#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/76/2017699.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_2017699
loop_
_publ_author_name
'Thanigaimani, Kaliyaperumal'
'Devi, Periasamy'
'Muthiah, Packianathan Thomas'
'Lynch, Daniel E.'
'Butcher, Ray J.'
_publ_section_title
;
 Charge-assisted hydrogen-bonded supramolecular networks in
 acetoguanaminium hydrogen phthalate, acetoguanaminium hydrogen maleate
 and acetoguanaminium 3-hydroxypicolinate monohydrate
;
_journal_coeditor_code           FA3215
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o324
_journal_page_last               o328
_journal_paper_doi               10.1107/S0108270110014150
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H8 N5 + , C4 H3 O4 -'
_chemical_formula_moiety         'C4 H8 N5 + , C4 H3 O4 -'
_chemical_formula_sum            'C8 H11 N5 O4'
_chemical_formula_weight         241.22
_chemical_name_common            'acetoguanaminium hydrogen maleate'
_chemical_name_systematic
;
2,4-diamino-6-methyl-1,3,5-triazin-1-ium hydrogen maleate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.287(2)
_cell_angle_beta                 104.656(2)
_cell_angle_gamma                91.032(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1921(3)
_cell_length_b                   8.2359(3)
_cell_length_c                   9.4775(4)
_cell_measurement_reflns_used    3779
_cell_measurement_temperature    293
_cell_measurement_theta_max      32.4
_cell_measurement_theta_min      2.5
_cell_volume                     536.58(4)
_computing_cell_refinement
;
APEX2 (Bruker, 2004) and SAINT (Bruker, 2004)
;
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction
;
SAINT (Bruker, 2004) and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEPII (Johnson, 1976) and 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 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13516
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        32.37
_diffrn_reflns_theta_max         32.37
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.258
_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     156
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0496
_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)+(0.0865P)²+0.1115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                2607
_reflns_number_total             3779
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3215.cif
_cod_data_source_block           II
_cod_database_code               2017699
_cod_database_fobs_code          2017699
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.29101(16) 0.47306(12) 0.57202(12) 0.0358(3) Uani . . 1.000
N N2 0.23873(19) 0.34969(14) 0.33003(12) 0.0441(4) Uani . . 1.000
N N3 0.38794(16) 0.20652(13) 0.51373(11) 0.0363(3) Uani . . 1.000
N N4 0.53588(19) 0.07940(15) 0.70623(14) 0.0457(4) Uani . . 1.000
N N5 0.43865(18) 0.33738(14) 0.76624(12) 0.0399(3) Uani . . 1.000
C C2 0.30591(18) 0.34067(15) 0.47085(13) 0.0336(3) Uani . . 1.000
C C4 0.45226(19) 0.21006(15) 0.65985(14) 0.0353(3) Uani . . 1.000
C C6 0.35816(19) 0.46583(16) 0.71766(14) 0.0369(3) Uani . . 1.000
C C7 0.3359(3) 0.61225(19) 0.82164(17) 0.0503(5) Uani . . 1.000
