#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223161.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_2223161
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(5-Methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetic acid
;
_journal_coeditor_code           NC2155
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2268
_journal_paper_doi               10.1107/S1600536809033765
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H12 O4 S'
_chemical_formula_moiety         'C12 H12 O4 S'
_chemical_formula_sum            'C12 H12 O4 S'
_chemical_formula_weight         252.28
_chemical_melting_point_gt       461
_chemical_melting_point_lt       462
_chemical_name_systematic
;
2-(5-Methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetic acid
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7670(10)
_cell_length_b                   16.248(2)
_cell_length_c                   18.733(2)
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.18
_cell_measurement_theta_min      2.73
_cell_volume                     2364.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      293(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 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  0.1099
_diffrn_reflns_av_sigmaI/netI    0.0897
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13669
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.8986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.450
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0521
_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)+(0.0469P)²+5.6706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                1461
_reflns_number_total             2690
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2155.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P_2ac_2ab
_cod_database_code               2223161
_cod_database_fobs_code          2223161
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'
'-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 S 0.11771(12) 0.71553(6) 0.38153(5) 0.0201(2) Uani d . 1 . .
O O1 0.2472(3) 0.49764(16) 0.45410(13) 0.0239(6) Uani d . 1 . .
O O2 0.6841(4) 0.67768(18) 0.46398(15) 0.0285(7) Uani d . 1 . .
H H2 0.761(7) 0.697(3) 0.437(3) 0.057(17) Uiso d . 1 . .
O O3 0.5236(4) 0.6591(2) 0.36700(15) 0.0429(9) Uani d . 1 . .
O O4 -0.0703(3) 0.73974(16) 0.38751(15) 0.0304(7) Uani d . 1 . .
C C1 0.1334(5) 0.6112(2) 0.40470(19) 0.0198(8) Uani d . 1 . .
C C2 0.0240(5) 0.5428(2) 0.38493(19) 0.0206(8) Uani d . 1 . .
C C3 -0.1287(5) 0.5323(2) 0.34684(19) 0.0232(8) Uani d . 1 . .
H H3 -0.1837 0.5773 0.3263 0.028 Uiso calc R 1 . .
C C4 -0.1973(5) 0.4540(2) 0.3400(2) 0.0262(9) Uani d . 1 . .
C C5 -0.1128(5) 0.3867(2) 0.3718(2) 0.0263(9) Uani d . 1 . .
H H5 -0.1594 0.3344 0.3664 0.032 Uiso calc R 1 . .
C C6 0.0363(5) 0.3956(2) 0.4107(2) 0.0238(9) Uani d . 1 . .
H H6 0.0910 0.3509 0.4317 0.029 Uiso calc R 1 . .
C C7 0.1005(5) 0.4747(2) 0.41678(19) 0.0201(8) Uani d . 1 . .
C C8 0.2619(5) 0.5814(2) 0.44641(18) 0.0203(8) Uani d . 1 . .
C C9 0.4120(5) 0.6207(2) 0.48186(19) 0.0228(9) Uani d . 1 . .
H H9A 0.4666 0.5806 0.5129 0.027 Uiso calc R 1 . .
H H9B 0.3713 0.6656 0.5115 0.027 Uiso calc R 1 . .
C C10 0.5441(5) 0.6535(2) 0.4304(2) 0.0218(8) Uani d . 1 . .
C C11 -0.3638(6) 0.4401(3) 0.2989(2) 0.0419(12) Uani d . 1 . .
H H11A -0.4395 0.4860 0.3062 0.063 Uiso calc R 1 . .
H H11B -0.4183 0.3907 0.3157 0.063 Uiso calc R 1 . .
H H11C -0.3386 0.4348 0.2490 0.063 Uiso calc R 1 . .
C C12 0.1561(6) 0.7075(3) 0.2878(2) 0.0349(11) Uani d . 1 . .
H H12A 0.0770 0.6687 0.2674 0.052 Uiso calc R 1 . .
H H12B 0.2719 0.6891 0.2798 0.052 Uiso calc R 1 . .
H H12C 0.1400 0.7603 0.2659 0.052 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 S C1 . . 107.41(17) ?
O4 S C12 . . 104.62(19) ?
C1 S C12 . . 99.26(19) ?
C8 O1 C7 . . 106.3(3) ?
C10 O2 H2 . . 114(3) ?
C8 C1 C2 . . 107.8(3) ?
C8 C1 S . . 122.6(3) ?
