#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:47:33 +0300 (Mon, 04 May 2020) $
#$Revision: 251484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038278.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_4038278
loop_
_publ_author_name
'Sundaravelu, Nallappan'
'Guha, Somraj'
'Sekar, Govindasamy'
_publ_section_title
;
 Iodonium Ion-Catalyzed Domino Synthesis of Z-Selective
 α,β-Diphenylthio Enones from Easily Accessible Secondary Alcohols.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5895
_journal_page_last               5906
_journal_paper_doi               10.1021/acs.joc.0c00183
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C21 H12 Cl2 O S2'
_chemical_formula_sum            'C21 H12 Cl2 O S2'
_chemical_formula_weight         415.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                72.0273(13)
_cell_angle_beta                 79.5744(13)
_cell_angle_gamma                77.9792(13)
_cell_formula_units_Z            2
_cell_length_a                   8.2801(3)
_cell_length_b                   10.9055(4)
_cell_length_c                   11.3166(3)
_cell_measurement_reflns_used    6987
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.96
_cell_volume                     943.19(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_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       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13086
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.990
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       Block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0369
_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)+(0.0374P)²+0.6144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2777
_reflns_number_total             3260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00183_si_003.cif
_cod_data_source_block           295
_cod_depositor_comments
'Adding full bibliography for 4038277--4038278.cif.'
_cod_database_code               4038278
_shelx_shelxl_version_number     2014/7
_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_min   0.856
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.1586(2) 0.1356(2) 0.40292(18) 0.0378(5) Uani 1 1 d . . . . .
C2 C -0.0246(3) 0.1823(2) 0.40648(19) 0.0397(5) Uani 1 1 d . . . . .
C3 C -0.1452(3) 0.2140(2) 0.4978(2) 0.0499(5) Uani 1 1 d . . . . .
H3 H -0.1190 0.2086 0.5759 0.060 Uiso 1 1 calc R U . . .
C4 C -0.3092(3) 0.2549(3) 0.4689(3) 0.0636(7) Uani 1 1 d . . . . .
H4 H -0.3931 0.2766 0.5293 0.076 Uiso 1 1 calc R U . . .
C5 C -0.3490(3) 0.2636(3) 0.3530(3) 0.0667(7) Uani 1 1 d . . . . .
H5 H -0.4583 0.2929 0.3358 0.080 Uiso 1 1 calc R U . . .
C6 C -0.2279(3) 0.2292(3) 0.2622(3) 0.0585(6) Uani 1 1 d . . . . .
H6 H -0.2543 0.2341 0.1842 0.070 Uiso 1 1 calc R U . . .
C7 C -0.0676(3) 0.1874(2) 0.2906(2) 0.0450(5) Uani 1 1 d . . . . .
C8 C 0.0825(3) 0.1358(2) 0.21606(19) 0.0459(5) Uani 1 1 d . . . . .
C9 C 0.2207(3) 0.1116(2) 0.29174(19) 0.0425(5) Uani 1 1 d . . . . .
C10 C 0.1929(3) 0.2046(2) 0.61352(18) 0.0402(5) Uani 1 1 d . . . . .
C11 C 0.1834(3) 0.3380(2) 0.5637(2) 0.0586(6) Uani 1 1 d . . . . .
H11 H 0.2163 0.3729 0.4789 0.070 Uiso 1 1 calc R U . . .
C12 C 0.1253(4) 0.4194(3) 0.6391(3) 0.0705(8) Uani 1 1 d . . . . .
H12 H 0.1178 0.5094 0.6056 0.085 Uiso 1 1 calc R U . . .
C13 C 0.0786(3) 0.3661(3) 0.7645(3) 0.0638(7) Uani 1 1 d . . . . .
C14 C 0.0884(3) 0.2340(3) 0.8158(2) 0.0616(7) Uani 1 1 d . . . . .
H14 H 0.0570 0.1994 0.9010 0.074 Uiso 1 1 calc R U . . .
C15 C 0.1454(3) 0.1531(2) 0.73970(19) 0.0474(5) Uani 1 1 d . . . . .
H15 H 0.1519 0.0631 0.7735 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4765(3) 0.1548(2) 0.10179(19) 0.0423(5) Uani 1 1 d . . . . .
C17 C 0.6015(3) 0.1079(2) 0.0197(2) 0.0481(5) Uani 1 1 d . . . . .
H17 H 0.6522 0.0209 0.0423 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6511(3) 0.1895(3) -0.0950(2) 0.0561(6) Uani 1 1 d . . . . .
H18 H 0.7363 0.1586 -0.1496 0.067 Uiso 1 1 calc R U . . .
C19 C 0.5736(3) 0.3167(3) -0.1280(2) 0.0574(6) Uani 1 1 d . . . . .
C20 C 0.4498(3) 0.3657(3) -0.0477(3) 0.0597(6) Uani 1 1 d . . . . .
H20 H 0.3988 0.4526 -0.0712 0.072 Uiso 1 1 calc R U . . .
C21 C 0.4027(3) 0.2843(2) 0.0681(2) 0.0535(6) Uani 1 1 d . . . . .
H21 H 0.3208 0.3168 0.1238 0.064 Uiso 1 1 calc R U . . .
