#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225284.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_2225284
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Chloro-2-(4-chlorophenyl)-7-methyl-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           HG2648
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o706
_journal_paper_doi               10.1107/S1600536810006823
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H12 Cl2 O2 S'
_chemical_formula_moiety         'C16 H12 Cl2 O2 S'
_chemical_formula_sum            'C16 H12 Cl2 O2 S'
_chemical_formula_weight         339.22
_chemical_name_systematic
;
5-Chloro-2-(4-chlorophenyl)-7-methyl-3-methylsulfinyl-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                72.525(2)
_cell_angle_beta                 88.846(3)
_cell_angle_gamma                70.058(2)
_cell_formula_units_Z            2
_cell_length_a                   7.538(2)
_cell_length_b                   9.734(2)
_cell_length_c                   11.277(3)
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.34
_cell_volume                     738.8(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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker HELIOS graded multilayer optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6331
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.7802
_exptl_absorpt_correction_T_min  0.7601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.4419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                2879
_reflns_number_total             3170
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2648.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2225284
_cod_database_fobs_code          2225284
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 Cl1 0.54735(6) 0.25715(5) 1.03989(4) 0.03540(12) Uani d . 1 . .
Cl Cl2 -0.06257(7) 0.78823(6) -0.05751(4) 0.04700(14) Uani d . 1 . .
S S 0.19164(6) 0.77859(5) 0.56104(4) 0.03206(12) Uani d . 1 . .
O O2 0.3263(2) 0.78670(16) 0.65093(15) 0.0479(4) Uani d . 1 . .
O O1 0.31330(15) 0.36506(12) 0.52197(10) 0.0257(2) Uani d . 1 . .
C C1 0.2500(2) 0.58258(17) 0.57346(15) 0.0256(3) Uani d . 1 . .
C C2 0.3368(2) 0.45451(18) 0.68431(15) 0.0251(3) Uani d . 1 . .
C C3 0.3874(2) 0.43701(19) 0.80827(15) 0.0276(3) Uani d . 1 . .
H H3 0.3628 0.5210 0.8373 0.033 Uiso calc R 1 . .
C C4 0.4757(2) 0.28803(19) 0.88482(15) 0.0276(3) Uani d . 1 . .
C C5 0.5149(2) 0.15889(18) 0.84399(15) 0.0277(3) Uani d . 1 . .
H H5 0.5761 0.0613 0.8998 0.033 Uiso calc R 1 . .
C C6 0.4640(2) 0.17381(18) 0.72181(15) 0.0259(3) Uani d . 1 . .
C C7 0.3749(2) 0.32444(18) 0.64609(14) 0.0240(3) Uani d . 1 . .
C C8 0.2391(2) 0.52362(17) 0.47881(15) 0.0251(3) Uani d . 1 . .
C C9 0.1655(2) 0.58997(18) 0.34785(15) 0.0260(3) Uani d . 1 . .
C C10 0.0411(2) 0.7420(2) 0.29918(16) 0.0320(4) Uani d . 1 . .
H H10 0.0039 0.8025 0.3516 0.038 Uiso calc R 1 . .
C C11 -0.0275(2) 0.8040(2) 0.17491(16) 0.0336(4) Uani d . 1 . .
H H11 -0.1079 0.9060 0.1432 0.040 Uiso calc R 1 . .
C C12 0.0253(2) 0.7123(2) 0.09853(16) 0.0321(4) Uani d . 1 . .
C C13 0.1472(2) 0.5606(2) 0.14326(17) 0.0340(4) Uani d . 1 . .
H H13 0.1808 0.5003 0.0905 0.041 Uiso calc R 1 . .
C C14 0.2181(2) 0.50046(19) 0.26736(16) 0.0295(3) Uani d . 1 . .
H H14 0.3016 0.3994 0.2978 0.035 Uiso calc R 1 . .
C C15 0.4973(3) 0.03952(19) 0.67375(17) 0.0342(4) Uani d . 1 . .
H H15A 0.3806 0.0217 0.6680 0.051 Uiso calc R 1 . .
H H15B 0.5895 -0.0505 0.7299 0.051 Uiso calc R 1 . .
H H15C 0.5430 0.0616 0.5926 0.051 Uiso calc R 1 . .
C C16 -0.0290(3) 0.8027(2) 0.63063(19) 0.0402(4) Uani d . 1 . .
H H16A -0.0092 0.7243 0.7099 0.060 Uiso calc R 1 . .
H H16B -0.1193 0.7945 0.5767 0.060 Uiso calc R 1 . .
H H16C -0.0764 0.9021 0.6424 0.060 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S C1 . . 107.20(8) ?
O2 S C16 . . 106.67(10) ?
C1 S C16 . . 97.03(8) ?
C7 O1 C8 . . 106.66(12) ?
C8 C1 C2 . . 107.57(14) ?
C8 C1 S . . 126.90(12) ?
C2 C1 S . . 125.25(12) ?
C7 C2 C3 . . 119.54(14) ?
C7 C2 C1 . . 104.68(14) ?
C3 C2 C1 . . 135.77(14) ?
C4 C3 C2 . . 116.18(14) ?
C4 C3 H3 . . 121.9 ?
C2 C3 H3 . . 121.9 ?
