#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/20/2232027.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_2232027
loop_
_publ_author_name
'Seo, Pil Ja'
'Choi, Hong Dae'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_related_literature
;
For the pharmacological activity of benzofuran compounds, see: Aslam et
al. (2009); Galal et al. (2009); Khan et al.
(2005). For
natural products with benzofuran rings, see: Akgul & Anil (2003);
Soekamto
et al. (2003). For structural studies of
3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et
al. (2010, 2011).
;
_publ_section_title
;
 3-(3-Chlorophenylsulfonyl)-2,5-dimethyl-1-benzofuran
;
_journal_coeditor_code           QM2026
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2578
_journal_paper_doi               10.1107/S1600536811035720
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H13 Cl O3 S'
_chemical_formula_moiety         'C16 H13 Cl O3 S'
_chemical_formula_sum            'C16 H13 Cl O3 S'
_chemical_formula_weight         320.77
_chemical_name_systematic
;
3-(3-Chlorophenylsulfonyl)-2,5-dimethyl-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                84.023(3)
_cell_angle_beta                 81.514(3)
_cell_angle_gamma                72.378(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1000(4)
_cell_length_b                   8.8622(5)
_cell_length_c                   10.6898(6)
_cell_measurement_reflns_used    5186
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.42
_cell_volume                     721.90(7)
_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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            13538
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.2430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                2951
_reflns_number_total             3622
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               2232027
_cod_database_fobs_code          2232027
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
S S1 0.33167(5) 0.43504(5) 0.29715(4) 0.02475(13) Uani d . 1 1
Cl Cl1 -0.08568(7) 0.78553(6) -0.04210(5) 0.04248(16) Uani d . 1 1
O O1 0.49244(16) -0.00637(14) 0.20581(12) 0.0310(3) Uani d . 1 1
O O2 0.45023(15) 0.49763(14) 0.20924(13) 0.0328(3) Uani d . 1 1
O O3 0.31247(17) 0.46293(15) 0.42888(12) 0.0324(3) Uani d . 1 1
C C1 0.3859(2) 0.23236(19) 0.28520(16) 0.0239(3) Uani d . 1 1
C C2 0.3302(2) 0.12036(19) 0.37751(16) 0.0242(3) Uani d . 1 1
C C3 0.2342(2) 0.1260(2) 0.49708(16) 0.0272(4) Uani d . 1 1
H H3 0.1872 0.2233 0.5372 0.033 Uiso calc R 1 1
C C4 0.2087(2) -0.0133(2) 0.55658(17) 0.0298(4) Uani d . 1 1
C C5 0.2811(2) -0.1561(2) 0.49675(19) 0.0342(4) Uani d . 1 1
H H5 0.2626 -0.2505 0.5389 0.041 Uiso calc R 1 1
C C6 0.3782(2) -0.1647(2) 0.3793(2) 0.0341(4) Uani d . 1 1
H H6 0.4273 -0.2621 0.3395 0.041 Uiso calc R 1 1
C C7 0.3998(2) -0.0244(2) 0.32300(17) 0.0274(4) Uani d . 1 1
C C8 0.4815(2) 0.1509(2) 0.18512(17) 0.0273(4) Uani d . 1 1
C C9 0.1031(3) -0.0119(3) 0.68477(19) 0.0404(5) Uani d . 1 1
H H9A 0.1140 0.0730 0.7319 0.061 Uiso calc R 1 1
H H9B 0.1462 -0.1143 0.7316 0.061 Uiso calc R 1 1
H H9C -0.0198 0.0063 0.6744 0.061 Uiso calc R 1 1
C C10 0.5727(2) 0.1939(2) 0.06278(18) 0.0367(4) Uani d . 1 1
H H10A 0.5343 0.3093 0.0459 0.055 Uiso calc R 1 1
H H10B 0.5455 0.1426 -0.0052 0.055 Uiso calc R 1 1
H H10C 0.6989 0.1584 0.0665 0.055 Uiso calc R 1 1
C C11 0.1232(2) 0.51080(19) 0.24554(15) 0.0241(3) Uani d . 1 1
C C12 -0.0193(2) 0.4771(2) 0.31850(17) 0.0287(4) Uani d . 1 1
