Tandem Synthesis of 3-Halo-5-Substituted Isoxazoles from 1-Copper(I) Alkynes and Dihaloformaldoximes.
Chen, Wenwen; Wang, Bo; Liu, Nan; Huang, Dayun; Wang, Xinyan; Hu, Yuefei; Organic letters 16 (2014) 6140–; doi:10.1021/ol503008t

data_1518269
_publ_section_title
;
 Tandem Synthesis of 3-Halo-5-Substituted Isoxazoles from 1-Copper(I)
 Alkynes and Dihaloformaldoximes.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6140
_journal_paper_doi               10.1021/ol503008t
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H6 Br N O'
_chemical_formula_weight         224.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.215(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.584(3)
_cell_length_b                   4.1885(11)
_cell_length_c                   11.089(3)
_cell_measurement_reflns_used    888
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.80
_cell_measurement_theta_min      2.89
_cell_volume                     444.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4256
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.018
_diffrn_reflns_theta_min         1.839
_exptl_absorpt_coefficient_mu    4.572
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_description       Block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
; 
 Flack x determined using 381 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                1302
_reflns_number_total             2405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503008t_si_002.cif
_cod_data_source_block           mo_dm14406_0m
_cod_depositor_comments          'Adding full bibliography for 1518269.cif.'
_cod_original_cell_volume        444.5(2)
_cod_database_code               1518269
_shelx_estimated_absorpt_t_min   0.394
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2014-3
_shelx_res_checksum              73800
_shelx_hkl_checksum              83312