AlCl3-promoted selective Michael addition with allenoate and methyleneindolinone: synthesis of spirocyclic oxindole by using allenoate as a four-carbon component building block.
Xu, Shibo; Li, Chunju; Jia, Xueshun; Li, Jian; The Journal of organic chemistry 79 (2014) 11161–11169; doi:10.1021/jo502209f

data_4030128
_publ_section_title
;
 AlCl3-promoted selective Michael addition with allenoate and
 methyleneindolinone: synthesis of spirocyclic oxindole by using allenoate
 as a four-carbon component building block.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11161
_journal_page_last               11169
_journal_paper_doi               10.1021/jo502209f
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C23 H21 Cl2 N O4'
_chemical_formula_weight         446.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.247(9)
_cell_angle_beta                 68.697(8)
_cell_angle_gamma                71.843(8)
_cell_formula_units_Z            4
_cell_length_a                   12.287(9)
_cell_length_b                   14.357(11)
_cell_length_c                   14.460(11)
_cell_measurement_reflns_used    3674
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.46
_cell_volume                     2184(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11398
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.051(3)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         7593
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0882P)^2^+2.2155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.2048
_reflns_number_gt                5464
_reflns_number_total             7593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502209f_si_004.cif
_cod_data_source_block           130911a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030127--4030129.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4030128