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_4132290
_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_absolute_configuration ad
_chemical_formula_moiety         ' C24 H24 N2 O3 S'
_chemical_formula_sum            'C24 H24 N2 O3 S'
_chemical_formula_weight         420.51
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 104.2210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6237(3)
_cell_length_b                   13.4549(4)
_cell_length_c                   13.8736(4)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.55
_cell_measurement_theta_min      3.29
_cell_volume                     2103.28(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24920
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.606
_diffrn_reflns_theta_max         66.605
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_correction_T_min  0.9034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             1596
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0392
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                6716
_reflns_number_total             7349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02865_si_006.cif
_cod_data_source_block           180122HG_KXZ_0m_b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        ' C24 H24 N2 O3 S'
_cod_database_code               4132290
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              59771
_shelx_hkl_checksum              56187