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_1506323
_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         'C50 H69 Cu2 N15 O5, 3(C2 H3 N), 4(Cl O4)'
_chemical_formula_sum            'C56 H78 Cl4 Cu2 N18 O21'
_chemical_formula_weight         1608.27
_chemical_name_systematic        ' ?'
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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
_cell_angle_alpha                77.309(16)
_cell_angle_beta                 81.440(16)
_cell_angle_gamma                74.732(17)
_cell_formula_units_Z            1
_cell_length_a                   12.0986(18)
_cell_length_b                   12.7138(18)
_cell_length_c                   13.3209(17)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.08
_cell_volume                     1919.4(5)
_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, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1993)'
_diffrn_ambient_temperature      123(1)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_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  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24568
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full        25.84
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.9167
_exptl_absorpt_correction_T_min  0.7914
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'analytical from crystal shape (X-SHAPE, X-RED. STOE, 1996)'
_exptl_crystal_colour            blue-green
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             834
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.800
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         13773
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0748
_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^)+(0.1409P)^2^]         where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2104
_reflns_number_gt                10301
_reflns_number_total             13773
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol062697ksi20061105_102535.cif
_cod_data_source_block           e053
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
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_cod_database_code               1506323