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The title compound, C4H6N4O·H2O, crystallized simultaneously as a triclinic and a monoclinic polymorph from an aqueous solution of 2,4-diamino­pyrimidin-6-ol. Previously, an ortho­rhom­bic polymorph was isolated under the same experimental conditions. The mol­ecular geometric parameters in the two present polymorphs and the previously reported ortho­rhom­bic polymorph are similar, but the structures differ in the details of their crystal packing. In the triclinic system, the diamino­pyrimidinone mol­ecules are connected to one another via N—H...O and N—H...N hydrogen bonding to form infinite chains in the [011] direction. The chains are further hydrogen bonded to the water mol­ecules, resulting in a three-dimensional network. In the monoclinic system, the diamino­pyrimidinone mol­ecules are hydrogen bonded together into two-dimensional networks parallel to the bc plane. The water mol­ecules link the planes to form a three-dimensional polymeric structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110046317/fn3068sup1.cif
Contains datablocks II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110046317/fn3068IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110046317/fn3068IIIsup3.hkl
Contains datablock III

CCDC references: 813488; 813489

Comment top

Diaminopyrimidines are a class of organic compounds with interesting biological properties (Desharnais et al., 2003) and applications in supramolecular chemistry (Yagai, 2006). Some years ago Skoweranda et al. (1990) reported the crystal structure of 2,6-diamino-4-oxo-3,4-dihydropyrimidinone, cocrystallized with one molecule of water, in an orthorhombic crystal system, (I). During our studies on the crystallization behavior of 2,4-diamino-6-hydroxypyrimidine, we obtained two new polymorphs of the reported compound in triclinic, (II), and monoclinic, (III), systems. Our subsequent efforts to get the orthorhombic form all failed, and therefore it can be regarded as a disappearing polymorph. In fact, recrystallization of 2,4-diamino-6-hydroxypyrimidine from an aqueous solution, the condition which was used by Skoweranda et al., led to concomitant formation of the triclinic and monoclinic crystals.

The thermal ellipsoid drawing of the three polymorphs is given in Fig. 1. In the three polymorphs, the molecules form three-dimensional hydrogen-bonded networks, however with different hydrogen-bond systems. In contrast to the orthorhombic polymorph, (I), in which the water molecules are hydrogen bonded together into infinite chains along the a axis, there is no interaction between the water molecules in the two present polymorphs. Moreover, polymorph (I) shows N4—H4B···N4 hydrogen bonding (Fig. 2) which was not observed in polymorphs (II) and (III). In polymorph (II) the adjacent diaminopyrimidinone molecules are connected to one another via N—H···O and N—H···N hydrogen bonding around centers of inversion to form parallel infinite chains in the [0 1 1] direction. The water molecule has five hydrogen-bonding interactions that involve five different neighboring pyrimidinone molecules (Fig. 3). As a result, the pyrimidinone chains are linked into a three-dimensional network.

In polymorph (III) each two diaminopyrimidinone molecules is N—H···N hydrogen bonded together around centers of inversion. The resulting dimers are further connected together around twofold screw axes along b via N3—H3···O2 hydrogen bonding in a bifurcated system to form two-dimensional networks parallel to the bc plane. The water molecule is engaged in five hydrogen-bonding interactions with five neighboring pyrimidinone molecules (Fig. 4), resulting in a three-dimensional hydrogen-bonded network. Fig. 5 represents the stereoviews of polymorphs (II) and (III).

