Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction.
Yang, Hongzhou; Wang, Qingqing; Luo, Yuan; Ye, Ling; Li, Xinying; Chen, Feng; Zhao, Zhigang; Li, Xuefeng; Organic & biomolecular chemistry 18 (2020) 1607–1611; doi:10.1039/d0ob00004c

data_7157334
_publ_section_title
;
 Enantioselective synthesis of trifluoromethyl substituted cyclohexanones
 via an organocatalytic cascade Michael/aldol reaction.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1607
_journal_page_last               1611
_journal_paper_doi               10.1039/d0ob00004c
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 Cl F3 O4'
_chemical_formula_sum            'C16 H16 Cl F3 O4'
_chemical_formula_weight         364.74
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-23 deposited with the CCDC.	2020-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6493(2)
_cell_length_b                   14.4444(7)
_cell_length_c                   21.6781(9)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    297.60(10)
_cell_measurement_theta_max      71.8670
_cell_measurement_theta_min      6.8480
_cell_volume                     1768.95(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.60(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000    0.0000 84

  2 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -180.0000 95

  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000 -150.0000 84

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -30.0000 84

  5 omega  -32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000  150.0000 95

  6 omega   40.00   98.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

  7 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

  8 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

  9 omega   37.00  146.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 109

 10 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 11 omega   39.00  109.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 12 omega   39.00  109.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 13 omega   40.00   98.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 14 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 15 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -90.0000 84

 16 omega  -31.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -150.0000 53

 17 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  120.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0442818000
_diffrn_orient_matrix_UB_12      0.0660526000
_diffrn_orient_matrix_UB_13      0.0545674000
_diffrn_orient_matrix_UB_21      0.0389951000
_diffrn_orient_matrix_UB_22      -0.0805024000
_diffrn_orient_matrix_UB_23      0.0454744000
_diffrn_orient_matrix_UB_31      0.2663788000
_diffrn_orient_matrix_UB_32      0.0227551000
_diffrn_orient_matrix_UB_33      0.0024274000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9792
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.442
_diffrn_reflns_theta_min         5.102
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details
;
 Flack x determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0765
_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^)+(0.1408P)^2^+0.3350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1951
_refine_ls_wR_factor_ref         0.2084
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2977
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00004c2.cif
_cod_data_source_block           lq-0903-2
_cod_depositor_comments
'Adding full bibliography for 7157334--7157335.cif.'
_cod_original_cell_volume        1768.95(14)
_cod_database_code               7157334
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4A)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C6(H6A,H6B), C1(H1A,H1B), C1A(H1AA,H1AB)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              29159
_olex2_submission_special_instructions 'No special instructions were received'