Stereoselective aldol reactions using pseudo C<sub>2</sub> symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione.
Inoue, Yuta; Hatayama, Takahiro; Kawasaki-Takasuka, Tomoko; Agou, Tomohiro; Kubota, Toshio; Yamazaki, Takashi; Chemical communications (Cambridge, England) 54 (2018) 9913–9916; doi:10.1039/c8cc05458d

data_7122086
_publ_section_title
;
 Stereoselective aldol reactions using pseudo C<sub>2</sub> symmetric
 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9913
_journal_page_last               9916
_journal_paper_doi               10.1039/c8cc05458d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C18 H22 F3 N O3'
_chemical_formula_sum            'C18 H22 F3 N O3'
_chemical_formula_weight         357.36
_chemical_melting_point          469.8(11)
_chemical_name_systematic
(2S*,3R*,4R*)-N-Benzyl-2-(tert-butyl)-tetrahydro-6-oxo-4-(trifluoromethyl)-2H-pyran-3-carboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.711(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0908(7)
_cell_length_b                   9.2610(6)
_cell_length_c                   16.8687(12)
_cell_measurement_reflns_used    15487
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1726.8(2)
_computing_cell_refinement
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 180
               Slice: -60.0000 - 120.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 50.0000
              2theta: 30.0000
scan:
    Number of images: 180
               Slice: -60.0000 - 120.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 50.0000
              2theta: 30.0000
scan:
    Number of images: 180
               Slice: -60.0000 - 120.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 240.0000
                 XTD: 50.0000
              2theta: 30.0000
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.034031
_diffrn_orient_matrix_UB_12      -0.081761
_diffrn_orient_matrix_UB_13      0.018318
_diffrn_orient_matrix_UB_21      0.017176
_diffrn_orient_matrix_UB_22      -0.016440
_diffrn_orient_matrix_UB_23      -0.105293
_diffrn_orient_matrix_UB_31      0.056026
_diffrn_orient_matrix_UB_32      0.019147
_diffrn_orient_matrix_UB_33      0.006150
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       Prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.296
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0431P)^2^+0.5401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3320
_reflns_number_total             3941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05458d2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '468.7-470.9' was changed to
'469.8(11)' - the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7122084--7122089.cif.

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C18 H22 F3 N O3)'
_cod_original_formula_sum        'C36 H44 F6 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     714.73
_cod_database_code               7122086
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C16(H16), C18(H18), C21(H21), C22(H22), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              64434
_olex2_submission_special_instructions 'No special instructions were received'