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_1554835
_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         'C14 H22 N2'
_chemical_formula_sum            'C14 H22 N2'
_chemical_formula_weight         218.33
_chemical_name_systematic
;
 (Z)-N'-mesitylpivalimidamide
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   26.3163(12)
_cell_length_b                   26.3163(12)
_cell_length_c                   10.4030(5)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.0
_cell_volume                     6239.3(5)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    Shelxtl-Plus
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture with PHOTON 100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 1\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            98819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.681
_diffrn_source                   'Incoatec High Brilliance Microfocus Source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_description       plates
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1416 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0693P)^2^+14.2570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2977
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00339_si_002.cif
_cod_data_source_block           jcs035_compound_13a
_cod_original_cell_volume        6239.3(6)
_cod_database_code               1554835
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.989