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_4025980
_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         'C19 H26 N2 O4'
_chemical_formula_sum            'C19 H26 N2 O4'
_chemical_formula_weight         346.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.0780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0697(3)
_cell_length_b                   7.7190(2)
_cell_length_c                   18.1460(5)
_cell_measurement_reflns_used    10297
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     1812.50(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9668
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.2356
_exptl_absorpt_correction_T_min  0.8163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0816
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1312P)^2^+1.8664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2280
_refine_ls_wR_factor_ref         0.2584
_reflns_number_gt                2297
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1018393_si_005.cif
_cod_data_source_block           11043
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025980