#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/40/2224046.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_2224046
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(4-Fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran
;
_journal_coeditor_code           VM2006
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2766
_journal_paper_doi               10.1107/S1600536809041713
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C21 H15 F O S'
_chemical_formula_sum            'C21 H15 F O S'
_chemical_formula_weight         334.39
_chemical_name_systematic
;
2-(4-Fluorophenyl)-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
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                90.00
_cell_angle_beta                 116.076(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.621(6)
_cell_length_b                   7.192(4)
_cell_length_c                   11.642(6)
_cell_measurement_reflns_used    5096
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.44
_cell_volume                     798.8(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  HELIOS
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7602
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.435
_refine_ls_abs_structure_details 'Flack (1983), 1362 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0945P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                3147
_reflns_number_total             3339
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2006.cif
_cod_data_source_block           I
_cod_original_cell_volume        798.7(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2224046
_cod_database_fobs_code          2224046
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
S S 0.55481(6) 0.85482(12) 0.86991(5) 0.03285(19) Uani d . 1 . .
F F 1.25269(13) 0.7897(3) 1.00995(14) 0.0411(4) Uani d . 1 . .
O O 0.63814(15) 0.7920(2) 0.57182(13) 0.0245(4) Uani d . 1 . .
C C1 0.5612(2) 0.8243(3) 0.72327(19) 0.0223(5) Uani d . 1 . .
C C2 0.4412(2) 0.8143(3) 0.60022(19) 0.0227(5) Uani d . 1 . .
C C3 0.2962(2) 0.8170(3) 0.55929(18) 0.0221(5) Uani d . 1 . .
H H3 0.2591 0.8309 0.6178 0.027 Uiso calc R 1 . .
C C4 0.2085(2) 0.7984(3) 0.42913(19) 0.0212(4) Uani d . 1 . .
C C5 0.2683(2) 0.7823(4) 0.3427(2) 0.0260(5) Uani d . 1 . .
H H5 0.2089 0.7725 0.2558 0.031 Uiso calc R 1 . .
C C6 0.4106(2) 0.7804(4) 0.38153(19) 0.0251(5) Uani d . 1 . .
H H6 0.4485 0.7701 0.3234 0.030 Uiso calc R 1 . .
C C7 0.4948(2) 0.7947(3) 0.5121(2) 0.0230(5) Uani d . 1 . .
C C8 0.6759(2) 0.8099(3) 0.70145(19) 0.0234(5) Uani d . 1 . .
C C9 0.8275(2) 0.8059(3) 0.78298(19) 0.0229(5) Uani d . 1 . .
C C10 0.9163(2) 0.7210(4) 0.7396(2) 0.0251(5) Uani d . 1 . .
H H10 0.8786 0.6685 0.6584 0.030 Uiso calc R 1 . .
C C11 1.0589(2) 0.7133(4) 0.8147(2) 0.0297(5) Uani d . 1 . .
H H11 1.1177 0.6548 0.7858 0.036 Uiso calc R 1 . .
C C12 1.1119(2) 0.7952(4) 0.9344(2) 0.0283(5) Uani d . 1 . .
C C13 1.0284(2) 0.8825(4) 0.9805(2) 0.0290(5) Uani d . 1 . .
H H13 1.0674 0.9376 1.0610 0.035 Uiso calc R 1 . .
C C14 0.8855(2) 0.8868(4) 0.9050(2) 0.0262(5) Uani d . 1 . .
H H14 0.8273 0.9437 0.9352 0.031 Uiso calc R 1 . .
C C15 0.05328(19) 0.7926(3) 0.38285(19) 0.0219(4) Uani d . 1 . .
C C16 -0.0110(2) 0.8798(4) 0.4505(2) 0.0260(5) Uani d . 1 . .
H H16 0.0430 0.9478 0.5238 0.031 Uiso calc R 1 . .
C C17 -0.1552(2) 0.8657(4) 0.4092(2) 0.0301(5) Uani d . 1 . .
H H17 -0.1969 0.9239 0.4551 0.036 Uiso calc R 1 . .
C C18 -0.2363(2) 0.7662(4) 0.3008(2) 0.0332(6) Uani d . 1 . .
H H18 -0.3322 0.7546 0.2748 0.040 Uiso calc R 1 . .
C C19 -0.1752(2) 0.6834(4) 0.2304(2) 0.0335(6) Uani d . 1 . .
H H19 -0.2304 0.6199 0.1554 0.040 Uiso calc R 1 . .
C C20 -0.0313(2) 0.6951(4) 0.2718(2) 0.0263(5) Uani d . 1 . .
H H20 0.0094 0.6373 0.2249 0.032 Uiso calc R 1 . .
C C21 0.4797(3) 0.6375(5) 0.8842(3) 0.0451(7) Uani d . 1 . .
H H21A 0.5406 0.5375 0.8863 0.068 Uiso calc R 1 . .
H H21B 0.3899 0.6218 0.8123 0.068 Uiso calc R 1 . .
H H21C 0.4686 0.6371 0.9617 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 0.0033 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'
F F 0.0171 0.0103 '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
C1 S C21 . . 100.97(13) ?
C7 O C8 . . 106.04(16) ?
C8 C1 C2 . . 106.57(18) ?
C8 C1 S . . 128.05(16) ?
C2 C1 S . . 125.37(15) ?
C7 C2 C3 . . 119.98(19) ?
C7 C2 C1 . . 105.69(18) ?
C3 C2 C1 . . 134.31(19) ?
C4 C3 C2 . . 118.64(19) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 119.2(2) ?
