Asymmetric Michael additions of α-cyanoacetates by soft Lewis acid/hard Brønsted acid catalysis: stereodivergency with bi- vs. monometallic catalysts
Eitel, Simon H.; Jautze, Sascha; Frey, Wolfgang; Peters, René; Chemical Science 4 (2013) 2218–; doi:10.1039/c3sc50419k

data_1514693
_publ_section_title
;
 Asymmetric Michael additions of \a-cyanoacetates by soft Lewis acid/hard
 Br\/onsted acid catalysis: stereodivergency with bi- vs. monometallic
 catalysts
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              2218
_journal_paper_doi               10.1039/c3sc50419k
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C19 H22 Br N O3, 0.5(C4 H10 O)'
_chemical_formula_sum            'C21 H27 Br N O3.5'
_chemical_formula_weight         429.35
_chemical_name_systematic
;
tert-Butyl-2-(4-bromophenyl)-2-cyano-2-(3-oxocyclohexyl)acetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.921(17)
_cell_angle_beta                 72.269(17)
_cell_angle_gamma                70.983(17)
_cell_formula_units_Z            2
_cell_length_a                   8.953(2)
_cell_length_b                   9.856(2)
_cell_length_c                   14.208(3)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      8
_cell_volume                     1122.3(5)
_computing_cell_refinement       'Siemens P3/PC Data Collection System'
_computing_data_collection       'Siemens P3/PC Data Collection System'
_computing_data_reduction        'SHELXTL-plus, XDISK (Sheldrick, 1991)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nicolet P3'
_diffrn_measurement_method       Wyckoff-Scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4942
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             446
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.063
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0800
_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^)+(0.0409P)^2^+1.4479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                1853
_reflns_number_total             3524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc50419k.txt
_cod_data_source_block           s1680rm2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Psi-Scan' changed to
'psi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1122.2(4)
_cod_original_formula_sum        'C21 H27 Br N O3.50'
_cod_database_code               1514693