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The crystal structure of the title compound, 6-amino-2-oxo-1,2-dihydro-9H-purine-3,7-diium dichloride dihydrate, C5H7N5O2+·2Cl·2H2O, consists of hydrogen-bonded layers parallel to (10\overline{1}). In addition, pairs of layers are connected by an O—H...Cl hydrogen bond and there are also short Cl...C and Cl...N contacts between the layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014061/lh2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014061/lh2045Isup2.hkl
Contains datablock I

CCDC reference: 608453

Key indicators

  • Single-crystal X-ray study
  • T = 154 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.113
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT352_ALERT_3_C Short N-H Bond (0.87A) N1 - H1A ... 0.73 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Cl1 .. C8 .. 3.24 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.

6-amino-2-oxo-1,2-dihydro-9H-purine-3,7-diium dichloride dihydrate top
Crystal data top
C5H7N5O2+·2Cl·2H2OF(000) = 1072
Mr = 260.09Dx = 1.645 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 81 reflections
a = 19.896 (3) Åθ = 3–23°
b = 9.120 (3) ŵ = 0.62 mm1
c = 13.077 (3) ÅT = 154 K
β = 117.713 (16)°Parallelepiped, colorless
V = 2100.7 (10) Å30.44 × 0.26 × 0.11 mm
Z = 8
Data collection top
Siemens SMART 1K CCD
diffractometer
3248 independent reflections
Radiation source: normal-focus sealed tube2438 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 31.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 2825
Tmin = 0.846, Tmax = 0.935k = 1311
13739 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.113All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
3248 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.37147 (3)0.37134 (5)0.50015 (4)0.01967 (14)
Cl20.67550 (3)0.01416 (5)0.80874 (4)0.02247 (14)
O10.44336 (10)0.00930 (19)0.58693 (17)0.0313 (4)
O20.49788 (9)0.71785 (17)0.61992 (13)0.0250 (3)
O30.33384 (10)0.70790 (18)0.47289 (16)0.0287 (4)
N10.53143 (10)0.4787 (2)0.64785 (15)0.0175 (4)
N30.62007 (10)0.66124 (19)0.74813 (15)0.0169 (3)
N60.55575 (12)0.2292 (2)0.66612 (17)0.0215 (4)
N70.72199 (9)0.3310 (2)0.83664 (14)0.0163 (3)
N90.74626 (10)0.5635 (2)0.87455 (15)0.0166 (3)
C20.54751 (11)0.6262 (2)0.66880 (16)0.0177 (4)
C40.67208 (11)0.5519 (2)0.79450 (16)0.0141 (4)
C50.65539 (11)0.4070 (2)0.76952 (16)0.0150 (4)
C60.58039 (11)0.3643 (2)0.69370 (16)0.0155 (4)
C80.77484 (12)0.4269 (2)0.89759 (18)0.0180 (4)
H1A0.4921 (15)0.459 (3)0.608 (2)0.023 (7)*
H1B0.4139 (18)0.004 (3)0.626 (3)0.059 (10)*
H1C0.475 (2)0.070 (4)0.601 (3)0.056 (10)*
H3A0.6327 (17)0.753 (3)0.759 (2)0.043 (9)*
H3B0.3818 (16)0.707 (3)0.514 (2)0.026 (7)*
H3C0.325 (2)0.624 (5)0.454 (3)0.063 (11)*
H6A0.5849 (17)0.167 (4)0.693 (2)0.042 (9)*
H6B0.5068 (17)0.215 (3)0.620 (2)0.028 (7)*
H7A0.7280 (16)0.239 (3)0.839 (2)0.034 (8)*
H8A0.8247 (14)0.406 (3)0.945 (2)0.019 (6)*
H9A0.7701 (17)0.640 (3)0.900 (2)0.036 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0163 (2)0.0170 (2)0.0220 (2)0.00256 (18)0.00585 (19)0.00196 (18)
