##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2013-06-19
_journal_date_accepted     2013-06-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      8
_journal_page_first     o1205
_journal_page_last     o1205
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813017753
_journal_coeditor_code     NC2313
_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-(4-Bromophenylsulfinyl)-2,5,6-trimethyl-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
;
    '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-(4-Bromophenylsulfinyl)-2,5,6-trimethyl-1-benzofuran
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H15 Br O2 S'
_chemical_formula_sum     'C17 H15 Br O2 S'
_chemical_formula_iupac     'C17 H15 Br O2 S'
_chemical_formula_weight     363.26
_chemical_melting_point_gt     446
_chemical_melting_point_lt     447
_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     20.0084(8)
_cell_length_b     7.1890(3)
_cell_length_c     10.7804(4)
_cell_angle_alpha     90.00
_cell_angle_beta     101.478(2)
_cell_angle_gamma     90.00
_cell_volume     1519.65(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6275
_cell_measurement_theta_min     3.12
_cell_measurement_theta_max     27.16
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.588
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     736
_exptl_absorpt_coefficient_mu     2.843
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.4249
_exptl_absorpt_correction_T_max     0.7457
_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     26485
_diffrn_reflns_av_R_equivalents     0.0707
_diffrn_reflns_av_sigmaI/netI     0.0569
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     28.38
_diffrn_reflns_theta_full     28.38
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -26
_diffrn_reflns_limit_h_max     26
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_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     3791
_reflns_number_gt     2928
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0589
_refine_ls_R_factor_gt     0.0408
_refine_ls_wR_factor_gt     0.1033
_refine_ls_wR_factor_ref     0.1137
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     3791
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0459P)²+0.8553P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.750
_refine_diff_density_min     -0.862
_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'
    'Br' 'Br' -0.2901 2.4595
                         '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 for Windows (Farrugia, 2012)
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.471187(16) 0.90385(6) 0.33352(3) 0.06164(16) Uani d . 1 2 . .
    S S1 0.30484(3) 0.38470(9) 0.64879(6) 0.02963(16) Uani d . 1 2 . .
    O O1 0.11729(8) 0.5558(2) 0.62907(13) 0.0245(4) Uani d . 1 2 . .
    O O2 0.30702(10) 0.1917(3) 0.5990(2) 0.0456(5) Uani d . 1 2 . .
    C C1 0.22159(11) 0.4684(3) 0.60389(19) 0.0230(5) Uani d . 1 2 . .
    C C2 0.17882(11) 0.4857(3) 0.47877(19) 0.0218(4) Uani d . 1 2 . .
    C C3 0.18654(12) 0.4633(3) 0.35339(19) 0.0240(5) Uani d . 1 2 . .
    H H3 0.2292 0.4267 0.3354 0.029 Uiso calc R 1 2 . .
    C C4 0.13130(12) 0.4951(3) 0.25574(19) 0.0242(5) Uani d . 1 2 . .
    C C5 0.06756(12) 0.5501(3) 0.28199(19) 0.0230(4) Uani d . 1 2 . .
    C C6 0.06000(11) 0.5739(3) 0.40622(19) 0.0230(5) Uani d . 1 2 . .
    H H6 0.0178 0.6124 0.4253 0.028 Uiso calc R 1 2 . .
    C C7 0.11582(11) 0.5398(3) 0.50083(18) 0.0220(4) Uani d . 1 2 . .
    C C8 0.18216(12) 0.5111(3) 0.68885(19) 0.0245(5) Uani d . 1 2 . .
    C C9 0.13935(14) 0.4700(4) 0.1205(2) 0.0327(6) Uani d . 1 2 . .
    H H9A 0.1875 0.4477 0.1187 0.049 Uiso calc R 1 2 . .
    H H9B 0.1238 0.5826 0.0720 0.049 Uiso calc R 1 2 . .
    H H9C 0.1120 0.3635 0.0831 0.049 Uiso calc R 1 2 . .
    C C10 0.00712(13) 0.5824(4) 0.1766(2) 0.0302(5) Uani d . 1 2 . .
    H H10A -0.0325 0.6167 0.2123 0.045 Uiso calc R 1 2 . .
    H H10B -0.0030 0.4683 0.1265 0.045 Uiso calc R 1 2 . .
