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_7115966
_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_sum            'C17 H17 Fe N'
_chemical_formula_weight         291.16
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.970(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0146(3)
_cell_length_b                   23.0686(8)
_cell_length_c                   9.9522(3)
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.8981
_cell_measurement_theta_min      3.3507
_cell_volume                     1370.65(9)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8058
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.962
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82602
_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    1.411
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.023(11)
_refine_ls_extinction_coef       0.0204(12)
_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   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0719
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_full    0.640
_reflns_Friedel_fraction_max     0.490
_reflns_number_gt                4499
_reflns_number_total             4966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07196d2.cif
_cod_data_source_block           shelxl_a
_cod_database_code               7115966
_shelx_estimated_absorpt_t_min   0.665
_shelx_estimated_absorpt_t_max   0.737
_shelxl_version_number           2013-4
_shelx_res_checksum              14367