data_2013212 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2003 _journal_volume 59 _journal_page_first o102 _journal_page_last o104 _publ_section_title ; 2-Amino-5-nitro-4,6-dipiperidinopyrimidinium hydrogensulfate monohydrate: hydrogen-bonded sheets containing highly distorted cations ; loop_ _publ_author_name 'Quesada, Antonio' 'Marchal, Antonio' 'Low, John N.' 'Glidewell, Christopher' _chemical_formula_moiety 'C14 H23 N6 O2 1+, H O4 S 1-, H2 O' _chemical_formula_sum 'C14 H26 N6 O7 S' _chemical_formula_iupac 'C14 H23 N6 O2 1+, H O4 S 1-, H2 O' _chemical_formula_weight 422.48 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0307(3) _cell_length_b 6.12770(10) _cell_length_c 21.5135(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.4850(10) _cell_angle_gamma 90.00 _cell_volume 1849.02(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.518 _diffrn_ambient_temperature 120(2) loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.35950(10) 0.8253(2) 0.21146(7) 0.0142(3) Uani d . 1 . . N C2 0.36798(12) 0.6762(3) 0.25504(8) 0.0134(3) Uani d . 1 . . C N2 0.44503(11) 0.5536(2) 0.25916(7) 0.0180(3) Uani d . 1 . . N N3 0.30117(10) 0.6465(2) 0.30023(6) 0.0142(3) Uani d . 1 . . N C4 0.21289(12) 0.7390(3) 0.29458(8) 0.0138(3) Uani d . 1 . . C N4 0.15067(10) 0.7003(2) 0.33825(7) 0.0147(3) Uani d . 1 . . N C41 0.15104(13) 0.5018(3) 0.37739(8) 0.0175(4) Uani d . 1 . . C C42 0.15968(14) 0.5596(3) 0.44592(8) 0.0224(4) Uani d . 1 . . C C43 0.08198(14) 0.7214(3) 0.46352(9) 0.0240(4) Uani d . 1 . . C C44 0.08465(13) 0.9206(3) 0.42086(8) 0.0205(4) Uani d . 1 . . C C45 0.07389(13) 0.8545(3) 0.35280(8) 0.0172(4) Uani d . 1 . . C C5 0.19551(12) 0.8699(3) 0.24064(8) 0.0134(3) Uani d . 1 . . C N5 0.10624(10) 0.8458(2) 0.20829(7) 0.0156(3) Uani d . 1 . . N O51 0.09797(9) 0.9227(2) 0.15452(6) 0.0197(3) Uani d . 1 . . O O52 0.04111(9) 0.7403(2) 0.23176(6) 0.0214(3) Uani d . 1 . . O C6 0.27842(12) 0.9432(3) 0.20722(7) 0.0131(3) Uani d . 1 . . C N6 0.27924(10) 1.1197(2) 0.17184(6) 0.0140(3) Uani d . 1 . . N C61 0.20926(12) 1.2975(3) 0.17605(8) 0.0154(4) Uani d . 1 . . C C62 0.17517(13) 1.3751(3) 0.11210(8) 0.0176(4) Uani d . 1 . . C C63 0.25982(13) 1.4374(3) 0.07255(8) 0.0204(4) Uani d . 1 . . C C64 0.32920(13) 1.2469(3) 0.06910(8) 0.0184(4) Uani d . 1 . . C C65 0.36217(12) 1.1725(3) 0.13367(8) 0.0165(4) Uani d . 