Oxidation of o-dioxime by (diacetoxyiodo)benzene: green and mild access to furoxans
Zhang, Qi; Zhao, Cheng; Zhang, Xun; He, Chunlin; Pang, Siping; New Journal of Chemistry 46 (2022) 1489–1493; doi:10.1039/D1NJ05510K

data_7061151
_publ_section_title
;
 Oxidation of o-dioxime by (diacetoxyiodo)benzene: green and mild access
 to furoxans
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1489
_journal_page_last               1493
_journal_paper_doi               10.1039/D1NJ05510K
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H8 Br2 N2 O2'
_chemical_formula_sum            'C14 H8 Br2 N2 O2'
_chemical_formula_weight         396.04
_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     dual
_audit_creation_date             2021-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-28 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                85.421(7)
_cell_angle_beta                 71.683(7)
_cell_angle_gamma                63.651(9)
_cell_formula_units_Z            2
_cell_length_a                   7.9284(18)
_cell_length_b                   8.2719(15)
_cell_length_c                   12.334(2)
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.829
_cell_measurement_theta_min      2.977
_cell_volume                     686.4(2)
_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      170
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  '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     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7147
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.542
_diffrn_reflns_theta_min         2.755
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.906
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0764 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.7698. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0327P)^2^+3.5937P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1906
_reflns_number_total             2782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05510k2.cif
_cod_data_source_block           mo_2021839_0m
_cod_depositor_comments
'Adding full bibliography for 7061151--7061152.cif.'
_cod_database_code               7061151
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.683
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 O1, N2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
N2 \\sim O1: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C13(H13), C2(H2), C11(H11), C3(H3), C6(H6), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'