##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2012-06-19
_journal_date_accepted     2012-06-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     o2235
_journal_page_last     o2235
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812028401
_journal_coeditor_code     XU5569
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
6-Amino-4-(3-iodoanilino)-2-methylpyrimidin-1-ium chloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Zaghary, Wafaa A.'
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
Riyadh 11451
Saudi Arabia
;
    'Geffken, Detlef'
;
Institut für Pharmazie
Bundesstrasse 45 20146
Hamburg
Germany
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
     Chemistry Department
     Faculty of Science
     King Abdulaziz University
     PO Box 80203 Jeddah
     Saudi Arabia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6-Amino-4-(3-iodoanilino)-2-methylpyrimidin-1-ium chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H12 I N4 +, Cl -'
_chemical_formula_sum     'C11 H12 Cl I N4'
_chemical_formula_iupac     'C11 H12 I N4 +, Cl -'
_chemical_formula_weight     362.60
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n n 2'
_symmetry_space_group_name_Hall     'P 2 -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     12.6323(5)
_cell_length_b     19.8608(7)
_cell_length_c     5.1267(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1286.23(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5603
_cell_measurement_theta_min     2.6037
_cell_measurement_theta_max     27.4978
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.872
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     2.681
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2012)'
_exptl_absorpt_correction_T_min     0.5538
_exptl_absorpt_correction_T_max     0.9239
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                  'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     10009
_diffrn_reflns_av_R_equivalents     0.0356
_diffrn_reflns_av_sigmaI/netI     0.0377
_diffrn_reflns_theta_min     2.61
_diffrn_reflns_theta_max     27.56
_diffrn_reflns_theta_full     27.56
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -6
_diffrn_reflns_limit_l_max     6
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2981
_reflns_number_gt     2833
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0350
_refine_ls_R_factor_gt     0.0318
_refine_ls_wR_factor_gt     0.0752
_refine_ls_wR_factor_ref     0.0777
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     2981
_refine_ls_number_parameters     172
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0455P)²+0.0980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.512
_refine_diff_density_min     -0.698
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1321 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.04(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.859538(17) 0.859281(10) 0.49964(10) 0.01803(9) Uani d . 1 1 . .
    Cl Cl1 0.5000 0.5000 0.7100(3) 0.0165(3) Uani d S 1 2 . .
    Cl Cl2 1.0000 0.5000 1.8561(3) 0.0189(3) Uani d S 1 2 . .
    N N1 0.6726(3) 0.62226(17) 0.8346(7) 0.0133(7) Uani d D 1 1 . .
    H H1 0.616(3) 0.597(2) 0.815(12) 0.030(15) Uiso d D 1 1 . .
    N N2 0.8301(3) 0.63625(14) 1.0653(6) 0.0115(8) Uani d . 1 1 . .
    N N3 0.8681(3) 0.56332(17) 1.4102(7) 0.0127(7) Uani d D 1 1 . .
    H H3 0.911(4) 0.551(2) 1.537(8) 0.032(14) Uiso d D 1 1 . .
    N N4 0.7588(3) 0.47680(17) 1.5483(7) 0.0158(8) Uani d D 1 1 . .
    H H4A 0.809(3) 0.471(2) 1.667(7) 0.019(12) Uiso d D 1 1 . .
    H H4B 0.6921(14) 0.465(2) 1.559(12) 0.037(16) Uiso d D 1 1 . .
    C C1 0.7485(3) 0.78043(16) 0.4921(11) 0.0132(7) Uani d . 1 1 . .
    C C2 0.6725(3) 0.7825(2) 0.2979(8) 0.0153(8) Uani d . 1 1 . .
    H H2 0.6724 0.8175 0.1716 0.018 Uiso calc R 1 1 . .
    C C3 0.5960(3) 0.7318(2) 0.2927(8) 0.0174(9) Uani d . 1 1 . .
    H H3A 0.5418 0.7328 0.1644 0.021 Uiso calc R 1 1 . .
    C C4 0.5988(3) 0.68030(16) 0.4730(9) 0.0138(8) Uani d . 1 1 . .
    H H4 0.5464 0.6460 0.4668 0.017 Uiso calc R 1 1 . .
    C C5 0.6770(3) 0.67774(17) 0.6634(8) 0.0116(7) Uani d . 1 1 . .
