Stereochemistry of Substitution of the α-Dimethylamino Group by Dialkylzinc in Chiral Benzylferrocene
Tatsuki Takahashi; Takashi Konno; Kenichi Ogata; Shin-ichi Fukuzawa; Journal of Organic Chemistry 77 (2012) 6638–6642; doi:10.1021/jo3012013

data_4027356
_publ_section_title
;
 Stereochemistry of Substitution of the \a-Dimethylamino Group by
 Dialkylzinc in Chiral Benzylferrocene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6638
_journal_page_last               6642
_journal_paper_doi               10.1021/jo3012013
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C19 H19 Br2 Fe N'
_chemical_formula_sum            'C19 H19 Br2 Fe N'
_chemical_formula_weight         477.02
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.972(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.4379(9)
_cell_length_b                   12.2540(15)
_cell_length_c                   9.8924(13)
_cell_measurement_reflns_used    3632
_cell_measurement_temperature    183
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.21
_cell_volume                     898.24(19)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      183
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8104
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.298
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_correction_T_min  0.360
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_description       plate
_exptl_crystal_F_000             472.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         3.220
_refine_diff_density_min         -1.670
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1780 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.008(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3892
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[2.8800\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                3321
_reflns_number_total             3892
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo3012013_si_001.cif
_cod_data_source_block           C19H19Br2NFe
_cod_original_cell_volume        898.25(19)
_cod_database_code               4027356