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_7125875
_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         'C15 H9 N3 O6, 2(C16 H36 N)'
_chemical_formula_sum            'C47 H81 N5 O6'
_chemical_formula_weight         812.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-09
_audit_creation_method
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-10-09 deposited with the CCDC.	2020-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.406(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0335(7)
_cell_length_b                   19.5712(8)
_cell_length_c                   18.2778(9)
_cell_measurement_reflns_used    5244
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.8880
_cell_measurement_theta_min      3.6930
_cell_volume                     4937.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4419
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     10.00  43.00   1.00   25.00    --    9.66 -99.00 -60.00   33
  2  \w    -73.00  83.00   1.00   25.00    --    9.66   0.00 -30.00  156
;
_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      0.0041677000
_diffrn_orient_matrix_UB_12      0.0241961000
_diffrn_orient_matrix_UB_13      0.0293018000
_diffrn_orient_matrix_UB_21      -0.0495695000
_diffrn_orient_matrix_UB_22      -0.0048676000
_diffrn_orient_matrix_UB_23      0.0019320000
_diffrn_orient_matrix_UB_31      0.0128771000
_diffrn_orient_matrix_UB_32      -0.0265357000
_diffrn_orient_matrix_UB_33      0.0263587000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.584
_diffrn_reflns_theta_min         3.381
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98174
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile/water'
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.412
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         10719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0524P)^2^+2.4414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1431
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7336
_reflns_number_total             10719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08547e2.cif
_cod_data_source_block           ac_cb_newionpair2_mo
_cod_depositor_comments
'Adding full bibliography for 7125875--7125876.cif.'
_cod_database_code               7125875
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C47 H81 N5 O6'
_chemical_oxdiff_usercomment     'long needle'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H46C)=Sof(H46D)=Sof(C47B)=Sof(H47D)=Sof(H47E)=Sof(H47F)=1-FVAR(1)
 Sof(H46A)=Sof(H46B)=Sof(C47A)=Sof(H47A)=Sof(H47B)=Sof(H47C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C16(H16A,H16B), C28(H28A,H28B), C24(H24A,H24B), C42(H42A,
 H42B), C25(H25A,H25B), C36(H36A,H36B), C41(H41A,H41B), C40(H40A,H40B),
 C30(H30A,H30B), C21(H21A,H21B), C37(H37A,H37B), C32(H32A,H32B), C44(H44A,H44B),
  C17(H17A,H17B), C26(H26A,H26B), C38(H38A,H38B), C22(H22A,H22B), C29(H29A,
 H29B), C18(H18A,H18B), C45(H45A,H45B), C33(H33A,H33B), C34(H34A,H34B),
 C46(H46A,H46B), C46(H46C,H46D)
3.b Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C27(H27A,H27B,H27C), C39(H39A,H39B,H39C), C7(H7A,H7B,
 H7C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C15(H15A,H15B,H15C), C31(H31A,
 H31B,H31C), C35(H35A,H35B,H35C), C11(H11A,H11B,H11C), C47A(H47A,H47B,H47C),
 C47B(H47D,H47E,H47F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2019-07-08
_olex2_exptl_crystal_mounting_method 'oil on a plastic loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.057
_oxdiff_exptl_absorpt_empirical_full_min 0.944