Crystal engineering of ionic cocrystals comprising Na/K salts of hesperetin with hesperetin molecules and solubility modulation.
Jin, Shasha; Haskins, Molly M.; Deng, Cheng Hua; Matos, Catiúcia R M O; Zaworotko, Michael J.; IUCrJ 10 (2023) –; doi:10.1107/S205225252300266X

data_1568923
_publ_section_title
;
 Crystal engineering of ionic cocrystals comprising Na/K salts of
 hesperetin with hesperetin molecules and solubility modulation.
;
_journal_issue                   3
_journal_name_full               IUCrJ
_journal_paper_doi               10.1107/S205225252300266X
_journal_volume                  10
_journal_year                    2023
_chemical_formula_moiety         'C32 H27 K O12, C H4 O'
_chemical_formula_sum            'C33 H31 K O13'
_chemical_formula_weight         674.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.2820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6211(3)
_cell_length_b                   20.3628(3)
_cell_length_c                   17.2684(3)
_cell_measurement_reflns_used    9446
_cell_measurement_temperature    113.00
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      4.34
_cell_volume                     6686.19(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39471
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.632
_diffrn_reflns_theta_max         66.632
_diffrn_reflns_theta_min         3.180
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.955
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0742 after correction.
The Ratio of minimum to maximum transmission is 0.7893.
The \l/2 correction factor is Not present.
;
_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    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         5880
_refine_ls_number_restraints     405
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0587P)^2^+17.3819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5781
_reflns_number_total             5880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5051.cif
_cod_data_source_block           HESKHE_xMeOH
_cod_database_code               1568923
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.787
_shelx_estimated_absorpt_t_min   0.657
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-H6
 0.84 with sigma of 0.02
 H11B-O11B
 0.84 with sigma of 0.02
 H11A-O11A
 0.84 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C22 \\sim C21 \\sim C2 \\sim C20 \\sim C16 \\sim C18 \\sim C3 \\sim C15 \\sim
C19 \\sim C12 \\sim C1 \\sim C14 \\sim C25 \\sim C29A \\sim C11 \\sim C13 \\sim
C7 \\sim C4 \\sim C5 \\sim C24 \\sim C6 \\sim C26A \\sim C10 \\sim C32 \\sim
C1M \\sim C23A \\sim C28A \\sim C30A \\sim C31A \\sim C8B \\sim C27A \\sim C9B
\\sim C23B \\sim C8A \\sim C9A \\sim C30B \\sim C31B \\sim C26B \\sim C27B
\\sim C28B \\sim C29B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(H24C)=Sof(H24D)=Sof(C23B)=Sof(H23B)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(O11B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=Sof(C26B)=
 Sof(C27B)=Sof(H27B)=Sof(C28B)=Sof(C29B)=1-FVAR(1)
 Sof(C29A)=Sof(O11A)=Sof(H24A)=Sof(H24B)=Sof(C26A)=Sof(C23A)=Sof(H23A)=
 Sof(C28A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C8B)=Sof(H8B)=Sof(C27A)=
 Sof(H27A)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=FVAR(1)
 Fixed Sof: H11A(0.70527) H11B(0.29473)
5.a Ternary CH refined with riding coordinates:
 C23A(H23A), C8B(H8B), C23B(H23B), C8A(H8A)
5.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C24(H24C,H24D), C9B(H9BA,H9BB), C9A(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C7(H7), C6(H6A), C30A(H30A), C31A(H31A), C27A(H27A),
 C30B(H30B), C31B(H31B), C27B(H27B)
5.d Fitted hexagon refined as free rotating group:
 C30B(C31B,C26B,C27B,C28B,C29B)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C32(H32A,H32B,H32C), C1M(H1MA,H1MB,H1MC)
5.f Idealised tetrahedral OH refined as rotating group:
 O6(H6), O1M(H1M)
;
_shelx_res_checksum              10709
_shelx_hkl_checksum              30108
_shelx_fab_checksum              41496
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'