#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227438.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227438
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Chloro-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran
;
_journal_coeditor_code           FK2023
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2350
_journal_paper_doi               10.1107/S1600536810032502
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H10 Cl F O3 S'
_chemical_formula_moiety         'C15 H10 Cl F O3 S'
_chemical_formula_sum            'C15 H10 Cl F O3 S'
_chemical_formula_weight         324.74
_chemical_name_systematic
;
5-Chloro-3-(4-fluorophenylsulfonyl)-2-methyl-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                71.161(12)
_cell_angle_beta                 79.177(11)
_cell_angle_gamma                69.108(10)
_cell_formula_units_Z            2
_cell_length_a                   7.341(2)
_cell_length_b                   9.138(2)
_cell_length_c                   11.347(3)
_cell_measurement_reflns_used    8342
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.48
_cell_volume                     670.8(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            11617
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.239
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0352
_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)+(0.0581P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2847
_reflns_number_total             3098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fk2023.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' -P 1'
_cod_database_code               2227438
_cod_database_fobs_code          2227438
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_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.24730(7) 0.91535(6) 0.18345(4) 0.04478(15) Uani d . 1 . .
S S 0.53086(5) 0.60366(4) 0.70560(3) 0.02358(12) Uani d . 1 . .
O O1 0.22044(16) 1.06562(13) 0.64622(10) 0.0287(2) Uani d . 1 . .
O O2 0.64062(16) 0.58741(14) 0.80400(10) 0.0305(3) Uani d . 1 . .
O O3 0.63148(17) 0.54999(13) 0.59840(10) 0.0316(3) Uani d . 1 . .
C C1 0.3925(2) 0.80676(17) 0.65127(13) 0.0239(3) Uani d . 1 . .
C C2 0.3246(2) 0.88838(17) 0.52755(13) 0.0233(3) Uani d . 1 . .
C C3 0.3365(2) 0.84457(19) 0.41916(14) 0.0269(3) Uani d . 1 . .
H H3 0.4057 0.7394 0.4135 0.032 Uiso calc R 1 . .
C C4 0.2404(2) 0.9649(2) 0.32022(14) 0.0295(3) Uani d . 1 . .
C C5 0.1371(2) 1.1238(2) 0.32493(15) 0.0321(3) Uani d . 1 . .
H H5 0.0756 1.2006 0.2557 0.038 Uiso calc R 1 . .
C C6 0.1260(2) 1.16749(19) 0.43212(16) 0.0306(3) Uani d . 1 . .
H H6 0.0585 1.2731 0.4374 0.037 Uiso calc R 1 . .
C C7 0.2195(2) 1.04713(18) 0.53112(14) 0.0252(3) Uani d . 1 . .
C C8 0.3252(2) 0.91825(18) 0.71784(14) 0.0266(3) Uani d . 1 . .
C C9 0.3365(3) 0.9110(2) 0.84855(15) 0.0357(4) Uani d . 1 . .
H H9A 0.4135 0.8034 0.8914 0.053 Uiso calc R 1 . .
H H9B 0.2071 0.9365 0.8898 0.053 Uiso calc R 1 . .
H H9C 0.3963 0.9886 0.8492 0.053 Uiso calc R 1 . .
C C10 0.3594(2) 0.50045(17) 0.77249(13) 0.0239(3) Uani d . 1 . .
C C11 0.2586(2) 0.46848(18) 0.69636(14) 0.0278(3) Uani d . 1 . .
H H11 0.2814 0.5015 0.6099 0.033 Uiso calc R 1 . .
C C12 0.1243(2) 0.3871(2) 0.75089(17) 0.0338(4) Uani d . 1 . .
H H12 0.0533 0.3659 0.7022 0.041 Uiso calc R 1 . .
C C13 0.0986(3) 0.3385(2) 0.87841(17) 0.0355(4) Uani d . 1 . .
C C14 0.1979(3) 0.3677(2) 0.95508(16) 0.0395(4) Uani d . 1 . .
H H14 0.1769 0.3318 1.0415 0.047 Uiso calc R 1 . .
C C15 0.3287(3) 0.4512(2) 0.90095(15) 0.0331(3) Uani d . 1 . .
H H15 0.3963 0.4745 0.9505 0.040 Uiso calc R 1 . .
F F -0.03024(18) 0.25795(15) 0.93220(12) 0.0533(3) Uani d . 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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S O2 . . 119.62(7) ?
O3 S C1 . . 107.05(7) ?
O2 S C1 . . 108.80(7) ?
O3 S C10 . . 107.97(7) ?
O2 S C10 . . 107.47(7) ?
C1 S C10 . . 105.01(7) ?
C8 O1 C7 . . 107.07(11) ?
C8 C1 C2 . . 107.35(13) ?
C8 C1 S . . 126.21(12) ?
C2 C1 S . . 126.43(11) ?
C7 C2 C3 . . 119.30(14) ?
C7 C2 C1 . . 104.34(13) ?
C3 C2 C1 . . 136.33(14) ?
C4 C3 C2 . . 116.80(14) ?
C4 C3 H3 . . 121.6 ?
C2 C3 H3 . . 121.6 ?
C3 C4 C5 . . 123.19(15) ?
C3 C4 Cl . . 118.60(13) ?
C5 C4 Cl . . 118.21(12) ?
C6 C5 C4 . . 120.04(15) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C7 C6 C5 . . 116.73(14) ?
C7 C6 H6 . . 121.6 ?
C5 C6 H6 . . 121.6 ?
O1 C7 C6 . . 125.32(14) ?
O1 C7 C2 . . 110.74(13) ?
C6 C7 C2 . . 123.93(15) ?
C1 C8 O1 . . 110.49(13) ?
C1 C8 C9 . . 134.07(15) ?
O1 C8 C9 . . 115.40(13) ?
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 . . 121.27(15) ?
C15 C10 S . . 118.69(12) ?
C11 C10 S . . 120.04(12) ?
C12 C11 C10 . . 119.11(15) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C13 C12 C11 . . 118.22(15) ?
C13 C12 H12 . . 120.9 ?
C11 C12 H12 . . 120.9 ?
F C13 C12 . . 118.62(16) ?
F C13 C14 . . 117.88(16) ?
C12 C13 C14 . . 123.50(16) ?
C15 C14 C13 . . 118.32(16) ?
C15 C14 H14 . . 120.8 ?
C13 C14 H14 . . 120.8 ?
C14 C15 C10 . . 119.55(15) ?
C14 C15 H15 . . 120.2 ?
C10 C15 H15 . . 120.2 ?
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
Cl C4 . 1.7388(17) ?
S O3 . 1.4336(11) ?
S O2 . 1.4365(11) ?
S C1 . 1.7344(15) ?
S C10 . 1.7534(16) ?
O1 C8 . 1.3619(18) ?
O1 C7 . 1.3716(19) ?
C1 C8 . 1.360(2) ?
C1 C2 . 1.448(2) ?
C2 C7 . 1.389(2) ?
C2 C3 . 1.390(2) ?
C3 C4 . 1.383(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(2) ?
C5 C6 . 1.378(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.377(2) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.480(2) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C15 . 1.380(2) ?
C10 C11 . 1.392(2) ?
C11 C12 . 1.380(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.367(3) ?
C12 H12 . 0.9300 ?
C13 F . 1.341(2) ?
C13 C14 . 1.373(3) ?
C14 C15 . 1.371(2) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
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_666 0.93 2.48 3.335(2) 152.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745800
