#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:11:23 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160368.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_7160368
loop_
_publ_author_name
'Awchar, Vilas M.'
'Baskaran, Sundarababu'
_publ_section_title
;
 Cascade reaction of α-aryl vinyl and propargyl sulfonium salts with
 carbon nucleophiles: synthesis of functionalized benzyl and homoallyl
 thioethers.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2610
_journal_page_last               2614
_journal_paper_doi               10.1039/d5ob00087d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H20 N2 S'
_chemical_formula_sum            'C20 H20 N2 S'
_chemical_formula_weight         320.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-06-16 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.604(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7116(3)
_cell_length_b                   9.0628(5)
_cell_length_c                   34.5624(19)
_cell_measurement_reflns_used    4085
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.36
_cell_volume                     1787.21(17)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            23357
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.180
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0352P)²+0.6137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2113
_reflns_number_total             3154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00087d2.cif
_cod_data_source_block           159
_cod_depositor_comments          'Adding full bibliography for 7160368.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160368
_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   0.961
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.5937(5) 0.1942(3) 0.19003(7) 0.0771(8) Uani 1 1 d . . . . .
H1 H 0.6421 0.1515 0.1673 0.093 Uiso 1 1 calc R U . . .
C2 C 0.4167(6) 0.1293(3) 0.20912(8) 0.0975(10) Uani 1 1 d . . . . .
H2 H 0.3465 0.0438 0.1993 0.117 Uiso 1 1 calc R U . . .
C3 C 0.3435(5) 0.1894(4) 0.24223(9) 0.0868(8) Uani 1 1 d . . . . .
H3 H 0.2206 0.1463 0.2549 0.104 Uiso 1 1 calc R U . . .
C4 C 0.4488(6) 0.3121(3) 0.25695(8) 0.0905(9) Uani 1 1 d . . . . .
H4 H 0.4002 0.3521 0.2800 0.109 Uiso 1 1 calc R U . . .
C5 C 0.6307(5) 0.3794(3) 0.23753(7) 0.0767(8) Uani 1 1 d . . . . .
H5 H 0.7027 0.4637 0.2477 0.092 Uiso 1 1 calc R U . . .
C6 C 0.7025(4) 0.3204(2) 0.20341(6) 0.0524(5) Uani 1 1 d . . . . .
C7 C 0.8916(4) 0.3919(2) 0.18105(6) 0.0554(6) Uani 1 1 d . . . . .
H7A H 0.9846 0.3151 0.1696 0.066 Uiso 1 1 calc R U . . .
H7B H 0.9941 0.4467 0.1990 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8011(3) 0.4979(2) 0.14841(6) 0.0455(5) Uani 1 1 d . . . . .
C9 C 0.6487(4) 0.4175(2) 0.12007(6) 0.0515(5) Uani 1 1 d . . . . .
C10 C 0.6583(4) 0.6170(2) 0.16475(6) 0.0531(5) Uani 1 1 d . . . . .
C11 C 1.0070(3) 0.5646(2) 0.12698(6) 0.0533(5) Uani 1 1 d . . . . .
H11A H 1.1125 0.6133 0.1457 0.064 Uiso 1 1 calc R U . . .
H11B H 1.0931 0.4854 0.1152 0.064 Uiso 1 1 calc R U . . .
C12 C 0.9312(4) 0.6754(3) 0.09560(7) 0.0650(6) Uani 1 1 d . . . . .
H12A H 0.8047 0.6329 0.0796 0.078 Uiso 1 1 calc R U . . .
H12B H 0.8713 0.7632 0.1078 0.078 Uiso 1 1 calc R U . . .
C13 C 1.1273(4) 0.7190(2) 0.07017(6) 0.0515(5) Uani 1 1 d . . . . .
C14 C 1.2670(3) 0.8425(2) 0.07717(6) 0.0496(5) Uani 1 1 d . . . . .
C15 C 1.4414(4) 0.8738(3) 0.05166(8) 0.0747(7) Uani 1 1 d . . . . .
H15 H 1.5361 0.9562 0.0560 0.090 Uiso 1 1 calc R U . . .
C16 C 1.4767(6) 0.7852(4) 0.02013(9) 0.1013(11) Uani 1 1 d . . . . .
H16 H 1.5933 0.8085 0.0032 0.122 Uiso 1 1 calc R U . . .
C17 C 1.3422(7) 0.6646(4) 0.01376(8) 0.1047(12) Uani 1 1 d . . . . .
