Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates
Zhao, Liang-Liang; Li, Xing-Shuo; Cao, Li-Li; Zhang, Rui; Shi, Xiao-Qian; Qi, Jing; Chem. Commun.  (2017) –; doi:10.1039/C7CC02753B

data_7120113
_publ_section_title
;
 Access to dihydropyridinones and spirooxindoles: application of
 N-heterocyclic carbene-catalyzed [3+3] annulation of enals and
 oxindole-derived enals with 2-aminoacrylates
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02753B
_journal_year                    2017
_chemical_formula_moiety         'C29 H26 N2 O6 S'
_chemical_formula_sum            'C29 H26 N2 O6 S'
_chemical_formula_weight         530.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-01-11 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.444(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4870(4)
_cell_length_b                   25.8357(6)
_cell_length_c                   9.2054(3)
_cell_measurement_reflns_used    2442
_cell_measurement_temperature    289.56(10)
_cell_measurement_theta_max      26.0790
_cell_measurement_theta_min      3.6650
_cell_volume                     2559.86(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.56(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8843
_diffrn_measurement_details
;
  1 omega   -1.00   26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -30.0000 27

  2 omega  -10.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   90.0000 95

  3 omega   76.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   60.0000 26

  4 omega  -47.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  -30.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0252207000
_diffrn_orient_matrix_UB_12      0.0055990000
_diffrn_orient_matrix_UB_13      0.0584153000
_diffrn_orient_matrix_UB_21      -0.0282127000
_diffrn_orient_matrix_UB_22      0.0226484000
_diffrn_orient_matrix_UB_23      -0.0407758000
_diffrn_orient_matrix_UB_31      -0.0539573000
_diffrn_orient_matrix_UB_32      -0.0144744000
_diffrn_orient_matrix_UB_33      -0.0410399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10038
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.7922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                3638
_reflns_number_total             5033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc02753b2.cif
_cod_data_source_block           duanxiaoy_1212_1
_cod_original_cell_volume        2559.85(14)
_cod_database_code               7120113
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(C21') \\sim Ueq, Uanis(C22') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: O4(0.8) C21(0.8) H21A(0.8) H21B(0.8) C22(0.8) H22A(0.8) H22B(0.8)
 H22C(0.8) O4'(0.2) C21'(0.2) H21C(0.2) H21D(0.2) C22'(0.2) H22D(0.2) H22E(0.2)
 H22F(0.2)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C21(H21A,H21B), C21'(H21C,H21D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C24(H24), C25(H25), C27(H27), C28(H28)
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C22(H22A,H22B,H22C), C22'(H22D,H22E,H22F)
;
_olex2_date_sample_data_collection 2016-12-12
_olex2_submission_special_instructions 'No special instructions were received'