#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239480.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_2239480
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-2-methyl-3-(3-methylphenylsulfinyl)-1-benzofuran
;
_journal_coeditor_code           SU2700
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o320
_journal_paper_doi               10.1107/S1600536814003365
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C16 H13 Br O2 S'
_chemical_formula_moiety         'C16 H13 Br O2 S'
_chemical_formula_sum            'C16 H13 Br O2 S'
_chemical_formula_weight         349.23
_chemical_name_systematic
;
5-Bromo-2-methyl-3-(3-methylphenylsulfinyl)-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                106.9560(10)
_cell_angle_beta                 90.4410(10)
_cell_angle_gamma                108.9000(10)
_cell_formula_units_Z            2
_cell_length_a                   8.42090(10)
_cell_length_b                   8.90420(10)
_cell_length_c                   10.86280(10)
_cell_measurement_reflns_used    8553
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.54
_cell_volume                     732.383(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13736
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.946
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.536
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0245
_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)+(0.0306P)²+0.2396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                3391
_reflns_number_total             3667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2700sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        732.383(14)
_cod_database_code               2239480
_cod_database_fobs_code          2239480
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 0.04187(2) 0.75979(2) 0.479648(15) 0.03138(7) Uani d . 1 1
S S1 0.24413(5) 0.49344(5) 0.90916(4) 0.02597(9) Uani d . 1 1
O O1 0.23301(15) 0.94970(14) 1.04896(11) 0.0283(2) Uani d . 1 1
O O2 0.08675(15) 0.36872(15) 0.82700(13) 0.0339(3) Uani d . 1 1
C C1 0.23351(19) 0.69433(19) 0.93705(15) 0.0230(3) Uani d . 1 1
C C2 0.18550(18) 0.76541(18) 0.84534(14) 0.0209(3) Uani d . 1 1
C C3 0.14284(19) 0.71368(19) 0.71172(15) 0.0224(3) Uani d . 1 1
H H3 0.1423 0.6081 0.6579 0.027 Uiso calc R 1 1
C C4 0.10115(19) 0.82404(19) 0.66114(15) 0.0235(3) Uani d . 1 1
C C5 0.0980(2) 0.9788(2) 0.73792(17) 0.0271(3) Uani d . 1 1
H H5 0.0661 1.0488 0.6989 0.033 Uiso calc R 1 1
C C6 0.1413(2) 1.03082(19) 0.87084(17) 0.0273(3) Uani d . 1 1
H H6 0.1405 1.1358 0.9249 0.033 Uiso calc R 1 1
C C7 0.18532(19) 0.92194(19) 0.92009(15) 0.0234(3) Uani d . 1 1
C C8 0.2602(2) 0.8082(2) 1.05582(16) 0.0266(3) Uani d . 1 1
C C9 0.3152(3) 0.8114(3) 1.18646(17) 0.0384(4) Uani d . 1 1
H H9A 0.3161 0.7005 1.1833 0.058 Uiso calc R 1 1
H H9B 0.2369 0.8424 1.2469 0.058 Uiso calc R 1 1
H H9C 0.4291 0.8934 1.2159 0.058 Uiso calc R 1 1
C C10 0.40882(18) 0.50755(19) 0.80452(15) 0.0234(3) Uani d . 1 1
C C11 0.5604(2) 0.6403(2) 0.84122(18) 0.0317(3) Uani d . 1 1
H H11 0.5760 0.7300 0.9187 0.038 Uiso calc R 1 1
C C12 0.6883(2) 0.6386(2) 0.7623(2) 0.0384(4) Uani d . 1 1
H H12 0.7932 0.7281 0.7859 0.046 Uiso calc R 1 1
C C13 0.6648(2) 0.5077(2) 0.64917(19) 0.0345(4) Uani d . 1 1
H H13 0.7539 0.5090 0.5959 0.041 Uiso calc R 1 1
C C14 0.5133(2) 0.3745(2) 0.61235(17) 0.0289(3) Uani d . 1 1
C C15 0.3854(2) 0.3760(2) 0.69235(16) 0.0266(3) Uani d . 1 1
