Phosphoryl- and phosphonium-bridged viologens as stable two- and three-electron acceptors for organic electrodes
Bridges, Colin R.; Borys, Andryj M.; Béland, Vanessa A.; Gaffen, Joshua R.; Baumgartner, Thomas; Chemical Science  (2020) –; doi:10.1039/D0SC04183A

data_1559141
_publ_section_title
;
 Phosphoryl- and phosphonium-bridged viologens as stable two- and
 three-electron acceptors for organic electrodes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04183A
_journal_year                    2020
_chemical_formula_moiety         'C19 H20 N2 P, 3(C F3 O3 S), C2 H3 N'
_chemical_formula_sum            'C24 H23 F9 N3 O9 P S3'
_chemical_formula_weight         795.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-07-24 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                102.532(2)
_cell_angle_beta                 90.622(2)
_cell_angle_gamma                97.933(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5784(5)
_cell_length_b                   11.1999(6)
_cell_length_c                   15.6039(8)
_cell_measurement_reflns_used    5924
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      4.057
_cell_measurement_theta_min      0.800
_cell_volume                     1616.98(15)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker D8 Quest Eco'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8700
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.539
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_preparation       'See Experimental details.'
_exptl_crystal_recrystallization_method 'Crystallised from MeCN.'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.788
_refine_diff_density_min         -1.110
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1012P)^2^+8.8467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3677
_reflns_number_total             5924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04183a2.cif
_cod_data_source_block           cb_002_1_01
_cod_database_code               1559141
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C12(H12), C16(H16), C10(H10), C15(H15), C7(H7), C3(H3), C11(H11),
 C4(H4), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
;
_olex2_submission_original_sample_id CB_002
_olex2_submission_special_instructions 'No special instructions were received'