##############################################################################
###                                                                        ###
###        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     2008-06-28
_journal_date_accepted     2008-07-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1477
_journal_page_last     o1477
_journal_paper_category     QO
_journal_coeditor_code     GK2156
_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-Methyl-3-phenylsulfinyl-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
;
data_I
_chemical_name_systematic
;
2-Methyl-3-phenylsulfinyl-1-benzofuran
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H12 O2 S'
_chemical_formula_sum     'C15 H12 O2 S'
_chemical_formula_iupac     'C15 H12 O2 S'
_chemical_formula_weight     256.31
_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     12.946(2)
_cell_length_b     9.4660(10)
_cell_length_c     10.2940(10)
_cell_angle_alpha     90.00
_cell_angle_beta     103.887(2)
_cell_angle_gamma     90.00
_cell_volume     1224.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5415
_cell_measurement_theta_min     2.69
_cell_measurement_theta_max     28.19
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.390
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.254
_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     6763
_diffrn_reflns_av_R_equivalents     0.0376
_diffrn_reflns_av_sigmaI/netI     0.0254
_diffrn_reflns_theta_min     1.62
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     2405
_reflns_number_gt     2192
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0417
_refine_ls_R_factor_gt     0.0385
_refine_ls_wR_factor_gt     0.0982
_refine_ls_wR_factor_ref     0.1022
_refine_ls_goodness_of_fit_ref     1.107
_refine_ls_restrained_S_all     1.107
_refine_ls_number_reflns     2405
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0544P)²+0.4838P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.249
_refine_diff_density_min     -0.516
_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 0.21943(3) 0.67373(4) 0.24290(4) 0.02584(14) Uani d . 1 . .
    O O1 0.42892(9) 0.63644(14) 0.58590(11) 0.0324(3) Uani d . 1 . .
    O O2 0.23114(10) 0.57743(14) 0.13205(11) 0.0372(3) Uani d . 1 . .
    C C1 0.30363(12) 0.61722(17) 0.39339(15) 0.0239(3) Uani d . 1 . .
    C C2 0.31131(11) 0.48127(17) 0.45930(14) 0.0244(3) Uani d . 1 . .
    C C3 0.26168(13) 0.35014(17) 0.43207(16) 0.0287(3) Uani d . 1 . .
    H H3 0.2089 0.3341 0.3517 0.034 Uiso calc R 1 . .
    C C4 0.29212(14) 0.24396(19) 0.52657(18) 0.0353(4) Uani d . 1 . .
    H H4 0.2590 0.1540 0.5107 0.042 Uiso calc R 1 . .
    C C5 0.37026(15) 0.2664(2) 0.64428(18) 0.0394(4) Uani d . 1 . .
    H H5 0.3885 0.1916 0.7071 0.047 Uiso calc R 1 . .
    C C6 0.42179(14) 0.3951(2) 0.67166(17) 0.0379(4) Uani d . 1 . .
    H H6 0.4760 0.4104 0.7507 0.045 Uiso calc R 1 . .
    C C7 0.38969(12) 0.49963(19) 0.57741(15) 0.0291(4) Uani d . 1 . .
    C C8 0.37502(12) 0.70491(18) 0.47218(15) 0.0277(3) Uani d . 1 . .
    C C9 0.09419(12) 0.62970(16) 0.27953(14) 0.0235(3) Uani d . 1 . .
    C C10 0.02207(13) 0.55290(18) 0.18570(16) 0.0317(4) Uani d . 1 . .
    H H10 0.0412 0.5168 0.1086 0.038 Uiso calc R 1 . .
    C C11 -0.07920(14) 0.5289(2) 0.20534(19) 0.0374(4) Uani d . 1 . .
    H H11 -0.1296 0.4765 0.1412 0.045 Uiso calc R 1 . .
    C C12 -0.10656(13) 0.58118(19) 0.31772(19) 0.0362(4) Uani d . 1 . .
    H H12 -0.1759 0.5651 0.3306 0.043 Uiso calc R 1 . .
    C C13 -0.03302(14) 0.65707(19) 0.41178(18) 0.0359(4) Uani d . 1 . .
    H H13 -0.0519 0.6921 0.4894 0.043 Uiso calc R 1 . .
    C C14 0.06790(13) 0.68229(17) 0.39348(16) 0.0295(4) Uani d . 1 . .
    H H14 0.1183 0.7347 0.4578 0.035 Uiso calc R 1 . .