C3 C4 C5 . . 123.34(15) ?
C3 C4 Cl1 . . 118.85(13) ?
C5 C4 Cl1 . . 117.80(12) ?
C6 C5 C4 . . 121.32(15) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C7 C6 C5 . . 114.60(14) ?
C7 C6 C15 . . 121.71(15) ?
C5 C6 C15 . . 123.68(14) ?
O1 C7 C6 . . 124.10(14) ?
O1 C7 C2 . . 110.89(13) ?
C6 C7 C2 . . 125.01(15) ?
C1 C8 O1 . . 110.18(14) ?
C1 C8 C9 . . 134.67(15) ?
O1 C8 C9 . . 115.15(13) ?
C10 C9 C14 . . 118.35(15) ?
C10 C9 C8 . . 121.71(15) ?
C14 C9 C8 . . 119.94(14) ?
C11 C10 C9 . . 121.30(16) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 118.87(16) ?
C10 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
C11 C12 C13 . . 121.64(16) ?
C11 C12 Cl2 . . 119.29(14) ?
C13 C12 Cl2 . . 119.07(14) ?
C14 C13 C12 . . 119.06(16) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C9 . . 120.76(16) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
C6 C15 H15A . . 109.5 ?
C6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
S C16 H16A . . 109.5 ?
S C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
S 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
_geom_bond_publ_flag
Cl1 C4 . 1.7468(17) ?
Cl2 C12 . 1.7358(17) ?
S O2 . 1.4862(14) ?
S C1 . 1.7672(16) ?
S C16 . 1.797(2) ?
O1 C7 . 1.3782(19) ?
O1 C8 . 1.3794(18) ?
C1 C8 . 1.371(2) ?
C1 C2 . 1.444(2) ?
C2 C7 . 1.395(2) ?
C2 C3 . 1.401(2) ?
C3 C4 . 1.380(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.403(2) ?
C5 C6 . 1.389(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(2) ?
C6 C15 . 1.504(2) ?
C8 C9 . 1.457(2) ?
C9 C10 . 1.399(2) ?
C9 C14 . 1.402(2) ?
C10 C11 . 1.380(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.387(3) ?
C13 C14 . 1.383(2) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
_geom_hbond_publ_flag
C15 H15A O2 1_545 0.96 2.52 3.216(2) 129.5 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S C1 C8 . . . . -144.91(15) ?
C16 S C1 C8 . . . . 105.17(16) ?
O2 S C1 C2 . . . . 28.29(16) ?
C16 S C1 C2 . . . . -81.64(15) ?
C8 C1 C2 C7 . . . . 0.79(17) ?
S C1 C2 C7 . . . . -173.51(12) ?
C8 C1 C2 C3 . . . . 179.69(17) ?
S C1 C2 C3 . . . . 5.4(3) ?
C7 C2 C3 C4 . . . . 0.8(2) ?
C1 C2 C3 C4 . . . . -177.97(17) ?
C2 C3 C4 C5 . . . . 0.0(2) ?
C2 C3 C4 Cl1 . . . . 178.74(12) ?
C3 C4 C5 C6 . . . . -0.7(2) ?
Cl1 C4 C5 C6 . . . . -179.45(12) ?
C4 C5 C6 C7 . . . . 0.5(2) ?
C4 C5 C6 C15 . . . . -178.23(15) ?
C8 O1 C7 C6 . . . . -177.99(14) ?
C8 O1 C7 C2 . . . . 1.57(16) ?
C5 C6 C7 O1 . . . . 179.82(13) ?
C15 C6 C7 O1 . . . . -1.4(2) ?
C5 C6 C7 C2 . . . . 0.3(2) ?
C15 C6 C7 C2 . . . . 179.10(15) ?
C3 C2 C7 O1 . . . . 179.43(13) ?
C1 C2 C7 O1 . . . . -1.46(17) ?
C3 C2 C7 C6 . . . . -1.0(2) ?
C1 C2 C7 C6 . . . . 178.09(15) ?
C2 C1 C8 O1 . . . . 0.14(17) ?
S C1 C8 O1 . . . . 174.32(11) ?
C2 C1 C8 C9 . . . . 178.83(16) ?
S C1 C8 C9 . . . . -7.0(3) ?
C7 O1 C8 C1 . . . . -1.03(16) ?
C7 O1 C8 C9 . . . . 180.00(12) ?
C1 C8 C9 C10 . . . . -16.6(3) ?
O1 C8 C9 C10 . . . . 162.01(14) ?
C1 C8 C9 C14 . . . . 163.90(17) ?
O1 C8 C9 C14 . . . . -17.5(2) ?
C14 C9 C10 C11 . . . . -0.7(2) ?
C8 C9 C10 C11 . . . . 179.83(15) ?
C9 C10 C11 C12 . . . . 1.4(3) ?
C10 C11 C12 C13 . . . . -1.0(3) ?
C10 C11 C12 Cl2 . . . . 179.16(13) ?
C11 C12 C13 C14 . . . . -0.3(3) ?
Cl2 C12 C13 C14 . . . . 179.60(13) ?
C12 C13 C14 C9 . . . . 1.1(3) ?
C10 C9 C14 C13 . . . . -0.6(2) ?
C8 C9 C14 C13 . . . . 178.90(15) ?
