##############################################################################
###                                                                        ###
###        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 # 
# article from which it was obtained.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-04-20
_journal_date_accepted     2010-05-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1296
_journal_page_last     o1296
_journal_paper_category     QO
_journal_coeditor_code     FL2302
_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     '+82-51-629-5596'
_publ_section_title
;
3-Ethylsulfinyl-2-(4-fluorophenyl)-5,6-methylenedioxy-1-benzofuran
;
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
;
_publ_section_synopsis     .
data_I
_chemical_name_systematic
;
3-Ethylsulfinyl-2-(4-fluorophenyl)-5,6-methylenedioxy-1-benzofuran
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H13 F O4 S'
_chemical_formula_sum     'C17 H13 F O4 S'
_chemical_formula_iupac     'C17 H13 F O4 S'
_chemical_formula_weight     332.33
_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     7.1081(9)
_cell_length_b     9.6310(10)
_cell_length_c     10.7080(10)
_cell_angle_alpha     93.201(2)
_cell_angle_beta     95.510(2)
_cell_angle_gamma     105.423(2)
_cell_volume     700.85(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4697
_cell_measurement_theta_min     2.20
_cell_measurement_theta_max     27.51
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.397
_exptl_crystal_size_mid     0.356
_exptl_crystal_size_min     0.276
_exptl_crystal_density_diffrn     1.575
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     344
_exptl_absorpt_coefficient_mu     0.262
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.6100
_exptl_absorpt_correction_T_max     0.7456
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     'graphite multilayer'
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     6872
_diffrn_reflns_av_R_equivalents     0.0208
_diffrn_reflns_av_sigmaI/netI     0.0270
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     27.52
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_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 > 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     3194
_reflns_number_gt     2955
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0376
_refine_ls_R_factor_gt     0.0350
_refine_ls_wR_factor_gt     0.0905
_refine_ls_wR_factor_ref     0.0926
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_restrained_S_all     1.025
_refine_ls_number_reflns     3194
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0462P)²+0.3499P] 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     0.346
_refine_diff_density_min     -0.338
_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'
    '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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_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 0.03741(5) 0.18237(3) 0.61999(3) 0.02096(11) Uani d . 1 . .
    F F 0.26284(17) 0.20685(12) 0.00053(8) 0.0408(3) Uani d . 1 . .
    O O1 0.28566(14) 0.56937(10) 0.50825(8) 0.0191(2) Uani d . 1 . .
    O O2 0.19966(18) 0.67938(11) 0.99731(9) 0.0294(2) Uani d . 1 . .
    O O3 0.33831(17) 0.87862(11) 0.89214(10) 0.0291(2) Uani d . 1 . .
    O O4 -0.10317(16) 0.18196(12) 0.71512(11) 0.0311(3) Uani d . 1 . .
    C C1 0.14785(19) 0.36484(14) 0.59545(12) 0.0173(3) Uani d . 1 . .
    C C2 0.18385(19) 0.48389(14) 0.69123(12) 0.0174(3) Uani d . 1 . .
    C C3 0.15149(19) 0.49635(14) 0.81894(12) 0.0192(3) Uani d . 1 . .
    H H3 0.0949 0.4172 0.8618 0.023 Uiso calc R 1 . .
    C C4 0.2106(2) 0.63511(15) 0.87430(12) 0.0204(3) Uani d . 1 . .
    C C5 0.2704(3) 0.83253(17) 1.00884(14) 0.0312(3) Uani d . 1 . .
    H H5A 0.3770 0.8637 1.0766 0.037 Uiso calc R 1 . .
    H H5B 0.1660 0.8749 1.0281 0.037 Uiso calc R 1 . .
    C C6 0.2941(2) 0.75576(15) 0.81127(13) 0.0209(3) Uani d . 1 . .
    C C7 0.3259(2) 0.74755(14) 0.68725(13) 0.0209(3) Uani d . 1 . .
    H H7 0.3804 0.8277 0.6449 0.025 Uiso calc R 1 . .
    C C8 0.26789(19) 0.60610(14) 0.63121(12) 0.0176(3) Uani d . 1 . .
    C C9 0.21082(19) 0.42130(14) 0.48737(12) 0.0176(3) Uani d . 1 . .
    C C10 0.22097(19) 0.36334(15) 0.35978(12) 0.0189(3) Uani d . 1 . .
    C C11 0.1684(2) 0.21477(15) 0.32548(13) 0.0234(3) Uani d . 1 . .
    H H11 0.1246 0.1505 0.3849 0.028 Uiso calc R 1 . .
    C C12 0.1803(2) 0.16148(17) 0.20450(14) 0.0273(3) Uani d . 1 . .
    H H12 0.1437 0.0626 0.1817 0.033 Uiso calc R 1 . .
