Preparation and diastereoselective ortho-metalation of chiral ferrocenyl imidazolines: remarkable influence of LDA as metalation additive.
Peters, René; Fischer, Daniel F.; Organic letters 7 (2005) 4137–4140; doi:10.1021/ol051437k

data_1506665
_publ_section_title
;
 Preparation and diastereoselective ortho-metalation of chiral ferrocenyl
 imidazolines: remarkable influence of LDA as metalation additive.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4137
_journal_page_last               4140
_journal_paper_doi               10.1021/ol051437k
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_compound_source        'Peters group'
_chemical_formula_moiety         'C34 H32 Fe N2 O '
_chemical_formula_sum            'C34 H32 Fe N2 O'
_chemical_formula_weight         540.490
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8803(2)
_cell_length_b                   13.2759(2)
_cell_length_c                   20.8422(4)
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     2733.87(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.06943
_diffrn_orient_matrix_UB_12      0.07364
_diffrn_orient_matrix_UB_13      0.00030
_diffrn_orient_matrix_UB_21      -0.00214
_diffrn_orient_matrix_UB_22      -0.00232
_diffrn_orient_matrix_UB_23      0.07526
_diffrn_orient_matrix_UB_31      0.03488
_diffrn_orient_matrix_UB_32      0.03288
_diffrn_orient_matrix_UB_33      0.00201
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7877
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .38
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.176
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.033(14)
_refine_ls_extinction_coef       0.031(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         7851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0445
_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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                7049
_reflns_number_total             7851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051437ksi20050621_020219.cif
_cod_data_source_block           'global_2'
_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_original_sg_symbol_H-M      'P 21 21 21    '
_cod_original_formula_sum        'C34 H32 Fe N2 O '
_cod_database_code               1506665