#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230418.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230418
loop_
_publ_author_name
'Tabatabaee, Masoumeh'
'Noozari, Najmeh'
_publ_section_title
;
 2-Aminopyrimidin-1-ium 4-methylbenzenesulfonate
;
_journal_coeditor_code           LH5246
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1457
_journal_paper_doi               10.1107/S1600536811018198
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C4 H6 N3 +, C7 H7 O3 S -'
_chemical_formula_moiety         'C4 H6 N3 +, C7 H7 O3 S -'
_chemical_formula_sum            'C11 H13 N3 O3 S'
_chemical_formula_weight         267.30
_chemical_name_systematic
;
2-Aminopyrimidin-1-ium 4-methylbenzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2567(3)
_cell_length_b                   13.3756(6)
_cell_length_c                   15.2512(7)
_cell_measurement_reflns_used    5926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.58
_cell_measurement_theta_min      2.72
_cell_volume                     1251.43(10)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12275
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0322
_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/[σ²(Fo²)+(0.0496P)²+0.3689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                3160
_reflns_number_total             3617
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5246.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230418
_cod_database_fobs_code          2230418
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S S1 0.28924(4) 0.172328(19) 0.105904(16) 0.01392(8) Uani d . 1 1 . .
O O1 0.28421(13) 0.21695(6) 0.19437(5) 0.01877(17) Uani d . 1 1 . .
O O2 0.51293(13) 0.15402(6) 0.09590(5) 0.01855(16) Uani d . 1 1 . .
O O3 0.14528(13) 0.08711(6) 0.08830(5) 0.01966(17) Uani d . 1 1 . .
C C1 0.18525(17) 0.26582(8) 0.02687(7) 0.01501(19) Uani d . 1 1 . .
C C2 -0.03778(18) 0.27159(8) -0.00789(7) 0.0183(2) Uani d . 1 1 . .
H H2A -0.1349 0.2244 0.0096 0.022 Uiso calc R 1 1 . .
C C3 -0.1167(2) 0.34700(9) -0.06827(8) 0.0220(2) Uani d . 1 1 . .
H H3A -0.2687 0.3509 -0.0919 0.026 Uiso calc R 1 1 . .
C C4 0.0232(2) 0.41735(9) -0.09488(8) 0.0236(2) Uani d . 1 1 . .
C C5 0.2456(2) 0.41027(9) -0.05918(8) 0.0254(2) Uani d . 1 1 . .
H H5A 0.3429 0.4576 -0.0764 0.031 Uiso calc R 1 1 . .
C C6 0.3277(2) 0.33500(9) 0.00123(8) 0.0213(2) Uani d . 1 1 . .
H H6A 0.4797 0.3309 0.0248 0.026 Uiso calc R 1 1 . .
C C7 -0.0643(3) 0.49831(10) -0.16093(9) 0.0348(3) Uani d . 1 1 . .
H H7A -0.1992 0.4752 -0.1997 0.052 Uiso calc PR 0.50 1 . .
H H7B 0.0438 0.5140 -0.1975 0.052 Uiso calc PR 0.50 1 . .
H H7C -0.0944 0.5584 -0.1286 0.052 Uiso calc PR 0.50 1 . .
H H7D 0.0326 0.5565 -0.1508 0.052 Uiso calc PR 0.50 1 . .
H H7E -0.2103 0.5178 -0.1530 0.052 Uiso calc PR 0.50 1 . .
H H7F -0.0721 0.4734 -0.2219 0.052 Uiso calc PR 0.50 1 . .
N N1 0.61962(15) 0.31572(7) 0.29233(6) 0.01640(18) Uani d . 1 1 . .
H H1A 0.5121 0.2804 0.2612 0.020 Uiso calc R 1 1 . .
N N2 0.99877(15) 0.33985(7) 0.33945(6) 0.01665(18) Uani d . 1 1 . .
N N3 0.86604(16) 0.21369(8) 0.23970(7) 0.0210(2) Uani d . 1 1 . .
H H3B 1.0008 0.1961 0.2382 0.025 Uiso calc R 1 1 . .
H H3C 0.7560 0.1808 0.2076 0.025 Uiso calc R 1 1 . .
C C8 0.82865(17) 0.29000(8) 0.29050(7) 0.0154(2) Uani d . 1 1 . .
C C9 0.57354(18) 0.39454(8) 0.34102(7) 0.0177(2) Uani d . 1 1 . .
H H9A 0.4264 0.4116 0.3415 0.021 Uiso calc R 1 1 . .
C C10 0.73953(18) 0.44934(8) 0.38933(7) 0.0179(2) Uani d . 1 1 . .
H H10A 0.7132 0.5064 0.4228 0.022 Uiso calc R 1 1 . .
C C11 0.95194(17) 0.41679(8) 0.38686(7) 0.0170(2) Uani d . 1 1 . .
H H11A 1.0701 0.4525 0.4217 0.020 Uiso calc R 1 1 . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O3 S1 O2 . . 115.10(5) ?
O3 S1 O1 . . 111.29(5) ?
O2 S1 O1 . . 110.83(5) ?
O3 S1 C1 . . 107.38(5) ?
O2 S1 C1 . . 106.22(5) ?
O1 S1 C1 . . 105.36(5) ?
C6 C1 C2 . . 120.29(10) ?
C6 C1 S1 . . 119.39(8) ?
C2 C1 S1 . . 120.31(8) ?
C3 C2 C1 . . 119.41(11) ?
