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_7064383
_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         'C22 H17 N O2'
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2026-03-21
_audit_creation_method
;
Olex2 1.5
(compiled 2026.03.20 svn.r2bc28608 for OlexSys, GUI svn.r7524)
;
_audit_update_record
;
2026-03-24 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.825(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.236(3)
_cell_length_b                   9.0230(19)
_cell_length_c                   13.095(4)
_cell_measurement_reflns_used    2055
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.24
_cell_volume                     1678.6(7)
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2024)'
_computing_data_collection       'APEX6 V2024.9-1 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7182
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         1.996
_diffrn_source                   'Turbo X-Ray Source (TXS)'
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1136 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0416P)^2^+0.8303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1263
_reflns_number_total             1833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6nj00608f2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7064382--7064383.cif.
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               7064383
_shelx_shelxl_version_number     2025/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: O1(0.5) O2(0.5) N1(0.5) C1(0.5) C6(0.5) H6(0.5) C5(0.5) H5(0.5)
 C4(0.5) H4(0.5) C3(0.5) H3(0.5) C2(0.5) C7(0.5) C8(0.5) C11(0.5) H11(0.5)
 C10(0.5) H10(0.5) C9(0.5) C14(0.5) H14(0.5) C13(0.5) H13(0.5) C12(0.5)
 H12(0.5) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16(0.5) C22(0.5) H22(0.5)
 C21(0.5) H21(0.5) C20(0.5) H20(0.5) C19(0.5) H19(0.5) C18(0.5) H18(0.5)
 C17(0.5)
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3), C11(H11), C10(H10), C14(H14), C13(H13),
 C12(H12), C22(H22), C21(H21), C20(H20), C19(H19), C18(H18)
3.d Fitted hexagon refined as free rotating group:
 C6(C5,C4,C3,C2,C7), C11(C10,C9,C14,C13,C12), C22(C21,C20,C19,C18,C17)
;
_shelx_res_checksum              11100
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU