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_1503333
_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         'C32 H20 F2 O3'
_chemical_formula_sum            'C32 H20 F2 O3'
_chemical_formula_weight         490.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 112.629(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8701(5)
_cell_length_b                   20.1152(11)
_cell_length_c                   12.7485(7)
_cell_measurement_reflns_used    8787
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.30
_cell_measurement_theta_min      3.36
_cell_volume                     2336.2(2)
_computing_cell_refinement
'Saint V7.53A and SADABS V2008/1 (Apex2, v2009.3-0; Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2009, 9, 0, 0'
_computing_data_reduction
'Saint V7.53A and SADABS V2008/1 (Apex2, v2009.3-0, Bruker AXS)'
_computing_molecular_graphics
' Cameron (WinGX v1.80.05 2009), Ortep (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'WinGX v1.80.05 2009 (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, 2005) 
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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, \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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15137
_diffrn_reflns_theta_full        69.63
_diffrn_reflns_theta_max         69.63
_diffrn_reflns_theta_min         4.35
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_correction_T_min  0.8860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0157(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.4610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                3804
_reflns_number_total             4198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102685u_si_002.cif
_cod_data_source_block           1394
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1503333