O O1 0.12718(18) 0.75173(13) 0.48301(11) 0.0526(4) Uani . . 1.000
O O2 0.07583(19) 0.63810(13) 0.25017(12) 0.0537(4) Uani . . 1.000
O O3 -0.0875(2) 0.69956(14) 0.00684(11) 0.0639(4) Uani . . 1.000
O O4 -0.2559(2) 0.89879(14) -0.07827(12) 0.0575(4) Uani . . 1.000
C C8 0.0698(2) 0.75762(15) 0.34939(14) 0.0374(4) Uani . . 1.000
C C9 -0.0111(2) 0.91341(15) 0.30547(14) 0.0407(4) Uani . . 1.000
C C10 -0.1043(2) 0.94639(15) 0.17320(14) 0.0406(4) Uani . . 1.000
C C11 -0.1544(2) 0.84338(17) 0.02636(14) 0.0414(4) Uani . . 1.000
H H1 0.23940 0.56000 0.54320 0.0430 Uiso calc R 1.000
H H2A 0.24760 0.26830 0.26460 0.0530 Uiso calc R 1.000
H H2B 0.18580 0.43700 0.30320 0.0530 Uiso calc R 1.000
H H4A 0.54740 -0.00380 0.64350 0.0550 Uiso calc R 1.000
H H4B 0.57890 0.07740 0.79920 0.0550 Uiso calc R 1.000
H H7A 0.39300 0.59500 0.92110 0.0760 Uiso calc R 1.000
H H7B 0.20160 0.62980 0.80970 0.0760 Uiso calc R 1.000
H H7C 0.39880 0.70690 0.80150 0.0760 Uiso calc R 1.000
H H3 -0.02850 0.67630 0.08680 0.0960 Uiso calc R 1.000
H H9 0.00600 1.00110 0.38210 0.0490 Uiso calc R 1.000
H H10 -0.14500 1.05290 0.17330 0.0490 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O3 H3 . . . 109.00 no
C2 N1 C6 . . . 119.39(11) no
C2 N3 C4 . . . 115.87(11) no
C4 N5 C6 . . . 115.48(11) no
C2 N1 H1 . . . 120.00 no
C6 N1 H1 . . . 120.00 no
C2 N2 H2A . . . 120.00 no
C2 N2 H2B . . . 120.00 no
H2A N2 H2B . . . 120.00 no
H4A N4 H4B . . . 120.00 no
C4 N4 H4A . . . 120.00 no
C4 N4 H4B . . . 120.00 no
N2 C2 N3 . . . 120.60(11) no
N1 C2 N2 . . . 118.47(11) no
N1 C2 N3 . . . 120.94(11) no
N3 C4 N5 . . . 125.89(12) no
N4 C4 N5 . . . 116.65(12) no
N3 C4 N4 . . . 117.46(12) no
N5 C6 C7 . . . 120.74(12) no
N1 C6 N5 . . . 122.43(12) no
N1 C6 C7 . . . 116.83(12) no
C6 C7 H7B . . . 109.00 no
C6 C7 H7C . . . 109.00 no
H7A C7 H7B . . . 109.00 no
H7A C7 H7C . . . 109.00 no
H7B C7 H7C . . . 109.00 no
C6 C7 H7A . . . 109.00 no
O1 C8 O2 . . . 123.24(13) no
O2 C8 C9 . . . 119.39(12) no
O1 C8 C9 . . . 117.37(12) no
C8 C9 C10 . . . 129.89(12) no
C9 C10 C11 . . . 131.29(12) no
O3 C11 C10 . . . 120.92(12) no
O4 C11 C10 . . . 118.76(13) no
O3 C11 O4 . . . 120.28(12) no
C8 C9 H9 . . . 115.00 no
C10 C9 H9 . . . 115.00 no
C9 C10 H10 . . . 114.00 no
C11 C10 H10 . . . 114.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . . 1.2371(16) no
O2 C8 . . 1.2690(17) no
O3 C11 . . 1.2927(19) no
O4 C11 . . 1.2250(18) no
O3 H3 . . 0.8200 no
N1 C6 . . 1.3526(17) no
N1 C2 . . 1.3691(16) no
N2 C2 . . 1.3129(16) no
N3 C2 . . 1.3287(17) no
N3 C4 . . 1.3403(16) no
N4 C4 . . 1.3186(18) no
N5 C6 . . 1.3015(18) no
N5 C4 . . 1.3692(17) no
N1 H1 . . 0.8600 no
N2 H2B . . 0.8600 no
N2 H2A . . 0.8600 no
N4 H4B . . 0.8600 no
N4 H4A . . 0.8600 no
C6 C7 . . 1.482(2) no
C7 H7C . . 0.9600 no
C7 H7A . . 0.9600 no
C7 H7B . . 0.9600 no
C8 C9 . . 1.4888(18) no
C9 C10 . . 1.3319(18) no
C10 C11 . . 1.4769(18) no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C2 3.3425(19) . 2_566 no
O1 C9 3.4143(17) . 2_576 no
O1 N1 2.7423(15) . . no
O2 C6 3.321(2) . 2_566 no
O2 N2 2.7852(16) . . no
O2 C11 3.0752(18) . . no
O2 O3 2.4375(15) . . no
O3 N2 3.0650(15) . 2_565 no
O3 O2 2.4375(15) . . no
O3 C8 3.1182(16) . . no
O4 C10 3.246(2) . 2_575 no
