Chemistry of Herz radicals: a new way to near-IR dyes with multiple long-lived and differently-coloured redox states.
Makarov, Alexander Yu; Volkova, Yulia M.; Shundrin, Leonid A.; Dmitriev, Alexey A.; Irtegova, Irina G.; Bagryanskaya, Irina Yu; Shundrina, Inna K.; Gritsan, Nina P.; Beckmann, Jens; Zibarev, Andrey V.; Chemical communications (Cambridge, England) 56 (2020) 727–730; doi:10.1039/c9cc08557b

data_7125804
_publ_section_title
;
 Chemistry of Herz radicals: a new way to near-IR dyes with multiple
 long-lived and differently-coloured redox states.
;
_journal_issue                   5
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              727
_journal_page_last               730
_journal_paper_doi               10.1039/c9cc08557b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C10 H10 N2 S2, C F3 O3 S, C2 H3 N'
_chemical_formula_sum            'C13 H13 F3 N3 O3 S3'
_chemical_formula_weight         412.44
_chemical_name_systematic
'4,10-di-tert-butyl-bis([1,2,3]dithiazolo)[5,4-a:5',4'-h]phenazinediium  bis(trifluoromethanesulfonate), solvate with acetonitrile'
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-13 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                68.737(2)
_cell_angle_beta                 82.028(2)
_cell_angle_gamma                70.790(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7987(4)
_cell_length_b                   11.1508(6)
_cell_length_c                   11.7044(7)
_cell_measurement_reflns_used    7245
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.26
_cell_volume                     895.51(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15499
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.072
_diffrn_reflns_theta_min         2.261
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.3421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3512
_reflns_number_total             4642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08557b2.cif
_cod_data_source_block           1_TfO_m705
_cod_depositor_comments
'Adding full bibliography for 7125802--7125809.cif.'
_cod_database_code               7125804
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.837
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              65217