Asymmetric Organocatalytic Formal [2 + 2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis
Łukasz Albrecht; Gustav Dickmeiss; Fabio Cruz Acosta; Carles Rodríguez-Escrich; Rebecca L. Davis; Karl Anker Jørgensen; Journal of the American Chemical Society 134 (2012) 2543–2546; doi:10.1021/ja211878x

data_4117440
_publ_contact_author_email       jacobo@chem.au.dk
_publ_contact_author_name        'Jacob Overgaard'
_publ_section_title
;
 Asymmetric Organocatalytic Formal [2 + 2]-Cycloadditions via Bifunctional
 H-Bond Directing Dienamine Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2543
_journal_page_last               2546
_journal_paper_doi               10.1021/ja211878x
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H26 Br N2 O2, Cl'
_chemical_formula_sum            'C25 H26 Br Cl N2 O2'
_chemical_formula_weight         501.84
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-12-09
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.6770(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.07317(17)
_cell_length_b                   8.55027(17)
_cell_length_c                   16.8646(3)
_cell_measurement_reflns_used    11010
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.4139
_cell_measurement_theta_min      2.3772
_cell_volume                     1150.80(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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      100.00(10)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -20.00   53.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864  -99.0000   90.0000 73

  2 omega  -39.00   59.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7801   57.0000 -180.0000 98

  3 omega  -83.00   14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7801  -77.0000   60.0000 97

  4 omega  -19.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864   57.0000 -120.0000 104

  5 omega  -68.00  -34.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864  -77.0000  -30.0000 34

  6 omega  -19.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864   57.0000  -30.0000 104

  7 omega  -20.00   30.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7801  -99.0000 -120.0000 50

  8 omega -102.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7801 -178.0000 -180.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_UB_11      -0.0771481000
_diffrn_orient_matrix_UB_12      -0.0076118000
_diffrn_orient_matrix_UB_13      0.0149016000
_diffrn_orient_matrix_UB_21      -0.0072101000
_diffrn_orient_matrix_UB_22      0.0826622000
_diffrn_orient_matrix_UB_23      0.0012831000
_diffrn_orient_matrix_UB_31      -0.0435210000
_diffrn_orient_matrix_UB_32      -0.0001910000
_diffrn_orient_matrix_UB_33      -0.0398090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20134
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.44
_diffrn_source                   ' 'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.4266
_exptl_crystal_size_mid          0.0791
_exptl_crystal_size_min          0.0597
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2452 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.017(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0297P)^2^+0.1385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                5080
_reflns_number_total             5449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211878x_si_002.cif
_cod_data_source_block           11jo0023s
_cod_database_code               4117440
_chemical_oxdiff_formula         'C25 H26 Br Cl N2 O2'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_refine_friedel_coverage         0.818