DBU-Mediated [3+2] Annulation of 3-Hydroxyisoindolinones with Vinylsulfonium Salts: An Efficient Approach to Functionalized Oxazolo[2,3-a]isoindolones
Gou, Yan; Wang, Jing; Li, Na; Hou, Shanling; Cheng, Yang; Li, Yuming; New Journal of Chemistry  (2026) –; doi:10.1039/D6NJ00608F

data_7064382
_publ_section_title
;
 DBU-mediated [3+2] annulation of 3-hydroxyisoindolinones with
 vinylsulfonium salts: an efficient approach to functionalized
 oxazolo[2,3-a]isoindolones
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7609
_journal_page_last               7613
_journal_paper_doi               10.1039/D6NJ00608F
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-15 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                112.254(4)
_cell_angle_beta                 110.239(4)
_cell_angle_gamma                97.809(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4269(8)
_cell_length_b                   10.2708(11)
_cell_length_c                   10.7625(12)
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9350
_cell_measurement_theta_min      3.1630
_cell_volume                     769.74(15)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7305
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.269
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.751
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.751
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0487
_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^)+(0.1090P)^2^+0.4167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2516
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6nj00608f2.cif
_cod_data_source_block           20250115
_cod_depositor_comments
'Adding full bibliography for 7064382--7064383.cif.'
_cod_original_cell_volume        769.74(14)
_cod_database_code               7064382
_shelx_shelxl_version_number     2014/7
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C13(H13), C5(H5), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              14038
_olex2_submission_special_instructions 'No special instructions were received'