Cl1 Cl 0.00430(15) 0.46877(11) 0.86024(11) 0.1165(4) Uani 1 1 d . . . . .
Cl2 Cl 0.63275(13) 0.41831(9) -0.27579(8) 0.0981(3) Uani 1 1 d . . . . .
O1 O 0.0897(2) 0.1117(2) 0.11724(15) 0.0667(5) Uani 1 1 d . . . . .
S1 S 0.28165(7) 0.09522(6) 0.52199(5) 0.05125(18) Uani 1 1 d . . . . .
S2 S 0.42447(7) 0.04353(6) 0.24919(5) 0.05169(18) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 109.63(18) . . ?
C9 C1 S1 120.96(16) . . ?
C2 C1 S1 128.97(15) . . ?
C3 C2 C7 120.2(2) . . ?
C3 C2 C1 132.8(2) . . ?
C7 C2 C1 107.01(19) . . ?
C2 C3 C4 117.7(2) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.0(2) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 121.9(2) . . ?
C6 C7 C8 129.5(2) . . ?
C2 C7 C8 108.57(18) . . ?
O1 C8 C7 127.4(2) . . ?
O1 C8 C9 127.1(2) . . ?
C7 C8 C9 105.38(18) . . ?
C1 C9 C8 109.15(19) . . ?
C1 C9 S2 126.28(16) . . ?
C8 C9 S2 124.12(16) . . ?
C11 C10 C15 119.7(2) . . ?
C11 C10 S1 121.62(17) . . ?
C15 C10 S1 118.43(17) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 Cl1 119.2(2) . . ?
C12 C13 Cl1 119.4(2) . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C21 C16 C17 119.6(2) . . ?
C21 C16 S2 123.27(17) . . ?
C17 C16 S2 117.13(18) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 Cl2 119.0(2) . . ?
C20 C19 Cl2 119.6(2) . . ?
C19 C20 C21 119.1(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C16 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C1 S1 C10 105.26(10) . . ?
C9 S2 C16 102.02(10) . . ?
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
C1 C9 1.352(3) . ?
C1 C2 1.493(3) . ?
C1 S1 1.730(2) . ?
C2 C3 1.374(3) . ?
C2 C7 1.401(3) . ?
C3 C4 1.403(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.482(3) . ?
C8 O1 1.214(3) . ?
C8 C9 1.484(3) . ?
C9 S2 1.742(2) . ?
C10 C11 1.379(3) . ?
C10 C15 1.380(3) . ?
C10 S1 1.777(2) . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(4) . ?
C13 Cl1 1.739(3) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.381(3) . ?
C16 C17 1.386(3) . ?
C16 S2 1.775(2) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 Cl2 1.747(3) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
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
C9 C1 C2 C3 176.8(2) . . . . ?
S1 C1 C2 C3 4.5(4) . . . . ?
C9 C1 C2 C7 -1.2(2) . . . . ?
S1 C1 C2 C7 -173.54(17) . . . . ?
C7 C2 C3 C4 -1.9(3) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C2 -1.6(4) . . . . ?
C5 C6 C7 C8 174.9(2) . . . . ?
C3 C2 C7 C6 2.9(3) . . . . ?
C1 C2 C7 C6 -178.8(2) . . . . ?
C3 C2 C7 C8 -174.3(2) . . . . ?
C1 C2 C7 C8 4.0(2) . . . . ?
C6 C7 C8 O1 -5.7(4) . . . . ?
C2 C7 C8 O1 171.2(2) . . . . ?
C6 C7 C8 C9 177.9(2) . . . . ?
C2 C7 C8 C9 -5.2(2) . . . . ?
C2 C1 C9 C8 -2.1(2) . . . . ?
S1 C1 C9 C8 170.92(15) . . . . ?
C2 C1 C9 S2 -174.60(16) . . . . ?
S1 C1 C9 S2 -1.6(3) . . . . ?
O1 C8 C9 C1 -171.9(2) . . . . ?
C7 C8 C9 C1 4.5(2) . . . . ?
O1 C8 C9 S2 0.8(4) . . . . ?
C7 C8 C9 S2 177.16(16) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
S1 C10 C11 C12 -175.2(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C11 C12 C13 Cl1 -179.8(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
Cl1 C13 C14 C15 179.3(2) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
C11 C10 C15 C14 0.1(4) . . . . ?
S1 C10 C15 C14 174.86(19) . . . . ?
C21 C16 C17 C18 -0.5(3) . . . . ?
S2 C16 C17 C18 -178.46(18) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C17 C18 C19 Cl2 -178.01(19) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
Cl2 C19 C20 C21 179.2(2) . . . . ?
C19 C20 C21 C16 -1.3(4) . . . . ?
C17 C16 C21 C20 1.7(4) . . . . ?
S2 C16 C21 C20 179.53(19) . . . . ?
C9 C1 S1 C10 153.75(18) . . . . ?
C2 C1 S1 C10 -34.7(2) . . . . ?
C11 C10 S1 C1 -61.5(2) . . . . ?
C15 C10 S1 C1 123.87(18) . . . . ?
C1 C9 S2 C16 -130.3(2) . . . . ?
C8 C9 S2 C16 58.3(2) . . . . ?
C21 C16 S2 C9 26.2(2) . . . . ?
C17 C16 S2 C9 -155.97(17) . . . . ?
