#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/03/2220354.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_2220354
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 Methyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
;
_journal_coeditor_code           SU2077
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2397
_journal_paper_doi               10.1107/S1600536808037768
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H11 Br O4 S'
_chemical_formula_moiety         'C12 H11 Br1 O4 S1'
_chemical_formula_sum            'C12 H11 Br O4 S'
_chemical_formula_weight         331.18
_chemical_melting_point_gt       405
_chemical_melting_point_lt       406
_chemical_name_systematic
;
Methyl 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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                72.5870(10)
_cell_angle_beta                 78.7160(10)
_cell_angle_gamma                69.0820(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9696(5)
_cell_length_b                   9.1146(6)
_cell_length_c                   10.3100(7)
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.08
_cell_volume                     664.17(8)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_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            3786
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.254
_exptl_absorpt_correction_T_max  0.530
_exptl_absorpt_correction_T_min  0.327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.797
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0506P)²+0.5362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2084
_reflns_number_total             2560
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2077.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C12 H11 Br1 O4 S1'
_cod_database_code               2220354
_cod_database_fobs_code          2220354
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
Br Br 0.26775(5) 0.20066(4) 0.38327(5) 0.07396(18) Uani d . 1
S S 0.73771(11) 0.63026(10) 0.03527(7) 0.0505(2) Uani d . 1
O O1 0.8367(3) 0.4636(2) 0.42105(19) 0.0450(5) Uani d . 1
O O2 0.7437(4) 0.4993(3) -0.0262(2) 0.0668(7) Uani d . 1
O O3 1.0188(3) 0.8974(3) 0.2240(3) 0.0718(7) Uani d . 1
O O4 0.7513(3) 0.8989(3) 0.1905(3) 0.0724(7) Uani d . 1
C C1 0.7429(4) 0.5435(3) 0.2117(3) 0.0422(6) Uani d . 1
C C2 0.6455(4) 0.4363(3) 0.2987(3) 0.0408(6) Uani d . 1
C C3 0.5121(4) 0.3798(3) 0.2824(3) 0.0466(7) Uani d . 1
H H3 0.4651 0.4089 0.1993 0.056 Uiso calc R 1
C C4 0.4537(4) 0.2784(4) 0.3965(4) 0.0510(7) Uani d . 1
C C5 0.5227(5) 0.2305(4) 0.5228(4) 0.0550(8) Uani d . 1
H H5 0.4796 0.1604 0.5964 0.066 Uiso calc R 1
C C6 0.6542(4) 0.2870(4) 0.5381(3) 0.0526(8) Uani d . 1
H H6 0.7023 0.2566 0.6210 0.063 Uiso calc R 1
C C7 0.7117(4) 0.3904(3) 0.4254(3) 0.0419(6) Uani d . 1
C C8 0.8535(4) 0.5552(3) 0.2893(3) 0.0413(6) Uani d . 1
C C9 0.9848(4) 0.6447(4) 0.2609(3) 0.0473(7) Uani d . 1
