#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/55/2235537.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_2235537
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-2-methyl-3-(4-methylphenylsulfonyl)-1-benzofuran
;
_journal_coeditor_code           LD2064
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2143
_journal_paper_doi               10.1107/S1600536812026918
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H13 Br O3 S'
_chemical_formula_moiety         'C16 H13 Br O3 S'
_chemical_formula_sum            'C16 H13 Br O3 S'
_chemical_formula_weight         365.23
_chemical_name_systematic
;
5-Bromo-2-methyl-3-(4-methylphenylsulfonyl)-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
_cell_angle_alpha                112.987(2)
_cell_angle_beta                 90.340(2)
_cell_angle_gamma                107.903(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2126(2)
_cell_length_b                   10.3607(3)
_cell_length_c                   11.1748(3)
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      3.00
_cell_volume                     723.93(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) 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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13654
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.990
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0340
_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)+(0.0410P)²+0.3896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2977
_reflns_number_total             3618
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ld2064.cif
_cod_data_source_block           I
_cod_original_cell_volume        723.93(3)
_cod_database_code               2235537
_cod_database_fobs_code          2235537
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 0.15488(4) 1.00069(3) 0.87021(2) 0.04424(11) Uani d . 1 2
S S1 -0.00690(8) 0.60478(6) 0.27695(5) 0.02645(13) Uani d . 1 2
O O1 0.3145(2) 1.01741(18) 0.35296(17) 0.0327(4) Uani d . 1 2
O O2 -0.1043(2) 0.5621(2) 0.14793(15) 0.0359(4) Uani d . 1 2
O O3 -0.1223(2) 0.58519(18) 0.37716(15) 0.0315(4) Uani d . 1 2
C C1 0.1341(3) 0.7923(2) 0.3393(2) 0.0261(4) Uani d . 1 2
C C2 0.1767(3) 0.8934(2) 0.4763(2) 0.0253(4) Uani d . 1 2
C C3 0.1348(3) 0.8827(3) 0.5943(2) 0.0277(5) Uani d . 1 2
H H3 0.0613 0.7907 0.5969 0.033 Uiso calc R 1 2
C C4 0.2051(3) 1.0124(3) 0.7073(2) 0.0321(5) Uani d . 1 2
C C5 0.3109(4) 1.1496(3) 0.7075(3) 0.0360(5) Uani d . 1 2
H H5 0.3537 1.2360 0.7879 0.043 Uiso calc R 1 2
C C6 0.3537(3) 1.1604(3) 0.5906(3) 0.0353(5) Uani d . 1 2
H H6 0.4257 1.2528 0.5881 0.042 Uiso calc R 1 2
C C7 0.2871(3) 1.0310(3) 0.4783(2) 0.0290(5) Uani d . 1 2
C C8 0.2210(3) 0.8717(3) 0.2700(2) 0.0295(5) Uani d . 1 2
C C9 0.2361(4) 0.8320(3) 0.1296(2) 0.0387(6) Uani d . 1 2
H H9A 0.3738 0.8462 0.1160 0.058 Uiso calc R 1 2
H H9B 0.1888 0.8958 0.1008 0.058 Uiso calc R 1 2
H H9C 0.1557 0.7276 0.0785 0.058 Uiso calc R 1 2
C C10 0.1604(3) 0.5089(2) 0.2602(2) 0.0261(4) Uani d . 1 2
C C11 0.2062(3) 0.4715(3) 0.3602(2) 0.0300(5) Uani d . 1 2
H H11 0.1513 0.5010 0.4395 0.036 Uiso calc R 1 2
C C12 0.3325(4) 0.3911(3) 0.3435(2) 0.0334(5) Uani d . 1 2
H H12 0.3611 0.3630 0.4110 0.040 Uiso calc R 1 2
C C13 0.4185(3) 0.3503(3) 0.2297(2) 0.0317(5) Uani d . 1 2
C C14 0.3751(4) 0.3926(3) 0.1327(2) 0.0353(5) Uani d . 1 2
