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_7117638
_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_absolute_configuration unk
_chemical_formula_moiety         'C14 H10 F3 N O'
_chemical_formula_sum            'C14 H10 F3 N O'
_chemical_formula_weight         265.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-10
_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                 104.113(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2351(7)
_cell_length_b                   5.3558(4)
_cell_length_c                   12.9094(9)
_cell_measurement_reflns_used    648
_cell_measurement_temperature    293.42(10)
_cell_measurement_theta_max      24.3150
_cell_measurement_theta_min      4.1320
_cell_volume                     619.24(8)
_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      293.42(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  -47.00    3.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   30.0000 25

  2 omega  -34.00   90.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -150.0000 62

  3 omega    9.00   47.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -180.0000 19
;
_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      -0.0113812000
_diffrn_orient_matrix_UB_12      -0.0462482000
_diffrn_orient_matrix_UB_13      -0.0528684000
_diffrn_orient_matrix_UB_21      -0.0747579000
_diffrn_orient_matrix_UB_22      0.0434176000
_diffrn_orient_matrix_UB_23      -0.0117396000
_diffrn_orient_matrix_UB_31      0.0234100000
_diffrn_orient_matrix_UB_32      0.1163322000
_diffrn_orient_matrix_UB_33      -0.0165971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2378
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75839
_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    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0431P)^2^+0.2822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                1339
_reflns_number_total             1934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05066a2.cif
_cod_data_source_block           heyt_0409
_cod_original_cell_volume        619.25(8)
_cod_database_code               7117638
_reflns_odcompleteness_completeness 99.65
_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 Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2015-04-09
_olex2_submission_special_instructions 'No special instructions were received'