[4 + 2] Cycloaddition Reaction of C-Aryl Ketenimines with PTAD as a Synthetic Equivalent of Dinitrogen. Synthesis of Triazolocinnolines and Cinnolines
Mateo Alajarin; Baltasar Bonillo; Marta Marin-Luna; Angel Vidal; Raul-Angel Orenes; Journal of Organic Chemistry 74 (2009) 3558–3561; doi:10.1021/jo900304a

data_4024509
_publ_section_title
;
[4 + 2] Cycloaddition Reaction of C-Aryl Ketenimines with PTAD as a
Synthetic Equivalent of Dinitrogen. Synthesis of Triazolocinnolines and
Cinnolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3558
_journal_page_last               3561
_journal_paper_doi               10.1021/jo900304a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C39 H30 N8 O4'
_chemical_formula_weight         674.71
_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                 97.331(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3040(7)
_cell_length_b                   12.8609(6)
_cell_length_c                   16.9243(8)
_cell_measurement_reflns_used    5438
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.32
_cell_volume                     3303.9(3)
_computing_cell_refinement       'Bruker SAINT'
_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_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       \w-scan
_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  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37218
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    'NH free, Me rigid, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         7640
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0748
_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^)+(0.0421P)^2^+2.9624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                6316
_reflns_number_total             7640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900304a_si_002.cif
_cod_data_source_block           vbbf89s
_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               4024509