Hydrogen-bonded supramolecular motifs in pyrimethaminium 4-methylbenzoate, pyrimethaminium 3-hydroxypicolinate and pyrimethaminium 2,4-dichlorobenzoate
Thanigaimani, Kaliyaperumal; Muthiah, Packianathan Thomas; Acta Crystallographica Section C 66 (2010) o104–o108; doi:10.1107/S0108270110002337

data_2017558
_publ_section_title
;
 Hydrogen-bonded supramolecular motifs in pyrimethaminium
 4-methylbenzoate, pyrimethaminium 3-hydroxypicolinate and
 pyrimethaminium 2,4-dichlorobenzoate
;
_journal_coeditor_code           GA3142
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o104
_journal_page_last               o108
_journal_paper_doi               10.1107/S0108270110002337
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H14 Cl N4 + , C7 H3 Cl2 O2 -'
_chemical_formula_moiety         'C12 H14 Cl N4 + , C7 H3 Cl2 O2 -'
_chemical_formula_sum            'C19 H17 Cl3 N4 O2'
_chemical_formula_weight         439.72
_chemical_name_common            'Pyrimethaminium 2,4-dichlorobenzoate'
_chemical_name_systematic
;
2,4-diamino-(4-chlorophenyl)-6-ethylpyrimidinium 2,4-dichlorobenzoate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3808(2)
_cell_length_b                   12.6799(2)
_cell_length_c                   22.4021(3)
_cell_measurement_reflns_used    5639
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.4
_cell_measurement_theta_min      1.8
_cell_volume                     4084.96(10)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26496
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        29.42
_diffrn_reflns_theta_max         29.42
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.514
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression 'Fc^*^ = kFc[1+0.001Fc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0442P)^2^+1.8433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                3791
_reflns_number_total             5639
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ga3142.cif
_cod_data_source_block           III
_cod_database_code               2017558
_cod_database_fobs_code          2017558