A single crystal to single crystal solvatomorphic phase transition in cocrystals of pyrimethamine with 4-hydroxybenzoic acid. An experimental and theoretical study
Bilal, Aqsa; Mehmood, Arshad; Noureen, Sajida; Ahmed, Maqsood; CrystEngComm 27 (2025) 4722–4733; doi:10.1039/D5CE00243E

data_7250472
_publ_section_title
;
 A single crystal to single crystal solvatomorphic phase transition in
 cocrystals of pyrimethamine with 4-hydroxybenzoic acid. An experimental
 and theoretical study
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              4722
_journal_page_last               4733
_journal_paper_doi               10.1039/D5CE00243E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C12 H14 Cl N4, C7 H5 O3, H2 O'
_chemical_formula_sum            'C19 H21 Cl N4 O4'
_chemical_formula_weight         404.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-12-28
_audit_creation_method
;FinalCif V126 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-05-08 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.994(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4563(6)
_cell_length_b                   14.2010(6)
_cell_length_c                   16.4360(8)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.18
_cell_volume                     3803.7(3)
_computing_cell_refinement       'SAINT V8.40B (2016)'
_computing_data_collection
'Bruker BIS V6.2.16/2021-10-23 and APEX4 2022.1-1'
_computing_data_reduction        'SAINT V8.40B (2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'Glass needle'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24711
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.179
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0322P)^2^+4.4713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2929
_reflns_number_total             3892
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {20711e88-f6f5-41a7-94c1-7e6f56cf14e6}
_cod_data_source_file            d5ce00243e2.cif
_cod_data_source_block           IAM_Shelx
_cod_depositor_comments
'Adding full bibliography for 7250470--7250473.cif.'
_cod_database_code               7250472
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.979
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cobra Cryo device'
_shelx_res_checksum              93348
_publcif_funding_html
;
;