An asymmetric assembly of spirooxindole dihydropyranones through a direct enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with isatins.
Han, Jeng-Liang; Chang, Chia-Hao; Chemical communications (Cambridge, England) 52 (2016) 2322–2325; doi:10.1039/c5cc08883f

data_7118340
_publ_section_title
;
 An asymmetric assembly of spirooxindole dihydropyranones through a direct
 enantioselective organocatalytic vinylogous aldol-cyclization cascade
 reaction of 3-alkylidene oxindoles with isatins.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2322
_journal_page_last               2325
_journal_paper_doi               10.1039/c5cc08883f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_compound_source        Synthezied
_chemical_formula_moiety         C31H29BrN2O5
_chemical_formula_sum            'C31 H29 Br N2 O5'
_chemical_formula_weight         589.47
_chemical_melting_point          145.5(5)
_chemical_name_common            'spirooxindole dihydropyranone'
_chemical_name_systematic
'tert-butyl (S)-(2-(1-benzyl-5-bromo-4'-methyl-2,6'-dioxo-3',6'-dihydrospiro[indoline-3,2'-pyran]-5'-yl)phenyl)carbamate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-10-06 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.283(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6073(4)
_cell_length_b                   9.8229(4)
_cell_length_c                   14.4413(6)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.55
_cell_volume                     1436.76(10)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26335
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_min         2.011
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       column
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         7077
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.0413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5695
_reflns_number_total             7077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc08883f2.cif
_cod_data_source_block           11833_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '145-146' was changed to '145.5(5)' -
the average value was taken and precision was estimated.

'_exptl_absorpt_correction_type' value 'multi_scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7118340.cif.
;
_cod_database_code               7118340
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.590
_shelx_estimated_absorpt_t_max   0.867
_shelx_res_checksum              11131