Highly enantioselective yttrium(III)-catalyzed Friedel-Crafts alkylation of B-trichloro(trifluoro)methyl aryl enones with indoles
Wentao Wang; Xiangjin Lian; Donghui Chen; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 47 (2011) 7821–; doi:10.1039/c1cc12306h

data_7106602
_publ_section_title
;
 Highly enantioselective yttrium(III)-catalyzed Friedel-Crafts alkylation
 of B-trichloro(trifluoro)methyl aryl enones with indoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              7821
_journal_paper_doi               10.1039/c1cc12306h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 Cl3 N O'
_chemical_formula_sum            'C18 H14 Cl3 N O'
_chemical_formula_weight         366.65
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6727(8)
_cell_length_b                   14.1660(7)
_cell_length_c                   5.9443(2)
_cell_measurement_reflns_used    1741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7862
_cell_measurement_theta_min      3.0506
_cell_volume                     1656.58(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega -87.00 9.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- -16.7361 -38.0000 30.0000 96

2 omega -41.00 16.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- -16.7361 77.0000 -180.0000 57
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0175074
_diffrn_orient_matrix_UB_12      0.0423529
_diffrn_orient_matrix_UB_13      0.0264195
_diffrn_orient_matrix_UB_21      0.0314794
_diffrn_orient_matrix_UB_22      0.0229204
_diffrn_orient_matrix_UB_23      0.0199368
_diffrn_orient_matrix_UB_31      0.0014517
_diffrn_orient_matrix_UB_32      0.0137413
_diffrn_orient_matrix_UB_33      -0.1146407
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5029
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.99371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0240P)^2^+0.0210P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0752
_reflns_number_gt                2497
_reflns_number_total             3111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12306h.txt
_cod_data_source_block           110107_S2_WWT
_cod_original_cell_volume        1656.56(13)
_cod_database_code               7106602