Cycloaddition of Benzo[d]thiazoles with Imidazol-4-one Activated Donor-Acceptor Cyclopropanes. Synthesis of Spirocyclic Inhibitors of HIV-1
Ikonnikova, Viktoria A.; Shchigal, Olga; Anisenko, Andrey; Solyev, Pavel N.; Krylkov, Grigory A.; Romanenko, Alexander R.; Korlyukov, Alexander; Baranov, Mikhail S.; Gottikh, Marina; Mikhaylov, Andrey A.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00180G

data_7161091
_publ_section_title
;
 Cycloaddition of benzo[<i>d</i>]thiazoles with imidazol-4-one-activated
 donor-acceptor cyclopropanes: synthesis of spirocyclic inhibitors of
 HIV-1.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3232
_journal_page_last               3238
_journal_paper_doi               10.1039/d6ob00180g
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C22 H20 F3 N3 O2 S'
_chemical_formula_sum            'C22 H20 F3 N3 O2 S'
_chemical_formula_weight         447.47
_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
_audit_creation_date             2026-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-12 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                84.009(3)
_cell_angle_beta                 86.084(3)
_cell_angle_gamma                72.303(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4518(7)
_cell_length_b                   10.5180(10)
_cell_length_c                   13.4176(13)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.403
_cell_measurement_theta_min      2.439
_cell_volume                     995.66(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14170
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_min         2.040
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.9326.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         6026
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3740
_reflns_number_total             6026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00180g2.cif
_cod_data_source_block           iv1098_1_0m
_cod_depositor_comments          'Adding full bibliography for 7161091.cif.'
_cod_database_code               7161091
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-C15A \\sim O1B-C15B
 with sigma of 0.02
 N2A-C9 \\sim N2B-C9
 with sigma of 0.02
 N2A-C12A \\sim N2B-C12B
 with sigma of 0.02
 N3A-C12A \\sim N3B-C12B
 with sigma of 0.02
 N3A-C14A \\sim N3B-C14B
 with sigma of 0.02
 N3A-C15A \\sim N3B-C15B
 with sigma of 0.02
 C9-C15A \\sim C9-C15B
 with sigma of 0.02
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.02
 O1A-N3A \\sim O1B-N3B
 with sigma of 0.04
 O1A-C9 \\sim O1B-C9
 with sigma of 0.04
 N2A-N3A \\sim N2B-N3B
 with sigma of 0.04
 N2A-C13A \\sim N2B-C13B
 with sigma of 0.04
 N3A-C9 \\sim N3B-C9
 with sigma of 0.04
 N3A-C13A \\sim N3B-C13B
 with sigma of 0.04
 C9-C12A \\sim C9-C12B
 with sigma of 0.04
 C12A-C14A \\sim C12B-C14B
 with sigma of 0.04
 C12A-C15A \\sim C12B-C15B
 with sigma of 0.04
 C14A-C15A \\sim C14B-C15B
 with sigma of 0.04
3. Restrained planarity
 C9, O1B, N2B, N3B, C12B, C13B, C14B, C15B
 with sigma of 0.1
 C9, O1A, N2A, N3A, C12A, C13A, C14A, C15A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(N3B) = Uanis(C12A)
Uanis(C13A) = Uanis(C14B)
Uanis(C14A) = Uanis(C13B)
Uanis(N3A) = Uanis(C12B)
Uanis(N2B) = Uanis(C15A)
Uanis(C15B) = Uanis(N2A)
Uanis(O1A) = Uanis(O1B)
5. Others
 Fixed Sof: O1A(0.95) N2A(0.95) N3A(0.95) C12A(0.95) C13A(0.95) H13A(0.95)
 H13B(0.95) H13C(0.95) C14A(0.95) H14A(0.95) H14B(0.95) H14C(0.95) C15A(0.95)
 O1B(0.05) N2B(0.05) N3B(0.05) C12B(0.05) C13B(0.05) H13D(0.05) H13E(0.05)
 H13F(0.05) C14B(0.05) H14D(0.05) H14E(0.05) H14F(0.05) C15B(0.05)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21)
6.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C13B(H13D,
 H13E,H13F), C14B(H14D,H14E,H14F)
;
_shelx_res_checksum              59914
_olex2_submission_special_instructions 'No special instructions were received'