    C C6 0.7534(3) 0.72929(18) 0.6783(9) 0.0141(8) Uani d . 1 1 . .
    H H6 0.8062 0.7292 0.8101 0.017 Uiso calc R 1 1 . .
    C C7 0.7378(3) 0.60225(16) 1.0287(9) 0.0116(8) Uani d . 1 1 . .
    C C8 0.7081(3) 0.54705(17) 1.1824(8) 0.0126(7) Uani d . 1 1 . .
    H H8 0.6438 0.5235 1.1515 0.015 Uiso calc R 1 1 . .
    C C9 0.7757(3) 0.52821(18) 1.3798(8) 0.0121(8) Uani d . 1 1 . .
    C C10 0.8926(3) 0.61518(19) 1.2527(8) 0.0110(7) Uani d . 1 1 . .
    C C11 0.9960(4) 0.64830(19) 1.3029(9) 0.0190(9) Uani d . 1 1 . .
    H H11A 0.9953 0.6938 1.2292 0.029 Uiso calc R 1 1 . .
    H H11B 1.0528 0.6221 1.2212 0.029 Uiso calc R 1 1 . .
    H H11C 1.0083 0.6509 1.4914 0.029 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    I1 0.01513(14) 0.01341(13) 0.02556(15) -0.00259(7) -0.00545(16) 0.00610(14)
    Cl1 0.0112(6) 0.0149(6) 0.0234(8) -0.0017(5) 0.000 0.000
    Cl2 0.0187(7) 0.0262(7) 0.0117(7) 0.0092(5) 0.000 0.000
    N1 0.0139(17) 0.0138(14) 0.0122(16) -0.0050(14) -0.0026(14) 0.0015(14)
    N2 0.0101(16) 0.0122(14) 0.012(2) -0.0018(11) -0.0021(13) 0.0017(11)
    N3 0.0130(18) 0.0130(15) 0.0121(16) 0.0006(12) -0.0030(13) 0.0017(13)
    N4 0.0135(16) 0.0214(15) 0.012(2) -0.0011(12) -0.0009(14) 0.0067(14)
    C1 0.0133(16) 0.0117(14) 0.0146(16) 0.0003(12) 0.003(2) 0.002(2)
    C2 0.014(2) 0.0166(18) 0.015(2) 0.0006(16) -0.0014(17) 0.0031(16)
    C3 0.016(2) 0.0180(18) 0.018(2) 0.0008(16) -0.0055(17) 0.0016(17)
    C4 0.0132(16) 0.0123(14) 0.016(2) 0.0005(12) 0.000(2) -0.0008(18)
    C5 0.0115(18) 0.0116(16) 0.0118(18) 0.0008(14) 0.0002(16) 0.0019(16)
    C6 0.0126(19) 0.0157(17) 0.0139(17) 0.0002(14) -0.0026(16) -0.0006(16)
    C7 0.0101(16) 0.0120(14) 0.013(2) 0.0001(11) -0.0003(17) -0.0014(17)
    C8 0.0117(19) 0.0122(16) 0.0139(18) -0.0014(14) -0.0001(16) 0.0026(16)
    C9 0.016(2) 0.0103(15) 0.0099(18) -0.0011(14) 0.0015(15) -0.0004(14)
    C10 0.0123(19) 0.0121(18) 0.0085(17) 0.0006(15) 0.0004(15) 0.0006(15)
    C11 0.016(2) 0.022(2) 0.020(2) -0.0062(16) -0.0060(18) 0.0083(17)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C1 . 2.103(3) ?
    N1 C7 . 1.351(5) ?
    N1 C5 . 1.410(5) ?
    N1 H1 . 0.880(10)
                    ?
    N2 C10 . 1.313(5) ?
    N2 C7 . 1.360(5) ?
    N3 C10 . 1.345(5) ?
    N3 C9 . 1.369(5) ?
    N3 H3 . 0.880(10)
                    ?
    N4 C9 . 1.354(5) ?
    N4 H4A . 0.880(10)
                     ?
    N4 H4B . 0.880(10)
                     ?
    C1 C2 . 1.384(6) ?
    C1 C6 . 1.395(6) ?
    C2 C3 . 1.396(6) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.380(6) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.390(6) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.409(5) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.401(5) ?
    C8 C9 . 1.375(5) ?
