C1 O1 . . 128.62(15) ?
C2 C1 C6 . . 124.18(18) ?
O1 C1 C6 . . 107.20(14) ?
C1 C2 C3 . . 115.13(17) ?
C1 C2 H2A . . 122.4 ?
C3 C2 H2A . . 122.4 ?
C2 C3 C4 . . 122.13(18) ?
C2 C3 H3A . . 118.9 ?
C4 C3 H3A . . 118.9 ?
C5 C4 C3 . . 121.36(18) ?
C5 C4 H4A . . 119.3 ?
C3 C4 H4A . . 119.3 ?
C6 C5 C4 . . 117.13(16) ?
C6 C5 H5A . . 121.4 ?
C4 C5 H5A . . 121.4 ?
C5 C6 C1 . . 120.06(16) ?
C5 C6 N1 . . 130.61(15) ?
C1 C6 N1 . . 109.33(15) ?
N1 C7 O1 . . 116.50(15) ?
N1 C7 S1 . . 128.59(13) ?
O1 C7 S1 . . 114.90(11) ?
C9 C8 S1 . . 109.67(12) ?
C9 C8 H8A . . 109.7 ?
S1 C8 H8A . . 109.7 ?
C9 C8 H8B . . 109.7 ?
S1 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
O2 C9 C10 . . 122.17(16) ?
O2 C9 C8 . . 120.60(16) ?
C10 C9 C8 . . 117.23(14) ?
C15 C10 C11 . . 119.18(16) ?
C15 C10 C9 . . 122.08(16) ?
C11 C10 C9 . . 118.74(16) ?
C12 C11 C10 . . 120.30(18) ?
C12 C11 H11A . . 119.8 ?
C10 C11 H11A . . 119.9 ?
C11 C12 C13 . . 120.01(18) ?
C11 C12 H12A . . 120.0 ?
C13 C12 H12A . . 120.0 ?
C14 C13 C12 . . 120.29(18) ?
C14 C13 H13A . . 119.9 ?
C12 C13 H13A . . 119.9 ?
C13 C14 C15 . . 119.98(19) ?
C13 C14 H14A . . 120.0 ?
C15 C14 H14A . . 120.0 ?
C14 C15 C10 . . 120.25(17) ?
C14 C15 H15A . . 119.9 ?
C10 C15 H15A . . 119.9 ?
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
S1 C7 . 1.7343(17) ?
S1 C8 . 1.8028(16) ?
O1 C7 . 1.3704(19) ?
O1 C1 . 1.389(2) ?
N1 C7 . 1.290(2) ?
N1 C6 . 1.398(2) ?
C1 C2 . 1.374(2) ?
C1 C6 . 1.389(2) ?
C2 C3 . 1.387(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.394(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.389(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.383(2) ?
C5 H5A . 0.9300 ?
C8 C9 . 1.507(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O2 . 1.212(2) ?
C9 C10 . 1.489(2) ?
C10 C15 . 1.393(3) ?
C10 C11 . 1.397(3) ?
C11 C12 . 1.381(2) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.385(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.383(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.386(3) ?
C14 H14A . 0.9300 ?
C15 H15A . 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
C5 H5A N1 3_556 0.93 2.56 3.395(2) 148.8 y
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 O1 C1 C2 . . . . -179.71(19) ?
C7 O1 C1 C6 . . . . 0.52(17) ?
O1 C1 C2 C3 . . . . -178.94(17) ?
C6 C1 C2 C3 . . . . 0.8(3) ?
C1 C2 C3 C4 . . . . -0.5(3) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C4 C5 C6 C1 . . . . 0.0(2) ?
C4 C5 C6 N1 . . . . 179.14(16) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
O1 C1 C6 C5 . . . . 179.26(15) ?
C2 C1 C6 N1 . . . . -179.86(17) ?
O1 C1 C6 N1 . . . . -0.08(18) ?
C7 N1 C6 C5 . . . . -179.68(17) ?
C7 N1 C6 C1 . . . . -0.43(18) ?
C6 N1 C7 O1 . . . . 0.83(19) ?
C6 N1 C7 S1 . . . . -178.00(13) ?
C1 O1 C7 N1 . . . . -0.89(19) ?
C1 O1 C7 S1 . . . . 178.11(12) ?
C8 S1 C7 N1 . . . . 8.41(18) ?
C8 S1 C7 O1 . . . . -170.44(13) ?
C7 S1 C8 C9 . . . . 177.42(12) ?
S1 C8 C9 O2 . . . . 0.7(2) ?
S1 C8 C9 C10 . . . . -179.75(13) ?
O2 C9 C10 C15 . . . . 178.88(17) ?
C8 C9 C10 C15 . . . . -0.7(2) ?
O2 C9 C10 C11 . . . . -0.8(3) ?
C8 C9 C10 C11 . . . . 179.60(16) ?
C15 C10 C11 C12 . . . . 0.0(3) ?
C9 C10 C11 C12 . . . . 179.69(17) ?
C10 C11 C12 C13 . . . . 0.0(3) ?
C11 C12 C13 C14 . . . . 0.2(3) ?
C12 C13 C14 C15 . . . . -0.2(3) ?
C13 C14 C15 C10 . . . . 0.1(3) ?
C11 C10 C15 C14 . . . . 0.0(3) ?
C9 C10 C15 C14 . . . . -179.73(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 596320
