Copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes.
He, Yu-Tao; Li, Lian-Hua; Yang, Yan-Fang; Zhou, Zhao-Zhao; Hua, Hui-Liang; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 16 (2014) 270–273; doi:10.1021/ol403263c

data_1513540
_publ_section_title
;
 Copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              270
_journal_page_last               273
_journal_paper_doi               10.1021/ol403263c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C14 H16 F3 N O3 S'
_chemical_formula_sum            'C14 H16 F3 N O3 S'
_chemical_formula_weight         335.34
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                79.233(11)
_cell_angle_beta                 87.668(8)
_cell_angle_gamma                88.785(9)
_cell_formula_units_Z            2
_cell_length_a                   5.7301(5)
_cell_length_b                   10.3183(14)
_cell_length_c                   13.7835(17)
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7370
_cell_measurement_theta_min      3.9020
_cell_volume                     799.86(17)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8889
_diffrn_measurement_details
;
  1 omega  -12.00   27.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000 -120.0000 26

  2 omega   79.00  104.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000   90.0000 17

  3 omega   -2.00   89.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000 -120.0000 61

  4 omega  -52.00   56.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -38.0000  -60.0000 72

  5 omega  -41.00   34.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -77.0000   90.0000 50

  6 omega   19.00   46.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000   90.0000 18
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0023201000
_diffrn_orient_matrix_UB_12      0.0550090000
_diffrn_orient_matrix_UB_13      -0.0394606000
_diffrn_orient_matrix_UB_21      -0.0121481000
_diffrn_orient_matrix_UB_22      0.0430433000
_diffrn_orient_matrix_UB_23      0.0344983000
_diffrn_orient_matrix_UB_31      0.1232802000
_diffrn_orient_matrix_UB_32      0.0043028000
_diffrn_orient_matrix_UB_33      0.0006862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5381
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         3.01
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81997
_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    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0661P)^2^+0.2170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1829
_reflns_number_gt                2345
_reflns_number_total             3585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403263c_si_001.cif
_cod_data_source_block           heyt1014
_cod_original_cell_volume        799.87(16)
_cod_database_code               1513540
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;