Enantioselective nickel-catalyzed Michael additions of 2-acetylazaarenes to nitroalkenes.
Simpson, Alain J.; Lam, Hon Wai; Organic letters 15 (2013) 2586–2589; doi:10.1021/ol400578c

data_1512028
_publ_section_title
;
 Enantioselective nickel-catalyzed Michael additions of 2-acetylazaarenes
 to nitroalkenes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2586
_journal_page_last               2589
_journal_paper_doi               10.1021/ol400578c
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H11 Br N2 O3 S, 0.5 C6 H14'
_chemical_formula_sum            'C16 H18 Br N2 O3 S'
_chemical_formula_weight         398.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.61159(10)
_cell_length_b                   11.5643(3)
_cell_length_c                   24.3578(4)
_cell_measurement_reflns_used    6670
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.4165
_cell_measurement_theta_min      3.0594
_cell_volume                     1580.68(6)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1992)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14990
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  0.5508
_exptl_absorpt_correction_T_min  0.3243
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21d (release 25-05-2012 CrysAlis171 .NET)
(compiled May 25 2012,16:20:25)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_platon_squeeze_details
;
One half molecule of disordered hexane per asymmetric unit removed with 
SQUEEZE.
;
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1567 Friedel pairs '
_refine_ls_abs_structure_Flack   -0.014(8)
_refine_ls_extinction_coef       0.0028(6)
_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   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                3469
_reflns_number_total             3952
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol400578c_si_001.cif
_cod_data_source_block           hl2023
_cod_original_cell_volume        1580.67(5)
_cod_database_code               1512028