Simple electrochemical synthesis of cyclic hydroxamic acids by reduction of nitroarenes.
Winter, Johannes; Lühr, Susan; Hochadel, Kyra; Gálvez-Vázquez, María de Jesús; Prenzel, Tobias; Schollmeyer, Dieter; Waldvogel, Siegfried R.; Chemical communications (Cambridge, England) 60 (2024) 7065–7068; doi:10.1039/d4cc02118e

data_7133187
_publ_section_title
;
 Simple electrochemical synthesis of cyclic hydroxamic acids by reduction
 of nitroarenes.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7065
_journal_page_last               7068
_journal_paper_doi               10.1039/d4cc02118e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C10 H11 N O3'
_chemical_formula_sum            'C10 H11 N O3'
_chemical_formula_weight         193.20
_chemical_name_systematic
;
2<i>H</i>,4<i>H</i>- 2,2-Dimethyl-4-hydroxy-benzo[<i>b</i>]-1,4-oxazin-3-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.498(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9227(7)
_cell_length_b                   5.6720(5)
_cell_length_c                   16.1656(12)
_cell_measurement_reflns_used    10411
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.02
_cell_volume                     897.35(12)
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'X-Area Integrate 1.77.0.0 (STOE, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Shelxdrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4613
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.045
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'sealed X-ray tube, 12x0.4mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0445P)^2^+0.4259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1864
_reflns_number_total             2133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02118e2.cif
_cod_data_source_block           jwi-358-2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Dual' was changed to
'dual' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133187.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7133187
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              64824
_shelx_hkl_checksum              32184