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_7250113
_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, C4 H6 N2'
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28
_chemical_name_systematic        EG-2MIE
_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
_audit_creation_date             2025-01-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-20 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                110.381(2)
_cell_angle_beta                 91.880(2)
_cell_angle_gamma                94.517(2)
_cell_formula_units_Z            4
_cell_length_a                   8.51680(10)
_cell_length_b                   11.7510(2)
_cell_length_c                   14.3094(3)
_cell_measurement_reflns_used    17180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.8120
_cell_measurement_theta_min      4.0670
_cell_volume                     1335.49(4)
_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 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.962
_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    -25.00  94.00   0.50    0.50    --    5.00  57.00 150.00  238
  2  \w    -79.00  41.00   0.50    0.50    --  -48.80  57.00  30.00  240
  3  \w   -138.00 -11.00   0.50    0.50    --  -48.80 -30.00-110.06  254
  4  \w    -82.00  41.00   0.50    0.50    --  -48.80  38.00 -90.00  246
  5  \w    -83.00  41.00   0.50    0.50    --  -48.80  72.00  90.00  248
  6  \w   -144.00 -21.00   0.50    0.50    -- -110.00  72.00-150.00  246
  7  \w   -199.00 -80.00   0.50    0.50    -- -110.00 -57.00  30.00  238
  8  \w   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 120.00  246
  9  \w   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  246
 10  \w   -144.00 -21.00   0.50    0.50    -- -110.00  72.00-180.00  246
 11  \w   -199.00 -75.00   0.50    0.50    -- -110.00 -36.00 -20.96  248
 12  \w   -199.00 -77.00   0.50    0.50    -- -110.00 -38.00  60.00  244
 13  \w   -144.00 -21.00   0.50    0.50    -- -110.00  72.00   0.00  246
 14  \w   -199.00 -80.00   0.50    0.50    -- -110.00 -50.00-108.10  238
 15  \w   -199.00 -80.00   0.50    0.50    -- -110.00 -49.00-175.79  238
 16  \w   -199.00 -78.00   0.50    0.50    -- -110.00 -65.00  97.74  242
 17  \w   -140.00 -21.00   0.50    0.50    -- -110.00  57.00 -90.00  238
 18  \w   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 -60.00  246
 19  \w   -199.00 -77.00   0.50    0.50    -- -110.00 -38.00 150.00  244
 20  \w   -107.00 -81.00   0.50    0.50    -- -110.00  72.00 -90.00   52
 21  \w    -94.00 -49.00   0.50    0.50    -- -110.00  72.00  30.00   90
 22  \w   -141.00 -22.00   0.50    0.50    -- -110.00  72.00  90.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23140
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.042
_diffrn_reflns_theta_min         4.032
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68565
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0755P)^2^+0.5465P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5296
_reflns_number_total             5544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00174a2.cif
_cod_data_source_block           EG-2MIE
_cod_depositor_comments
'Adding full bibliography for 7250113--7250114.cif.'
_cod_database_code               7250113
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.811
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H9-H5
 2.15 with sigma of 0.01
 H4-H10
 2.15 with sigma of 0.01
 N2-C2 \\sim N5-C30
 with sigma of 0.02
 N2-C4 \\sim N5-C28
 with sigma of 0.02
 N1-C2 \\sim N6-C30
 with sigma of 0.02
 N1-C3 \\sim N6-C29
 with sigma of 0.02
 C2-C1 \\sim C30-C27
 with sigma of 0.02
 C3-C4 \\sim C29-C28
 with sigma of 0.02
 N2-N1 \\sim N5-N6
 with sigma of 0.04
 N2-C3 \\sim N5-C29
 with sigma of 0.04
 N2-C1 \\sim N5-C27
 with sigma of 0.04
 N1-C4 \\sim N6-C28
 with sigma of 0.04
 N1-C1 \\sim N6-C27
 with sigma of 0.04
 C2-C3 \\sim C30-C29
 with sigma of 0.04
 C2-C4 \\sim C30-C28
 with sigma of 0.04
3. Others
 Sof(N5)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(N6)=Sof(C30)=Sof(C27)=
 Sof(H27A)=Sof(H27B)=Sof(H27C)=1-FVAR(1)
 Sof(N2)=Sof(N1)=Sof(C2)=Sof(C3)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(C1)=Sof(H1A)=
 Sof(H1B)=Sof(H1C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C22(H22), C17(H17), C26(H26), C8(H8A), C7(H7), C3(H3B), C4(H4A),
 C28(H28), C29(H29)
4.c Tetrahedral OH refined with riding coordinates:
 O9(H9)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C),
 C27(H27A,H27B,H27C)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              542
_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
;