##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-07-18
_journal_date_accepted     2008-07-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o1688
_journal_page_last     o1688
_journal_paper_category     QO
_journal_coeditor_code     HB2769
_publ_contact_author_name     'Prof. Uk Lee'
_publ_contact_author_address
;
Department of Chemistry,
Pukyong National University,
599-1 Daeyeon 3-dong, Nam-gu,
Busan 608-737, Republic of Korea
;
_publ_contact_author_email     uklee@pknu.ac.kr
_publ_contact_author_fax     '+82-51-628-8147'
_publ_contact_author_phone     '+82-51-620-6374'
_publ_section_title
;
2-(6,7-Dimethyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Choi, Hong Dae'
;
Department of Chemistry,
Dongeui University,
San 24 Kaya-dong, Busanjin-gu,
Busan 614-714, Republic of Korea
;
    'Seo, Pil Ja'
;
Department of Chemistry,
Dongeui University,
San 24 Kaya-dong, Busanjin-gu,
Busan 614-714, Republic of Korea
;
    'Son, Byeng Wha'
;
Department of Chemistry,
Pukyong National University,
599-1 Daeyeon 3-dong, Nam-gu,
Busan 608-737, Republic of Korea
;
    'Lee, Uk'
;
Department of Chemistry,
Pukyong National University,
599-1 Daeyeon 3-dong, Nam-gu,
Busan 608-737, Republic of Korea
;
data_I
_chemical_name_systematic
;
2-(6,7-Dimethyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H14 O3 S'
_chemical_formula_sum     'C13 H14 O3 S'
_chemical_formula_iupac     'C13 H14 O3 S'
_chemical_formula_weight     250.30
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P_2ybc'
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'
_cell_length_a     18.050(2)
_cell_length_b     4.9422(5)
_cell_length_c     13.8850(10)
_cell_angle_alpha     90.00
_cell_angle_beta     104.451(2)
_cell_angle_gamma     90.00
_cell_volume     1199.4(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4188
_cell_measurement_theta_min     2.96
_cell_measurement_theta_max     28.27
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.386
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.263
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     6673
_diffrn_reflns_av_R_equivalents     0.0346
_diffrn_reflns_av_sigmaI/netI     0.0296
_diffrn_reflns_theta_min     1.16
_diffrn_reflns_theta_max     26.98
_diffrn_reflns_theta_full     26.98
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2595
_reflns_number_gt     2269
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0463
_refine_ls_R_factor_gt     0.0382
_refine_ls_wR_factor_gt     0.1056
_refine_ls_wR_factor_ref     0.1191
_refine_ls_goodness_of_fit_ref     1.169
_refine_ls_restrained_S_all     1.169
_refine_ls_number_reflns     2595
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0641P)²+0.395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'difmap (O-H) and geom (C-H)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.419
_refine_diff_density_min     -0.247
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                      'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.36076(2) 0.71244(9) 0.66542(3) 0.02429(16) Uani d . 1 . .
    O O1 0.22123(6) 0.3898(3) 0.81259(8) 0.0204(3) Uani d . 1 . .
    O O2 0.40090(8) 0.3577(3) 0.94500(11) 0.0324(4) Uani d . 1 . .
    H H2O 0.4453(16) 0.310(6) 0.970(2) 0.049(8) Uiso d . 1 . .
    O O3 0.45128(7) 0.7710(3) 0.96729(10) 0.0284(3) Uani d . 1 . .
    C C1 0.29079(9) 0.5385(3) 0.70833(12) 0.0189(4) Uani d . 1 . .
    C C2 0.23677(9) 0.3392(4) 0.65574(12) 0.0189(4) Uani d . 1 . .
    C C3 0.21948(10) 0.2279(4) 0.56064(13) 0.0235(4) Uani d . 1 . .
    H H3 0.2463 0.2811 0.5129 0.028 Uiso calc R 1 . .
    C C4 0.16167(10) 0.0365(4) 0.53846(13) 0.0252(4) Uani d . 1 . .
    H H4 0.1490 -0.0418 0.4739 0.030 Uiso calc R 1 . .
    C C5 0.12090(10) -0.0469(4) 0.60716(13) 0.0229(4) Uani d . 1 . .
    C C6 0.13800(9) 0.0629(4) 0.70363(13) 0.0209(4) Uani d . 1 . .
    C C7 0.19588(9) 0.2551(3) 0.72277(12) 0.0187(4) Uani d . 1 . .
    C C8 0.27891(9) 0.5601(4) 0.80010(12) 0.0192(4) Uani d . 1 . .
    C C9 0.05928(11) -0.2584(4) 0.57689(16) 0.0311(5) Uani d . 1 . .
