Thermodynamics and molecular mechanism of the formation of the cocrystals of p-hydroxybenzoic acid and glutaric acid
Yang, Jinyue; Hong, Baohong; Wang, Na; Li, Xin; Huang, Xin; Bao, Ying; Xie, Chuang; Hao, Hongxun; CrystEngComm 21 (2019) 6374–; doi:10.1039/C9CE01092K

data_7233984
_publ_section_title
;
 Thermodynamics and molecular mechanism of the formation of the cocrystals
 of p-hydroxybenzoic acid and glutaric acid
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              6374
_journal_paper_doi               10.1039/C9CE01092K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C7 H6 O3, C5 H8 O4'
_chemical_formula_sum            'C12 H14 O7'
_chemical_formula_weight         270.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-11 deposited with the CCDC.    2019-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.478(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6867(4)
_cell_length_b                   15.1019(6)
_cell_length_c                   9.9125(5)
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      28.6630
_cell_measurement_theta_min      2.5170
_cell_volume                     1253.22(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.844
_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    -41.00  62.00   0.50    4.84    --  -13.65  57.00   1.00  206
  2  \w     39.00  97.00   0.50    4.84    --   12.17 178.00-120.00  116
  3  \w     39.00  97.00   0.50    4.84    --   12.17 178.00-150.00  116
  4  \w    -89.00  14.00   0.50    4.84    --  -13.65 -57.00-140.00  206
  5  \w     36.00  68.00   0.50    4.84    --   12.17-178.00 -60.00   64
  6  \w    -95.00  19.00   0.50    4.84    --  -13.65 -37.00   0.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147769000
_diffrn_orient_matrix_UB_12      -0.0111082000
_diffrn_orient_matrix_UB_13      -0.0649284000
_diffrn_orient_matrix_UB_21      -0.0605037000
_diffrn_orient_matrix_UB_22      0.0299938000
_diffrn_orient_matrix_UB_23      -0.0348113000
_diffrn_orient_matrix_UB_31      0.0574875000
_diffrn_orient_matrix_UB_32      0.0343606000
_diffrn_orient_matrix_UB_33      0.0091498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13894
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.041
_diffrn_reflns_theta_min         2.523
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
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    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0781P)^2^+0.1653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2235
_reflns_number_total             3101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01092k2.cif
_cod_data_source_block           phba-glutaril
_cod_depositor_comments          'Adding full bibliography for 7233984.cif.'
_cod_database_code               7233984
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H3)=1-FVAR(1)
 Sof(H2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C6(H6), C3(H3A)
;
_shelx_res_checksum              47573
_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 1.861
_oxdiff_exptl_absorpt_empirical_full_min 0.537