Catalytic Asymmetric Construction of Tetrahydroquinoline-Based Spirooxindole Framework via a Diastereo- and Enantioselective Decarboxylative [4+2] Cycloaddition
Mei, Guang-Jian; Li, Dan; Zhou, Gui-Xiang; Shi, Qian; Cao, Zheng; Shi, Feng; Chem. Commun.  (2017) –; doi:10.1039/C7CC05595A

data_7120574
_publ_section_title
;
 Catalytic Asymmetric Construction of Tetrahydroquinoline-Based
 Spirooxindole Framework via a Diastereo- and Enantioselective
 Decarboxylative [4+2] Cycloaddition
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC05595A
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H28 N2 O6 S'
_chemical_formula_sum            'C30 H28 N2 O6 S'
_chemical_formula_weight         544.60
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1pbhk2
_audit_creation_date             2017-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-06-29 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0717(2)
_cell_length_b                   12.8155(2)
_cell_length_c                   23.4747(5)
_cell_measurement_reflns_used    6145
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.77
_cell_volume                     2729.13(9)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_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  0.0590
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14759
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.678
_diffrn_reflns_theta_min         3.766
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.3889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1500 before and 0.0860 after correction. The Ratio of minimum to maximum transmission is 0.5163. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.058(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.2364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                4585
_reflns_number_total             4909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05595a2.cif
_cod_data_source_block           cu_dm17218_0m
_cod_database_code               7120574
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.742
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C25(H25), C26(H26), C28(H28), C29(H29)
2.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              15419
_shelx_hkl_checksum              58861
_olex2_submission_special_instructions 'No special instructions were received'