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_4023473
_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
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.863(4)
_cell_length_b                   25.147(12)
_cell_length_c                   16.643(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3
_cell_measurement_theta_min      21.3
_cell_volume                     3290.6(27)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf Nonius Cad-4'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_sigmaI/netI    0.3280
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5821
_diffrn_reflns_theta_max         64.90
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        .3
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  .77
_exptl_absorpt_correction_T_min  .65
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0022(3)
_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_all   1.000
_refine_ls_goodness_of_fit_obs   1.898
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5415
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.238
_refine_ls_restrained_S_obs      1.833
_refine_ls_R_factor_all          0.2847
_refine_ls_R_factor_obs          0.0725
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2623
_refine_ls_wR_factor_obs         0.1703
_reflns_number_observed          1318
_reflns_number_total             5467
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo8003698-File003.cif
_cod_data_source_block           mm
_cod_depositor_comments
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The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023473