##############################################################################
###                                                                        ###
###        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     2009-03-30
_journal_date_accepted     2009-04-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o998
_journal_page_last     o998
_journal_paper_category     QO
_journal_coeditor_code     ZL2191
_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     '+82-51-629-5583'
_publ_contact_author_phone     '+82-51-629-5956'
_publ_section_title
;
2-(3-Methylsulfanyl-5-propyl-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-(3-Methylsulfanyl-5-propyl-1-benzofuran-2-yl)acetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H16 O3 S'
_chemical_formula_sum     'C14 H16 O3 S'
_chemical_formula_iupac     'C14 H16 O3 S'
_chemical_formula_weight     264.33
_chemical_melting_point     ?
_symmetry_cell_setting     'Triclinic'
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.1727(6)
_cell_length_b     8.1730(10)
_cell_length_c     16.614(2)
_cell_angle_alpha     94.321(2)
_cell_angle_beta     95.831(2)
_cell_angle_gamma     91.110(2)
_cell_volume     696.50(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1161
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     22.08
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.260
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.230
_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     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_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     3658
_diffrn_reflns_av_R_equivalents     0.0494
_diffrn_reflns_av_sigmaI/netI     0.0724
_diffrn_reflns_theta_min     2.50
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.974
_diffrn_measured_fraction_theta_full     0.974
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_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 > 2sigma(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     2389
_reflns_number_gt     1425
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1062
_refine_ls_R_factor_gt     0.0591
_refine_ls_wR_factor_gt     0.1304
_refine_ls_wR_factor_ref     0.1506
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.061
_refine_ls_number_reflns     2389
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0531P)²+0.2044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.207
_refine_diff_density_min     -0.239
_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 -0.09603(19) 0.20796(12) 0.21468(7) 0.0768(4) Uani d . 1 . .
    O O1 0.1105(4) 0.5482(3) 0.39156(13) 0.0636(6) Uani d . 1 . .
    O O2 0.1260(5) 0.1733(3) 0.45463(16) 0.0851(9) Uani d . 1 . .
    H H2O 0.1607 0.0891 0.4769 0.128 Uiso calc R 1 . .
    O O3 -0.2757(4) 0.0916(3) 0.46894(16) 0.0785(8) Uani d . 1 . .
    C C1 0.0362(6) 0.3712(4) 0.2809(2) 0.0520(8) Uani d . 1 . .
    C C2 0.2351(6) 0.4892(4) 0.26600(19) 0.0516(8) Uani d . 1 . .
    C C3 0.3818(6) 0.5128(4) 0.2021(2) 0.0591(9) Uani d . 1 . .
    H H3 0.3590 0.4425 0.1552 0.071 Uiso calc R 1 . .
    C C4 0.5633(6) 0.6423(4) 0.2089(2) 0.0627(10) Uani d . 1 . .
    C C5 0.5902(7) 0.7445(4) 0.2808(3) 0.0711(10) Uani d . 1 . .
    H H5 0.7094 0.8322 0.2852 0.085 Uiso calc R 1 . .
    C C6 0.4507(7) 0.7226(4) 0.3450(2) 0.0708(10) Uani d . 1 . .
    H H6 0.4752 0.7910 0.3926 0.085 Uiso calc R 1 . .
    C C7 0.2718(6) 0.5937(4) 0.3353(2) 0.0556(8) Uani d . 1 . .
    C C8 -0.0298(6) 0.4115(4) 0.3551(2) 0.0546(8) Uani d . 1 . .
    C C9 0.7208(8) 0.6706(5) 0.1400(2) 0.0824(12) Uani d . 1 . .
    H H9A 0.8818 0.7278 0.1618 0.099 Uiso calc R 1 . .
    H H9B 0.7653 0.5649 0.1153 0.099 Uiso calc R 1 . .
    C C10 0.5895(10) 0.7662(7) 0.0762(3) 0.1197(18) Uani d . 1 . .
    H H10A 0.5433 0.8713 0.1011 0.144 Uiso calc R 1 . .
    H H10B 0.4293 0.7084 0.0542 0.144 Uiso calc R 1 . .
    C C11 0.7458(12) 0.7960(8) 0.0082(3) 0.146(2) Uani d . 1 . .
    H H11A 0.8735 0.8817 0.0253 0.219 Uiso calc R 1 . .
    H H11B 0.6335 0.8284 -0.0371 0.219 Uiso calc R 1 . .
    H H11C 0.8314 0.6972 -0.0075 0.219 Uiso calc R 1 . .
