Synthesis and biological study of benzothiophene-fused azaenediyne hybrids as potential anticancer agents.
Khmelevskaya, Ekaterina A.; Danilkina, Natalia A.; Silonov, Sergey A.; Tretyakov, Evgeny V.; Khlebnikov, Alexander F.; Melnikov, Vladimir E.; Nikitina, Anastasiia V.; Rumyantsev, Andrey M.; Kryukova, Mariya A.; Balova, Irina A.; Organic & biomolecular chemistry 24 (2026) 617–629; doi:10.1039/d5ob01600b

data_7161038
_publ_section_title
;
 Synthesis and biological study of benzothiophene-fused azaenediyne
 hybrids as potential anticancer agents.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              617
_journal_page_last               629
_journal_paper_doi               10.1039/d5ob01600b
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C22 H19 N O2 S2'
_chemical_formula_sum            'C22 H19 N O2 S2'
_chemical_formula_weight         393.50
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-07-25 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4398(2)
_cell_length_b                   8.10650(10)
_cell_length_c                   12.09810(10)
_cell_measurement_reflns_used    7238
_cell_measurement_temperature    100.00(14)
_cell_measurement_theta_max      70.2810
_cell_measurement_theta_min      2.3770
_cell_volume                     1806.60(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      N~2~
_diffrn_ambient_temperature      100.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -58.00  -6.00   0.50    0.20    --  -38.95 111.00 -70.00  104
  2  \w     -1.00  59.00   0.50    0.20    --   38.95-111.00-164.00  120
  3  \w    101.00 127.00   0.50    0.60    --  100.00 111.00 -70.00   52
  4  \w     31.00  73.00   0.50    0.60    --  100.00-111.00-164.00   84
  5  \w    -63.00 -22.00   0.50    0.20    --  -38.95 -21.00 -30.00   82
  6  \w   -107.00 -72.00   0.50    0.20    --  -38.95 -21.00 -30.00   70
  7  \w    -67.00 -25.00   0.50    0.20    --  -38.95 -32.00-150.00   84
  8  \w   -107.00 -72.00   0.50    0.20    --  -38.95 -32.00-150.00   70
  9  \w      6.00  51.00   0.50    0.20    --   38.95 -43.00-120.00   90
 10  \w     71.00 105.00   0.50    0.20    --   38.95  43.00 120.00   68
 11  \w    -23.00   9.00   0.50    0.20    --   38.95 -43.00-180.00   64
 12  \w     27.00  59.00   0.50    0.20    --   38.95  43.00 120.00   64
 13  \w     72.00 101.00   0.50    0.20    --   38.95  54.00 150.00   58
 14  \w     26.00  56.00   0.50    0.20    --   38.95 -43.00-180.00   60
 15  \w     18.00  43.00   0.50    0.20    --   38.95-138.00-180.00   50
 16  \w     82.00 107.00   0.50    0.20    --   38.95  32.00-120.00   50
 17  \w     25.00  51.00   0.50    0.20    --   38.95  54.00 150.00   52
 18  \w     50.00  95.00   0.50    0.20    --   38.95-138.00-180.00   90
 19  \w     60.00  86.00   0.50    0.20    --   38.95-138.00 -30.00   52
 20  \w     83.00 146.00   0.50    0.60    --  100.00  45.00 -30.00  126
 21  \w     68.00 106.00   0.50    0.60    --  100.00-111.00 150.00   76
 22  \w     31.00 107.00   0.50    0.60    --  100.00-111.00-180.00  152
 23  \w     83.00 133.00   0.50    0.60    --  100.00  45.00 120.00  100
 24  \w     67.00 128.00   0.50    0.60    --  100.00 -86.00-150.00  122
 25  \w     27.00 105.00   0.50    0.60    --  100.00 -93.00   0.00  156
 26  \w     93.00 118.00   0.50    0.60    --  100.00-133.00 -60.00   50
 27  \w    129.00 155.00   0.50    0.60    --  100.00  45.00 -60.00   52
