Diastereoselective oxidative cyclization of 1,4-dienes for the synthesis of oxetanes.
Wang, Shengxin; Zhang, Yanhua; Wang, Chao; Zong, Lili; Organic & biomolecular chemistry 24 (2026) 2660–2664; doi:10.1039/d6ob00220j

data_7161063
_publ_section_title
;
 Diastereoselective oxidative cyclization of 1,4-dienes for the synthesis
 of oxetanes.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2660
_journal_page_last               2664
_journal_paper_doi               10.1039/d6ob00220j
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C25 H26 N2 O11'
_chemical_formula_sum            'C25 H26 N2 O11'
_chemical_formula_weight         530.48
_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     direct
_audit_creation_date             2024-09-27
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-11-11 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                71.305(3)
_cell_angle_beta                 87.165(2)
_cell_angle_gamma                73.744(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5470(4)
_cell_length_b                   11.1144(7)
_cell_length_c                   16.8902(10)
_cell_measurement_reflns_used    3251
_cell_measurement_temperature    303.10
_cell_measurement_theta_max      56.714
_cell_measurement_theta_min      5.535
_cell_volume                     1287.09(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      303.10
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_number            4461
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.561
_diffrn_reflns_theta_max         66.561
_diffrn_reflns_theta_min         2.764
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  0.753056
_exptl_absorpt_correction_T_min  0.549501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1264 before and 0.0824 after correction.
 
For component 2:
 wR2(int) was 0.1207 before and 0.0774 after correction.
 The Ratio of minimum to maximum transmission is 0.73.

Final HKLF 4 output contains 34203 reflections, Rint = 0.0944
 (16236 with I > 3sig(I), Rint = 0.0885)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0958
_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^)+(0.1796P)^2^+0.3993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2923
_refine_ls_wR_factor_ref         0.3188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3221
_reflns_number_total             4461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00220j2.cif
_cod_data_source_block           4062
_cod_depositor_comments          'Adding full bibliography for 7161063.cif.'
_cod_database_code               7161063
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.874
_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:
 C11(H11), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              58022
_olex2_submission_special_instructions 'No special instructions were received'