Desymmetrized hexasubstituted [3]radialene anions as aqueous organic catholytes for redox flow batteries.
Turner, Nicholas A.; Freeman, Matthew B.; Pratt, Harry D.; Crockett, Austin E.; Jones, Daniel S.; Anstey, Mitchell R.; Anderson, Travis M.; Bejger, Christopher M.; Chemical communications (Cambridge, England) 56 (2020) 2739–2742; doi:10.1039/c9cc08547e

data_7125876
_publ_section_title
;
 Desymmetrized hexasubstituted [3]radialene anions as aqueous organic
 catholytes for redox flow batteries.
;
_journal_issue                   18
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2739
_journal_page_last               2742
_journal_paper_doi               10.1039/c9cc08547e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H6 N4 O4, 2(C16 H36 N)'
_chemical_formula_sum            'C46 H78 N6 O4'
_chemical_formula_weight         779.14
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-17T16:14:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-10-21 deposited with the CCDC.	2020-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.145(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7559(3)
_cell_length_b                   12.4952(2)
_cell_length_c                   38.3843(8)
_cell_measurement_reflns_used    11281
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.292
_cell_measurement_theta_min      4.007
_cell_measurement_wavelength     1.54184
_cell_volume                     9461.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
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_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
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_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4419
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0248544
_diffrn_orient_matrix_UB_12      -0.082226
_diffrn_orient_matrix_UB_13      0.0263267
_diffrn_orient_matrix_UB_21      0.0319393
_diffrn_orient_matrix_UB_22      0.0670745
_diffrn_orient_matrix_UB_23      0.030295
_diffrn_orient_matrix_UB_31      -0.066848
_diffrn_orient_matrix_UB_32      0.0626625
_diffrn_orient_matrix_UB_33      0.0021046
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_unetI/netI     0.076
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            54925
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        66.875
_diffrn_reflns_theta_max         66.875
_diffrn_reflns_theta_min         3.721
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
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_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.213
_refine_diff_density_max         1.398
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     1040
_refine_ls_number_reflns         15901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0942
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1596P)^2^+10.0449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2573
_refine_ls_wR_factor_ref         0.2878
_reflns_Friedel_coverage         0
_reflns_number_gt                11699
_reflns_number_total             15901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08547e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7125875--7125876.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7125876
_shelx_estimated_absorpt_t_min   0.781
_shelx_estimated_absorpt_t_max   0.893