1 . . C S1 0.40346(3) 0.18484(7) 0.38826(2) 0.01580(10) Uani d . 1 . . S O1 0.39781(10) 0.1434(2) 0.32170(6) 0.0213(3) Uani d . 1 . . O O2 0.38376(10) 0.4149(2) 0.40125(6) 0.0223(3) Uani d . 1 . . O O3 0.33651(10) 0.0435(2) 0.42136(6) 0.0255(3) Uani d . 1 . . O O4 0.50332(10) 0.1311(2) 0.40980(8) 0.0325(4) Uani d . 1 . . O O8 0.58819(16) 0.2711(3) 0.50806(8) 0.0545(6) Uani d . 1 . . O H2A 0.4911 0.5715 0.2326 0.022 Uiso calc R 1 . . H H2B 0.4505 0.4538 0.2885 0.022 Uiso calc R 1 . . H H3 0.3157 0.5668 0.3332 0.017 Uiso calc R 1 . . H H41A 0.2051 0.4073 0.3661 0.021 Uiso calc R 1 . . H H41B 0.0913 0.4191 0.3695 0.021 Uiso calc R 1 . . H H42A 0.2231 0.6245 0.4550 0.027 Uiso calc R 1 . . H H42B 0.1540 0.4254 0.4712 0.027 Uiso calc R 1 . . H H43A 0.0920 0.7677 0.5073 0.029 Uiso calc R 1 . . H H43B 0.0188 0.6502 0.4596 0.029 Uiso calc R 1 . . H H44A 0.0325 1.0218 0.4314 0.025 Uiso calc R 1 . . H H44B 0.1459 0.9985 0.4276 0.025 Uiso calc R 1 . . H H45A 0.0110 0.7849 0.3451 0.021 Uiso calc R 1 . . H H45B 0.0779 0.9851 0.3259 0.021 Uiso calc R 1 . . H H61A 0.2385 1.4214 0.1991 0.018 Uiso calc R 1 . . H H61B 0.1539 1.2461 0.1996 0.018 Uiso calc R 1 . . H H62A 0.1328 1.5031 0.1166 0.021 Uiso calc R 1 . . H H62B 0.1381 1.2577 0.0911 0.021 Uiso calc R 1 . . H H63A 0.2369 1.4772 0.0301 0.024 Uiso calc R 1 . . H H63B 0.2927 1.5658 0.0910 0.024 Uiso calc R 1 . . H H64A 0.2978 1.1237 0.0469 0.022 Uiso calc R 1 . . H H64B 0.3852 1.2915 0.0451 0.022 Uiso calc R 1 . . H H65A 0.4033 1.0420 0.1301 0.020 Uiso calc R 1 . . H H65B 0.4002 1.2895 0.1541 0.020 Uiso calc R 1 . . H H4 0.5253 0.1994 0.4396 0.039 Uiso d R 1 . . H H81 0.6178 0.1786 0.5410 0.065 Uiso d R 1 . . H H82 0.5923 0.3968 0.5370 0.065 Uiso d R 1 . . H 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 N1 0.0106(7) 0.0162(7) 0.0158(7) 0.0003(5) 0.0001(5) 0.0003(5) C2 0.0100(8) 0.0154(8) 0.0148(8) -0.0016(6) -0.0009(6) -0.0019(6) N2 0.0136(8) 0.0221(8) 0.0185(7) 0.0040(6) 0.0029(6) 0.0049(6) N3 0.0103(7) 0.0181(7) 0.0140(7) 0.0015(5) -0.0005(6) 0.0031(6) C4 0.0103(8) 0.0135(8) 0.0178(8) -0.0003(6) -0.0004(6) -0.0027(6) N4 0.0108(7) 0.0156(7) 0.0178(7) 0.0019(5) 0.0020(5) 0.0029(5) C41 0.0127(9) 0.0179(8) 0.0219(9) 0.0006(7) 0.0018(7) 0.0056(7) C42 0.0185(10) 0.0278(10) 0.0208(9) 0.0008(7) 0.0005(7) 0.0067(7) C43 0.0194(10) 0.0346(11) 0.0183(9) 0.0001(8) 0.0026(7) 0.0022(8) C44 