Extraordinary stability of naphthalenediimide radical ion and its ultra-electron-deficient precursor: strategic role of the phosphonium group.
Kumar, Sharvan; Ajayakumar, M. R.; Hundal, Geeta; Mukhopadhyay, Pritam; Journal of the American Chemical Society 136 (2014) 12004–12010; doi:10.1021/ja504903j

data_4122398
_publ_section_title
;
 Extraordinary stability of naphthalenediimide radical ion and its
 ultra-electron-deficient precursor: strategic role of the phosphonium
 group.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12004
_journal_page_last               12010
_journal_paper_doi               10.1021/ja504903j
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C62 H58 N2 O4 P2, 2(B F4)'
_chemical_formula_sum            'C62 H58 B2 F8 N2 O4 P2'
_chemical_formula_weight         1130.66
_chemical_name_common
'Bis-phosphonium Naphthalenediimide bis-tetrafluoroborate'
_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                105.577(5)
_cell_angle_beta                 101.089(3)
_cell_angle_gamma                110.247(5)
_cell_formula_units_Z            1
_cell_length_a                   11.263(3)
_cell_length_b                   12.130(4)
_cell_length_c                   12.624(5)
_cell_measurement_reflns_used    3067
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.80
_cell_volume                     1479.0(9)
_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    'SIR-92(Altomare et. al.,1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18900
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_platon_squeeze_details
;
The recovered number of electrons match well with one toluene 
molecule at the centre of symmetry, giving Solvent accessible
 voids of 207 A3. 
;
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0709P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                3626
_reflns_number_total             5443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja504903j_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4122397--4122398.cif.'
_cod_database_code               4122398