#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220922.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_2220922
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 Butyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
;
_journal_coeditor_code           TK2347
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o265
_journal_paper_doi               10.1107/S1600536808043985
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H17 Br O4 S'
_chemical_formula_moiety         'C15 H17 Br O4 S'
_chemical_formula_sum            'C15 H17 Br O4 S'
_chemical_formula_weight         373.26
_chemical_name_systematic
;
Butyl 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                97.503(2)
_cell_angle_beta                 99.711(2)
_cell_angle_gamma                108.678(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4200(10)
_cell_length_b                   10.2550(10)
_cell_length_c                   10.3060(10)
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.6
_cell_volume                     814.55(15)
_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  0.017
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6560
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.1
_exptl_absorpt_coefficient_mu    2.663
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.17
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.033
_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)+(0.0442P)²+0.2004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.084
_refine_ls_wR_factor_ref         0.089
_reflns_number_gt                2645
_reflns_number_total             3179
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2347.cif
_cod_data_source_block           I
_cod_database_code               2220922
_cod_database_fobs_code          2220922
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 -0.42599(4) 0.24082(3) 0.12584(3) 0.06775(14) Uani d . 1 . .
S S 0.32177(9) 0.58854(7) 0.45871(6) 0.04988(17) Uani d . 1 . .
O O1 0.3033(2) 0.46045(17) 0.07725(15) 0.0442(4) Uani d . 1 . .
O O2 0.7594(3) 0.8276(2) 0.2120(2) 0.0686(6) Uani d . 1 . .
O O3 0.5174(3) 0.8291(2) 0.2711(2) 0.0721(6) Uani d . 1 . .
O O4 0.2197(3) 0.4784(2) 0.52321(18) 0.0618(5) Uani d . 1 . .
C C1 0.2665(3) 0.5195(2) 0.2849(2) 0.0413(5) Uani d . 1 . .
C C2 0.0997(3) 0.4347(2) 0.2012(2) 0.0401(5) Uani d . 1 . .
C C3 -0.0682(3) 0.3882(3) 0.2186(2) 0.0447(5) Uani d . 1 . .
H H3 -0.0941 0.4108 0.3010 0.054 Uiso calc R 1 . .
C C4 -0.1944(3) 0.3070(3) 0.1078(3) 0.0472(6) Uani d . 1 . .
C C5 -0.1604(4) 0.2716(3) -0.0175(3) 0.0509(6) Uani d . 1 . .
H H5 -0.2500 0.2159 -0.0889 0.061 Uiso calc R 1 . .
C C6 0.0052(3) 0.3188(3) -0.0354(2) 0.0478(6) Uani d . 1 . .
H H6 0.0307 0.2966 -0.1181 0.057 Uiso calc R 1 . .
C C7 0.1318(3) 0.4008(2) 0.0749(2) 0.0414(5) Uani d . 1 . .
C C8 0.3827(3) 0.5320(2) 0.2067(2) 0.0417(5) Uani d . 1 A .
C C9 0.5701(3) 0.6117(3) 0.2310(3) 0.0460(6) Uani d . 1 . .
H H9A 0.6150 0.5767 0.1586 0.055 Uiso calc R 1 A .
H H9B 0.6281 0.5959 0.3140 0.055 Uiso calc R 1 . .
C C10 0.6090(3) 0.7675(3) 0.2403(3) 0.0506(6) Uani d . 1 A .
C C11A 0.8140(8) 0.9810(14) 0.2252(11) 0.087(3) Uani d PDU 0.720(8) A 1
H H11A 0.8117 1.0245 0.3139 0.104 Uiso calc PR 0.720(8) A 1
H H11B 0.7375 1.0053 0.1590 0.104 Uiso calc PR 0.720(8) A 1
C C12A 0.9913(6) 1.0302(6) 0.2033(6) 0.0749(16) Uani d PDU 0.720(8) A 1
H H12A 1.0207 1.1232 0.1821 0.090 Uiso calc PR 0.720(8) A 1
H H12B 1.0036 0.9664 0.1307 0.090 Uiso calc PR 0.720(8) A 1
C C13A 1.1021(6) 1.0324(8) 0.3331(7) 0.098(2) Uani d PDU 0.720(8) A 1
H H13A 1.0712 1.0833 0.4050 0.117 Uiso calc PR 0.720(8) A 1
H H13B 1.0766 0.9366 0.3464 0.117 Uiso calc PR 0.720(8) A 1
C C14A 1.2899(7) 1.0964(9) 0.3450(10) 0.134(3) Uani d PDU 0.720(8) A 1
H H14A 1.3499 1.0967 0.4330 0.202 Uiso calc PR 0.720(8) A 1
H H14B 1.3173 1.1911 0.3309 0.202 Uiso calc PR 0.720(8) A 1
H H14C 1.3243 1.0429 0.2788 0.202 Uiso calc PR 0.720(8) A 1
C C11B 0.806(2) 0.973(3) 0.183(2) 0.070(5) Uani d PDU 0.280(8) A 2
H H11C 0.7231 1.0153 0.2025 0.084 Uiso calc PR 0.280(8) A 2
H H11D 0.8138 0.9721 0.0903 0.084 Uiso calc PR 0.280(8) A 2
C C12B 0.9768(19) 1.049(2) 0.275(3) 0.127(7) Uani d PDU 0.280(8) A 2
H H12C 0.9614 1.0361 0.3645 0.153 Uiso calc PR 0.280(8) A 2
H H12D 1.0003 1.1475 0.2746 0.153 Uiso calc PR 0.280(8) A 2
C C13B 1.1377(19) 1.0231(18) 0.2628(16) 0.087(5) Uani d PDU 0.280(8) A 2
H H13C 1.1320 0.9270 0.2622 0.105 Uiso calc PR 0.280(8) A 2
H H13D 1.1884 1.0601 0.1915 0.105 Uiso calc PR 0.280(8) A 2
C C14B 1.207(3) 1.117(2) 0.3964(16) 0.124(6) Uani d PDU 0.280(8) A 2
H H14D 1.3305 1.1547 0.4133 0.186 Uiso calc PR 0.280(8) A 2
H H14E 1.1729 1.0655 0.4643 0.186 Uiso calc PR 0.280(8) A 2
H H14F 1.1634 1.1931 0.3985 0.186 Uiso calc PR 0.280(8) A 2
C C15 0.2192(5) 0.7173(3) 0.4576(3) 0.0679(8) Uani d . 1 . .
