#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233585.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_2233585
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 3-(4-Bromophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran
;
_journal_coeditor_code           PK2381
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o456
_journal_paper_doi               10.1107/S1600536812001547
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H15 Br O2 S'
_chemical_formula_moiety         'C17 H15 Br O2 S'
_chemical_formula_sum            'C17 H15 Br O2 S'
_chemical_formula_weight         363.26
_chemical_name_systematic
;
3-(4-Bromophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0911(3)
_cell_length_b                   19.4713(3)
_cell_length_c                   6.44820(10)
_cell_measurement_reflns_used    3220
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.69
_cell_volume                     1518.10(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      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  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    0.0501
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8258
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.846
_exptl_absorpt_correction_T_max  0.611
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.546
_refine_ls_abs_structure_details 'Flack (1983), 1131 Friedel pairs'
_refine_ls_abs_structure_Flack   0.014(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3190
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0317
_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)+(0.0362P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                2797
_reflns_number_total             3190
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2381.cif
_cod_data_source_block           I
_cod_database_code               2233585
_cod_database_fobs_code          2233585
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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 0.50103(3) 0.448031(17) 0.95844(11) 0.04606(11) Uani d . 1 2
S S1 0.59546(5) 0.24377(3) 0.19734(12) 0.02620(14) Uani d . 1 2
O O1 0.32864(13) 0.13364(8) 0.1240(3) 0.0271(4) Uani d . 1 2
O O2 0.70481(13) 0.21095(9) 0.2396(3) 0.0337(4) Uani d . 1 2
C C1 0.48796(18) 0.18334(13) 0.2236(4) 0.0232(5) Uani d . 1 2
C C2 0.4617(2) 0.13067(12) 0.3768(4) 0.0218(5) Uani d . 1 2
C C3 0.50764(18) 0.10532(15) 0.5613(5) 0.0244(6) Uani d . 1 2
C C4 0.4501(2) 0.05337(12) 0.6611(4) 0.0280(6) Uani d . 1 2
H H4 0.4799 0.0352 0.7859 0.034 Uiso calc R 1 2
C C5 0.3494(2) 0.02600(13) 0.5871(5) 0.0300(6) Uani d . 1 2
C C6 0.3051(2) 0.05052(12) 0.4044(4) 0.0286(6) Uani d . 1 2
H H6 0.2382 0.0327 0.3488 0.034 Uiso calc R 1 2
C C7 0.3631(2) 0.10222(12) 0.3065(4) 0.0249(5) Uani d . 1 2
C C8 0.4063(2) 0.18286(12) 0.0785(4) 0.0244(5) Uani d . 1 2
C C9 0.6138(2) 0.13299(14) 0.6532(4) 0.0326(6) Uani d . 1 2
H H9A 0.5976 0.1742 0.7350 0.049 Uiso calc R 1 2
H H9B 0.6653 0.1447 0.5413 0.049 Uiso calc R 1 2
H H9C 0.6472 0.0980 0.7428 0.049 Uiso calc R 1 2
C C10 0.2906(2) -0.02817(14) 0.7122(6) 0.0449(7) Uani d . 1 2
H H10A 0.2119 -0.0282 0.6764 0.067 Uiso calc R 1 2
H H10B 0.2992 -0.0182 0.8603 0.067 Uiso calc R 1 2
H H10C 0.3225 -0.0733 0.6814 0.067 Uiso calc R 1 2
C C11 0.3837(2) 0.22527(13) -0.1055(4) 0.0290(6) Uani d . 1 2
H H11A 0.3762 0.1956 -0.2275 0.043 Uiso calc R 1 2
H H11B 0.4449 0.2575 -0.1271 0.043 Uiso calc R 1 2
H H11C 0.3149 0.2510 -0.0846 0.043 Uiso calc R 1 2
