Cyclization Reactions of 3,4-Diazaheptatrienyl Metal Compounds. Pyridines from an Anionic Analogue of the Fischer Indole Synthesis: Experiment and Theory
Tillmann Kleine; Roland Fröhlich; Birgit Wibbeling; Ernst-Ulrich Würthwein; Journal of Organic Chemistry 76 (2011) 4591–4599; doi:10.1021/jo200487v

data_4026362
_publ_section_title
;
 Cyclization Reactions of 3,4-Diazaheptatrienyl Metal Compounds. Pyridines
 from an Anionic Analogue of the Fischer Indole Synthesis: Experiment and
 Theory
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4591
_journal_page_last               4599
_journal_paper_doi               10.1021/jo200487v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_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                 107.456(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6940(1)
_cell_length_b                   16.2992(1)
_cell_length_c                   8.3872(1)
_cell_measurement_reflns_used    2673
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1655.41(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10952
_diffrn_reflns_theta_full        67.52
_diffrn_reflns_theta_max         67.52
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.9709
_exptl_absorpt_correction_T_min  0.7553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0618P)^2^+0.4233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2380
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200487v_si_001.cif
_cod_data_source_block           wue5319
_cod_database_code               4026362