TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic Ketones and TMSN3
He, Yan; Xie, Yu-Yang; Wang, Ying-chun; Bin, Xiao-min; Hu, Da-chao; Wang, Hengshan; Pan, Ying-ming; RSC Adv.  (2016) –; doi:10.1039/C6RA11099A

data_7225525
_publ_section_title
;
 TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
 Ketones and TMSN3
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA11099A
_journal_year                    2016
_chemical_formula_moiety         'C9 H6 Br N O'
_chemical_formula_sum            'C9 H6 Br N O'
_chemical_formula_weight         224.06
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-23 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.114(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.441(10)
_cell_length_b                   13.965(13)
_cell_length_c                   5.949(6)
_cell_measurement_reflns_used    3152
_cell_measurement_temperature    296.15
_cell_volume                     864.0(14)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9149
_diffrn_reflns_theta_full        26.82
_diffrn_reflns_theta_max         26.82
_diffrn_reflns_theta_min         1.96
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.704
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.9803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                1151
_reflns_number_total             1850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra11099a2.cif
_cod_data_source_block           pym-hy-45
_cod_original_cell_volume        863.9(14)
_cod_database_code               7225525
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C2(H2), C5(H5), C6(H6), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'