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_4034957
_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            'C25 H22 F3 N O4 S'
_chemical_formula_weight         489.49
_space_group_crystal_system      monoclinic
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_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 110.798(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   9.9385(11)
_cell_length_c                   17.9114(19)
_cell_measurement_reflns_used    779
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2348.4(5)
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_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
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_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
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_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
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_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
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_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_point_group_measured_fraction_full 0.992
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.566
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.6616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3603
_reflns_number_total             4210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03191_si_001.cif
_cod_data_source_block           WQD694
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034957
_shelx_estimated_absorpt_t_min   0.909
_shelx_estimated_absorpt_t_max   0.944
_shelxl_version_number           2014/6
_shelx_res_checksum              40803
_shelx_hkl_checksum              80563