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_4030129
_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            'C17 H16 Cl N O4'
_chemical_formula_weight         333.76
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 98.632(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.411(4)
_cell_length_b                   11.214(5)
_cell_length_c                   15.479(7)
_cell_measurement_reflns_used    3797
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.19
_cell_volume                     1615.1(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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
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_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8173
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0239(17)
_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   1.044
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0434P)^2^+0.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2419
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502209f_si_002.cif
_cod_data_source_block           130902a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1615.2(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4030129