Asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis.
Han, Bo; Xiao, You-Cai; He, Zhao-Quan; Chen, Ying-Chun; Organic letters 11 (2009) 4660–4663; doi:10.1021/ol901939b

data_1504210
_publ_section_title
;
 Asymmetric Michael addition of gamma,gamma-disubstituted
 alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4660
_journal_page_last               4663
_journal_paper_doi               10.1021/ol901939b
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H22 Cl N O3'
_chemical_formula_weight         395.87
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.290(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.185(3)
_cell_length_b                   8.740(3)
_cell_length_c                   12.189(4)
_cell_measurement_reflns_used    3287
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.18
_cell_volume                     1003.9(6)
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0878
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7743
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_correction_T_min  0.9193
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.17(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                3146
_reflns_number_total             4500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901939b_si_002.cif
_cod_data_source_block           6e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1003.9(5)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1504210