Synthesis, cytotoxicity and antioxidant activity of new 1,3-dimethyl-8-(chromon-3-yl)-xanthine derivatives containing 2,6-di-tert-butylphenol fragments
Shatokhin, Stanislav S.; Tuskaev, Vladislav A.; Gagieva, Svetlana Ch.; Markova, Alina A.; Pozdnyakov, Dmitry I.; Denisov, Gleb L.; Melnikova, Elizaveta K.; Bulychev, Boris M.; Oganesyan, Eduard T.; New Journal of Chemistry 46 (2022) 621–631; doi:10.1039/D1NJ03726A

data_7061067
_publ_section_title
;
 Synthesis, cytotoxicity and antioxidant activity of new
 1,3-dimethyl-8-(chromon-3-yl)-xanthine derivatives containing
 2,6-di-tert-butylphenol fragments
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              621
_journal_page_last               631
_journal_paper_doi               10.1039/D1NJ03726A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C30 H32 N4 O5, 0.25(H2 O)'
_chemical_formula_sum            'C30 H32.5 N4 O5.25'
_chemical_formula_weight         533.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-13 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.420(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7391(8)
_cell_length_b                   25.2387(19)
_cell_length_c                   11.2459(9)
_cell_measurement_reflns_used    2488
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.64
_cell_measurement_theta_min      2.24
_cell_volume                     2759.3(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31316
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.495
_diffrn_reflns_theta_min         1.985
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0693 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8862.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       prism
_exptl_crystal_F_000             1130
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         8343
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0536P)^2^+0.7361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             8343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03726a2.cif
_cod_data_source_block           Shat70
_cod_depositor_comments          'Adding full bibliography for 7061067.cif.'
_cod_original_formula_sum        'C30 H32.50 N4 O5.25'
_cod_database_code               7061067
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C10) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C14) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(O4') = Uanis(O4)
Uanis(C8') = Uanis(C8)
Uanis(C16') = Uanis(C16)
Uanis(C9') = Uanis(C9)
Uanis(O3') = Uanis(O3)
Uanis(C15) = Uanis(C15')
Uanis(C10') = Uanis(C10)
Uanis(C14) = Uanis(C14')
Uanis(C11') = Uanis(C11)
Uanis(C13) = Uanis(C13')
Uanis(C12) = Uanis(C12')
3. Others
 Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C10')=Sof(C15')=Sof(C14')=
 Sof(H14')=Sof(C11')=Sof(H11')=Sof(C16')=Sof(C8')=Sof(O4')=Sof(O3')=Sof(C9')=
 Sof(H9')=1-FVAR(1)
 Sof(O4)=Sof(C15)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(C10)=Sof(C16)=Sof(C11)=Sof(H11)=
 Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(O3)=FVAR(1)
 Fixed Sof: O1W(0.25) H1WA(0.25) H1WB(0.25)
4.a Riding coordinates:
 O5(H5), O1W(H1WA,H1WB)
4.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C18(H18), C9(H9), C11(H11), C14(H14), C12(H12), C13(H13),
 C12'(H12'), C13'(H13'), C14'(H14'), C11'(H11'), C9'(H9')
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C25(H25A,H25B,H25C), C7(H7A,H7B,
 H7C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C6(H6A,H6B,H6C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              74829
_olex2_submission_special_instructions 'No special instructions were received'