Enantioselective Synthesis of Spiro-oxindole-based 3,4-Dihydropyrroles via a Michael/Cyclization Cascade of 3-Aminooxindoles with 2-Enoylpyridines
Cui, Baodong; Chen, Yu; Shan, Jing; Qin, Lei; Yuan, Changlun; Wang, Yi; Han, Wen-Yong; Wan, Nanwei; Chen, Yong-Zheng; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02138K

data_7155887
_publ_section_title
;
 Enantioselective Synthesis of Spiro-oxindole-based 3,4-Dihydropyrroles
 via a Michael/Cyclization Cascade of 3-Aminooxindoles with
 2-Enoylpyridines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02138K
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H27 N3 O4 S'
_chemical_formula_weight         477.56
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-28 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.32980(10)
_cell_length_b                   9.32980(10)
_cell_length_c                   25.5998(2)
_cell_measurement_reflns_used    8568
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      71.2650
_cell_measurement_theta_min      5.1810
_cell_volume                     1929.80(3)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10333
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.333
_diffrn_reflns_theta_min         5.183
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.023(7)
_refine_ls_extinction_coef       0.0191(10)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.3062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                4775
_reflns_number_total             4820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02138k2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1929.80(4)
_cod_database_code               7155887
_shelx_estimated_absorpt_t_min   0.747
_shelx_estimated_absorpt_t_max   0.817
_shelxl_version_number           2013-4
_shelx_res_checksum              81206