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_7061654
_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         'C25 H14 N2 O4 S Zn'
_chemical_formula_sum            'C27 H22 N2 O6 S Zn'
_chemical_formula_weight         567.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 102.15(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.115(12)
_cell_length_b                   19.40(3)
_cell_length_c                   16.472(17)
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.988
_cell_measurement_theta_min      2.962
_cell_volume                     3160(7)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.1233
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23122
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.942
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0787 before and 0.0666 after correction.
The Ratio of minimum to maximum transmission is 0.8153.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0678
_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^)+(0.1069P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2750
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02908a2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7061650--7061656.cif.'
_cod_database_code               7061654
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.837
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-C15B
 1.39 with sigma of 0.002
 N1-C15A
 1.39 with sigma of 0.002
 N1-C15B \\sim C16B-C17 \\sim C14A-C13A
 with sigma of 0.001
 N1-C15A \\sim C16A-C17 \\sim C14B-C13B
 with sigma of 0.001
3. Restrained planarity
 C16B, C14A, C13A, C15B, N1, C17
 with sigma of 0.001
 C13B, C15A, C16A, C14B, N1, C17
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
N2 \\sim C25 \\sim S1: within 3.8A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 3.8A
Uanis(C15B) \\sim Ueq, Uanis(C15A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C16B) = Uanis(C16A)
Uanis(C15B) = Uanis(C15A)
Uanis(C14B) = Uanis(C14A)
Uanis(C13B) = Uanis(C13A)
5. Rigid body (RIGU) restrains
 N2, C24, C25, S1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N2, C25, S1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(C13A)=Sof(H13A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C20(H20), C21(H21), C22(H22), C19(H19), C4(H4), C3(H3), C8(H8),
 C9(H9), C6(H6), C13B(H13B), C14B(H14B), C16B(H16B), C15B(H15B), C14A(H14A),
 C13A(H13A), C15A(H15A), C16A(H16A)
7.b Fitted hexagon refined as free rotating group:
 C18(C20,C21,C23,C22,C19)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              7914
_shelx_fab_checksum              4877
_olex2_submission_special_instructions 'No special instructions were received'