#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/52/2215281.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_2215281
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 Ethyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
;
_journal_coeditor_code           TK2188
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3850
_journal_page_last               o3850
_journal_paper_doi               10.1107/S160053680704041X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H13 Br O4 S'
_chemical_formula_moiety         'C13 H13 Br O4 S'
_chemical_formula_sum            'C13 H13 Br O4 S'
_chemical_formula_weight         345.20
_chemical_name_systematic
;
Ethyl 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
_cell_angle_alpha                71.6440(10)
_cell_angle_beta                 78.6190(10)
_cell_angle_gamma                65.3040(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3557(4)
_cell_length_b                   9.5625(5)
_cell_length_c                   10.0192(5)
_cell_measurement_reflns_used    4506
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.2
_cell_volume                     688.31(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.016
_diffrn_reflns_av_sigmaI/netI    0.021
_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            5994
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.144
_exptl_absorpt_correction_T_max  0.541
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.024
_refine_ls_R_factor_gt           0.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.031P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.059
_reflns_number_gt                2772
_reflns_number_total             2961
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2188.cif
_cod_data_source_block           I
_cod_database_code               2215281
_cod_database_fobs_code          2215281
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 1.19929(2) 0.29496(2) 0.09731(2) 0.03275(7) Uani d . 1
S S 0.77219(6) -0.11607(5) 0.46784(4) 0.02467(10) Uani d . 1
O O1 0.66177(15) 0.04723(13) 0.06926(11) 0.0211(2) Uani d . 1
O O2 0.76708(18) 0.01229(17) 0.52618(13) 0.0339(3) Uani d . 1
O O3 0.51765(17) -0.37582(15) 0.27271(15) 0.0303(3) Uani d . 1
O O4 0.76958(18) -0.37966(16) 0.32289(16) 0.0359(3) Uani d . 1
C C1 0.7622(2) -0.03343(19) 0.28450(16) 0.0198(3) Uani d . 1
C C2 0.8492(2) 0.06848(19) 0.19260(16) 0.0197(3) Uani d . 1
C C3 0.9766(2) 0.12143(19) 0.20606(17) 0.0219(3) Uani d . 1
H H3 1.0273 0.0910 0.2928 0.026 Uiso calc R 1
C C4 1.0248(2) 0.2206(2) 0.08611(18) 0.0231(3) Uani d . 1
C C5 0.9530(2) 0.2688(2) -0.04359(18) 0.0246(3) Uani d . 1
H H5 0.9900 0.3382 -0.1221 0.030 Uiso calc R 1
C C6 0.8282(2) 0.2155(2) -0.05775(17) 0.0236(3) Uani d . 1
H H6 0.7778 0.2461 -0.1447 0.028 Uiso calc R 1
C C7 0.7807(2) 0.11484(19) 0.06213(17) 0.0200(3) Uani d . 1
C C8 0.6524(2) -0.04197(19) 0.20650(16) 0.0199(3) Uani d . 1
C C9 0.5307(2) -0.1276(2) 0.23858(17) 0.0223(3) Uani d . 1
H H9A 0.4667 -0.0971 0.1541 0.027 Uiso calc R 1
H H9B 0.4421 -0.0931 0.3154 0.027 Uiso calc R 1