 28  \w     88.00 121.00   0.50    0.60    --  100.00  45.00 -60.00   66
 29  \w     82.00 109.00   0.50    0.60    --  100.00  61.00-150.00   54
 30  \w    116.00 156.00   0.50    0.60    --  100.00  61.00-150.00   80
 31  \w     39.00  64.00   0.50    0.60    --  100.00 -86.00-150.00   50
 32  \w    108.00 133.00   0.50    0.60    --  100.00  30.00-180.00   50
 33  \w     79.00 105.00   0.50    0.60    --  100.00 -37.00 -60.00   52
 34  \w     38.00  70.00   0.50    0.60    --  100.00 -93.00 120.00   64
 35  \w     92.00 125.00   0.50    0.60    --  100.00 -69.00-150.00   66
 36  \w    117.00 155.00   0.50    0.60    --  100.00  53.00-120.00   76
 37  \w     37.00  72.00   0.50    0.60    --  100.00 -69.00-150.00   70
 38  \w     82.00 110.00   0.50    0.60    --  100.00 -77.00-180.00   56
 39  \w     83.00 151.00   0.50    0.60    --  100.00  77.00 -30.00  136
 40  \w     83.00 109.00   0.50    0.60    --  100.00  77.00-120.00   52
 41  \w    112.00 156.00   0.50    0.60    --  100.00  53.00  90.00   88
 42  \w     35.00 114.00   0.50    0.60    --  100.00 -30.00 150.00  158
 43  \w     95.00 121.00   0.50    0.60    --  100.00 111.00 -70.00   52
 44  \w    -56.00 -30.00   0.50    0.20    --  -38.95  21.00-180.00   52
 45  \w    -47.00 -17.00   0.50    0.20    --  -38.95  32.00-180.00   60
 46  \w    -21.00  27.00   0.50    0.20    --  -38.95  43.00  30.00   96
 47  \w    -14.00  11.00   0.50    0.20    --  -38.95  21.00-180.00   50
 48  \w     28.00  56.00   0.50    0.20    --   38.95 -43.00 150.00   56
 49  \w     19.00  45.00   0.50    0.20    --   38.95  65.00 -90.00   52
 50  \w    -18.00   8.00   0.50    0.20    --   38.95 -89.00-180.00   52
 51  \w     77.00 103.00   0.50    0.20    --   38.95  65.00 -90.00   52
 52  \w     71.00 103.00   0.50    0.20    --   38.95  43.00  60.00   64
 53  \w     36.00  62.00   0.50    0.20    --   38.95  43.00  60.00   52
 54  \w     44.00  70.00   0.50    0.20    --   38.95 -89.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0731437000
_diffrn_orient_matrix_UB_12      0.0856727000
_diffrn_orient_matrix_UB_13      0.0276008000
_diffrn_orient_matrix_UB_21      -0.0322328000
_diffrn_orient_matrix_UB_22      0.1651891000
_diffrn_orient_matrix_UB_23      -0.0416791000
_diffrn_orient_matrix_UB_31      -0.0245572000
_diffrn_orient_matrix_UB_32      0.0385148000
_diffrn_orient_matrix_UB_33      0.1172901000
_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  0.0420
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11596
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.434
_diffrn_reflns_theta_min         2.399
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0489P)^2^+0.8527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3181
_reflns_number_total             3450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01600b2.cif
_cod_data_source_block           15436_dna-bc-nts
_cod_database_code               7161038
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H19 N1 O2 S2'
_shelx_estimated_absorpt_t_max   100.00
_shelx_estimated_absorpt_t_min   100.00
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
1.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C5(H5), C21(H21), C17(H17), C18(H18), C20(H20), C10(H10),
 C9(H9), C11(H11)
1.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              27422
_shelx_hkl_checksum              94486
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.846