Theoretical and experimental study of pharmaceutical salts: a case of trimethoprim
Zhang, Liang; Wu, Di; Zhang, Menglong; Yu, Fuhai; Bao, Ying; Xie, Chuang; Hou, Baohong; Jing, Dingding; Zhang, Chuntao; Chen, Wei; CrystEngComm 26 (2024) 3808–3822; doi:10.1039/D4CE00345D

data_7248803
_publ_section_title
;
 Theoretical and experimental study of pharmaceutical salts: a case of
 trimethoprim
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              3808
_journal_page_last               3822
_journal_paper_doi               10.1039/D4CE00345D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C6 H3 O5, C14 H19 N4 O3'
_chemical_formula_sum            'C20 H22 N4 O8'
_chemical_formula_weight         446.41
_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     iterative
_audit_creation_date             2024-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-19 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                63.782(3)
_cell_angle_beta                 64.481(2)
_cell_angle_gamma                84.746(2)
_cell_formula_units_Z            8
_cell_length_a                   16.9699(4)
_cell_length_b                   17.1267(5)
_cell_length_c                   17.9029(3)
_cell_measurement_reflns_used    28644
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.7140
_cell_measurement_theta_min      1.9940
_cell_volume                     4181.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -110.00  70.00   0.50    2.00    --  -20.00   0.00   0.00  360
  2  \w   -110.00  70.00   0.50    2.00    --  -20.00   0.00  90.00  360
  3  \w   -110.00   7.00   0.50    2.00    --  -20.00 -70.00 180.00  234
  4  \w   -110.00   7.00   0.50    2.00    --  -20.00 -70.00   0.00  234
  5  \w   -110.00   6.00   0.50    2.00    --  -20.00 -70.00  90.00  232
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku MM007 Saturn944+'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0370526000
_diffrn_orient_matrix_UB_12      0.0232167000
_diffrn_orient_matrix_UB_13      0.0015734000
_diffrn_orient_matrix_UB_21      0.0281487000
_diffrn_orient_matrix_UB_22      0.0402416000
_diffrn_orient_matrix_UB_23      -0.0285129000
_diffrn_orient_matrix_UB_31      0.0035100000
_diffrn_orient_matrix_UB_32      -0.0022161000
_diffrn_orient_matrix_UB_33      -0.0399386000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17016
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.772
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1262
_refine_ls_number_reflns         17016
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0835P)^2^+1.3979P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13143
_reflns_number_total             17016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00345d2.cif
_cod_data_source_block           r20230615c_autored
_cod_depositor_comments
'Adding full bibliography for 7248797--7248804.cif.'
_cod_database_code               7248803
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5619(15)
 0.4381(15)
2. 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
3. Restrained distances
 O24-H24
 0.85 with sigma of 0.01
 O29-H29
 0.85 with sigma of 0.01
 O4-H4c
 0.85 with sigma of 0.01
 O9-H9a
 0.85 with sigma of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C50(H50a,H50b), C10(H10c,H10d), C36(H36a,H36b), C76(H76a,H76b)
4.b Aromatic/amide H refined with riding coordinates:
 C57(H57), C58(H58), C44(H44), C52(H52), C48(H48), C24(H24a), C23(H23),
 C64(H64), C63(H63), C12(H12), C4(H4), C8(H8), C17(H17), C18(H18), C38(H38),
 C34(H34), C30(H30), C74(H74), C70(H70), C80(H80)
4.c Idealised Me refined as rotating group:
 C41(H41a,H41b,H41c), C42(H42a,H42b,H42c), C43(H43a,H43b,H43c), C2(H2c,H2d,
 H2e), C1(H1a,H1b,H1c), C3(H3a,H3b,H3c), C28(H28a,H28b,H28c), C27(H27a,H27b,
 H27c), C29(H29a,H29b,H29c), C68(H68a,H68b,H68c), C69(H69a,H69b,H69c), C67(H67a,
 H67b,H67c)
;
_shelx_res_checksum              69619
_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 1.878
_oxdiff_exptl_absorpt_empirical_full_min 0.562