Influence of C3′- and C4′-substitutions on fluorescence, crystal packing, and physicochemical properties of flavonol
Demidov, Oleksii O.; Chepeleva, Ludmila V.; Shishkina, Svitlana V.; Gladkov, Eugene S.; Kyrychenko, Alexander; Linnik, Rostyslav P.; Roshal, Alexander D.; RSC Advances 15 (2025) 36300–36318; doi:10.1039/D5RA05790F

data_7250927
_publ_section_title
;
 Influence of C3&#x2032;- and C4&#x2032;-substitutions on fluorescence,
 crystal packing, and physicochemical properties of flavonol
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              36300
_journal_page_last               36318
_journal_paper_doi               10.1039/D5RA05790F
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C22 H16 O4'
_chemical_formula_sum            'C22 H16 O4'
_chemical_formula_weight         344.35
_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   geom
_audit_creation_date             2025-09-16
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-17 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.035(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.780(2)
_cell_length_b                   4.9187(6)
_cell_length_c                   19.121(2)
_cell_measurement_reflns_used    3130
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.32
_cell_measurement_theta_min      2.27
_cell_volume                     1685.5(3)
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_collection       'APEXII (Bruker AXS, 2014)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      172.65
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21576
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.135
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0648P)^2^+1.0650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1920
_reflns_number_total             2973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra05790f2.cif
_cod_data_source_block           3k
_cod_original_cell_volume        1685.6(3)
_cod_database_code               7250927
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.982
_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 O(H) groups
2. Restrained distances
 C17-C22B
 1.39 with sigma of 0.002
 C22B-C21B
 1.39 with sigma of 0.002
 C21B-C20
 1.39 with sigma of 0.002
 C20-C19B
 1.39 with sigma of 0.002
 C19B-C18B
 1.39 with sigma of 0.002
 C18B-C17
 1.39 with sigma of 0.002
 C17-C22A
 1.39 with sigma of 0.002
 C22A-C21A
 1.39 with sigma of 0.002
 C21A-C20
 1.39 with sigma of 0.002
 C20-C19A
 1.39 with sigma of 0.002
 C19A-C18A
 1.39 with sigma of 0.002
 C18A-C17
 1.39 with sigma of 0.002
3. Others
 Fixed Sof: H20(0.5) H20A(0.5) C18A(0.5) H18A(0.5) C19A(0.5) H19A(0.5)
 C21A(0.5) H21A(0.5) C22A(0.5) H22A(0.5) C18B(0.5) H18B(0.5) C19B(0.5)
 H19B(0.5) C21B(0.5) H21B(0.5) C22B(0.5) H22B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C15(H15),
 C20(H20), C20(H20A), C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A),
 C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B)
4.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              39098
_olex2_submission_special_instructions 'No special instructions were received'