    C C13 0.2479(2) 0.25910(18) 0.11899(13) 0.0265(3) Uani d . 1 . .
    C C14 0.3012(2) 0.40604(17) 0.14766(13) 0.0266(3) Uani d . 1 . .
    H H14 0.3462 0.4690 0.0875 0.032 Uiso calc R 1 . .
    C C15 0.2863(2) 0.45824(15) 0.26865(13) 0.0225(3) Uani d . 1 . .
    H H15 0.3201 0.5575 0.2896 0.027 Uiso calc R 1 . .
    C C16 0.2528(2) 0.14580(16) 0.70193(13) 0.0248(3) Uani d . 1 . .
    H H16A 0.3120 0.2226 0.7678 0.030 Uiso calc R 1 . .
    H H16B 0.2129 0.0560 0.7414 0.030 Uiso calc R 1 . .
    C C17 0.4039(2) 0.13464(17) 0.61352(15) 0.0276(3) Uani d . 1 . .
    H H17A 0.3473 0.0563 0.5501 0.041 Uiso calc R 1 . .
    H H17B 0.5163 0.1173 0.6604 0.041 Uiso calc R 1 . .
    H H17C 0.4435 0.2233 0.5741 0.041 Uiso calc R 1 . .
_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 O4 . 1.4930(10)
                    ?
    S C1 . 1.7700(10)
                    ?
    S C16 . 1.817(2) ?
    F C13 . 1.363(2) ?
    O1 C8 . 1.371(2) ?
    O1 C9 . 1.380(2) ?
    O2 C4 . 1.378(2) ?
    O2 C5 . 1.420(2) ?
    O3 C6 . 1.373(2) ?
    O3 C5 . 1.434(2) ?
    C1 C9 . 1.370(2) ?
    C1 C2 . 1.447(2) ?
    C2 C8 . 1.393(2) ?
    C2 C3 . 1.412(2) ?
    C3 C4 . 1.371(2) ?
    C3 H3 . 0.9300 ?
    C4 C6 . 1.399(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.370(2) ?
    C7 C8 . 1.396(2) ?
    C7 H7 . 0.9300 ?
    C9 C10 . 1.462(2) ?
    C10 C11 . 1.397(2) ?
    C10 C15 . 1.401(2) ?
    C11 C12 . 1.385(2) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.376(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.373(2) ?
    C14 C15 . 1.387(2) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.519(2) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 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
    O4 S C1 . . 107.47(6) ?
    O4 S C16 . . 106.53(7) ?
    C1 S C16 . . 97.30(7) ?
    C8 O1 C9 . . 107.08(10) ?
    C4 O2 C5 . . 106.39(11) ?
    C6 O3 C5 . . 105.79(11) ?
    C9 C1 C2 . . 107.48(11) ?
    C9 C1 S . . 128.49(10) ?
    C2 C1 S . . 124.02(10) ?
    C8 C2 C3 . . 120.58(12) ?
    C8 C2 C1 . . 104.70(11) ?
    C3 C2 C1 . . 134.72(12) ?
    C4 C3 C2 . . 114.24(12) ?
    C4 C3 H3 . . 122.9 ?
    C2 C3 H3 . . 122.9 ?
    C3 C4 O2 . . 127.02(13) ?
    C3 C4 C6 . . 123.81(13) ?
    O2 C4 C6 . . 109.17(12) ?
    O2 C5 O3 . . 108.58(11) ?
    O2 C5 H5A . . 110.0 ?
    O3 C5 H5A . . 110.0 ?
    O2 C5 H5B . . 110.0 ?
    O3 C5 H5B . . 110.0 ?
    H5A C5 H5B . . 108.4 ?
    C7 C6 O3 . . 126.72(13) ?
    C7 C6 C4 . . 123.41(13) ?
    O3 C6 C4 . . 109.87(12) ?
    C6 C7 C8 . . 112.81(12) ?
    C6 C7 H7 . . 123.6 ?
    C8 C7 H7 . . 123.6 ?
    O1 C8 C2 . . 110.85(11) ?
    O1 C8 C7 . . 124.01(12) ?
    C2 C8 C7 . . 125.15(12) ?
    C1 C9 O1 . . 109.89(11) ?
    C1 C9 C10 . . 135.89(12) ?
    O1 C9 C10 . . 114.21(11) ?
    C11 C10 C15 . . 118.46(12) ?
    C11 C10 C9 . . 121.86(12) ?
    C15 C10 C9 . . 119.68(12) ?
    C12 C11 C10 . . 121.19(13) ?
    C12 C11 H11 . . 119.4 ?
    C10 C11 H11 . . 119.4 ?
    C13 C12 C11 . . 118.09(14) ?
