Improvement of humidity stability of ethyl gallate by the cocrystal strategy and study of dissolution behavior of the cocrystal
Pan, Ziqi; Zhang, Menglong; Hou, Xinyu; Yang, Huiwen; Rong, Hua; Song, Haibin; Zhang, Yong; Chen, Wei; Wu, Songgu; CrystEngComm 27 (2025) 2577–2590; doi:10.1039/D5CE00174A

data_7250114
_publ_section_title
;
 Improvement of humidity stability of ethyl gallate by the cocrystal
 strategy and study of dissolution behavior of the cocrystal
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2577
_journal_page_last               2590
_journal_paper_doi               10.1039/D5CE00174A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C9 H10 O5, 2.5(H2 O)'
_chemical_formula_sum            'C9 H15 O7.5'
_chemical_formula_weight         243.21
_chemical_name_systematic        EG-Hydrate
_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     direct
_audit_creation_date             2024-12-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-06 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                79.478(2)
_cell_angle_beta                 83.701(2)
_cell_angle_gamma                82.920(2)
_cell_formula_units_Z            4
_cell_length_a                   7.0043(2)
_cell_length_b                   11.7986(3)
_cell_length_c                   14.0615(4)
_cell_measurement_reflns_used    14113
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1580
_cell_measurement_theta_min      3.1860
_cell_volume                     1129.27(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_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     22.00  48.00   0.50    0.05    --   59.34 -94.00-180.00   52
  2  \w     24.00  49.00   0.50    0.05    --   59.34 -94.00 -90.00   50
  3  \w   -101.00 -50.00   0.50    0.05    --  -60.24 -15.00 -30.00  102
  4  \w    -96.00 -40.00   0.50    0.05    --  -60.24 -15.00 -90.00  112
  5  \w   -107.00 -53.00   0.50    0.05    --  -60.24 -15.00  30.00  108
  6  \w    -68.00 -42.00   0.50    0.05    --  -60.24 -15.00-180.00   52
  7  \w    -67.00 -42.00   0.50    0.05    --  -60.24 -15.00 150.00   50
  8  \w     37.00  63.00   0.50    0.05    --   72.68 -94.00  30.00   52
  9  \w     66.00  92.00   0.50    0.05    --   72.68-125.00-120.00   52
 10  \w     32.00  57.00   0.50    0.05    --   72.68 -94.00 -30.00   50
 11  \w     33.00  65.00   0.50    0.05    --   72.68 -94.00  90.00   64
 12  \w     28.00  53.00   0.50    0.05    --   72.68-125.00-120.00   50
 13  \w    -96.00 -70.00   0.50    0.05    --  -74.29 125.00-120.00   52
 14  \w   -121.00 -71.00   0.50    0.05    --  -74.29 -15.00  90.00  100
 15  \w    -56.00 -29.00   0.50    0.05    --  -74.29 125.00-120.00   54
 16  \w   -120.00 -85.00   0.50    0.05    --  -78.05 -15.00-150.00   70
 17  \w   -121.00 -80.00   0.50    0.05    --  -78.05 -15.00 150.00   82
 18  \w   -100.00 -72.00   0.50    0.05    --  -78.05 125.00   0.00   56
 19  \w    -96.00 -60.00   0.50    0.05    --  -78.05 -15.00 -30.00   72
 20  \w   -125.00 -91.00   0.50    0.05    --  -78.05 -15.00  60.00   68
 21  \w     90.00 118.00   0.50    0.05    --   79.03  15.00  60.00   56
 22  \w     53.00  99.00   0.50    0.05    --   79.03  15.00-150.00   92
 23  \w     76.00 127.00   0.50    0.05    --   79.03  15.00   0.00  102
 24  \w     41.00  66.00   0.50    0.05    --   79.03-125.00 -60.00   50
 25  \w     76.00 101.00   0.50    0.05    --   79.03-125.00 -60.00   50
 26  \w     37.00  62.00   0.50    0.05    --   79.03-125.00-120.00   50
 27  \w     75.00 101.00   0.50    0.05    --   79.03-125.00-150.00   52
 28  \w     43.00  69.00   0.50    0.05    --   79.03-125.00-150.00   52
 29  \w     74.00  99.00   0.50    0.05    --   79.03  15.00  30.00   50
 30  \w     76.00 101.00   0.50    0.05    --   79.03-125.00-120.00   50
 31  \w     57.00  83.00   0.50    0.05    --   79.03 -94.00-180.00   52
 32  \w    -91.00 -62.00   0.50    0.05    --  -82.00 109.00 -99.63   58
 33  \w    -83.00 -44.00   0.50    0.05    --  -82.00  90.00 125.60   78
 34  \w    -90.00 -37.00   0.50    0.05    --  -82.00 129.00 -53.37  106