H H14 0.4359 0.3679 0.0556 0.042 Uiso calc R 1 2
C C15 0.2461(4) 0.4695(3) 0.1453(2) 0.0334(5) Uani d . 1 2
H H15 0.2156 0.4956 0.0768 0.040 Uiso calc R 1 2
C C16 0.5507(4) 0.2586(3) 0.2102(3) 0.0420(6) Uani d . 1 2
H H16A 0.4759 0.1540 0.1549 0.063 Uiso calc R 1 2
H H16B 0.6016 0.2675 0.2956 0.063 Uiso calc R 1 2
H H16C 0.6609 0.2943 0.1673 0.063 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 Br1 2_577 152.33(7)
O2 S1 O3 . 119.55(10)
O2 S1 C1 . 108.57(11)
O3 S1 C1 . 106.20(10)
O2 S1 C10 . 107.83(10)
O3 S1 C10 . 108.00(10)
C1 S1 C10 . 105.93(10)
C8 O1 C7 . 107.36(17)
C8 C1 C2 . 107.5(2)
C8 C1 S1 . 127.18(18)
C2 C1 S1 . 125.28(16)
C3 C2 C7 . 119.3(2)
C3 C2 C1 . 136.0(2)
C7 C2 C1 . 104.72(19)
C4 C3 C2 . 116.8(2)
C4 C3 H3 . 121.6
C2 C3 H3 . 121.6
C3 C4 C5 . 123.3(2)
C3 C4 Br1 . 117.80(18)
C5 C4 Br1 . 118.86(18)
C6 C5 C4 . 120.0(2)
C6 C5 H5 . 120.0
C4 C5 H5 . 120.0
C7 C6 C5 . 116.8(2)
C7 C6 H6 . 121.6
C5 C6 H6 . 121.6
C6 C7 O1 . 126.0(2)
C6 C7 C2 . 123.8(2)
O1 C7 C2 . 110.19(19)
C1 C8 O1 . 110.2(2)
C1 C8 C9 . 133.6(2)
O1 C8 C9 . 116.2(2)
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
C11 C10 C15 . 120.3(2)
C11 C10 S1 . 120.07(18)
C15 C10 S1 . 119.65(18)
C12 C11 C10 . 119.4(2)
C12 C11 H11 . 120.3
C10 C11 H11 . 120.3
C11 C12 C13 . 121.2(2)
C11 C12 H12 . 119.4
C13 C12 H12 . 119.4
C14 C13 C12 . 118.4(2)
C14 C13 C16 . 120.6(2)
C12 C13 C16 . 121.0(2)
C15 C14 C13 . 121.6(2)
C15 C14 H14 . 119.2
C13 C14 H14 . 119.2
C14 C15 C10 . 119.1(2)
C14 C15 H15 . 120.5
C10 C15 H15 . 120.5
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 Br1 2_577 3.6736(5)
Br1 C4 . 1.901(2)
S1 O2 . 1.4376(16)
S1 O3 . 1.4395(16)
S1 C1 . 1.736(2)
S1 C10 . 1.753(2)
O1 C8 . 1.366(3)
O1 C7 . 1.374(3)
C1 C8 . 1.363(3)
C1 C2 . 1.442(3)
C2 C3 . 1.392(3)
C2 C7 . 1.395(3)
C3 C4 . 1.380(3)
C3 H3 . 0.9500
C4 C5 . 1.391(4)
C5 C6 . 1.382(4)
C5 H5 . 0.9500
C6 C7 . 1.373(3)
C6 H6 . 0.9500
C8 C9 . 1.472(3)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 C11 . 1.385(3)
C10 C15 . 1.397(3)
C11 C12 . 1.381(4)
C11 H11 . 0.9500
C12 C13 . 1.390(3)
C12 H12 . 0.9500
C13 C14 . 1.384(3)
C13 C16 . 1.503(4)
C14 C15 . 1.375(4)
C14 H14 . 0.9500
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
C11 H11 O3 2_566 0.95 2.52 3.236(3) 132.2
C15 H15 O2 2_565 0.95 2.41 3.287(3) 153.0
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 -29.7(2)
O3 S1 C1 C8 -159.5(2)
C10 S1 C1 C8 85.8(2)
O2 S1 C1 C2 148.94(19)
O3 S1 C1 C2 19.2(2)
C10 S1 C1 C2 -95.5(2)
C8 C1 C2 C3 -178.9(3)
S1 C1 C2 C3 2.2(4)
C8 C1 C2 C7 1.0(2)
S1 C1 C2 C7 -177.92(17)
C7 C2 C3 C4 0.8(3)
C1 C2 C3 C4 -179.3(2)
C2 C3 C4 C5 0.9(4)
C2 C3 C4 Br1 -178.74(16)
C3 C4 C5 C6 -1.3(4)
Br1 C4 C5 C6 178.33(18)
C4 C5 C6 C7 0.0(4)
C5 C6 C7 O1 -179.7(2)
C5 C6 C7 C2 1.7(4)
C8 O1 C7 C6 -178.4(2)
C8 O1 C7 C2 0.4(2)
C3 C2 C7 C6 -2.1(3)
C1 C2 C7 C6 177.9(2)
C3 C2 C7 O1 179.09(19)
C1 C2 C7 O1 -0.8(2)
C2 C1 C8 O1 -0.8(3)
S1 C1 C8 O1 178.09(16)
C2 C1 C8 C9 177.9(3)
S1 C1 C8 C9 -3.2(4)
C7 O1 C8 C1 0.3(2)
C7 O1 C8 C9 -178.7(2)
O2 S1 C10 C11 -150.10(18)
O3 S1 C10 C11 -19.6(2)
C1 S1 C10 C11 93.82(19)
O2 S1 C10 C15 29.5(2)
O3 S1 C10 C15 159.94(17)
C1 S1 C10 C15 -86.62(19)
C15 C10 C11 C12 -2.0(3)
S1 C10 C11 C12 177.55(17)
C10 C11 C12 C13 1.7(3)
C11 C12 C13 C14 0.2(3)
C11 C12 C13 C16 -178.0(2)
C12 C13 C14 C15 -1.8(4)
C16 C13 C14 C15 176.4(2)
C13 C14 C15 C10 1.5(4)
C11 C10 C15 C14 0.4(3)
S1 C10 C15 C14 -179.15(18)
