Enhancing the dissolution and bacteriostatic activity of trimethoprim through salt formation
Hu, Xingchen; Xiao, Yuntian; Qi, Luguang; Bai, Yunhe; Sun, Ying; Ye, Yang; Xie, Chuang; CrystEngComm 25 (2023) 3445–3459; doi:10.1039/D3CE00128H

data_7246785
_publ_section_title
;
 Enhancing the dissolution and bacteriostatic activity of trimethoprim
 through salt formation
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              3445
_journal_page_last               3459
_journal_paper_doi               10.1039/D3CE00128H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O5, 2(C H4 O)'
_chemical_formula_sum            'C23 H32 N4 O10'
_chemical_formula_weight         524.52
_chemical_name_systematic        TMP-GA-2MeOH
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-22 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.535(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2636(10)
_cell_length_b                   20.7045(13)
_cell_length_c                   12.0759(11)
_cell_measurement_reflns_used    6758
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.0010
_cell_measurement_theta_min      1.9630
_cell_volume                     2497.2(4)
_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 1.5 (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_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -120.00  60.00   1.00    2.00    --  -30.00  45.00   0.00  180
  2  \w   -120.00  30.00   1.00    2.00    --  -30.00  45.00  90.00  150
  3  \w   -120.00   0.00   1.00    2.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0099420000
_diffrn_orient_matrix_UB_12      0.0222879000
_diffrn_orient_matrix_UB_13      0.0481536000
_diffrn_orient_matrix_UB_21      0.0244699000
_diffrn_orient_matrix_UB_22      0.0231120000
_diffrn_orient_matrix_UB_23      -0.0277822000
_diffrn_orient_matrix_UB_31      -0.0659201000
_diffrn_orient_matrix_UB_32      0.0119267000
_diffrn_orient_matrix_UB_33      -0.0360106000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19767
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.967
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0059(9)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0570P)^2^+0.6353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3552
_reflns_number_total             5092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00128h2.cif
_cod_data_source_block           r20220721c
_cod_depositor_comments
'Adding full bibliography for 7246781--7246785.cif.'
_cod_database_code               7246785
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C8(H8), C12(H12), C17(H17), C21(H21)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2C,H2D,H2E), C3(H3A,H3B,H3C), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6A), O7(H7), O8(H8A), O9(H9), O10(H10)
;
_shelx_res_checksum              16988
_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 1.732
_oxdiff_exptl_absorpt_empirical_full_min 0.690