Synthesis and Reactivity of a Novel Class of Long-Lived Ammonium Ylides: Derivatives of Benzo[b]pyrrolo[2,1-f][1.6]naphthyridine
Leonid G. Voskressensky; Ilya V. Vorobiev; Tatyana N. Borisova; Alexey V. Varlamov; Journal of Organic Chemistry 73 (2008) 4596–4601; doi:10.1021/jo8003698

data_4023475
_publ_section_title
;
 Synthesis and Reactivity of a Novel Class of Long-Lived Ammonium
 Ylides: Derivatives of Benzo[b]pyrrolo[2,1-f][1.6]naphthyridine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4596
_journal_page_last               4601
_journal_paper_doi               10.1021/jo8003698
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C19 H15 N3 O3'
_chemical_formula_weight         333.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.843(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.2699(10)
_cell_length_b                   10.1474(10)
_cell_length_c                   18.2789(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.2
_cell_measurement_theta_min      15.3
_cell_volume                     3099.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Enraf Nonius Cad-4'
_diffrn_measurement_method       /w
_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  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6578
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.22
_diffrn_standards_decay_%        0.9
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9539
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0578
_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^)+(0.1390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                4334
_reflns_number_total             6016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8003698-File007.cif
_cod_data_source_block           npos
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023475