Efficient synthesis of multicyclic spirooxindoles via a cascade Michael/Michael/oxa-Michael reaction of curcumins and isatylidene malononitriles.
Yin, Xiao-Gang; Liu, Xin-Yun; Hu, Zhi-Peng; Yan, Ming; Organic & biomolecular chemistry 10 (2012) 1506–1509; doi:10.1039/c2ob06995d

data_7152225
_publ_section_title
;
 Efficient synthesis of multicyclic spirooxindoles via a cascade
 Michael/Michael/oxa-Michael reaction of curcumins and isatylidene
 malononitriles.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1506
_journal_page_last               1509
_journal_paper_doi               10.1039/c2ob06995d
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C31 H22 Cl3 N3 O3'
_chemical_formula_weight         590.87
_space_group_IT_number           14
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.205(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4462(2)
_cell_length_b                   13.9750(2)
_cell_length_c                   16.7998(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2742.27(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11287
_diffrn_reflns_theta_full        72.02
_diffrn_reflns_theta_max         72.02
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    3.348
_exptl_absorpt_correction_T_max  0.8505
_exptl_absorpt_correction_T_min  0.7307
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0557P)^2^+2.5172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                4238
_reflns_number_total             5207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob06995d.txt
_cod_data_source_block           yxg_111001
_cod_original_cell_volume        2742.29(8)
_cod_database_code               7152225