Chiral Iminophosphorane Catalyzed Asymmetric Sulfenylation of 4-Substituted Pyrazolones
Han, Jianwei; Zhang, Yanxia; Wu, Xin-Yan; Wong, Henry N. C.; Chemical Communications  (2018) –; doi:10.1039/C8CC09049A

data_7122705
_publ_section_title
;
 Chiral Iminophosphorane Catalyzed Asymmetric Sulfenylation of
 4-Substituted Pyrazolones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09049A
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H24 N2 O2 S'
_chemical_formula_weight         464.56
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-11-11 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2478(2)
_cell_length_b                   8.1523(2)
_cell_length_c                   28.2987(6)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.950
_cell_measurement_theta_min      5.201
_cell_volume                     2359.80(9)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            38624
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.991
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 3546 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_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     615
_refine_ls_number_reflns         9155
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.3805P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                8410
_reflns_number_total             9155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09049a2.cif
_cod_data_source_block           mo_d8v17770_0m
_cod_database_code               7122705
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              60091