Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene Derivatives via Base-Catalyzed Cascade Michael-Aldol [3 + 2] Annulation of 1,4-Dithiane-2,5-diol with Maleimides.
Zhong, Yuan; Ma, Shixiong; Li, Bai; Jiang, Xianxing; Wang, Rui; The Journal of organic chemistry 80 (2015) 6870–6874; doi:10.1021/acs.joc.5b00897

data_4031103
_publ_section_title
;
 Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene
 Derivatives via Base-Catalyzed Cascade Michael-Aldol [3 + 2] Annulation
 of 1,4-Dithiane-2,5-diol with Maleimides.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6870
_journal_page_last               6874
_journal_paper_doi               10.1021/acs.joc.5b00897
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H15 N O3 S'
_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_weight         325.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.772
_diffrn_measured_fraction_theta_max 0.772
_diffrn_measurement_details
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  1 omega   -9.00   51.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   77.0000  -90.0000 60

  2 omega  -48.00   14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -60.0000 62

  3 omega  -42.00   38.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000   60.0000 80

  4 omega   63.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  178.0000  120.0000 31

  5 omega   -7.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000   30.0000 59
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0708448000
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_diffrn_orient_matrix_UB_21      0.0241563000
_diffrn_orient_matrix_UB_22      0.0348210000
_diffrn_orient_matrix_UB_23      0.0279630000
_diffrn_orient_matrix_UB_31      -0.0150405000
_diffrn_orient_matrix_UB_32      -0.0319198000
_diffrn_orient_matrix_UB_33      0.0372670000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6693
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.220
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
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_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             680
_refine_diff_density_max         0.161
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_refine_ls_extinction_method     none
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'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.0946P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_data_source_file            jo5b00897_si_002.cif
_cod_data_source_block           mashx0107
_cod_depositor_comments
'Adding full bibliography for 4031102--4031104.cif.'
_cod_original_cell_volume        1572.01(19)
_cod_database_code               4031103
_reflns_odcompleteness_completeness 80.35
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_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 Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C28(H28), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_olex2_date_sample_data_collection 2015-01-08
_olex2_submission_special_instructions 'No special instructions were received'