C3 C4 C15 . . 119.99(19) ?
C5 C4 C15 . . 120.80(19) ?
C6 C5 C4 . . 122.8(2) ?
C6 C5 H5 . . 118.6 ?
C4 C5 H5 . . 118.6 ?
C5 C6 C7 . . 116.5(2) ?
C5 C6 H6 . . 121.8 ?
C7 C6 H6 . . 121.8 ?
O C7 C2 . . 110.71(18) ?
O C7 C6 . . 126.35(19) ?
C2 C7 C6 . . 122.9(2) ?
C1 C8 O . . 110.98(18) ?
C1 C8 C9 . . 134.7(2) ?
O C8 C9 . . 114.35(18) ?
C10 C9 C14 . . 118.9(2) ?
C10 C9 C8 . . 120.0(2) ?
C14 C9 C8 . . 121.05(19) ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 118.0(2) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
F C12 C13 . . 118.3(2) ?
F C12 C11 . . 118.9(2) ?
C13 C12 C11 . . 122.7(2) ?
C12 C13 C14 . . 118.6(2) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.4(2) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
C20 C15 C16 . . 118.23(19) ?
C20 C15 C4 . . 120.47(19) ?
C16 C15 C4 . . 121.28(19) ?
C17 C16 C15 . . 120.5(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.4(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 120.0(2) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C18 C19 C20 . . 120.0(2) ?
C18 C19 H19 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 . 1.752(2) ?
S C21 . 1.795(3) ?
F C12 . 1.362(2) ?
O C7 . 1.368(3) ?
O C8 . 1.387(3) ?
C1 C8 . 1.353(3) ?
C1 C2 . 1.441(3) ?
C2 C7 . 1.381(3) ?
C2 C3 . 1.398(3) ?
C3 C4 . 1.393(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.411(3) ?
C4 C15 . 1.493(3) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.388(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.467(3) ?
C9 C10 . 1.391(3) ?
C9 C14 . 1.403(3) ?
C10 C11 . 1.378(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(3) ?
C13 C14 . 1.380(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C20 . 1.396(3) ?
C15 C16 . 1.397(3) ?
C16 C17 . 1.393(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.375(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.384(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.389(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_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 . . . . -113.4(2) ?
C21 S C1 C2 . . . . 68.3(2) ?
C8 C1 C2 C7 . . . . -0.2(3) ?
S C1 C2 C7 . . . . 178.46(18) ?
C8 C1 C2 C3 . . . . 178.5(3) ?
S C1 C2 C3 . . . . -2.9(4) ?
C7 C2 C3 C4 . . . . 0.4(3) ?
C1 C2 C3 C4 . . . . -178.1(3) ?
C2 C3 C4 C5 . . . . -1.6(3) ?
C2 C3 C4 C15 . . . . 177.4(2) ?
C3 C4 C5 C6 . . . . 1.3(4) ?
C15 C4 C5 C6 . . . . -177.7(2) ?
C4 C5 C6 C7 . . . . 0.2(4) ?
C8 O C7 C2 . . . . 0.2(3) ?
C8 O C7 C6 . . . . -179.9(2) ?
C3 C2 C7 O . . . . -178.9(2) ?
C1 C2 C7 O . . . . 0.0(3) ?
C3 C2 C7 C6 . . . . 1.2(4) ?
C1 C2 C7 C6 . . . . -180.0(2) ?
C5 C6 C7 O . . . . 178.6(2) ?
C5 C6 C7 C2 . . . . -1.5(4) ?
C2 C1 C8 O . . . . 0.3(3) ?
S C1 C8 O . . . . -178.31(17) ?
C2 C1 C8 C9 . . . . -178.4(3) ?
S C1 C8 C9 . . . . 3.0(4) ?
C7 O C8 C1 . . . . -0.3(3) ?
C7 O C8 C9 . . . . 178.73(19) ?
C1 C8 C9 C10 . . . . 155.3(3) ?
O C8 C9 C10 . . . . -23.3(3) ?
C1 C8 C9 C14 . . . . -24.7(4) ?
O C8 C9 C14 . . . . 156.6(2) ?
C14 C9 C10 C11 . . . . 0.8(4) ?
C8 C9 C10 C11 . . . . -179.3(2) ?
C9 C10 C11 C12 . . . . -0.9(4) ?
C10 C11 C12 F . . . . -179.8(2) ?
C10 C11 C12 C13 . . . . 0.2(4) ?
F C12 C13 C14 . . . . -179.3(2) ?
C11 C12 C13 C14 . . . . 0.8(4) ?
C12 C13 C14 C9 . . . . -0.9(4) ?
C10 C9 C14 C13 . . . . 0.2(4) ?
C8 C9 C14 C13 . . . . -179.8(2) ?
C3 C4 C15 C20 . . . . -150.9(2) ?
C5 C4 C15 C20 . . . . 28.0(4) ?
C3 C4 C15 C16 . . . . 27.4(3) ?
C5 C4 C15 C16 . . . . -153.6(2) ?
C20 C15 C16 C17 . . . . 1.4(4) ?
C4 C15 C16 C17 . . . . -177.0(2) ?
C15 C16 C17 C18 . . . . -0.2(4) ?
C16 C17 C18 C19 . . . . -1.6(4) ?
C17 C18 C19 C20 . . . . 2.3(4) ?
C18 C19 C20 C15 . . . . -1.2(4) ?
C16 C15 C20 C19 . . . . -0.7(4) ?
C4 C15 C20 C19 . . . . 177.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743541
