Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio.
Rasappan, Ramesh; Hager, Markus; Gissibl, Anja; Reiser, Oliver; Organic letters 8 (2006) 6099–6102; doi:10.1021/ol062697k

data_1506322
_publ_section_title
;
 Highly enantioselective michael additions of indole to benzylidene
 malonate using simple bis(oxazoline) ligands: importance of metal/ligand
 ratio.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              6099
_journal_page_last               6102
_journal_paper_doi               10.1021/ol062697k
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C22 H30 Cl2 Cu N6 O2'
_chemical_formula_sum            'C22 H30 Cl2 Cu N6 O2'
_chemical_formula_weight         544.97
_chemical_name_systematic        ' ?'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8623(7)
_cell_length_b                   10.1661(8)
_cell_length_c                   24.4608(17)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.17
_cell_volume                     2452.5(3)
_computing_cell_refinement       'STOE (1998)'
_computing_data_collection       'STOE (1998)'
_computing_data_reduction        'STOE (1998)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1993)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE-IPDS diffractometer'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17724
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full        25.90
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.140
_exptl_absorpt_correction_T_max  0.8680
_exptl_absorpt_correction_T_min  0.7811
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'numerical from crystal shape (X-SHAPE, X-RED. STOE, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0553P)^2^]         where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                4241
_reflns_number_total             4742
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol062697ksi20061105_102357.cif
_cod_data_source_block           d286
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1506322