Vinyl Azides Derived from Allenes: Thermolysis Leading to Multisubstituted 1,4-Pyrazines and Mn(III)-Catalyzed Photochemical Reaction Leading to Pyrroles
K. V. Sajna; K. C. Kumara Swamy; Journal of Organic Chemistry 77 (2012) 8712–8722; doi:10.1021/jo301694n

data_4027569
_publ_section_title
;
 Vinyl Azides Derived from Allenes: Thermolysis Leading to
 Multisubstituted 1,4-Pyrazines and Mn(III)-Catalyzed Photochemical
 Reaction Leading to Pyrroles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8712
_journal_page_last               8722
_journal_paper_doi               10.1021/jo301694n
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C18 H30 N2 O6 P2'
_chemical_formula_weight         432.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 103.146(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.587(2)
_cell_length_b                   6.0979(8)
_cell_length_c                   11.5256(15)
_cell_measurement_reflns_used    3749
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.68
_cell_volume                     1066.8(2)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9767
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick(1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       blocks
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.4019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                1684
_reflns_number_total             1886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301694n_si_002_1.cif
_cod_data_source_block           compd-14
_cod_database_code               4027569