    C C12 -0.2179(6) 0.3359(4) 0.4048(2) 0.0619(9) Uani d . 1 . .
    H H12A -0.3761 0.3045 0.3702 0.074 Uiso calc R 1 . .
    H H12B -0.2620 0.4176 0.4463 0.074 Uiso calc R 1 . .
    C C13 -0.1180(6) 0.1878(4) 0.44510(19) 0.0545(8) Uani d . 1 . .
    C C14 0.1689(8) 0.0703(5) 0.2223(3) 0.1078(16) Uani d . 1 . .
    H H14A 0.3270 0.1278 0.2146 0.162 Uiso calc R 1 . .
    H H14B 0.1370 -0.0192 0.1813 0.162 Uiso calc R 1 . .
    H H14C 0.1847 0.0284 0.2749 0.162 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 0.0644(7) 0.0620(6) 0.1009(8) -0.0190(5) 0.0062(5) -0.0057(5)
    O1 0.0738(16) 0.0557(14) 0.0620(15) -0.0043(12) 0.0080(12) 0.0099(11)
    O2 0.0554(17) 0.0877(18) 0.120(2) 0.0049(13) 0.0086(14) 0.0595(16)
    O3 0.0556(15) 0.0722(16) 0.113(2) -0.0081(12) 0.0101(13) 0.0463(15)
    C1 0.0513(19) 0.0419(17) 0.063(2) -0.0047(14) 0.0008(16) 0.0153(15)
    C2 0.055(2) 0.0433(17) 0.057(2) -0.0015(15) -0.0005(16) 0.0152(16)
    C3 0.062(2) 0.0521(19) 0.064(2) -0.0027(16) 0.0043(17) 0.0104(16)
    C4 0.060(2) 0.054(2) 0.075(3) -0.0056(17) 0.0014(18) 0.0213(19)
    C5 0.070(2) 0.049(2) 0.095(3) -0.0111(18) 0.004(2) 0.017(2)
    C6 0.088(3) 0.0472(19) 0.075(3) -0.0126(19) 0.003(2) 0.0014(18)
    C7 0.062(2) 0.0447(17) 0.061(2) -0.0007(15) 0.0056(17) 0.0111(17)
    C8 0.055(2) 0.0487(18) 0.061(2) -0.0023(15) 0.0006(16) 0.0183(16)
    C9 0.078(3) 0.079(3) 0.095(3) -0.012(2) 0.016(2) 0.030(2)
    C10 0.135(4) 0.134(4) 0.105(4) 0.020(3) 0.041(3) 0.056(3)
    C11 0.190(6) 0.151(5) 0.107(4) -0.005(5) 0.046(4) 0.042(4)
    C12 0.055(2) 0.060(2) 0.075(2) 0.0041(16) 0.0076(17) 0.0286(18)
    C13 0.045(2) 0.058(2) 0.063(2) 0.0015(16) 0.0080(16) 0.0191(16)
    C14 0.080(3) 0.059(2) 0.183(5) -0.007(2) 0.031(3) -0.020(3)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 . 1.746(3) ?
    S C14 . 1.791(4) ?
    O1 C7 . 1.381(4) ?
    O1 C8 . 1.385(4) ?
    O2 C13 . 1.265(3) ?
    O2 H2O . 0.8200 ?
    O3 C13 . 1.237(4) ?
    C1 C8 . 1.332(4) ?
    C1 C2 . 1.448(4) ?
    C2 C7 . 1.376(4) ?
    C2 C3 . 1.388(4) ?
    C3 C4 . 1.392(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.399(5) ?
    C4 C9 . 1.499(5) ?
    C5 C6 . 1.368(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.377(4) ?
    C6 H6 . 0.9300 ?
    C8 C12 . 1.493(4) ?
    C9 C10 . 1.482(5) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.487(6) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C13 . 1.501(4) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
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 C14 . . 99.71(17) ?
    C7 O1 C8 . . 105.5(2) ?
    C13 O2 H2O . . 109.5 ?
    C8 C1 C2 . . 106.9(3) ?
    C8 C1 S . . 126.0(2) ?
    C2 C1 S . . 127.1(3) ?
    C7 C2 C3 . . 119.6(3) ?
    C7 C2 C1 . . 105.4(3) ?
    C3 C2 C1 . . 135.0(3) ?
    C2 C3 C4 . . 119.6(3) ?
    C2 C3 H3 . . 120.2 ?