H H15A 0.0971 0.6710 0.4266 0.102 Uiso calc R 1 . .
H H15B 0.2615 0.7788 0.3987 0.102 Uiso calc R 1 . .
H H15C 0.2442 0.7710 0.5468 0.102 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 . . 106.92(12) ?
O4 S C15 . . 105.78(14) ?
C1 S C15 . . 98.46(13) ?
C7 O1 C8 . . 106.62(17) ?
C10 O2 C11A . . 115.2(3) ?
C10 O2 C11B . . 120.0(10) ?
C11A O2 C11B . . 16.2(11) ?
C8 C1 C2 . . 107.4(2) ?
C8 C1 S . . 123.77(19) ?
C2 C1 S . . 128.70(18) ?
C3 C2 C7 . . 119.5(2) ?
C3 C2 C1 . . 135.8(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 . . 123.2(2) ?
C3 C4 Br . . 118.51(19) ?
C5 C4 Br . . 118.29(19) ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 116.8(2) ?
C5 C6 H6 . . 121.6 ?
C7 C6 H6 . . 121.6 ?
O1 C7 C6 . . 125.9(2) ?
O1 C7 C2 . . 110.7(2) ?
C6 C7 C2 . . 123.5(2) ?
C1 C8 O1 . . 110.7(2) ?
C1 C8 C9 . . 133.3(2) ?
O1 C8 C9 . . 115.9(2) ?
C8 C9 C10 . . 112.3(2) ?
C8 C9 H9A . . 109.1 ?
C10 C9 H9A . . 109.1 ?
C8 C9 H9B . . 109.1 ?
C10 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
O3 C10 O2 . . 124.3(3) ?
O3 C10 C9 . . 124.9(3) ?
O2 C10 C9 . . 110.8(2) ?
O2 C11A C12A . . 107.2(8) ?
O2 C11A H11A . . 110.3 ?
C12A C11A H11A . . 110.3 ?
O2 C11A H11B . . 110.3 ?
C12A C11A H11B . . 110.3 ?
H11A C11A H11B . . 108.5 ?
C11A C12A C13A . . 104.5(6) ?
C11A C12A H12A . . 110.8 ?
C13A C12A H12A . . 110.8 ?
C11A C12A H12B . . 110.8 ?
C13A C12A H12B . . 110.8 ?
H12A C12A H12B . . 108.9 ?
C14A C13A C12A . . 115.7(6) ?
C14A C13A H13A . . 108.4 ?
C12A C13A H13A . . 108.4 ?
C14A C13A H13B . . 108.4 ?
C12A C13A H13B . . 108.4 ?
H13A C13A H13B . . 107.4 ?
C13A C14A H14A . . 109.5 ?
C13A C14A H14B . . 109.5 ?
H14A C14A H14B . . 109.5 ?
C13A C14A H14C . . 109.5 ?
H14A C14A H14C . . 109.5 ?
H14B C14A H14C . . 109.5 ?
O2 C11B C12B . . 104(2) ?
O2 C11B H11C . . 111.1 ?
C12B C11B H11C . . 111.1 ?
O2 C11B H11D . . 111.1 ?
C12B C11B H11D . . 111.1 ?
H11C C11B H11D . . 109.0 ?
C11B C12B C13B . . 125(2) ?
C11B C12B H12C . . 106.1 ?
C13B C12B H12C . . 106.1 ?
C11B C12B H12D . . 106.1 ?
C13B C12B H12D . . 106.1 ?
H12C C12B H12D . . 106.3 ?
C14B C13B C12B . . 83.6(14) ?
