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_4027571
_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            'C13 H22 N O5 P'
_chemical_formula_weight         303.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.942(12)
_cell_angle_beta                 99.962(11)
_cell_angle_gamma                96.168(11)
_cell_formula_units_Z            2
_cell_length_a                   5.5991(8)
_cell_length_b                   10.8370(15)
_cell_length_c                   13.4812(18)
_cell_measurement_temperature    298(2)
_cell_volume                     768.43(19)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w 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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4594
_diffrn_reflns_theta_full        24.76
_diffrn_reflns_theta_max         24.76
_diffrn_reflns_theta_min         2.87
_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    0.197
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       Block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0752P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                1900
_reflns_number_total             2604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301694n_si_002_3.cif
_cod_data_source_block           compd-20
_cod_original_cell_volume        768.43(18)
_cod_database_code               4027571