Synergic asymmetric organocatalysis (SAOc) of Cinchona alkaloids and secondary amines in the synthesis of bicyclo[2.2.2]octan-2-ones.
Bella, Marco; Schietroma, Daniele M Scarpino; Cusella, Pier Paolo; Gasperi, Tecla; Visca, Valerio; Chemical communications (Cambridge, England) 34 (2009) 597–599; doi:10.1039/b816550e

data_7104159
_publ_section_title
;
 Synergic asymmetric organocatalysis (SAOc) of Cinchona alkaloids and
 secondary amines in the synthesis of bicyclo[2.2.2]octan-2-ones.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              597
_journal_page_last               599
_journal_paper_doi               10.1039/b816550e
_journal_volume                  34
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H15 Cl1 O2'
_chemical_formula_sum            'C14 H15 Cl O2'
_chemical_formula_weight         250.71
_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             2008-09-02T09:30:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.292(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5376(3)
_cell_length_b                   6.4529(3)
_cell_length_c                   14.5419(5)
_cell_measurement_reflns_used    5117
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      3.14
_cell_measurement_wavelength     0.71073
_cell_volume                     608.51(4)
_computing_cell_refinement       'Saint+ v7.53A(Bruker-Nonius, 2007)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2007)'
_computing_data_reduction        'Saint+ v7.53A(Bruker-Nonius, 2007)'
_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(2)
_diffrn_detector_area_resol_mean 12.00
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method
;
Narrow slices collected using \f- 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  0.0278
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8211
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.82
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.3
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.1395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                2110
_reflns_number_total             2223
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            b816550e.txt
_cod_data_source_block           08jo0024_0m
_cod_original_formula_sum        'C14 H15 Cl1 O2'
_cod_database_code               7104159