Doubly-Zwitterionic, Di-reduced, Highly Electron-Rich, Air-Stable Naphthalenediimides: Redox-Switchable Islands of Aromatic-Antiaromatic States
Mukhopadhyay, Pritam; Kumar, sharvan; Shukla, Jyoti; Mandal, Kalyanshis; Kumar, Yogendra; Prakash, Ravi; Ram, Panch; Chemical Science  (2019) –; doi:10.1039/C9SC00962K

data_1551078
_publ_section_title
;
 Doubly-Zwitterionic, Di-reduced, Highly Electron-Rich, Air-Stable
 Naphthalenediimides: Redox-Switchable Islands of Aromatic-Antiaromatic
 States
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00962K
_journal_year                    2019
_chemical_formula_moiety         'C40 H46 N2 O4 P2, 2(B F4)'
_chemical_formula_sum            'C40 H46 B2 F8 N2 O4 P2'
_chemical_formula_weight         854.35
_chemical_melting_point          548.15
_chemical_name_common            'Triethyldiphosphonium NDI dication'
_chemical_name_systematic
"'N,N-dibenzyl-2,6-triethyldiphosphonium-naphthalene-l,4,5,8-tetracarboxylic acid bisimide-bis-tetrafluoroborate' ?"
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-07-05 deposited with the CCDC.    2019-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                94.362(3)
_cell_angle_beta                 91.419(2)
_cell_angle_gamma                116.416(3)
_cell_formula_units_Z            1
_cell_length_a                   9.2333(6)
_cell_length_b                   10.3160(7)
_cell_length_c                   11.4148(8)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.21
_cell_volume                     968.83(12)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1450
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.215
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.988
_exptl_transmission_factor_min   0.969
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4437
_reflns_number_total             4823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00962k2.cif
_cod_data_source_block           PMSK39_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '275 \%C' was changed to '548.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1551078
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
_shelx_res_checksum              774