C14B C13B H13C . . 114.7 ?
C12B C13B H13C . . 114.7 ?
C14B C13B H13D . . 114.7 ?
C12B C13B H13D . . 114.7 ?
H13C C13B H13D . . 111.8 ?
C13B C14B H14D . . 109.5 ?
C13B C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
C13B C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
S C15 H15A . . 109.5 ?
S C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
S C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 . 1.491(2) ?
S C1 . 1.762(2) ?
S C15 . 1.794(3) ?
O1 C7 . 1.370(3) ?
O1 C8 . 1.376(3) ?
O2 C10 . 1.319(3) ?
O2 C11A . 1.471(14) ?
O2 C11B . 1.50(3) ?
O3 C10 . 1.199(3) ?
C1 C8 . 1.355(3) ?
C1 C2 . 1.444(3) ?
C2 C3 . 1.391(3) ?
C2 C7 . 1.396(3) ?
C3 C4 . 1.380(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.396(4) ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.380(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.486(3) ?
C9 C10 . 1.511(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11A C12A . 1.482(2) ?
C11A H11A . 0.9700 ?
C11A H11B . 0.9700 ?
C12A C13A . 1.489(2) ?
C12A H12A . 0.9700 ?
C12A H12B . 0.9700 ?
C13A C14A . 1.482(2) ?
C13A H13A . 0.9700 ?
C13A H13B . 0.9700 ?
C14A H14A . 0.9600 ?
C14A H14B . 0.9600 ?
C14A H14C . 0.9600 ?
C11B C12B . 1.481(2) ?
C11B H11C . 0.9700 ?
C11B H11D . 0.9700 ?
C12B C13B . 1.483(2) ?
C12B H12C . 0.9700 ?
C12B H12D . 0.9700 ?
C13B C14B . 1.481(2) ?
C13B H13C . 0.9700 ?
C13B H13D . 0.9700 ?
C14B H14D . 0.9600 ?
C14B H14E . 0.9600 ?
C14B H14F . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
C12A H12A Cg 1_665 0.97 2.78 3.698(5) 158
C5 H5 O3 2_565 0.93 2.55 3.405(3) 153
C9 H9B O4 2_666 0.97 2.30 3.248(3) 167
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 . . . . -136.3(2) ?
C15 S C1 C8 . . . . 114.3(2) ?
O4 S C1 C2 . . . . 39.5(2) ?
C15 S C1 C2 . . . . -69.9(2) ?
C8 C1 C2 C3 . . . . -177.6(3) ?
S C1 C2 C3 . . . . 6.1(4) ?
C8 C1 C2 C7 . . . . 0.7(3) ?
S C1 C2 C7 . . . . -175.63(18) ?
C7 C2 C3 C4 . . . . 1.4(3) ?
C1 C2 C3 C4 . . . . 179.5(2) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C2 C3 C4 Br . . . . -179.94(16) ?
C3 C4 C5 C6 . . . . -0.5(4) ?
Br C4 C5 C6 . . . . 179.14(18) ?
C4 C5 C6 C7 . . . . 0.1(4) ?
C8 O1 C7 C6 . . . . -179.6(2) ?
C8 O1 C7 C2 . . . . 0.8(2) ?
C5 C6 C7 O1 . . . . -178.5(2) ?
C5 C6 C7 C2 . . . . 1.1(4) ?
C3 C2 C7 O1 . . . . 177.69(19) ?
C1 C2 C7 O1 . . . . -0.9(2) ?
C3 C2 C7 C6 . . . . -1.9(3) ?
C1 C2 C7 C6 . . . . 179.5(2) ?
C2 C1 C8 O1 . . . . -0.3(3) ?
S C1 C8 O1 . . . . 176.29(16) ?
C2 C1 C8 C9 . . . . 175.7(2) ?
S C1 C8 C9 . . . . -7.8(4) ?
C7 O1 C8 C1 . . . . -0.3(2) ?
C7 O1 C8 C9 . . . . -177.00(19) ?
C1 C8 C9 C10 . . . . -73.0(3) ?
O1 C8 C9 C10 . . . . 102.8(2) ?
C11A O2 C10 O3 . . . . 2.1(6) ?
C11B O2 C10 O3 . . . . -15.4(11) ?
C11A O2 C10 C9 . . . . -176.9(5) ?
C11B O2 C10 C9 . . . . 165.7(10) ?
C8 C9 C10 O3 . . . . 24.4(4) ?
C8 C9 C10 O2 . . . . -156.7(2) ?
C10 O2 C11A C12A . . . . 174.3(5) ?
C11B O2 C11A C12A . . . . -74(4) ?
O2 C11A C12A C13A . . . . -78.9(8) ?
C11A C12A C13A C14A . . . . -172.1(9) ?
C10 O2 C11B C12B . . . . 128.1(15) ?
C11A O2 C11B C12B . . . . 51(3) ?
O2 C11B C12B C13B . . . . 69(3) ?
C11B C12B C13B C14B . . . . -171(3) ?