    C C15 0.40351(14) 0.85446(19) 0.45966(19) 0.0364(4) Uani d . 1 . .
    H H15A 0.3707 0.8880 0.3691 0.055 Uiso calc R 1 . .
    H H15B 0.4810 0.8633 0.4766 0.055 Uiso calc R 1 . .
    H H15C 0.3778 0.9113 0.5250 0.055 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 0.0309(2) 0.0267(2) 0.0210(2) -0.00105(15) 0.00834(16) 0.00241(14)
    O1 0.0259(6) 0.0415(7) 0.0281(6) -0.0028(5) 0.0033(5) -0.0067(5)
    O2 0.0444(7) 0.0478(8) 0.0227(6) 0.0018(6) 0.0143(5) -0.0049(5)
    C1 0.0239(7) 0.0266(8) 0.0227(7) -0.0017(6) 0.0083(6) -0.0008(6)
    C2 0.0223(7) 0.0298(8) 0.0225(7) 0.0032(6) 0.0082(6) 0.0006(6)
    C3 0.0291(8) 0.0281(8) 0.0300(8) 0.0009(6) 0.0094(6) -0.0002(6)
    C4 0.0382(9) 0.0290(9) 0.0431(9) 0.0080(7) 0.0184(8) 0.0058(7)
    C5 0.0419(10) 0.0439(11) 0.0363(9) 0.0196(8) 0.0171(8) 0.0148(8)
    C6 0.0333(9) 0.0535(11) 0.0260(8) 0.0157(8) 0.0056(7) 0.0036(8)
    C7 0.0244(7) 0.0381(9) 0.0260(8) 0.0029(7) 0.0082(6) -0.0034(7)
    C8 0.0234(7) 0.0340(9) 0.0278(8) -0.0023(6) 0.0103(6) -0.0051(7)
    C9 0.0270(8) 0.0215(7) 0.0211(7) 0.0020(6) 0.0041(6) 0.0024(6)
    C10 0.0346(8) 0.0323(9) 0.0257(8) 0.0012(7) 0.0026(6) -0.0051(7)
    C11 0.0301(9) 0.0344(9) 0.0422(9) -0.0027(7) -0.0023(7) -0.0063(8)
    C12 0.0264(8) 0.0342(9) 0.0480(10) 0.0003(7) 0.0086(7) 0.0015(8)
    C13 0.0353(9) 0.0392(10) 0.0358(9) 0.0014(7) 0.0141(7) -0.0051(7)
    C14 0.0303(8) 0.0317(9) 0.0263(8) -0.0020(6) 0.0062(6) -0.0061(6)
    C15 0.0356(9) 0.0336(9) 0.0441(10) -0.0114(7) 0.0175(8) -0.0116(8)
_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 O2 . 1.4960(10)
                    ?
    S C1 . 1.750(2) ?
    S C9 . 1.800(2) ?
    O1 C8 . 1.373(2) ?
    O1 C7 . 1.386(2) ?
    C1 C8 . 1.357(2) ?
    C1 C2 . 1.447(2) ?
    C2 C3 . 1.395(2) ?
    C2 C7 . 1.395(2) ?
    C3 C4 . 1.388(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.396(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.385(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.378(2) ?
    C6 H6 . 0.9500 ?
    C8 C15 . 1.476(2) ?
    C9 C10 . 1.378(2) ?
    C9 C14 . 1.390(2) ?
    C10 C11 . 1.392(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.380(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.385(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.385(2) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 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
    O2 S C1 . . 109.46(7) ?
    O2 S C9 . . 106.26(7) ?
    C1 S C9 . . 98.33(7) ?
    C8 O1 C7 . . 106.50(10)
                          ?
    C8 C1 C2 . . 107.70(10)
                          ?
    C8 C1 S . . 122.20(10)
                         ?
    C2 C1 S . . 130.20(10)
                         ?
    C3 C2 C7 . . 119.2(2) ?
    C3 C2 C1 . . 136.10(10)
                          ?
    C7 C2 C1 . . 104.60(10)
                          ?
    C4 C3 C2 . . 117.6(2) ?
    C4 C3 H3 . . 121.2 ?
    C2 C3 H3 . . 121.2 ?
    C3 C4 C5 . . 121.5(2) ?
    C3 C4 H4 . . 119.2 ?
    C5 C4 H4 . . 119.2 ?
    C6 C5 C4 . . 121.6(2) ?
    C6 C5 H5 . . 119.2 ?
