#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221802.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_2221802
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-Chloroethyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
;
_journal_coeditor_code           SJ2602
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1025
_journal_paper_doi               10.1107/S1600536809012847
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H12 Br Cl O4 S'
_chemical_formula_moiety         'C13 H12 Br Cl O4 S'
_chemical_formula_sum            'C13 H12 Br Cl O4 S'
_chemical_formula_weight         379.65
_chemical_name_systematic
;
2-Chloroethyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
;
_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                71.095(3)
_cell_angle_beta                 80.331(3)
_cell_angle_gamma                65.012(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4950(10)
_cell_length_b                   9.882(2)
_cell_length_c                   10.277(2)
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.65
_cell_volume                     739.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      298(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0452
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5479
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.110
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.805
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max_lt       0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.054P)²+1.6319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1972
_reflns_number_total             2575
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2602.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_original_sg_symbol_Hall     '-p 1'
_cod_database_code               2221802
_cod_database_fobs_code          2221802
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
Br Br 0.68390(9) 0.78885(8) 0.10766(7) 0.0571(3) Uani d . 1 . .
Cl ClA -0.1810(4) -0.0480(3) 0.3580(3) 0.0928(12) Uani d PDU 0.764(6) A 1
Cl ClB -0.0308(13) -0.0729(11) 0.1579(12) 0.0928(12) Uani d PDU 0.24 A 2
S S 0.25778(18) 0.40156(16) 0.46589(13) 0.0391(4) Uani d . 1 . .
O O1 0.1648(4) 0.5435(4) 0.0705(3) 0.0355(8) Uani d . 1 . .
O O2 0.0404(6) 0.1375(5) 0.2446(7) 0.0824(18) Uani d D 1 . .
O O3 0.2843(6) 0.1340(5) 0.2991(5) 0.0622(12) Uani d . 1 . .
O O4 0.2572(6) 0.5265(5) 0.5185(4) 0.0537(11) Uani d . 1 . .
C C1 0.2533(6) 0.4767(6) 0.2849(5) 0.0313(11) Uani d . 1 . .
C C2 0.3429(6) 0.5699(5) 0.1946(5) 0.0287(11) Uani d . 1 . .
C C3 0.4664(7) 0.6219(6) 0.2093(6) 0.0362(12) Uani d . 1 . .
H H3 0.5126 0.5960 0.2941 0.043 Uiso calc R 1 . .
C C4 0.5167(7) 0.7138(6) 0.0920(6) 0.0379(13) Uani d . 1 . .
C C5 0.4497(7) 0.7563(6) -0.0359(6) 0.0395(13) Uani d . 1 . .
H H5 0.4849 0.8216 -0.1110 0.047 Uiso calc R 1 . .
C C6 0.3306(7) 0.7020(6) -0.0522(6) 0.0382(13) Uani d . 1 . .
H H6 0.2860 0.7271 -0.1375 0.046 Uiso calc R 1 . .
C C7 0.2815(6) 0.6090(6) 0.0641(5) 0.0326(12) Uani d . 1 . .
C C8 0.1505(7) 0.4640(6) 0.2065(5) 0.0328(11) Uani d . 1 A .
C C9 0.0354(7) 0.3767(6) 0.2371(6) 0.0377(13) Uani d . 1 . .
H H9A -0.0383 0.4141 0.1598 0.045 Uiso calc R 1 A .
H H9B -0.0392 0.3968 0.3170 0.045 Uiso calc R 1 . .
C C10 0.1380(8) 0.2042(7) 0.2639(6) 0.0446(14) Uani d . 1 A .