    H H10C 0.0174 0.6831 0.1221 0.045 Uiso calc R 1 2 . .
    C C11 0.19543(14) 0.5183(4) 0.82940(19) 0.0313(5) Uani d . 1 2 . .
    H H11A 0.2425 0.4795 0.8633 0.047 Uiso calc R 1 2 . .
    H H11B 0.1639 0.4344 0.8607 0.047 Uiso calc R 1 2 . .
    H H11C 0.1887 0.6456 0.8569 0.047 Uiso calc R 1 2 . .
    C C12 0.34419(11) 0.5327(4) 0.5498(2) 0.0270(5) Uani d . 1 2 . .
    C C13 0.38253(14) 0.4501(4) 0.4718(3) 0.0407(7) Uani d . 1 2 . .
    H H13 0.3838 0.3186 0.4644 0.049 Uiso calc R 1 2 . .
    C C14 0.41911(14) 0.5619(5) 0.4046(3) 0.0469(8) Uani d . 1 2 . .
    H H14 0.4451 0.5078 0.3492 0.056 Uiso calc R 1 2 . .
    C C15 0.41750(12) 0.7519(5) 0.4186(2) 0.0379(7) Uani d . 1 2 . .
    C C16 0.37837(13) 0.8355(4) 0.4953(2) 0.0354(6) Uani d . 1 2 . .
    H H16 0.3768 0.9671 0.5022 0.042 Uiso calc R 1 2 . .
    C C17 0.34162(12) 0.7238(4) 0.5615(2) 0.0302(5) Uani d . 1 2 . .
    H H17 0.3146 0.7782 0.6151 0.036 Uiso calc R 1 2 . .
_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
    Br1 C15 . 1.892(3) ?
    S1 O2 . 1.492(2) ?
    S1 C1 . 1.746(2) ?
    S1 C12 . 1.796(2) ?
    O1 C8 . 1.368(3) ?
    O1 C7 . 1.382(2) ?
    C1 C8 . 1.358(3) ?
    C1 C2 . 1.452(3) ?
    C2 C7 . 1.384(3) ?
    C2 C3 . 1.400(3) ?
    C3 C4 . 1.385(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.417(3) ?
    C4 C9 . 1.509(3) ?
    C5 C6 . 1.388(3) ?
    C5 C10 . 1.504(3) ?
    C6 C7 . 1.376(3) ?
    C6 H6 . 0.9500 ?
    C8 C11 . 1.486(3) ?
    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 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C13 . 1.380(3) ?
    C12 C17 . 1.382(4) ?
    C13 C14 . 1.385(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.375(5) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.384(4) ?
    C16 C17 . 1.380(3) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
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 S1 C1 . . 108.38(11) ?
    O2 S1 C12 . . 106.81(11) ?
    C1 S1 C12 . . 97.93(11) ?
    C8 O1 C7 . . 106.33(16) ?
    C8 C1 C2 . . 107.05(19) ?
    C8 C1 S1 . . 122.76(16) ?
    C2 C1 S1 . . 129.82(16) ?
    C7 C2 C3 . . 118.5(2) ?
    C7 C2 C1 . . 104.66(18) ?
    C3 C2 C1 . . 136.8(2) ?
    C4 C3 C2 . . 119.4(2) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 120.54(18) ?
    C3 C4 C9 . . 119.5(2) ?
    C5 C4 C9 . . 120.0(2) ?
    C6 C5 C4 . . 120.2(2) ?
    C6 C5 C10 . . 119.0(2) ?
    C4 C5 C10 . . 120.84(19) ?
    C7 C6 C5 . . 117.7(2) ?
    C7 C6 H6 . . 121.1 ?
    C5 C6 H6 . . 121.1 ?
    C6 C7 O1 . . 125.39(19) ?
    C6 C7 C2 . . 123.72(19) ?
    O1 C7 C2 . . 110.88(19) ?
    C1 C8 O1 . . 111.08(18) ?
    C1 C8 C11 . . 133.3(2) ?
    O1 C8 C11 . . 115.63(19) ?
    C4 C9 H9A . . 109.5 ?
    C4 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C4 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C8 C11 H11A . . 109.5 ?
    C8 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C8 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C13 C12 C17 . . 121.3(2) ?
