Base-stabilized nitrilium ions as convenient imine synthons.
van Dijk, Tom; Bakker, Martijn S.; Holtrop, Flip; Nieger, Martin; Slootweg, J. Chris; Lammertsma, Koop; Organic letters 17 (2015) 1461–1464; doi:10.1021/acs.orglett.5b00339

data_1554834
_publ_section_title
;
 Base-stabilized nitrilium ions as convenient imine synthons.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1461
_journal_page_last               1464
_journal_paper_doi               10.1021/acs.orglett.5b00339
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H26 N2'
_chemical_formula_sum            'C20 H26 N2'
_chemical_formula_weight         294.43
_chemical_name_systematic
;
 (Z)-N-mesityl-N'-phenylpivalimidamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.69(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.693(1)
_cell_length_b                   17.464(2)
_cell_length_c                   11.525(1)
_cell_measurement_reflns_used    180
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_cell_volume                     1700.0(3)
_computing_cell_refinement       EVALCCD
_computing_data_collection       Collect
_computing_data_reduction        EVALCCD
_computing_molecular_graphics    XP
_computing_publication_material  publCif
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in \f and \w, 2\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16156
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       blocks
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.6787P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3226
_reflns_number_total             3869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00339_si_002.cif
_cod_data_source_block           jcs015_compound_12a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554834
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.990