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_7135655
_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_formula_moiety         'C22 H16 Br Cl O3'
_chemical_formula_sum            'C22 H16 Br Cl O3'
_chemical_formula_weight         443.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-11-03
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                84.693(3)
_cell_angle_beta                 75.054(3)
_cell_angle_gamma                79.844(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6789(2)
_cell_length_b                   11.1715(5)
_cell_length_c                   12.6773(5)
_cell_measurement_reflns_used    10154
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.2120
_cell_measurement_theta_min      5.2590
_cell_volume                     898.48(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 40.53 (release 29-04-2019))'
_computing_data_reduction        'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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    -21.00  27.00   1.00    1.00    --  -42.12  38.00 -90.00   48
  2  \w     13.00 114.00   1.00    1.00    --   42.12  74.00-106.81  101
  3  \w     13.00  67.00   1.00    1.00    --   42.12  73.00-176.04   54
  4  \w    -28.00  68.00   1.00    1.00    --   42.12 -57.00 120.00   96
  5  \w    -28.00  68.00   1.00    1.00    --   42.12 -57.00 -30.00   96
  6  \w     13.00 103.00   1.00    1.00    --   42.12  70.00  -1.58   90
  7  \w     20.00  59.00   1.00    1.00    --   42.12  57.00 150.00   39
  8  \w     54.00  81.00   1.00    1.00    --   42.12-125.00-120.00   27
  9  \w     69.00  96.00   1.00    1.00    --   42.12  38.00 150.00   27
 10  \w     90.00 115.00   1.00    1.00    --   42.12  74.00  78.91   25
 11  \w     20.00  50.00   1.00    1.00    --   42.12  38.00 150.00   30
 12  \w     11.00  73.00   1.00    1.00    --   42.12  74.00  78.91   62
 13  \w     17.00  44.00   1.00    1.00    --   42.12  57.00 -30.00   27
 14  \w     78.00 146.00   1.00    3.00    --  101.13  54.00  82.37   68
 15  \w     74.00 101.00   1.00    3.00    --  101.13  62.00 -10.16   27
 16  \w     75.00 102.00   1.00    3.00    --  101.13  58.00 139.43   27
 17  \w    128.00 156.00   1.00    3.00    --  101.13  62.00-108.07   28
 18  \w     74.00 100.00   1.00    3.00    --  101.13  61.00-180.00   26
 19  \w     74.00 121.00   1.00    3.00    --  101.13  62.00-108.07   47
 20  \w     77.00 113.00   1.00    3.00    --  101.13  47.00  68.52   36
 21  \w     75.00 123.00   1.00    3.00    --  101.13  61.00 -44.00   48
 22  \w     31.00  93.00   1.00    3.00    --  101.13 -61.00 177.00   62
 23  \w     81.00 123.00   1.00    3.00    --  101.13  51.00-154.41   42
 24  \w    120.00 168.00   1.00    3.00    --  101.13  61.00 120.00   48
 25  \w     29.00 112.00   1.00    3.00    --  101.13-125.00  90.00   83
 26  \w     74.00 100.00   1.00    3.00    --  101.13  61.00  60.00   26
 27  \w     27.00 127.00   1.00    3.00    --  101.13 -77.00 -90.00  100
 28  \w     84.00 113.00   1.00    3.00    --  101.13-125.00 -60.00   29
 29  \w     74.00 100.00   1.00    3.00    --  101.13  61.00-120.00   26
 30  \w     81.00 108.00   1.00    3.00    --  101.13  61.00 150.00   27
 31  \w     75.00 108.00   1.00    3.00    --  101.13  59.00 -70.35   33
 32  \w     28.00 113.00   1.00    3.00    --  101.13-125.00-150.00   85
 33  \w    108.00 133.00   1.00    3.00    --  101.13  61.00 -30.00   25
 34  \w     77.00 170.00   1.00    3.00    --  101.13  48.00  30.60   93
 35  \w     74.00 101.00   1.00    3.00    --  101.13  61.00 -30.00   27
 36  \w    143.00 168.00   1.00    3.00    --  101.13  61.00  30.00   25
 37  \w     74.00 104.00   1.00    3.00    --  101.13  61.00 -60.00   30
 38  \w     73.00 169.00   1.00    3.00    --  101.13  65.00-151.97   96
 39  \w     74.00 101.00   1.00    3.00    --  101.13  61.00  30.00   27
 40  \w     76.00 102.00   1.00    3.00    --  101.13  61.00 120.00   26
 41  \w    144.00 170.00   1.00    3.00    --  101.13  61.00 150.00   26
 42  \w     35.00  92.00   1.00    3.00    --  101.13 -61.00  60.00   57
 43  \w     71.00 172.00   1.00    3.00    --  101.13  74.00  86.92  101
 44  \w     80.00 165.00   1.00    3.00    --  101.13  45.00   0.00   85
 45  \w     74.00 166.00   1.00    3.00    --  101.13  61.00 -90.00   92
 46  \w    136.00 170.00   1.00    3.00    --  101.13  58.00 139.43   34
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan 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      0.2068513000
_diffrn_orient_matrix_UB_12      -0.0210695000
_diffrn_orient_matrix_UB_13      0.0365106000
_diffrn_orient_matrix_UB_21      -0.0920721000
_diffrn_orient_matrix_UB_22      0.0997890000
_diffrn_orient_matrix_UB_23      0.0831505000
_diffrn_orient_matrix_UB_31      -0.0848462000
_diffrn_orient_matrix_UB_32      -0.0962985000
_diffrn_orient_matrix_UB_33      0.0872430000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.362
_diffrn_reflns_theta_min         3.613
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    4.661
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.63a (Rigaku Oxford Diffraction, 2023)
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    1.640
_exptl_crystal_description       irregular
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-heptane, dichloromethane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0190
_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^)+(0.0173P)^2^+0.5282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3332
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00474a2.cif
_cod_data_source_block           syhwlj
_cod_depositor_comments
'Adding full bibliography for 7135655--7135659.cif.'
_cod_database_code               7135655
_nottingham_internal_coll_name   SYHWLJ
_nottingham_internal_coll_number 20298
_nottingham_internal_coll_client SY/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 3.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   06/10/2025
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 07/10/2025
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 07/10/2025
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 03/11/2025
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 03/11/2025
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 03/11/2025
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H16 O3 Cl1 Br1 '
_chemical_oxdiff_usercomment
'SYHWLJ #20298 GVA-2379 SY/HWL fomblin oil on micromount'
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.561
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
;
_shelx_res_checksum              87865
_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.861