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_1555815
_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      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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.2330(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4129(3)
_cell_length_b                   9.30538(16)
_cell_length_c                   15.7040(3)
_cell_measurement_reflns_used    3543
_cell_measurement_temperature    291.48(10)
_cell_measurement_theta_max      69.6360
_cell_measurement_theta_min      5.8100
_cell_volume                     2223.13(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.48(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega   55.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 62

  2 omega   88.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 32

  3 omega   85.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -30.0000 28

  4 omega   44.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 49

  5 omega   35.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 59

  6 omega   40.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 51

  7 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 26

  8 omega   35.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 59

  9 omega   49.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -60.0000 88

 10 omega   44.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 60

 11 omega   38.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 66

 12 omega   49.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 38

 13 omega   32.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -30.0000 30

 14 omega    1.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 67

 15 omega  -17.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  150.0000 31

 16 omega  -18.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 75
;
_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      0.0589742000
_diffrn_orient_matrix_UB_12      -0.0192096000
_diffrn_orient_matrix_UB_13      0.0882206000
_diffrn_orient_matrix_UB_21      0.0805580000
_diffrn_orient_matrix_UB_22      0.0473776000
_diffrn_orient_matrix_UB_23      -0.0397062000
_diffrn_orient_matrix_UB_31      -0.0170898000
_diffrn_orient_matrix_UB_32      0.1574602000
_diffrn_orient_matrix_UB_33      0.0226833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7559
_diffrn_reflns_theta_full        69.76
_diffrn_reflns_theta_max         69.76
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.5176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                3540
_reflns_number_total             4077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02536_si_002.cif
_cod_data_source_block           tangshch0916_1
_cod_original_cell_volume        2223.14(7)
_cod_database_code               1555815
_reflns_odcompleteness_completeness 98.42
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C20(H20), C8(H8), C3(H3), C21(H21), C11(H11), C14(H14),
 C24(H24), C10(H10), C23(H23), C16(H16), C18(H18), C17(H17), C22(H22), C9(H9),
 C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'