Copper-catalyzed three-component cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization of 1,6-enynes.
He, Yu-Tao; Li, Lian-Hua; Zhou, Zhao-Zhao; Hua, Hui-Liang; Qiu, Yi-Feng; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 16 (2014) 3896–3899; doi:10.1021/ol501574f

data_1517177
_publ_section_title
;
 Copper-catalyzed three-component
 cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization
 of 1,6-enynes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3896
_journal_page_last               3899
_journal_paper_doi               10.1021/ol501574f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C21 H19 F3 N4 O3 S'
_chemical_formula_sum            'C21 H19 F3 N4 O3 S'
_chemical_formula_weight         464.46
_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
_audit_creation_date             2014-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.901(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.421(2)
_cell_length_b                   8.6118(12)
_cell_length_c                   16.299(2)
_cell_measurement_reflns_used    1733
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.6830
_cell_measurement_theta_min      4.4640
_cell_volume                     2227.4(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details
;
  1 omega  -79.00  -34.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 30

  2 omega   -1.00   71.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 48

  3 omega -101.00  -74.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -30.0000 18

  4 omega   25.00   52.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -120.0000 18

  5 omega   29.00   93.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  -90.0000 43

  6 omega   24.00  123.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000    0.0000 66

  7 omega   48.00   85.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000    0.0000 25

  8 omega   34.00  112.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000 -180.0000 52

  9 omega   49.00   98.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 33

 10 omega   38.00   63.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 17

 11 omega  112.00  152.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 27

 12 omega   52.00  103.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 34

 13 omega   40.00   79.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000    0.0000 26

 14 omega   58.00   88.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -60.0000 20

 15 omega   53.00   78.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 17

 16 omega   45.00   99.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 36

 17 omega   92.00  176.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 56

 18 omega   64.00  109.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 30

 19 omega   42.00   79.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -90.0000 25

 20 omega   96.00  162.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 44

 21 omega   47.00   81.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   90.0000 23
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0343578000
_diffrn_orient_matrix_UB_12      -0.0881087000
_diffrn_orient_matrix_UB_13      -0.0662328000
_diffrn_orient_matrix_UB_21      0.0064001000
_diffrn_orient_matrix_UB_22      0.1540699000
_diffrn_orient_matrix_UB_23      -0.0459147000
_diffrn_orient_matrix_UB_31      0.0905305000
_diffrn_orient_matrix_UB_32      0.0222996000
_diffrn_orient_matrix_UB_33      0.0556098000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8052
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.832
_diffrn_reflns_theta_min         5.592
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.029(4)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.2052
_refine_ls_R_factor_gt           0.1296
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3403
_refine_ls_wR_factor_ref         0.4317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1469
_reflns_number_total             4080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501574f_si_003.cif
_cod_data_source_block           heyt0615
_cod_depositor_comments
'Adding full bibliography for 1517176--1517177.cif.'
_cod_original_cell_volume        2227.5(6)
_cod_database_code               1517177
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 97.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              88914
_shelx_hkl_checksum              39490
_olex2_submission_special_instructions 'No special instructions were received'