#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225536.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_2225536
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(4-Chlorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran
;
_journal_coeditor_code           FL2295
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o802
_journal_paper_doi               10.1107/S1600536810008706
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H15 Cl O S'
_chemical_formula_moiety         'C21 H15 Cl O S'
_chemical_formula_sum            'C21 H15 Cl O S'
_chemical_formula_weight         350.84
_chemical_name_systematic
;
2-(4-Chlorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 115.132(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9210(10)
_cell_length_b                   7.2225(8)
_cell_length_c                   11.7400(10)
_cell_measurement_reflns_used    4886
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.36
_cell_volume                     838.35(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker HELIOS graded multilayer optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7754
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.9505
_exptl_absorpt_correction_T_min  0.9106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.229
_refine_ls_abs_structure_details 'Flack (1983), 1505 Friedel pairs'
_refine_ls_abs_structure_Flack   0.35(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3571
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/esd_max         0.000
_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)+(0.0510P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                3376
_reflns_number_total             3571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2295.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        838.35(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225536
_cod_database_fobs_code          2225536
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
Cl Cl -0.26159(5) 0.53997(9) -0.01679(5) 0.04418(14) Uani d . 1 . .
S S 0.45654(5) 0.50246(9) 0.13481(4) 0.04300(16) Uani d . 1 . .
O O 0.37078(12) 0.5417(2) 0.43085(10) 0.0297(3) Uani d . 1 . .
C C1 0.44798(18) 0.5179(3) 0.28020(15) 0.0289(4) Uani d . 1 . .
C C2 0.56317(17) 0.5235(3) 0.40109(15) 0.0267(3) Uani d . 1 . .
C C3 0.70372(18) 0.5202(3) 0.44147(15) 0.0276(4) Uani d . 1 . .
H H3 0.7412 0.5078 0.3822 0.033 Uiso calc R 1 . .
C C4 0.78803(17) 0.5353(3) 0.56955(15) 0.0270(3) Uani d . 1 . .
C C5 0.72841(19) 0.5488(3) 0.65544(16) 0.0311(4) Uani d . 1 . .
H H5 0.7859 0.5565 0.7428 0.037 Uiso calc R 1 . .
C C6 0.58971(19) 0.5512(3) 0.61716(16) 0.0321(4) Uani d . 1 . .
H H6 0.5513 0.5607 0.6759 0.039 Uiso calc R 1 . .
C C7 0.51007(18) 0.5391(3) 0.48929(15) 0.0287(3) Uani d . 1 . .
C C8 0.33570(18) 0.5302(3) 0.30249(15) 0.0286(4) Uani d . 1 . .
C C9 0.19012(18) 0.5351(3) 0.22349(15) 0.0281(3) Uani d . 1 . .
C C10 0.1017(2) 0.6099(3) 0.26900(18) 0.0297(4) Uani d . 1 . .
H H10 0.1372 0.6584 0.3520 0.036 Uiso calc R 1 . .
C C11 -0.0366(2) 0.6149(3) 0.19605(19) 0.0329(4) Uani d . 1 . .
H H11 -0.0955 0.6672 0.2281 0.039 Uiso calc R 1 . .
C C12 -0.08758(18) 0.5422(3) 0.07541(16) 0.0304(4) Uani d . 1 . .
C C13 -0.0032(2) 0.4675(3) 0.02688(17) 0.0335(4) Uani d . 1 . .
H H13 -0.0399 0.4188 -0.0561 0.040 Uiso calc R 1 . .
C C14 0.1356(2) 0.4641(3) 0.10026(18) 0.0325(4) Uani d . 1 . .
H H14 0.1939 0.4135 0.0670 0.039 Uiso calc R 1 . .
C C15 0.93761(17) 0.5412(3) 0.61447(15) 0.0271(3) Uani d . 1 . .
C C16 1.0017(2) 0.4543(3) 0.54744(18) 0.0316(4) Uani d . 1 . .
H H16 0.9492 0.3851 0.4739 0.038 Uiso calc R 1 . .
C C17 1.1406(2) 0.4677(3) 0.58677(19) 0.0364(4) Uani d . 1 . .
H H17 1.1821 0.4085 0.5399 0.044 Uiso calc R 1 . .
C C18 1.2186(2) 0.5668(3) 0.6939(2) 0.0413(5) Uani d . 1 . .
H H18 1.3134 0.5781 0.7198 0.050 Uiso calc R 1 . .
C C19 1.1582(2) 0.6494(3) 0.7630(2) 0.0416(5) Uani d . 1 . .
H H19 1.2119 0.7152 0.8377 0.050 Uiso calc R 1 . .
C C20 1.0191(2) 0.6369(3) 0.72411(19) 0.0337(4) Uani d . 1 . .
H H20 0.9789 0.6941 0.7727 0.040 Uiso calc R 1 . .
C C21 0.5393(3) 0.7197(4) 0.1356(2) 0.0511(6) Uani d . 1 . .
H H21A 0.6327 0.7160 0.2004 0.077 Uiso calc R 1 . .
H H21B 0.4906 0.8211 0.1538 0.077 Uiso calc R 1 . .
H H21C 0.5394 0.7398 0.0531 0.077 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 0.0033 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'
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'
Cl Cl 0.1484 0.1585 '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
C1 S C21 . . 99.95(11) ?
C7 O C8 . . 106.06(12) ?
C8 C1 C2 . . 106.82(14) ?
C8 C1 S . . 128.07(14) ?
C2 C1 S . . 125.10(13) ?
C7 C2 C3 . . 119.55(15) ?
C7 C2 C1 . . 105.65(15) ?
C3 C2 C1 . . 134.79(14) ?
C4 C3 C2 . . 119.35(14) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 118.70(16) ?
