Base-promoted decarboxylative condensation of cinnamonitriles and phenylacetic acids with sulfur: direct access to azatrithiapentalenes.
Chu, Ngoc Lan; Tran, Quang Huy; Tran, Quynh Trang; Bui, Thai Thanh Thu; Mac, Dinh Hung; Ngo, Quoc Anh; Pham, Quoc Nghi; Nguyen, Le Anh; Retailleau, Pascal; Nguyen, Thanh Binh; Organic & biomolecular chemistry 24 (2026) 1424–1427; doi:10.1039/d5ob01790d

data_7160986
_publ_section_title
;
 Base-promoted decarboxylative condensation of cinnamonitriles and
 phenylacetic acids with sulfur: direct access to azatrithiapentalenes.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1424
_journal_page_last               1427
_journal_paper_doi               10.1039/d5ob01790d
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C24 H24 N2 S4'
_chemical_formula_sum            'C24 H24 N2 S4'
_chemical_formula_weight         468.736
_chemical_name_systematic
1,2-bis(5-(4-isopropylphenyl)isothiazol-3-yl)disulfane
_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
_audit_creation_date             2025-01-10
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-07-21 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.920(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0690(5)
_cell_length_b                   18.3904(7)
_cell_length_c                   8.9706(4)
_cell_measurement_reflns_used    10294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5360
_cell_measurement_theta_min      2.8740
_cell_volume                     2319.70(16)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac6-020 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9973
_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    -29.00  90.00   0.50   60.00    --    0.80  57.00-150.00  238
  2  \w    -31.00  87.00   0.50   60.00    --    0.80  38.00  60.00  236
  3  \w     14.00  73.00   0.50   60.00    --   -1.50  57.00 -60.00  118
  4  \w     22.00  87.00   0.50   60.00    --   -1.50  38.00 120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161739000
_diffrn_orient_matrix_UB_12      0.0363982000
_diffrn_orient_matrix_UB_13      -0.0072225000
_diffrn_orient_matrix_UB_21      0.0473603000
_diffrn_orient_matrix_UB_22      0.0126679000
_diffrn_orient_matrix_UB_23      0.0108659000
_diffrn_orient_matrix_UB_31      0.0063869000
_diffrn_orient_matrix_UB_32      -0.0016005000
_diffrn_orient_matrix_UB_33      -0.0780095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9973
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31472
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9973
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.53
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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    1.342
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             984.0
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.4654
_refine_diff_density_min         -0.3741
_refine_diff_density_rms         0.0435
_refine_ls_d_res_high            0.7801
_refine_ls_d_res_low             8.0589
_refine_ls_goodness_of_fit_ref   1.0841
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     487
_refine_ls_number_reflns         5098
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.0827
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0201P)^2^+1.0517P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -17
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                4238
_reflns_number_total             5098
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01790d2.cif
_cod_data_source_block           B22951
_cod_database_code               7160986
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(H11E) \\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
Uanis(H10B) \\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2025-01-10_09-24-59
;
_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 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.781