C C11A 0.1269(13) -0.0271(11) 0.2556(12) 0.069(3) Uani d PDU 0.764(6) A 1
H H11A 0.2031 -0.0798 0.3329 0.083 Uiso calc PR 0.764(6) A 1
H H11B 0.1968 -0.0422 0.1725 0.083 Uiso calc PR 0.764(6) A 1
C C12A -0.004(3) -0.092(3) 0.275(2) 0.162(6) Uani d PDU 0.764(6) A 1
H H12A 0.0570 -0.2031 0.3143 0.195 Uiso calc PR 0.764(6) A 1
H H12B -0.0332 -0.0779 0.1832 0.195 Uiso calc PR 0.764(6) A 1
C C11B 0.107(4) -0.044(3) 0.343(4) 0.069(3) Uani d PDU 0.24 A 2
H H11C 0.2242 -0.1045 0.3153 0.083 Uiso calc PR 0.236(6) A 2
H H11D 0.1055 -0.0480 0.4385 0.083 Uiso calc PR 0.236(6) A 2
C C12B -0.013(10) -0.105(10) 0.324(4) 0.162(6) Uani d PDU 0.24 A 2
H H12C -0.1259 -0.0542 0.3648 0.195 Uiso calc PR 0.236(6) A 2
H H12D 0.0286 -0.2156 0.3696 0.195 Uiso calc PR 0.236(6) A 2
C C13 0.4757(8) 0.2580(7) 0.4793(7) 0.0566(17) Uani d . 1 . .
H H13A 0.5553 0.3084 0.4440 0.085 Uiso calc R 1 . .
H H13B 0.4904 0.1885 0.4269 0.085 Uiso calc R 1 . .
H H13C 0.4983 0.2002 0.5740 0.085 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 S C1 . . 105.9(2) ?
O4 S C13 . . 106.1(3) ?
C1 S C13 . . 98.5(3) ?
C8 O1 C7 . . 106.5(4) ?
C10 O2 C11A . . 116.1(6) ?
C10 O2 C11B . . 109.4(13) ?
C11A O2 C11B . . 31.3(12) ?
C8 C1 C2 . . 107.4(4) ?
C8 C1 S . . 123.8(4) ?
C2 C1 S . . 128.7(4) ?
C3 C2 C7 . . 119.1(5) ?
C3 C2 C1 . . 136.0(5) ?
C7 C2 C1 . . 104.9(4) ?
C4 C3 C2 . . 116.8(5) ?
C4 C3 H3 . . 121.6 ?
C2 C3 H3 . . 121.6 ?
C3 C4 C5 . . 123.3(5) ?
C3 C4 Br . . 118.2(4) ?
C5 C4 Br . . 118.4(4) ?
C6 C5 C4 . . 120.3(5) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C7 C6 C5 . . 116.6(5) ?
C7 C6 H6 . . 121.7 ?
C5 C6 H6 . . 121.7 ?
C6 C7 O1 . . 126.0(5) ?
C6 C7 C2 . . 123.8(5) ?
O1 C7 C2 . . 110.3(4) ?
C1 C8 O1 . . 110.9(4) ?
C1 C8 C9 . . 133.1(5) ?
O1 C8 C9 . . 115.9(4) ?
C8 C9 C10 . . 112.0(4) ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O3 C10 O2 . . 123.5(5) ?
O3 C10 C9 . . 126.4(5) ?
O2 C10 C9 . . 110.0(5) ?
O2 C11A C12A . . 108.9(13) ?
O2 C11A H11A . . 109.9 ?
C12A C11A H11A . . 109.9 ?
O2 C11A H11B . . 109.9 ?
C12A C11A H11B . . 109.9 ?
H11A C11A H11B . . 108.3 ?
C11A C12A ClA . . 128.4(16) ?
C11A C12A H12A . . 105.2 ?
ClA C12A H12A . . 105.2 ?
C11A C12A H12B . . 105.2 ?
ClA C12A H12B . . 105.2 ?
H12A C12A H12B . . 105.9 ?
C12B C11B O2 . . 106(4) ?
C12B C11B H11C . . 110.5 ?
O2 C11B H11C . . 110.5 ?
C12B C11B H11D . . 110.5 ?
O2 C11B H11D . . 110.5 ?
H11C C11B H11D . . 108.7 ?
C11B C12B ClB . . 110(3) ?
C11B C12B H12C . . 109.7 ?
ClB C12B H12C . . 109.7 ?
C11B C12B H12D . . 109.7 ?
ClB C12B H12D . . 109.7 ?
H12C C12B H12D . . 108.2 ?
S C13 H13A . . 109.5 ?
S C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
S C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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
Br C4 . 1.907(5) ?
ClA C12A . 1.559(19) ?
ClB C12B . 1.65(3) ?
S O4 . 1.498(4) ?
