Asymmetric Michael Addition Induced by (R)-tert-Butanesulfinamide and Syntheses of Chiral Pyrazolidinone Derivatives.
Huang, Hong-Xiu; Wang, Hui-Jing; Tan, Ling; Wang, Shu-Qing; Tang, Pei; Song, Hao; Liu, Xiao-Yu; Zhang, Dan; Qin, Yong; The Journal of organic chemistry 81 (2016) 10506–10516; doi:10.1021/acs.joc.6b01237

data_4037003
_publ_section_title
;
 Asymmetric Michael Addition Induced by (R)-tert-Butanesulfinamide and
 Syntheses of Chiral Pyrazolidinone Derivatives.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10506
_journal_page_last               10516
_journal_paper_doi               10.1021/acs.joc.6b01237
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H41 N3 O7 S'
_chemical_formula_sum            'C30 H41 N3 O7 S'
_chemical_formula_weight         587.72
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3265(2)
_cell_length_b                   10.1974(3)
_cell_length_c                   38.2435(16)
_cell_measurement_reflns_used    5774
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.5090
_cell_measurement_theta_min      3.2260
_cell_volume                     3247.20(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   0.1000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.3095  -99.0000 -120.0000 490

  2 omega  -49.00   46.00   0.1000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0282  -57.0000  -60.0000 950

  3 omega   -2.00   93.00   0.1000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0282   57.0000   90.0000 950

  4 omega  -25.00   67.00   0.1000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0282  -99.0000 -180.0000 920

  5 omega  -51.00   53.00   0.1000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0282  -38.0000 -180.0000 1040

  6 omega  -44.00  -13.00   0.1000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0282   19.0000  -30.0000 310
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0163368000
_diffrn_orient_matrix_UB_12      0.0376861000
_diffrn_orient_matrix_UB_13      -0.0151980000
_diffrn_orient_matrix_UB_21      0.0135447000
_diffrn_orient_matrix_UB_22      0.0583813000
_diffrn_orient_matrix_UB_23      0.0096333000
_diffrn_orient_matrix_UB_31      0.0824632000
_diffrn_orient_matrix_UB_32      -0.0020329000
_diffrn_orient_matrix_UB_33      -0.0045752000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            26415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.921
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92931
_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_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1136P)^2^+0.6983P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.2072
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4787
_reflns_number_total             6646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01237_si_002.cif
_cod_data_source_block           160114_s2_djm
_cod_original_cell_volume        3247.2(2)
_cod_database_code               4037003
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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(O2A) = Uanis(O2B)
Uanis(O6B) = Uanis(O6A)
Uanis(C15) = Uanis(C16) = Uanis(C17) = Uanis(C18) = Uanis(C19) = Uanis(C20)
3. Others
 Sof(O2B)=1-FVAR(1)
 Sof(O2A)=FVAR(1)
 Sof(O6A)=1-FVAR(2)
 Sof(O6B)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C22(H22)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B), C23(H23A,H23B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C16(H16), C17(H17), C19(H19), C20(H20)
4.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C)
;
_shelx_res_checksum              15986
_shelx_hkl_checksum              78593
_olex2_submission_special_instructions 'No special instructions were received'