In both polymorphs, weak ππ stacking occurs between the planar molecules in the direction of the shortest crystallographic axis. The diaminopyrimidinone molecule, including all hydrogen atoms, in the three polymorphs is almost planar [r.m.s deviation: (I) 0.049 Å, (II) 0.031 Å, (III) 0.053 Å] and the bond lengths and angles are similar (Tables 1 and 3). The amino groups do not appear to be pyramidalized to within the uncertainty of the structure determinations. For (II), the sums of the angles at nitrogen are 359.3 (14) and 359.4 (15)° for N2 and N4, respectively, whereas for (III) the corresponding values are 359 (2) and 356 (2)°. Polymorph (III) does exhibit slightly greater deviations than (II) of the NH2 groups from the least-squares planes of the pyrimidinone molecule. These displacements are of opposite sign for the N2 and N4 groups in both polymorphs. The density of the monoclinic polymorph (1.538 Mg m-3) is greater than that of the triclinic structure (1.492 Mg m-3) which might be indicative of higher thermodynamic stability of the monoclinic system (Burger & Ramberger, 1979). The density of polymorph (I) was reported to be 1.476 Mg m-3; however the data were collected at 293 K.

Related literature top

For related literature, see: Burger & Ramberger (1979); Desharnais et al. (2003); Skoweranda et al. (1990); Yagai (2006).

Experimental top

A portion of commercially available 2,4-diaminopyrimidin-6-ol (0.6 g) was dissolved in distilled water (10 ml) by heating and stirring. The resulting solution was then left at room temperature. In less than an hour, crystals of polymorphs (II) and (III) were obtained simultaneously.

Refinement top

The C-bound H atoms were placed in idealized locations (C—H = 0.95 Å) and refined as riding on their parent carbon atoms. The nitrogen- and oxygen-bound H atoms were located in a difference Fourier map and were refined with distance restraints of N—H 0.88 (2) and O—H 0.84 (2) Å. U(H) were set to 1.2Ueq (parent atom).