    C4 C5 H5 . . 119.2 ?
    C7 C6 C5 . . 116.1(2) ?
    C7 C6 H6 . . 122.0 ?
    C5 C6 H6 . . 122.0 ?
    C6 C7 O1 . . 125.6(2) ?
    C6 C7 C2 . . 123.9(2) ?
    O1 C7 C2 . . 110.50(10)
                          ?
    C1 C8 O1 . . 110.8(2) ?
    C1 C8 C15 . . 133.1(2) ?
    O1 C8 C15 . . 116.10(10)
                           ?
    C10 C9 C14 . . 121.2(2) ?
    C10 C9 S . . 117.90(10)
                          ?
    C14 C9 S . . 120.60(10)
                          ?
    C9 C10 C11 . . 119.2(2) ?
    C9 C10 H10 . . 120.4 ?
    C11 C10 H10 . . 120.4 ?
    C12 C11 C10 . . 120.2(2) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C11 C12 C13 . . 120.0(2) ?
    C11 C12 H12 . . 120.0 ?
    C13 C12 H12 . . 120.0 ?
    C14 C13 C12 . . 120.5(2) ?
    C14 C13 H13 . . 119.8 ?
    C12 C13 H13 . . 119.8 ?
    C13 C14 C9 . . 118.9(2) ?
    C13 C14 H14 . . 120.6 ?
    C9 C14 H14 . . 120.6 ?
    C8 C15 H15A . . 109.5 ?
    C8 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C8 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 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
    O2 S C1 C8 . . . . 126.30(10)
                                ?
    C9 S C1 C8 . . . . -123.20(10)
                                 ?
    O2 S C1 C2 . . . . -55.6(2) ?
    C9 S C1 C2 . . . . 55.0(2) ?
    C8 C1 C2 C3 . . . . -179.9(2) ?
    S C1 C2 C3 . . . . 1.7(3) ?
    C8 C1 C2 C7 . . . . 0.2(2) ?
    S C1 C2 C7 . . . . -178.10(10)
                                 ?
    C7 C2 C3 C4 . . . . 1.1(2) ?
    C1 C2 C3 C4 . . . . -178.7(2) ?
    C2 C3 C4 C5 . . . . -0.6(2) ?
    C3 C4 C5 C6 . . . . -0.7(3) ?
    C4 C5 C6 C7 . . . . 1.3(2) ?
    C5 C6 C7 O1 . . . . 178.70(10)
                                 ?
    C5 C6 C7 C2 . . . . -0.8(2) ?
    C8 O1 C7 C6 . . . . -179.6(2) ?
    C8 O1 C7 C2 . . . . -0.1(2) ?
    C3 C2 C7 C6 . . . . -0.4(2) ?
    C1 C2 C7 C6 . . . . 179.4(2) ?
    C3 C2 C7 O1 . . . . -179.90(10)
                                  ?
    C1 C2 C7 O1 . . . . -0.1(2) ?
    C2 C1 C8 O1 . . . . -0.3(2) ?
    S C1 C8 O1 . . . . 178.20(10)
                                ?
    C2 C1 C8 C15 . . . . -179.5(2) ?
    S C1 C8 C15 . . . . -1.0(3) ?
    C7 O1 C8 C1 . . . . 0.3(2) ?
    C7 O1 C8 C15 . . . . 179.60(10)
                                  ?
    O2 S C9 C10 . . . . -17.0(2) ?
    C1 S C9 C10 . . . . -130.20(10)
                                  ?
    O2 S C9 C14 . . . . 168.50(10)
                                 ?
    C1 S C9 C14 . . . . 55.30(10)
                                ?
    C14 C9 C10 C11 . . . . 0.6(2) ?
    S C9 C10 C11 . . . . -173.90(10)
                                   ?
    C9 C10 C11 C12 . . . . -0.2(3) ?
    C10 C11 C12 C13 . . . . -0.3(3) ?
    C11 C12 C13 C14 . . . . 0.6(3) ?
    C12 C13 C14 C9 . . . . -0.3(3) ?
    C10 C9 C14 C13 . . . . -0.3(2) ?
    S C9 C14 C13 . . . . 174.00(10)
                                  ?
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
    C4 H4 O2 4_566 0.95 2.59 3.387(2) 141.7
    C15 H15C O2 4_576 0.98 2.42 3.232(2) 140.5
    C12 H12 Cg2 3_566 0.95 3.20 3.629(3) 152.1
