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_1559753
_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         '2(C18 H15 Fe N13), 2(C4 H8 O1), C2 H3 N'
_chemical_formula_sum            'C46 H49 Fe2 N27 O2'
_chemical_formula_weight         1123.82
_chemical_properties_physical    Air-sensitive,Explosive
_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
_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                91.221(6)
_cell_angle_beta                 106.188(6)
_cell_angle_gamma                99.178(7)
_cell_formula_units_Z            2
_cell_length_a                   11.034(4)
_cell_length_b                   13.414(6)
_cell_length_c                   18.758(8)
_cell_measurement_reflns_used    1627
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.62
_cell_measurement_theta_min      2.27
_cell_volume                     2625.8(19)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       'COSMO (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_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      100.04
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14524
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        24.709
_diffrn_reflns_theta_max         24.709
_diffrn_reflns_theta_min         1.133
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0570 before and 0.0423 after correction. The Ratio of minimum to maximum transmission is 0.7606. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.037
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     842
_refine_ls_number_reflns         8515
_refine_ls_number_restraints     590
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1470
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1196P)^2^+0.6232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.2186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4540
_reflns_number_total             8515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04949b2.cif
_cod_data_source_block           2b
_cod_depositor_comments
;Adding full bibliography for 1559749--1559754.cif.

 Adding full bibliography for 1559749--1559754.cif.
;
_cod_original_cell_volume        2625.7(19)
_cod_database_code               1559753
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2S-C10S = O2S-C7S = O1S-C3S = O1S-C6S
 1.45 with sigma of 0.01
 O2T-C10T = O2T-C7T = O1T-C3T = O1T-C6T
 1.45 with sigma of 0.01
 C9S-C10S = C9S-C8S = C8S-C7S = C4S-C3S = C5S-C4S = C6S-C5S
 1.54 with sigma of 0.01
 C9T-C10T = C9T-C8T = C8T-C7T = C4T-C3T = C5T-C4T = C6T-C5T
 1.54 with sigma of 0.01
 C7S-C10S
 2.29 with sigma of 0.02
 C7T-C10T
 2.29 with sigma of 0.02
 C6S-C3S
 2.29 with sigma of 0.02
 C6T-C3T
 2.29 with sigma of 0.02
 O2S-C8S
 2.44 with sigma of 0.02
 O2T-C8T
 2.44 with sigma of 0.02
 O2S-C9S
 2.44 with sigma of 0.02
 O2T-C9T
 2.44 with sigma of 0.02
 O1S-C5S
 2.44 with sigma of 0.02
 O1T-C5T
 2.44 with sigma of 0.02
 O1S-C4S
 2.44 with sigma of 0.02
 O1T-C4T
 2.44 with sigma of 0.02
 C10S-C8S
 2.52 with sigma of 0.02
 C10T-C8T
 2.52 with sigma of 0.02
 C9S-C7S
 2.52 with sigma of 0.02
 C9T-C7T
 2.52 with sigma of 0.02
 C3S-C5S
 2.52 with sigma of 0.02
 C3T-C5T
 2.52 with sigma of 0.02
 C6S-C4S
 2.52 with sigma of 0.02
 C6T-C4T
 2.52 with sigma of 0.02
3. Rigid bond restraints
 N51, N51A, C52, C52A, C53, C53A, C54, C54A, C55, C55A, C56, C56A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2S, C7S, C8S, C9S, C10S, O2T, C7T, C8T, C9T, C10T
 with sigma for 1-2 distances of 0.03 and sigma for 1-3 distances of 0.03
 O1S, C3S, C4S, C5S, C6S, O1T, C3T, C4T, C5T, C6T
 with sigma for 1-2 distances of 0.03 and sigma for 1-3 distances of 0.03
4. Uiso/Uaniso restraints and constraints
N51 \\sim N51A \\sim C52 \\sim C52A \\sim C53 \\sim C53A \\sim C54 \\sim C54A
\\sim C55 \\sim C55A \\sim C56 \\sim C56A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
O2S \\sim C7S \\sim C8S \\sim C9S \\sim C10S \\sim O2T \\sim C7T \\sim C8T
\\sim C9T \\sim C10T: within 2A with sigma of 0.03 and sigma for terminal atoms
of 0.06
O1S \\sim C3S \\sim C4S \\sim C5S \\sim C6S \\sim O1T \\sim C3T \\sim C4T \\sim
C5T \\sim C6T: within 2A with sigma of 0.03 and sigma for terminal atoms of 0.06
5. Same fragment restrains
{N51, C52, C53, C54, C55, C56} sigma for 1-2: 0.02, 1-3: 0.04
as
{N51A, C52A, C53A, C54A, C55A, C56A}
6. Others
 Sof(N51A)=Sof(C52A)=Sof(H52A)=Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(H54A)=
 Sof(C55A)=Sof(H55A)=Sof(C56A)=Sof(H56A)=1-FVAR(1)
 Sof(N51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=Sof(C55)=
 Sof(H55)=Sof(C56)=Sof(H56)=FVAR(1)
 Sof(O2T)=Sof(C7T)=Sof(H7TA)=Sof(H7TB)=Sof(C8T)=Sof(H8TA)=Sof(H8TB)=Sof(C9T)=
 Sof(H9TA)=Sof(H9TB)=Sof(C10T)=Sof(H10C)=Sof(H10D)=1-FVAR(2)
 Sof(O2S)=Sof(C7S)=Sof(H7SA)=Sof(H7SB)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=Sof(C9S)=
 Sof(H9SA)=Sof(H9SB)=Sof(C10S)=Sof(H10A)=Sof(H10B)=FVAR(2)
 Sof(O1T)=Sof(C3T)=Sof(H3TA)=Sof(H3TB)=Sof(C4T)=Sof(H4TA)=Sof(H4TB)=Sof(C5T)=
 Sof(H5TA)=Sof(H5TB)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=1-FVAR(3)
 Sof(O1S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(C5S)=
 Sof(H5SA)=Sof(H5SB)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C4S(H4SA,H4SB), C5S(H5SA,H5SB), C6S(H6SA,H6SB), C3T(H3TA,
 H3TB), C4T(H4TA,H4TB), C5T(H5TA,H5TB), C6T(H6TA,H6TB), C7S(H7SA,H7SB),
 C8S(H8SA,H8SB), C9S(H9SA,H9SB), C10S(H10A,H10B), C7T(H7TA,H7TB), C8T(H8TA,
 H8TB), C9T(H9TA,H9TB), C10T(H10C,H10D)
7.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
  C52A(H52A), C53A(H53A), C54A(H54A), C55A(H55A), C56A(H56A), C52(H52),
 C53(H53), C54(H54), C55(H55), C56(H56), C62(H62), C63(H63), C64(H64), C65(H65),
  C66(H66), C72(H72), C73(H73), C74(H74), C75(H75), C76(H76)
7.c Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              65332
_olex2_submission_special_instructions 'No special instructions were received'