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric units of the three polymorphs of the title compound, showing the atom-numbering scheme selected to conform to polymorph (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The position of the hydrate molecule has been selected in order to show the shortest hydrogen-bonding interaction between the hydrate and atom O2. The O1···O2 distances are displayed. The structure of polymorph (I) was determined at 293 K, whereas the data of polymorphs (II) and (III) were collected at 100 K.
[Figure 2] Fig. 2. A view of the hydrogen-bonding interactions in polymorph (I). [Symmetry codes: (i) -x+1, y+1/2, -z+1/2; (ii) x, -y-1/2, z+1/2; (iii) -x+1/2, -y, z+1/2; (iv) -x+1/2, y-1/2, z; (v) -x+1, -y-1, -z.]
[Figure 3] Fig. 3. A view of the hydrogen-bonding interactions in polymorph (II). [Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+1; (iii) x-1, y-1, z; (iv) -x+1, -y+1, -z.]
[Figure 4] Fig. 4. A view of the hydrogen-bonding interactions in polymorph (III). [Symmetry codes: (i) x, y+1, z; (ii) -x+1/2, y+3/2, -z+1/2; (iii) x, -y+1, z+1/2; (iv) -x+1, y, -z+1/2; (v) <-x+1, y+1, -z+1/2.]
[Figure 5] Fig. 5. Stereoviews of polymorphs (II) and (III). The stacking of the planar molecules is only shown at the periphery of the figure in order to focus on the hydrogen-bonding patterns in the immediate vicinity of the title molecule. The view is selected such that the title molecules are placed in the same orientation. The stacking motif is in the direction of the shortest axial length, namely the a axis in (II) and the b axis in (III).
(II) 2,6-diaminopyrimidin-4(3H)-one monohydrate top
Crystal data top
C4H6N4O·H2OZ = 2
Mr = 144.14F(000) = 152
Triclinic, P1Dx = 1.492 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.9293 (3) ÅCell parameters from 1370 reflections
b = 8.6611 (7) Åθ = 3.0–30.3°
c = 9.6044 (8) ŵ = 0.12 mm1
α = 83.111 (5)°T = 100 K
β = 88.090 (6)°Block, colorless
γ = 81.479 (6)°0.45 × 0.35 × 0.13 mm
V = 320.88 (4) Å3
Data collection top
Bruker APEXII CCD
diffractometer
1113 independent reflections
Radiation source: fine-focus sealed tube996 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ϕ and ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 44
Tmin = 0.948, Tmax = 0.984k = 1010
2138 measured reflectionsl = 1111
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.073P)2 + 0.0912P]
where P = (Fo2 + 2Fc2)/3
1113 reflections(Δ/σ)max < 0.001
112 parametersΔρmax = 0.20 e Å3
7 restraintsΔρmin = 0.26 e Å3
Crystal data top
C4H6N4O·H2Oγ = 81.479 (6)°
Mr = 144.14V = 320.88 (4) Å3
Triclinic, P1Z = 2
a = 3.9293 (3) ÅMo Kα radiation
b = 8.6611 (7) ŵ = 0.12 mm1
c = 9.6044 (8) ÅT = 100 K
α = 83.111 (5)°0.45 × 0.35 × 0.13 mm
β = 88.090 (6)°
Data collection top
Bruker APEXII CCD
diffractometer
1113 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
996 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.984Rint = 0.017
2138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0367 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.20 e Å3
1113 reflectionsΔρmin = 0.26 e Å3
112 parameters
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
O20.8723 (3)0.42708 (12)0.35218 (11)0.0178 (3)
N11.0531 (3)0.85718 (15)0.16673 (13)0.0163 (3)
N21.2801 (3)0.89049 (16)0.37701 (14)0.0185 (4)
H2A1.345 (5)0.856 (2)0.4627 (17)0.022*
