#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233596.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_2233596
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 3-(3-Chlorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran
;
_journal_coeditor_code           PV2502
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o374
_journal_paper_doi               10.1107/S160053681200027X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H15 Cl O2 S'
_chemical_formula_moiety         'C17 H15 Cl O2 S'
_chemical_formula_sum            'C17 H15 Cl O2 S'
_chemical_formula_weight         318.80
_chemical_name_systematic
;
3-(3-Chlorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran
;
_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                76.763(2)
_cell_angle_beta                 84.145(2)
_cell_angle_gamma                73.241(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7900(2)
_cell_length_b                   8.1288(3)
_cell_length_c                   14.6813(5)
_cell_measurement_reflns_used    6373
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.68
_cell_volume                     754.73(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14017
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0368
_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)+(0.0546P)²+0.2190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                3182
_reflns_number_total             3704
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2502.cif
_cod_data_source_block           I
_cod_original_cell_volume        754.73(4)
_cod_database_code               2233596
_cod_database_fobs_code          2233596
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
Cl Cl1 0.98398(6) 0.23182(6) 0.99982(3) 0.04624(14) Uani d . 1 2
S S1 0.46056(6) 0.83926(5) 0.83535(3) 0.03407(12) Uani d . 1 2
O O1 0.14598(16) 0.96772(15) 0.61039(8) 0.0363(3) Uani d . 1 2
O O2 0.65568(19) 0.88857(16) 0.83626(9) 0.0443(3) Uani d . 1 2
C C1 0.3829(2) 0.8720(2) 0.72075(11) 0.0312(3) Uani d . 1 2
C C2 0.4775(2) 0.80409(19) 0.63819(10) 0.0300(3) Uani d . 1 2
C C3 0.6724(2) 0.7063(2) 0.61075(11) 0.0336(3) Uani d . 1 2
C C4 0.6909(2) 0.6719(2) 0.52105(12) 0.0368(3) Uani d . 1 2
H H4 0.8208 0.6054 0.5009 0.044 Uiso calc R 1 2
C C5 0.5309(3) 0.7288(2) 0.45904(11) 0.0367(3) Uani d . 1 2
C C6 0.3406(3) 0.8309(2) 0.48513(11) 0.0375(3) Uani d . 1 2
H H6 0.2289 0.8745 0.4442 0.045 Uiso calc R 1 2
C C7 0.3229(2) 0.8653(2) 0.57378(11) 0.0325(3) Uani d . 1 2
C C8 0.1876(2) 0.9692(2) 0.69925(11) 0.0336(3) Uani d . 1 2
C C9 0.8536(3) 0.6437(3) 0.67277(13) 0.0448(4) Uani d . 1 2
H H9A 0.8515 0.5309 0.7141 0.067 Uiso calc R 1 2
H H9B 0.8462 0.7303 0.7106 0.067 Uiso calc R 1 2
H H9C 0.9813 0.6291 0.6340 0.067 Uiso calc R 1 2
C C10 0.5634(3) 0.6788(3) 0.36442(12) 0.0464(4) Uani d . 1 2
H H10A 0.5396 0.5633 0.3706 0.070 Uiso calc R 1 2
H H10B 0.7047 0.6741 0.3408 0.070 Uiso calc R 1 2
H H10C 0.4667 0.7665 0.3205 0.070 Uiso calc R 1 2
C C11 0.0176(3) 1.0752(2) 0.75130(13) 0.0432(4) Uani d . 1 2
H H11A 0.0667 1.0788 0.8111 0.065 Uiso calc R 1 2
H H11B -0.0972 1.0217 0.7630 0.065 Uiso calc R 1 2
H H11C -0.0288 1.1950 0.7141 0.065 Uiso calc R 1 2
C C12 0.5290(2) 0.6027(2) 0.86348(10) 0.0302(3) Uani d . 1 2
C C13 0.7090(2) 0.5182(2) 0.91058(10) 0.0317(3) Uani d . 1 2