H H12 -0.0056 0.4149 0.3963 0.034 Uiso calc R 1 1
C C13 -0.1810(2) 0.5353(2) 0.27665(18) 0.0326(4) Uani d . 1 1
H H13 -0.2789 0.5109 0.3250 0.039 Uiso calc R 1 1
C C14 -0.2017(2) 0.6286(2) 0.16502(17) 0.0313(4) Uani d . 1 1
H H14 -0.3133 0.6683 0.1362 0.038 Uiso calc R 1 1
C C15 -0.0585(2) 0.6636(2) 0.09564(17) 0.0290(4) Uani d . 1 1
C C16 0.1054(2) 0.6038(2) 0.13328(16) 0.0277(4) Uani d . 1 1
H H16 0.2037 0.6259 0.0835 0.033 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'
Cl Cl 0.1484 0.1585 '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
O3 S1 O2 119.46(8)
O3 S1 C1 107.56(8)
O2 S1 C1 109.13(8)
O3 S1 C11 107.49(8)
O2 S1 C11 107.47(8)
C1 S1 C11 104.80(8)
C8 O1 C7 106.97(13)
C8 C1 C2 107.83(15)
C8 C1 S1 126.08(13)
C2 C1 S1 126.02(12)
C7 C2 C3 119.05(16)
C7 C2 C1 104.37(15)
C3 C2 C1 136.58(16)
C4 C3 C2 118.71(16)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C5 119.84(16)
C3 C4 C9 120.42(17)
C5 C4 C9 119.74(17)
C6 C5 C4 122.43(17)
C6 C5 H5 118.8
C4 C5 H5 118.8
C7 C6 C5 116.06(17)
C7 C6 H6 122.0
C5 C6 H6 122.0
C6 C7 O1 125.54(16)
C6 C7 C2 123.90(16)
O1 C7 C2 110.56(15)
C1 C8 O1 110.26(15)
C1 C8 C10 134.82(17)
O1 C8 C10 114.92(15)
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
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 121.36(16)
C16 C11 S1 119.09(12)
C12 C11 S1 119.55(13)
C13 C12 C11 119.07(16)
C13 C12 H12 120.5
C11 C12 H12 120.5
C12 C13 C14 120.52(16)
C12 C13 H13 119.7
C14 C13 H13 119.7
C13 C14 C15 119.29(17)
C13 C14 H14 120.4
C15 C14 H14 120.4
C16 C15 C14 121.53(16)
C16 C15 Cl1 119.16(14)
C14 C15 Cl1 119.31(14)
C15 C16 C11 118.19(16)
C15 C16 H16 120.9
C11 C16 H16 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4328(13)
S1 O2 1.4355(12)
S1 C1 1.7289(17)
S1 C11 1.7659(17)
Cl1 C15 1.7334(18)
O1 C8 1.366(2)
O1 C7 1.383(2)
C1 C8 1.357(2)
C1 C2 1.449(2)
C2 C7 1.387(2)
C2 C3 1.392(2)
C3 C4 1.386(2)
C3 H3 0.9500
C4 C5 1.401(3)
C4 C9 1.504(3)
C5 C6 1.376(3)
C5 H5 0.9500
C6 C7 1.373(3)
C6 H6 0.9500
C8 C10 1.478(2)
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 C16 1.383(2)
C11 C12 1.387(2)
C12 C13 1.377(3)
C12 H12 0.9500
C13 C14 1.380(3)
C13 H13 0.9500
C14 C15 1.381(2)
C14 H14 0.9500
C15 C16 1.376(2)
C16 H16 0.9500
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 Cg 2_556 0.98 2.73 3.663(2) 159.1
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
O3 S1 C1 C8 -151.41(16)
O2 S1 C1 C8 -20.43(19)
C11 S1 C1 C8 94.41(17)
O3 S1 C1 C2 31.89(17)
O2 S1 C1 C2 162.86(14)
C11 S1 C1 C2 -82.29(16)
C8 C1 C2 C7 0.06(19)
S1 C1 C2 C7 177.27(13)
C8 C1 C2 C3 179.0(2)
S1 C1 C2 C3 -3.8(3)
C7 C2 C3 C4 -1.3(3)
C1 C2 C3 C4 179.93(18)
C2 C3 C4 C5 0.9(3)
C2 C3 C4 C9 -178.90(17)
C3 C4 C5 C6 -0.1(3)
C9 C4 C5 C6 179.68(18)
C4 C5 C6 C7 -0.3(3)
C5 C6 C7 O1 179.85(17)
C5 C6 C7 C2 -0.1(3)
C8 O1 C7 C6 179.81(18)
C8 O1 C7 C2 -0.20(19)
C3 C2 C7 C6 0.9(3)
C1 C2 C7 C6 -179.93(17)
C3 C2 C7 O1 -179.07(15)
C1 C2 C7 O1 0.08(19)
C2 C1 C8 O1 -0.2(2)
S1 C1 C8 O1 -177.39(12)
C2 C1 C8 C10 179.7(2)
S1 C1 C8 C10 2.5(3)
C7 O1 C8 C1 0.2(2)
C7 O1 C8 C10 -179.65(15)
O3 S1 C11 C16 133.45(14)
O2 S1 C11 C16 3.68(16)
C1 S1 C11 C16 -112.32(14)
O3 S1 C11 C12 -46.03(16)
O2 S1 C11 C12 -175.80(14)
C1 S1 C11 C12 68.19(16)
C16 C11 C12 C13 1.3(3)
S1 C11 C12 C13 -179.25(14)
C11 C12 C13 C14 -1.4(3)
C12 C13 C14 C15 -0.2(3)
C13 C14 C15 C16 1.9(3)
C13 C14 C15 Cl1 -178.12(15)
C14 C15 C16 C11 -2.0(3)
Cl1 C15 C16 C11 178.02(13)
C12 C11 C16 C15 0.4(3)
S1 C11 C16 C15 -179.09(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657063