H17 H 1.3667 0.6041 -0.0074 0.126 Uiso 1 1 calc R U . . .
C18 C 1.1708(5) 0.6315(3) 0.03839(7) 0.0800(8) Uani 1 1 d . . . . .
H18 H 1.0800 0.5477 0.0338 0.096 Uiso 1 1 calc R U . . .
C19 C 1.2355(4) 0.9444(3) 0.11052(7) 0.0689(7) Uani 1 1 d . . . . .
H19A H 1.3762 1.0036 0.1143 0.083 Uiso 1 1 calc R U . . .
H19B H 1.2198 0.8856 0.1337 0.083 Uiso 1 1 calc R U . . .
C20 C 1.0371(5) 1.1540(3) 0.06046(7) 0.0827(8) Uani 1 1 d . . . . .
H20A H 1.1844 1.2050 0.0623 0.124 Uiso 1 1 calc R U . . .
H20B H 0.9135 1.2232 0.0544 0.124 Uiso 1 1 calc R U . . .
H20C H 1.0406 1.0809 0.0404 0.124 Uiso 1 1 calc R U . . .
N1 N 0.5382(4) 0.3556(2) 0.09738(6) 0.0757(6) Uani 1 1 d . . . . .
N2 N 0.5505(4) 0.7095(2) 0.17705(6) 0.0756(6) Uani 1 1 d . . . . .
S1 S 0.98644(12) 1.06674(7) 0.10534(2) 0.0761(2) 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'
N N 0.0061 0.0033 '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
C2 C1 C6 122.0(2) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 117.7(2) . . ?
C1 C6 C7 120.7(2) . . ?
C5 C6 C7 121.5(2) . . ?
C6 C7 C8 114.65(16) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C10 107.15(16) . . ?
C9 C8 C11 108.38(17) . . ?
C10 C8 C11 110.05(17) . . ?
C9 C8 C7 110.14(16) . . ?
C10 C8 C7 110.17(17) . . ?
C11 C8 C7 110.86(15) . . ?
N1 C9 C8 177.5(2) . . ?
N2 C10 C8 179.1(3) . . ?
C12 C11 C8 113.69(16) . . ?
C12 C11 H11A 108.8 . . ?
C8 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C8 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.13(18) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C18 C13 C14 118.5(2) . . ?
C18 C13 C12 118.5(2) . . ?
C14 C13 C12 123.1(2) . . ?
C15 C14 C13 118.4(2) . . ?
C15 C14 C19 118.6(2) . . ?
C13 C14 C19 122.95(19) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 122.0(3) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
C14 C19 S1 115.13(15) . . ?
C14 C19 H19A 108.5 . . ?
S1 C19 H19A 108.5 . . ?
C14 C19 H19B 108.5 . . ?
S1 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 S1 C19 101.61(12) . . ?
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 C2 1.365(3) . ?
C1 C6 1.371(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.351(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 C8 1.552(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.473(3) . ?
C8 C10 1.480(3) . ?
C8 C11 1.541(3) . ?
C9 N1 1.132(3) . ?
C10 N2 1.134(3) . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.386(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.494(3) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.348(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 S1 1.806(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 S1 1.776(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
C1 C6 C7 C8 84.6(3) . . . . ?
C5 C6 C7 C8 -94.6(2) . . . . ?
C6 C7 C8 C9 -59.6(2) . . . . ?
C6 C7 C8 C10 58.4(2) . . . . ?
C6 C7 C8 C11 -179.54(18) . . . . ?
C9 C8 C11 C12 61.6(2) . . . . ?
C10 C8 C11 C12 -55.3(2) . . . . ?
C7 C8 C11 C12 -177.45(18) . . . . ?
C8 C11 C12 C13 -169.60(18) . . . . ?
C11 C12 C13 C18 86.1(3) . . . . ?
C11 C12 C13 C14 -93.7(2) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C12 C13 C14 C15 -179.3(2) . . . . ?
C18 C13 C14 C19 180.0(2) . . . . ?
C12 C13 C14 C19 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C19 C14 C15 C16 -179.1(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C13 0.4(4) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
C12 C13 C18 C17 179.1(2) . . . . ?
C15 C14 C19 S1 104.0(2) . . . . ?
C13 C14 C19 S1 -75.0(2) . . . . ?
C14 C19 S1 C20 -54.6(2) . . . . ?
