New Ortho-Directing Group for Lithiation: Use of a Methoxy−Imino Auxiliary for the Synthesis of Chiral Ortho-Substituted Acetyl- and Propionylferrocenes
Ferber, Benoit; Top, Siden; Herson, Patrick; Jaouen, Gérard; Organometallics 26 (2007) 1686–; doi:10.1021/om0609620

data_4072701
_publ_section_title
;
 New Ortho-Directing Group for Lithiation:&#x00A0; Use of a
 Methoxy&#x2212;Imino Auxiliary for the Synthesis of Chiral
 Ortho-Substituted Acetyl- and Propionylferrocenes
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1686
_journal_paper_doi               10.1021/om0609620
_journal_volume                  26
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H11 Fe1 I1 O1'
_chemical_formula_sum            'C12 H11 Fe I O'
_chemical_formula_weight         353.97
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             05-03-07
_audit_creation_method           CRYSTALS_ver_12.24
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8258(4)
_cell_length_b                   8.8461(2)
_cell_length_c                   17.3835(7)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    295
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1203.42(8)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11737
_diffrn_reflns_theta_full        29.999
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.343
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.788
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'DIFABS (Walker & Stuart, 1983)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.25
_refine_diff_density_min         -1.12
_refine_ls_abs_structure_details 'Flack, 1395 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0514
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000686
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 2.77 0.782 2.42 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0536
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0508
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2113
_reflns_number_total             3506
_reflns_threshold_expression     I>3.00u(I)
_oxford_diffrn_Wilson_B_factor   4.12
_oxford_diffrn_Wilson_scale      4.48
_oxford_refine_ls_scale          0.5105(16)
_oxford_structure_analysis_title '3010951 Compound X'
_cod_data_source_file            om0609620si20070212_035701.cif
_cod_data_source_block           CRYSTALS_cif
_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        'C12 H11 Fe1 I1 O1'
_cod_database_code               4072701