Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons
S. Ito; Y. Tokimaru; K. Nozaki; Chem.Commun. 51 (2015) 221–; doi:10.1039/C4cc06643J

data_7116147
_publ_section_title
;
 Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in
 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic
 hydrocarbons
;
_journal_name_full               Chem.Commun.
_journal_page_first              221
_journal_paper_doi               10.1039/C4cc06643J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C38 H29 N'
_chemical_formula_sum            'C38 H29 N'
_chemical_formula_weight         499.62
_chemical_name_systematic
8-t-Butyl-1,2-diphenylbenzo[7,8]indolizino[6,5,4,3-def]phenanthridine
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.784(2)
_cell_length_b                   20.520(5)
_cell_length_c                   29.114(7)
_cell_measurement_reflns_used    12512
_cell_measurement_temperature    93
_cell_measurement_theta_max      31.4
_cell_measurement_theta_min      2.7
_cell_volume                     5248(2)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32588
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+3.2311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                3997
_reflns_number_total             4631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06643j3.cif
_cod_data_source_block           9APPHA
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7116147