C3 C4 C15 . . 120.45(14) ?
C5 C4 C15 . . 120.84(15) ?
C6 C5 C4 . . 122.67(16) ?
C6 C5 H5 . . 118.7 ?
C4 C5 H5 . . 118.7 ?
C7 C6 C5 . . 116.66(15) ?
C7 C6 H6 . . 121.7 ?
C5 C6 H6 . . 121.7 ?
O C7 C6 . . 126.34(14) ?
O C7 C2 . . 110.60(14) ?
C6 C7 C2 . . 123.06(16) ?
C1 C8 O . . 110.86(15) ?
C1 C8 C9 . . 134.88(15) ?
O C8 C9 . . 114.26(14) ?
C10 C9 C14 . . 118.36(17) ?
C10 C9 C8 . . 120.64(15) ?
C14 C9 C8 . . 121.00(16) ?
C11 C10 C9 . . 121.59(16) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C10 C11 C12 . . 118.75(17) ?
C10 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
C13 C12 C11 . . 121.37(17) ?
C13 C12 Cl . . 118.84(14) ?
C11 C12 Cl . . 119.78(14) ?
C12 C13 C14 . . 119.59(17) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C9 . . 120.33(17) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
C20 C15 C16 . . 117.61(17) ?
C20 C15 C4 . . 120.92(16) ?
C16 C15 C4 . . 121.46(16) ?
C17 C16 C15 . . 121.11(18) ?
C17 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C18 C17 C16 . . 120.21(18) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C19 C18 C17 . . 119.66(19) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
C18 C19 C20 . . 120.46(19) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.92(18) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
S C21 H21A . . 109.5 ?
S C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
S C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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
Cl C12 . 1.7425(18) ?
S C1 . 1.7523(15) ?
S C21 . 1.809(3) ?
O C7 . 1.378(2) ?
O C8 . 1.3907(18) ?
C1 C8 . 1.361(2) ?
C1 C2 . 1.443(2) ?
C2 C7 . 1.390(2) ?
C2 C3 . 1.401(2) ?
C3 C4 . 1.394(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.417(2) ?
C4 C15 . 1.489(2) ?
C5 C6 . 1.385(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.382(2) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.462(2) ?
C9 C10 . 1.396(3) ?
C9 C14 . 1.407(2) ?
C10 C11 . 1.384(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.386(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.382(3) ?
C13 C14 . 1.390(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C20 . 1.397(3) ?
C15 C16 . 1.404(2) ?
C16 C17 . 1.388(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.382(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.381(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.391(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
C21 S C1 C8 . . . . 114.7(2) ?
C21 S C1 C2 . . . . -63.9(2) ?
C8 C1 C2 C7 . . . . 0.1(2) ?
S C1 C2 C7 . . . . 178.95(16) ?
C8 C1 C2 C3 . . . . -178.6(2) ?
S C1 C2 C3 . . . . 0.3(4) ?
C7 C2 C3 C4 . . . . -0.9(3) ?
C1 C2 C3 C4 . . . . 177.6(2) ?
C2 C3 C4 C5 . . . . 1.6(3) ?
C2 C3 C4 C15 . . . . -177.07(18) ?
C3 C4 C5 C6 . . . . -1.3(3) ?
C15 C4 C5 C6 . . . . 177.4(2) ?
C4 C5 C6 C7 . . . . 0.2(3) ?
C8 O C7 C6 . . . . 178.7(2) ?
C8 O C7 C2 . . . . -0.9(2) ?
C5 C6 C7 O . . . . -179.0(2) ?
C5 C6 C7 C2 . . . . 0.5(3) ?
C3 C2 C7 O . . . . 179.40(17) ?
C1 C2 C7 O . . . . 0.5(2) ?
C3 C2 C7 C6 . . . . -0.2(3) ?
C1 C2 C7 C6 . . . . -179.1(2) ?
C2 C1 C8 O . . . . -0.6(3) ?
S C1 C8 O . . . . -179.45(15) ?
C2 C1 C8 C9 . . . . 178.9(2) ?
S C1 C8 C9 . . . . 0.1(4) ?
C7 O C8 C1 . . . . 0.9(2) ?
C7 O C8 C9 . . . . -178.73(16) ?
C1 C8 C9 C10 . . . . -158.1(2) ?
O C8 C9 C10 . . . . 21.4(3) ?
C1 C8 C9 C14 . . . . 22.2(4) ?
O C8 C9 C14 . . . . -158.26(19) ?
C14 C9 C10 C11 . . . . 0.1(3) ?
C8 C9 C10 C11 . . . . -179.60(18) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . -0.8(3) ?
C10 C11 C12 Cl . . . . 178.00(16) ?
C11 C12 C13 C14 . . . . 0.3(3) ?
Cl C12 C13 C14 . . . . -178.46(15) ?
C12 C13 C14 C9 . . . . 0.3(3) ?
C10 C9 C14 C13 . . . . -0.5(3) ?
C8 C9 C14 C13 . . . . 179.14(18) ?
C3 C4 C15 C20 . . . . 150.24(19) ?
C5 C4 C15 C20 . . . . -28.4(3) ?
C3 C4 C15 C16 . . . . -28.6(3) ?
C5 C4 C15 C16 . . . . 152.8(2) ?
C20 C15 C16 C17 . . . . -1.9(3) ?
C4 C15 C16 C17 . . . . 176.97(18) ?
C15 C16 C17 C18 . . . . 0.4(3) ?
C16 C17 C18 C19 . . . . 1.3(3) ?
C17 C18 C19 C20 . . . . -1.4(3) ?
C18 C19 C20 C15 . . . . -0.2(3) ?
C16 C15 C20 C19 . . . . 1.8(3) ?
C4 C15 C20 C19 . . . . -177.09(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744655
