Novel helix-shape bis[1,2,4]triazolo[4,3-b:3′,4′-f][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties
Korotina, Anna V.; Tolshchina, Svetlana G.; Gazizov, Denis A.; Steparuk, Alexander S.; Kim, Grigory A.; Demina, Nadezhda S.; Ganebnykh, Ilya N.; Slepukhin, Pavel A.; Aleksandrov, Alexey E.; Tameev, Alexey R.; Rusinov, Gennady L.; New Journal of Chemistry 48 (2024) 1983–1991; doi:10.1039/D3NJ05306G

data_7062931
_publ_section_title
;
 Novel helix-shape
 bis[1,2,4]triazolo[4,3-b:3&#x2032;,4&#x2032;-f][1,2,4,5]tetrazines:
 synthesis, optical and charge-transfer properties
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1983
_journal_page_last               1991
_journal_paper_doi               10.1039/D3NJ05306G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H18 N8 O4, C6 H6 O2, 1(C3 H3)'
_chemical_formula_sum            'C29 H27 N8 O6'
_chemical_formula_weight         583.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-17 deposited with the CCDC.	2023-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.45(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.290(3)
_cell_length_b                   7.870(3)
_cell_length_c                   25.420(9)
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.71
_cell_volume                     2811.4(16)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17062
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         2.713
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.19410
_exptl_absorpt_correction_T_min  0.86097
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5705
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.1729
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0050P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1913
_reflns_number_total             5705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05306g2.cif
_cod_data_source_block           dc
_cod_depositor_comments
'Adding full bibliography for 7062930--7062931.cif.'
_cod_original_cell_volume        2811.2(17)
_cod_database_code               7062931
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C24
 1.43 with sigma of 0.02
 C7S-C7S_$1
 1.43 with sigma of 0.02
 C8S-C8S_$1
 1.43 with sigma of 0.02
 C22-C21
 1.43 with sigma of 0.02
 C9S-C7S
 1.43 with sigma of 0.02
 C9S-C8S
 1.43 with sigma of 0.02
 C22-C23
 1.43 with sigma of 0.02
 C7S-C9S
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq, Uanis(C7S) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C9S)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C8S) \\sim Ueq, Uanis(C24) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C7S(0.6) H7S(0.6) C8S(0.6) H8S(0.6) C9S(0.6) H9S(0.6) C21(0.2)
 H21(0.2) C22(0.4) H22(0.4) C24(0.2) H24(0.2) C23(0.4) H23(0.4)
5.a Riding coordinates:
 O4(H5), O5(H6)
5.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
5.c Aromatic/amide H refined with riding coordinates:
 C2S(H2S), C4S(H4S), C5S(H5S), C6S(H6S), C8(H8), C9(H9), C10(H10), C14(H14),
 C15(H15), C16(H16), C7S(H7S), C8S(H8S), C9S(H9S), C21(H21), C22(H22), C24(H24),
  C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'