Cobalt(ii)/(imidazoline–oxazoline)-catalyzed enantioselective Michael addition of 2-acetyl azaarenes to β-CF3-β-disubstituted nitroalkenes
Hao, Xin-Qi; Wang, Cong; Liu, Shuang-Liang; Wang, Xiao; Wang, Li; Gong, Jun-Fang; Song, Mao-Ping; Organic Chemistry Frontiers 4 (2017) 308–; doi:10.1039/C6QO00562D

data_1553572
_publ_section_title
;
 Cobalt(ii)/(imidazoline--oxazoline)-catalyzed enantioselective Michael
 addition of 2-acetyl azaarenes to \b-CF3-\b-disubstituted nitroalkenes
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              308
_journal_paper_doi               10.1039/C6QO00562D
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H11 Cl F3 N3 O3'
_chemical_formula_sum            'C15 H11 Cl F3 N3 O3'
_chemical_formula_weight         373.72
_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             2016-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-05 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.74798(19)
_cell_length_b                   9.1129(2)
_cell_length_c                   21.7190(5)
_cell_measurement_reflns_used    3235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9270
_cell_measurement_theta_min      4.0490
_cell_volume                     1533.50(6)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -49.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 86

  2 omega  -52.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   60.0000 87

  3 omega  -43.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 56

  4 omega   57.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 45

  5 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 26

  6 omega  -22.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 66

  7 omega   -1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   90.0000 76

  8 omega   56.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 33

  9 omega   42.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 41

 10 omega   73.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 28

 11 omega   42.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 43

 12 omega   42.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 33

 13 omega   43.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 43

 14 omega   50.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 53

 15 omega   41.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 48

 16 omega   41.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 35

 17 omega   39.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0178999000
_diffrn_orient_matrix_UB_12      -0.1005128000
_diffrn_orient_matrix_UB_13      0.0566338000
_diffrn_orient_matrix_UB_21      -0.0715574000
_diffrn_orient_matrix_UB_22      -0.1296463000
_diffrn_orient_matrix_UB_23      -0.0376121000
_diffrn_orient_matrix_UB_31      0.1848052000
_diffrn_orient_matrix_UB_32      -0.0406138000
_diffrn_orient_matrix_UB_33      -0.0201236000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.052
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         4.071
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91770
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0554P)^2^+0.0371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2590
_reflns_number_total             2741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00562d2.cif
_cod_data_source_block           20160454
_cod_original_cell_volume        1533.51(6)
_cod_database_code               1553572
_chemical_oxdiff_formula         C1H1O1N1Br1
_reflns_odcompleteness_completeness 99.94
_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
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              11265
_shelx_hkl_checksum              57998
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'