Asymmetric cross-aldol reaction of α-keto hydrazones and α,β-unsaturated γ-keto hydrazones with trifluoromethyl ketones
Alberca, Saul; Matador, Esteban; Iglesias-Sigüenza, Javier; Retamosa, Maria de Gracia; Fernández, Rosario; Lassaletta, Jose M.; Monge, David; Chemical Communications  (2021) –; doi:10.1039/D1CC05014A

data_7129121
_publ_section_title
;
 Asymmetric cross-aldol reaction of \a-keto hydrazones and
 \a,\b-unsaturated \g-keto hydrazones with trifluoromethyl ketones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05014A
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H17 F3 N2 O2'
_chemical_formula_weight         350.33
_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-2018/1
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.836(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0402(5)
_cell_length_b                   6.9374(3)
_cell_length_c                   11.4994(5)
_cell_measurement_reflns_used    3803
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.77
_cell_measurement_theta_min      6.84
_cell_volume                     828.49(6)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5218
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        65.751
_diffrn_reflns_theta_max         65.751
_diffrn_reflns_theta_min         6.839
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       Prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.13(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.663
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.663
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_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^+0.5844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_full    0.484
_reflns_Friedel_fraction_max     0.484
_reflns_number_gt                2152
_reflns_number_total             2156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05014a2.cif
_cod_data_source_block           igl1120
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129121
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.744
_shelx_estimated_absorpt_t_max   0.917
_shelx_res_checksum              11081