    H H9A 0.0729 -0.4181 0.6195 0.047 Uiso calc R 1 . .
    H H9B 0.0543 -0.3097 0.5074 0.047 Uiso calc R 1 . .
    H H9C 0.0105 -0.1849 0.5841 0.047 Uiso calc R 1 . .
    C C10 0.09738(11) -0.0203(4) 0.78102(15) 0.0316(5) Uani d . 1 . .
    H H10A 0.1197 0.0752 0.8434 0.047 Uiso calc R 1 . .
    H H10B 0.1029 -0.2159 0.7921 0.047 Uiso calc R 1 . .
    H H10C 0.0430 0.0256 0.7581 0.047 Uiso calc R 1 . .
    C C11 0.31794(10) 0.7259(4) 0.88784(13) 0.0221(4) Uani d . 1 . .
    H H11A 0.2865 0.7255 0.9370 0.026 Uiso calc R 1 . .
    H H11B 0.3218 0.9152 0.8663 0.026 Uiso calc R 1 . .
    C C12 0.39713(10) 0.6221(4) 0.93705(12) 0.0197(4) Uani d . 1 . .
    C C13 0.43420(11) 0.4564(4) 0.68607(16) 0.0315(4) Uani d . 1 . .
    H H13A 0.4529 0.4230 0.7576 0.047 Uiso calc R 1 . .
    H H13B 0.4766 0.5183 0.6592 0.047 Uiso calc R 1 . .
    H H13C 0.4130 0.2887 0.6526 0.047 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S 0.0226(3) 0.0218(3) 0.0288(3) -0.00298(17) 0.00704(18) 0.00404(18)
    O1 0.0180(6) 0.0248(7) 0.0181(6) -0.0020(5) 0.0039(4) -0.0033(5)
    O2 0.0245(7) 0.0204(7) 0.0432(8) 0.0008(5) -0.0081(6) 0.0012(6)
    O3 0.0204(6) 0.0229(7) 0.0377(7) -0.0021(5) -0.0005(5) -0.0019(6)
    C1 0.0161(8) 0.0183(8) 0.0211(8) 0.0002(6) 0.0021(6) 0.0017(7)
    C2 0.0157(8) 0.0201(9) 0.0192(8) 0.0011(6) 0.0009(6) 0.0004(7)
    C3 0.0239(9) 0.0265(10) 0.0196(8) -0.0009(7) 0.0041(7) -0.0021(7)
    C4 0.0266(9) 0.0251(10) 0.0206(8) -0.0013(7) -0.0002(7) -0.0060(7)
    C5 0.0179(8) 0.0190(9) 0.0277(9) 0.0006(6) -0.0019(7) -0.0017(7)
    C6 0.0165(8) 0.0190(9) 0.0258(9) 0.0008(6) 0.0027(6) 0.0019(7)
    C7 0.0171(8) 0.0195(9) 0.0178(8) 0.0019(6) 0.0009(6) -0.0014(7)
    C8 0.0153(8) 0.0186(9) 0.0218(8) 0.0012(6) 0.0011(6) -0.0010(7)
    C9 0.0256(10) 0.0243(10) 0.0384(11) -0.0052(7) -0.0012(8) -0.0028(8)
    C10 0.0259(10) 0.0350(11) 0.0354(10) -0.0061(8) 0.0106(8) 0.0015(9)
    C11 0.0206(9) 0.0203(9) 0.0221(8) 0.0014(7) -0.0006(7) -0.0047(7)
    C12 0.0218(9) 0.0209(9) 0.0156(7) -0.0002(7) 0.0032(6) -0.0027(7)
    C13 0.0258(10) 0.0310(11) 0.0402(11) 0.0012(8) 0.0127(8) 0.0018(9)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 . 1.7506(17) ?
    S C13 . 1.803(2) ?
    O1 C8 . 1.383(2) ?
    O1 C7 . 1.387(2) ?
    O2 C12 . 1.312(2) ?
    O2 H2O . 0.83(3) ?
    O3 C12 . 1.212(2) ?
    C1 C8 . 1.348(2) ?
    C1 C2 . 1.449(2) ?
    C2 C7 . 1.388(2) ?
    C2 C3 . 1.392(2) ?
    C3 C4 . 1.385(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.404(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.407(2) ?
    C5 C9 . 1.507(2) ?
    C6 C7 . 1.388(2) ?
    C6 C10 . 1.502(2) ?
    C8 C11 . 1.491(2) ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C12 . 1.512(2) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
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 C13 . . 99.52(9) ?
    C8 O1 C7 . . 105.60(10)
                          ?
