Enantioselective Claisen Rearrangements with a Hydrogen-Bond Donor Catalyst
Christopher Uyeda; Eric N. Jacobsen; Journal of the American Chemical Society 130 (2008) 9228–9229; doi:10.1021/ja803370x

data_4108086
_publ_section_title
;
 Enantioselective Claisen Rearrangements with a Hydrogen-Bond Donor
 Catalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9228
_journal_page_last               9229
_journal_paper_doi               10.1021/ja803370x
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac
;
(C33 H40 N5) (C32 H12 B F24) . 2(C3 H8 O)
;
_chemical_formula_moiety
;
C33 H40 N5 1+, C32 H12 B F24 1-, 2(C3 H8 O)
;
_chemical_formula_structural
;
(C33 H40 N5) (C32 H12 B F24) . 2(C3 H8 O)
;
_chemical_formula_sum            'C71 H68 B F24 N5 O2'
_chemical_formula_weight         1490.11
_chemical_name_common            CU05-038
_chemical_name_systematic
; 
Bis[(1R,2R)-2-(2-phenyl-1H-pyrrol-1-yl)cyclohexylamino]methaniminium
Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Di(propan-2-ol) Solvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 96.092(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.4974(1)
_cell_length_b                   18.8077(2)
_cell_length_c                   14.1387(1)
_cell_measurement_reflns_used    16753
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.21
_cell_volume                     3568.91(5)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction
;
SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004)
;
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1613 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50675
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1145
_refine_ls_number_reflns         16387
_refine_ls_number_restraints     220
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.6035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                13214
_reflns_number_total             16387
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja803370x-file002.cif
_cod_data_source_block           enj078
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4108086