C2 C1 S . . 129.7(3) ?
C7 C2 C3 . . 119.1(3) ?
C7 C2 C1 . . 104.5(3) ?
C3 C2 C1 . . 136.4(4) ?
C4 C3 C2 . . 119.1(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 119.6(4) ?
C3 C4 C11 . . 120.7(4) ?
C5 C4 C11 . . 119.7(4) ?
C6 C5 C4 . . 122.3(4) ?
C6 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
C5 C6 C7 . . 116.5(4) ?
C5 C6 H6 . . 121.8 ?
C7 C6 H6 . . 121.8 ?
C6 C7 O1 . . 125.9(3) ?
C6 C7 C2 . . 123.3(4) ?
O1 C7 C2 . . 110.7(3) ?
C1 C8 O1 . . 110.7(3) ?
C1 C8 C9 . . 133.0(4) ?
O1 C8 C9 . . 116.3(3) ?
C8 C9 C10 . . 113.6(3) ?
C8 C9 H9A . . 108.8 ?
C10 C9 H9A . . 108.8 ?
C8 C9 H9B . . 108.8 ?
C10 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
O3 C10 O2 . . 124.0(4) ?
O3 C10 C9 . . 124.7(4) ?
O2 C10 C9 . . 111.3(3) ?
C4 C11 H11A . . 109.5 ?
C4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
S C12 H12A . . 109.5 ?
S C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
S C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 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 O4 . 1.516(3) ?
S C1 . 1.754(4) ?
S C12 . 1.786(4) ?
O1 C8 . 1.374(4) ?
O1 C7 . 1.388(4) ?
O2 C10 . 1.316(5) ?
O2 H2 . 0.85(5) ?
O3 C10 . 1.202(4) ?
C1 C8 . 1.356(5) ?
C1 C2 . 1.447(5) ?
C2 C7 . 1.390(5) ?
C2 C3 . 1.394(5) ?
C3 C4 . 1.385(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.408(5) ?
C4 C11 . 1.522(6) ?
C5 C6 . 1.375(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.383(5) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.486(5) ?
C9 C10 . 1.506(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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
C9 H9B O4 3_566 0.97 2.48 3.339(5) 147.5
O2 H2 O4 1_655 0.85(6) 1.74(6) 2.590(4) 175(5)
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
O4 S C1 C8 . . . . -138.0(3) ?
C12 S C1 C8 . . . . 113.4(3) ?
O4 S C1 C2 . . . . 42.9(4) ?
C12 S C1 C2 . . . . -65.7(4) ?
C8 C1 C2 C7 . . . . -0.9(4) ?
S C1 C2 C7 . . . . 178.3(3) ?
C8 C1 C2 C3 . . . . 176.6(4) ?
S C1 C2 C3 . . . . -4.2(7) ?
C7 C2 C3 C4 . . . . -1.9(5) ?
C1 C2 C3 C4 . . . . -179.1(4) ?
C2 C3 C4 C5 . . . . 0.4(6) ?
C2 C3 C4 C11 . . . . 179.9(4) ?
C3 C4 C5 C6 . . . . 0.8(6) ?
C11 C4 C5 C6 . . . . -178.8(4) ?
C4 C5 C6 C7 . . . . -0.3(6) ?
C5 C6 C7 O1 . . . . 179.1(3) ?
C5 C6 C7 C2 . . . . -1.2(6) ?
C8 O1 C7 C6 . . . . -179.5(4) ?
C8 O1 C7 C2 . . . . 0.8(4) ?
C3 C2 C7 C6 . . . . 2.4(6) ?
C1 C2 C7 C6 . . . . -179.6(3) ?
C3 C2 C7 O1 . . . . -177.9(3) ?
C1 C2 C7 O1 . . . . 0.1(4) ?
C2 C1 C8 O1 . . . . 1.5(4) ?
S C1 C8 O1 . . . . -177.8(2) ?
C2 C1 C8 C9 . . . . 179.3(4) ?
S C1 C8 C9 . . . . 0.0(6) ?
C7 O1 C8 C1 . . . . -1.4(4) ?
C7 O1 C8 C9 . . . . -179.6(3) ?
C1 C8 C9 C10 . . . . -66.5(5) ?
O1 C8 C9 C10 . . . . 111.2(4) ?
C8 C9 C10 O3 . . . . 10.1(6) ?
C8 C9 C10 O2 . . . . -171.7(3) ?
