Asymmetric Multicomponent Sulfa-Michael/Mannich Cascade Reaction: Synthetic Access to 1,2-Diamino-3-Organosulfur Compounds and 2-Nitro Allylic Amines.
Hou, Wenduan; Wei, Qi; Liu, Guisheng; Chen, Jing; Guo, Jing; Peng, Yungui; Organic letters 17 (2015) 4870–4873; doi:10.1021/acs.orglett.5b02423

data_1531174
_publ_section_title
;
 Asymmetric Multicomponent Sulfa-Michael/Mannich Cascade Reaction:
 Synthetic Access to 1,2-Diamino-3-Organosulfur Compounds and 2-Nitro
 Allylic Amines.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4870
_journal_page_last               4873
_journal_paper_doi               10.1021/acs.orglett.5b02423
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C28 H26 N2 O4 S2'
_chemical_formula_sum            'C28 H26 N2 O4 S2'
_chemical_formula_weight         519.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.35547(5)
_cell_length_b                   17.35361(13)
_cell_length_c                   27.1840(2)
_cell_measurement_reflns_used    27423
_cell_measurement_temperature    284.46(10)
_cell_measurement_theta_max      71.4990
_cell_measurement_theta_min      5.0890
_cell_volume                     2526.39(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      284.46(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   55.00  109.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203 -178.0000  -90.0000 54

  2 omega   10.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -90.0000 94

  3 omega   20.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000  -60.0000 84

  4 omega  -33.00  106.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203    0.0000  -90.0000 139

  5 omega   10.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000 -150.0000 94

  6 omega  -31.00   53.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000   60.0000 84

  7 omega  -31.00   63.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -77.0000   30.0000 94

  8 omega    1.00   76.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000  -30.0000 75

  9 omega    1.00   76.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000 -180.0000 75

 10 omega   39.00  110.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -90.0000 71

 11 omega   40.00   98.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 12 omega   38.00   91.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 13 omega   40.00   98.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 14 omega   39.00  110.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000    0.0000 71

 15 omega   39.00  110.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000 -180.0000 71

 16 omega   87.00  178.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 17 omega   40.00   98.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 18 omega   38.00  116.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000  -30.0000 78

 19 omega   40.00   98.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 20 omega   40.00   98.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 21 omega   39.00  110.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   90.0000 71

 22 omega   38.00   91.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 23 omega   40.00   98.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 24 omega   39.00  177.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 138

 25 omega   20.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000 -120.0000 84

 26 omega  -35.00   66.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -19.0000  120.0000 101

 27 omega   20.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000   60.0000 84

 28 omega  -32.00   56.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -38.0000 -150.0000 88

 29 omega   10.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000    0.0000 94

 30 omega   20.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000    0.0000 84

 31 omega   20.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000  120.0000 84

 32 omega   18.00  106.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   38.0000  120.0000 88

 33 omega    7.00  108.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   19.0000   90.0000 101

 34 omega   10.00  104.00   1.0000    1.5200
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  150.0000 94

 35 omega   81.00  176.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 36 omega   91.00  176.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 37 omega   87.00  178.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 38 omega   81.00  176.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 95

 39 omega   87.00  178.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 91

 40 omega   81.00  137.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 56

 41 omega   87.00  178.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0595638000
_diffrn_orient_matrix_UB_12      -0.0568763000
_diffrn_orient_matrix_UB_13      -0.0419069000
_diffrn_orient_matrix_UB_21      -0.0017111000
_diffrn_orient_matrix_UB_22      -0.0671715000
_diffrn_orient_matrix_UB_23      0.0370629000
_diffrn_orient_matrix_UB_31      -0.2813598000
_diffrn_orient_matrix_UB_32      -0.0116408000
_diffrn_orient_matrix_UB_33      -0.0090866000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            37605
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.748
_diffrn_reflns_theta_min         5.097
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.6347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0698
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_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4881
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02423_si_003.cif
_cod_data_source_block           pyg_hwd20141030
_cod_depositor_comments
'Adding full bibliography for 1531166--1531174.cif.'
_cod_original_cell_volume        2526.39(3)
_cod_database_code               1531174
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 N1 H1 O1 S1'
_reflns_odcompleteness_completeness 99.81
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C22(H22), C32(H32), C2(H2), C30(H30), C28(H28), C6(H6), C21(H21),
 C34(H34), C27(H27), C19(H19), C36(H36), C35(H35), C23(H23), C26(H26), C5(H5),
 C3(H3), C33(H33), C20(H20)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'