S C1 . 1.766(5) ?
S C13 . 1.788(6) ?
O1 C8 . 1.377(6) ?
O1 C7 . 1.378(6) ?
O2 C10 . 1.328(7) ?
O2 C11A . 1.448(9) ?
O2 C11B . 1.65(2) ?
O3 C10 . 1.190(7) ?
C1 C8 . 1.350(7) ?
C1 C2 . 1.445(7) ?
C2 C3 . 1.395(7) ?
C2 C7 . 1.396(7) ?
C3 C4 . 1.380(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.385(8) ?
C5 C6 . 1.383(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.375(7) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.494(7) ?
C9 C10 . 1.505(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11A C12A . 1.459(15) ?
C11A H11A . 0.9700 ?
C11A H11B . 0.9700 ?
C12A H12A . 0.9700 ?
C12A H12B . 0.9700 ?
C11B C12B . 1.45(2) ?
C11B H11C . 0.9700 ?
C11B H11D . 0.9700 ?
C12B H12C . 0.9700 ?
C12B H12D . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 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
C11A H11B Cg 1_545 0.97 3.07 3.779(7) 130.8
C3 H3 O4 2_666 0.93 2.60 3.483(7) 159.0
C5 H5 O3 2_665 0.93 2.58 3.423(7) 150.3
C9 H9A O1 2_565 0.97 2.60 3.545(6) 164.5
C9 H9B O4 2_566 0.97 2.34 3.294(7) 169.8
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
O4 S C1 C8 . . . . -135.7(5) ?
C13 S C1 C8 . . . . 114.8(5) ?
O4 S C1 C2 . . . . 39.3(5) ?
C13 S C1 C2 . . . . -70.2(5) ?
C8 C1 C2 C3 . . . . -178.3(6) ?
S C1 C2 C3 . . . . 6.0(9) ?
C8 C1 C2 C7 . . . . 0.9(5) ?
S C1 C2 C7 . . . . -174.7(4) ?
C7 C2 C3 C4 . . . . 1.7(7) ?
C1 C2 C3 C4 . . . . -179.1(5) ?
C2 C3 C4 C5 . . . . 0.7(8) ?
C2 C3 C4 Br . . . . 179.5(4) ?
C3 C4 C5 C6 . . . . -2.4(8) ?
Br C4 C5 C6 . . . . 178.8(4) ?
C4 C5 C6 C7 . . . . 1.5(8) ?
C5 C6 C7 O1 . . . . 179.8(5) ?
C5 C6 C7 C2 . . . . 0.9(8) ?
C8 O1 C7 C6 . . . . -178.2(5) ?
C8 O1 C7 C2 . . . . 0.8(5) ?
C3 C2 C7 C6 . . . . -2.6(8) ?
C1 C2 C7 C6 . . . . 178.0(5) ?
C3 C2 C7 O1 . . . . 178.4(4) ?
C1 C2 C7 O1 . . . . -1.1(5) ?
C2 C1 C8 O1 . . . . -0.5(6) ?
S C1 C8 O1 . . . . 175.4(3) ?
C2 C1 C8 C9 . . . . 176.0(5) ?
S C1 C8 C9 . . . . -8.1(9) ?
C7 O1 C8 C1 . . . . -0.1(5) ?
C7 O1 C8 C9 . . . . -177.3(4) ?
C1 C8 C9 C10 . . . . -71.8(8) ?
O1 C8 C9 C10 . . . . 104.6(5) ?
C11A O2 C10 O3 . . . . -5.9(11) ?
C11B O2 C10 O3 . . . . 27.3(16) ?
C11A O2 C10 C9 . . . . 175.0(7) ?
C11B O2 C10 C9 . . . . -151.7(14) ?
C8 C9 C10 O3 . . . . 21.9(9) ?
C8 C9 C10 O2 . . . . -159.1(5) ?
C10 O2 C11A C12A . . . . 162.3(11) ?
C11B O2 C11A C12A . . . . 78(3) ?
O2 C11A C12A ClA . . . . -36(3) ?
C10 O2 C11B C12B . . . . 176(3) ?
C11A O2 C11B C12B . . . . -76(4) ?
O2 C11B C12B ClB . . . . 52(6) ?
