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_1517176
_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         'C22 H20 Br F3 N2 O2 S'
_chemical_formula_sum            'C22 H20 Br F3 N2 O2 S'
_chemical_formula_weight         513.37
_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             2014-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.832(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.3141(9)
_cell_length_b                   25.4743(19)
_cell_length_c                   14.8041(9)
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    294.67(13)
_cell_measurement_theta_max      18.3260
_cell_measurement_theta_min      3.4320
_cell_volume                     4627.4(6)
_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      294.67(13)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0488379000
_diffrn_orient_matrix_UB_12      0.0130989000
_diffrn_orient_matrix_UB_13      0.0156665000
_diffrn_orient_matrix_UB_21      0.0234659000
_diffrn_orient_matrix_UB_22      -0.0243379000
_diffrn_orient_matrix_UB_23      0.0144277000
_diffrn_orient_matrix_UB_31      0.0201398000
_diffrn_orient_matrix_UB_32      -0.0033887000
_diffrn_orient_matrix_UB_33      -0.0431080000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_unetI/netI     0.1726
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20891
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67163
_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    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.0002(2)
_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   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         9111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.2802
_refine_ls_R_factor_gt           0.0946
_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^)+(0.1153P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.3269
_reflns_number_gt                2815
_reflns_number_total             9111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501574f_si_001.cif
_cod_data_source_block           heyt0428
_cod_depositor_comments
'Adding full bibliography for 1517176--1517177.cif.'
_cod_original_cell_volume        4627.5(6)
_cod_database_code               1517176
_reflns_odcompleteness_completeness 99.80
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C23(H23A,H23B), C26(H26A,H26B),
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C21(H21), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40), C42(H42),
  C43(H43)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C44(H44A,H44B,H44C)
;