An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles
Zhang, Kuan; Han, Hua-Bin; Wang, Lele; Zhang, Ziying; Wang, Qi-Lin; Zhang, Wenjing; Bu, Zhanwei; Chemical Communications  (2019) –; doi:10.1039/C9CC07114H

data_7124353
_publ_section_title
;
 An unexpected cascade reaction of 3-hydroxyoxindoles with
 coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07114H
_journal_year                    2019
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_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
_audit_creation_date             2019-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-17 deposited with the CCDC.    2019-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.303(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5851(8)
_cell_length_b                   10.5603(5)
_cell_length_c                   9.9923(4)
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1910
_cell_measurement_theta_min      4.9520
_cell_volume                     1749.64(14)
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -84.00  -26.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  150.0000 58

  2 omega   23.00   82.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 59

  3 omega   32.00  108.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000 -120.0000 76

  4 omega   64.00  105.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 41

  5 omega  -22.00    3.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000 -120.0000 25

  6 omega   66.00  105.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 39

  7 omega   70.00  103.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 33

  8 omega  -34.00   58.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 92

  9 omega   98.00  166.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 68

 10 omega   40.00   95.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 55

 11 omega   50.00   91.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 41

 12 omega   48.00   96.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 48

 13 omega   54.00   79.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 25

 14 omega   68.00  108.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 40

 15 omega  100.00  165.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 65

 16 omega   88.00  159.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 71

 17 omega   58.00  137.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -180.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0429223000
_diffrn_orient_matrix_UB_12      0.1257099000
_diffrn_orient_matrix_UB_13      -0.0305509000
_diffrn_orient_matrix_UB_21      -0.0719386000
_diffrn_orient_matrix_UB_22      0.0404659000
_diffrn_orient_matrix_UB_23      -0.0905768000
_diffrn_orient_matrix_UB_31      -0.0402055000
_diffrn_orient_matrix_UB_32      0.0619890000
_diffrn_orient_matrix_UB_33      0.1209979000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6459
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.965
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91335
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0148(8)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0638P)^2^+0.2283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2449
_reflns_number_total             3106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07114h2.cif
_cod_data_source_block           201904106
_cod_database_code               7124353
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.886
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'