Spectroscopic investigations of a pharmaceutical solid form analogue: pyrimethanil L-tartrate hemi-cocrystal
Dosanjh, Ramandeep; Patterson, Adam; Harris, Joe; Wilson, Claire; Gutmann, Matthias J.; Collier, Paul; Hyde, Tim; Johnson, Timothy; York, Andy; Parker, Stewart F.; Lennon, David; Physical Chemistry Chemical Physics  (2025) –; doi:10.1039/D5CP02802G

data_7251235
_publ_section_title
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 Spectroscopic investigations of a pharmaceutical solid form analogue:
 pyrimethanil L-tartrate hemi-cocrystal
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_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP02802G
_journal_year                    2025
_chemical_formula_moiety         '4(C28 H32 N6 O6)'
_chemical_formula_sum            'C112 H128 N24 O24'
_chemical_formula_weight         2194.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2024-06-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
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2024-09-19 deposited with the CCDC.	2025-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   18.791(3)
_cell_length_b                   16.407(2)
_cell_length_c                   8.6453(15)
_cell_measurement_temperature    283.15
_cell_volume                     2665.4(7)
_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)'
_diffrn_ambient_temperature      283.15
_diffrn_measured_fraction_theta_full 0.667
_diffrn_measured_fraction_theta_max 0.160
_diffrn_radiation_type           neutrons
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 0.667
_diffrn_reflns_Laue_measured_fraction_max 0.160
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18634
_diffrn_reflns_point_group_measured_fraction_full 0.634
_diffrn_reflns_point_group_measured_fraction_max 0.133
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         88.133
_diffrn_reflns_theta_min         8.926
_exptl_absorpt_coefficient_mu    0.045
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_refine_diff_density_max         3.904
_refine_diff_density_min         -1.944
_refine_diff_density_rms         0.446
_refine_ls_abs_structure_details
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_extinction_coef       0.00013(2)
_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   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         18634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0957
_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^)+(0.1688P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2279
_refine_ls_wR_factor_ref         0.2343
_reflns_Friedel_coverage         0.553
_reflns_Friedel_fraction_full    0.590
_reflns_Friedel_fraction_max     0.102
_reflns_number_gt                17642
_reflns_number_total             18634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp02802g2.cif
_cod_data_source_block           pyrimethanilhemicocrystal_10k_sxd
_cod_database_code               7251235
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -37.2(4)
 3.45(11) 0.76(4) 2.84(9) 0.72(3) 2.59(9) 0.95(4) 3.15(10) 1.08(4) 3.25(11)
 4.71(15) 3.24(11) 2.42(8) 4.16(13) 4.89(16)
2. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O2A)
Uanis(O1B) = Uanis(O2B)
Uiso(O3A) = Uiso(O3AB)
Uiso(H3AA) = Uiso(H3AB)
Uiso(H14A) = Uiso(H14B)
Uanis(C13A) = Uanis(C14A)
Uanis(C13B) = Uanis(C14B)
Uanis(N1A) = Uanis(N2A) = Uanis(N3A)
Uanis(N1B) = Uanis(N2B) = Uanis(N3B)
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A)
Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B) = Uanis(C6B)
Uanis(C7A) = Uanis(C8A) = Uanis(C9A) = Uanis(C10A) = Uanis(C11A) = Uanis(C12A)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B) = Uanis(C10B) = Uanis(C11B) = Uanis(C12B)
3. Others
 Sof(O3AB)=Sof(H3AB)=Sof(H14B)=1-FVAR(1)
 Sof(O3A)=Sof(H3AA)=Sof(H14A)=FVAR(1)
 Sof(H2B)=1-FVAR(2)
 Sof(H1B)=FVAR(2)
 Fixed Sof: H2A(0.5) H2AA(0.5)
;
_shelx_res_checksum              77263
_olex2_submission_special_instructions 'No special instructions were received'