    C13 C12 S1 . . 118.0(2) ?
    C17 C12 S1 . . 120.38(17) ?
    C12 C13 C14 . . 119.0(3) ?
    C12 C13 H13 . . 120.5 ?
    C14 C13 H13 . . 120.5 ?
    C15 C14 C13 . . 119.5(2) ?
    C15 C14 H14 . . 120.3 ?
    C13 C14 H14 . . 120.3 ?
    C14 C15 C16 . . 121.7(2) ?
    C14 C15 Br1 . . 119.5(2) ?
    C16 C15 Br1 . . 118.8(2) ?
    C17 C16 C15 . . 118.7(3) ?
    C17 C16 H16 . . 120.7 ?
    C15 C16 H16 . . 120.7 ?
    C16 C17 C12 . . 119.8(2) ?
    C16 C17 H17 . . 120.1 ?
    C12 C17 H17 . . 120.1 ?
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 S1 C1 C8 . . . . 115.6(2) ?
    C12 S1 C1 C8 . . . . -133.6(2) ?
    O2 S1 C1 C2 . . . . -56.5(3) ?
    C12 S1 C1 C2 . . . . 54.3(2) ?
    C8 C1 C2 C7 . . . . 0.3(3) ?
    S1 C1 C2 C7 . . . . 173.37(19) ?
    C8 C1 C2 C3 . . . . 179.8(3) ?
    S1 C1 C2 C3 . . . . -7.1(4) ?
    C7 C2 C3 C4 . . . . -0.2(3) ?
    C1 C2 C3 C4 . . . . -179.7(3) ?
    C2 C3 C4 C5 . . . . 0.1(4) ?
    C2 C3 C4 C9 . . . . -179.7(2) ?
    C3 C4 C5 C6 . . . . 0.4(4) ?
    C9 C4 C5 C6 . . . . -179.8(2) ?
    C3 C4 C5 C10 . . . . -179.2(2) ?
    C9 C4 C5 C10 . . . . 0.6(3) ?
    C4 C5 C6 C7 . . . . -0.9(3) ?
    C10 C5 C6 C7 . . . . 178.7(2) ?
    C5 C6 C7 O1 . . . . -179.7(2) ?
    C5 C6 C7 C2 . . . . 0.8(4) ?
    C8 O1 C7 C6 . . . . -179.5(2) ?
    C8 O1 C7 C2 . . . . 0.0(3) ?
    C3 C2 C7 C6 . . . . -0.3(4) ?
    C1 C2 C7 C6 . . . . 179.3(2) ?
    C3 C2 C7 O1 . . . . -179.8(2) ?
    C1 C2 C7 O1 . . . . -0.2(3) ?
    C2 C1 C8 O1 . . . . -0.3(3) ?
    S1 C1 C8 O1 . . . . -174.01(17) ?
    C2 C1 C8 C11 . . . . 179.6(3) ?
    S1 C1 C8 C11 . . . . 6.0(4) ?
    C7 O1 C8 C1 . . . . 0.2(3) ?
    C7 O1 C8 C11 . . . . -179.7(2) ?
    O2 S1 C12 C13 . . . . -15.3(2) ?
    C1 S1 C12 C13 . . . . -127.3(2) ?
    O2 S1 C12 C17 . . . . 171.18(18) ?
    C1 S1 C12 C17 . . . . 59.2(2) ?
    C17 C12 C13 C14 . . . . 0.1(4) ?
    S1 C12 C13 C14 . . . . -173.3(2) ?
    C12 C13 C14 C15 . . . . 1.2(4) ?
    C13 C14 C15 C16 . . . . -2.2(4) ?
    C13 C14 C15 Br1 . . . . 176.7(2) ?
    C14 C15 C16 C17 . . . . 1.7(4) ?
    Br1 C15 C16 C17 . . . . -177.17(18) ?
    C15 C16 C17 C12 . . . . -0.4(4) ?
    C13 C12 C17 C16 . . . . -0.5(4) ?
    S1 C12 C17 C16 . . . . 172.77(19) ?
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 H9C Cg1 4_565 0.98 2.89 3.537(4) 124.4
    C11 H11C Cg2 4_576 0.98 2.78 3.714(4) 159.0
