Enantioselective Construction of Tetrahydroquinolin-5-one-Based Spirooxindole Scaffold via an Organocatalytic Asymmetric Multicomponent [3 + 3] Cyclization.
Zhu, Qiu-Ning; Zhang, Yu-Chen; Xu, Meng-Meng; Sun, Xiao-Xue; Yang, Xue; Shi, Feng; The Journal of organic chemistry 81 (2016) 7898–7907; doi:10.1021/acs.joc.6b01598

data_4037146
_publ_section_title
;
 Enantioselective Construction of Tetrahydroquinolin-5-one-Based
 Spirooxindole Scaffold via an Organocatalytic Asymmetric Multicomponent
 [3 + 3] Cyclization.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7898
_journal_page_last               7907
_journal_paper_doi               10.1021/acs.joc.6b01598
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H30 N4 O3'
_chemical_formula_sum            'C33 H30 N4 O3'
_chemical_formula_weight         530.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.7790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.0719(7)
_cell_length_b                   9.2396(2)
_cell_length_c                   20.2331(4)
_cell_measurement_reflns_used    3494
_cell_measurement_temperature    296
_cell_measurement_theta_max      47.777
_cell_measurement_theta_min      2.929
_cell_volume                     5642.0(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21205
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.706
_diffrn_reflns_theta_min         2.320
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1056 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.7784.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_coef       0.00069(9)
_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   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         8811
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0905P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_full    0.706
_reflns_Friedel_fraction_max     0.684
_reflns_number_gt                6617
_reflns_number_total             8811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01598_si_002.cif
_cod_data_source_block           cu_dm15841_0m
_cod_database_code               4037146
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3A(H3AA,H3AB)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C23(H23A,H23B), C9A(H9AA,H9AB), C21A(H21C,H21D),
 C23A(H23C,H23D)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C28(H28), C29(H29), C31(H31), C32(H32), C4A(H4A), C5A(H5A), C6A(H6A),
  C7A(H7A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C28A(H28A), C29A(H29A), C31A(H31A), C32A(H32A)
2.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C25A(H25D,H25E,
 H25F), C26A(H26D,H26E,H26F), C33A(H33D,H33E,H33F)
;
_shelx_res_checksum              38247
_shelx_hkl_checksum              51452
_olex2_submission_special_instructions 'No special instructions were received'