Organocatalytic Asymmetric Michael/Hemiketalization/Retro-aldol Reaction of α-Nitroketones with Unsaturated Pyrazolones: Synthesis of 3-Acyloxy Pyrazoles.
Maity, Rajendra; Gharui, Chandan; Sil, Arun K.; Pan, Subhas Chandra; Organic letters 19 (2017) 662–665; doi:10.1021/acs.orglett.6b03823

data_1545216
_publ_section_title
;
 Organocatalytic Asymmetric Michael/Hemiketalization/Retro-aldol Reaction
 of \a-Nitroketones with Unsaturated Pyrazolones: Synthesis of 3-Acyloxy
 Pyrazoles.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              662
_journal_page_last               665
_journal_paper_doi               10.1021/acs.orglett.6b03823
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C25 H20 Cl N3 O4'
_chemical_formula_weight         461.89
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.112(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2043(12)
_cell_length_b                   19.510(3)
_cell_length_c                   12.5785(17)
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.5930
_cell_measurement_theta_min      3.85
_cell_volume                     2216.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7764
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960.0
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         5537
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0995P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                4085
_reflns_number_total             5537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03823_si_002.cif
_cod_data_source_block           exp_3430
_cod_original_cell_volume        2216.5(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1545216