H H15 0.2810 0.2857 0.6697 0.032 Uiso calc R 1 1
C C16 0.4876(3) 0.2305(3) 0.4904(2) 0.0424(4) Uani d . 1 1
H H16A 0.5240 0.2737 0.4181 0.064 Uiso calc R 1 1
H H16B 0.3678 0.1614 0.4714 0.064 Uiso calc R 1 1
H H16C 0.5545 0.1629 0.5023 0.064 Uiso calc R 1 1
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_566 175.63(5)
O2 S1 C1 . 108.56(7)
O2 S1 C10 . 106.16(7)
C1 S1 C10 . 98.49(7)
C8 O1 C7 . 106.43(12)
C8 C1 C2 . 107.45(14)
C8 C1 S1 . 123.80(12)
C2 C1 S1 . 128.62(12)
C3 C2 C7 . 119.50(13)
C3 C2 C1 . 135.70(14)
C7 C2 C1 . 104.80(13)
C4 C3 C2 . 116.72(14)
C4 C3 H3 . 121.6
C2 C3 H3 . 121.6
C3 C4 C5 . 122.96(15)
C3 C4 Br1 . 118.47(12)
C5 C4 Br1 . 118.57(11)
C6 C5 C4 . 120.40(14)
C6 C5 H5 . 119.8
C4 C5 H5 . 119.8
C7 C6 C5 . 116.32(14)
C7 C6 H6 . 121.8
C5 C6 H6 . 121.8
C6 C7 O1 . 125.57(14)
C6 C7 C2 . 124.08(15)
O1 C7 C2 . 110.35(13)
C1 C8 O1 . 110.95(14)
C1 C8 C9 . 133.31(16)
O1 C8 C9 . 115.71(15)
C8 C9 H9A . 109.5
C8 C9 H9B . 109.5
H9A C9 H9B . 109.5
C8 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C15 C10 C11 . 121.21(15)
C15 C10 S1 . 118.01(12)
C11 C10 S1 . 120.56(13)
C12 C11 C10 . 118.38(17)
C12 C11 H11 . 120.8
C10 C11 H11 . 120.8
C11 C12 C13 . 120.62(16)
C11 C12 H12 . 119.7
C13 C12 H12 . 119.7
C12 C13 C14 . 121.11(17)
C12 C13 H13 . 119.4
C14 C13 H13 . 119.4
C13 C14 C15 . 118.14(16)
C13 C14 C16 . 121.43(17)
C15 C14 C16 . 120.43(16)
C10 C15 C14 . 120.54(15)
C10 C15 H15 . 119.7
C14 C15 H15 . 119.7
C14 C16 H16A . 109.5
C14 C16 H16B . 109.5
H16A C16 H16B . 109.5
C14 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 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 . 1.8988(16)
Br1 O2 2_566 3.2399(14)
S1 O2 . 1.4954(13)
S1 C1 . 1.7571(16)
S1 C10 . 1.7960(16)
O1 C8 . 1.373(2)
O1 C7 . 1.3810(19)
C1 C8 . 1.352(2)
C1 C2 . 1.444(2)
C2 C3 . 1.394(2)
C2 C7 . 1.394(2)
C3 C4 . 1.388(2)
C3 H3 . 0.9500
C4 C5 . 1.396(2)
C5 C6 . 1.387(2)
C5 H5 . 0.9500
C6 C7 . 1.377(2)
C6 H6 . 0.9500
C8 C9 . 1.479(2)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 C15 . 1.382(2)
C10 C11 . 1.387(2)
C11 C12 . 1.382(3)
C11 H11 . 0.9500
C12 C13 . 1.386(3)
C12 H12 . 0.9500
C13 C14 . 1.389(2)
C13 H13 . 0.9500
C14 C15 . 1.390(2)
C14 C16 . 1.507(3)
C15 H15 . 0.9500
C16 H16A . 0.9800
C16 H16B . 0.9800
C16 H16C . 0.9800
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 H9A Cg1 2_667 0.98 2.91 3.785(2) 150
C12 H12 Cg2 1_655 0.95 2.79 3.674(2) 154
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 129.11(14)
C10 S1 C1 C8 -120.59(14)
O2 S1 C1 C2 -46.22(16)
C10 S1 C1 C2 64.09(15)
C8 C1 C2 C3 179.77(17)
S1 C1 C2 C3 -4.3(3)
C8 C1 C2 C7 -0.75(17)
S1 C1 C2 C7 175.18(12)
C7 C2 C3 C4 -0.4(2)
C1 C2 C3 C4 179.07(16)
C2 C3 C4 C5 -1.1(2)
C2 C3 C4 Br1 -179.96(11)
C3 C4 C5 C6 1.5(2)
Br1 C4 C5 C6 -179.67(12)
C4 C5 C6 C7 -0.3(2)
C5 C6 C7 O1 179.71(14)
C5 C6 C7 C2 -1.2(2)
C8 O1 C7 C6 178.02(15)
C8 O1 C7 C2 -1.18(17)
C3 C2 C7 C6 1.6(2)
C1 C2 C7 C6 -178.02(15)
C3 C2 C7 O1 -179.22(13)
C1 C2 C7 O1 1.19(16)
C2 C1 C8 O1 0.05(18)
S1 C1 C8 O1 -176.13(11)
C2 C1 C8 C9 -178.18(18)
S1 C1 C8 C9 5.6(3)
C7 O1 C8 C1 0.68(17)
C7 O1 C8 C9 179.25(14)
O2 S1 C10 C15 -21.27(13)
C1 S1 C10 C15 -133.50(12)
O2 S1 C10 C11 164.08(13)
C1 S1 C10 C11 51.85(14)
C15 C10 C11 C12 0.3(3)
S1 C10 C11 C12 174.82(14)
C10 C11 C12 C13 0.2(3)
C11 C12 C13 C14 -0.4(3)
C12 C13 C14 C15 -0.1(3)
C12 C13 C14 C16 -179.16(18)
C11 C10 C15 C14 -0.8(2)
S1 C10 C15 C14 -175.41(12)
C13 C14 C15 C10 0.6(2)
C16 C14 C15 C10 179.75(15)
