Organocatalytic Enantioselective Aminoalkylation of Pyrazol-3-ones with Aldimines Generated in Situ from α‐Amido Sulfones
Carceller-Ferrer, Laura; Vila, Carlos; Blay, Gonzalo; Fernández, Isabel; Muñoz, M. Carmen; Pedro, Jose R.; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02252J

data_7157190
_publ_section_title
;
 Organocatalytic Enantioselective Aminoalkylation of Pyrazol-3-ones with
 Aldimines Generated in Situ from \a&#x2010;Amido Sulfones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02252J
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H28 N3 O5'
_chemical_formula_weight         486.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-07-31 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.465(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.8739(8)
_cell_length_b                   5.10500(10)
_cell_length_c                   14.1957(3)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.35
_cell_measurement_theta_min      2.621
_cell_volume                     2443.65(9)
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_collection       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36003
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.605
_diffrn_reflns_theta_min         2.621
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0767P)^2^+1.3123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4343
_reflns_number_total             4833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02252j2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7157190
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014-1
_shelx_res_checksum              66142
_shelx_hkl_checksum              64298