#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/11/2211197.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_2211197
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Kang, Byoung Won'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-Methylsulfanyl-2,5-diphenyl-1-benzofuran
;
_journal_coeditor_code           SJ2122
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4796
_journal_page_last               o4797
_journal_paper_doi               10.1107/S1600536806039596
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H16 O S'
_chemical_formula_moiety         'C21 H16 O S'
_chemical_formula_sum            'C21 H16 O S'
_chemical_formula_weight         316.40
_chemical_name_systematic
;
3-Methylsulfanyl-2,5-diphenyl-1-benzofuran
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                112.6900(10)
_cell_angle_beta                 94.2960(10)
_cell_angle_gamma                114.7640(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2050(6)
_cell_length_b                   9.4362(6)
_cell_length_c                   11.5415(7)
_cell_measurement_reflns_used    4323
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.50
_cell_volume                     805.70(9)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6966
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.4767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2952
_reflns_number_total             3443
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2122.cif
_cod_data_source_block           I
_cod_database_code               2211197
_cod_database_fobs_code          2211197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S S 0.76159(6) 0.58822(5) 0.56992(5) 0.03169(14) Uani d . 1
O O 0.46634(16) 0.09758(15) 0.29129(12) 0.0301(3) Uani d . 1
C C1 0.8153(3) 0.3540(3) 0.0432(2) 0.0365(4) Uani d . 1
H H1 0.8624 0.3711 -0.0220 0.044 Uiso calc R 1
C C2 0.8211(3) 0.4948(3) 0.1487(2) 0.0367(4) Uani d . 1
H H2 0.8730 0.6064 0.1542 0.044 Uiso calc R 1
C C3 0.7503(2) 0.4701(2) 0.24532(19) 0.0320(4) Uani d . 1
H H3 0.7546 0.5652 0.3153 0.038 Uiso calc R 1
C C4 0.6721(2) 0.3029(2) 0.23873(18) 0.0270(4) Uani d . 1
C C5 0.6681(2) 0.1623(2) 0.13207(18) 0.0300(4) Uani d . 1
H H5 0.6169 0.0504 0.1261 0.036 Uiso calc R 1
C C6 0.7391(2) 0.1882(2) 0.03598(19) 0.0343(4) Uani d . 1
H H6 0.7358 0.0938 -0.0340 0.041 Uiso calc R 1
C C7 0.5931(2) 0.2691(2) 0.33731(18) 0.0273(4) Uani d . 1
C C8 0.6145(2) 0.3662(2) 0.46682(17) 0.0253(4) Uani d . 1
C C9 0.4949(2) 0.2500(2) 0.50716(17) 0.0248(4) Uani d . 1
C C10 0.4515(2) 0.2679(2) 0.62262(17) 0.0265(4) Uani d . 1
H H10 0.5081 0.3751 0.6981 0.032 Uiso calc R 1
C C11 0.3215(2) 0.1227(2) 0.62402(18) 0.0276(4) Uani d . 1
C C12 0.2384(2) -0.0400(2) 0.50777(19) 0.0310(4) Uani d . 1
H H12 0.1524 -0.1364 0.5093 0.037 Uiso calc R 1
C C13 0.2807(2) -0.0599(2) 0.39302(18) 0.0314(4) Uani d . 1
H H13 0.2261 -0.1671 0.3175 0.038 Uiso calc R 1
C C14 0.4086(2) 0.0874(2) 0.39533(17) 0.0281(4) Uani d . 1
C C15 0.2671(2) 0.1392(2) 0.74441(18) 0.0291(4) Uani d . 1
C C16 0.3819(3) 0.2457(2) 0.86862(19) 0.0349(4) Uani d . 1
H H16 0.4950 0.3054 0.8766 0.042 Uiso calc R 1
C C17 0.3283(3) 0.2630(3) 0.9802(2) 0.0433(5) Uani d . 1
H H17 0.4057 0.3341 1.0624 0.052 Uiso calc R 1
C C18 0.1601(3) 0.1747(3) 0.9696(2) 0.0455(6) Uani d . 1
H H18 0.1244 0.1871 1.0444 0.055 Uiso calc R 1
C C19 0.0455(3) 0.0682(3) 0.8473(2) 0.0424(5) Uani d . 1
H H19 -0.0675 0.0085 0.8399 0.051 Uiso calc R 1
C C20 0.0981(3) 0.0501(2) 0.7358(2) 0.0340(4) Uani d . 1
H H20 0.0199 -0.0223 0.6540 0.041 Uiso calc R 1
C C21 0.8985(3) 0.5597(3) 0.6668(3) 0.0622(8) Uani d . 1
H H21A 0.8370 0.4957 0.7100 0.093 Uiso calc R 1
H H21B 0.9868 0.6728 0.7311 0.093 Uiso calc R 1
H H21C 0.9451 0.4955 0.6112 0.093 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C8 S C21 99.39(9) yes
C14 O C7 106.60(10) yes
C6 C1 C2 119.6(2) ?
C6 C1 H1 120.2 ?
C2 C1 H1 120.2 ?
C3 C2 C1 120.5(2) ?
C3 C2 H2 119.7 ?
C1 C2 H2 119.7 ?
C2 C3 C4 120.5(2) ?
C2 C3 H3 119.8 ?
C4 C3 H3 119.8 ?
C3 C4 C5 118.4(2) ?
C3 C4 C7 122.7(2) ?
