The short route to chalcogenurea-substituted 3a,6-epoxyisoindoles via an intramolecular Diels–Alder furan (IMDAF) reaction. Antibacterial and antifungal activity
Mertsalov, Dmitriy F.; Shchevnikov, Dmitriy M.; Lovtsevich, Lala V.; Novikov, Roman A.; Khrustalev, Victor N.; Grigoriev, Mikhail S.; Romanycheva, Anna A.; Shetnev, Anton A.; Bychkova, Olga P.; Trenin, Alexey S.; Zaytsev, Vladimir P.; New Journal of Chemistry 48 (2024) 12947–12959; doi:10.1039/D4NJ01174K

data_7063303
_publ_section_title
;
 The short route to chalcogenurea-substituted 3a,6-epoxyisoindoles via an
 intramolecular Diels--Alder furan (IMDAF) reaction. Antibacterial and
 antifungal activity
;
_journal_issue                   29
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12947
_journal_page_last               12959
_journal_paper_doi               10.1039/D4NJ01174K
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 Cl N2 O Se'
_chemical_formula_sum            'C15 H15 Cl N2 O Se'
_chemical_formula_weight         353.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-05-27 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.31793(12)
_cell_length_b                   9.33602(18)
_cell_length_c                   23.9880(5)
_cell_measurement_reflns_used    6961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.0
_cell_measurement_theta_min      5.1
_cell_volume                     1414.92(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9337
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.396
_diffrn_reflns_theta_min         3.685
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.300
_exptl_absorpt_correction_T_max  0.612
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.029(16)
_refine_ls_extinction_coef       0.00081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0271P)^2^+1.2993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0750
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                2771
_reflns_number_total             2870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01174k2.cif
_cod_data_source_block           7p
_cod_depositor_comments
'Adding full bibliography for 7063302--7063305.cif.'
_cod_database_code               7063303
_shelx_estimated_absorpt_t_min   0.524
_shelx_estimated_absorpt_t_max   0.647
_shelxl_version_number           2013-4
_shelx_res_checksum              2432
_shelx_hkl_checksum              47512