An Efficient and Facile Synthesis of Highly Substituted 2,6-Dicyanoanilines
Chenyi Yi; Carmen Blum; Shi-Xia Liu; Gabriela Frei; Antonia Neels; Philippe Renaud; Samuel Leutwyler; Silvio Decurtins; Journal of Organic Chemistry 73 (2008) 3596–3599; doi:10.1021/jo800260b

data_4023396
_publ_section_title
;
 An Efficient and Facile Synthesis of Highly Substituted
 2,6-Dicyanoanilines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3596
_journal_page_last               3599
_journal_paper_doi               10.1021/jo800260b
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C16 H21 N3 Si2'
_chemical_formula_weight         311.54
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.685(11)
_cell_angle_beta                 63.344(11)
_cell_angle_gamma                80.051(13)
_cell_formula_units_Z            2
_cell_length_a                   9.8970(17)
_cell_length_b                   10.0381(15)
_cell_length_c                   11.0211(16)
_cell_measurement_reflns_used    8524
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.16
_cell_volume                     917.5(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12427
_diffrn_reflns_theta_full        29.22
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0531P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                3552
_reflns_number_total             4945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800260b-File001.cif
_cod_data_source_block           y38c-f
_cod_database_code               4023396