    C13 C12 H12 . . 121.0 ?
    C11 C12 H12 . . 121.0 ?
    F C13 C14 . . 118.71(13) ?
    F C13 C12 . . 118.20(14) ?
    C14 C13 C12 . . 123.09(13) ?
    C13 C14 C15 . . 118.31(14) ?
    C13 C14 H14 . . 120.8 ?
    C15 C14 H14 . . 120.8 ?
    C14 C15 C10 . . 120.84(13) ?
    C14 C15 H15 . . 119.6 ?
    C10 C15 H15 . . 119.6 ?
    C17 C16 S . . 111.94(10) ?
    C17 C16 H16A . . 109.2 ?
    S C16 H16A . . 109.2 ?
    C17 C16 H16B . . 109.2 ?
    S C16 H16B . . 109.2 ?
    H16A C16 H16B . . 107.9 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 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
    O4 S C1 C9 . . . . -147.47(12) ?
    C16 S C1 C9 . . . . 102.60(13) ?
    O4 S C1 C2 . . . . 31.24(13) ?
    C16 S C1 C2 . . . . -78.69(12) ?
    C9 C1 C2 C8 . . . . 0.08(14) ?
    S C1 C2 C8 . . . . -178.86(10) ?
    C9 C1 C2 C3 . . . . 179.64(14) ?
    S C1 C2 C3 . . . . 0.7(2) ?
    C8 C2 C3 C4 . . . . -0.45(19) ?
    C1 C2 C3 C4 . . . . -179.95(14) ?
    C2 C3 C4 O2 . . . . -179.10(13) ?
    C2 C3 C4 C6 . . . . 0.7(2) ?
    C5 O2 C4 C3 . . . . -177.56(14) ?
    C5 O2 C4 C6 . . . . 2.65(16) ?
    C4 O2 C5 O3 . . . . -4.39(17) ?
    C6 O3 C5 O2 . . . . 4.45(17) ?
    C5 O3 C6 C7 . . . . 177.68(14) ?
    C5 O3 C6 C4 . . . . -2.82(16) ?
    C3 C4 C6 C7 . . . . -0.1(2) ?
    O2 C4 C6 C7 . . . . 179.65(13) ?
    C3 C4 C6 O3 . . . . -179.66(13) ?
    O2 C4 C6 O3 . . . . 0.13(16) ?
    O3 C6 C7 C8 . . . . 178.87(13) ?
    C4 C6 C7 C8 . . . . -0.6(2) ?
    C9 O1 C8 C2 . . . . 0.47(14) ?
    C9 O1 C8 C7 . . . . -179.23(12) ?
    C3 C2 C8 O1 . . . . -179.97(11) ?
    C1 C2 C8 O1 . . . . -0.34(14) ?
    C3 C2 C8 C7 . . . . -0.3(2) ?
    C1 C2 C8 C7 . . . . 179.35(13) ?
    C6 C7 C8 O1 . . . . -179.57(12) ?
    C6 C7 C8 C2 . . . . 0.8(2) ?
    C2 C1 C9 O1 . . . . 0.20(15) ?
    S C1 C9 O1 . . . . 179.08(9) ?
    C2 C1 C9 C10 . . . . 178.68(14) ?
    S C1 C9 C10 . . . . -2.4(2) ?
    C8 O1 C9 C1 . . . . -0.41(14) ?
    C8 O1 C9 C10 . . . . -179.25(10) ?
    C1 C9 C10 C11 . . . . -4.3(2) ?
    O1 C9 C10 C11 . . . . 174.11(12) ?
    C1 C9 C10 C15 . . . . 176.13(15) ?
    O1 C9 C10 C15 . . . . -5.45(17) ?
    C15 C10 C11 C12 . . . . 0.1(2) ?
    C9 C10 C11 C12 . . . . -179.47(13) ?
    C10 C11 C12 C13 . . . . 0.8(2) ?
    C11 C12 C13 F . . . . 178.92(13) ?
    C11 C12 C13 C14 . . . . -0.9(2) ?
    F C13 C14 C15 . . . . -179.73(13) ?
    C12 C13 C14 C15 . . . . 0.1(2) ?
    C13 C14 C15 C10 . . . . 0.9(2) ?
    C11 C10 C15 C14 . . . . -0.9(2) ?
    C9 C10 C15 C14 . . . . 178.64(13) ?
    O4 S C16 C17 . . . . 176.72(10) ?
    C1 S C16 C17 . . . . -72.56(11) ?
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
    C12 H12 O4 2_556 0.93 2.62 3.380(2) 139.9
    C16 H16A F 1_556 0.97 2.56 3.2090(17) 124.7
    C17 H17B O4 1_655 0.96 2.61 3.469(2) 149.2
