Anion–π and anion–π-radical interactions in bis(triphenylphosphonium)-naphthalene diimide salts
Ng, Chee Koon; Tam, Teck Lip Dexter; Wei, Fengxia; Lu, Xuefeng; Wu, Jishan; Organic Chemistry Frontiers 6 (2019) 110–; doi:10.1039/C8QO01122B

data_1554506
_publ_section_title
;
 Anion--\p and anion--\p-radical interactions in
 bis(triphenylphosphonium)-naphthalene diimide salts
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              110
_journal_paper_doi               10.1039/C8QO01122B
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C34 H34 Br Cl3 N O2 P'
_chemical_formula_sum            'C34 H34 Br Cl3 N O2 P'
_chemical_formula_weight         705.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.084(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9670(6)
_cell_length_b                   15.8648(10)
_cell_length_c                   20.3172(11)
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.436
_cell_measurement_theta_min      3.583
_cell_volume                     3413.2(3)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.9.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.9.0'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24969
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.436
_diffrn_reflns_theta_min         3.583
_exptl_absorpt_coefficient_mu    4.484
_exptl_absorpt_correction_T_max  0.573
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6662
_refine_ls_number_restraints     220
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0771P)^2^+13.2757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5263
_reflns_number_total             6662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01122b2.cif
_cod_data_source_block           h398
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554506
_shelx_estimated_absorpt_t_min   0.486
_shelx_estimated_absorpt_t_max   0.573
_shelx_res_checksum              60592