Direct Regioselective [3 + 2]-Cyclization Reactions of Ambivalent Electrophilic/Nucleophilic β-Chlorovinyl Dithianes: Access to Cyclopentene Derivatives.
Liang, Yongping; Lai, Junshan; Liu, Teng; Tang, Shouchu; Organic letters 18 (2016) 5086–5089; doi:10.1021/acs.orglett.6b02536

data_1555814
_publ_section_title
;
 Direct Regioselective [3 + 2]-Cyclization Reactions of Ambivalent
 Electrophilic/Nucleophilic \b-Chlorovinyl Dithianes: Access to
 Cyclopentene Derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5086
_journal_page_last               5089
_journal_paper_doi               10.1021/acs.orglett.6b02536
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C27 H24 O S2'
_chemical_formula_sum            'C27 H24 O S2'
_chemical_formula_weight         428.58
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                79.629(14)
_cell_angle_beta                 69.436(15)
_cell_angle_gamma                72.515(14)
_cell_formula_units_Z            2
_cell_length_a                   9.7091(15)
_cell_length_b                   10.2062(17)
_cell_length_c                   12.300(2)
_cell_measurement_reflns_used    2677
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.5020
_cell_measurement_theta_min      3.6620
_cell_volume                     1084.7(3)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N2
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -22.00   90.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   19.0000  -60.0000 56

  2 omega   16.00   50.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -77.0000 -120.0000 17

  3 omega  -20.00   54.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000    0.0000 37

  4 omega  -15.00   23.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  120.0000 19

  5 omega  -47.00   35.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  120.0000 41

  6 omega   50.00   94.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000  150.0000 22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0113053000
_diffrn_orient_matrix_UB_12      0.0554908000
_diffrn_orient_matrix_UB_13      0.0322502000
_diffrn_orient_matrix_UB_21      0.0370336000
_diffrn_orient_matrix_UB_22      -0.0461965000
_diffrn_orient_matrix_UB_23      0.0376952000
_diffrn_orient_matrix_UB_31      0.0708629000
_diffrn_orient_matrix_UB_32      0.0115333000
_diffrn_orient_matrix_UB_33      -0.0368616000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7488
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94117
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0424
_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/[\s^2^(Fo^2^)+(0.0302P)^2^+0.2481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                3326
_reflns_number_total             4273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02536_si_003.cif
_cod_data_source_block           tangshcu_1208
_cod_database_code               1555814
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_date_sample_data_collection 2015-12-09
_olex2_submission_special_instructions 'No special instructions were received'