Synthesis of heterocyclic (triazole, furoxan, furazan) fused pyridazine di-N-oxides via hypervalent iodine oxidation
Zhang, Qi; He, Chunlin; Pang, Siping; New Journal of Chemistry 46 (2022) 14324–14327; doi:10.1039/D2NJ02908A

data_7061652
_publ_section_title
;
 Synthesis of heterocyclic (triazole, furoxan, furazan) fused pyridazine
 di-N-oxides via hypervalent iodine oxidation
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14324
_journal_page_last               14327
_journal_paper_doi               10.1039/D2NJ02908A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C50 H28 N4 O8 S2 Zn2, 1.5[C3H7NO]'
_chemical_formula_sum            'C54.5 H38.5 N5.5 O9.5 S2 Zn2'
_chemical_formula_weight         1117.27
_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     iterative
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                86.509(17)
_cell_angle_beta                 84.409(18)
_cell_angle_gamma                78.61(2)
_cell_formula_units_Z            2
_cell_length_a                   10.385(11)
_cell_length_b                   15.693(15)
_cell_length_c                   19.459(17)
_cell_measurement_reflns_used    9461
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.629
_cell_measurement_theta_min      2.802
_cell_volume                     3091(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27617
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.780
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.8326.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10684
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+0.6929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6910
_reflns_number_total             10684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02908a2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7061650--7061656.cif.'
_cod_original_formula_sum        'C54.50 H38.50 N5.50 O9.50 S2 Zn2'
_cod_database_code               7061652
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.689
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C11B-C9
 1.38 with sigma of 0.002
 C11A-C9
 1.38 with sigma of 0.002
 N3-C53 \\sim C51-C53 \\sim C51-C40 \\sim C8B-C40 \\sim C8B-C39 \\sim N3-C39
 with sigma of 0.001
 N3-C53 \\sim C51-C40 \\sim N3-C39 \\sim C51-C53 \\sim C8B-C39 \\sim C8B-C40
 with sigma of 0.001
 N2-C12B \\sim C12B-C11B \\sim C9-C11B \\sim C9-C10A \\sim C13A-C10A \\sim
N2-C13A
 with sigma of 0.001
 C12A-C11A \\sim C9-C11A \\sim C9-C10B \\sim C13B-C10B \\sim N2-C13B \\sim
N2-C12A
 with sigma of 0.001
3. Restrained planarity
 C41, C42, C40, C52, C38, N3
 with sigma of 0.001
 C53, C51, C8B, C39
 with sigma of 0.001
 C12B, C11B, N2, C13A, C10A, C9
 with sigma of 0.001
 C12A, C11A, N2, C9, C10B, C13B
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
N1: within 3.8A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 3.8A
Uanis(C10A) \\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(C13A) \\sim Ueq,
Uanis(C13B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C13A) = Uanis(C13B)
Uanis(C12A) = Uanis(C12B)
5. Others
 Sof(C38)=Sof(H38)=Sof(C52)=Sof(H52)=Sof(C8B)=Sof(H8B)=Sof(C39)=Sof(H39)=1-
 FVAR(1)
 Sof(C53)=Sof(H53)=Sof(C41)=Sof(H41)=Sof(C51)=Sof(H51)=Sof(C42)=Sof(H42)=FVAR(1)
 Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C10B)=Sof(H10B)=Sof(C13B)=
 Sof(H13B)=1-FVAR(2)
 Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C13A)=Sof(H13A)=Sof(C10A)=
 Sof(H10A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C45(H45), C33(H33), C6(H6), C29(H29), C16(H16), C46(H46),
 C31(H31), C5(H5), C19(H19), C44(H44), C22(H22), C47(H47), C28(H28), C35(H35),
 C34(H34), C21(H21), C11B(H11B), C12B(H12B), C4(H4), C7(H7), C10B(H10B),
 C13B(H13B), C38(H38), C52(H52), C8B(H8B), C39(H39), C53(H53), C41(H41),
 C51(H51), C42(H42), C12A(H12A), C11A(H11A), C13A(H13A), C10A(H10A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              26080
_shelx_fab_checksum              96299
_olex2_submission_special_instructions 'No special instructions were received'