C C10 0.6233(2) -0.3068(2) 0.28198(17) 0.0232(3) Uani d . 1
C C11 0.5906(3) -0.5504(2) 0.3129(3) 0.0385(5) Uani d . 1
H H11A 0.6164 -0.5916 0.4133 0.046 Uiso calc R 1
H H11B 0.7015 -0.5917 0.2548 0.046 Uiso calc R 1
C C12 0.4550(3) -0.6019(3) 0.2887(3) 0.0517(6) Uani d . 1
H H12A 0.4308 -0.5606 0.1890 0.062 Uiso calc R 1
H H12B 0.3459 -0.5604 0.3468 0.062 Uiso calc R 1
H H12C 0.4993 -0.7187 0.3146 0.062 Uiso calc R 1
C C13 0.9969(3) -0.2565(2) 0.4702(2) 0.0339(4) Uani d . 1
H H13A 1.0248 -0.3146 0.5679 0.051 Uiso calc R 1
H H13B 1.0760 -0.1996 0.4271 0.051 Uiso calc R 1
H H13C 1.0125 -0.3321 0.4169 0.051 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 105.74(8)
O2 S C13 106.19(9)
C1 S C13 98.98(8)
C7 O1 C8 106.30(10)
C10 O3 C11 116.10(10)
C8 C1 C2 107.40(10)
C8 C1 S 124.30(10)
C2 C1 S 128.00(10)
C7 C2 C3 119.6(2)
C7 C2 C1 104.60(10)
C3 C2 C1 135.9(2)
C4 C3 C2 116.4(2)
C4 C3 H3 121.8
C2 C3 H3 121.8
C3 C4 C5 123.6(2)
C3 C4 Br 118.30(10)
C5 C4 Br 118.00(10)
C6 C5 C4 120.2(2)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 116.3(2)
C5 C6 H6 121.8
C7 C6 H6 121.8
O1 C7 C6 125.30(10)
O1 C7 C2 110.90(10)
C6 C7 C2 123.9(2)
C1 C8 O1 110.80(10)
C1 C8 C9 133.5(2)
O1 C8 C9 115.70(10)
C8 C9 C10 113.50(10)
C8 C9 H9A 108.9
C10 C9 H9A 108.9
C8 C9 H9B 108.9
C10 C9 H9B 108.9
H9A C9 H9B 107.7
O4 C10 O3 123.8(2)
O4 C10 C9 125.9(2)
O3 C10 C9 110.20(10)
O3 C11 C12 107.2(2)
O3 C11 H11A 110.3
C12 C11 H11A 110.3
O3 C11 H11B 110.3
C12 C11 H11B 110.3
H11A C11 H11B 108.5
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
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_distance
Br C4 1.904(2)
S O2 1.5000(10)
S C1 1.760(2)
S C13 1.794(2)
O1 C7 1.375(2)
O1 C8 1.378(2)
O3 C10 1.334(2)
O3 C11 1.464(2)
O4 C10 1.206(2)
C1 C8 1.358(2)
C1 C2 1.445(2)
C2 C7 1.397(2)
C2 C3 1.399(2)
C3 C4 1.384(2)
C3 H3 0.9500
C4 C5 1.400(2)
C5 C6 1.383(2)
C5 H5 0.9500
C6 C7 1.389(2)
C6 H6 0.9500
C8 C9 1.486(2)
C9 C10 1.510(2)
C9 H9A 0.9900
C9 H9B 0.9900
C11 C12 1.495(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
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_756 0.95 2.43 3.352(2) 164
C9 H9B O2 2_656 0.99 2.17 3.161(2) 176
C9 H9A O1 2_655 0.99 2.50 3.4816(19) 173
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 -132.39(15)
C13 S C1 C8 117.86(15)
O2 S C1 C2 40.01(17)
C13 S C1 C2 -69.74(16)
C8 C1 C2 C7 0.28(18)
S C1 C2 C7 -173.14(12)
C8 C1 C2 C3 -178.31(18)
S C1 C2 C3 8.3(3)
C7 C2 C3 C4 0.9(2)
C1 C2 C3 C4 179.38(17)
C2 C3 C4 C5 0.2(2)
C2 C3 C4 Br -179.40(12)
C3 C4 C5 C6 -0.8(3)
Br C4 C5 C6 178.78(13)
C4 C5 C6 C7 0.2(2)
C8 O1 C7 C6 -179.42(15)
C8 O1 C7 C2 0.74(17)
C5 C6 C7 O1 -178.85(15)
C5 C6 C7 C2 1.0(2)
C3 C2 C7 O1 178.24(14)
C1 C2 C7 O1 -0.64(17)
C3 C2 C7 C6 -1.6(2)
C1 C2 C7 C6 179.53(15)
C2 C1 C8 O1 0.17(18)
S C1 C8 O1 173.89(11)
C2 C1 C8 C9 179.06(17)
S C1 C8 C9 -7.2(3)
C7 O1 C8 C1 -0.55(17)
C7 O1 C8 C9 -179.66(13)
C1 C8 C9 C10 -62.5(2)
O1 C8 C9 C10 116.37(15)
C11 O3 C10 O4 -1.3(3)
C11 O3 C10 C9 -179.58(16)
C8 C9 C10 O4 18.2(2)
C8 C9 C10 O3 -163.55(14)
C10 O3 C11 C12 -177.56(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123506
2 PubChem 139073015
