2,6-Diacylnaphthalene-1,8:4,5-Bis(dicarboximides): Synthesis, Reduction Potentials, and Core Extension
Lauren E. Polander; Laxman Pandey; Alexander Romanov; Alexandr Fonari; Stephen Barlow; Brian M. Seifried; Tatiana V. Timofeeva; Jean-Luc Brédas; Seth R. Marder; Journal of Organic Chemistry 77 (2012) 5544–5551; doi:10.1021/jo3006232

data_4027264
_publ_section_title
;
 2,6-Diacylnaphthalene-1,8:4,5-Bis(dicarboximides): Synthesis, Reduction
 Potentials, and Core Extension
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5544
_journal_page_last               5551
_journal_paper_doi               10.1021/jo3006232
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C40 H38 N6 O2'
_chemical_formula_sum            'C40 H38 N6 O2'
_chemical_formula_weight         634.76
_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                60.43(2)
_cell_angle_beta                 85.26(2)
_cell_angle_gamma                89.20(2)
_cell_formula_units_Z            1
_cell_length_a                   4.806(6)
_cell_length_b                   14.85(2)
_cell_length_c                   14.93(2)
_cell_measurement_reflns_used    717
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.75
_cell_volume                     923(2)
_computing_cell_refinement       'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX II 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2156
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3546
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_platon_squeeze_details
'                                                               '
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.010(3)
_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   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.2011
_refine_ls_R_factor_gt           0.1000
_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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2218
_reflns_number_gt                1257
_reflns_number_total             3546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3006232_si_004.cif
_cod_data_source_block           b
_cod_database_code               4027264