Synthesis of spiropyrrolidine oxindoles via Ag-catalyzed stereo- and regioselective 1,3-dipolar cycloaddition of indole-based azomethine ylides with chalcones
Yue, Guizhou; Wu, Yao; Dou, Zhengjie; Chen, Huabao; Yin, Zhongqiong; Song, Xu; He, ChangLiang; Wang, Xianxiang; Feng, Juhua; Zhang, Zuming; Zou, Ping; Lu, Cuifen; New Journal of Chemistry 42 (2018) 20024–; doi:10.1039/C8NJ04492A

data_7057934
_publ_section_title
;
 Synthesis of spiropyrrolidine oxindoles via Ag-catalyzed stereo- and
 regioselective 1,3-dipolar cycloaddition of indole-based azomethine
 ylides with chalcones
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20024
_journal_paper_doi               10.1039/C8NJ04492A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C26 H22 N2 O4, C2 H6 O'
_chemical_formula_sum            'C28 H28 N2 O5'
_chemical_formula_weight         472.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-09-03 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                96.327(5)
_cell_angle_beta                 103.909(6)
_cell_angle_gamma                106.988(6)
_cell_formula_units_Z            2
_cell_length_a                   8.7731(6)
_cell_length_b                   12.3585(8)
_cell_length_c                   12.5316(9)
_cell_measurement_reflns_used    3072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0650
_cell_measurement_theta_min      3.5150
_cell_volume                     1237.26(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -83.00   12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -77.0000  -90.0000 95

  2 omega  -42.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231   77.0000   30.0000 94

  3 omega  -25.00   24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -99.0000  150.0000 49

  4 omega  -87.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231 -178.0000   60.0000 25

  5 omega  -52.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -38.0000    0.0000 31

  6 omega    0.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000 -180.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0113288000
_diffrn_orient_matrix_UB_12      0.0545911000
_diffrn_orient_matrix_UB_13      0.0010187000
_diffrn_orient_matrix_UB_21      -0.0561774000
_diffrn_orient_matrix_UB_22      -0.0152437000
_diffrn_orient_matrix_UB_23      0.0324770000
_diffrn_orient_matrix_UB_31      0.0671024000
_diffrn_orient_matrix_UB_32      0.0230279000
_diffrn_orient_matrix_UB_33      0.0497774000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9081
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0655P)^2^+0.0303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                3263
_reflns_number_total             4342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8nj04492a2.cif
_cod_data_source_block           161228_s1_lgz_m
_cod_depositor_comments          'Adding full bibliography for 7057934.cif.'
_cod_original_cell_volume        1237.27(14)
_cod_database_code               7057934
_chemical_oxdiff_formula         c12h12n2o3
_reflns_odcompleteness_completeness 99.84
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C23(H23), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2A), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'