Dithioallyl cation (3 + 2) cycloadditions under aprotic reaction conditions: rapid access to spiro-fused cyclopentane scaffolds.
Degroote, Frederick; Denoo, Bram; Ryckaert, Bram; Callebaut, Brenda; Van Hecke, Kristof; Hullaert, Jan; Winne, Johan M.; Organic & biomolecular chemistry 21 (2023) 8117–8124; doi:10.1039/d3ob01273e

data_7159577
_publ_section_title
;
 Dithioallyl cation (3 + 2) cycloadditions under aprotic reaction
 conditions: rapid access to spiro-fused cyclopentane scaffolds.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8117
_journal_page_last               8124
_journal_paper_doi               10.1039/d3ob01273e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C17 H26 S2'
_chemical_formula_sum            'C17 H26 S2'
_chemical_formula_weight         294.50
_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     direct
_audit_creation_date             2015-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.644(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1865(3)
_cell_length_b                   8.18900(17)
_cell_length_c                   19.2034(4)
_cell_measurement_reflns_used    13677
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.9090
_cell_measurement_theta_min      4.3350
_cell_volume                     1591.14(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -84.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  101.0000  150.0000 102

  2 omega    4.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048 -101.0000   46.0000 80

  3 omega   29.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -101.0000   46.0000 82

  4 omega  101.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  101.0000  150.0000 77

  5 omega  -50.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048   38.0000  -90.0000 82

  6 omega  -70.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048   57.0000    0.0000 101

  7 omega  -32.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -38.0000  120.0000 98

  8 omega   33.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -77.0000   60.0000 109

  9 omega   33.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000 -180.0000 58

 10 omega   36.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000   60.0000 62

 11 omega   83.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -150.0000 95

 12 omega   37.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -61.0000 -180.0000 101

 13 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000  120.0000 100

 14 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -77.0000  -60.0000 109

 15 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000 -120.0000 100

 16 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -77.0000 -150.0000 109

 17 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000    0.0000 100

 18 omega   81.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000  120.0000 97

 19 omega   56.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   15.0000    0.0000 122

 20 omega   36.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000   30.0000 85

 21 omega   81.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000   60.0000 97

 22 omega   77.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000 -120.0000 101

 23 omega -116.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -38.0000 -120.0000 99

 24 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -77.0000   90.0000 109

 25 omega    9.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   77.0000   90.0000 109

 26 omega    9.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   77.0000 -180.0000 109

 27 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   38.0000  -90.0000 99

 28 omega   80.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  150.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0676924000
_diffrn_orient_matrix_UB_12      -0.0259761000
_diffrn_orient_matrix_UB_13      -0.0751787000
_diffrn_orient_matrix_UB_21      0.0317101000
_diffrn_orient_matrix_UB_22      0.1777888000
_diffrn_orient_matrix_UB_23      -0.0182726000
_diffrn_orient_matrix_UB_31      0.1326046000
_diffrn_orient_matrix_UB_32      -0.0557809000
_diffrn_orient_matrix_UB_33      -0.0232441000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23284
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.336
_diffrn_reflns_theta_min         4.370
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.887
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2357
_exptl_crystal_size_mid          0.2172
_exptl_crystal_size_min          0.0999
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0295
_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/[\s^2^(Fo^2^)+(0.0436P)^2^+0.6390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3047
_reflns_number_total             3250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01273e2.cif
_cod_data_source_block           jw002
_cod_depositor_comments          'Adding full bibliography for 7159577.cif.'
_cod_database_code               7159577
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C17 H26 S2'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              31685
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'