Scalable ultrasound-assisted synthesis of hydroxy imidazole N-oxides and evaluation of their anti-proliferative activities; mechanistic insights into the deoximation of dioximes
Mukhia, Munna; Rai, Sagar; Rai, Yachna; Chakraborty, Koushik; Dey, Sangita; Tiwary, Bipransh Kumar; Brahman, Dhiraj; Kumar, Anoop; Pradhan, Kiran; RSC Advances 15 (2025) 938–946; doi:10.1039/D4RA07893D

data_7249786
_publ_section_title
;
 Scalable ultrasound-assisted synthesis of hydroxy imidazole N-oxides and
 evaluation of their anti-proliferative activities; mechanistic insights
 into the deoximation of dioximes
;
_journal_issue                   2
_journal_name_full               'RSC Advances'
_journal_page_first              938
_journal_page_last               946
_journal_paper_doi               10.1039/D4RA07893D
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_chemical_name_systematic
'1-hydroxy-2-(naphthalen-1-yl)-1H-imidazole 3-oxide'
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-10-04 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.371(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9333(5)
_cell_length_b                   10.9751(6)
_cell_length_c                   11.0707(6)
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    304(2)
_cell_measurement_theta_max      25.035
_cell_measurement_theta_min      2.613
_cell_volume                     1085.39(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'WinGX v2018.3'
_computing_publication_material  'WinGX v2018.3'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      304(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.035
_diffrn_reflns_theta_max         25.035
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0480P)^2^+0.3245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1693
_reflns_number_total             1923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07893d2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249786
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              40791