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_2021073
_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 +, C5 H Cl2 O2 S -'
_chemical_formula_moiety         'C12 H14 Cl N4 +, C5 H Cl2 O2 S -'
_chemical_formula_sum            'C17 H15 Cl3 N4 O2 S'
_chemical_formula_weight         445.74
_chemical_name_common
;
Pyrimethaminium 2,5-dichlorothiophene-3-carboxylate
;
_chemical_name_systematic
;
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium
2,5-dichlorothiophene-3-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                63.919(7)
_cell_angle_beta                 85.243(5)
_cell_angle_gamma                83.689(5)
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_cell_length_a                   9.3415(5)
_cell_length_b                   10.2751(6)
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_cell_measurement_theta_max      30.0600
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_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
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PLATON (Spek, 2009), Mercury (Macrae <i>et al.</i>, 2008) and
<i>POV-RAY for Windows</i> (Cason, 2004)
;
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PLATON (Spek, 2009)
;
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SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
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SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
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;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_method       '\w scans'
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_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.909
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colorless
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_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.150
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_refine_diff_density_min         -0.617
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0758P)^2^+0.5521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     'I > 2\s(I)'
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_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.916
_shelx_res_checksum              56184