Highly Efficient Hydrogen-Bonding Catalysis of the Diels-Alder Reaction of 3-Vinylindoles and Methyleneindolinones Provides Carbazolespirooxindole Skeletons
Bin Tan; Gloria Hernández-Torres; Carlos F. Barbas; Journal of the American Chemical Society 133 (2011) 12354–12357; doi:10.1021/ja203812h

data_4106552
_publ_section_title
;
 Highly Efficient Hydrogen-Bonding Catalysis of the Diels-Alder Reaction
 of 3-Vinylindoles and Methyleneindolinones Provides
 Carbazolespirooxindole Skeletons
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12354
_journal_page_last               12357
_journal_paper_doi               10.1021/ja203812h
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C26.5 H26 Br Cl N2 O5'
_chemical_formula_weight         567.85
_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            8
_cell_length_a                   47.974(4)
_cell_length_b                   9.6045(9)
_cell_length_c                   11.7572(12)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      64.62
_cell_measurement_theta_min      4.67
_cell_volume                     5417.3(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18792
_diffrn_reflns_theta_full        64.70
_diffrn_reflns_theta_max         64.70
_diffrn_reflns_theta_min         3.69
_exptl_absorpt_coefficient_mu    3.294
_exptl_absorpt_correction_T_max  0.7342
_exptl_absorpt_correction_T_min  0.3384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       rod
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_platon_squeeze_details
; 
 SQUEEZE (PLATON, A.Spek) was used to treat diffuse solvent and anion 
 contributions.  Total electron count found = 130/unit cell.  Calculated for
 4 CH2Cl2 (the re'xtal solvent) = 168/unit cell.  The intensive
 properties (density, F(000), etc.) do NOT reflect these contributions.  
;
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         8223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+16.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                7944
_reflns_number_total             8223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203812h_si_001.cif
_cod_data_source_block           barbas14a
_cod_original_formula_sum        'C26.50 H26 Br Cl N2 O5'
_cod_database_code               4106552