Reactions of Large Tetraaza-N,N'-dihydroacenes: Formation of Unexpected Adducts and an Unstable Tetraazahexacene
Jens U. Engelhart; Benjamin D. Lindner; Olena Tverskoy; Manuel Schaffroth; Frank Rominger; Uwe H. F. Bunz; Journal of Organic Chemistry 78 (2013) 1249–1253; doi:10.1021/jo3024544

data_4027907
_publ_contact_author_address
;
        Organisch-Chemisches Institut
        Ruprecht-Karls-Universit\"at Heidelberg
        Im Neuenheimer Feld 270
        D-69120 Heidelberg
        Germany
;
_publ_contact_author_email       uwe.bunz@oci.uni-heidelberg.de
_publ_contact_author_fax         '049 6221 54- 8404'
_publ_contact_author_name        'Bunz, Uwe H. F.'
_publ_contact_author_phone       '049 6221 54- 8401'
_publ_section_title
;
 Reactions of Large Tetraaza-N,N'-dihydroacenes: Formation of Unexpected
 Adducts and an Unstable Tetraazahexacene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1249
_journal_page_last               1253
_journal_paper_doi               10.1021/jo3024544
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C44 H50 Cl2 N4 O4 Si2'
_chemical_formula_weight         825.96
_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                102.149(1)
_cell_angle_beta                 114.803(1)
_cell_angle_gamma                108.584(1)
_cell_formula_units_Z            2
_cell_length_a                   13.7684(2)
_cell_length_b                   13.7850(2)
_cell_length_c                   14.3419(2)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      35.37
_cell_measurement_theta_min      2.70
_cell_volume                     2146.61(7)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II Quazar'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'ImuS microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47514
_diffrn_reflns_theta_full        30.65
_diffrn_reflns_theta_max         30.65
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         13217
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.7861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                9654
_reflns_number_total             13217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3024544_si_001_1.cif
_cod_data_source_block           bu11
_cod_original_cell_volume        2146.61(5)
_cod_database_code               4027907