Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring.
Vaddypally, Shivaiah; Kiselev, Vitaly G.; Byrne, Alex N.; Goldsmith, C. Franklin; Zdilla, Michael J.; Chemical science 12 (2020) 2268–2275; doi:10.1039/d0sc04949b

data_1559754
_publ_section_title
;
 Transition-metal-mediated reduction and reversible double-cyclization of
 cyanuric triazide to an asymmetric bitetrazolate involving cleavage of
 the six-membered aromatic ring.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2268
_journal_page_last               2275
_journal_paper_doi               10.1039/d0sc04949b
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C36 H30 N26 Ni2, 2(C4 H8 O)'
_chemical_formula_sum            'C44 H46 N26 Ni2 O2'
_chemical_formula_weight         1088.49
_chemical_properties_physical    Explosive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-21 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.269(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.927(2)
_cell_length_b                   20.144(4)
_cell_length_c                   10.560(2)
_cell_measurement_reflns_used    4692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.66
_cell_volume                     2510.7(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.09
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22596
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.023
_diffrn_reflns_theta_min         1.725
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0489 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.9286. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       needle
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         6037
_refine_ls_number_restraints     624
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0386P)^2^+2.1450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4217
_reflns_number_total             6037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04949b2.cif
_cod_data_source_block           2e
_cod_depositor_comments
;Adding full bibliography for 1559749--1559754.cif.

 Adding full bibliography for 1559749--1559754.cif.
;
_cod_original_cell_volume        2510.6(8)
_cod_database_code               1559754
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C4T-C3T = C3T-C2T = C2T-C1T = C2S-C1S = C3S-C2S = C4S-C3S
 1.54 with sigma of 0.01
 O1S-C1S = O1S-C4S = O1T-C1T = O1T-C4T
 1.45 with sigma of 0.01
 N21A-C26A = N21-C26 = N21A-C22A = N21-C22
 1.34 with sigma of 0.01
 C26A-C25A = C26-C25 = C25-C24 = C25A-C24A = C24A-C23A = C24-C23 = C23A-C22A =
 C23-C22
 1.38 with sigma of 0.01
 Ni1-N21A = Ni1-N21
 2.085 with sigma of 0.01
 N11-C16 = N11-C16A = N11-C12A = N11-C12
 1.34 with sigma of 0.01
 C16-C15 = C16A-C15A = C15-C14 = C15A-C14A = C14-C13 = C14A-C13A = C13-C12 =
 C13A-C12A
 1.38 with sigma of 0.01
 C4T-C1T
 2.29 with sigma of 0.02
 C4S-C1S
 2.29 with sigma of 0.02
 O1S-C3S
 2.44 with sigma of 0.02
 O1S-C2S
 2.44 with sigma of 0.02
 O1T-C2T
 2.44 with sigma of 0.02
 O1T-C3T
 2.44 with sigma of 0.02
 C1T-C3T
 2.52 with sigma of 0.02
 C2T-C4T
 2.52 with sigma of 0.02
 C1S-C3S
 2.52 with sigma of 0.02
 C2S-C4S
 2.52 with sigma of 0.02
 C22-C26
 2.32 with sigma of 0.04
 C22A-C26A
 2.32 with sigma of 0.04
 N21A-C23A
 2.36 with sigma of 0.04
 N21A-C25A
 2.36 with sigma of 0.04
 N21-C23
 2.36 with sigma of 0.04
 N21-C25
 2.36 with sigma of 0.04
 C22A-C24A
 2.39 with sigma of 0.04
 C23A-C25A
 2.39 with sigma of 0.04
 C24A-C26A
 2.39 with sigma of 0.04
 C22-C24
 2.39 with sigma of 0.04
 C23-C25
 2.39 with sigma of 0.04
 C24-C26
 2.39 with sigma of 0.04
 C16-C14
 2.39 with sigma of 0.02
 C15-C13
 2.39 with sigma of 0.02
 C14-C12
 2.39 with sigma of 0.02
 C16A-C14A
 2.39 with sigma of 0.02
 C15A-C13A
 2.39 with sigma of 0.02
 C14A-C12A
 2.39 with sigma of 0.02
 N11-C15
 2.36 with sigma of 0.02
 N11-C13
 2.36 with sigma of 0.02
 N11-C15A
 2.36 with sigma of 0.02
 N11-C13A
 2.36 with sigma of 0.02
 C16-C12
 2.32 with sigma of 0.02
 C16A-C12A
 2.32 with sigma of 0.02
3. Rigid bond restraints
 O1S, C1S, C2S, C3S, C4S, O1T, C1T, C2T, C3T, C4T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N21, N21A, C22, C22A, C23, C23A, C24, C24A, C25, C25A, C26, C26A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N11, C12, C12A, C13, C13A, C14, C14A, C15, C15A, C16, C16A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1S \\sim C1S \\sim C2S \\sim C3S \\sim C4S \\sim O1T \\sim C1T \\sim C2T \\sim
C3T \\sim C4T: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
N21 \\sim N21A \\sim C22 \\sim C22A \\sim C23 \\sim C23A \\sim C24 \\sim C24A
\\sim C25 \\sim C25A \\sim C26 \\sim C26A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
N11 \\sim C12 \\sim C12A \\sim C13 \\sim C13A \\sim C14 \\sim C14A \\sim C15
\\sim C15A \\sim C16 \\sim C16A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Sof(O1T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C3T)=
 Sof(H3TA)=Sof(H3TB)=Sof(C4T)=Sof(H4TA)=Sof(H4TB)=1-FVAR(1)
 Sof(O1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(C3S)=
 Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=FVAR(1)
 Sof(N21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=
 Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=1-FVAR(2)
 Sof(N21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=
 Sof(H25)=Sof(C26)=Sof(H26)=FVAR(2)
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=1-FVAR(3)
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=
 Sof(C16)=Sof(H16)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB), C1T(H1TA,
 H1TB), C2T(H2TA,H2TB), C3T(H3TA,H3TB), C4T(H4TA,H4TB)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C12A(H12A), C13(H13), C13A(H13A), C14(H14), C14A(H14A), C15(H15),
 C15A(H15A), C16(H16), C16A(H16A), C22(H22), C22A(H22A), C23(H23), C23A(H23A),
 C24(H24), C24A(H24A), C25(H25), C25A(H25A), C26(H26), C26A(H26A), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              11457
_olex2_submission_special_instructions 'No special instructions were received'