H H9A 1.0742 0.6117 0.1877 0.057 Uiso calc R 1
H H9B 1.0470 0.6145 0.3416 0.057 Uiso calc R 1
C C10 0.9012(4) 0.8259(4) 0.2215(3) 0.0483(7) Uani d . 1
C C11 0.5088(5) 0.7628(4) 0.0366(4) 0.0637(9) Uani d . 1
H H11A 0.4834 0.8234 -0.0551 0.096 Uiso calc R 1
H H11B 0.4918 0.8363 0.0916 0.096 Uiso calc R 1
H H11C 0.4285 0.6997 0.0740 0.096 Uiso calc R 1
C C12 0.9545(7) 1.0738(5) 0.1880(7) 0.1065(18) Uani d . 1
H H12A 1.0493 1.1133 0.1927 0.160 Uiso calc R 1
H H12B 0.8527 1.1114 0.2506 0.160 Uiso calc R 1
H H12C 0.9191 1.1131 0.0968 0.160 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
O2 S C1 106.07(14)
O2 S C11 106.21(17)
C1 S C11 98.55(16)
C7 O1 C8 106.4(2)
C10 O3 C12 116.0(3)
C8 C1 C2 107.2(3)
C8 C1 S 124.7(2)
C2 C1 S 127.9(2)
C3 C2 C7 120.0(3)
C3 C2 C1 135.6(3)
C7 C2 C1 104.4(2)
C4 C3 C2 116.2(3)
C4 C3 H3 121.9
C2 C3 H3 121.9
C3 C4 C5 123.5(3)
C3 C4 Br 118.6(3)
C5 C4 Br 117.9(2)
C6 C5 C4 119.9(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 117.1(3)
C5 C6 H6 121.5
C7 C6 H6 121.5
O1 C7 C6 125.9(3)
O1 C7 C2 110.9(2)
C6 C7 C2 123.2(3)
C1 C8 O1 111.1(2)
C1 C8 C9 133.3(3)
O1 C8 C9 115.6(2)
C8 C9 C10 114.0(2)
C8 C9 H9A 108.8
C10 C9 H9A 108.8
C8 C9 H9B 108.8
C10 C9 H9B 108.8
H9A C9 H9B 107.7
O4 C10 O3 123.4(3)
O4 C10 C9 126.2(3)
O3 C10 C9 110.4(3)
S C11 H11A 109.5
S C11 H11B 109.5
H11A C11 H11B 109.5
S C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O3 C12 H12A 109.5
O3 C12 H12B 109.5
H12A C12 H12B 109.5
O3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C4 1.898(3)
S O2 1.493(3)
S C1 1.755(3)
S C11 1.793(4)
O1 C7 1.370(3)
O1 C8 1.375(3)
O3 C10 1.327(4)
O3 C12 1.454(5)
O4 C10 1.195(4)
C1 C8 1.350(4)
C1 C2 1.451(4)
C2 C3 1.391(4)
C2 C7 1.395(4)
C3 C4 1.377(4)
C3 H3 0.9300
C4 C5 1.400(5)
C5 C6 1.374(5)
C5 H5 0.9300
C6 C7 1.376(4)
C6 H6 0.9300
C8 C9 1.481(4)
C9 C10 1.501(4)
C9 H9A 0.9700
C9 H9B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 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
C3 H3 O2 2_665 0.93 2.43 3.334(4) 163
C9 H9B O1 2_766 0.97 2.59 3.555(3) 171
C9 H9A O2 2_765 0.97 2.22 3.177(4) 169
C12 H12B Cg 1_565 0.96 2.99 3.903(4) 159
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
O2 S C1 C8 131.5(3)
C11 S C1 C8 -118.8(3)
O2 S C1 C2 -42.4(3)
C11 S C1 C2 67.3(3)
C8 C1 C2 C3 177.9(3)
S C1 C2 C3 -7.3(5)
C8 C1 C2 C7 -0.7(3)
S C1 C2 C7 174.1(2)
C7 C2 C3 C4 -0.3(4)
C1 C2 C3 C4 -178.8(3)
C2 C3 C4 C5 -0.8(4)
C2 C3 C4 Br 178.5(2)
C3 C4 C5 C6 0.9(5)
Br C4 C5 C6 -178.4(2)
C4 C5 C6 C7 0.1(5)
C8 O1 C7 C6 179.7(3)
C8 O1 C7 C2 -1.1(3)
C5 C6 C7 O1 177.8(3)
C5 C6 C7 C2 -1.3(5)
C3 C2 C7 O1 -177.8(2)
C1 C2 C7 O1 1.1(3)
C3 C2 C7 C6 1.4(4)
C1 C2 C7 C6 -179.7(3)
C2 C1 C8 O1 0.1(3)
S C1 C8 O1 -174.9(2)
C2 C1 C8 C9 -179.8(3)
S C1 C8 C9 5.1(5)
C7 O1 C8 C1 0.6(3)
C7 O1 C8 C9 -179.5(2)
C1 C8 C9 C10 63.6(4)
O1 C8 C9 C10 -116.3(3)
C12 O3 C10 O4 0.8(5)
C12 O3 C10 C9 -179.9(4)
C8 C9 C10 O4 -12.9(5)
C8 C9 C10 O3 167.7(3)