H2B1.344 (4)0.9798 (19)0.3378 (19)0.022*
N31.0696 (3)0.65930 (14)0.35786 (13)0.0153 (3)
H31.105 (4)0.632 (2)0.4461 (16)0.018*
N40.8325 (4)0.82005 (17)0.04094 (14)0.0227 (4)
H4A0.877 (5)0.914 (2)0.072 (2)0.027*
H4B0.713 (5)0.772 (2)0.0924 (19)0.027*
C21.1329 (4)0.80288 (17)0.29798 (16)0.0151 (4)
C40.9195 (4)0.55938 (17)0.28491 (16)0.0154 (4)
C50.8382 (4)0.61166 (19)0.14700 (16)0.0178 (4)
H50.73900.54750.09080.021*
C60.9056 (4)0.76208 (19)0.09153 (16)0.0171 (4)
O10.4541 (3)0.21283 (13)0.32544 (12)0.0204 (3)
H1A0.602 (5)0.274 (2)0.319 (2)0.025*
H1B0.269 (4)0.271 (2)0.3414 (19)0.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0224 (6)0.0142 (6)0.0169 (6)0.0062 (4)0.0023 (4)0.0030 (4)
N10.0191 (7)0.0153 (7)0.0142 (7)0.0038 (5)0.0005 (5)0.0014 (5)
N20.0273 (7)0.0148 (7)0.0138 (7)0.0075 (6)0.0046 (6)0.0032 (5)
N30.0194 (7)0.0148 (7)0.0113 (7)0.0036 (5)0.0015 (5)0.0019 (5)
N40.0367 (8)0.0191 (7)0.0143 (7)0.0134 (6)0.0065 (6)0.0029 (5)
C20.0147 (7)0.0140 (8)0.0158 (8)0.0021 (6)0.0018 (6)0.0008 (6)
C40.0145 (7)0.0137 (7)0.0178 (8)0.0026 (6)0.0016 (6)0.0004 (6)
C50.0197 (8)0.0183 (8)0.0162 (8)0.0064 (6)0.0011 (6)0.0006 (6)
C60.0171 (7)0.0181 (8)0.0157 (8)0.0032 (6)0.0006 (6)0.0002 (6)
O10.0206 (6)0.0161 (6)0.0251 (6)0.0057 (5)0.0024 (5)0.0002 (5)
Geometric parameters (Å, º) top
O2—C41.2815 (18)N4—C61.335 (2)
N1—C21.322 (2)N4—H4A0.876 (16)
N1—C61.359 (2)N4—H4B0.874 (15)
N2—C21.336 (2)C4—C51.379 (2)
N2—H2A0.874 (15)C5—C61.406 (2)
N2—H2B0.885 (15)C5—H50.9500
N3—C21.360 (2)O1—H1A0.837 (15)
N3—C41.383 (2)O1—H1B0.841 (15)
N3—H30.863 (15)
C2—N1—C6117.07 (13)N2—C2—N3117.60 (14)
C2—N2—H2A121.9 (13)O2—C4—C5126.64 (14)
C2—N2—H2B119.1 (12)O2—C4—N3116.60 (13)
H2A—N2—H2B118.3 (18)C5—C4—N3116.76 (14)
C2—N3—C4122.12 (13)C4—C5—C6118.48 (15)
C2—N3—H3119.7 (12)C4—C5—H5120.8
C4—N3—H3118.0 (12)C6—C5—H5120.8
C6—N4—H4A119.1 (13)N4—C6—N1115.37 (14)
C6—N4—H4B120.7 (13)N4—C6—C5121.59 (15)
H4A—N4—H4B119.6 (19)N1—C6—C5123.04 (14)
N1—C2—N2119.89 (14)H1A—O1—H1B104.1 (18)
N1—C2—N3122.51 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.84 (2)1.88 (2)2.6935 (15)163 (2)
O1—H1B···O2i0.84 (2)1.92 (2)2.7485 (16)170 (2)
N4—H4B···O1ii0.87 (2)2.34 (2)3.0501 (18)139 (2)
N4—H4A···N1iii0.88 (2)2.13 (2)3.0004 (19)173 (2)
N2—H2B···O1iv0.89 (2)2.12 (2)2.9527 (17)158 (2)
N2—H2A···O1v0.87 (2)2.19 (2)3.0605 (18)174 (2)
N3—H3···O2v0.86 (2)1.95 (2)2.8035 (17)173 (2)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x+2, y+2, z; (iv) x+1, y+1, z; (v) x+2, y+1, z+1.
(III) 2,6-diaminopyrimidin-4(3H)-one monohydrate top
Crystal data top
C4H6N4O·H2OF(000) = 608
Mr = 144.14Dx = 1.538 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 353 reflections
a = 17.236 (11) Åθ = 2.4–22.9°
b = 3.987 (3) ŵ = 0.13 mm1
c = 18.717 (12) ÅT = 100 K
β = 104.450 (9)°Lath, colorless
V = 1245.4 (14) Å30.30 × 0.07 × 0.04 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer
1131 independent reflections
Radiation source: fine-focus sealed tube757 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ϕ and ω scansθmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2020
Tmin = 0.964, Tmax = 0.995k = 34
2752 measured reflectionsl = 2221
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0775P)2]
where P = (Fo2 + 2Fc2)/3
1131 reflections(Δ/σ)max = 0.001
112 parametersΔρmax = 0.28 e Å3
7 restraintsΔρmin = 0.37 e Å3
Crystal data top
