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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/89/1558973.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1558973
loop_
_publ_author_name
'He, Chuan'
'Yang, Wu'
'Li, Yingzi'
'Zhu, Jiefeng'
'Liu, Wentan'
'Ke, Jie'
_publ_section_title
;
 Lewis Acid-Assisted Ir(III) Reductive Elimination Enables Construction of
 Seven-Membered-Ring Sulfoxides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04180G
_journal_year                    2020
_chemical_formula_moiety         'C10 H8 O S3'
_chemical_formula_sum            'C10 H8 O S3'
_chemical_formula_weight         240.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.673(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1465(5)
_cell_length_b                   14.4371(8)
_cell_length_c                   8.8840(5)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100
_cell_measurement_theta_max      45.27
_cell_measurement_theta_min      2.73
_cell_volume                     1026.79(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.358
_diffrn_reflns_theta_min         2.727
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0756 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.8896. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         8609
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0416P)²+0.4808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6542
_reflns_number_total             8609
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04180g2.cif
_cod_data_source_block           cxy0815_0m
_cod_database_code               1558973
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Restrained distances
 S3-O1 \\sim S3A-O1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(S3) = Uanis(S3A)
4. Others
 Sof(H5BC)=Sof(H5BD)=Sof(H9BC)=Sof(H9BD)=Sof(O1A)=Sof(S3A)=1-FVAR(1)
 Sof(S3)=Sof(O1)=Sof(H5AA)=Sof(H5AB)=Sof(H9AA)=Sof(H9AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5AA,H5AB), C5(H5BC,H5BD), C9(H9AA,H9AB), C9(H9BC,H9BD)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34426(3) 0.73416(2) 0.90315(3) 0.01625(4) Uani 1 1 d . . . . .
S2 S 0.73972(3) 0.64784(2) 0.84118(3) 0.01849(5) Uani 1 1 d . . . . .
S3 S 0.27819(5) 0.42912(2) 0.61136(4) 0.01471(6) Uani 0.958(2) 1 d D . P A 1
O1 O 0.11205(10) 0.40115(6) 0.64509(11) 0.02534(18) Uani 0.958(2) 1 d D . P A 1
C1 C 0.14287(11) 0.74220(6) 0.80449(11) 0.01541(13) Uani 1 1 d . . . . .
H1 H 0.063002 0.785596 0.826715 0.018 Uiso 1 1 calc R . . . .
C2 C 0.38936(10) 0.64410(5) 0.79064(9) 0.01139(10) Uani 1 1 d . . . . .
C3 C 0.54757(10) 0.59522(6) 0.81342(9) 0.01179(11) Uani 1 1 d . . . . .
C4 C 0.84215(11) 0.54357(7) 0.85127(11) 0.01808(14) Uani 1 1 d . . . . .
H4 H 0.960118 0.536905 0.867249 0.022 Uiso 1 1 calc R . . . .
C5 C 0.26451(11) 0.55095(6) 0.55854(8) 0.01295(11) Uani 1 1 d . . . . .
H5AA H 0.363779 0.566329 0.513823 0.016 Uiso 0.958(2) 1 calc R . P A 1
H5AB H 0.165305 0.558898 0.476431 0.016 Uiso 0.958(2) 1 calc R . P A 1
H5BC H 0.372601 0.558386 0.524125 0.016 Uiso 0.042(2) 1 calc R . P A 2
H5BD H 0.174123 0.562553 0.469515 0.016 Uiso 0.042(2) 1 calc R . P A 2
C6 C 0.25320(9) 0.62062(5) 0.68055(8) 0.01085(10) Uani 1 1 d . . . . .
C7 C 0.11198(10) 0.67720(6) 0.68830(9) 0.01375(12) Uani 1 1 d . . . . .
H7 H 0.007535 0.670992 0.620815 0.017 Uiso 1 1 calc R . . . .
C8 C 0.56077(10) 0.49978(6) 0.81104(8) 0.01168(11) Uani 1 1 d . . . . .
C9 C 0.41088(10) 0.43874(6) 0.80039(9) 0.01316(11) Uani 1 1 d . . . . .
H9AA H 0.341815 0.462195 0.872868 0.016 Uiso 0.958(2) 1 calc R . P A 1
H9AB H 0.449316 0.375848 0.834728 0.016 Uiso 0.958(2) 1 calc R . P A 1
H9BC H 0.353778 0.457983 0.884454 0.016 Uiso 0.042(2) 1 calc R . P A 2
H9BD H 0.453916 0.375439 0.825939 0.016 Uiso 0.042(2) 1 calc R . P A 2
C10 C 0.73017(11) 0.47027(7) 0.83305(10) 0.01595(13) Uani 1 1 d . . . . .
H10 H 0.763070 0.407090 0.835053 0.019 Uiso 1 1 calc R . . . .
O1A O 0.325(2) 0.3745(13) 0.518(2) 0.02534(18) Uani 0.042(2) 1 d D . P A 2
S3A S 0.2466(12) 0.4273(6) 0.6287(10) 0.01471(6) Uani 0.042(2) 1 d D . P A 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C2 92.36(4) . . ?
C4 S2 C3 92.35(4) . . ?
O1 S3 C5 107.37(5) . . ?
O1 S3 C9 103.88(5) . . ?
C5 S3 C9 99.28(4) . . ?
S1 C1 H1 124.4 . . ?
C7 C1 S1 111.11(6) . . ?
C7 C1 H1 124.4 . . ?
C3 C2 S1 124.51(6) . . ?
C6 C2 S1 111.57(6) . . ?
C6 C2 C3 123.84(7) . . ?
C2 C3 S2 124.61(6) . . ?
C8 C3 S2 111.83(6) . . ?
