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_1551080
_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'
_chemical_formula_sum            'C40 H46 N2 O4 P2'
_chemical_formula_weight         680.73
_chemical_melting_point          503.15
_chemical_name_common            'Triethyldiphosphonium NDI direduced'
_chemical_name_systematic
;'N,N-dibenzyl-2,6-triethyldiphosphonium-naphthalene-l,4,5,8-tetracarboxylic acid bisimide'
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                90
_cell_angle_beta                 117.061(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1243(13)
_cell_length_b                   12.7829(10)
_cell_length_c                   19.6169(19)
_cell_measurement_reflns_used    9344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.33
_cell_volume                     4047.3(6)
_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 0.999
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            44984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         2.247
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.957
_exptl_transmission_factor_min   0.916
_platon_squeeze_details
;
 ?
;
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 4638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.454(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         10081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+2.9521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                9872
_reflns_number_total             10081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00962k2.cif
_cod_data_source_block           PMSK45_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '230 \%C' was changed to '503.15' -
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               1551080
_shelx_estimated_absorpt_t_min   0.905
_shelx_estimated_absorpt_t_max   0.957
_shelxl_version_number           2014-3
_shelx_res_checksum              80965