Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones
Crotti, Simone; Belletti, Giada; Di Iorio, Nicola; Marotta, Emanuela; Mazzanti, Andrea; Righi, Paolo; Bencivenni, Giorgio; RSC Advances 8 (2018) 33451–; doi:10.1039/C8RA06615A

data_7231598
_publ_section_title
;
 Asymmetric vinylogous aldol addition of alkylidene oxindoles on
 trifluoromethyl-\a,\b-unsaturated ketones
;
_journal_issue                   58
_journal_name_full               'RSC Advances'
_journal_page_first              33451
_journal_paper_doi               10.1039/C8RA06615A
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H18 F3 N O2'
_chemical_formula_weight         373.36
_chemical_name_common            'compound 5aa'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             02/21/2018
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   6.515(2)
_cell_length_b                   7.832(2)
_cell_length_c                   36.046(7)
_cell_measurement_reflns_used    528
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.55
_cell_volume                     1839.3(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            9899
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         3.178
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       stick
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   .979
_exptl_transmission_factor_min   .975
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 1253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_coef       0.093(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0308P)^2^+0.2587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3320
_reflns_number_total             3557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra06615a2.cif
_cod_data_source_block           NDI-744_0m_a
_cod_original_cell_volume        1839.0(8)
_cod_database_code               7231598
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              11369
_shelx_hkl_checksum              54274