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_7124356
_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         '2(C32 H35 N3 O6)'
_chemical_formula_sum            'C64 H70 N6 O12'
_chemical_formula_weight         1115.26
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-18 deposited with the CCDC.    2019-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                108.369(2)
_cell_angle_beta                 95.406(2)
_cell_angle_gamma                104.122(2)
_cell_formula_units_Z            2
_cell_length_a                   11.9272(7)
_cell_length_b                   15.6713(9)
_cell_length_c                   18.1611(11)
_cell_measurement_reflns_used    3194
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.19
_cell_volume                     3069.8(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.167
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1240 before and 0.0782 after correction. The Ratio of minimum to maximum transmission is 0.8312. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0100(14)
_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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     758
_refine_ls_number_reflns         12523
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1863
_refine_ls_R_factor_gt           0.0877
_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^)+(0.1173P)^2^+2.1048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2123
_refine_ls_wR_factor_ref         0.2763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5898
_reflns_number_total             12523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07114h2.cif
_cod_data_source_block           a_CCDC1
_cod_database_code               7124356
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.988
_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 C(H,H,H,H,H,H) groups
2. Restrained distances
 C26'-C28'
 1.55 with sigma of 0.02
 C27-C28
 2.6 with sigma of 0.02
 C28-C26
 1.5 with sigma of 0.02
 C1B-C1A
 1.5 with sigma of 0.02
3. Rigid bond restraints
 C26', C28'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C26) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.008 and sigma for
terminal atoms of 0.01
Uanis(C26') \\sim Ueq, Uanis(C28') \\sim Ueq: with sigma of 0.008 and sigma for
terminal atoms of 0.01
Uanis(C28') = Uanis(C1A)
Uanis(C26') = Uanis(C1B)
5. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1B)=Sof(H1B)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=1-FVAR(1)
 Sof(C26')=Sof(H26')=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28')=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=FVAR(1)
6.a Riding coordinates:
 C27'(H27D,H27E,H27F)
6.b Ternary CH refined with riding coordinates:
 C15(H15), C17(H17), C26(H26), C30(H30), C1B(H1B), C15'(H15'), C17'(H17'),
 C26'(H26'), C30'(H30')
6.c Secondary CH2 refined with riding coordinates:
 C16(H16C,H16D), C16'(H16A,H16B)
6.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), N3(H3A), C2'(H2'), C3'(H3'), C4'(H4'),
 C5'(H5'), C8'(H8'), C9'(H9'), C10'(H10'), C11'(H11'), C19'(H19'), C20'(H20'),
 C21'(H21'), C22'(H22'), C23'(H23'), N3'(H3'A)
6.e Idealised Me refined as rotating group:
 C24(H24D,H24E,H24F), C27(H27G,H27H,H27I), C28(H28D,H28E,H28F), C31(H31D,H31E,
 H31F), C32(H32D,H32E,H32F), C1A(H1AA,H1AB,H1AC), C24'(H24A,H24B,H24C),
 C27'(H27A,H27B,H27C), C28'(H28A,H28B,H28C), C31'(H31A,H31B,H31C), C32'(H32A,
 H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'