#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221233.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_2221233
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 Propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
;
_journal_coeditor_code           ZL2167
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o520
_journal_paper_doi               10.1107/S160053680900453X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H15 Br O4 S'
_chemical_formula_moiety         'C14 H15 Br O4 S'
_chemical_formula_sum            'C14 H15 Br O4 S'
_chemical_formula_weight         359.23
_chemical_name_systematic
;
Propyl 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                72.3580(10)
_cell_angle_beta                 81.2000(10)
_cell_angle_gamma                65.4430(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4538(6)
_cell_length_b                   9.8823(7)
_cell_length_c                   10.3231(7)
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.65
_cell_volume                     747.16(9)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3932
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  0.556
_exptl_absorpt_correction_T_min  0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.377
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0335
_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)+(0.0598P)²+0.3564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2359
_reflns_number_total             2593
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2167.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -p_1
_cod_database_code               2221233
_cod_database_fobs_code          2221233
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 0.68856(4) 0.78591(4) 0.61232(4) 0.06138(16) Uani d . 1 . .
S S 0.26099(9) 0.40306(8) 0.96326(6) 0.04277(19) Uani d . 1 . .
O O1 0.1656(2) 0.5416(2) 0.57292(17) 0.0389(4) Uani d . 1 . .
O O2 0.0410(3) 0.1435(2) 0.7276(3) 0.0651(6) Uani d . 1 . .
O O3 0.2856(3) 0.1366(3) 0.7909(3) 0.0628(6) Uani d . 1 . .
O O4 0.2583(3) 0.5257(3) 1.0205(2) 0.0565(5) Uani d . 1 . .
C C1 0.2557(3) 0.4773(3) 0.7850(2) 0.0355(5) Uani d . 1 . .
C C2 0.3457(3) 0.5694(3) 0.6968(2) 0.0345(5) Uani d . 1 . .
C C3 0.4701(3) 0.6215(3) 0.7124(3) 0.0390(6) Uani d . 1 . .
H H3 0.5166 0.5970 0.7965 0.047 Uiso calc R 1 . .
C C4 0.5206(3) 0.7106(3) 0.5974(3) 0.0411(6) Uani d . 1 . .
C C5 0.4525(4) 0.7510(3) 0.4691(3) 0.0448(6) Uani d . 1 . .
H H5 0.4882 0.8144 0.3949 0.054 Uiso calc R 1 . .
C C6 0.3327(3) 0.6968(3) 0.4533(3) 0.0421(6) Uani d . 1 . .
H H6 0.2877 0.7199 0.3689 0.051 Uiso calc R 1 . .
C C7 0.2826(3) 0.6069(3) 0.5677(3) 0.0367(5) Uani d . 1 . .
C C8 0.1513(3) 0.4645(3) 0.7068(3) 0.0368(5) Uani d . 1 . .
C C9 0.0363(3) 0.3784(3) 0.7351(3) 0.0408(6) Uani d . 1 . .
H H9A -0.0412 0.4178 0.6600 0.049 Uiso calc R 1 . .
H H9B -0.0347 0.3956 0.8164 0.049 Uiso calc R 1 . .
C C10 0.1380(4) 0.2072(3) 0.7546(3) 0.0448(6) Uani d . 1 . .
C C11 0.1221(5) -0.0227(4) 0.7402(6) 0.0860(14) Uani d . 1 . .
H H11A 0.1843 -0.0769 0.8242 0.103 Uiso calc R 1 . .
H H11B 0.2040 -0.0434 0.6648 0.103 Uiso calc R 1 . .
C C12 -0.0195(6) -0.0757(5) 0.7394(6) 0.0900(14) Uani d . 1 . .
H H12A -0.0800 -0.0196 0.6548 0.108 Uiso calc R 1 . .
H H12B 0.0329 -0.1842 0.7418 0.108 Uiso calc R 1 . .
C C13 -0.1468(9) -0.0548(7) 0.8527(6) 0.122(2) Uani d . 1 . .
H H13A -0.2019 0.0527 0.8501 0.147 Uiso calc R 1 . .
H H13B -0.0889 -0.1122 0.9372 0.147 Uiso calc R 1 . .
H H13C -0.2332 -0.0913 0.8452 0.147 Uiso calc R 1 . .
C C14 0.4798(4) 0.2618(4) 0.9755(3) 0.0575(8) Uani d . 1 . .
H H14A 0.5592 0.3128 0.9465 0.086 Uiso calc R 1 . .
H H14B 0.4965 0.1959 0.9185 0.086 Uiso calc R 1 . .
H H14C 0.5011 0.2010 1.0681 0.086 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'
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 . . 107.01(13) ?
O4 S C14 . . 106.32(14) ?
C1 S C14 . . 98.46(14) ?
C8 O1 C7 . . 106.53(19) ?
C10 O2 C11 . . 117.2(2) ?
C8 C1 C2 . . 107.4(2) ?
C8 C1 S . . 123.4(2) ?
C2 C1 S . . 129.00(19) ?
C3 C2 C7 . . 119.3(2) ?
