n → π* and chalcogen bonds in azole-substituted isoindole derivatives: a combined crystallographic and computational study
Kolesnik, Irina A.; Potkin, Vladimir I.; Grigoriev, Mikhail S.; Gomila, Rosa M.; Nikitina, Eugeniya V.; Zaytsev, Vladimir P.; Zubkov, Fedor I.; Frontera, Antonio; CrystEngComm 27 (2025) 6155–6162; doi:10.1039/D5CE00673B

data_7250783
_publ_section_title
;
 n \\rightarrow \p* and chalcogen bonds in azole-substituted isoindole
 derivatives: a combined crystallographic and computational study
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              6155
_journal_page_last               6162
_journal_paper_doi               10.1039/D5CE00673B
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C23 H20 N4 O4 S'
_chemical_formula_weight         448.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-12-29 deposited with the CCDC.	2025-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4671(16)
_cell_length_b                   5.1768(5)
_cell_length_c                   21.844(2)
_cell_measurement_reflns_used    4142
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.99
_cell_volume                     1975.2(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32769
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_min         4.106
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       bulk
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5704
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0454P)^2^+0.2872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4600
_reflns_number_total             5704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00673b2.cif
_cod_data_source_block           ZH62_LT
_cod_depositor_comments
'Adding full bibliography for 7250780--7250783.cif.'
_cod_database_code               7250783
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              834