H H13 0.7954 0.5830 0.9234 0.038 Uiso calc R 1 2
C C14 0.7601(2) 0.3376(2) 0.93850(11) 0.0326(3) Uani d . 1 2
C C15 0.6376(2) 0.2399(2) 0.92032(11) 0.0339(3) Uani d . 1 2
H H15 0.6762 0.1155 0.9394 0.041 Uiso calc R 1 2
C C16 0.4574(3) 0.3280(2) 0.87360(11) 0.0355(3) Uani d . 1 2
H H16 0.3716 0.2629 0.8606 0.043 Uiso calc R 1 2
C C17 0.4002(2) 0.5095(2) 0.84550(11) 0.0339(3) Uani d . 1 2
H H17 0.2753 0.5690 0.8145 0.041 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'
Cl Cl 0.1484 0.1585 '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 111.41(7)
O2 S1 C12 106.01(7)
C1 S1 C12 98.39(7)
C8 O1 C7 106.59(12)
C8 C1 C2 107.12(14)
C8 C1 S1 118.56(12)
C2 C1 S1 134.08(12)
C7 C2 C3 118.49(14)
C7 C2 C1 104.44(13)
C3 C2 C1 137.02(14)
C4 C3 C2 116.22(15)
C4 C3 C9 121.02(14)
C2 C3 C9 122.75(14)
C5 C4 C3 124.16(15)
C5 C4 H4 117.9
C3 C4 H4 117.9
C6 C5 C4 119.45(15)
C6 C5 C10 120.21(16)
C4 C5 C10 120.34(15)
C7 C6 C5 116.27(15)
C7 C6 H6 121.9
C5 C6 H6 121.9
C6 C7 O1 123.93(14)
C6 C7 C2 125.32(14)
O1 C7 C2 110.75(13)
C1 C8 O1 111.09(13)
C1 C8 C11 133.38(16)
O1 C8 C11 115.53(14)
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 121.25(14)
C13 C12 S1 116.72(11)
C17 C12 S1 121.85(12)
C14 C13 C12 118.42(13)
C14 C13 H13 120.8
C12 C13 H13 120.8
C13 C14 C15 121.98(15)
C13 C14 Cl1 118.34(12)
C15 C14 Cl1 119.67(12)
C14 C15 C16 118.42(14)
C14 C15 H15 120.8
C16 C15 H15 120.8
C17 C16 C15 121.11(14)
C17 C16 H16 119.4
C15 C16 H16 119.4
C16 C17 C12 118.80(15)
C16 C17 H17 120.6
C12 C17 H17 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.7412(16)
S1 O2 1.4928(12)
S1 C1 1.7534(16)
S1 C12 1.8009(15)
O1 C8 1.3661(19)
O1 C7 1.3863(18)
C1 C8 1.360(2)
C1 C2 1.459(2)
C2 C7 1.389(2)
C2 C3 1.406(2)
C3 C4 1.394(2)
C3 C9 1.502(2)
C4 C5 1.393(2)
C4 H4 0.9500
C5 C6 1.390(2)
C5 C10 1.513(2)
C6 C7 1.379(2)
C6 H6 0.9500
C8 C11 1.486(2)
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 1.384(2)
C12 C17 1.389(2)
C13 C14 1.380(2)
C13 H13 0.9500
C14 C15 1.384(2)
C15 C16 1.386(2)
C15 H15 0.9500
C16 C17 1.386(2)
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 H11B O2 1_455 0.98 2.30 3.249(2) 162.8
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 -127.62(13)
C12 S1 C1 C8 121.46(13)
O2 S1 C1 C2 58.83(17)
C12 S1 C1 C2 -52.10(16)
C8 C1 C2 C7 -1.54(16)
S1 C1 C2 C7 172.54(13)
C8 C1 C2 C3 175.63(17)
S1 C1 C2 C3 -10.3(3)
C7 C2 C3 C4 -2.9(2)
C1 C2 C3 C4 -179.79(16)
C7 C2 C3 C9 176.05(15)
C1 C2 C3 C9 -0.8(3)
C2 C3 C4 C5 0.4(2)
C9 C3 C4 C5 -178.61(16)
C3 C4 C5 C6 1.9(2)
C3 C4 C5 C10 -177.54(15)
C4 C5 C6 C7 -1.5(2)
C10 C5 C6 C7 177.93(14)
C5 C6 C7 O1 178.59(14)
C5 C6 C7 C2 -1.1(2)
C8 O1 C7 C6 179.30(15)
C8 O1 C7 C2 -0.93(16)
C3 C2 C7 C6 3.5(2)
C1 C2 C7 C6 -178.73(15)
C3 C2 C7 O1 -176.29(13)
C1 C2 C7 O1 1.51(16)
C2 C1 C8 O1 1.05(17)
S1 C1 C8 O1 -174.11(10)
C2 C1 C8 C11 -177.87(17)
S1 C1 C8 C11 7.0(3)
C7 O1 C8 C1 -0.11(17)
C7 O1 C8 C11 179.01(13)
O2 S1 C12 C13 22.00(13)
C1 S1 C12 C13 137.22(12)
O2 S1 C12 C17 -162.87(12)
C1 S1 C12 C17 -47.65(13)
C17 C12 C13 C14 0.9(2)
S1 C12 C13 C14 176.04(11)
C12 C13 C14 C15 0.3(2)
C12 C13 C14 Cl1 -178.73(11)
C13 C14 C15 C16 -0.8(2)
Cl1 C14 C15 C16 178.26(12)
C14 C15 C16 C17 0.1(2)
C15 C16 C17 C12 1.1(2)
C13 C12 C17 C16 -1.6(2)
S1 C12 C17 C16 -176.51(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139083013
