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_4023472
_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_moiety         'C20 H15 N3 O4'
_chemical_formula_sum            'C20 H15 N3 O4'
_chemical_formula_weight         361.35
_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                   12.3267(9)
_cell_length_b                   7.3356(6)
_cell_length_c                   36.777(3)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.32
_cell_measurement_theta_min      2.21
_cell_volume                     3325.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            24367
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0878
_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^)+(0.0500P)^2^+15.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1827
_reflns_number_gt                2503
_reflns_number_total             2915
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo8003698-File002.cif
_cod_data_source_block           UDN-5
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023472