Enantioselective Conjugate Addition of 2-Acetyl Azaarenes to β,β-Disubstituted Nitroalkene for the Construction of All-Carbon Quaternary Stereocenters.
Ma, Hongli; Xie, Lei; Zhang, Zhenhua; Wu, Lin-Gang; Fu, Bin; Qin, Zhaohai; The Journal of organic chemistry 82 (2017) 7353–7362; doi:10.1021/acs.joc.7b01014

data_4032739
_publ_section_title
;
 Enantioselective Conjugate Addition of 2-Acetyl Azaarenes to
 \b,\b-Disubstituted Nitroalkene for the Construction of All-Carbon
 Quaternary Stereocenters.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7353
_journal_page_last               7362
_journal_paper_doi               10.1021/acs.joc.7b01014
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 Br N2 O5'
_chemical_formula_sum            'C20 H21 Br N2 O5'
_chemical_formula_weight         449.30
_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             2016-01-15
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7863(3)
_cell_length_b                   11.9749(3)
_cell_length_c                   15.8854(4)
_cell_measurement_reflns_used    4609
_cell_measurement_temperature    103.2
_cell_measurement_theta_max      70.5378
_cell_measurement_theta_min      3.6881
_cell_volume                     2051.84(9)
_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      103.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  -82.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  113.0000  -49.0000 92

  2 omega  -50.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   64.0000  -97.0000 60

  3 omega   94.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   58.0000 -115.0000 75

  4 omega   37.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -113.0000   38.0000 51

  5 omega   37.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -113.0000 -130.0000 66

  6 omega  -48.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -120.0000 64

  7 omega  -30.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 46

  8 omega   62.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 50

  9 omega   62.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 31

 10 omega   43.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 37

 11 omega  107.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 66

 12 omega  102.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 25

 13 omega   44.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0138142000
_diffrn_orient_matrix_UB_12      -0.0884401000
_diffrn_orient_matrix_UB_13      0.0698874000
_diffrn_orient_matrix_UB_21      0.1397995000
_diffrn_orient_matrix_UB_22      0.0085451000
_diffrn_orient_matrix_UB_23      0.0189444000
_diffrn_orient_matrix_UB_31      -0.0258369000
_diffrn_orient_matrix_UB_32      0.0930300000
_diffrn_orient_matrix_UB_33      0.0645080000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6758
_diffrn_reflns_theta_full        70.67
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         4.62
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77251
_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_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0520P)^2^+0.1158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                3781
_reflns_number_total             3841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01014_si_001.cif
_cod_data_source_block           exp_3838
_cod_database_code               4032739
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97