Design and synthesis of tetrahydrochromeno[3,4-e]isoindole-1,3(2H,3aH)-dione derivatives via the Diels–Alder reaction: molecular docking, antibacterial activity, ADMET analysis and photophysical properties
Parida, Sonali Priyadarshini; Mohapatra, Seetaram; Mohapatra, Suhasini; Behera, Tankadhar; Nayak, Sabita; Sahoo, Chita Ranjan; RSC Advances 15 (2025) 14499–14517; doi:10.1039/D5RA02212F

data_7250355
_publ_section_title
;
 Design and synthesis of
 tetrahydrochromeno[3,4-e]isoindole-1,3(2H,3aH)-dione derivatives via the
 Diels--Alder reaction: molecular docking, antibacterial activity, ADMET
 analysis and photophysical properties
;
_journal_issue                   18
_journal_name_full               'RSC Advances'
_journal_page_first              14499
_journal_page_last               14517
_journal_paper_doi               10.1039/D5RA02212F
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C29 H33 N O4, 0.67(H2 O)'
_chemical_formula_sum            'C29 H34.34 N O4.67'
_chemical_formula_weight         471.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-30 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.674(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1175(5)
_cell_length_b                   11.0197(5)
_cell_length_c                   22.3483(13)
_cell_measurement_reflns_used    11275
_cell_measurement_temperature    266(12)
_cell_measurement_theta_max      78.1470
_cell_measurement_theta_min      3.9300
_cell_volume                     2491.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      266(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.928
_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    -90.00  -8.00   0.50    1.00    --  -38.50 129.00   8.00  164
  2  \w     30.00 102.00   0.50    1.00    --   49.56-129.00 -64.00  144
  3  \w     36.00 110.00   0.50    1.00    --   49.56-141.00 123.00  148
  4  \w     95.00 171.00   0.50    4.00    --  107.46 129.00   8.00  152
  5  \w     45.00 115.00   0.50    4.00    --  107.46-129.00 -64.00  140
  6  \w     88.00 171.00   0.50    4.00    --  107.46 141.00-179.00  166
  7  \w    -99.00 -14.00   0.50    1.00    --  -38.50 141.00-179.00  170
  8  \w   -105.00 -35.00   0.50    1.00    --  -38.50 -37.00 120.00  140
  9  \w   -101.00 -27.00   0.50    1.00    --  -38.50 -57.00 120.00  148
 10  \w     46.00 116.00   0.50    1.00    --   49.56  37.00 -30.00  140
 11  \w     39.00 111.00   0.50    4.00    --  107.46 -30.00 -30.00  144
 12  \w     43.00 112.00   0.50    4.00    --  107.46 -45.00 -90.00  138
 13  \w     45.00 121.00   0.50    4.00    --  107.46 -61.00-120.00  152
 14  \w    103.00 172.00   0.50    4.00    --  107.46  77.00 120.00  138
 15  \w     45.00 113.00   0.50    4.00    --  107.46-125.00-120.00  136
 16  \w    105.00 140.00   0.50    4.00    --  107.46  77.00-120.00   70
 17  \w    103.00 137.00   0.50    4.00    --  107.46  77.00-150.00   68
 18  \w     55.00 109.00   0.50    4.00    --  107.46 -45.00  30.00  108
 19  \w    119.00 164.00   0.50    4.00    --  107.46  45.00  90.00   90
 20  \w    124.00 171.00   0.50    4.00    --  107.46  30.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0589530000
_diffrn_orient_matrix_UB_12      0.0371422000
_diffrn_orient_matrix_UB_13      0.0606916000
_diffrn_orient_matrix_UB_21      -0.1030908000
_diffrn_orient_matrix_UB_22      0.0794503000
_diffrn_orient_matrix_UB_23      -0.0325473000
_diffrn_orient_matrix_UB_31      -0.0953380000
_diffrn_orient_matrix_UB_32      -0.1088444000
_diffrn_orient_matrix_UB_33      -0.0031348000
_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  0.0514
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19726
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         82.354
_diffrn_reflns_theta_min         3.956
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1011
_exptl_crystal_preparation       'As per reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0612P)^2^+1.0525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4374
_reflns_number_total             5145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra02212f2.cif
_cod_data_source_block           ska-spp-228_auto
_cod_database_code               7250355
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'colourless block'
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.812
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Sof(O5)=Sof(H5A)=Sof(H5B)=FVAR(1)
3.a Free rotating group:
 O5(H5A,H5B)
3.b Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
3.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C18(H18), C19(H19), C21(H21), C22(H22)
3.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              72712
_shelx_hkl_checksum              94391
_olex2_exptl_crystal_mounting_method 'mounted on a loop'
_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 2.344
_oxdiff_exptl_absorpt_empirical_full_min 0.439