0.0146(9) 0.0239(9) 0.0231(9) 0.0015(7) 0.0028(7) -0.0026(7) C45 0.0106(8) 0.0201(8) 0.0211(9) 0.0026(7) 0.0022(7) 0.0017(7) C5 0.0078(8) 0.0159(8) 0.0164(8) -0.0002(6) -0.0009(6) 0.0000(6) N5 0.0114(7) 0.0156(7) 0.0197(7) 0.0006(5) -0.0019(6) -0.0005(6) O51 0.0164(7) 0.0231(6) 0.0192(6) -0.0019(5) -0.0058(5) 0.0046(5) O52 0.0121(6) 0.0266(7) 0.0254(7) -0.0077(5) -0.0010(5) 0.0022(5) C6 0.0126(8) 0.0145(8) 0.0120(7) -0.0014(6) -0.0022(6) -0.0022(6) N6 0.0091(7) 0.0166(7) 0.0164(7) 0.0000(5) 0.0001(5) 0.0003(6) C61 0.0138(9) 0.0140(8) 0.0183(8) 0.0003(6) 0.0002(7) -0.0003(6) C62 0.0134(9) 0.0184(8) 0.0210(9) 0.0020(7) -0.0005(7) 0.0024(7) C63 0.0171(9) 0.0230(9) 0.0211(8) 0.0008(7) 0.0011(7) 0.0065(7) C64 0.0142(9) 0.0233(9) 0.0177(8) -0.0007(7) 0.0008(7) 0.0024(7) C65 0.0102(8) 0.0204(9) 0.0192(8) 0.0004(6) 0.0026(7) 0.0032(7) S1 0.0152(2) 0.0167(2) 0.0156(2) 0.00161(16) 0.00183(16) 0.00025(15) O1 0.0247(7) 0.0232(7) 0.0163(6) -0.0015(5) 0.0049(5) -0.0032(5) O2 0.0271(8) 0.0193(6) 0.0203(6) 0.0072(6) -0.0057(5) -0.0028(5) O3 0.0228(7) 0.0295(7) 0.0246(7) -0.0017(6) 0.0063(6) 0.0076(6) O4 0.0166(8) 0.0286(7) 0.0516(9) 0.0060(6) -0.0125(7) -0.0075(7) O8 0.1103(18) 0.0216(8) 0.0324(9) -0.0127(9) 0.0170(10) -0.0043(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 N1 C2 . 1.312(2) y C2 N3 . 1.380(2) y N3 C4 . 1.365(2) y C4 C5 . 1.426(2) y C5 C6 . 1.454(2) y C6 N1 . 1.349(2) y C2 N2 . 1.318(2) y C4 N4 . 1.321(2) y C5 N5 . 1.425(2) y N5 O51 . 1.252(2) y N5 O52 . 1.238(2) y C6 N6 . 1.323(2) y N2 H2A . 0.88 no N2 H2B . 0.88 no N3 H3 . 0.88 no N4 C45 . 1.473(2) no N4 C41 . 1.479(2) no C41 C42 . 1.518(2) no C41 H41A . 0.99 no C41 H41B . 0.99 no C42 C43 . 1.528(3) no C42 H42A . 0.99 no C42 H42B . 0.99 no C43 C44 . 1.529(3) no C43 H43A . 0.99 no C43 H43B . 0.99 no C44 C45 . 1.523(2) no C44 H44A . 0.99 no C44 H44B . 0.99 no C45 H45A . 0.99 no C45 H45B . 0.99 no N6 C61 . 1.471(2) no N6 C65 . 1.477(2) no C61 C62 . 1.521(2) no C61 H61A . 0.99 no C61 H61B . 0.99 no C62 C63 . 1.527(3) no C62 H62A . 0.99 no C62 H62B . 0.99 no C63 C64 . 1.523(3) no C63 H63A . 0.99 no C63 H63B . 0.99 no C64 C65 . 1.523(2) no C64 H64A . 0.99 no C64 H64B . 0.99 no C65 H65A . 0.99 no C65 H65B . 0.99 no S1 O1 . 1.4545(13) no S1 O2 . 1.4650(13) no S1 O3 . 1.4743(14) no S1 O4 . 1.5008(14) no O4 H4 . 0.82 no O8 H81 . 0.99 no O8 H82 . 0.99 no