Enantioselective construction of 3-substituted 3-amino-2-oxindoles containing an N,N-ketal skeleton via organocatalyzed aza-addition of isatin imines.
Zhang, Chen; Shang, Xinye; Cheng, Yuyu; Li, Fushuai; Zhao, Hanhui; Li, Pengfei; Li, Wenjun; Organic & biomolecular chemistry 17 (2019) 8374–8378; doi:10.1039/c9ob01870k

data_7157051
_publ_section_title
;
 Enantioselective construction of 3-substituted 3-amino-2-oxindoles
 containing an N,N-ketal skeleton via organocatalyzed aza-addition of
 isatin imines.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8374
_journal_page_last               8378
_journal_paper_doi               10.1039/c9ob01870k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C23 H24 Br N5 O3'
_chemical_formula_sum            'C23 H24 Br N5 O3'
_chemical_formula_weight         498.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-18 deposited with the CCDC.    2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.4750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5473(9)
_cell_length_b                   10.6285(4)
_cell_length_c                   22.3229(10)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.35
_cell_volume                     4623.8(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.248
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.812
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0884 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.6531. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00100(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0295P)^2^+6.3331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4376
_reflns_number_total             5306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01870k2.cif
_cod_data_source_block           mo_cxy0417_0m
_cod_depositor_comments
'Adding full bibliography for 7157049--7157053.cif.'
_cod_database_code               7157051
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.631
_shelx_estimated_absorpt_t_min   0.570
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C10(H10), C12(H12), C16(H16), C17(H17), C19(H19),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              29802
_olex2_submission_special_instructions 'No special instructions were received'