Attempted generation of the potentially aromatic 6,7-diphenyldibenzo[e,g][1,4]diazocine dianion leads with profound rearrangement to the isomeric n-(2-amino-1,2-diphenylethenyl)carbazole dianions.
Eisch, John J.; Manchanayakage, Renuka N.; Rheingold, Arnold L.; Organic letters 11 (2009) 4060–4063; doi:10.1021/ol901503s

data_1504103
_publ_section_title
;
 Attempted generation of the potentially aromatic
 6,7-diphenyldibenzo[e,g][1,4]diazocine dianion leads with profound
 rearrangement to the isomeric n-(2-amino-1,2-diphenylethenyl)carbazole
 dianions.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4060
_journal_page_last               4063
_journal_paper_doi               10.1021/ol901503s
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C26 H20 N2'
_chemical_formula_weight         360.44
_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                92.014(6)
_cell_angle_beta                 98.566(6)
_cell_angle_gamma                99.128(6)
_cell_formula_units_Z            4
_cell_length_a                   7.3565(6)
_cell_length_b                   13.3596(12)
_cell_length_c                   19.9232(18)
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      86.67
_cell_measurement_theta_min      7.88
_cell_volume                     1908.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8646
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         64.22
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00085(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         4803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+1.1624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                3208
_reflns_number_total             5203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901503s_si_002.cif
_cod_data_source_block           eisch5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504103