Synthesis of functionalized thiazoloindole-3-thiones and their spirocongeners from 2-acylethynyl-4,5,6,7-tetrahydroindoles and carbon disulfide
Tomilin, Denis N.; Stepanova, Sophia A.; Borodina, Tatyana N.; Ushakov, Igor A.; Trofimov, Boris A.; New Journal of Chemistry 49 (2025) 16820–16827; doi:10.1039/D5NJ02380G

data_7063969
_publ_section_title
;
 Synthesis of functionalized thiazoloindole-3-thiones and their
 spirocongeners from 2-acylethynyl-4,5,6,7-tetrahydroindoles and carbon
 disulfide
;
_journal_issue                   38
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16820
_journal_page_last               16827
_journal_paper_doi               10.1039/D5NJ02380G
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C31 H20 N2 O2 S2'
_chemical_formula_sum            'C31 H20 N2 O2 S2'
_chemical_formula_weight         516.61
_chemical_melting_point          272.15
_chemical_name_systematic
(2Z,2'Z)-2,2'-(1H,1'H-spiro[pyrrolo[1,2-c]thiazole-3,3'-thiazolo[3,4-a]indole]-1,1'-diylidene)bis(1-phenylethan-1-one)
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-20 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                111.013(2)
_cell_angle_beta                 91.816(2)
_cell_angle_gamma                109.590(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8390(4)
_cell_length_b                   10.9281(5)
_cell_length_c                   13.4307(6)
_cell_measurement_reflns_used    8546
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      61.19
_cell_measurement_theta_min      3.58
_cell_volume                     1250.93(10)
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.851
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.851
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15798
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         61.222
_diffrn_reflns_theta_min         3.579
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.4905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.6475.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       rhombohedron
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexan: Dichlormetan (1: 1)'
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_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     334
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0466P)^2^+0.3299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3197
_reflns_number_total             3860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02380g2.cif
_cod_data_source_block           7a
_cod_depositor_comments          'Adding full bibliography for 7063969.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7063969
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.742
_shelx_estimated_absorpt_t_min   0.371
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C35(H35), C36(H36), C37(H37), C20(H20), C24(H24), C32(H32), C31(H31),
 C30(H30), C19(H19), C18(H18), C17(H17), C16(H16), C5(H5), C13(H13), C14(H14),
 C15(H15), C28(H28), C29(H29), C33(H33), C34(H34)
;
_shelx_res_checksum              6029
_olex2_submission_special_instructions 'No special instructions were received'