#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/30/2233076.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_2233076
loop_
_publ_author_name
'Seo, Pil Ja'
'Choi, Hong Dae'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(5-Bromo-3-isopropylsulfanyl-1-benzofuran-2-yl)acetic acid
;
_journal_coeditor_code           BG2430
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o58
_journal_paper_doi               10.1107/S1600536811052160
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H13 Br O3 S'
_chemical_formula_moiety         'C13 H13 Br O3 S'
_chemical_formula_sum            'C13 H13 Br O3 S'
_chemical_formula_weight         329.20
_chemical_name_systematic
;
2-(5-Bromo-3-isopropylsulfanyl-1-benzofuran-2-yl)acetic acid
;
_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                98.415(2)
_cell_angle_beta                 102.146(2)
_cell_angle_gamma                110.341(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4689(3)
_cell_length_b                   9.9449(4)
_cell_length_c                   10.0653(4)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.25
_cell_volume                     665.38(5)
_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      296(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0260
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11869
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.242
_exptl_absorpt_correction_T_max  0.7375
_exptl_absorpt_correction_T_min  0.5100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.1792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0636
_reflns_number_gt                2731
_reflns_number_total             3082
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2430.cif
_cod_data_source_block           I
_cod_database_code               2233076
_cod_database_fobs_code          2233076
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_symmetry_multiplicity
Br Br1 0.19969(3) -0.066508(19) 0.14451(2) 0.03256(8) Uani d . 1 2
S S1 0.19347(6) 0.56388(5) 0.18733(4) 0.02002(10) Uani d . 1 2
O O1 0.71390(18) 0.55476(13) 0.17068(13) 0.0206(2) Uani d . 1 2
O O2 0.8525(2) 1.01742(15) 0.34019(17) 0.0322(3) Uani d . 1 2
H H2O 0.925(4) 1.059(3) 0.409(3) 0.050(9) Uiso d . 1 2
O O3 0.8861(2) 0.82564(14) 0.41728(14) 0.0290(3) Uani d . 1 2
C C1 0.4055(2) 0.52528(18) 0.18780(17) 0.0180(3) Uani d . 1 2
C C2 0.4198(2) 0.38295(18) 0.17355(17) 0.0176(3) Uani d . 1 2
C C3 0.2914(3) 0.24052(18) 0.16819(18) 0.0196(3) Uani d . 1 2
H H3 0.1627 0.2202 0.1749 0.024 Uiso calc R 1 2
C C4 0.3645(3) 0.13091(19) 0.15246(18) 0.0213(3) Uani d . 1 2
C C5 0.5565(3) 0.1574(2) 0.14170(19) 0.0227(4) Uani d . 1 2
H H5 0.5989 0.0799 0.1316 0.027 Uiso calc R 1 2
C C6 0.6840(3) 0.2986(2) 0.14606(19) 0.0223(4) Uani d . 1 2
H H6 0.8119 0.3185 0.1379 0.027 Uiso calc R 1 2
C C7 0.6116(2) 0.40805(18) 0.16307(17) 0.0190(3) Uani d . 1 2
C C8 0.5840(3) 0.62221(18) 0.18556(17) 0.0184(3) Uani d . 1 2
C C9 0.6588(3) 0.78314(18) 0.19365(18) 0.0207(3) Uani d . 1 2