O4 N4 2.8346(17) . 1_464 no
O4 N2 2.9406(16) . 2_565 no
O1 H1 1.8800 . . no
O1 H9 2.5800 . 2_576 no
O2 H7B 2.8400 . 2_566 no
O2 H1 2.9000 . . no
O2 H3 1.6200 . . no
O2 H2B 1.9300 . . no
O3 H2B 2.8900 . 2_565 no
O3 H2A 2.5900 . 2_565 no
O4 H7C 2.8100 . 1_454 no
O4 H2A 2.0900 . 2_565 no
O4 H4B 2.1900 . 1_464 no
O4 H4A 2.8900 . 1_464 no
N1 O1 2.7423(15) . . no
N1 C2 3.3968(17) . 2_666 no
N2 O2 2.7852(16) . . no
N2 C11 3.4184(17) . 2_565 no
N2 C6 3.4089(19) . 2_666 no
N2 O4 2.9406(16) . 2_565 no
N2 O3 3.0650(15) . 2_565 no
N3 N4 3.0660(17) . 2_656 no
N4 O4 2.8346(17) . 1_646 no
N4 C9 3.447(2) . 2_666 no
N4 N3 3.0660(17) . 2_656 no
N4 C8 3.308(2) . 2_666 no
N3 H4A 2.2100 . 2_656 no
N5 H7A 2.8700 . 2_667 no
C2 N1 3.3968(17) . 2_666 no
C2 O1 3.3425(19) . 2_566 no
C4 C8 3.467(2) . 2_666 no
C4 C10 3.592(2) . 2_566 no
C4 C9 3.423(2) . 2_566 no
C6 O2 3.321(2) . 2_566 no
C6 C8 3.425(2) . 2_566 no
C6 N2 3.4089(19) . 2_666 no
C8 C6 3.425(2) . 2_566 no
C8 C4 3.467(2) . 2_666 no
C8 N4 3.308(2) . 2_666 no
C8 O3 3.1182(16) . . no
C9 N4 3.447(2) . 2_666 no
C9 O1 3.4143(17) . 2_576 no
C9 C4 3.423(2) . 2_566 no
C10 C11 3.556(2) . 2_575 no
C10 O4 3.246(2) . 2_575 no
C10 C4 3.592(2) . 2_566 no
C11 N2 3.4184(17) . 2_565 no
C11 C10 3.556(2) . 2_575 no
C11 C11 3.545(2) . 2_575 no
C11 O2 3.0752(18) . . no
C8 H3 2.4000 . . no
C8 H2B 2.7900 . . no
C8 H1 2.7000 . . no
C9 H9 2.9300 . 2_576 no
C9 H3 2.6100 . . no
C11 H2A 2.6900 . 2_565 no
H1 H7B 2.5900 . . no
H1 H7C 2.5400 . . no
H1 H2B 2.2900 . . no
H1 O1 1.8800 . . no
H1 O2 2.9000 . . no
H1 C8 2.7000 . . no
H2A O3 2.5900 . 2_565 no
H2A O4 2.0900 . 2_565 no
H2A C11 2.6900 . 2_565 no
H2B O2 1.9300 . . no
H2B O3 2.8900 . 2_565 no
H2B C8 2.7900 . . no
H2B H1 2.2900 . . no
H3 O2 1.6200 . . no
H3 C9 2.6100 . . no
H3 C8 2.4000 . . no
H4A N3 2.2100 . 2_656 no
H4A O4 2.8900 . 1_646 no
H4B O4 2.1900 . 1_646 no
H7A H7A 2.5800 . 2_667 no
H7A N5 2.8700 . 2_667 no
H7B H1 2.5900 . . no
H7B O2 2.8400 . 2_566 no
H7C H1 2.5400 . . no
H7C O4 2.8100 . 1_656 no
H9 O1 2.5800 . 2_576 no
H9 C9 2.9300 . 2_576 no
H9 H9 2.2600 . 2_576 no
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 H1 O1 . 0.8600 1.8800 2.7423(15) 179.00 yes
N2 H2A O3 2_565 0.8600 2.5900 3.0650(15) 116.00 yes
N2 H2A O4 2_565 0.8600 2.0900 2.9406(16) 169.00 yes
N2 H2B O2 . 0.8600 1.9300 2.7852(16) 177.00 yes
O3 H3 O2 . 0.8200 1.6200 2.4375(15) 176.00 yes
N4 H4A N3 2_656 0.8600 2.2100 3.0660(17) 173.00 yes
N4 H4B O4 1_646 0.8600 2.1900 2.8346(17) 132.00 yes
C9 H9 O1 2_576 0.9300 2.5800 3.4143(17) 150.00 yes
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 N1 C2 N2 . . . . 179.56(13) no
C6 N1 C2 N3 . . . . -1.05(19) no
C2 N1 C6 C7 . . . . -179.33(14) no
C2 N1 C6 N5 . . . . 0.6(2) no
C4 N3 C2 N2 . . . . 179.79(13) no
C2 N3 C4 N4 . . . . -179.47(13) no
C4 N3 C2 N1 . . . . 0.41(19) no
C2 N3 C4 N5 . . . . 0.7(2) no
C6 N5 C4 N4 . . . . 179.02(13) no
C6 N5 C4 N3 . . . . -1.2(2) no
C4 N5 C6 N1 . . . . 0.5(2) no
C4 N5 C6 C7 . . . . -179.63(14) no
O1 C8 C9 C10 . . . . -170.33(16) no
O2 C8 C9 C10 . . . . 9.2(2) no
C8 C9 C10 C11 . . . . -1.8(3) no
C9 C10 C11 O3 . . . . -8.3(3) no
C9 C10 C11 O4 . . . . 174.06(16) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654246
