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_7135659
_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         'C13 H6 Br2 O3 S'
_chemical_formula_sum            'C13 H6 Br2 O3 S'
_chemical_formula_weight         402.064
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-12-09
_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                90
_cell_angle_beta                 100.104(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6081(8)
_cell_length_b                   13.0496(6)
_cell_length_c                   6.7220(3)
_cell_measurement_reflns_used    6282
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2110
_cell_measurement_theta_min      2.9970
_cell_volume                     1261.54(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_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  'olex2.refine 1.5 (Bourhis et al., 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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9771
_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    -31.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  124
  2  \w     89.00 169.00   0.50    1.00    --   97.40  82.00-118.00  160
  3  \w     60.00 130.00   0.50    1.00    --   97.40 -82.00 120.00  140
  4  \w    -29.00  24.00   0.50    0.50    --    0.00 -82.00   0.00  106
  5  \w    -21.00  26.00   0.50    0.50    --    0.00 -82.00 -60.00   94
  6  \w    -31.00  29.00   0.50    0.50    --    0.00 -82.00  60.00  120
  7  \w    -31.00  27.00   0.50    0.50    --    0.00 -82.00-120.00  116
  8  \w    -26.00   2.00   0.50    0.50    --    0.00 -82.00-180.00   56
  9  \w     74.00 171.00   0.50    1.00    --   97.40  30.00-150.00  194
 10  \w     34.00 130.00   0.50    1.00    --   97.40 -82.00 -90.00  192
 11  \w     75.00 165.00   0.50    1.00    --   97.40  45.00  90.00  180
 12  \w     10.00  39.00   0.50    1.00    --   97.40 -61.00 120.00   58
 13  \w     90.00 117.00   0.50    1.00    --   97.40 -82.00  30.00   54
 14  \w     71.00 120.00   0.50    1.00    --   97.40 -61.00 120.00   98
 15  \w     81.00 130.00   0.50    1.00    --   97.40 -82.00 -30.00   98
 16  \w      9.00 119.00   0.50    1.00    --   97.40 -30.00 -90.00  220
 17  \w     14.00  66.00   0.50    1.00    --   97.40 -82.00 -30.00  104
 18  \w    101.00 131.00   0.50    1.00    --   97.40 -82.00   0.00   60
 19  \w     37.00  74.00   0.50    1.00    --   97.40 -82.00   0.00   74
 20  \w     20.00  75.00   0.50    1.00    --   97.40 -45.00 150.00  110
 21  \w     96.00 121.00   0.50    1.00    --   97.40 -82.00 150.00   50
 22  \w      9.00 124.00   0.50    1.00    --   97.40 -61.00  60.00  230
 23  \w     93.00 187.00   0.50    1.00    --   97.40  82.00-180.00  188
 24  \w    137.00 162.00   0.50    1.00    --   97.40  82.00-150.00   50
 25  \w     93.00 138.00   0.50    1.00    --   97.40  82.00 120.00   90
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_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      -0.0929960000
_diffrn_orient_matrix_UB_12      -0.0060154000
_diffrn_orient_matrix_UB_13      -0.1484412000
_diffrn_orient_matrix_UB_21      -0.0022811000
_diffrn_orient_matrix_UB_22      -0.1168645000
_diffrn_orient_matrix_UB_23      0.0310081000
_diffrn_orient_matrix_UB_31      -0.0531308000
_diffrn_orient_matrix_UB_32      0.0155618000
_diffrn_orient_matrix_UB_33      0.1765695000
_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  0.0625
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9771
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12011
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9771
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.52
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_exptl_absorpt_coefficient_mu    9.726
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.450
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_description       block
_exptl_crystal_F_000             773.821
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-heptane, dichloromethane'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.2363
_refine_diff_density_min         -0.9500
_refine_diff_density_rms         0.1803
_refine_ls_d_res_high            0.7962
_refine_ls_d_res_low             14.3815
_refine_ls_goodness_of_fit_ref   1.0515
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0515
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+4.8152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2265
_reflns_number_total             2563
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d6cc00474a2.cif
_cod_data_source_block           SYHWLF
_cod_depositor_comments
'Adding full bibliography for 7135655--7135659.cif.'
_cod_database_code               7135659
_nottingham_internal_coll_name   SYHWLF
_nottingham_internal_coll_number 19970
_nottingham_internal_coll_client SY/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '0.50, 1.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczkj1
_nottingham_internal_coll_date   06/12/2024
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 07/02/2025
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 07/02/2025
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 07/02/2025
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_validation_date 09/12/2025
_nottingham_internal_validation_user pczspa
_chemical_oxdiff_formula         C13H6Br2O3S
_chemical_oxdiff_usercomment
'SYHWLF #19970 MM-1132 SY/HWL Fomblin Micromount'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.701