C3 C2 C1 . . 136.1(2) ?
C7 C2 C1 . . 104.6(2) ?
C4 C3 C2 . . 116.8(2) ?
C4 C3 H3 . . 121.6 ?
C2 C3 H3 . . 121.6 ?
C3 C4 C5 . . 123.3(3) ?
C3 C4 Br . . 118.7(2) ?
C5 C4 Br . . 117.9(2) ?
C6 C5 C4 . . 119.8(3) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C7 C6 C5 . . 117.1(2) ?
C7 C6 H6 . . 121.5 ?
C5 C6 H6 . . 121.5 ?
O1 C7 C6 . . 125.9(2) ?
O1 C7 C2 . . 110.5(2) ?
C6 C7 C2 . . 123.6(2) ?
C1 C8 O1 . . 111.0(2) ?
C1 C8 C9 . . 133.2(2) ?
O1 C8 C9 . . 115.7(2) ?
C8 C9 C10 . . 112.2(2) ?
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 . . 124.0(3) ?
O3 C10 C9 . . 125.6(3) ?
O2 C10 C9 . . 110.4(2) ?
O2 C11 C12 . . 107.7(3) ?
O2 C11 H11A . . 110.2 ?
C12 C11 H11A . . 110.2 ?
O2 C11 H11B . . 110.2 ?
C12 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
C13 C12 C11 . . 114.4(5) ?
C13 C12 H12A . . 108.7 ?
C11 C12 H12A . . 108.7 ?
C13 C12 H12B . . 108.7 ?
C11 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
S C14 H14A . . 109.5 ?
S C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
S C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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 . 1.899(3) ?
S O4 . 1.492(2) ?
S C1 . 1.763(3) ?
S C14 . 1.790(3) ?
O1 C8 . 1.375(3) ?
O1 C7 . 1.375(3) ?
O2 C10 . 1.323(4) ?
O2 C11 . 1.465(4) ?
O3 C10 . 1.202(4) ?
C1 C8 . 1.349(4) ?
C1 C2 . 1.448(4) ?
C2 C3 . 1.396(4) ?
C2 C7 . 1.397(3) ?
C3 C4 . 1.376(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.402(4) ?
C5 C6 . 1.377(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.374(4) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.486(4) ?
C9 C10 . 1.509(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C12 . 1.494(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.465(7) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 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
C11 H11B Cg1 1_545 0.97 3.02 3.720(3) 130.0
C12 H12B Cg2 1_545 0.97 2.90 3.826(3) 161.1
C3 H3 O4 2_667 0.93 2.54 3.424(3) 158.7
C5 H5 O3 2_666 0.93 2.58 3.430(4) 152.1
C9 H9B O4 2_567 0.97 2.37 3.321(3) 167.1
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_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 . . . . -134.5(2) ?
C14 S C1 C8 . . . . 115.5(2) ?
O4 S C1 C2 . . . . 40.5(3) ?
C14 S C1 C2 . . . . -69.5(3) ?
C8 C1 C2 C3 . . . . -178.6(3) ?
S C1 C2 C3 . . . . 5.7(4) ?
C8 C1 C2 C7 . . . . 0.7(3) ?
S C1 C2 C7 . . . . -174.95(19) ?
C7 C2 C3 C4 . . . . 1.3(4) ?
C1 C2 C3 C4 . . . . -179.5(3) ?
C2 C3 C4 C5 . . . . 0.6(4) ?
C2 C3 C4 Br . . . . 179.65(18) ?
C3 C4 C5 C6 . . . . -2.0(4) ?
Br C4 C5 C6 . . . . 178.9(2) ?
C4 C5 C6 C7 . . . . 1.5(4) ?
C8 O1 C7 C6 . . . . -178.8(2) ?
C8 O1 C7 C2 . . . . 1.2(3) ?
C5 C6 C7 O1 . . . . -179.7(2) ?
C5 C6 C7 C2 . . . . 0.3(4) ?
C3 C2 C7 O1 . . . . 178.3(2) ?
C1 C2 C7 O1 . . . . -1.2(3) ?
C3 C2 C7 C6 . . . . -1.8(4) ?
C1 C2 C7 C6 . . . . 178.8(2) ?
C2 C1 C8 O1 . . . . 0.0(3) ?
S C1 C8 O1 . . . . 175.96(17) ?
C2 C1 C8 C9 . . . . 175.7(3) ?
S C1 C8 C9 . . . . -8.3(4) ?
C7 O1 C8 C1 . . . . -0.7(3) ?
C7 O1 C8 C9 . . . . -177.3(2) ?
C1 C8 C9 C10 . . . . -73.6(4) ?
O1 C8 C9 C10 . . . . 102.0(3) ?
C11 O2 C10 O3 . . . . -1.5(5) ?
C11 O2 C10 C9 . . . . 179.2(3) ?
C8 C9 C10 O3 . . . . 24.7(4) ?
C8 C9 C10 O2 . . . . -156.0(2) ?
C10 O2 C11 C12 . . . . 166.2(4) ?
O2 C11 C12 C13 . . . . -62.0(6) ?
