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_2021072
_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 +, C15 H9 O2 -, 1.5(H2 O)'
_chemical_formula_moiety         'C14 H19 N4 O3 +, C15 H9 O2 -, 1.5(H2 O)'
_chemical_formula_sum            'C29 H31 N4 O6.5'
_chemical_formula_weight         539.57
_chemical_name_common
;
Trimethoprimium anthracene-9-carboxylate sesquihydrate
;
_chemical_name_systematic
;
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium anthracene-9-carboxylate
sesquihydrate
;
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                106.203(3)
_cell_angle_beta                 101.386(3)
_cell_angle_gamma                90.029(3)
_cell_formula_units_Z            4
_cell_length_a                   11.1680(5)
_cell_length_b                   16.1913(5)
_cell_length_c                   16.2434(5)
_cell_measurement_reflns_used    6949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2890
_cell_measurement_theta_min      3.2100
_cell_volume                     2760.20(18)
_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_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  0.0347
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29344
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.924
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       prism
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         12640
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0784P)^2^+0.7983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1888
_reflns_number_gt                7531
_reflns_number_total             12640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3126sup1.cif
_cod_data_source_block           V
_cod_depositor_comments
;

2019-09-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H19 N4 O3 +), 2(C15 H9 O2 -), 3(H2 O)'
_cod_original_formula_iupac      '2C14 H19 N4 O3 +, 2C15 H9 O2 -, 3(H2 O)'
_cod_original_formula_sum        'C58 H62 N8 O13'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1079.15
_cod_database_code               2021072
_cod_database_fobs_code          2021072
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              3403