H H9A 0.5471 0.8131 0.1809 0.025 Uiso calc R 1 2
H H9B 0.7170 0.8019 0.1172 0.025 Uiso calc R 1 2
C C10 0.8114(3) 0.87651(19) 0.32922(19) 0.0210(3) Uani d . 1 2
C C11 0.2061(3) 0.6058(2) 0.37390(19) 0.0252(4) Uani d . 1 2
H H11 0.0865 0.6237 0.3795 0.030 Uiso calc R 1 2
C C12 0.3829(3) 0.7457(2) 0.4566(2) 0.0377(5) Uani d . 1 2
H H12A 0.3768 0.7682 0.5511 0.056 Uiso calc R 1 2
H H12B 0.3803 0.8259 0.4144 0.056 Uiso calc R 1 2
H H12C 0.5038 0.7317 0.4565 0.056 Uiso calc R 1 2
C C13 0.1986(3) 0.4754(2) 0.4379(2) 0.0326(4) Uani d . 1 2
H H13A 0.3110 0.4516 0.4314 0.049 Uiso calc R 1 2
H H13B 0.0780 0.3916 0.3882 0.049 Uiso calc R 1 2
H H13C 0.2020 0.5004 0.5344 0.049 Uiso calc R 1 2
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
C1 S1 C11 103.26(8)
C7 O1 C8 105.80(12)
C10 O2 H2O 108(2)
C8 C1 C2 106.08(14)
C8 C1 S1 125.91(13)
C2 C1 S1 127.62(13)
C3 C2 C7 119.53(15)
C3 C2 C1 134.93(15)
C7 C2 C1 105.53(14)
C4 C3 C2 116.75(15)
C4 C3 H3 121.6
C2 C3 H3 121.6
C3 C4 C5 123.14(16)
C3 C4 Br1 119.60(13)
C5 C4 Br1 117.26(13)
C6 C5 C4 120.26(16)
C6 C5 H5 119.9
C4 C5 H5 119.9
C7 C6 C5 116.58(16)
C7 C6 H6 121.7
C5 C6 H6 121.7
O1 C7 C6 125.78(15)
O1 C7 C2 110.49(14)
C6 C7 C2 123.73(16)
C1 C8 O1 112.10(14)
C1 C8 C9 131.51(16)
O1 C8 C9 116.38(14)
C8 C9 C10 114.05(14)
C8 C9 H9A 108.7
C10 C9 H9A 108.7
C8 C9 H9B 108.7
C10 C9 H9B 108.7
H9A C9 H9B 107.6
O3 C10 O2 124.59(17)
O3 C10 C9 123.37(16)
O2 C10 C9 112.04(15)
C12 C11 C13 112.01(17)
C12 C11 S1 112.33(13)
C13 C11 S1 111.88(13)
C12 C11 H11 106.7
C13 C11 H11 106.7
S1 C11 H11 106.7
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 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_distance
Br1 C4 1.8996(17)
S1 C1 1.7533(17)
S1 C11 1.8380(18)
O1 C7 1.373(2)
O1 C8 1.378(2)
O2 C10 1.308(2)
O2 H2O 0.74(3)
O3 C10 1.213(2)
C1 C8 1.354(2)
C1 C2 1.445(2)
C2 C3 1.393(2)
C2 C7 1.396(2)
C3 C4 1.382(2)
C3 H3 0.9300
C4 C5 1.396(3)
C5 C6 1.383(3)
C5 H5 0.9300
C6 C7 1.378(2)
C6 H6 0.9300
C8 C9 1.484(2)
C9 C10 1.504(2)
C9 H9A 0.9700
C9 H9B 0.9700
C11 C12 1.515(3)
C11 C13 1.519(3)
C11 H11 0.9800
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
O2 H2O O3 2_776 0.74(3) 1.90(3) 2.640(2) 177(3)
C9 H9B Cg2 2_665 0.97 2.717(2) 3.376(2) 125.6
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
C11 S1 C1 C8 -95.71(16)
C11 S1 C1 C2 92.46(16)
C8 C1 C2 C3 -179.91(18)
S1 C1 C2 C3 -6.8(3)
C8 C1 C2 C7 -0.27(18)
S1 C1 C2 C7 172.85(13)
C7 C2 C3 C4 0.0(2)
C1 C2 C3 C4 179.61(18)
C2 C3 C4 C5 -0.2(3)
C2 C3 C4 Br1 179.88(12)
C3 C4 C5 C6 -0.2(3)
Br1 C4 C5 C6 179.71(13)
C4 C5 C6 C7 0.8(3)
C8 O1 C7 C6 179.14(17)
C8 O1 C7 C2 -0.24(17)
C5 C6 C7 O1 179.67(16)
C5 C6 C7 C2 -1.0(3)
C3 C2 C7 O1 -179.98(14)
C1 C2 C7 O1 0.32(18)
C3 C2 C7 C6 0.6(3)
C1 C2 C7 C6 -179.08(16)
C2 C1 C8 O1 0.13(19)
S1 C1 C8 O1 -173.14(12)
C2 C1 C8 C9 178.91(17)
S1 C1 C8 C9 5.6(3)
C7 O1 C8 C1 0.06(18)
C7 O1 C8 C9 -178.91(14)
C1 C8 C9 C10 109.0(2)
O1 C8 C9 C10 -72.23(19)
C8 C9 C10 O3 8.9(3)
C8 C9 C10 O2 -170.96(15)
C1 S1 C11 C12 66.06(16)
C1 S1 C11 C13 -60.93(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657301
