Synthesis of Isoxazoline N-Oxides via [Hydroxy(tosyloxy)iodo]benzene (HTIB)-Mediated Oxidative N-O Coupling
Mustafa J. Raihan; Veerababurao Kavala; Pateliya Mujjamil Habib; Qiao-Zhi Guan; Chun-Wei Kuo; Ching-Fa Yao; Journal of Organic Chemistry 76 (2011) 424–434; doi:10.1021/jo1018393

data_4025981
_publ_section_title
;
 Synthesis of Isoxazoline N-Oxides via [Hydroxy(tosyloxy)iodo]benzene
 (HTIB)-Mediated Oxidative N-O Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              424
_journal_page_last               434
_journal_paper_doi               10.1021/jo1018393
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C11 H9 Cl N2 O4'
_chemical_formula_sum            'C11 H9 Cl N2 O4'
_chemical_formula_weight         268.65
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.496(2)
_cell_angle_beta                 96.783(2)
_cell_angle_gamma                106.600(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6607(3)
_cell_length_b                   7.7335(3)
_cell_length_c                   10.9132(4)
_cell_measurement_reflns_used    4616
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     579.96(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4143
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.8014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.3279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                1752
_reflns_number_total             2028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1018393_si_006.cif
_cod_data_source_block           10377
_cod_database_code               4025981