#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/45/2214570.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_2214570
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(3-Methylsulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid
;
_journal_coeditor_code           CF2113
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3468
_journal_page_last               o3468
_journal_paper_doi               10.1107/S1600536807033326
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H14 O3 S'
_chemical_formula_moiety         'C17 H14 O3 S'
_chemical_formula_sum            'C17 H14 O3 S'
_chemical_formula_weight         298.34
_chemical_melting_point          .46E-305
_chemical_name_systematic
;
2-(3-Methylsulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.777(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.857(2)
_cell_length_b                   11.274(2)
_cell_length_c                   11.978(2)
_cell_measurement_reflns_used    1299
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.48
_cell_volume                     1466.0(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_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      173(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker SMART 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  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5235
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0599
_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)+(0.0737P)²+0.4676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                1573
_reflns_number_total             2390
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2113.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -p_2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214570
_cod_database_fobs_code          2214570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
S S 0.14850(10) 0.23359(9) 0.57947(9) 0.0309(3) Uani d . 1
O O1 0.0811(2) 0.5739(2) 0.6300(2) 0.0266(7) Uani d . 1
O O2 -0.1048(2) 0.4462(2) 0.9100(2) 0.0265(7) Uani d . 1
O O3 0.0877(2) 0.5047(3) 0.8757(2) 0.0297(7) Uani d D 1
H H1 0.099(6) 0.526(6) 0.954(5) 0.11(2) Uiso d D 1
C C1 0.1424(3) 0.3886(3) 0.5843(3) 0.0198(9) Uani d . 1
C C2 0.2125(3) 0.4721(3) 0.5198(3) 0.0189(9) Uani d . 1
C C3 0.3023(3) 0.4618(3) 0.4376(3) 0.0203(9) Uani d . 1
H H3 0.3308 0.3859 0.4150 0.024 Uiso calc R 1
C C4 0.3495(3) 0.5651(3) 0.3894(3) 0.0200(9) Uani d . 1
C C5 0.3068(3) 0.6753(4) 0.4257(3) 0.0232(9) Uani d . 1
H H5 0.3402 0.7450 0.3933 0.028 Uiso calc R 1
C C6 0.2181(3) 0.6875(4) 0.5067(3) 0.0250(9) Uani d . 1
H H6 0.1906 0.7630 0.5313 0.030 Uiso calc R 1
C C7 0.1722(3) 0.5836(3) 0.5494(3) 0.0205(9) Uani d . 1
C C8 0.0665(3) 0.4546(4) 0.6483(3) 0.0234(9) Uani d . 1
C C9 -0.0320(3) 0.4211(4) 0.7269(3) 0.0307(11) Uani d . 1
H H9A -0.0398 0.3336 0.7260 0.037 Uiso calc R 1
H H9B -0.1107 0.4540 0.6979 0.037 Uiso calc R 1
C C10 -0.0165(3) 0.4601(3) 0.8469(3) 0.0220(9) Uani d . 1
C C11 0.4407(3) 0.5580(3) 0.2981(3) 0.0198(9) Uani d . 1
C C12 0.4281(3) 0.6317(4) 0.2039(3) 0.0275(10) Uani d . 1
H H12 0.3616 0.6863 0.1987 0.033 Uiso calc R 1
C C13 0.5120(4) 0.6246(4) 0.1194(3) 0.0332(11) Uani d . 1
H H13 0.5007 0.6726 0.0549 0.040 Uiso calc R 1
C C14 0.6120(4) 0.5496(4) 0.1259(3) 0.0325(11) Uani d . 1
