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_7117639
_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         'C15 H10 F3 N O'
_chemical_formula_sum            'C15 H10 F3 N O'
_chemical_formula_weight         277.24
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-20
_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                90.00
_cell_angle_beta                 92.84(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.226(3)
_cell_length_b                   13.605(4)
_cell_length_c                   7.270(2)
_cell_measurement_reflns_used    665
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      22.1390
_cell_measurement_theta_min      4.0760
_cell_volume                     1306.6(6)
_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      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    7.00   37.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000    0.0000 15

  2 omega   -1.00   23.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 12

  3 omega  -14.00   86.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   19.0000   60.0000 50

  4 omega   -8.00   24.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  150.0000 16

  5 omega  -19.00   63.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -99.0000  120.0000 41

  6 omega  -46.00   42.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000 -120.0000 44

  7 omega   49.00   77.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  178.0000  -90.0000 14
;
_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      -0.0345076000
_diffrn_orient_matrix_UB_12      0.0127301000
_diffrn_orient_matrix_UB_13      0.0676844000
_diffrn_orient_matrix_UB_21      -0.0247523000
_diffrn_orient_matrix_UB_22      -0.0459124000
_diffrn_orient_matrix_UB_23      -0.0126971000
_diffrn_orient_matrix_UB_31      0.0329283000
_diffrn_orient_matrix_UB_32      -0.0210519000
_diffrn_orient_matrix_UB_33      0.0693409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1576
_diffrn_reflns_av_unetI/netI     0.1566
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8091
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38595
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.2202
_refine_ls_R_factor_gt           0.1085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1865P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2646
_refine_ls_wR_factor_ref         0.3752
_reflns_number_gt                887
_reflns_number_total             2559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05066a2.cif
_cod_data_source_block           wangq0518
_cod_original_cell_volume        1306.5(6)
_cod_database_code               7117639
_reflns_odcompleteness_completeness 99.68
_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:
 C2(H2), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2015-05-18
_olex2_submission_special_instructions 'No special instructions were received'