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_7125807
_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         'C20 H20 N4 S5 [+ solvent]'
_chemical_formula_sum            'C20 H20 N4 S5'
_chemical_formula_weight         476.70
_chemical_name_systematic
'4,7-di-tert-butylbis[1,2,3]dithiazolo[4'5':3,4;5',4':8,9]dibenzo [c,e][1?4?2,2,7]thiadiazepine'
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-10-17 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.008(5)
_cell_length_b                   7.0295(14)
_cell_length_c                   14.980(3)
_cell_measurement_reflns_used    3089
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      2.73
_cell_volume                     2364.1(11)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0959
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23626
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.729
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.020
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_refine_diff_density_max         0.312
_refine_diff_density_min         -0.345
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.8543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1878
_reflns_number_total             2941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08557b2.cif
_cod_data_source_block           2_m675
_cod_depositor_comments
'Adding full bibliography for 7125802--7125809.cif.'
_cod_original_cell_volume        2364.1(10)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7125807
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.660
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              1205
_shelx_fab_checksum              99011