Direct enantiospecific substitution of primary alpha-aminoalkylferrocenes via Lewis acid-catalyzed C-N bond cleavage
Meng-Guang Zhou; Wen-Zhao Zhang; Shi-Kai Tian; Chem.Commun. 50 (2014) 14531–; doi:10.1039/C4cc07196D

data_7115968
_publ_section_title
;
 Direct enantiospecific substitution of primary alpha-aminoalkylferrocenes
 via Lewis acid-catalyzed C-N bond cleavage
;
_journal_name_full               Chem.Commun.
_journal_page_first              14531
_journal_paper_doi               10.1039/C4cc07196D
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H25 Fe N'
_chemical_formula_sum            'C25 H25 Fe N'
_chemical_formula_weight         395.31
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_audit_creation_date             2014-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0693(3)
_cell_length_b                   17.2089(11)
_cell_length_c                   19.2688(9)
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.0027
_cell_measurement_theta_min      3.3788
_cell_volume                     2012.55(19)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9551
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7935
_exptl_absorpt_correction_T_min  0.7267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(16)
_refine_ls_extinction_coef       0.0148(9)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0394P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                3242
_reflns_number_total             4126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07196d2.cif
_cod_data_source_block           shelxl_c
_cod_database_code               7115968
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H17(0.072) H14(0.077) H13(0.073) H11(0.064) H16(0.071) H20(0.101)
 H19(0.086) H24A(0.116) H24B(0.116) H24C(0.116) H5(0.072) H23(0.086) H25A(0.13)
 H25B(0.13) H25C(0.13) H4(0.088) H21(0.108) H22(0.103) H2(0.086) H3(0.096)
 H7(0.126) H6(0.133) H8(0.119) H9(0.131) H10(0.13)
 Fixed X: H17(0.3286) H14(0.9002) H13(0.8675) H11(0.7367) H16(0.3465) H20(-
 0.0139) H19(0.2029) H24A(0.4577) H24B(0.5159) H24C(0.3378) H5(0.1768)
 H23(0.6564) H25A(0.8107) H25B(0.8207) H25C(0.9592) H4(0.1616) H21(0.1016)
 H22(0.4326) H2(0.7694) H3(0.5285) H7(0.927) H6(0.8146) H8(0.6139) H9(0.3022)
 H10(0.4267)
 Fixed Y: H17(0.248) H14(0.0943) H13(0.1269) H11(0.2152) H16(0.2105)
 H20(0.0672) H19(0.1418) H24A(0.204) H24B(0.1316) H24C(0.1246) H5(0.2945)
 H23(0.1609) H25A(0.0292) H25B(0.08) H25C(0.1037) H4(0.4389) H21(0.0423)
 H22(0.0871) H2(0.3664) H3(0.4835) H7(0.4229) H6(0.2907) H8(0.512) H9(0.4333)
 H10(0.2947)
 Fixed Z: H17(0.857) H14(0.9297) H13(0.815) H11(0.7286) H16(0.9709)
 H20(0.6952) H19(0.7681) H24A(1.0818) H24B(1.1277) H24C(1.0691) H5(0.7041)
 H23(0.6189) H25A(1.0405) H25B(1.108) H25C(1.0427) H4(0.7184) H21(0.5838)
 H22(0.5462) H2(0.775) H3(0.7608) H7(0.6168) H6(0.5866) H8(0.5947) H9(0.5511)
 H10(0.5463)
;