Copper-triggered three-component reaction of CF3CHN2, nitriles, and aldehydes: highly diastereoselective synthesis of CF3-substituted oxazolines and vicinal amino alcohols
Ai-Jie Cai; Yan Zheng; Jun-An Ma; Chem.Commun. 51 (2015) 8946–; doi:10.1039/c5cc02749G

data_7117185
_publ_section_title
;
 Copper-triggered three-component reaction of CF3CHN2, nitriles, and
 aldehydes: highly diastereoselective synthesis of CF3-substituted
 oxazolines and vicinal amino alcohols
;
_journal_name_full               Chem.Commun.
_journal_page_first              8946
_journal_paper_doi               10.1039/c5cc02749G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C11 H9 F3 N2 O3'
_chemical_formula_weight         274.20
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                102.598(13)
_cell_angle_beta                 92.769(13)
_cell_angle_gamma                110.155(13)
_cell_formula_units_Z            2
_cell_length_a                   5.736(3)
_cell_length_b                   7.686(5)
_cell_length_c                   15.026(9)
_cell_measurement_reflns_used    873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.679
_cell_measurement_theta_min      2.803
_cell_volume                     601.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3440
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0982
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2771
_refine_ls_wR_factor_ref         0.3071
_reflns_number_gt                1411
_reflns_number_total             2109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02749g2.cif
_cod_data_source_block           ch
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117185