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_1568924
_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         'C16 H17 K O8, H2 O'
_chemical_formula_sum            'C16 H19 K O9'
_chemical_formula_weight         394.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9343(3)
_cell_length_b                   7.8657(2)
_cell_length_c                   31.4425(7)
_cell_measurement_reflns_used    9265
_cell_measurement_temperature    113.0
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      4.24
_cell_volume                     3446.19(14)
_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      113.0
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            29419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.612
_diffrn_reflns_theta_max         66.612
_diffrn_reflns_theta_min         2.811
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.154
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.7197.
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    1.520
_exptl_crystal_description       plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0493P)^2^+5.4499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2903
_reflns_number_total             3040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5051.cif
_cod_data_source_block           HESK_3H2O
_cod_database_code               1568924
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H8B,H5,H2} of C8B, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups, {H1A,H1B,H1C} of C1
2. Restrained distances
 H2-O2
 0.84 with sigma of 0.02
 H5-O5
 0.84 with sigma of 0.02
 C9B-C8B \\sim C8A-C9A
 with sigma of 0.02
 C9A-C10 \\sim C9B-C10
 with sigma of 0.02
 O3-C8B \\sim O3-C8A
 with sigma of 0.02
3. Rigid bond restraints
 C9B, C9A, C8A, C8B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(C8B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C9B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(C9B)=Sof(H9BA)=Sof(H9BB)=1-FVAR(1)
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=FVAR(1)
 Sof(C8B)=Sof(H8B)=1-FVAR(2)
 Sof(C8A)=Sof(H8A)=FVAR(2)
6.a Free rotating group:
 O3W(H3WA,H3WB)
6.b Rotating group:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
6.c Ternary CH refined with riding coordinates:
 C8A(H8A), C8B(H8B)
6.d Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9B(H9BA,H9BB)
6.e Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C4(H4), C7(H7), C6(H6)
6.f Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              27314
_shelx_hkl_checksum              8898
_olex2_submission_special_instructions 'No special instructions were received'