C4H6N4O·H2OV = 1245.4 (14) Å3
Mr = 144.14Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.236 (11) ŵ = 0.13 mm1
b = 3.987 (3) ÅT = 100 K
c = 18.717 (12) Å0.30 × 0.07 × 0.04 mm
β = 104.450 (9)°
Data collection top
Bruker APEXII CCD
diffractometer
1131 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
757 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.995Rint = 0.055
2752 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0567 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.28 e Å3
1131 reflectionsΔρmin = 0.37 e Å3
112 parameters
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
O20.35162 (12)0.3762 (5)0.27734 (11)0.0264 (6)
N10.32226 (15)0.0450 (6)0.06546 (12)0.0211 (6)
N20.21025 (16)0.2299 (7)0.08148 (14)0.0241 (7)
H2A0.1826 (16)0.305 (8)0.1124 (15)0.029*
H2B0.2024 (18)0.327 (7)0.0369 (12)0.029*
N30.28471 (15)0.0795 (6)0.17834 (13)0.0214 (6)
H30.2443 (14)0.034 (8)0.1980 (16)0.026*
N40.43543 (17)0.3218 (7)0.05329 (14)0.0262 (7)
H4A0.4180 (18)0.270 (8)0.0079 (11)0.031*
H4B0.4732 (16)0.477 (7)0.0704 (16)0.031*
C20.27324 (18)0.0356 (8)0.10741 (15)0.0200 (7)
C40.34835 (17)0.2802 (7)0.21173 (15)0.0205 (7)
C50.40169 (18)0.3600 (8)0.16933 (16)0.0241 (7)
H50.44810.49030.18950.029*
C60.38555 (18)0.2447 (7)0.09648 (15)0.0216 (7)
O10.43094 (14)0.7970 (6)0.38734 (14)0.0364 (7)
H1A0.412 (2)0.699 (9)0.3477 (14)0.044*
H1B0.453 (2)0.970 (7)0.376 (2)0.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0349 (13)0.0343 (14)0.0112 (10)0.0033 (11)0.0084 (9)0.0002 (9)
N10.0269 (14)0.0237 (15)0.0139 (13)0.0056 (12)0.0073 (11)0.0036 (10)
N20.0304 (15)0.0286 (17)0.0155 (13)0.0001 (12)0.0098 (12)0.0001 (11)
N30.0247 (14)0.0264 (16)0.0155 (13)0.0020 (12)0.0096 (11)0.0029 (10)
N40.0314 (16)0.0330 (17)0.0172 (13)0.0031 (13)0.0120 (13)0.0045 (12)
C20.0235 (16)0.0245 (17)0.0120 (15)0.0089 (14)0.0043 (13)0.0054 (12)
C40.0223 (16)0.0219 (17)0.0176 (16)0.0069 (13)0.0056 (13)0.0051 (12)
C50.0240 (16)0.0300 (18)0.0188 (16)0.0019 (15)0.0062 (13)0.0046 (13)
C60.0240 (16)0.0238 (18)0.0194 (16)0.0104 (13)0.0101 (13)0.0079 (13)
O10.0366 (15)0.0299 (15)0.0463 (16)0.0099 (12)0.0174 (13)0.0100 (12)
Geometric parameters (Å, º) top
O2—C41.274 (4)N4—C61.354 (4)
N1—C21.328 (4)N4—H4A0.852 (18)
N1—C61.358 (4)N4—H4B0.897 (18)
N2—C21.323 (4)C4—C51.393 (4)
N2—H2A0.890 (18)C5—C61.400 (4)
N2—H2B0.898 (18)C5—H50.9500
N3—C21.371 (4)O1—H1A0.828 (18)
N3—C41.375 (4)O1—H1B0.835 (19)
N3—H30.883 (18)
C2—N1—C6116.8 (2)N1—C2—N3122.1 (3)
C2—N2—H2A119 (2)O2—C4—N3116.8 (3)
C2—N2—H2B121 (2)O2—C4—C5127.1 (3)
H2A—N2—H2B119 (3)N3—C4—C5116.0 (3)
C2—N3—C4122.7 (3)C4—C5—C6118.7 (3)
C2—N3—H3113 (2)C4—C5—H5120.6
C4—N3—H3123 (2)C6—C5—H5120.6
C6—N4—H4A115 (2)N4—C6—N1116.1 (3)
C6—N4—H4B117 (2)N4—C6—C5120.4 (3)
H4A—N4—H4B124 (3)N1—C6—C5123.5 (3)
N2—C2—N1120.6 (3)H1A—O1—H1B106 (4)
N2—C2—N3117.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.89 (2)2.39 (3)3.115 (4)138 (3)
N2—H2A···O1ii0.89 (2)2.52 (2)3.245 (4)139 (3)
N2—H2B···N1iii0.90 (2)2.05 (2)2.947 (4)177 (3)
N3—H3···O2i0.88 (2)1.93 (2)2.800 (3)168 (3)
N4—H4A···O1iv0.85 (2)2.34 (2)3.124 (4)154 (3)
N4—H4B···O1v0.90 (2)2.08 (2)2.975 (4)174 (3)
O1—H1A···O20.83 (2)1.95 (2)2.742 (3)160 (4)
O1—H1B···N4vi0.84 (2)2.48 (3)3.105 (4)133 (3)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y3/2, z+1/2; (iii) x+1/2, y1/2, z; (iv) x, y+1, z1/2; (v) x+1, y, z+1/2; (vi) x+1, y+1, z+1/2.