C C12 0.5641(2) 0.29687(12) 0.4160(4) 0.0246(6) Uani d . 1 2
C C13 0.6479(2) 0.31154(13) 0.5558(4) 0.0286(6) Uani d . 1 2
H H13 0.7185 0.2908 0.5399 0.034 Uiso calc R 1 2
C C14 0.6288(2) 0.35637(12) 0.7187(5) 0.0289(6) Uani d . 1 2
H H14 0.6851 0.3657 0.8175 0.035 Uiso calc R 1 2
C C15 0.5266(2) 0.38710(13) 0.7346(4) 0.0279(6) Uani d . 1 2
C C16 0.4426(2) 0.37384(13) 0.5940(5) 0.0306(6) Uani d . 1 2
H H16 0.3728 0.3958 0.6080 0.037 Uiso calc R 1 2
C C17 0.4610(2) 0.32882(13) 0.4347(5) 0.0299(6) Uani d . 1 2
H H17 0.4041 0.3193 0.3373 0.036 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
O2 S1 C1 110.48(11)
O2 S1 C12 106.92(11)
C1 S1 C12 98.85(12)
C8 O1 C7 106.43(19)
C8 C1 C2 107.6(2)
C8 C1 S1 118.3(2)
C2 C1 S1 134.1(2)
C7 C2 C3 118.4(2)
C7 C2 C1 104.2(2)
C3 C2 C1 137.3(2)
C4 C3 C2 116.8(2)
C4 C3 C9 120.2(3)
C2 C3 C9 122.9(2)
C3 C4 C5 123.5(2)
C3 C4 H4 118.3
C5 C4 H4 118.3
C6 C5 C4 119.5(2)
C6 C5 C10 121.1(3)
C4 C5 C10 119.4(3)
C7 C6 C5 116.5(2)
C7 C6 H6 121.8
C5 C6 H6 121.8
C6 C7 O1 123.8(2)
C6 C7 C2 125.2(2)
O1 C7 C2 111.0(2)
C1 C8 O1 110.8(2)
C1 C8 C11 133.3(2)
O1 C8 C11 115.9(2)
C3 C9 H9A 109.5
C3 C9 H9B 109.5
H9A C9 H9B 109.5
C3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C5 C10 H10A 109.5
C5 C10 H10B 109.5
H10A C10 H10B 109.5
C5 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 120.3(2)
C13 C12 S1 118.47(19)
C17 C12 S1 120.92(19)
C14 C13 C12 120.1(2)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 118.7(3)
C15 C14 H14 120.7
C13 C14 H14 120.7
C14 C15 C16 121.9(3)
C14 C15 Br1 118.4(2)
C16 C15 Br1 119.7(2)
C17 C16 C15 119.4(2)
C17 C16 H16 120.3
C15 C16 H16 120.3
C16 C17 C12 119.6(3)
C16 C17 H17 120.2
C12 C17 H17 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.894(3)
S1 O2 1.4935(18)
S1 C1 1.761(2)
S1 C12 1.789(3)
O1 C8 1.373(3)
O1 C7 1.390(3)
C1 C8 1.360(4)
C1 C2 1.459(4)
C2 C7 1.390(4)
C2 C3 1.403(4)
C3 C4 1.386(4)
C3 C9 1.513(3)
C4 C5 1.412(4)
C4 H4 0.9500
C5 C6 1.380(4)
C5 C10 1.506(4)
C6 C7 1.380(3)
C6 H6 0.9500
C8 C11 1.471(4)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.386(3)
C12 C17 1.398(4)
C13 C14 1.385(4)
C13 H13 0.9500
C14 C15 1.377(4)
C14 H14 0.9500
C15 C16 1.386(4)
C16 C17 1.369(4)
C16 H16 0.9500
C17 H17 0.9500
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 H11C O2 4_455 0.98 2.59 3.343(3) 134.0
C17 H17 O2 4_455 0.95 2.56 3.432(3) 152.8
C4 H4 Cg 2_655 0.95 2.89 3.724(3) 146.7
C11 H11A Cg 1_554 0.98 2.98 3.917(3) 161.0
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 S1 C1 C8 -136.6(2)
C12 S1 C1 C8 111.5(2)
O2 S1 C1 C2 45.2(3)
C12 S1 C1 C2 -66.7(3)
C8 C1 C2 C7 0.2(3)
S1 C1 C2 C7 178.6(2)
C8 C1 C2 C3 -178.9(3)
S1 C1 C2 C3 -0.6(5)
C7 C2 C3 C4 -0.3(4)
C1 C2 C3 C4 178.7(3)
C7 C2 C3 C9 -179.3(2)
C1 C2 C3 C9 -0.3(5)
C2 C3 C4 C5 -0.4(4)
C9 C3 C4 C5 178.6(2)
C3 C4 C5 C6 1.1(4)
C3 C4 C5 C10 -177.2(3)
C4 C5 C6 C7 -1.1(4)
C10 C5 C6 C7 177.2(2)
C5 C6 C7 O1 -178.5(2)
C5 C6 C7 C2 0.4(4)
C8 O1 C7 C6 178.8(2)
C8 O1 C7 C2 -0.2(3)
C3 C2 C7 C6 0.3(4)
C1 C2 C7 C6 -179.0(2)
C3 C2 C7 O1 179.3(2)
C1 C2 C7 O1 0.0(3)
C2 C1 C8 O1 -0.3(3)
S1 C1 C8 O1 -179.02(17)
C2 C1 C8 C11 176.7(3)
S1 C1 C8 C11 -2.0(4)
C7 O1 C8 C1 0.4(3)
C7 O1 C8 C11 -177.2(2)
O2 S1 C12 C13 13.9(2)
C1 S1 C12 C13 128.6(2)
O2 S1 C12 C17 -172.8(2)
C1 S1 C12 C17 -58.1(2)
C17 C12 C13 C14 2.0(4)
S1 C12 C13 C14 175.40(19)
C12 C13 C14 C15 -1.8(4)
C13 C14 C15 C16 0.7(4)
C13 C14 C15 Br1 179.7(2)
C14 C15 C16 C17 0.2(4)
Br1 C15 C16 C17 -178.9(2)
C15 C16 C17 C12 0.0(4)
C13 C12 C17 C16 -1.1(4)
S1 C12 C17 C16 -174.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139083004
