Concise synthesis of triasteranones from barbaralones.
Yeung, Serena; Allen, Emily G.; Jones, Kieran D.; Argent, Stephen P.; Lam, Hon Wai; Chemical communications (Cambridge, England)  (2026) –; doi:10.1039/d6cc00474a

data_7135656
_publ_section_title
;
 Concise synthesis of triasteranones from barbaralones.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7348
_journal_page_last               7352
_journal_paper_doi               10.1039/d6cc00474a
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H10 O3'
_chemical_formula_sum            'C15 H10 O3'
_chemical_formula_weight         238.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.42140(10)
_cell_length_b                   10.2233(2)
_cell_length_c                   8.6908(2)
_cell_measurement_reflns_used    4997
_cell_measurement_temperature    120.0(3)
_cell_measurement_theta_max      72.5340
_cell_measurement_theta_min      5.2160
_cell_volume                     555.656(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120.0(3)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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      2.00  29.00   1.00    4.00    --  -41.82  19.00 120.00   27
  2  \w    -44.00  26.00   1.00    4.00    --  -41.82  57.00  30.00   70
  3  \w     -4.00  37.00   1.00    4.00    --  -41.82  19.00 -30.00   41
  4  \w    -98.00 -11.00   1.00    4.00    --  -41.82 125.00 150.00   87
  5  \w      8.00  33.00   1.00    4.00    --   41.82  82.00  70.83   25
  6  \w     15.00  41.00   1.00    4.00    --   41.82  57.00 150.00   26
  7  \w      8.00  41.00   1.00    4.00    --   41.82  81.00 175.75   33
  8  \w     66.00  93.00   1.00    4.00    --   41.82  57.00 150.00   27
  9  \w     15.00  41.00   1.00    4.00    --   41.82  57.00-120.00   26
 10  \w     -4.00  24.00   1.00    4.00    --   41.82 -19.00-150.00   28
 11  \w      9.00  38.00   1.00    4.00    --   41.82  80.00 -98.93   29
 12  \w     26.00 111.00   1.00    4.00    --   41.82  38.00 -30.00   85
 13  \w      7.00  32.00   1.00    4.00    --   41.82  84.00 -31.15   25
 14  \w     55.00 107.00   1.00    4.00    --   41.82  57.00-120.00   52
 15  \w     61.00 105.00   1.00    4.00    --   41.82  57.00  30.00   44
 16  \w     29.00  62.00   1.00    4.00    --   41.82  38.00 120.00   33
 17  \w     20.00  60.00   1.00    4.00    --   41.82  57.00  30.00   40
 18  \w     77.00 145.00   1.00   16.00    --  104.05  61.00-150.00   68
 19  \w     21.00  93.00   1.00   16.00    --  104.05 -94.00  30.00   72
 20  \w    135.00 162.00   1.00   16.00    --  104.05  60.00 -33.99   27
 21  \w     76.00 110.00   1.00   16.00    --  104.05  61.00 -60.00   34
 22  \w    114.00 173.00   1.00   16.00    --  104.05  61.00-180.00   59
 23  \w     76.00 102.00   1.00   16.00    --  104.05  61.00-180.00   26
 24  \w     75.00 101.00   1.00   16.00    --  104.05  60.00 -33.99   26
 25  \w     75.00 175.00   1.00   16.00    --  104.05  61.00-120.00  100
 26  \w    134.00 172.00   1.00   16.00    --  104.05  61.00 -60.00   38
 27  \w     75.00 112.00   1.00   16.00    --  104.05  61.00  90.00   37
 28  \w    132.00 158.00   1.00   16.00    --  104.05  61.00  90.00   26
 29  \w     80.00 105.00   1.00   16.00    --  104.05  45.00   0.00   25
 30  \w     82.00 109.00   1.00   16.00    --  104.05  45.00 120.00   27
 31  \w     38.00  92.00   1.00   16.00    --  104.05 -61.00 120.00   54
 32  \w     77.00 173.00   1.00   16.00    --  104.05  61.00 120.00   96
 33  \w    133.00 174.00   1.00   16.00    --  104.05  61.00  60.00   41
 34  \w     34.00 111.00   1.00   16.00    --  104.05-125.00 -90.00   77
 35  \w     80.00 131.00   1.00   16.00    --  104.05  38.00 169.37   51
 36  \w     75.00 104.00   1.00   16.00    --  104.05  61.00  60.00   29
 37  \w     75.00 106.00   1.00   16.00    --  104.05  61.00   0.00   31
 38  \w     32.00  57.00   1.00   16.00    --  104.05 -30.00 150.00   25
 39  \w     41.00 111.00   1.00   16.00    --  104.05-125.00   0.00   70
 40  \w     24.00 105.00   1.00   16.00    --  104.05 -94.00  90.00   81
 41  \w     79.00 104.00   1.00   16.00    --  104.05  45.00-180.00   25
 42  \w     80.00 107.00   1.00   16.00    --  104.05  45.00-150.00   27
 43  \w    132.00 174.00   1.00   16.00    --  104.05  61.00 -90.00   42
 44  \w     75.00 174.00   1.00   16.00    --  104.05  61.00  30.00   99
 45  \w     42.00  72.00   1.00   16.00    --  104.05 -61.00-120.00   30
 46  \w     75.00 103.00   1.00   16.00    --  104.05  61.00 -90.00   28
 47  \w     77.00 126.00   1.00   16.00    --  104.05  59.00  12.91   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.778
_diffrn_reflns_theta_min         5.226
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-pentane, dichloromethane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0389P)^2^+0.1102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2120
_reflns_number_total             2165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00474a2.cif
_cod_data_source_block           syhwla
_cod_depositor_comments
'Adding full bibliography for 7135655--7135659.cif.'
_cod_database_code               7135656
_nottingham_internal_coll_name   SYHWLA
_nottingham_internal_coll_number 19747
_nottingham_internal_coll_client SY/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '16.00, 4.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczkj1
_nottingham_internal_coll_date   12/04/2024
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 15/04/2024
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 15/04/2024
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 15/04/2024
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_validation_date 16/04/2024
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 16/04/2024
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.860
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_shelx_res_checksum              15759
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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
;