    C8 H8 . 0.9500 ?
    C10 C11 . 1.485(6) ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7 N1 C5 . . 131.6(3) ?
    C7 N1 H1 . . 114(4) ?
    C5 N1 H1 . . 114(4) ?
    C10 N2 C7 . . 117.3(3) ?
    C10 N3 C9 . . 121.2(3) ?
    C10 N3 H3 . . 122(3) ?
    C9 N3 H3 . . 117(3) ?
    C9 N4 H4A . . 115(3) ?
    C9 N4 H4B . . 113(4) ?
    H4A N4 H4B . . 128(5) ?
    C2 C1 C6 . . 123.0(3) ?
    C2 C1 I1 . . 117.0(3) ?
    C6 C1 I1 . . 120.0(3) ?
    C1 C2 C3 . . 118.2(4) ?
    C1 C2 H2 . . 120.9 ?
    C3 C2 H2 . . 120.9 ?
    C4 C3 C2 . . 120.3(4) ?
    C4 C3 H3A . . 119.8 ?
    C2 C3 H3A . . 119.8 ?
    C3 C4 C5 . . 121.1(3) ?
    C3 C4 H4 . . 119.5 ?
    C5 C4 H4 . . 119.5 ?
    C4 C5 C6 . . 119.9(4) ?
    C4 C5 N1 . . 116.0(3) ?
    C6 C5 N1 . . 124.1(4) ?
    C1 C6 C5 . . 117.5(4) ?
    C1 C6 H6 . . 121.2 ?
    C5 C6 H6 . . 121.2 ?
    N1 C7 N2 . . 118.5(3) ?
    N1 C7 C8 . . 118.8(3) ?
    N2 C7 C8 . . 122.7(4) ?
    C9 C8 C7 . . 117.4(4) ?
    C9 C8 H8 . . 121.3 ?
    C7 C8 H8 . . 121.3 ?
    N4 C9 N3 . . 116.5(3) ?
    N4 C9 C8 . . 125.2(4) ?
    N3 C9 C8 . . 118.3(4) ?
    N2 C10 N3 . . 123.0(4) ?
    N2 C10 C11 . . 121.0(4) ?
    N3 C10 C11 . . 116.0(4) ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 1.5(7) ?
    I1 C1 C2 C3 . . . . -178.2(3) ?
    C1 C2 C3 C4 . . . . -1.8(6) ?
    C2 C3 C4 C5 . . . . 0.3(7) ?
    C3 C4 C5 C6 . . . . 1.6(6) ?
    C3 C4 C5 N1 . . . . -179.2(4) ?
    C7 N1 C5 C4 . . . . 175.8(4) ?
    C7 N1 C5 C6 . . . . -5.0(7) ?
    C2 C1 C6 C5 . . . . 0.4(7) ?
    I1 C1 C6 C5 . . . . -179.9(3) ?
    C4 C5 C6 C1 . . . . -1.9(6) ?
    N1 C5 C6 C1 . . . . 179.0(4) ?
    C5 N1 C7 N2 . . . . -5.8(6) ?
    C5 N1 C7 C8 . . . . 174.7(4) ?
    C10 N2 C7 N1 . . . . -179.0(4) ?
    C10 N2 C7 C8 . . . . 0.4(6) ?
    N1 C7 C8 C9 . . . . -179.5(4) ?
    N2 C7 C8 C9 . . . . 1.1(6) ?
    C10 N3 C9 N4 . . . . 179.8(4) ?
    C10 N3 C9 C8 . . . . 0.3(6) ?
    C7 C8 C9 N4 . . . . 179.1(4) ?
    C7 C8 C9 N3 . . . . -1.4(6) ?
    C7 N2 C10 N3 . . . . -1.6(6) ?
    C7 N2 C10 C11 . . . . 178.6(4) ?
    C9 N3 C10 N2 . . . . 1.3(6) ?
    C9 N3 C10 C11 . . . . -178.9(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 Cl1 . 0.88(4) 2.48(4) 3.325(4) 162(4)
    N3 H3 Cl2 . 0.88(5) 2.23(4) 3.096(4) 168(4)
    N4 H4A Cl2 . 0.89(4) 2.66(4) 3.462(4) 150(3)
    N4 H4B Cl1 1_556 0.88(2) 2.64(3) 3.404(4) 146(4)
