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_1554511
_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         'C66 H66 N2 O4 P2, Br1'
_chemical_formula_sum            'C66 H66 Br N2 O4 P2'
_chemical_formula_weight         1095.72
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   24.7543(7)
_cell_length_b                   24.7543(7)
_cell_length_c                   30.0212(9)
_cell_measurement_reflns_used    89076
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.506
_cell_measurement_theta_min      3.595
_cell_volume                     15931.6(8)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APPEXII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            89076
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.506
_diffrn_reflns_theta_min         3.595
_exptl_absorpt_coefficient_mu    1.553
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5168
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.147
_exptl_transmission_factor_max   0.804
_exptl_transmission_factor_min   0.705
_refine_diff_density_max         1.929
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         6700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.005
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.1345
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3998
_refine_ls_wR_factor_ref         0.4175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5690
_reflns_number_total             6700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01122b2.cif
_cod_data_source_block           cu_i180_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        15931.6(10)
_cod_original_sg_symbol_H-M      'R -3'
_cod_original_formula_sum        'C66 H66 Br1 N2 O4 P2'
_cod_database_code               1554511
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.804
_shelx_estimated_absorpt_t_min   0.705
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br2(0.11333) Br1(0.242) Br0A(0.14)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C4(H4A,H4B), C5(H5A,H5B), C3AA(H3AA,H3AB), C5AA(H5AA,H5AB)
3.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30),
  C32(H32)
3.d Idealised Me refined as rotating group:
 C4AA(H4AA,H4AB,H4AC), C6AA(H6AA,H6AB,H6AC)
;
_olex2_submission_special_instructions 'No special instructions were received'