Ring Opening and Ring Closure in an Indolizine Structure Activated through SNAr Coupling with Superelectrophilic 4,6-Dinitrobenzofuroxan. An Unusual Intramolecular Oxygen Transfer from a N-Oxide Functionality.
Sergey Kurbatov; Vladimir Minkin; Artem Tatarov; Regis Goumont; Francois Terrier; Chemical Communications  (2006) –; doi:10.1039/b608350a

data_7101488
_publ_section_title
;
Ring Opening and Ring Closure in an Indolizine Structure Activated
through SNAr Coupling with Superelectrophilic 4,6-Dinitrobenzofuroxan.
An Unusual Intramolecular Oxygen Transfer from a N-Oxide Functionality.
;
_journal_issue                   41
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b608350a
_journal_year                    2006
_chemical_formula_moiety         'C20 H10 Br N5 O6'
_chemical_formula_sum            'C20 H10 Br N5 O6'
_chemical_formula_weight         496.24
_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                 102.22(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1510(14)
_cell_length_b                   19.421(4)
_cell_length_c                   14.006(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      11
_cell_volume                     1901.1(7)
_computing_cell_refinement       'CAD4 Enraf-Nonius (Enraf-Nonius, 1984)'
_computing_data_collection       'CAD4 Enraf-Nonius (Enraf-Nonius, 1984)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       '\q/5/3\q 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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4561
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_T_max  0.8088
_exptl_absorpt_correction_T_min  0.5562
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al. (1968)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0607P)^2^+0.4250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                2291
_reflns_number_total             4104
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b608350a.txt
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7101488