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_7160664
_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         'C10 H14 O5'
_chemical_formula_sum            'C10 H14 O5'
_chemical_formula_weight         214.21
_chemical_name_systematic
(3aR,6aS,10aS)-3a-hydroxyoctahydro-1H-benzo[d]furo[3,4-c][1,2]dioxin-1-one
_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     dual
_audit_creation_date             2025-07-28
_audit_creation_method
;
Olex2 1.5-ac6-015
(compiled 2023.12.04 svn.r209d9fb2 for Rigaku Oxford Diffraction, GUI svn.r6873)
;
_audit_update_record
;
2025-07-28 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.398(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9717(4)
_cell_length_b                   8.9531(3)
_cell_length_c                   11.4158(4)
_cell_measurement_reflns_used    4695
_cell_measurement_temperature    120.3(4)
_cell_measurement_theta_max      80.0400
_cell_measurement_theta_min      5.1550
_cell_volume                     972.55(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-ac6-015 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-015 (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      120.3(4)
_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 0.992
_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    -99.00 -22.00   0.50    0.18    --  -38.28 142.00 160.00  154
  2  \w   -123.00 -63.00   0.50    0.18    --  -38.28-142.00 103.00  120
  3  \w   -122.00 -72.00   0.50    0.18    --  -38.28-129.00 -84.00  100
  4  \w     44.00 120.00   0.50    0.18    --   38.28-142.00 103.00  152
  5  \w   -165.00 -71.00   0.50    0.70    --  -84.64-129.00 -84.00  188
  6  \w    -98.00 -22.00   0.50    0.70    --  -84.64 142.00 160.00  152
  7  \w   -155.00 -62.00   0.50    0.70    --  -84.64-142.00 103.00  186
  8  \w     44.00 124.00   0.50    0.70    --   84.64-142.00 103.00  160
  9  \w     37.00 114.00   0.50    0.70    --   84.64-129.00 -84.00  154
 10  \w    -98.00 -23.00   0.50    0.70    -- -106.00 142.00 160.00  150
 11  \w     46.00 115.00   0.50    0.70    --  131.00-129.00 -84.00  138
 12  \w     45.00 125.00   0.50    0.70    --  131.00-142.00 103.00  160
 13  \w     84.00 172.00   0.50    0.70    --  131.00 142.00 160.00  176
 14  \w    -31.00  44.00   0.50    0.18    --  -38.28  19.00-180.00  150
 15  \w    -31.00  44.00   0.50    0.18    --  -38.28  19.00 -60.00  150
 16  \w   -132.00 -86.00   0.50    0.18    --  -38.28 -99.00 120.00   92
 17  \w    -31.00  44.00   0.50    0.18    --  -38.28  19.00-180.00  150
 18  \w   -177.00-145.00   0.50    0.70    --  -84.64  15.00-180.00   64
 19  \w   -177.00-145.00   0.50    0.70    --  -84.64  15.00-150.00   64
 20  \w    -46.00  -2.00   0.50    0.70    --  -84.64  45.00   0.00   88
 21  \w   -177.00-145.00   0.50    0.70    --  -84.64  15.00 -30.00   64
 22  \w     -8.00  47.00   0.50    0.70    --   84.64 -30.00  60.00  110
 23  \w     -8.00  47.00   0.50    0.70    --   84.64 -30.00 150.00  110
 24  \w    103.00 163.00   0.50    0.70    --   84.64 111.00 -90.00  120
 25  \w    -81.00 -25.00   0.50    0.70    -- -106.00 104.00 -30.00  112
 26  \w    -51.00 -23.00   0.50    0.70    -- -106.00  50.00 -60.00   56
 27  \w    -51.00 -23.00   0.50    0.70    -- -106.00  50.00 -30.00   56
 28  \w    -51.00 -23.00   0.50    0.70    -- -106.00  50.00  30.00   56
 29  \w    106.00 178.00   0.50    0.70    --  131.00 104.00 -30.00  144
 30  \w     43.00  80.00   0.50    0.70    --  131.00 -64.00 -30.00   74
 31  \w     38.00 107.00   0.50    0.70    --  131.00-104.00  90.00  138
 32  \w     43.00  80.00   0.50    0.70    --  131.00 -64.00  30.00   74
