#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239202.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239202
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-1-benzofuran
;
_journal_coeditor_code           FJ2667
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o461
_journal_paper_doi               10.1107/S1600536814005844
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H17 Br O2 S'
_chemical_formula_moiety         'C18 H17 Br O2 S'
_chemical_formula_sum            'C18 H17 Br O2 S'
_chemical_formula_weight         377.29
_chemical_melting_point_gt       420
_chemical_melting_point_lt       419
_chemical_name_systematic
;
5-Bromo-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-1-benzofuran
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                68.8670(10)
_cell_angle_beta                 89.1460(10)
_cell_angle_gamma                71.3610(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3921(2)
_cell_length_b                   10.2909(3)
_cell_length_c                   11.8701(3)
_cell_measurement_reflns_used    8443
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.25
_cell_volume                     792.91(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
DIAMOND (Brandenburg, 1998)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13645
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.728
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.470
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.3263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0755
_reflns_number_gt                3145
_reflns_number_total             3457
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2667sup1.cif
_cod_data_source_block           I
_cod_database_code               2239202
_cod_database_fobs_code          2239202
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br Br1 0.99213(3) 0.28117(2) 1.076443(17) 0.03316(9) Uani d . 1 2
S S1 0.64111(7) 0.80626(5) 0.58929(4) 0.02572(12) Uani d . 1 2
O O1 0.80567(19) 0.41973(14) 0.55125(12) 0.0243(3) Uani d . 1 2
O O2 0.7922(2) 0.81341(17) 0.66688(15) 0.0380(4) Uani d . 1 2
C C1 0.7074(3) 0.6207(2) 0.60113(17) 0.0226(4) Uani d . 1 2
C C2 0.7941(3) 0.4927(2) 0.71109(17) 0.0232(4) Uani d . 1 2
C C3 0.8306(3) 0.4680(2) 0.83342(17) 0.0251(4) Uani d . 1 2
H H3 0.7908 0.5463 0.8627 0.030 Uiso calc R 1 2
C C4 0.9278(3) 0.3240(2) 0.90957(17) 0.0262(4) Uani d . 1 2
C C5 0.9886(3) 0.2066(2) 0.86941(18) 0.0269(4) Uani d . 1 2
H H5 1.0556 0.1097 0.9262 0.032 Uiso calc R 1 2
C C6 0.9532(3) 0.2284(2) 0.74878(18) 0.0252(4) Uani d . 1 2
C C7 0.8532(3) 0.3738(2) 0.67370(17) 0.0231(4) Uani d . 1 2
C C8 0.7173(3) 0.5711(2) 0.50770(17) 0.0231(4) Uani d . 1 2
C C9 1.0208(3) 0.1073(2) 0.70051(19) 0.0314(4) Uani d . 1 2
H H9A 0.9108 0.0820 0.6816 0.047 Uiso calc R 1 2
H H9B 1.1140 0.0198 0.7618 0.047 Uiso calc R 1 2
H H9C 1.0816 0.1406 0.6266 0.047 Uiso calc R 1 2
C C10 0.6536(3) 0.6380(2) 0.37788(17) 0.0236(4) Uani d . 1 2
C C11 0.5193(3) 0.7799(2) 0.32352(18) 0.0273(4) Uani d . 1 2
H H11 0.4689 0.8370 0.3715 0.033 Uiso calc R 1 2
C C12 0.4589(3) 0.8382(2) 0.20024(18) 0.0302(4) Uani d . 1 2
H H12 0.3686 0.9355 0.1646 0.036 Uiso calc R 1 2
C C13 0.5276(3) 0.7571(2) 0.12746(18) 0.0305(4) Uani d . 1 2
C C14 0.6616(3) 0.6152(2) 0.18236(19) 0.0309(4) Uani d . 1 2
H H14 0.7102 0.5578 0.1345 0.037 Uiso calc R 1 2
C C15 0.7248(3) 0.5567(2) 0.30458(18) 0.0273(4) Uani d . 1 2
H H15 0.8175 0.4604 0.3395 0.033 Uiso calc R 1 2
C C16 0.4606(3) 0.8183(3) -0.00608(19) 0.0407(5) Uani d . 1 2
H H16A 0.3793 0.7662 -0.0213 0.061 Uiso calc R 1 2
H H16B 0.5721 0.8047 -0.0517 0.061 Uiso calc R 1 2
H H16C 0.3865 0.9241 -0.0324 0.061 Uiso calc R 1 2
C C17 0.4326(3) 0.8128(2) 0.67180(19) 0.0314(5) Uani d . 1 2
