Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters.
Kou, Xuezhen; Shao, Qihang; Ye, Chenghao; Yang, Guoqiang; Zhang, Wanbin; Journal of the American Chemical Society 140 (2018) 7587–7597; doi:10.1021/jacs.8b02865

data_4132288
_publ_section_title
;
 Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered
 Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary
 or Two Vicinal Stereocenters.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7587
_journal_page_last               7597
_journal_paper_doi               10.1021/jacs.8b02865
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C24 H26 N2 O2 S'
_chemical_formula_sum            'C24 H26 N2 O2 S'
_chemical_formula_weight         406.53
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-07
_audit_creation_method
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Olex2 1.2
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_cell_length_b                   10.510(2)
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_cell_measurement_reflns_used    1487
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -37.00   56.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000    0.0000 93

  2 omega  -17.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  150.0000 98

  3 omega   -5.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0135938000
_diffrn_orient_matrix_UB_12      0.0033059000
_diffrn_orient_matrix_UB_13      0.0448547000
_diffrn_orient_matrix_UB_21      -0.0063851000
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_diffrn_orient_matrix_UB_23      0.0190883000
_diffrn_orient_matrix_UB_31      0.0965327000
_diffrn_orient_matrix_UB_32      -0.0288933000
_diffrn_orient_matrix_UB_33      -0.0109881000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7119
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.887
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.514
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_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.3730P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_number_total             3990
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_chemical_oxdiff_formula         'C H N O S'
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_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C19(H19), C20(H20),
  C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              32344
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_olex2_submission_special_instructions 'No special instructions were received'