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_7248804
_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         '2(C5 H3 O3 S), C14 H20 N4 O3, 2(C H4 O)'
_chemical_formula_sum            'C26 H34 N4 O11 S2'
_chemical_formula_weight         642.69
_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                83.4930(10)
_cell_angle_beta                 68.6770(10)
_cell_angle_gamma                61.8010(10)
_cell_formula_units_Z            2
_cell_length_a                   11.43180(10)
_cell_length_b                   11.93110(10)
_cell_length_c                   12.8427(2)
_cell_measurement_reflns_used    18251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.7140
_cell_measurement_theta_min      1.9340
_cell_volume                     1434.43(3)
_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  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.902
_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    0.50    --  -20.00   0.00  90.00  360
  2  \w   -110.00  55.00   0.50    0.50    --  -20.00   0.00   0.00  330
  3  \w   -110.00   7.00   0.50    0.50    --  -20.00 -70.00 180.00  234
  4  \w   -110.00   7.00   0.50    0.50    --  -20.00 -70.00   0.00  234
  5  \w   -110.00   7.00   0.50    0.50    --  -20.00 -70.00  90.00  234
;
_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      0.0146490000
_diffrn_orient_matrix_UB_12      -0.0630211000
_diffrn_orient_matrix_UB_13      -0.0114315000
_diffrn_orient_matrix_UB_21      -0.0729728000
_diffrn_orient_matrix_UB_22      0.0216485000
_diffrn_orient_matrix_UB_23      0.0105408000
_diffrn_orient_matrix_UB_31      0.0112931000
_diffrn_orient_matrix_UB_32      0.0115423000
_diffrn_orient_matrix_UB_33      -0.0573697000
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37718
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.708
_diffrn_reflns_theta_min         1.942
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         11154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0543P)^2^+0.5913P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9199
_reflns_number_total             11154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00345d2.cif
_cod_data_source_block           r20230324d_autored
_cod_depositor_comments
'Adding full bibliography for 7248797--7248804.cif.'
_cod_database_code               7248804
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.49
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C20(H20), C17(H17), C23(H23), C9(H9), C15(H15), C24(H24),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C3(H3C,H3D,H3E), C2(H2A,H2B,H2C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              95376
_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.721