Annulated Isoxazoles via [3 + 2] Cycloaddition of Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination.
Castillo-Contreras, Emmanuel B; Stahl, Alexander M.; Dake, Gregory R.; The Journal of organic chemistry 79 (2014) 7250–7255; doi:10.1021/jo501376q

data_4029824
_publ_section_title
;
 Annulated Isoxazoles via [3 + 2] Cycloaddition of Alkenyl Bromides and
 Oximoyl Chlorides and Ag(I) Promoted Elimination.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7250
_journal_page_last               7255
_journal_paper_doi               10.1021/jo501376q
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
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_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6193(4)
_cell_length_b                   10.9706(7)
_cell_length_c                   11.8576(9)
_cell_measurement_reflns_used    6396
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      66.36
_cell_measurement_theta_min      5.49
_cell_volume                     991.16(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8624
_diffrn_reflns_theta_full        66.41
_diffrn_reflns_theta_max         66.41
_diffrn_reflns_theta_min         5.49
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.8033
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0824P)^2^+0.0992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1636
_reflns_number_total             1725
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo501376q_si_001.cif
_cod_data_source_block           gd039
_cod_depositor_comments
'Adding full bibliography for 4029824--4029825.cif.'
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               4029824