Direct Synthesis of NNN-Donor Enantiopure Scorpionate Ligands by an Efficient Diastereoselective Nucleophilic Addition to Imines
Antonio Otero; Juan Fernández-Baeza; Juan Tejeda; Agustín Lara-Sánchez; Sonia Franco; Jaime Martínez-Ferrer; María P. Carrión; I. López-Solera; Ana M. Rodríguez; Luis F. Sánchez-Barba; Inorganic Chemistry 50 (2011) 1826–1839; doi:10.1021/ic102242x

data_4324519
_publ_section_title
;
 Direct Synthesis of NNN-Donor Enantiopure Scorpionate Ligands by an
 Efficient Diastereoselective Nucleophilic Addition to Imines
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1826
_journal_page_last               1839
_journal_paper_doi               10.1021/ic102242x
_journal_volume                  50
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C16 H18 F N'
_chemical_formula_weight         243.31
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.577(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.707(4)
_cell_length_b                   6.833(2)
_cell_length_c                   18.393(6)
_cell_measurement_temperature    180(2)
_cell_volume                     1330.6(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3048
_diffrn_reflns_theta_full        22.19
_diffrn_reflns_theta_max         22.19
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.294018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       Plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.651
_exptl_crystal_size_mid          0.432
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.007(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   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                1323
_reflns_number_total             1639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic102242x_si_002_2.cif
_cod_data_source_block           5
_cod_original_cell_volume        1330.5(8)
_cod_database_code               4324519