NHC-catalyzed spiro bis-indane formation via domino Stetter-aldol-Michael and Stetter-aldol-aldol reactions.
Sánchez-Larios, Eduardo; Holmes, Janice M.; Daschner, Crystal L.; Gravel, Michel; Organic letters 12 (2010) 5772–5775; doi:10.1021/ol102685u

data_1503335
_publ_section_title
;
 NHC-catalyzed spiro bis-indane formation via domino Stetter-aldol-Michael
 and Stetter-aldol-aldol reactions.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5772
_journal_page_last               5775
_journal_paper_doi               10.1021/ol102685u
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C24 H16 O3'
_chemical_formula_sum            'C24 H16 O3'
_chemical_formula_weight         352.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL template'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0811(4)
_cell_length_b                   12.4394(4)
_cell_length_c                   12.5442(4)
_cell_measurement_reflns_used    248
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.00
_cell_measurement_theta_min      5.34
_cell_volume                     1729.12(10)
_computing_cell_refinement
'Saint and SADABS (Apex2, v2009.3-0, Bruker AXS)'
_computing_data_collection       'Apex2 (v2009.3-0, Bruker AXS)'
_computing_data_reduction
'Saint and SADABS (Apex2, v2009.3-0, Bruker AXS)'
_computing_molecular_graphics
' Cameron (WinGX v1.80.03 2008), Ortep (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'WinGX v1.80.03 2008 (L. J. Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
; SIR-2004 (M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, 
L. De Caro, C. Giacovazzo, G. Polidori and R. Spagna, J. Appl. Crystallogr. 
2005, 38, 381-388.
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '62mm 4K CCD camera on D85 goniostat'
_diffrn_measurement_device_type  'Proteum R Smart 6000 (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, \f and \w scans'
_diffrn_radiation_monochromator  'Montel200 multilayer graded optics'
_diffrn_radiation_source         'Bruker AXS FR591, fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11177
_diffrn_reflns_theta_full        64.98
_diffrn_reflns_theta_max         64.98
_diffrn_reflns_theta_min         5.01
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.9341
_exptl_absorpt_correction_T_min  0.8915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1181 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0824P)^2^+0.0632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2797
_reflns_number_total             2858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102685u_si_004.cif
_cod_data_source_block           mg1363
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               1503335