    C4 C3 H3 . . 120.2 ?
    C3 C4 C5 . . 118.0(3) ?
    C3 C4 C9 . . 120.2(3) ?
    C5 C4 C9 . . 121.8(3) ?
    C6 C5 C4 . . 123.6(3) ?
    C6 C5 H5 . . 118.2 ?
    C4 C5 H5 . . 118.2 ?
    C5 C6 C7 . . 116.4(3) ?
    C5 C6 H6 . . 121.8 ?
    C7 C6 H6 . . 121.8 ?
    C2 C7 C6 . . 122.9(3) ?
    C2 C7 O1 . . 110.5(3) ?
    C6 C7 O1 . . 126.6(3) ?
    C1 C8 O1 . . 111.7(3) ?
    C1 C8 C12 . . 132.2(3) ?
    O1 C8 C12 . . 116.1(3) ?
    C10 C9 C4 . . 114.6(3) ?
    C10 C9 H9A . . 108.6 ?
    C4 C9 H9A . . 108.6 ?
    C10 C9 H9B . . 108.6 ?
    C4 C9 H9B . . 108.6 ?
    H9A C9 H9B . . 107.6 ?
    C9 C10 C11 . . 114.8(4) ?
    C9 C10 H10A . . 108.6 ?
    C11 C10 H10A . . 108.6 ?
    C9 C10 H10B . . 108.6 ?
    C11 C10 H10B . . 108.6 ?
    H10A C10 H10B . . 107.5 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C8 C12 C13 . . 114.0(3) ?
    C8 C12 H12A . . 108.8 ?
    C13 C12 H12A . . 108.8 ?
    C8 C12 H12B . . 108.8 ?
    C13 C12 H12B . . 108.8 ?
    H12A C12 H12B . . 107.7 ?
    O3 C13 O2 . . 124.3(3) ?
    O3 C13 C12 . . 118.8(3) ?
    O2 C13 C12 . . 116.9(3) ?
    S C14 H14A . . 109.5 ?
    S C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    S C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 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
    C14 S C1 C8 . . . . -106.1(3) ?
    C14 S C1 C2 . . . . 74.5(3) ?
    C8 C1 C2 C7 . . . . 0.0(3) ?
    S C1 C2 C7 . . . . 179.5(2) ?
    C8 C1 C2 C3 . . . . 179.1(3) ?
    S C1 C2 C3 . . . . -1.4(5) ?
    C7 C2 C3 C4 . . . . -0.3(5) ?
    C1 C2 C3 C4 . . . . -179.4(3) ?
    C2 C3 C4 C5 . . . . 0.0(5) ?
    C2 C3 C4 C9 . . . . -179.2(3) ?
    C3 C4 C5 C6 . . . . 0.9(5) ?
    C9 C4 C5 C6 . . . . -179.8(3) ?
    C4 C5 C6 C7 . . . . -1.5(5) ?
    C3 C2 C7 C6 . . . . -0.3(5) ?
    C1 C2 C7 C6 . . . . 179.0(3) ?
    C3 C2 C7 O1 . . . . -179.2(3) ?
    C1 C2 C7 O1 . . . . 0.1(3) ?
    C5 C6 C7 C2 . . . . 1.1(5) ?
    C5 C6 C7 O1 . . . . 179.9(3) ?
    C8 O1 C7 C2 . . . . -0.2(3) ?
    C8 O1 C7 C6 . . . . -179.0(3) ?
    C2 C1 C8 O1 . . . . -0.1(3) ?
    S C1 C8 O1 . . . . -179.6(2) ?
    C2 C1 C8 C12 . . . . -178.7(3) ?
    S C1 C8 C12 . . . . 1.8(5) ?
    C7 O1 C8 C1 . . . . 0.2(3) ?
    C7 O1 C8 C12 . . . . 179.0(3) ?
    C3 C4 C9 C10 . . . . 83.8(5) ?
    C5 C4 C9 C10 . . . . -95.4(5) ?
    C4 C9 C10 C11 . . . . 179.4(5) ?
    C1 C8 C12 C13 . . . . 79.2(4) ?
    O1 C8 C12 C13 . . . . -99.3(3) ?
    C8 C12 C13 O3 . . . . -160.9(3) ?
    C8 C12 C13 O2 . . . . 21.3(5) ?
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
    O2 H2O O3 2_556 0.82 1.86 2.679(3) 173.7
    C12 H12A Cg 1_455 0.97 3.04 3.770(3) 133.0
