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_7124352
_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             2019-04-12
_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                 94.0443(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.85118(12)
_cell_length_b                   10.39130(17)
_cell_length_c                   28.5036(5)
_cell_measurement_reflns_used    2714
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0280
_cell_measurement_theta_min      4.5130
_cell_volume                     1728.74(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -101.00  -52.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 98

  2 omega  -60.00   26.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  -30.0000 172

  3 omega   36.00   92.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 112

  4 omega    8.00   50.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 84

  5 omega   67.00  102.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   60.0000 70

  6 omega   57.00   93.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 72

  7 omega   77.00  106.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 58

  8 omega   42.00   76.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 68

  9 omega   76.00  107.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 62

 10 omega  153.00  178.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 50

 11 omega   38.00   63.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 50

 12 omega   43.00   93.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 100

 13 omega   79.00  107.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 56

 14 omega   42.00   82.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 80

 15 omega  105.00  166.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 122

 16 omega   38.00   88.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 100

 17 omega   97.00  148.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -180.0000 102

 18 omega   62.00   87.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -180.0000 50

 19 omega   75.00  102.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 54

 20 omega   78.00  173.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 190

 21 omega   40.00   90.00   0.5000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1402407000
_diffrn_orient_matrix_UB_12      -0.0137387000
_diffrn_orient_matrix_UB_13      -0.0434826000
_diffrn_orient_matrix_UB_21      0.0044267000
_diffrn_orient_matrix_UB_22      -0.1471781000
_diffrn_orient_matrix_UB_23      0.0065305000
_diffrn_orient_matrix_UB_31      -0.2235282000
_diffrn_orient_matrix_UB_32      -0.0114863000
_diffrn_orient_matrix_UB_33      -0.0316669000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6612
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.530
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92263
_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    1.296
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0635P)^2^+0.2553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2565
_reflns_number_total             3062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07114h2.cif
_cod_data_source_block           20190483
_cod_original_cell_volume        1728.74(6)
_cod_database_code               7124352
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.85
_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), C11(H11), C12(H12), C13(H13), C14(H14)
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'