Design, synthesis, and evaluation of 1,4-naphthoquinone-chromene hybrids as potential anti-K562 and A549 agents
Zhang, Wen-Hui; Zhang, Bo; Pan, Bo-Wen; Liu, Xiong-Wei; Yin, Zhi-Gang; Zhuo, Yu-Zhou; Lei, Chuan-wen; Zhou, Ying; New Journal of Chemistry 48 (2024) 5334–5345; doi:10.1039/D3NJ05743G

data_7063042
_publ_section_title
;
 Design, synthesis, and evaluation of 1,4-naphthoquinone-chromene hybrids
 as potential anti-K562 and A549 agents
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5334
_journal_page_last               5345
_journal_paper_doi               10.1039/D3NJ05743G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C24 H17 F N2 O6'
_chemical_formula_sum            'C24 H17 F N2 O6'
_chemical_formula_weight         448.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-19
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-11-17 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                92.135(5)
_cell_angle_beta                 101.797(6)
_cell_angle_gamma                108.263(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7150(8)
_cell_length_b                   10.4907(8)
_cell_length_c                   12.3492(6)
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7090
_cell_measurement_theta_min      3.6530
_cell_volume                     1043.27(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_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    -64.00  33.00   1.00    1.00    --  -40.92  37.00 -30.00   97
  2  \w     89.00 115.00   1.00    1.00    --   40.92  37.00-150.00   26
  3  \w     79.00 144.00   1.00    1.00    --  107.58 -15.00 -90.00   65
  4  \w    147.00 178.00   1.00    1.00    --  107.58  61.00   0.00   31
  5  \w    152.00 178.00   1.00    1.00    --  107.58 125.00  60.00   26
  6  \w    104.00 162.00   1.00    1.00    --  107.58 125.00  30.00   58
  7  \w     97.00 176.00   1.00    1.00    --  107.58  45.00  90.00   79
  8  \w    106.00 132.00   1.00    1.00    --  107.58 -61.00 120.00   26
  9  \w     76.00 103.00   1.00    1.00    --  107.58 -94.00  90.00   27
 10  \w     45.00  74.00   1.00    1.00    --  107.58 -61.00 120.00   29
 11  \w     43.00 136.00   1.00    1.00    --  107.58 -30.00  60.00   93
 12  \w     80.00 119.00   1.00    1.00    --  107.58  61.00   0.00   39
 13  \w     32.00  60.00   1.00    1.00    --  107.58 -15.00 -90.00   28
 14  \w     36.00 121.00   1.00    1.00    --  107.58 -61.00   0.00   85
 15  \w     55.00 121.00   1.00    1.00    --  107.58-125.00-120.00   66
 16  \w     35.00  82.00   1.00    1.00    --   40.92 -99.00  30.00   47
 17  \w     35.00 108.00   1.00    1.00    --  107.58 -94.00 -30.00   73
 18  \w      2.00  36.00   1.00    1.00    --   40.92 -99.00  60.00   34
 19  \w   -106.00 -17.00   1.00    1.00    --  -40.92 -37.00 150.00   89
 20  \w    -54.00 -17.00   1.00    1.00    --  -40.92 125.00  60.00   37
 21  \w    -96.00 -56.00   1.00    1.00    --  -40.92 125.00  60.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0974561000
_diffrn_orient_matrix_UB_12      -0.0867599000
_diffrn_orient_matrix_UB_13      -0.1109322000
_diffrn_orient_matrix_UB_21      -0.0847910000
_diffrn_orient_matrix_UB_22      -0.1145229000
_diffrn_orient_matrix_UB_23      0.0642509000
_diffrn_orient_matrix_UB_31      -0.1409228000
_diffrn_orient_matrix_UB_32      0.0596532000
_diffrn_orient_matrix_UB_33      -0.0015496000
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6860
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.837
_diffrn_reflns_theta_min         3.678
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0645P)^2^+0.2765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3769
_reflns_number_total             4079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05743g2.cif
_cod_data_source_block           yes-21
_cod_depositor_comments          'Adding full bibliography for 7063042.cif.'
_cod_database_code               7063042
_shelx_shelxl_version_number     2018/3
_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 N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 N2(H2A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              1227
_shelx_fab_checksum              68356
_olex2_date_sample_data_collection 2023-05-18
_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.429