Copper-catalyzed endo-type trifluoromethylarylation of alkynes
Jun Xu; Yun-Long Wang; Tian-Jun Gong; Bin Xiao; Yao Fu; Chem.Commun. 50 (2014) 12915–; doi:10.1039/C4cc05692B

data_7115812
_publ_section_title
;
 Copper-catalyzed endo-type trifluoromethylarylation of alkynes
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_journal_name_full               Chem.Commun.
_journal_page_first              12915
_journal_paper_doi               10.1039/C4cc05692B
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H15 F3 O'
_chemical_formula_sum            'C18 H15 F3 O'
_chemical_formula_weight         304.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   38.6451(16)
_cell_length_b                   18.5006(7)
_cell_length_c                   8.3788(3)
_cell_measurement_reflns_used    1686
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.2494
_cell_measurement_theta_min      4.5730
_cell_volume                     5990.5(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3225
_diffrn_reflns_theta_full        69.38
_diffrn_reflns_theta_max         69.38
_diffrn_reflns_theta_min         4.58
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_T_max  0.7709
_exptl_absorpt_correction_T_min  0.7283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.00029(8)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1929
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0896P)^2^+4.6349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                1770
_reflns_number_total             1929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05692b2.cif
_cod_data_source_block           xj131024-1
_cod_database_code               7115812
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H16(0.077) H12(0.07) H15(0.077) H3(0.098) H1(0.095) H13(0.072)
 H2(0.101) H18A(0.135) H18C(0.135) H18B(0.135) H6(0.078) H8B(0.092) H8A(0.092)
 H7A(0.097) H7B(0.097)
 Fixed X: H16(0.9093) H12(0.9027) H15(0.9566) H3(0.7535) H1(0.798) H13(0.95)
 H2(0.7494) H18A(0.9838) H18C(1.0215) H18B(1.0042) H6(0.8522) H8B(0.8444)
 H8A(0.8336) H7A(0.7885) H7B(0.813)
 Fixed Y: H16(0.0503) H12(0.2632) H15(0.0439) H3(0.1794) H1(0.1216)
 H13(0.2569) H2(0.1469) H18A(0.2216) H18C(0.1925) H18B(0.2411) H6(0.1278)
 H8B(0.1967) H8A(0.1206) H7A(0.1942) H7B(0.2556)
 Fixed Z: H16(0.3496) H12(0.2698) H15(0.181) H3(0.4305) H1(0.0207) H13(0.1028)
 H2(0.1674) H18A(-0.1237) H18C(-0.0986) H18B(0.0322) H6(0.1378) H8B(0.7945)
 H8A(0.7285) H7A(0.6691) H7B(0.607)
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