Enantioselective [4 + 1] Annulation Reactions of α-Substituted Ammonium Ylides To Construct Spirocyclic Oxindoles.
Zheng, Peng-Fei; Ouyang, Qin; Niu, Sheng-Li; Shuai, Li; Yuan, Yi; Jiang, Kun; Liu, Tian-Yu; Chen, Ying-Chun; Journal of the American Chemical Society 137 (2015) 9390–9399; doi:10.1021/jacs.5b04792

data_4124232
_publ_section_title
;
 Enantioselective [4 + 1] Annulation Reactions of \a-Substituted Ammonium
 Ylides To Construct Spirocyclic Oxindoles.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9390
_journal_page_last               9399
_journal_paper_doi               10.1021/jacs.5b04792
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H26 N2 O5 S'
_chemical_formula_weight         502.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6152(6)
_cell_length_b                   9.5235(5)
_cell_length_c                   32.448(2)
_cell_measurement_reflns_used    3022
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      29.0976
_cell_measurement_theta_min      3.2433
_cell_volume                     2662.3(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12749
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.162
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0665
_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^)+(0.0820P)^2^+0.2608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1806
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                4115
_reflns_number_total             6125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b04792_si_002.cif
_cod_data_source_block           3a
_cod_original_cell_volume        2662.2(3)
_cod_database_code               4124232
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2013-4
_shelx_res_checksum              45300
_shelx_hkl_checksum              72048