Reactions of Tetracyanoethylene with N'-Arylbenzamidines: A Route to 2-Phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles
Styliana I. Mirallai; Maria Manoli; Panayiotis A. Koutentis; Journal of Organic Chemistry 78 (2013) 8655–8668; doi:10.1021/jo4013699

data_4028551
_publ_section_title
;
 Reactions of Tetracyanoethylene with N'-Arylbenzamidines: A Route to
 2-Phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8655
_journal_page_last               8668
_journal_paper_doi               10.1021/jo4013699
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C18 H11 N5'
_chemical_formula_sum            'C18 H11 N5'
_chemical_formula_weight         297.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.7212(5)
_cell_length_b                   16.922(2)
_cell_length_c                   25.652(3)
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    100.3(4)
_cell_measurement_theta_max      67.3496
_cell_measurement_theta_min      3.1260
_cell_volume                     2917.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6039
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       rod
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0006(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   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0541
_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^)+(0.1166P)^2^+0.0949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                2161
_reflns_number_total             2584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4013699_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2917.5(5)
_cod_original_sg_symbol_H-M      ' P b c a'
_cod_database_code               4028551