The copper-catalyzed synthesis of beta-trifluoromethylated acrylonitriles and trifluoromethyl-substituted 2H-azirines
Yu-Tao He; Qiang Wang; Jiahui Zhao; Xue-Yuan Liu; Peng-Fei Xu; Yong-Min Liang; Chem.Commun. 51 (2015) 13209–; doi:10.1039/C5cc05066A

data_7117637
_publ_section_title
;
 The copper-catalyzed synthesis of beta-trifluoromethylated acrylonitriles
 and trifluoromethyl-substituted 2H-azirines
;
_journal_name_full               Chem.Commun.
_journal_page_first              13209
_journal_paper_doi               10.1039/C5cc05066A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C21 H19 F3 N2'
_chemical_formula_sum            'C21 H19 F3 N2'
_chemical_formula_weight         356.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2015-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                71.21(2)
_cell_angle_beta                 75.39(2)
_cell_angle_gamma                79.84(2)
_cell_formula_units_Z            2
_cell_length_a                   9.987(3)
_cell_length_b                   10.061(3)
_cell_length_c                   10.1680(16)
_cell_measurement_reflns_used    1037
_cell_measurement_temperature    295.42(10)
_cell_measurement_theta_max      22.0230
_cell_measurement_theta_min      4.1560
_cell_volume                     930.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega    3.00   43.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666   57.0000  120.0000 20

  2 omega    0.00   90.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666   57.0000   30.0000 45

  3 omega    0.00   92.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666   38.0000  -60.0000 46

  4 omega  -12.00   22.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000 -120.0000 17

  5 omega  -36.00   42.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666  -57.0000  120.0000 39

  6 omega   35.00   91.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666  178.0000  -90.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0696655000
_diffrn_orient_matrix_UB_12      -0.0235870000
_diffrn_orient_matrix_UB_13      0.0075166000
_diffrn_orient_matrix_UB_21      0.0147981000
_diffrn_orient_matrix_UB_22      0.0710605000
_diffrn_orient_matrix_UB_23      -0.0197236000
_diffrn_orient_matrix_UB_31      -0.0193270000
_diffrn_orient_matrix_UB_32      -0.0009125000
_diffrn_orient_matrix_UB_33      0.0723467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_av_unetI/netI     0.1787
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6242
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.24(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1818
_refine_ls_R_factor_gt           0.0880
_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^)+(0.1454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.3307
_reflns_number_gt                1222
_reflns_number_total             3647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05066a2.cif
_cod_data_source_block           heyt0428
_cod_original_cell_volume        930.8(4)
_cod_database_code               7117637
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2015-04-28
_olex2_submission_special_instructions 'No special instructions were received'