Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines.
Wang, Quande; Tsui, Gavin Chit; The Journal of organic chemistry 83 (2018) 2971–2979; doi:10.1021/acs.joc.7b03191

data_4034958
_publ_section_title
;
 Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic
 N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2971
_journal_page_last               2979
_journal_paper_doi               10.1021/acs.joc.7b03191
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C23 H20 F3 N O3 S'
_chemical_formula_weight         447.46
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 104.124(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   14.4419(13)
_cell_length_c                   11.0444(10)
_cell_measurement_reflns_used    787
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2062.9(3)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38647
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.574
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.9891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3356
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03191_si_002.cif
_cod_data_source_block           wqd6115a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034958
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.940
_shelxl_version_number           2014/6
_shelx_res_checksum              61499
_shelx_hkl_checksum              83613