Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization in Electron-Poor 4-Aryl-2-azabuta-1,3-dienes: Indole Synthesis from 2H-Azirines and Diazo Compounds.
Novikov, Mikhail S.; Khlebnikov, Alexander F.; Rostovskii, Nikolai V.; Tcyrulnikov, Sergei; Suhanova, Anna A.; Zavyalov, Kirill V.; Yufit, Dmitry S.; The Journal of organic chemistry 80 (2014) 18–; doi:10.1021/jo501051n

data_4030324
_publ_section_title
;
 Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization
 in Electron-Poor 4-Aryl-2-azabuta-1,3-dienes: Indole Synthesis from
 2H-Azirines and Diazo Compounds.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              18
_journal_paper_doi               10.1021/jo501051n
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C26 H20 N2 O3'
_chemical_formula_weight         408.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 99.250(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5026(4)
_cell_length_b                   13.2431(3)
_cell_length_c                   12.5514(4)
_cell_measurement_reflns_used    4839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8414
_cell_measurement_theta_min      2.9381
_cell_volume                     2051.15(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10036
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0352P)^2^+0.2001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                3799
_reflns_number_total             4623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501051n_si_003.cif
_cod_data_source_block           tsa1
_cod_depositor_comments
'Adding full bibliography for 4030324--4030325.cif.'
_cod_original_cell_volume        2051.14(10)
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4030324