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_1568926
_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         'C34 H33 Na O13, C2 H6 O'
_chemical_formula_sum            'C36 H39 Na O14'
_chemical_formula_weight         718.66
_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             2022-02-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                81.871(4)
_cell_angle_beta                 74.681(5)
_cell_angle_gamma                68.049(5)
_cell_formula_units_Z            2
_cell_length_a                   10.8865(5)
_cell_length_b                   10.9884(6)
_cell_length_c                   16.1451(8)
_cell_measurement_reflns_used    8177
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.9020
_cell_measurement_theta_min      1.9720
_cell_volume                     1725.73(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065275000
_diffrn_orient_matrix_UB_12      -0.0191479000
_diffrn_orient_matrix_UB_13      0.0429202000
_diffrn_orient_matrix_UB_21      -0.0565309000
_diffrn_orient_matrix_UB_22      0.0569088000
_diffrn_orient_matrix_UB_23      0.0146845000
_diffrn_orient_matrix_UB_31      -0.0444109000
_diffrn_orient_matrix_UB_32      -0.0353453000
_diffrn_orient_matrix_UB_33      0.0046767000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.000
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         7061
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0607
_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^)+(0.0697P)^2^+1.0094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5100
_reflns_number_total             7061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5051.cif
_cod_data_source_block           HESNAH_2EtOH
_cod_database_code               1568926
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.998
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H5 of O5, H6 of O6, H8 of O8, All C(H,H) groups, All C(H,H,
  H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H1E of O1E, H2E of O2E
2. Restrained distances
 H11-O11
 0.84 with sigma of 0.02
 H2-O2
 0.84 with sigma of 0.02
 H8-O8
 0.84 with sigma of 0.02
 H5-O5
 0.84 with sigma of 0.02
 H6-O6
 0.84 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C9A, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C9B, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(C8B)=Sof(H8B)=1-FVAR(1)
 Sof(C8A)=Sof(H8A)=FVAR(1)
 Sof(C9B)=Sof(H9BA)=Sof(H9BB)=1-FVAR(2)
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C23(H23), C8A(H8A), C8B(H8B)
5.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C4E(H4EA,H4EB), C2E(H2EA,H2EB), C9A(H9AA,H9AB), C9B(H9BA,H9BB)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C22(H22), C18(H18), C27(H27), C30(H30), C4(H4), C31(H31),
 C7(H7), C6(H6A)
5.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C1(H1A,H1B,H1C), C3E(H3EA,H3EB,H3EC), C1E(H1EA,H1EB,H1EC)
5.e Idealised tetrahedral OH refined as rotating group:
 O2E(H2E), O1E(H1E)
;
_shelx_res_checksum              95309
_shelx_hkl_checksum              54527
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.642