An efficient approach for the construction of trifluoromethylated all-carbon quaternary stereocenters: enantioselective Ni(ii)-catalyzed Michael addition of 2-acetyl azaarene to β,β-disubstituted nitroalkenes.
Hou, Xuhe; Ma, Hongli; Zhang, Zhenhua; Xie, Lei; Qin, Zhaohai; Fu, Bin; Chemical communications (Cambridge, England) 52 (2016) 1470–1473; doi:10.1039/c5cc08480f

data_7118448
_publ_section_title
;
 An efficient approach for the construction of trifluoromethylated
 all-carbon quaternary stereocenters: enantioselective Ni(ii)-catalyzed
 Michael addition of 2-acetyl azaarene to \b,\b-disubstituted
 nitroalkenes.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1470
_journal_page_last               1473
_journal_paper_doi               10.1039/c5cc08480f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H10 Cl F3 N2 O3 S'
_chemical_formula_sum            'C14 H10 Cl F3 N2 O3 S'
_chemical_formula_weight         378.75
_chemical_melting_point          385.0(10)
_chemical_name_systematic
(R)-3-(4-chlorophenyl)-4,4,4-trifluoro-3-(nitromethyl)-1-(thiazol-2-yl)butan-1-one
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-24
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2015-02-26 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2939(5)
_cell_length_b                   10.7278(3)
_cell_length_c                   14.0751(7)
_cell_measurement_reflns_used    4268
_cell_measurement_temperature    103.3
_cell_measurement_theta_max      70.6890
_cell_measurement_theta_min      4.2936
_cell_volume                     1554.33(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      103.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -31.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  -45.0000  150.0000 37

  2 omega  -31.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -77.0000   60.0000 50

  3 omega  -11.00   48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -92.0000  -68.0000 59

  4 omega   19.00  100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   77.0000 -180.0000 81

  5 omega   26.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000  -30.0000 64

  6 omega   43.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 33

  7 omega  102.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 25

  8 omega   72.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 26

  9 omega   46.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 44

 10 omega   97.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 73

 11 omega   57.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 68

 12 omega  112.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 47

 13 omega  146.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 26

 14 omega   37.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 104

 15 omega   -1.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8220  -92.0000  111.0000 61

 16 omega   21.00   48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8220  -77.0000 -120.0000 27

 17 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -31.0000 -101.0000 26

 18 omega   87.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 36

 19 omega  149.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 20 omega   98.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0354981000
_diffrn_orient_matrix_UB_12      -0.1290457000
_diffrn_orient_matrix_UB_13      -0.0404210000
_diffrn_orient_matrix_UB_21      0.1452297000
_diffrn_orient_matrix_UB_22      -0.0281777000
_diffrn_orient_matrix_UB_23      -0.0161229000
_diffrn_orient_matrix_UB_31      0.0089275000
_diffrn_orient_matrix_UB_32      -0.0563222000
_diffrn_orient_matrix_UB_33      0.1003011000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6648
_diffrn_reflns_theta_full        70.88
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_min         5.18
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether/dichloromethane'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(12)
_refine_ls_extinction_coef       0.0100(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.3242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                2903
_reflns_number_total             2943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc08480f2.cif
_cod_data_source_block           exp_2475
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '384-386' was changed to '385.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7118448
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97