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_4027572
_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            'C11 H15 N O3'
_chemical_formula_weight         209.24
_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                 103.655(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0841(11)
_cell_length_b                   6.8413(9)
_cell_length_c                   20.348(3)
_cell_measurement_reflns_used    1526
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.36
_cell_measurement_theta_min      2.59
_cell_volume                     1093.6(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10021
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_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    0.093
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick(1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       blocks
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0679P)^2^+0.1871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                1415
_reflns_number_total             1921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301694n_si_002_4.cif
_cod_data_source_block           compd-35
_cod_database_code               4027572