Molecular simulation studies on the design of multicomponent sorbic acid crystals for tuning solubility
Li, Chang; Wu, Di; Gao, Zhenguo; Chen, Wei; CrystEngComm 25 (2023) 4889–4901; doi:10.1039/D3CE00392B

data_7247113
_publ_section_title
;
 Molecular simulation studies on the design of multicomponent sorbic acid
 crystals for tuning solubility
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4889
_journal_page_last               4901
_journal_paper_doi               10.1039/D3CE00392B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '2(C6 H7 O2), C4 H12 N2'
_chemical_formula_sum            'C16 H26 N2 O4'
_chemical_formula_weight         310.39
_chemical_name_common            'piperazine-1,4-diium di-sorbate'
_chemical_name_systematic        'piperazine-1,4-diium di-2e,4e-hexadienoicate'
_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             2020-11-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-25 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                108.023(13)
_cell_angle_beta                 94.575(12)
_cell_angle_gamma                99.275(13)
_cell_formula_units_Z            1
_cell_length_a                   5.6474(9)
_cell_length_b                   7.3558(11)
_cell_length_c                   10.9693(15)
_cell_measurement_reflns_used    2810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5170
_cell_measurement_theta_min      1.9250
_cell_volume                     423.55(12)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_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   2.00    2.00    --  -25.00  45.00   0.00   90
  2  \w   -115.00  65.00   2.00    2.00    --  -25.00  45.00  90.00   90
  3  \w   -115.00  65.00   2.00    2.00    --  -25.00  45.00 180.00   90
;
_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      -0.1129797000
_diffrn_orient_matrix_UB_12      0.0177895000
_diffrn_orient_matrix_UB_13      -0.0217535000
_diffrn_orient_matrix_UB_21      -0.0175894000
_diffrn_orient_matrix_UB_22      -0.0872751000
_diffrn_orient_matrix_UB_23      -0.0534627000
_diffrn_orient_matrix_UB_31      -0.0586247000
_diffrn_orient_matrix_UB_32      -0.0525385000
_diffrn_orient_matrix_UB_33      0.0371786000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4493
_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         26.370
_diffrn_reflns_theta_min         1.971
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87305
_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            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ??'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.100(12)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0494P)^2^+0.1067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1413
_reflns_number_total             1731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00392b2.cif
_cod_data_source_block           r20200811b
_cod_depositor_comments
'Adding full bibliography for 7247113--7247115.cif.'
_cod_original_cell_volume        423.55(11)
_cod_database_code               7247113
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1A-N1
 0.92 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C2(H2), C5(H5)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              94987
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.669