Asymmetric Aza-Michael Reactions Catalyzed by Cinchona Alkaloids
Dario Perdicchia; Karl Anker Jørgensen; Journal of Organic Chemistry 72 (2007) 3565–3568; doi:10.1021/jo0626717

data_4022860
_publ_contact_author             'Jorgensen, Karl A.'
_publ_contact_author_email       kaj@chem.au.dk
_publ_section_title
;
 Asymmetric Aza-Michael Reactions Catalyzed by Cinchona Alkaloids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3565
_journal_page_last               3568
_journal_paper_doi               10.1021/jo0626717
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H17 Cl1 N2 O1'
_chemical_formula_sum            'C14 H17 Cl N2 O'
_chemical_formula_weight         264.75
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2006-12-20T11:38:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.146(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1900(5)
_cell_length_b                   7.6990(5)
_cell_length_c                   24.8499(12)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.09
_cell_measurement_theta_min      2.46
_cell_measurement_wavelength     0.71073
_cell_volume                     1375.58(15)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            38048
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         35.86
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing et al., 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 3706 Friedel pairs'
_refine_ls_abs_structure_Flack   0.14(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         9320
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.9421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                7820
_reflns_number_total             9320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0626717rom20070108_054700.cif
_cod_data_source_block           06jo0061_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022860