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_2021069
_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          'C14 H19 N4 O3 +, C5 H2 Br O2 S -, H2 O'
_chemical_formula_moiety         'C14 H19 N4 O3 +, C5 H2 Br O2 S -, H2 O'
_chemical_formula_sum            'C19 H23 Br N4 O6 S'
_chemical_formula_weight         515.38
_chemical_name_common
;
Trimethoprimium 3-bromothiophene-2-carboxylate monohydrate
;
_chemical_name_systematic
;
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium
3-bromothiophene-2-carboxylate monohydrate
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.773(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9440(8)
_cell_length_b                   6.8991(3)
_cell_length_c                   19.7206(14)
_cell_measurement_reflns_used    4168
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5380
_cell_measurement_theta_min      3.2590
_cell_volume                     2169.4(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.947
_refine_diff_density_min         -1.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0414P)^2^+1.5827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                3766
_reflns_number_total             4949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3126sup1.cif
_cod_data_source_block           II
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_shelx_estimated_absorpt_t_min   0.375
_shelx_estimated_absorpt_t_max   0.497
_shelx_res_checksum              23514
_cod_database_fobs_code 2021069