    C12 O2 H2O . . 110(2) ?
    C8 C1 C2 . . 106.5(2) ?
    C8 C1 S . . 125.50(10)
                         ?
    C2 C1 S . . 127.90(10)
                         ?
    C7 C2 C3 . . 119.2(2) ?
    C7 C2 C1 . . 105.60(10)
                          ?
    C3 C2 C1 . . 135.3(2) ?
    C4 C3 C2 . . 117.3(2) ?
    C4 C3 H3 . . 121.3 ?
    C2 C3 H3 . . 121.3 ?
    C3 C4 C5 . . 122.9(2) ?
    C3 C4 H4 . . 118.6 ?
    C5 C4 H4 . . 118.6 ?
    C4 C5 C6 . . 120.4(2) ?
    C4 C5 C9 . . 119.3(2) ?
    C6 C5 C9 . . 120.3(2) ?
    C7 C6 C5 . . 115.0(2) ?
    C7 C6 C10 . . 121.9(2) ?
    C5 C6 C10 . . 123.1(2) ?
    O1 C7 C6 . . 124.4(2) ?
    O1 C7 C2 . . 110.40(10)
                          ?
    C6 C7 C2 . . 125.3(2) ?
    C1 C8 O1 . . 111.9(2) ?
    C1 C8 C11 . . 131.4(2) ?
    O1 C8 C11 . . 116.7(2) ?
    C5 C9 H9A . . 109.5 ?
    C5 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C5 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C6 C10 H10A . . 109.5 ?
    C6 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C6 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C8 C11 C12 . . 112.50(10)
                            ?
    C8 C11 H11A . . 109.1 ?
    C12 C11 H11A . . 109.1 ?
    C8 C11 H11B . . 109.1 ?
    C12 C11 H11B . . 109.1 ?
    H11A C11 H11B . . 107.8 ?
    O3 C12 O2 . . 123.7(2) ?
    O3 C12 C11 . . 122.7(2) ?
    O2 C12 C11 . . 113.5(2) ?
    S C13 H13A . . 109.5 ?
    S C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    S C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
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
    C13 S C1 C8 . . . . 96.66(17) ?
    C13 S C1 C2 . . . . -80.90(17) ?
    C8 C1 C2 C7 . . . . -0.11(19) ?
    S C1 C2 C7 . . . . 177.82(13) ?
    C8 C1 C2 C3 . . . . 179.6(2) ?
    S C1 C2 C3 . . . . -2.5(3) ?
    C7 C2 C3 C4 . . . . -0.1(3) ?
    C1 C2 C3 C4 . . . . -179.80(19) ?
    C2 C3 C4 C5 . . . . 0.0(3) ?
    C3 C4 C5 C6 . . . . -0.3(3) ?
    C3 C4 C5 C9 . . . . -179.47(17) ?
    C4 C5 C6 C7 . . . . 0.7(2) ?
    C9 C5 C6 C7 . . . . 179.84(16) ?
    C4 C5 C6 C10 . . . . -179.11(17) ?
    C9 C5 C6 C10 . . . . 0.1(3) ?
    C8 O1 C7 C6 . . . . 179.73(16) ?
    C8 O1 C7 C2 . . . . 0.01(18) ?
    C5 C6 C7 O1 . . . . 179.48(15) ?
    C10 C6 C7 O1 . . . . -0.7(3) ?
    C5 C6 C7 C2 . . . . -0.8(3) ?
    C10 C6 C7 C2 . . . . 178.93(17) ?
    C3 C2 C7 O1 . . . . -179.69(15) ?
    C1 C2 C7 O1 . . . . 0.06(18) ?
    C3 C2 C7 C6 . . . . 0.6(3) ?
    C1 C2 C7 C6 . . . . -179.65(16) ?
    C2 C1 C8 O1 . . . . 0.13(19) ?
    S C1 C8 O1 . . . . -177.87(12) ?
    C2 C1 C8 C11 . . . . 178.24(17) ?
    S C1 C8 C11 . . . . 0.2(3) ?
    C7 O1 C8 C1 . . . . -0.09(18) ?
    C7 O1 C8 C11 . . . . -178.51(14) ?
    C1 C8 C11 C12 . . . . -72.5(2) ?
    O1 C8 C11 C12 . . . . 105.56(17) ?
    C8 C11 C12 O3 . . . . 138.89(18) ?
    C8 C11 C12 O2 . . . . -42.1(2) ?
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 H9A Cg 1_545 0.98 2.86 3.617(2) 135
    O2 H2O O3 3_667 0.83(3) 1.89(3) 2.717(2) 175(3)
