Highly Diastereoselective One-Pot Synthesis of Spiro{cyclopenta[a]indene-2,2'-indene}diones from 1-Indanones and Aromatic Aldehydes
Pelayo Camps; Luis R. Domingo; Xavier Formosa; Carles Galdeano; Diana González; Diego Muñoz-Torrero; Sílvia Segalés; Mercè Font-Bardia; Xavier Solans; Journal of Organic Chemistry 71 (2006) 3464–3471; doi:10.1021/jo0600095

data_4021657
_publ_section_title
;
 Highly Diastereoselective One-Pot Synthesis of
 Spiro{cyclopenta[a]indene-2,2'-indene}diones from 1-Indanones
 and Aromatic Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3464
_journal_page_last               3471
_journal_paper_doi               10.1021/jo0600095
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C30 H22 N2 O2'
_chemical_formula_sum            'C30 H22 N2 O2'
_chemical_formula_weight         442.50
_chemical_melting_point          220.5(5)
_chemical_name_systematic
;
(1RS,2RS,3RS,3aSR,8aSR)-1,3-di(2-pyridyl)3a,8a-
dihydrospiro{cyclopenta[a]indene-2,2(1H,3H)-indene}-1,8(3H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.33(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.426(9)
_cell_length_b                   17.622(5)
_cell_length_c                   10.968(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      9
_cell_volume                     2316(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'ENRAF-NONIUS CAD4'
_diffrn_measurement_method       '\w-2\Q scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.8283
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7201
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.662
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.662
_refine_ls_R_factor_all          0.5684
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0331
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                5731
_reflns_number_total             6729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0600095si20060104_111826.cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '220-221' was changed to '220.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021657