A Dual Lewis Base Activation Strategy for Enantioselective Carbene-Catalyzed Annulations
Javier Izquierdo; Ane Orue; Karl A. Scheidt; Journal of the American Chemical Society 135 (2013) 10634–10637; doi:10.1021/ja405833m

data_4120169
_publ_section_title
;
 A Dual Lewis Base Activation Strategy for Enantioselective
 Carbene-Catalyzed Annulations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10634
_journal_page_last               10637
_journal_paper_doi               10.1021/ja405833m
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C10 H10 O2'
_chemical_formula_sum            'C10 H10 O2'
_chemical_formula_weight         162.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_audit_creation_date             2013-05-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.710(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3733(3)
_cell_length_b                   6.0822(3)
_cell_length_c                   9.3401(4)
_cell_measurement_reflns_used    5804
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.48
_cell_measurement_theta_min      4.82
_cell_volume                     411.57(3)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      99.99
_diffrn_measured_fraction_theta_full 0.910
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.910
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6835
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.583
_diffrn_reflns_theta_min         4.818
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.6450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0646 before and 0.0336 after correction.
The Ratio of minimum to maximum transmission is 0.8571.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       plate
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1324
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.0711P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0670
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                1311
_reflns_number_total             1324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja405833m_si_004.cif
_cod_data_source_block           n2664
_cod_database_code               4120169
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C9(H9), C8(H8)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.788
_shelx_res_checksum              75074
_shelxl_version_number           2012-9