Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine
Swinton Darious, Robert; Thomas Muthiah, Packianathan; Perdih, Franc; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618004072

data_2021075
_publ_section_title
;
 Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs
 trimethoprim and pyrimethamine
;
_journal_coeditor_code           CU3126
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618004072
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C12 H14 Cl N4 +, C15 H9 O2 -, C2 H6 O, H2 O'
_chemical_formula_moiety         'C12 H14 Cl N4 +, C15 H9 O2 -, C2 H6 O, H2 O'
_chemical_formula_sum            'C29 H31 Cl N4 O4'
_chemical_formula_weight         535.03
_chemical_name_common
;
Pyrimethaminium anthracene-9-carboxylate ethanol monosolvate monohydrate
;
_chemical_name_systematic
;
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium anthracene-9-carboxylate
methanol monosolvate monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.293(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5195(5)
_cell_length_b                   15.7842(11)
_cell_length_c                   18.8336(8)
_cell_measurement_reflns_used    3464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3210
_cell_measurement_theta_min      3.4880
_cell_volume                     2827.6(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009), Mercury (Macrae <i>et al.</i>, 2008) and
<i>POV-RAY for Windows</i> (Cason, 2004)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15577
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.251
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL2014 (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6466
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0651P)^2^+0.1856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                3240
_reflns_number_total             6466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3126sup1.cif
_cod_data_source_block           VIII
_cod_database_code               2021075
_cod_database_fobs_code          2021075
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              95465