C3 C2 H2A . . 120.3 ?
C1 C2 H2A . . 120.3 ?
C2 C3 C4 . . 121.30(11) ?
C2 C3 H3A . . 119.4 ?
C4 C3 H3A . . 119.4 ?
C5 C4 C3 . . 118.33(11) ?
C5 C4 C7 . . 120.89(12) ?
C3 C4 C7 . . 120.78(12) ?
C6 C5 C4 . . 121.14(11) ?
C6 C5 H5A . . 119.4 ?
C4 C5 H5A . . 119.4 ?
C5 C6 C1 . . 119.52(11) ?
C5 C6 H6A . . 120.2 ?
C1 C6 H6A . . 120.2 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C7 H7D . . 109.5 ?
H7A C7 H7D . . 141.1 ?
H7B C7 H7D . . 56.3 ?
H7C C7 H7D . . 56.3 ?
C4 C7 H7E . . 109.5 ?
H7A C7 H7E . . 56.3 ?
H7B C7 H7E . . 141.1 ?
H7C C7 H7E . . 56.3 ?
H7D C7 H7E . . 109.5 ?
C4 C7 H7F . . 109.5 ?
H7A C7 H7F . . 56.3 ?
H7B C7 H7F . . 56.3 ?
H7C C7 H7F . . 141.1 ?
H7D C7 H7F . . 109.5 ?
H7E C7 H7F . . 109.5 ?
C9 N1 C8 . . 121.24(9) ?
C9 N1 H1A . . 119.4 ?
C8 N1 H1A . . 119.4 ?
C11 N2 C8 . . 116.81(10) ?
C8 N3 H3B . . 120.0 ?
C8 N3 H3C . . 120.0 ?
H3B N3 H3C . . 120.0 ?
N3 C8 N2 . . 119.44(10) ?
N3 C8 N1 . . 119.13(10) ?
N2 C8 N1 . . 121.43(10) ?
N1 C9 C10 . . 119.59(10) ?
N1 C9 H9A . . 120.2 ?
C10 C9 H9A . . 120.2 ?
C9 C10 C11 . . 116.28(10) ?
C9 C10 H10A . . 121.9 ?
C11 C10 H10A . . 121.9 ?
N2 C11 C10 . . 124.57(10) ?
N2 C11 H11A . . 117.7 ?
C10 C11 H11A . . 117.7 ?
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
S1 O3 . 1.4449(8) ?
S1 O2 . 1.4580(8) ?
S1 O1 . 1.4814(8) ?
S1 C1 . 1.7697(11) ?
C1 C6 . 1.3930(15) ?
C1 C2 . 1.3941(15) ?
C2 C3 . 1.3895(16) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3985(18) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3946(19) ?
C4 C7 . 1.5067(17) ?
C5 C6 . 1.3929(17) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C7 H7D . 0.9800 ?
C7 H7E . 0.9800 ?
C7 H7F . 0.9800 ?
N1 C9 . 1.3529(14) ?
N1 C8 . 1.3579(14) ?
N1 H1A . 0.8800 ?
N2 C11 . 1.3233(14) ?
N2 C8 . 1.3500(14) ?
N3 C8 . 1.3296(14) ?
N3 H3B . 0.8800 ?
N3 H3C . 0.8800 ?
C9 C10 . 1.3631(15) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.4060(15) ?
C10 H10A . 0.9500 ?
C11 H11A . 0.9500 ?
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
_geom_hbond_publ_flag
N1 H1A O1 . 0.88 1.79 2.6740(10) 176 y
N3 H3B O1 1_655 0.88 2.03 2.8350(10) 151 y
N3 H3C O2 . 0.88 2.08 2.9020(10) 155 y
C10 H10A O3 2_555 0.95 2.46 3.1035(14) 124 y
C11 H11A O3 2_655 0.95 2.56 3.3629(14) 143 y
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
O3 S1 C1 C6 . . . . -152.15(9) ?
O2 S1 C1 C6 . . . . -28.51(10) ?
O1 S1 C1 C6 . . . . 89.14(9) ?
O3 S1 C1 C2 . . . . 29.29(10) ?
O2 S1 C1 C2 . . . . 152.94(9) ?
O1 S1 C1 C2 . . . . -89.42(9) ?
C6 C1 C2 C3 . . . . -0.06(16) ?
S1 C1 C2 C3 . . . . 178.49(9) ?
C1 C2 C3 C4 . . . . -0.03(17) ?
C2 C3 C4 C5 . . . . -0.07(18) ?
C2 C3 C4 C7 . . . . 179.54(11) ?
C3 C4 C5 C6 . . . . 0.25(18) ?
C7 C4 C5 C6 . . . . -179.36(12) ?
C4 C5 C6 C1 . . . . -0.34(18) ?
C2 C1 C6 C5 . . . . 0.24(17) ?
S1 C1 C6 C5 . . . . -178.32(9) ?
C11 N2 C8 N3 . . . . 178.22(10) ?
C11 N2 C8 N1 . . . . -2.14(15) ?
C9 N1 C8 N3 . . . . -178.11(10) ?
C9 N1 C8 N2 . . . . 2.25(16) ?
C8 N1 C9 C10 . . . . -0.06(16) ?
N1 C9 C10 C11 . . . . -1.95(15) ?
C8 N2 C11 C10 . . . . -0.04(16) ?
C9 C10 C11 N2 . . . . 2.07(16) ?
