Access to Multisubstituted Furan-3-carbothioates via Cascade Annulation of α-Oxo Ketene Dithioacetals with Isoindoline-1,3-dione-Derived Propargyl Alcohols.
Bai, Li-Gang; Chen, Ming-Tao; Xiao, Dong-Rong; Zhao, Liu-Bin; Luo, Qun-Li; The Journal of organic chemistry 83 (2018) 7648–7658; doi:10.1021/acs.joc.8b00401

data_4035576
_publ_section_title
;
 Access to Multisubstituted Furan-3-carbothioates via Cascade Annulation
 of \a-Oxo Ketene Dithioacetals with Isoindoline-1,3-dione-Derived
 Propargyl Alcohols.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7648
_journal_page_last               7658
_journal_paper_doi               10.1021/acs.joc.8b00401
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29 H25 N O3 S'
_chemical_formula_sum            'C29 H25 N O3 S'
_chemical_formula_weight         467.56
_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
_audit_creation_date             2017-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                100.205(3)
_cell_angle_beta                 108.698(3)
_cell_angle_gamma                106.474(3)
_cell_formula_units_Z            10
_cell_length_a                   15.9281(5)
_cell_length_b                   17.8665(6)
_cell_length_c                   24.3461(9)
_cell_measurement_reflns_used    8969
_cell_measurement_temperature    290.89(10)
_cell_measurement_theta_max      71.3850
_cell_measurement_theta_min      5.6160
_cell_volume                     6013.0(4)
_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      air
_diffrn_ambient_temperature      290.89(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega   10.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000   90.0000 94

  2 omega  -31.00   63.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -77.0000  -30.0000 94

  3 omega   57.00  109.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000  -30.0000 52

  4 omega  -31.00   53.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000 -120.0000 84

  5 omega    1.00   76.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000 -150.0000 75

  6 omega   18.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   38.0000  -30.0000 88

  7 omega   57.00  109.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000  150.0000 52

  8 omega   10.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  150.0000 94

  9 omega   18.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   38.0000   60.0000 88

 10 omega    3.00   32.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   90.0000  -27.0339 29

 11 omega   18.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   38.0000  -90.0000 88

 12 omega    2.00   29.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   91.0000  113.5574 27

 13 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 14 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 15 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 16 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000  150.0000 78

 17 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 18 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 19 omega   39.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 138

 20 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 21 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 22 omega   81.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 23 omega   39.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   60.0000 71

 24 omega   91.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 25 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 26 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000  -60.0000 78

 27 omega   39.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000 -180.0000 71

 28 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 29 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 30 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000    0.0000 78

 31 omega   40.00  135.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 95

 32 omega   40.00  135.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

 33 omega   10.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000   60.0000 94

 34 omega    3.00   32.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   90.0000 -139.7327 29

 35 omega  -32.00   56.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -38.0000  150.0000 88

 36 omega  -31.00   53.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000   90.0000 84

 37 omega  -31.00   63.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -77.0000   30.0000 94

 38 omega   18.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   38.0000 -180.0000 88

 39 omega   20.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000  -60.0000 84

 40 omega   20.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000 -150.0000 84

 41 omega   10.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -60.0000 94

 42 omega   81.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 51

 43 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

 44 omega   70.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_UB_11      -0.0580736000
_diffrn_orient_matrix_UB_12      0.0150700000
_diffrn_orient_matrix_UB_13      -0.0582242000
_diffrn_orient_matrix_UB_21      -0.0561304000
_diffrn_orient_matrix_UB_22      0.0323765000
_diffrn_orient_matrix_UB_23      0.0330978000
_diffrn_orient_matrix_UB_31      0.0742073000
_diffrn_orient_matrix_UB_32      0.0870702000
_diffrn_orient_matrix_UB_33      0.0200729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            84059
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.013
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43774
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             2460
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1542
_refine_ls_number_reflns         21268
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.1920
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2657
_refine_ls_wR_factor_ref         0.4348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             21268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00401_si_002.cif
_cod_data_source_block           lql-20160504
_cod_database_code               4035576
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_reflns_odcompleteness_completeness 99.94
_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. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C103) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C16(H16), C76(H76), C106(H106), C46(H46), C136(H136)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C24(H24A,H24B), C62(H62A,H62B), C84(H84A,H84B), C92(H92A,H92B),
 C114(H11A,H11B), C32(H32A,H32B), C54(H54A,H54B), C122(H12D,H12E), C144(H14A,
 H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20),
 C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C71(H71),
  C72(H72), C73(H73), C74(H74), C75(H75), C79(H79), C80(H80), C81(H81),
 C82(H82), C86(H86), C87(H87), C88(H88), C89(H89), C90(H90), C101(H101),
 C102(H102), C103(H103), C104(H104), C105(H105), C109(H109), C110(H110),
 C111(H111), C112(H112), C116(H116), C117(H117), C118(H118), C119(H119),
 C120(H120), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C49(H49),
 C50(H50), C51(H51), C52(H52), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60),
  C131(H131), C132(H132), C133(H133), C134(H134), C135(H135), C139(H139),
 C140(H140), C141(H141), C142(H142), C146(H146), C147(H147), C148(H148),
 C149(H149), C150(H150)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C61(H61A,H61B,H61C), C69(H69A,H69B,H69C),
 C91(H91A,H91B,H91C), C99(H99A,H99B,H99C), C31(H31A,H31B,H31C), C39(H39A,H39B,
 H39C), C121(H12A,H12B,H12C), C129(H12F,H12G,H12H)
;
_olex2_submission_special_instructions 'No special instructions were received'