H H14 0.6703 0.5469 0.0674 0.039 Uiso calc R 1
C C15 0.6258(3) 0.4784(4) 0.2191(3) 0.0254(10) Uani d . 1
H H15 0.6948 0.4268 0.2249 0.030 Uiso calc R 1
C C16 0.5411(3) 0.4812(3) 0.3036(3) 0.0209(9) Uani d . 1
H H16 0.5513 0.4303 0.3663 0.025 Uiso calc R 1
C C17 0.2897(4) 0.2070(4) 0.6565(4) 0.0542(15) Uani d . 1
H H17A 0.3571 0.2508 0.6218 0.081 Uiso calc R 1
H H17B 0.3084 0.1220 0.6559 0.081 Uiso calc R 1
H H17C 0.2803 0.2338 0.7338 0.081 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S C17 100.4(2)
C8 O1 C7 105.8(3)
C10 O3 H1 117(4)
C8 C1 C2 105.9(4)
C8 C1 S 126.2(3)
C2 C1 S 127.9(3)
C7 C2 C3 118.9(3)
C7 C2 C1 106.6(3)
C3 C2 C1 134.5(4)
C4 C3 C2 118.9(3)
C4 C3 H3 120.5
C2 C3 H3 120.5
C5 C4 C3 119.1(4)
C5 C4 C11 120.2(3)
C3 C4 C11 120.6(3)
C6 C5 C4 122.9(4)
C6 C5 H5 118.5
C4 C5 H5 118.5
C7 C6 C5 115.8(4)
C7 C6 H6 122.1
C5 C6 H6 122.1
C6 C7 C2 124.3(4)
C6 C7 O1 126.0(3)
C2 C7 O1 109.6(3)
C1 C8 O1 112.0(3)
C1 C8 C9 132.0(4)
O1 C8 C9 115.9(3)
C8 C9 C10 117.3(3)
C8 C9 H9A 108.0
C10 C9 H9A 108.0
C8 C9 H9B 108.0
C10 C9 H9B 108.0
H9A C9 H9B 107.2
O2 C10 O3 125.0(3)
O2 C10 C9 117.8(3)
O3 C10 C9 117.2(4)
C16 C11 C12 118.2(4)
C16 C11 C4 121.8(3)
C12 C11 C4 120.0(3)
C13 C12 C11 119.9(4)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 121.7(4)
C12 C13 H13 119.2
C14 C13 H13 119.2
C13 C14 C15 118.6(4)
C13 C14 H14 120.7
C15 C14 H14 120.7
C16 C15 C14 121.0(4)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C11 120.6(4)
C15 C16 H16 119.7
C11 C16 H16 119.7
S C17 H17A 109.5
S C17 H17B 109.5
H17A C17 H17B 109.5
S C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C1 1.749(4)
S C17 1.804(4)
O1 C8 1.372(5)
O1 C7 1.397(4)
O2 C10 1.238(4)
O3 C10 1.281(4)
O3 H1 0.97(6)
C1 C8 1.356(5)
C1 C2 1.441(5)
C2 C7 1.379(5)
C2 C3 1.399(5)
C3 C4 1.401(5)
C3 H3 0.950
C4 C5 1.397(5)
C4 C11 1.487(5)
C5 C6 1.384(5)
C5 H5 0.950
C6 C7 1.374(5)
C6 H6 0.950
C8 C9 1.483(5)
C9 C10 1.511(5)
C9 H9A 0.990
C9 H9B 0.990
C11 C16 1.393(5)
C11 C12 1.407(5)
C12 C13 1.372(5)
C12 H12 0.950
C13 C14 1.378(6)
C13 H13 0.950
C14 C15 1.381(6)
C14 H14 0.950
C15 C16 1.378(5)
C15 H15 0.950
C16 H16 0.950
C17 H17A 0.980
C17 H17B 0.980
C17 H17C 0.980
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
O3 H1 O2 3_567 0.97(6) 1.66(6) 2.630(4) 174(6)
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
C17 S C1 C8 -105.6(4)
C17 S C1 C2 76.6(4)
C8 C1 C2 C7 -0.6(4)
S C1 C2 C7 177.6(3)
C8 C1 C2 C3 -178.1(3)
S C1 C2 C3 0.0(6)
C7 C2 C3 C4 0.9(4)
C1 C2 C3 C4 178.2(3)
C2 C3 C4 C5 0.8(5)
C2 C3 C4 C11 -177.1(3)
C3 C4 C5 C6 -0.9(5)
C11 C4 C5 C6 177.1(3)
C4 C5 C6 C7 -0.8(5)
C5 C6 C7 C2 2.7(5)
C5 C6 C7 O1 -178.8(3)
C3 C2 C7 C6 -2.8(5)
C1 C2 C7 C6 179.2(3)
C3 C2 C7 O1 178.5(3)
C1 C2 C7 O1 0.5(4)
C8 O1 C7 C6 -178.9(3)
C8 O1 C7 C2 -0.3(3)
C2 C1 C8 O1 0.4(4)
S C1 C8 O1 -177.8(2)
C2 C1 C8 C9 176.0(3)
S C1 C8 C9 -2.1(6)
C7 O1 C8 C1 -0.1(4)
C7 O1 C8 C9 -176.5(3)
C1 C8 C9 C10 120.0(4)
O1 C8 C9 C10 -64.4(4)
C8 C9 C10 O2 171.0(3)
C8 C9 C10 O3 -9.4(5)
C5 C4 C11 C16 136.8(4)
C3 C4 C11 C16 -45.3(5)
C5 C4 C11 C12 -42.0(5)
C3 C4 C11 C12 135.9(4)
C16 C11 C12 C13 1.5(5)
C4 C11 C12 C13 -179.7(3)
C11 C12 C13 C14 -2.4(6)
C12 C13 C14 C15 1.4(6)
C13 C14 C15 C16 0.5(6)
C14 C15 C16 C11 -1.4(5)
C12 C11 C16 C15 0.3(5)
C4 C11 C16 C15 -178.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123997