C5 C4 C7 119.0(2) ?
C6 C5 C4 120.8(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
C5 C6 C1 120.3(2) ?
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
C8 C7 O 110.6(2) ?
C8 C7 C4 135.3(2) ?
O C7 C4 114.1(2) ?
C7 C8 C9 106.8(2) ?
C7 C8 S 127.90(10) ?
C9 C8 S 125.20(10) ?
C10 C9 C14 119.3(2) ?
C10 C9 C8 135.3(2) ?
C14 C9 C8 105.4(2) ?
C9 C10 C11 119.2(2) ?
C9 C10 H10 120.4 ?
C11 C10 H10 120.4 ?
C10 C11 C12 119.3(2) ?
C10 C11 C15 120.6(2) ?
C12 C11 C15 120.1(2) ?
C13 C12 C11 122.2(2) ?
C13 C12 H12 118.9 ?
C11 C12 H12 118.9 ?
C12 C13 C14 116.8(2) ?
C12 C13 H13 121.6 ?
C14 C13 H13 121.6 ?
O C14 C13 126.2(2) ?
O C14 C9 110.6(2) ?
C13 C14 C9 123.3(2) ?
C16 C15 C20 118.3(2) ?
C16 C15 C11 121.3(2) ?
C20 C15 C11 120.4(2) ?
C17 C16 C15 120.5(2) ?
C17 C16 H16 119.7 ?
C15 C16 H16 119.7 ?
C18 C17 C16 120.3(2) ?
C18 C17 H17 119.9 ?
C16 C17 H17 119.9 ?
C19 C18 C17 119.7(2) ?
C19 C18 H18 120.1 ?
C17 C18 H18 120.1 ?
C18 C19 C20 120.3(2) ?
C18 C19 H19 119.9 ?
C20 C19 H19 119.9 ?
C19 C20 C15 120.9(2) ?
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_distance
_geom_bond_publ_flag
S C8 1.760(2) yes
S C21 1.793(2) yes
O C14 1.370(2) yes
O C7 1.387(2) yes
C1 C6 1.385(3) ?
C1 C2 1.391(3) ?
C1 H1 0.9300 ?
C2 C3 1.379(3) ?
C2 H2 0.9300 ?
C3 C4 1.400(2) ?
C3 H3 0.9300 ?
C4 C5 1.403(3) ?
C4 C7 1.461(3) ?
C5 C6 1.379(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.364(3) ?
C8 C9 1.446(2) ?
C9 C10 1.388(3) ?
C9 C14 1.396(2) ?
C10 C11 1.398(2) ?
C10 H10 0.9300 ?
C11 C12 1.420(2) ?
C11 C15 1.486(3) ?
C12 C13 1.374(3) ?
C12 H12 0.9300 ?
C13 C14 1.383(3) ?
C13 H13 0.9300 ?
C15 C16 1.398(3) ?
C15 C20 1.398(3) ?
C16 C17 1.389(3) ?
C16 H16 0.9300 ?
C17 C18 1.385(3) ?
C17 H17 0.9300 ?
C18 C19 1.382(3) ?
C18 H18 0.9300 ?
C19 C20 1.382(3) ?
C19 H19 0.9300 ?
C20 H20 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
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
C6 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 0.1(3)
C2 C3 C4 C7 -179.1(2)
C3 C4 C5 C6 -0.1(3)
C7 C4 C5 C6 179.1(2)
C4 C5 C6 C1 -0.2(3)
C2 C1 C6 C5 0.6(3)
C14 O C7 C8 -0.6(2)
C14 O C7 C4 178.80(10)
C3 C4 C7 C8 -26.9(3)
C5 C4 C7 C8 153.9(2)
C3 C4 C7 O 153.9(2)
C5 C4 C7 O -25.3(2)
O C7 C8 C9 0.38(19)
C4 C7 C8 C9 -178.9(2)
O C7 C8 S 178.60(10)
C4 C7 C8 S -0.7(3)
C21 S C8 C7 -107.4(2)
C21 S C8 C9 70.5(2)
C7 C8 C9 C10 -178.4(2)
S C8 C9 C10 3.3(3)
S C8 C9 C14 -178.30(10)
C14 C9 C10 C11 -0.3(2)
C8 C9 C10 C11 177.9(2)
C9 C10 C11 C12 0.7(2)
C9 C10 C11 C15 -177.4(2)
C10 C11 C12 C13 -0.3(3)
C15 C11 C12 C13 177.8(2)
C11 C12 C13 C14 -0.4(3)
C7 O C14 C13 179.4(2)
C7 O C14 C9 0.60(19)
C12 C13 C14 O -177.8(2)
C12 C13 C14 C9 0.8(3)
C10 C9 C14 O 178.40(10)
C10 C9 C14 C13 -0.5(3)
C8 C9 C14 C13 -179.2(2)
C10 C11 C15 C16 -37.1(2)
C12 C11 C15 C16 144.8(2)
C10 C11 C15 C20 141.7(2)
C12 C11 C15 C20 -36.4(2)
C20 C15 C16 C17 -0.5(3)
C11 C15 C16 C17 178.4(2)
C15 C16 C17 C18 0.0(3)
C16 C17 C18 C19 0.4(3)
C17 C18 C19 C20 -0.3(3)
C18 C19 C20 C15 -0.3(3)
C16 C15 C20 C19 0.6(3)
C11 C15 C20 C19 -178.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126090