Cl20.0243 (3)0.0126 (2)0.0272 (3)0.00070 (19)0.0092 (2)0.00029 (19)
O10.0241 (8)0.0190 (8)0.0457 (11)0.0003 (7)0.0118 (8)0.0001 (7)
O20.0196 (8)0.0175 (7)0.0299 (8)0.0058 (6)0.0048 (6)0.0024 (6)
O30.0209 (9)0.0135 (8)0.0376 (9)0.0019 (7)0.0019 (8)0.0004 (7)
N10.0130 (8)0.0156 (9)0.0190 (8)0.0011 (7)0.0033 (7)0.0006 (7)
N30.0169 (8)0.0114 (8)0.0196 (8)0.0004 (7)0.0062 (7)0.0010 (6)
N60.0190 (10)0.0139 (9)0.0248 (9)0.0016 (8)0.0044 (8)0.0002 (7)
N70.0159 (8)0.0123 (8)0.0182 (8)0.0026 (7)0.0057 (7)0.0018 (7)
N90.0152 (8)0.0138 (9)0.0175 (8)0.0013 (7)0.0049 (6)0.0021 (6)
C20.0187 (10)0.0169 (10)0.0165 (9)0.0009 (8)0.0073 (8)0.0001 (7)
C40.0155 (9)0.0132 (9)0.0129 (8)0.0006 (7)0.0061 (7)0.0001 (7)
C50.0159 (9)0.0130 (9)0.0155 (9)0.0031 (7)0.0066 (8)0.0023 (7)
C60.0181 (9)0.0136 (9)0.0154 (8)0.0017 (8)0.0082 (8)0.0002 (7)
C80.0164 (10)0.0169 (10)0.0177 (9)0.0023 (8)0.0055 (8)0.0004 (8)
Geometric parameters (Å, º) top
O1—H1B0.95 (3)N6—H6A0.77 (3)
O1—H1C0.92 (4)N6—H6B0.89 (3)
O2—C21.223 (3)N7—C81.314 (3)
O3—H3B0.85 (3)N7—C51.388 (2)
O3—H3C0.80 (4)N7—H7A0.84 (3)
N1—C61.362 (3)N9—C81.344 (3)
N1—C21.380 (3)N9—C41.360 (3)
N1—H1A0.73 (3)N9—H9A0.83 (3)
N3—C41.360 (3)C4—C51.364 (3)
N3—C21.367 (3)C5—C61.409 (3)
N3—H3A0.87 (3)C8—H8A0.91 (3)
N6—C61.313 (3)
H1B—O1—H1C109 (3)C4—N9—H9A126 (2)
H3B—O3—H3C102 (3)O2—C2—N3123.2 (2)
C6—N1—C2127.38 (18)O2—C2—N1120.41 (19)
C6—N1—H1A116 (2)N3—C2—N1116.35 (18)
C2—N1—H1A117 (2)N9—C4—N3127.91 (18)
C4—N3—C2118.88 (18)N9—C4—C5108.43 (17)
C4—N3—H3A122 (2)N3—C4—C5123.60 (18)
C2—N3—H3A118 (2)C4—C5—N7106.15 (17)
C6—N6—H6A118 (2)C4—C5—C6119.77 (17)
C6—N6—H6B118.7 (18)N7—C5—C6133.94 (18)
H6A—N6—H6B124 (3)N6—C6—N1119.92 (19)
C8—N7—C5108.05 (18)N6—C6—C5126.23 (19)
C8—N7—H7A125.3 (19)N1—C6—C5113.85 (18)
C5—N7—H7A126.6 (19)N7—C8—N9110.22 (18)
C8—N9—C4107.14 (17)N7—C8—H8A125.8 (16)
C8—N9—H9A126 (2)N9—C8—H8A123.9 (16)
C4—N3—C2—O2177.43 (19)N3—C4—C5—C61.4 (3)
C4—N3—C2—N14.4 (3)C8—N7—C5—C40.1 (2)
C6—N1—C2—O2178.87 (19)C8—N7—C5—C6175.7 (2)
C6—N1—C2—N32.9 (3)C2—N1—C6—N6178.95 (19)
C8—N9—C4—N3177.81 (19)C2—N1—C6—C50.8 (3)
C8—N9—C4—C50.5 (2)C4—C5—C6—N6176.8 (2)
C2—N3—C4—N9179.44 (19)N7—C5—C6—N61.7 (4)
C2—N3—C4—C52.5 (3)C4—C5—C6—N12.9 (3)
N9—C4—C5—N70.3 (2)N7—C5—C6—N1178.0 (2)
N3—C4—C5—N7177.73 (17)C5—N7—C8—N90.4 (2)
N9—C4—C5—C6176.08 (17)C4—N9—C8—N70.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.73 (3)2.29 (3)3.017 (2)172 (3)
N3—H3A···Cl2i0.87 (3)2.27 (3)3.130 (2)173 (2)
N6—H6A···Cl20.77 (3)2.39 (3)3.154 (3)170 (3)
N6—H6B···O10.89 (3)2.19 (3)2.818 (3)128 (2)
N7—H7A···Cl20.84 (3)2.49 (3)3.253 (2)151 (3)
N9—H9A···O3ii0.83 (3)1.82 (3)2.637 (3)171 (3)
O1—H1B···Cl2iii0.95 (3)2.30 (4)3.240 (3)169 (3)
O1—H1C···O2iv0.92 (4)1.98 (4)2.827 (3)153 (4)
O3—H3B···O20.85 (3)2.07 (3)2.919 (3)176 (3)
O3—H3C···Cl10.80 (4)2.45 (5)3.140 (2)145 (4)
C8—H8A···Cl1v0.91 (3)2.68 (3)3.240 (2)121 (2)
C8—H8A···O1v0.91 (3)2.35 (3)3.161 (3)147 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z+1/2; (iii) x+1, y, z+3/2; (iv) x, y1, z; (v) x+1/2, y+1/2, z+1/2.
 

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