Enantioselective Construction of Spirocyclic Oxindole Derivatives with Multiple Stereocenters via an Organocatalytic Michael/Aldol/Hemiacetalization Cascade Reaction.
Zhu, Luyi; Chen, Qiliang; Shen, Dan; Zhang, Weihao; Shen, Cong; Zeng, Xiaofei; Zhong, Guofu; Organic letters 18 (2016) 2387–2390; doi:10.1021/acs.orglett.6b00873

data_1555553
_publ_section_title
;
 Enantioselective Construction of Spirocyclic Oxindole Derivatives with
 Multiple Stereocenters via an Organocatalytic
 Michael/Aldol/Hemiacetalization Cascade Reaction.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2387
_journal_page_last               2390
_journal_paper_doi               10.1021/acs.orglett.6b00873
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         C18H22FNO4
_chemical_formula_sum            'C18 H22 F N O4'
_chemical_formula_weight         335.37
_chemical_melting_point          ?
_chemical_name_common
;
ethyl (2'S,3R,4'S,5'S)-2'-ethyl-5-fluoro-5'-methyl-2-oxo-5',6'
-dihydro-2'H,4'H-spiro[indoline-3,3'-pyran]-4'-carboxylate
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7821(3)
_cell_length_b                   11.5835(4)
_cell_length_c                   14.8591(5)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      74.5241
_cell_measurement_theta_min      3.8160
_cell_volume                     1683.70(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14932
_diffrn_reflns_theta_full        74.52
_diffrn_reflns_theta_max         74.52
_diffrn_reflns_theta_min         4.84
_exptl_absorpt_coefficient_mu    0.836
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.0200
_exptl_crystal_size_mid          0.0100
_exptl_crystal_size_min          0.0100
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(14)
_refine_ls_extinction_coef       0.0240(15)
_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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.1716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                3243
_reflns_number_total             3378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00873_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'unknown' was changed to
'?' -- the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1555553