Phenanthrene-Fused Azo-ene-ynes: Synthesis of Dibenzo[f,h]cinnoline and Dibenzo[e,g]isoindazole Derivatives
Brian S. Young; Felix Köhler; Rainer Herges; Michael M. Haley; Journal of Organic Chemistry 76 (2011) 8483–8487; doi:10.1021/jo201378t

data_4026644
_publ_section_title
;
 Phenanthrene-Fused Azo-ene-ynes: Synthesis of Dibenzo[f,h]cinnoline and
 Dibenzo[e,g]isoindazole Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8483
_journal_page_last               8487
_journal_paper_doi               10.1021/jo201378t
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C40 H38 N6'
_chemical_formula_weight         602.76
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5579(19)
_cell_length_b                   14.880(3)
_cell_length_c                   23.185(5)
_cell_measurement_reflns_used    2758
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.68
_cell_volume                     3297.4(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14088
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0480P)^2^+0.5979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2762
_reflns_number_total             3587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201378t_si_002.cif
_cod_data_source_block           mh40
_cod_database_code               4026644