Enantioselective construction of spiro-1,3-indandiones with three stereocenters via organocatalytic Michael-aldol reaction of 2-arylideneindane-1,3-diones and nitro aldehydes
Duan, Jindian; Cheng, Jing; Li, Pengfei; Organic Chemistry Frontiers 2 (2015) 1048–; doi:10.1039/C5QO00166H

data_1553149
_publ_section_title
;
 Enantioselective construction of spiro-1,3-indandiones with three
 stereocenters via organocatalytic Michael-aldol reaction of
 2-arylideneindane-1,3-diones and nitro aldehydes
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1048
_journal_paper_doi               10.1039/C5QO00166H
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 N O6'
_chemical_formula_weight         381.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-05-21 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.85690(10)
_cell_length_b                   14.9130(2)
_cell_length_c                   23.1808(16)
_cell_measurement_reflns_used    38940
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      7.00
_cell_volume                     3753.2(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            52124
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.581
_diffrn_reflns_theta_min         7.034
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 2272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       0.0016(6)
_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   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         6840
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0978
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1978P)^2^+0.1082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2475
_refine_ls_wR_factor_ref         0.2574
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5926
_reflns_number_total             6840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00166h2.cif
_cod_data_source_block           shelx
_cod_database_code               1553149
_shelxl_version_number           2014-3
_shelx_res_checksum              18411
_shelx_hkl_checksum              56500