Divergent hetero-[8+<i>n</i>] higher order cycloadditions of tropothione and enals catalyzed by <i>N</i>-heterocyclic carbenes.
Dybowska, Joanna; Przydacz, Artur; Olczyk, Weronika; Sieroń, Lesław; Skrzyńska, Anna; Albrecht, Łukasz; Chemical communications (Cambridge, England) 61 (2025) 12119–12122; doi:10.1039/d5cc02536b

data_7134841
_publ_section_title
;
 Divergent hetero-[8+<i>n</i>] higher order cycloadditions of tropothione
 and enals catalyzed by <i>N</i>-heterocyclic carbenes.
;
_journal_issue                   65
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12119
_journal_page_last               12122
_journal_paper_doi               10.1039/d5cc02536b
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H19 N3 O3 S'
_chemical_formula_sum            'C24 H19 N3 O3 S'
_chemical_formula_weight         429.48
_chemical_name_systematic
;
(4S,4aR,4bS,5R,11S,11aR)-4,8-diphenyl-4,4a,4b,5-tetrahydro-7H,11H-5,11-ethenothiopyrano[2',3':1,3]cyclopropa[1,2-d][1,2,4]triazolo[1,2-a]pyridazine-2,7,9(3H,8H)-trione
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2025-03-11 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.687(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5801(1)
_cell_length_b                   5.9732(1)
_cell_length_c                   15.3490(1)
_cell_measurement_reflns_used    36524
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.599
_cell_measurement_theta_min      3.018
_cell_volume                     1011.51(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43103
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         67.72
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.773
_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.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'W=1/[\S^2^(FO^2^)+(0.0475P)^2^+0.3689P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                3520
_reflns_number_total             3543
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d5cc02536b2.cif
_cod_data_source_block           JD-394B
_cod_depositor_comments
'Adding full bibliography for 7134840--7134841.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7134841
_shelx_res_checksum              79986
_shelx_hkl_checksum              4205