C8 C3 C2 123.53(7) . . ?
S2 C4 H4 124.4 . . ?
C10 C4 S2 111.12(6) . . ?
C10 C4 H4 124.4 . . ?
S3 C5 H5AA 107.8 . . ?
S3 C5 H5AB 107.8 . . ?
H5AA C5 H5AB 107.1 . . ?
H5BC C5 H5BD 107.9 . . ?
C6 C5 S3 118.23(5) . . ?
C6 C5 H5AA 107.8 . . ?
C6 C5 H5AB 107.8 . . ?
C6 C5 H5BC 109.2 . . ?
C6 C5 H5BD 109.2 . . ?
C6 C5 S3A 112.0(3) . . ?
S3A C5 H5BC 109.2 . . ?
S3A C5 H5BD 109.2 . . ?
C2 C6 C5 122.05(7) . . ?
C2 C6 C7 112.09(7) . . ?
C7 C6 C5 125.50(7) . . ?
C1 C7 C6 112.87(7) . . ?
C1 C7 H7 123.6 . . ?
C6 C7 H7 123.6 . . ?
C3 C8 C9 121.58(7) . . ?
C3 C8 C10 111.87(7) . . ?
C10 C8 C9 126.33(8) . . ?
S3 C9 H9AA 108.3 . . ?
S3 C9 H9AB 108.3 . . ?
C8 C9 S3 116.14(6) . . ?
C8 C9 H9AA 108.3 . . ?
C8 C9 H9AB 108.3 . . ?
C8 C9 H9BC 106.2 . . ?
C8 C9 H9BD 106.2 . . ?
C8 C9 S3A 124.4(3) . . ?
H9AA C9 H9AB 107.4 . . ?
H9BC C9 H9BD 106.4 . . ?
S3A C9 H9BC 106.2 . . ?
S3A C9 H9BD 106.2 . . ?
C4 C10 C8 112.82(8) . . ?
C4 C10 H10 123.6 . . ?
C8 C10 H10 123.6 . . ?
C9 S3A C5 95.7(4) . . ?
O1A S3A C5 101.3(9) . . ?
O1A S3A C9 105.1(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7148(9) . ?
S1 C2 1.7206(8) . ?
S2 C3 1.7161(8) . ?
S2 C4 1.7154(10) . ?
S3 O1 1.4950(10) . ?
S3 C5 1.8185(9) . ?
S3 C9 1.8263(8) . ?
C1 H1 0.9500 . ?
C1 C7 1.3831(13) . ?
C2 C3 1.4503(11) . ?
C2 C6 1.3785(11) . ?
C3 C8 1.3826(11) . ?
C4 H4 0.9500 . ?
C4 C10 1.3869(14) . ?
C5 H5AA 0.9900 . ?
C5 H5AB 0.9900 . ?
C5 H5BC 0.9900 . ?
C5 H5BD 0.9900 . ?
C5 C6 1.4940(11) . ?
C5 S3A 1.905(9) . ?
C6 C7 1.4230(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.4946(11) . ?
C8 C10 1.4227(12) . ?
C9 H9AA 0.9900 . ?
C9 H9AB 0.9900 . ?
C9 H9BC 0.9900 . ?
C9 H9BD 0.9900 . ?
C9 S3A 1.841(9) . ?
C10 H10 0.9500 . ?
O1A S3A 1.483(16) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C7 C6 0.22(9) . . . . ?
S1 C2 C3 S2 -48.15(9) . . . . ?
S1 C2 C3 C8 133.71(7) . . . . ?
S1 C2 C6 C5 173.78(6) . . . . ?
S1 C2 C6 C7 0.36(9) . . . . ?
S2 C3 C8 C9 175.25(6) . . . . ?
S2 C3 C8 C10 0.32(9) . . . . ?
S2 C4 C10 C8 -0.06(10) . . . . ?
S3 C5 C6 C2 74.55(9) . . . . ?
S3 C5 C6 C7 -112.94(8) . . . . ?
O1 S3 C5 C6 70.22(8) . . . . ?
O1 S3 C9 C8 -156.67(7) . . . . ?
C1 S1 C2 C3 -176.97(7) . . . . ?
C1 S1 C2 C6 -0.20(6) . . . . ?
C2 S1 C1 C7 -0.01(7) . . . . ?
C2 C3 C8 C9 -6.39(12) . . . . ?
C2 C3 C8 C10 178.67(7) . . . . ?
C2 C6 C7 C1 -0.37(10) . . . . ?
C3 S2 C4 C10 0.21(7) . . . . ?
C3 C2 C6 C5 -9.42(12) . . . . ?
C3 C2 C6 C7 177.16(7) . . . . ?
C3 C8 C9 S3 76.75(9) . . . . ?
C3 C8 C9 S3A 70.0(4) . . . . ?
C3 C8 C10 C4 -0.16(10) . . . . ?
C4 S2 C3 C2 -178.64(7) . . . . ?
C4 S2 C3 C8 -0.30(6) . . . . ?
C5 S3 C9 C8 -46.07(7) . . . . ?
C5 C6 C7 C1 -173.53(8) . . . . ?
C6 C2 C3 S2 135.46(7) . . . . ?
C6 C2 C3 C8 -42.68(12) . . . . ?
C8 C9 S3A C5 -31.6(5) . . . . ?
C8 C9 S3A O1A 71.7(9) . . . . ?
C9 S3 C5 C6 -37.59(7) . . . . ?
C9 C8 C10 C4 -174.81(8) . . . . ?
C10 C8 C9 S3 -109.09(8) . . . . ?
C10 C8 C9 S3A -115.9(4) . . . . ?
S3A C5 C6 C2 82.7(3) . . . . ?
S3A C5 C6 C7 -104.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306711
