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_4122397
_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, C24 H20 B'
_chemical_formula_sum            'C86 H78 B N2 O4 P2'
_chemical_formula_weight         1276.25
_chemical_name_common
'Bis-phosphonium-Naphthalenediimide Mono-tetraphenylborate radical cation'
_chemical_name_systematic
;       
? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 127.454(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.158(3)
_cell_length_b                   15.8070(17)
_cell_length_c                   20.093(2)
_cell_measurement_reflns_used    3560
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.49
_cell_volume                     7351.7(13)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25987
_diffrn_reflns_theta_full        25.78
_diffrn_reflns_theta_max         25.78
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9234
_exptl_absorpt_correction_T_min  0.7453
_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    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2700
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
The electron recovered 52 match well with a toluene molecules 
present at two fold axes.
;
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0768P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                4480
_reflns_number_total             6977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja504903j_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4122397--4122398.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4122397