Halonium Ion Mediated Synthesis of 2-Halomethylene-3-oxoketoxime Derivatives from Isoxazoline N-Oxides
Mustafa J. Raihan; R. R. Rajawinslin; Veerababurao Kavala; Chun-Wei Kuo; Ting-Shen Kuo; Chiu-Hui He; Hsiu-Ni Huang; Ching-Fa Yao; Journal of Organic Chemistry 78 (2013) 8872–8879; doi:10.1021/jo401283x

data_4028544
_publ_section_title
;
 Halonium Ion Mediated Synthesis of 2-Halomethylene-3-oxoketoxime
 Derivatives from Isoxazoline N-Oxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8872
_journal_page_last               8879
_journal_paper_doi               10.1021/jo401283x
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C13 H13 Br N2 O4'
_chemical_formula_sum            'C13 H13 Br N2 O4'
_chemical_formula_weight         341.16
_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                79.235(2)
_cell_angle_beta                 65.400(2)
_cell_angle_gamma                78.023(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6888(3)
_cell_length_b                   9.1890(3)
_cell_length_c                   9.4216(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     664.79(4)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5578
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    3.107
_exptl_absorpt_correction_T_max  0.5615
_exptl_absorpt_correction_T_min  0.2847
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.0403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                2119
_reflns_number_total             2325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401283x_si_001.cif
_cod_data_source_block           ch13863
_cod_database_code               4028544