Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of Oxindoles and Benzofuran-2(3H)-ones.
Huang, Lisha; Li, Jiangtao; Zhao, Yan; Ye, Xinyi; Liu, Yang; Yan, Lin; Tan, Choon-Hong; Liu, Hongjun; Jiang, Zhiyong; The Journal of organic chemistry 80 (2015) 8933–8941; doi:10.1021/acs.joc.5b01606

data_4036336
_publ_section_title
;
 Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of
 Oxindoles and Benzofuran-2(3H)-ones.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8933
_journal_page_last               8941
_journal_paper_doi               10.1021/acs.joc.5b01606
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration s
_chemical_formula_moiety         'C22 H18 O2 S'
_chemical_formula_sum            'C22 H18 O2 S'
_chemical_formula_weight         346.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
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_cell_length_a                   8.2262(3)
_cell_length_b                   13.4475(5)
_cell_length_c                   8.5887(5)
_cell_measurement_reflns_used    3102
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1260
_cell_measurement_theta_min      5.2890
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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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)
;
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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)
;
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;
  1 omega  -58.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   40.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega -113.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -29.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega -114.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000   60.0000 77

  6 omega  -66.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega -114.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -45.0000  150.0000 94

  8 omega   18.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   47.00  107.00   1.0000    1.0000
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 10 omega   13.00   62.00   1.0000    1.0000
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    -       56.0000  -99.0000   90.0000 49

 11 omega   39.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 26

 12 omega   43.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 27

 13 omega   83.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  120.0000 49

 14 omega   41.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 49

 15 omega   57.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 40

 16 omega   39.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 33

 17 omega   42.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 31

 18 omega   44.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 26

 19 omega   65.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -23.0000 51

 20 omega   46.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 32

 21 omega   49.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 40

 22 omega  109.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 69

 23 omega   94.00  142.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -120.0000 48

 24 omega   41.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 57

 25 omega   42.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 65

 26 omega   75.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 55

 27 omega   40.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 67

 28 omega   73.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 95

 29 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 46

 30 omega -113.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000    0.0000 101

 31 omega   26.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -120.0000 100

 32 omega   26.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  120.0000 67

 33 omega  -13.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  120.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      -0.1032511000
_diffrn_orient_matrix_UB_13      -0.0803680000
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6917
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        67.076
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_min  0.69088
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_exptl_absorpt_process_details
;
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.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description
;
;
_exptl_crystal_F_000             364
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_refine_diff_density_min         -0.145
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_refine_ls_abs_structure_details
;
 Flack x determined using 1297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(12)
_refine_ls_extinction_coef       0.0256(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
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_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0357
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.0019P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3010
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            his.cif
_cod_data_source_block           his
_cod_original_cell_volume        919.27(7)
_cod_database_code               4036336
_chemical_oxdiff_formula         C20H20N4O4S1
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.734
_reflns_odcompleteness_completeness 100.00
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_shelx_res_checksum              78579
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_olex2_submission_special_instructions 'No special instructions were received'