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_7061653
_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         'C4 H4 N4 O4'
_chemical_formula_sum            'C4 H4 N4 O4'
_chemical_formula_weight         172.11
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                89.639(7)
_cell_angle_beta                 80.847(10)
_cell_angle_gamma                89.131(10)
_cell_formula_units_Z            2
_cell_length_a                   5.0887(16)
_cell_length_b                   7.8054(19)
_cell_length_c                   7.906(2)
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.846
_cell_measurement_theta_min      2.607
_cell_volume                     309.98(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3278
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_min         2.609
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0597 before and 0.0488 after correction. The Ratio of minimum to maximum transmission is 0.8738. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1239
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0320P)^2^+0.3489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                942
_reflns_number_total             1239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02908a2.cif
_cod_data_source_block           mo_20211647_0m
_cod_depositor_comments
'Adding full bibliography for 7061650--7061656.cif.'
_cod_original_cell_volume        309.99(15)
_cod_database_code               7061653
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Restrained distances
 O2-N2
 1.25 with sigma of 0.02
 O2-C1
 3 with sigma of 0.02
 N1-H1B = N1-H1A = N4-H4B = N4-H4A
 0.87 with sigma of 0.02
 O2-N2 \\sim O4-N3
 with sigma of 0.02
2. Others
 Fixed Sof: O4(0.75) O2(0.25)
;
_olex2_submission_special_instructions 'No special instructions were received'