 33  \w     89.00 178.00   0.50    0.70    --  131.00  64.00-180.00  178
 34  \w     38.00 107.00   0.50    0.70    --  131.00-104.00  90.00  138
 35  \w     38.00 107.00   0.50    0.70    --  131.00-104.00 120.00  138
 36  \w    151.00 178.00   0.50    0.70    --  131.00 -12.00  90.00   54
 37  \w    151.00 178.00   0.50    0.70    --  131.00 -12.00-180.00   54
 38  \w     34.00 106.00   0.50    0.70    --  131.00 -92.00 150.00  144
 39  \w     89.00 178.00   0.50    0.70    --  131.00  64.00  90.00  178
 40  \w     38.00 107.00   0.50    0.70    --  131.00-104.00 150.00  138
 41  \w     35.00 101.00   0.50    0.70    --  131.00 -77.00 -30.00  132
 42  \w    151.00 178.00   0.50    0.70    --  131.00 -12.00 120.00   54
 43  \w     38.00 107.00   0.50    0.70    --  131.00-104.00 -90.00  138
 44  \w     89.00 178.00   0.50    0.70    --  131.00  64.00  90.00  178
 45  \w     83.00 178.00   0.50    0.70    --  131.00  50.00-150.00  190
 46  \w     34.00 106.00   0.50    0.70    --  131.00 -92.00 120.00  144
 47  \w     35.00 101.00   0.50    0.70    --  131.00 -77.00 120.00  132
 48  \w     35.00 101.00   0.50    0.70    --  131.00 -77.00 150.00  132
 49  \w     38.00 107.00   0.50    0.70    --  131.00-104.00-120.00  138
 50  \w    106.00 178.00   0.50    0.70    --  131.00 104.00  60.00  144
 51  \w     89.00 178.00   0.50    0.70    --  131.00  64.00 120.00  178
 52  \w     43.00  80.00   0.50    0.70    --  131.00 -64.00 150.00   74
 53  \w   -128.00  33.00   0.50    0.18    --  -38.28 -38.00 150.00  322
 54  \w    -21.00  18.00   0.50    0.18    --   38.28 101.00  67.87   78
;
_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      0.0766415000
_diffrn_orient_matrix_UB_12      0.1149459000
_diffrn_orient_matrix_UB_13      -0.0574167000
_diffrn_orient_matrix_UB_21      0.0757671000
_diffrn_orient_matrix_UB_22      -0.1279507000
_diffrn_orient_matrix_UB_23      -0.0448878000
_diffrn_orient_matrix_UB_31      -0.1206691000
_diffrn_orient_matrix_UB_32      -0.0071094000
_diffrn_orient_matrix_UB_33      -0.1211896000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.946
_diffrn_reflns_theta_min         5.177
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85943
_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 - Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   -
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_preparation
'Stirring 3-(hex-5-en-1-yl)-4-hydroxyfuran-2(5H)-one in dichloromethane at room temperature for 6 days'
_exptl_crystal_recrystallization_method
'Vapour diffusion of hexane into a DCM solution'
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0792P)^2^+0.6295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1795
_reflns_number_total             2102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00663e2.cif
_cod_data_source_block           20250701_nar9_1_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_colour_lustre' value 'Clear' was changed to
'clear' 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 7160662--7160664.cif.
;
_cod_database_code               7160664
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.622
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C3(H3A,H3B), C7(H7A,H7B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_date_sample_data_collection 2025-07-01
_olex2_exptl_crystal_mounting_method
'in NVH oil on a nylon loop under a nitrogen cold stream'
_olex2_submission_original_sample_id 20250701_NAR9_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 3.072
_oxdiff_exptl_absorpt_empirical_full_min 0.657