H H17A 0.4619 0.7210 0.7452 0.038 Uiso calc R 1 2
H H17B 0.4015 0.8974 0.6986 0.038 Uiso calc R 1 2
C C18 0.2603(3) 0.8292(2) 0.5931(2) 0.0336(5) Uani d . 1 2
H H18A 0.2232 0.9248 0.5247 0.050 Uiso calc R 1 2
H H18B 0.1527 0.8241 0.6418 0.050 Uiso calc R 1 2
H H18C 0.2939 0.7492 0.5621 0.050 Uiso calc R 1 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C4 Br1 O2 2_767 164.97(7)
O2 S1 C1 . 106.64(9)
O2 S1 C17 . 106.82(10)
C1 S1 C17 . 98.32(10)
C7 O1 C8 . 107.13(14)
C8 C1 C2 . 107.24(16)
C8 C1 S1 . 127.11(15)
C2 C1 S1 . 124.84(14)
C7 C2 C3 . 119.30(17)
C7 C2 C1 . 104.87(16)
C3 C2 C1 . 135.80(17)
C4 C3 C2 . 116.46(17)
C4 C3 H3 . 121.8
C2 C3 H3 . 121.8
C3 C4 C5 . 123.18(18)
C3 C4 Br1 . 119.36(15)
C5 C4 Br1 . 117.42(14)
C6 C5 C4 . 121.36(17)
C6 C5 H5 . 119.3
C4 C5 H5 . 119.3
C5 C6 C7 . 114.64(17)
C5 C6 C9 . 123.41(17)
C7 C6 C9 . 121.92(18)
O1 C7 C2 . 110.82(16)
O1 C7 C6 . 124.11(16)
C2 C7 C6 . 125.04(18)
C1 C8 O1 . 109.93(16)
C1 C8 C10 . 135.84(17)
O1 C8 C10 . 114.21(16)
C6 C9 H9A . 109.5
C6 C9 H9B . 109.5
H9A C9 H9B . 109.5
C6 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C11 C10 C15 . 118.32(17)
C11 C10 C8 . 122.23(17)
C15 C10 C8 . 119.43(17)
C12 C11 C10 . 120.49(18)
C12 C11 H11 . 119.8
C10 C11 H11 . 119.8
C11 C12 C13 . 121.33(19)
C11 C12 H12 . 119.3
C13 C12 H12 . 119.3
C12 C13 C14 . 117.90(18)
C12 C13 C16 . 121.8(2)
C14 C13 C16 . 120.3(2)
C15 C14 C13 . 121.33(19)
C15 C14 H14 . 119.3
C13 C14 H14 . 119.3
C14 C15 C10 . 120.62(18)
C14 C15 H15 . 119.7
C10 C15 H15 . 119.7
C13 C16 H16A . 109.5
C13 C16 H16B . 109.5
H16A C16 H16B . 109.5
C13 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
C18 C17 S1 . 111.08(15)
C18 C17 H17A . 109.4
S1 C17 H17A . 109.4
C18 C17 H17B . 109.4
S1 C17 H17B . 109.4
H17A C17 H17B . 108.0
C17 C18 H18A . 109.5
C17 C18 H18B . 109.5
H18A C18 H18B . 109.5
C17 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.8996(19)
Br1 O2 2_767 3.1284(15)
S1 O2 . 1.4943(15)
S1 C1 . 1.7658(19)
S1 C17 . 1.810(2)
O1 C7 . 1.369(2)
O1 C8 . 1.378(2)
C1 C8 . 1.370(3)
C1 C2 . 1.447(3)
C2 C7 . 1.389(3)
C2 C3 . 1.396(3)
C3 C4 . 1.379(3)
C3 H3 . 0.9500
C4 C5 . 1.397(3)
C5 C6 . 1.382(3)
C5 H5 . 0.9500
C6 C7 . 1.390(3)
C6 C9 . 1.496(3)
C8 C10 . 1.456(3)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 C11 . 1.396(3)
C10 C15 . 1.401(3)
C11 C12 . 1.384(3)
C11 H11 . 0.9500
C12 C13 . 1.392(3)
C12 H12 . 0.9500
C13 C14 . 1.395(3)
C13 C16 . 1.503(3)
C14 C15 . 1.377(3)
C14 H14 . 0.9500
C15 H15 . 0.9500
C16 H16A . 0.9800
C16 H16B . 0.9800
C16 H16C . 0.9800
C17 C18 . 1.519(3)
C17 H17A . 0.9900
C17 H17B . 0.9900
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800
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
O2 S1 C1 C8 -130.72(18)
C17 S1 C1 C8 118.85(18)
O2 S1 C1 C2 37.58(19)
C17 S1 C1 C2 -72.85(18)
C8 C1 C2 C7 0.9(2)
S1 C1 C2 C7 -169.35(14)
C8 C1 C2 C3 179.1(2)
S1 C1 C2 C3 8.8(3)
C7 C2 C3 C4 1.0(3)
C1 C2 C3 C4 -177.0(2)
C2 C3 C4 C5 0.1(3)
C2 C3 C4 Br1 177.69(14)
C3 C4 C5 C6 -0.4(3)
Br1 C4 C5 C6 -178.01(15)
C4 C5 C6 C7 -0.4(3)
C4 C5 C6 C9 177.98(19)
C8 O1 C7 C2 1.0(2)
C8 O1 C7 C6 -176.82(18)
C3 C2 C7 O1 -179.73(16)
C1 C2 C7 O1 -1.2(2)
C3 C2 C7 C6 -1.9(3)
C1 C2 C7 C6 176.64(18)
C5 C6 C7 O1 179.12(17)
C9 C6 C7 O1 0.7(3)
C5 C6 C7 C2 1.6(3)
C9 C6 C7 C2 -176.86(19)
C2 C1 C8 O1 -0.3(2)
S1 C1 C8 O1 169.66(13)
C2 C1 C8 C10 177.6(2)
S1 C1 C8 C10 -12.4(3)
C7 O1 C8 C1 -0.4(2)
C7 O1 C8 C10 -178.87(16)
C1 C8 C10 C11 -15.2(4)
O1 C8 C10 C11 162.70(17)
C1 C8 C10 C15 166.5(2)
O1 C8 C10 C15 -15.6(3)
C15 C10 C11 C12 -0.1(3)
C8 C10 C11 C12 -178.39(19)
C10 C11 C12 C13 0.8(3)
C11 C12 C13 C14 -0.7(3)
C11 C12 C13 C16 179.0(2)
C12 C13 C14 C15 -0.2(3)
C16 C13 C14 C15 -179.9(2)
C13 C14 C15 C10 0.9(3)
C11 C10 C15 C14 -0.8(3)
C8 C10 C15 C14 177.56(18)
O2 S1 C17 C18 171.58(14)
C1 S1 C17 C18 -78.14(16)