Experimental details

(II)(III)
Crystal data
Chemical formulaC4H6N4O·H2OC4H6N4O·H2O
Mr144.14144.14
Crystal system, space groupTriclinic, P1Monoclinic, C2/c
Temperature (K)100100
a, b, c (Å)3.9293 (3), 8.6611 (7), 9.6044 (8)17.236 (11), 3.987 (3), 18.717 (12)
α, β, γ (°)83.111 (5), 88.090 (6), 81.479 (6)90, 104.450 (9), 90
V3)320.88 (4)1245.4 (14)
Z28
Radiation typeMo KαMo Kα
µ (mm1)0.120.13
Crystal size (mm)0.45 × 0.35 × 0.130.30 × 0.07 × 0.04
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Bruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.948, 0.9840.964, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
2138, 1113, 996 2752, 1131, 757
Rint0.0170.055
(sin θ/λ)max1)0.5960.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.112, 1.04 0.056, 0.148, 1.00
No. of reflections11131131
No. of parameters112112
No. of restraints77
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.260.28, 0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) for (II) top
O2—C41.2815 (18)N3—C41.383 (2)
N1—C21.322 (2)N4—C61.335 (2)
N1—C61.359 (2)C4—C51.379 (2)
N2—C21.336 (2)C5—C61.406 (2)
N3—C21.360 (2)
N1—C2—N2119.89 (14)O2—C4—N3116.60 (13)
N2—C2—N3117.60 (14)N4—C6—N1115.37 (14)
O2—C4—C5126.64 (14)N4—C6—C5121.59 (15)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.837 (15)1.881 (16)2.6935 (15)163.4 (19)
O1—H1B···O2i0.841 (15)1.916 (16)2.7485 (16)170.2 (18)
N4—H4B···O1ii0.874 (15)2.336 (18)3.0501 (18)139.0 (16)
N4—H4A···N1iii0.876 (16)2.129 (16)3.0004 (19)173.2 (18)
N2—H2B···O1iv0.885 (15)2.116 (16)2.9527 (17)157.5 (17)
N2—H2A···O1v0.874 (15)2.190 (15)3.0605 (18)173.9 (17)
N3—H3···O2v0.863 (15)1.945 (15)2.8035 (17)173.3 (17)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x+2, y+2, z; (iv) x+1, y+1, z; (v) x+2, y+1, z+1.
Selected geometric parameters (Å, º) for (III) top
O2—C41.274 (4)N3—C41.375 (4)
N1—C21.328 (4)N4—C61.354 (4)
N1—C61.358 (4)C4—C51.393 (4)
N2—C21.323 (4)C5—C61.400 (4)
N3—C21.371 (4)
N2—C2—N1120.6 (3)O2—C4—C5127.1 (3)
N2—C2—N3117.2 (3)N4—C6—N1116.1 (3)
O2—C4—N3116.8 (3)N4—C6—C5120.4 (3)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.890 (18)2.39 (3)3.115 (4)138 (3)
N2—H2A···O1ii0.890 (18)2.52 (2)3.245 (4)139 (3)
N2—H2B···N1iii0.898 (18)2.051 (19)2.947 (4)177 (3)
N3—H3···O2i0.883 (18)1.930 (19)2.800 (3)168 (3)
N4—H4A···O1iv0.852 (18)2.34 (2)3.124 (4)154 (3)
N4—H4B···O1v0.897 (18)2.081 (19)2.975 (4)174 (3)
O1—H1A···O20.828 (18)1.95 (2)2.742 (3)160 (4)
O1—H1B···N4vi0.835 (19)2.48 (3)3.105 (4)133 (3)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y3/2, z+1/2; (iii) x+1/2, y1/2, z; (iv) x, y+1, z1/2; (v) x+1, y, z+1/2; (vi) x+1, y+1, z+1/2.
 

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