Unleashing naphthopyranopyrimidine's anticancer potential: a deep eutectic solvent (DES) study
Das, Arindam; Dey, Sovan; Yadav, Ram Naresh; Dutta, Prajna; Dhiman, Shubham; Boruah, Palash Jyoti; Sarkar, Koushik; Sahu, Abhishek; Jana, Anupam; Paul, Amit Kumar; Hossain, Md. Firoj; New Journal of Chemistry 48 (2024) 7566–7578; doi:10.1039/D4NJ00796D

data_7063084
_publ_section_title
;
 Unleashing naphthopyranopyrimidine's anticancer potential: a deep
 eutectic solvent (DES) study
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7566
_journal_page_last               7578
_journal_paper_doi               10.1039/D4NJ00796D
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C23 H17 N3 O5'
_chemical_formula_sum            'C23 H17 N3 O5'
_chemical_formula_weight         415.39
_chemical_name_systematic
8,10-dimethyl-12-(4-nitrophenyl)-7a,8,11a,12-tetrahydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-08 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.31509(6)
_cell_length_b                   19.69557(13)
_cell_length_c                   20.17380(14)
_cell_measurement_reflns_used    32945
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.0230
_cell_measurement_theta_min      2.1730
_cell_volume                     3701.21(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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     44.00 127.00   0.50    0.20    --   96.67-145.00-120.00  166
  2  \w     41.00 100.00   0.50    0.20    --   41.08-138.00-150.00  118
  3  \w    -83.00 -14.00   0.50    0.20    --  -82.50  68.00-140.00  138
  4  \w    -65.00  27.00   0.50    0.20    --  -41.08  68.00-140.00  184
  5  \w    -68.00  28.00   0.50    0.20    --  -41.08  77.00 -22.00  192
  6  \w   -105.00 -14.00   0.50    0.20    --  -82.50  77.00  92.00  182
  7  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  90.00   64
  8  \w     14.00 110.00   0.50    0.20    --   41.08  77.00  92.00  192
  9  \w     70.00 165.00   0.50    0.20    --   96.67  77.00  92.00  190
 10  \w     70.00 165.00   0.50    0.20    --   96.67  77.00 120.00  190
 11  \w     70.00 165.00   0.50    0.20    --   96.67  77.00 -22.00  190
 12  \w     14.00 110.00   0.50    0.20    --   41.08  77.00 -90.00  192
 13  \w     17.00 109.00   0.50    0.20    --   41.08  68.00-140.00  184
 14  \w     73.00 165.00   0.50    0.20    --   96.67  68.00-180.00  184
 15  \w     73.00 165.00   0.50    0.20    --   96.67  68.00-140.00  184
 16  \w     82.00 167.00   0.50    0.20    --   96.67  25.00  30.00  170
 17  \w     82.00 167.00   0.50    0.20    --   96.67  25.00 -60.00  170
 18  \w     75.00 164.00   0.50    0.20    --   96.67  59.00  30.00  178
 19  \w     75.00 164.00   0.50    0.20    --   96.67  59.00  60.00  178
 20  \w     75.00 164.00   0.50    0.20    --   96.67  59.00 150.00  178
 21  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 120.00   54
 22  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00  85.00  108
 23  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00 120.00   78
 24  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00  30.00   78
 25  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00   0.00   78
 26  \w     28.00 105.00   0.50    0.20    --   96.67 -77.00 -33.00  154
 27  \w     28.00 105.00   0.50    0.20    --   96.67 -77.00-147.00  154
 28  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-150.00   78
 29  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-120.00   78
 30  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00-120.00   54
 31  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 -90.00   54
 32  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 33  \w    -27.00  68.00   0.50    0.20    --   41.08 -77.00 -33.00  190
 34  \w    -27.00  65.00   0.50    0.20    --   41.08 -68.00  85.00  184
 35  \w    -29.00  31.00   0.50    0.20    --   41.08 -25.00 120.00  120
 36  \w    -27.00  68.00   0.50    0.20    --   41.08 -77.00-147.00  190
 37  \w    -34.00  24.00   0.50    0.20    --   41.08 -12.00-180.00  116
 38  \w   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00-120.00  192
 39  \w   -108.00 -18.00   0.50    0.20    --  -41.08 -64.00 -90.00  180
 40  \w   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00   0.00  192
 41  \w   -109.00 -17.00   0.50    0.20    --  -41.08 -68.00  85.00  184
 42  \w   -108.00 -18.00   0.50    0.20    --  -41.08 -64.00 150.00  180
 43  \w   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00 120.00  192
 44  \w   -108.00 -22.00   0.50    0.20    --  -41.08 -50.00   0.00  172
 45  \w   -107.00 -26.00   0.50    0.20    --  -41.08 -38.00-180.00  162
 46  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00-147.00  192
 47  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -33.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118889000
_diffrn_orient_matrix_UB_12      -0.0570682000
_diffrn_orient_matrix_UB_13      0.0519260000
_diffrn_orient_matrix_UB_21      0.1383998000
_diffrn_orient_matrix_UB_22      -0.0324671000
_diffrn_orient_matrix_UB_23      -0.0272352000
_diffrn_orient_matrix_UB_31      0.0896869000
_diffrn_orient_matrix_UB_32      0.0425318000
_diffrn_orient_matrix_UB_33      0.0489333000
_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  0.0982
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.186
_diffrn_reflns_theta_min         4.383
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728
_exptl_crystal_preparation       'Crystal was prepared from ethylacetate'
_exptl_crystal_recrystallization_method
'crystal was prepared from ethyl acetate solvent'
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00147(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0516P)^2^+1.7747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3241
_reflns_number_total             3378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00796d2.cif
_cod_data_source_block           kskkc054_auto
_cod_depositor_comments          'Adding full bibliography for 7063084.cif.'
_cod_database_code               7063084
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.998
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H31A,H31B,H31C} of C31
 At 1.5 times of:
  {H30A,H30B,H30C} of C30
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C3(H3), C24(H24), C18(H18), C23(H23), C21(H21), C16(H16),
 C20(H20), C2(H2)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              10558
_shelx_hkl_checksum              31996
_olex2_exptl_crystal_mounting_method 'crystal mounted fron rigako instrument'
_olex2_submission_original_sample_id SD10054
_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 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.543