One-pot tandem double-aldol reaction/aza-addition of acetylacetamides and o-phthalaldehyde leading to spiroindan-2,2'-pyrrolidines.
Cheng, Xin; Liang, Fushun; Shi, Fan; Zhang, Lei; Liu, Qun; Organic letters 11 (2009) 93–96; doi:10.1021/ol802507y

data_1503743
_publ_section_title
;
 One-pot tandem double-aldol reaction/aza-addition of acetylacetamides and
 o-phthalaldehyde leading to spiroindan-2,2'-pyrrolidines.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              93
_journal_page_last               96
_journal_paper_doi               10.1021/ol802507y
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C22 H22 Cl N O3'
_chemical_formula_sum            'C22 H22 Cl N O3'
_chemical_formula_weight         383.86
_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                 98.251(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.5345(15)
_cell_length_b                   13.0337(15)
_cell_length_c                   24.721(3)
_cell_measurement_reflns_used    7874
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      1.6
_cell_volume                     3996.9(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       '\w 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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21868
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9527
_exptl_absorpt_correction_T_min  0.9468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         2.015
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         7874
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0817
_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^)+(0.0916P)^2^+1.9253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2302
_reflns_number_gt                4942
_reflns_number_total             7874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802507y_si_002.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503743