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_7160662
_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 O7'
_chemical_formula_sum            'C12 H16 O7'
_chemical_formula_weight         272.25
_chemical_name_systematic
'(+-)-methyl (3aR,6R,6aS,10aS)-3a-hydroxy-1-oxooctahydro-1H-benzo[d]furo[3,4-c][1,2]dioxine-6-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-21
_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                 100.9550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8697(2)
_cell_length_b                   8.42300(10)
_cell_length_c                   22.9132(3)
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0560
_cell_measurement_theta_min      3.9210
_cell_volume                     2438.56(6)
_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    'SHELXT  (Sheldrick, 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 0.999
_diffrn_measured_fraction_theta_max 0.919
_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    -87.00 -43.00   0.50    0.05    --  -91.75  77.00 150.00   88
  2  \w    -62.00 -21.00   0.50    0.05    --  -91.75  61.00 120.00   82
  3  \w    -46.00 -21.00   0.50    0.05    --  -91.75  45.00 120.00   50
  4  \w    -64.00 -26.00   0.50    0.05    --  -91.75  61.00  90.00   76
  5  \w    -46.00 -21.00   0.50    0.05    --  -91.75  45.00  60.00   50
  6  \w    -46.00 -21.00   0.50    0.05    --  -91.75  45.00  90.00   50
  7  \w    -45.00 -20.00   0.50    0.05    --  -91.75  45.00   0.00   50
  8  \w    -49.00 -19.00   0.50    0.05    --  -91.75  61.00 -30.00   60
  9  \w    -46.00 -21.00   0.50    0.05    --  -91.75  45.00 -30.00   50
 10  \w    -46.00 -20.00   0.50    0.05    --  -91.75  45.00-180.00   52
 11  \w    -71.00 -24.00   0.50    0.05    --  -91.75 125.00-180.00   94
 12  \w    -78.00 -43.00   0.50    0.05    --  -48.13  94.00 148.00   70
 13  \w    -74.00 -48.00   0.50    0.05    --  -91.75  94.00 148.00   52
 14  \w    -17.00   9.00   0.50    0.05    --  -48.13  94.00 148.00   52
 15  \w    -29.00  27.00   0.50    0.05    --  -48.13  19.00 -90.00  112
 16  \w    -40.00  23.00   0.50    0.05    --  -48.13  38.00-150.00  126
 17  \w     12.00  42.00   0.50    0.05    --   48.13 -94.00  37.00   60
 18  \w     57.00 106.00   0.50    0.05    --  106.80 -94.00  37.00   98
 19  \w   -154.00-100.00   0.50    0.05    --  -91.75 -94.00  37.00  108
 20  \w   -118.00 -75.00   0.50    0.05    --  -48.13-125.00-180.00   86
 21  \w     42.00  68.00   0.50    0.05    --  106.80 -61.00-180.00   52
 22  \w     49.00  75.00   0.50    0.05    --  106.80 -61.00-150.00   52
 23  \w     42.00  68.00   0.50    0.05    --  106.80 -61.00-120.00   52
 24  \w     38.00  67.00   0.50    0.05    --  106.80 -61.00 -90.00   58
 25  \w     40.00  65.00   0.50    0.05    --  106.80 -61.00  90.00   50
 26  \w    117.00 168.00   0.50    0.05    --  106.80  94.00 148.00  102
;
_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      0.0259032000
_diffrn_orient_matrix_UB_12      -0.0082912000
_diffrn_orient_matrix_UB_13      0.0684058000
_diffrn_orient_matrix_UB_21      -0.0436040000
_diffrn_orient_matrix_UB_22      0.1693627000
_diffrn_orient_matrix_UB_23      0.0034452000
_diffrn_orient_matrix_UB_31      -0.1108566000
_diffrn_orient_matrix_UB_32      -0.0685444000
_diffrn_orient_matrix_UB_33      0.0003232000
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.716
_diffrn_reflns_theta_min         3.930
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67208
_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    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_preparation
'tetronate was dissolved in chloroform and stirred for six days at room temperature. Product ran through column for purifcation'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00063(7)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.9727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0781
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2168
_reflns_number_total             2364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00663e2.cif
_cod_data_source_block           20240904_nar6_1_auto
_cod_depositor_comments
'Adding full bibliography for 7160662--7160664.cif.'
_cod_database_code               7160662
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C12 H16 O5'
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.776
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C5(H5A,H5B), C10(H10A,H10B), C9(H9A,H9B)
1.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
1.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_shelx_res_checksum              43583
_olex2_exptl_crystal_mounting_method 'in NVH oil on 200 micron nylon loop'
_olex2_submission_original_sample_id 20240904_NAR6_1
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.734