Annulative endoperoxidation of tetronates.
Rahimi, Najmeh; Sehrish, Saba; Akompong, Samuel K.; Barnes, Bayler G.; Windorff, Cory J.; Talipov, Marat R.; Tello-Aburto, Rodolfo; Organic & biomolecular chemistry 23 (2025) 7719–7723; doi:10.1039/d5ob00663e

data_7160663
_publ_section_title
;
 Annulative endoperoxidation of tetronates.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7719
_journal_page_last               7723
_journal_paper_doi               10.1039/d5ob00663e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C12 H16 O6'
_chemical_formula_sum            'C12 H16 O6'
_chemical_formula_weight         256.25
_chemical_name_systematic
'(+-)-methyl (3aR,5R,5aS,9aS)-3a-hydroxy-1-oxooctahydro-1H-furo[3,4-c]isobenzofuran-5-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-11-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-25 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9965(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4041(2)
_cell_length_b                   8.73516(16)
_cell_length_c                   12.8916(3)
_cell_measurement_reflns_used    4630
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3510
_cell_measurement_theta_min      5.3930
_cell_volume                     1171.43(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     36.00  95.00   0.50    0.09    --  106.80 -77.00-150.00  118
  2  \w     35.00  60.00   0.50    0.09    --  106.80 -61.00-180.00   50
  3  \w     41.00  66.00   0.50    0.09    --  106.80 -61.00-150.00   50
  4  \w     34.00  73.00   0.50    0.09    --  106.80 -61.00  30.00   78
  5  \w     38.00  63.00   0.50    0.09    --  106.80 -61.00  60.00   50
  6  \w     36.00  73.00   0.50    0.09    --  106.80 -61.00  90.00   74
  7  \w      8.00  44.00   0.50    0.05    --   47.88 -36.00  27.00   72
  8  \w     54.00  79.00   0.50    0.05    --   47.88  36.00-176.00   50
  9  \w     95.00 178.00   0.50    0.09    --  106.80  36.00-176.00  166
 10  \w    105.00 168.00   0.50    0.09    --  106.80 125.00  60.00  126
 11  \w     74.00 102.00   0.50    0.09    --  106.80 -95.00  60.00   56
 12  \w     34.00  59.00   0.50    0.09    --  106.80 -95.00  60.00   50
 13  \w    -38.00  24.00   0.50    0.05    --  -47.88  36.00-176.00  124
 14  \w    -20.00  18.00   0.50    0.05    --  -47.88  19.00-120.00   76
 15  \w    -24.00  27.00   0.50    0.05    --  -47.88  19.00 -30.00  102
 16  \w    -46.00 -21.00   0.50    0.09    --  -91.75  45.00   0.00   50
 17  \w    -54.00 -28.00   0.50    0.09    --  -91.75  61.00 -30.00   52
 18  \w    -46.00 -21.00   0.50    0.09    --  -91.75  61.00 -90.00   50
 19  \w    -63.00 -23.00   0.50    0.09    --  -91.75  61.00-120.00   80
 20  \w    -64.00 -20.00   0.50    0.09    --  -91.75  61.00-180.00   88
 21  \w    -46.00 -21.00   0.50    0.09    --  -91.75  45.00 -90.00   50
 22  \w    -46.00 -21.00   0.50    0.09    --  -91.75  45.00 120.00   50
 23  \w   -146.00-121.00   0.50    0.09    --  -91.75 -36.00  27.00   50
 24  \w   -124.00 -88.00   0.50    0.09    --  -91.75-125.00-180.00   72
 25  \w   -160.00-134.00   0.50    0.09    --  -91.75-125.00-180.00   52
 26  \w   -120.00 -36.00   0.50    0.05    --  -47.88 -36.00  27.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1133048000
_diffrn_orient_matrix_UB_12      -0.0218034000
_diffrn_orient_matrix_UB_13      0.0771598000
_diffrn_orient_matrix_UB_21      -0.0779910000
_diffrn_orient_matrix_UB_22      0.0786515000
_diffrn_orient_matrix_UB_23      0.0853718000
_diffrn_orient_matrix_UB_31      -0.0549102000
_diffrn_orient_matrix_UB_32      -0.1563249000
_diffrn_orient_matrix_UB_33      0.0322944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8054
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.686
_diffrn_reflns_theta_min         5.418
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0420P)^2^+0.6965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2071
_reflns_number_total             2336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00663e2.cif
_cod_data_source_block           20240926_nar7_5_auto
_cod_depositor_comments
'Adding full bibliography for 7160662--7160664.cif.'
_cod_database_code               7160663
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C12 H16 O6'
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.788
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C7(H7), C2(H2A)
1.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C4(H4A,H4B), C6(H6A,H6B)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              81929
_olex2_exptl_crystal_mounting_method
'on 200 micron loop in NVH oil under a cold stream of nitrogen (100 K)'
_olex2_submission_original_sample_id 20240926_NAR7_5
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.618