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_7135658
_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         'C17 H14 O3'
_chemical_formula_sum            'C17 H14 O3'
_chemical_formula_weight         266.28
_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             2024-05-25
_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                 96.9690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.70520(10)
_cell_length_b                   6.45340(10)
_cell_length_c                   21.6445(2)
_cell_measurement_reflns_used    14407
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.6160
_cell_measurement_theta_min      4.1020
_cell_volume                     1345.61(3)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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    -44.00  19.00   1.00    4.00    --  -41.70  57.00 150.00   63
  2  \w    -20.00  21.00   1.00    4.00    --  -41.70  38.00  90.00   41
  3  \w    -21.00  33.00   1.00    4.00    --  -41.70  38.00-120.00   54
  4  \w     16.00  42.00   1.00    4.00    --   41.70  57.00  90.00   26
  5  \w     65.00  96.00   1.00    4.00    --   41.70-125.00  30.00   31
  6  \w      8.00  40.00   1.00    4.00    --   41.70  82.00 -85.76   32
  7  \w      7.00  34.00   1.00    4.00    --   41.70  83.00-154.96   27
  8  \w     17.00 116.00   1.00    4.00    --   41.70  38.00   0.00   99
  9  \w     17.00  56.00   1.00    4.00    --   41.70 -99.00 -90.00   39
 10  \w     16.00  56.00   1.00    4.00    --   41.70  57.00-120.00   40
 11  \w     44.00 115.00   1.00    4.00    --   41.70  57.00  90.00   71
 12  \w     14.00  69.00   1.00    4.00    --   41.70  57.00-180.00   55
 13  \w     13.00  40.00   1.00    4.00    --   41.70  81.00  28.82   27
 14  \w      9.00  34.00   1.00    4.00    --   41.70  83.00  95.54   25
 15  \w     75.00 113.00   1.00    4.00    --   41.70  57.00-120.00   38
 16  \w    -32.00  62.00   1.00    4.00    --   41.70 -38.00 -60.00   94
 17  \w      7.00  33.00   1.00    4.00    --   41.70  84.00 -14.66   26
 18  \w     22.00  75.00   1.00   16.00    --  104.05 -94.00  99.12   53
 19  \w     74.00 174.00   1.00   16.00    --  104.05  69.00  60.12  100
 20  \w    125.00 157.00   1.00   16.00    --  104.05  74.00 -56.75   32
 21  \w     72.00  98.00   1.00   16.00    --  104.05  74.00 -32.58   26
 22  \w     75.00 101.00   1.00   16.00    --  104.05  61.00-150.00   26
 23  \w     32.00 112.00   1.00   16.00    --  104.05-125.00  90.00   80
 24  \w     77.00 103.00   1.00   16.00    --  104.05  50.00-168.79   26
 25  \w     75.00 103.00   1.00   16.00    --  104.05  61.00 -90.00   28
 26  \w    122.00 175.00   1.00   16.00    --  104.05  61.00 -90.00   53
 27  \w     72.00 116.00   1.00   16.00    --  104.05  74.00 -56.75   44
 28  \w     74.00 138.00   1.00   16.00    --  104.05  68.00  99.26   64
 29  \w     31.00  78.00   1.00   16.00    --  104.05-125.00  60.00   47
 30  \w     87.00 112.00   1.00   16.00    --  104.05-125.00  60.00   25
 31  \w     78.00 138.00   1.00   16.00    --  104.05  45.00-150.00   60
 32  \w     82.00 107.00   1.00   16.00    --  104.05  45.00-180.00   25
 33  \w    122.00 175.00   1.00   16.00    --  104.05  57.00 134.66   53
 34  \w     33.00 124.00   1.00   16.00    --  104.05 -77.00-120.00   91
 35  \w     79.00 104.00   1.00   16.00    --  104.05  45.00  60.00   25
 36  \w     76.00 102.00   1.00   16.00    --  104.05  57.00 134.66   26
 37  \w     72.00 144.00   1.00   16.00    --  104.05  73.00-148.26   72
 38  \w     75.00 101.00   1.00   16.00    --  104.05  61.00 150.00   26
 39  \w     75.00 111.00   1.00   16.00    --  104.05  61.00  60.00   36
 40  \w     41.00  93.00   1.00   16.00    --  104.05 -61.00  90.00   52
 41  \w     78.00 104.00   1.00   16.00    --  104.05  45.00 -90.00   26
 42  \w     75.00 101.00   1.00   16.00    --  104.05  61.00 -60.00   26
 43  \w    130.00 171.00   1.00   16.00    --  104.05  64.00  24.03   41
 44  \w     75.00 148.00   1.00   16.00    --  104.05  61.00 -30.00   73
 45  \w    145.00 172.00   1.00   16.00    --  104.05  61.00  90.00   27
 46  \w     83.00 110.00   1.00   16.00    --  104.05  45.00 -60.00   27
 47  \w     75.00 101.00   1.00   16.00    --  104.05  61.00  90.00   26
 48  \w     76.00 171.00   1.00   16.00    --  104.05  61.00-120.00   95
 49  \w     75.00 173.00   1.00   16.00    --  104.05  61.00   0.00   98
 50  \w     31.00 109.00   1.00   16.00    --  104.05-111.00-137.00   78
 51  \w     78.00 107.00   1.00   16.00    --  104.05 -94.00  99.12   29
 52  \w     74.00 101.00   1.00   16.00    --  104.05  64.00  24.03   27
 53  \w    152.00 177.00   1.00   16.00    --  104.05  68.00  99.26   25
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0128532000
_diffrn_orient_matrix_UB_12      0.2379732000
_diffrn_orient_matrix_UB_13      0.0001504000
_diffrn_orient_matrix_UB_21      -0.0134049000
_diffrn_orient_matrix_UB_22      0.0035163000
_diffrn_orient_matrix_UB_23      0.0701582000
_diffrn_orient_matrix_UB_31      0.1588724000
_diffrn_orient_matrix_UB_32      -0.0191341000
_diffrn_orient_matrix_UB_33      0.0146775000
_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  0.0211
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20447
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.820
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.711
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane, dichloromethane'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0322P)^2^+0.2081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0635
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5122
_reflns_number_total             5250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00474a2.cif
_cod_data_source_block           syhwlb
_cod_depositor_comments
'Adding full bibliography for 7135655--7135659.cif.'
_cod_database_code               7135658
_nottingham_internal_coll_name   SYHWLB
_nottingham_internal_coll_number 19766
_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   09/05/2024
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 16/05/2024
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 16/05/2024
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 16/05/2024
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_validation_date 26/05/2024
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 26/05/2024
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C17H14O3
_chemical_oxdiff_usercomment
'SYHWLB #19766 GVB-1999 SY/HWL fomblin oil on micromount'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.833
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4B(H4B), C4A(H4A), C9A(H9A), C6A(H6A), C9B(H9B), C7B(H7B), C3B(H3B),
 C3A(H3A), C7A(H7A), C6B(H6B)
2.b Secondary CH2 refined with riding coordinates:
 C10B(H10A,H10B), C10A(H10C,H10D), C11A(H11C,H11D), C11B(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C17B(H17B), C16B(H16B), C13A(H13A), C13B(H13B), C15B(H15B), C17A(H17A),
 C14B(H14B), C14A(H14A), C15A(H15A), C16A(H16A)
;
_shelx_res_checksum              1623
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.198
_oxdiff_exptl_absorpt_empirical_full_min 0.817