 35  \w    -73.00 -48.00   0.50    0.05    --  -82.00 108.00 158.96   50
 36  \w   -130.00-105.00   0.50    0.05    --  -82.00 -41.00-161.98   50
 37  \w    -83.00 -38.00   0.50    0.05    --  -82.00 131.00  12.61   90
 38  \w    -68.00 -43.00   0.50    0.05    --  -82.00  71.00-124.78   50
 39  \w    -97.00 -69.00   0.50    0.05    --  -82.00 114.00   0.07   56
 40  \w    -64.00 -38.00   0.50    0.05    --  -82.00 125.00 -67.17   52
 41  \w    -90.00 -56.00   0.50    0.05    --  -82.00 103.00-139.35   68
 42  \w   -100.00 -74.00   0.50    0.05    --  -82.00 125.00 -67.17   52
 43  \w   -124.00 -98.00   0.50    0.05    --  -82.00 -61.00 174.10   52
 44  \w    -98.00 -37.00   0.50    0.05    --  -82.00 131.00-108.42  122
 45  \w    -81.00 -49.00   0.50    0.05    --  -82.00 125.00  31.24   64
 46  \w    -77.00 -37.00   0.50    0.05    --  -82.00 125.00  -4.40   80
 47  \w    -75.00 -50.00   0.50    0.05    --  -82.00  94.00-105.59   50
 48  \w   -123.00 -97.00   0.50    0.05    --  -82.00 -66.00  33.47   52
 49  \w    -67.00 -38.00   0.50    0.05    --  -82.00 129.00 151.47   58
 50  \w   -124.00 -98.00   0.50    0.05    --  -82.00 -58.00 -78.36   52
 51  \w    -92.00 -40.00   0.50    0.05    --  -82.00 109.00  82.21  104
 52  \w   -127.00 -98.00   0.50    0.05    --  -82.00 -52.00-137.26   58
 53  \w    -64.00 -39.00   0.50    0.05    --  -82.00 130.00 -92.42   50
 54  \w   -131.00-106.00   0.50    0.05    --  -82.00 -36.00 149.85   50
 55  \w    -63.00 -38.00   0.50    0.05    --  -82.00 131.00  50.05   50
 56  \w    -96.00 -50.00   0.50    0.05    --  -82.00 114.00 -18.82   92
 57  \w   -124.00 -98.00   0.50    0.05    --  -82.00 -47.00 -56.82   52
 58  \w   -123.00 -98.00   0.50    0.05    --  -82.00 -36.00 -29.43   50
 59  \w    -64.00 -39.00   0.50    0.05    --  -82.00 111.00 -64.40   50
 60  \w    -95.00 -67.00   0.50    0.05    --  -82.00 118.00 167.57   56
 61  \w   -123.00 -98.00   0.50    0.05    --  -82.00 -55.00 137.49   50
 62  \w    -94.00 -68.00   0.50    0.05    --  -82.00 118.00 108.56   52
 63  \w    -66.00 -36.00   0.50    0.05    --  -82.00 127.00-146.50   60
 64  \w    -97.00 -47.00   0.50    0.05    --  -82.00 114.00  60.40  100
 65  \w    -97.00 -64.00   0.50    0.05    --  -82.00 114.00 -75.14   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1345148000
_diffrn_orient_matrix_UB_12      -0.1110111000
_diffrn_orient_matrix_UB_13      -0.0120020000
_diffrn_orient_matrix_UB_21      0.1636463000
_diffrn_orient_matrix_UB_22      0.0740889000
_diffrn_orient_matrix_UB_23      -0.0459205000
_diffrn_orient_matrix_UB_31      0.0681415000
_diffrn_orient_matrix_UB_32      -0.0048519000
_diffrn_orient_matrix_UB_33      0.1013140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19643
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.267
_diffrn_reflns_theta_min         3.209
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4504
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0530P)^2^+0.3569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4202
_reflns_number_total             4504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00174a2.cif
_cod_data_source_block           EG-Hydrate
_cod_depositor_comments
'Adding full bibliography for 7250113--7250114.cif.'
_cod_original_cell_volume        1129.26(6)
_cod_original_formula_sum        'C9 H15 O7.50'
_cod_database_code               7250114
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1. Restrained distances
 O29-H29A = O29-H29B
 0.87 with sigma of 0.02
 O30-H30A = O30-H30B
 0.87 with sigma of 0.02
 O31-H31A = O31-H31B
 0.87 with sigma of 0.02
 O32-H32A = O32-H32B
 0.87 with sigma of 0.02
 O33-H33A = O33-H33B
 0.87 with sigma of 0.02
 H29A-H29B
 1.38 with sigma of 0.04
 H30A-H30B
 1.38 with sigma of 0.04
 H31A-H31B
 1.38 with sigma of 0.04
 H32A-H32B
 1.38 with sigma of 0.04
 H33A-H33B
 1.38 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C20(H20), C16(H16), C2(H2)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O13(H13), O14(H14), O12(H12), O26(H26), O28(H28), O27(H27)
;
_shelx_res_checksum              38876
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.666