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_7117636
_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         'C24 H22 F3 N O2'
_chemical_formula_sum            'C24 H22 F3 N O2'
_chemical_formula_weight         413.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                90.00
_cell_angle_beta                 96.885(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.4249(17)
_cell_length_b                   6.2204(3)
_cell_length_c                   20.9937(9)
_cell_measurement_reflns_used    1352
_cell_measurement_temperature    293.6(2)
_cell_measurement_theta_max      21.7380
_cell_measurement_theta_min      3.8190
_cell_volume                     4333.5(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      293.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -18.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 33

  2 omega  -49.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -150.0000 93

  3 omega  -34.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000   90.0000 95
;
_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      0.0021901000
_diffrn_orient_matrix_UB_12      -0.0164466000
_diffrn_orient_matrix_UB_13      -0.0328351000
_diffrn_orient_matrix_UB_21      0.0160779000
_diffrn_orient_matrix_UB_22      -0.0725530000
_diffrn_orient_matrix_UB_23      0.0088462000
_diffrn_orient_matrix_UB_31      -0.0139197000
_diffrn_orient_matrix_UB_32      -0.0863998000
_diffrn_orient_matrix_UB_33      -0.0012025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8148
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70281
_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    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0012(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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0674P)^2^+0.9196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                2053
_reflns_number_total             4254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05066a2.cif
_cod_data_source_block           heyt0504
_cod_original_cell_volume        4333.5(3)
_cod_database_code               7117636
_reflns_odcompleteness_completeness 99.67
_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. Uiso/Uaniso restraints and constraints
Uanis(F2') \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1') \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F1'(0.5) F2'(0.5) F3'(0.5) C13'(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
 C14'(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C15'(0.5) H15A(0.5) H15B(0.5)
 H15C(0.5) C13(0.5) H2A(0.5) H2B(0.5) H2C(0.5) F2(0.5) C15(0.5) H3A(0.5)
 H3B(0.5) H3C(0.5) F1(0.5) F3(0.5) C14(0.5) H1B(0.5) H1A(0.5) H1C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
4.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C13'(H13A,H13B,H13C), C14'(H14A,H14B,H14C), C15'(H15A,
 H15B,H15C), C13(H2A,H2B,H2C), C15(H3A,H3B,H3C), C14(H1B,H1A,H1C)
;
_olex2_date_sample_data_collection 2015-05-04
_olex2_submission_special_instructions 'No special instructions were received'