7-Amino-1,8-naphthyridin-2(1H)-one monohydrate.

In the crystal structure of the title compound, C(8)H(7)N(3)O·H(2)O, adjacent organic mol-ecules are linked together into a tape along the a axis through N-H⋯N and N-H⋯O hydrogen bonds. On the other hand, water mol-ecules are linked together to form a chain along the b axis through O-H⋯O hydrogen bonds. The water chains and the organic mol-ecular tapes are further connected by inter-molecular O-H⋯O hydrogen bonds, forming a three-dimensional network. In addition, a π-π stacking inter-action between the 1,8-naphthyridine ring systems with an inter-planar separation of 3.246 (1) Å and a centroid-centroid distance of 3.825 (2) Å is observed.

Related literature

For applications of 1,8-naphthyridine and its derivatives in coordination chemistry, see: Oskui et al. (1999 ▶); Nakatani et al. (2003 ▶); Fang et al. (2004 ▶); Sinha et al. (2009 ▶); Fu et al. (2009 ▶, 2010 ▶). For related structures of 1,8-naphthyridine derivatives, see: Goswami et al. (2007 ▶). For the synthesis of the title compound, see: Newcome et al. (1981 ▶).

Experimental

Crystal data

C8H7N3O·H2O

M = 179.18

Monoclinic,

a = 9.5413 (9) Å

b = 17.1560 (16) Å

c = 4.9954 (4) Å

β = 95.19 (2)°

V = 814.34 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.22 × 0.20 × 0.02 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.998

6502 measured reflections

1432 independent reflections

906 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.171

S = 1.00

1432 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033599/is2766sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033599/is2766Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033599/is2766Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811033599/is2766Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H7N3O·H2O	F(000) = 376
Mr = 179.18	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2181 reflections
a = 9.5413 (9) Å	θ = 2.1–27.8°
b = 17.1560 (16) Å	µ = 0.11 mm−1
c = 4.9954 (4) Å	T = 113 K
β = 95.19 (2)°	Prism, colorless
V = 814.34 (13) Å3	0.22 × 0.20 × 0.02 mm
Z = 4

Bruker APEX CCD diffractometer	1432 independent reflections
Radiation source: fine-focus sealed tube	906 reflections with I > 2σ(I)
graphite	Rint = 0.085
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 2.1°
ω scan	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
Tmin = 0.977, Tmax = 0.998	l = −5→5
6502 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0752P)2] where P = (Fo2 + 2Fc2)/3
1432 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.1654 (2)	0.58746 (12)	0.1928 (4)	0.0401 (6)
O2	−0.0186 (2)	0.71471 (12)	0.0843 (4)	0.0461 (7)
H2A	−0.0189	0.7369	0.2365	0.055*
H2B	0.0386	0.6772	0.1179	0.055*
N1	0.8793 (2)	0.52074 (14)	0.2402 (5)	0.0381 (7)
H1A	0.8606	0.4889	0.1089	0.046*
H1B	0.9651	0.5281	0.3036	0.046*
N2	0.6422 (2)	0.54442 (13)	0.2362 (4)	0.0286 (6)
N3	0.4034 (2)	0.56892 (13)	0.2314 (4)	0.0290 (6)
H1	0.3930	0.5370	0.0984	0.035*
C1	0.7755 (3)	0.55862 (17)	0.3454 (6)	0.0333 (7)
C2	0.8036 (3)	0.61017 (18)	0.5674 (6)	0.0364 (8)
H2	0.8978	0.6187	0.6399	0.044*
C3	0.6969 (3)	0.64711 (17)	0.6756 (6)	0.0348 (8)
H3	0.7160	0.6817	0.8229	0.042*
C4	0.5572 (3)	0.63391 (17)	0.5685 (6)	0.0322 (7)
C5	0.4358 (3)	0.66882 (16)	0.6616 (6)	0.0363 (8)
H5	0.4467	0.7030	0.8116	0.044*
C6	0.3041 (3)	0.65478 (17)	0.5423 (6)	0.0344 (8)
H6	0.2250	0.6792	0.6093	0.041*
C7	0.2846 (3)	0.60331 (16)	0.3161 (6)	0.0335 (8)
C8	0.5372 (3)	0.58251 (15)	0.3459 (6)	0.0285 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0361 (12)	0.0370 (14)	0.0470 (14)	0.0041 (9)	0.0037 (10)	0.0006 (10)
O2	0.0615 (15)	0.0333 (13)	0.0421 (14)	0.0105 (11)	−0.0025 (12)	0.0020 (10)
N1	0.0301 (13)	0.0420 (17)	0.0423 (18)	−0.0001 (11)	0.0036 (12)	−0.0050 (13)
N2	0.0308 (13)	0.0253 (13)	0.0296 (15)	−0.0033 (10)	0.0024 (11)	0.0030 (11)
N3	0.0345 (13)	0.0261 (13)	0.0265 (15)	0.0028 (10)	0.0032 (11)	−0.0016 (10)
C1	0.0382 (17)	0.0269 (17)	0.0348 (19)	−0.0047 (14)	0.0025 (14)	0.0073 (14)
C2	0.0387 (17)	0.0306 (18)	0.039 (2)	−0.0079 (13)	−0.0035 (15)	0.0043 (14)
C3	0.0460 (18)	0.0258 (17)	0.0317 (19)	−0.0060 (14)	−0.0013 (15)	0.0006 (13)
C4	0.0431 (17)	0.0230 (16)	0.0305 (19)	0.0002 (13)	0.0042 (14)	0.0037 (13)
C5	0.053 (2)	0.0227 (16)	0.0334 (19)	0.0011 (14)	0.0050 (15)	−0.0003 (14)
C6	0.0389 (17)	0.0268 (17)	0.0385 (19)	0.0054 (13)	0.0099 (15)	0.0023 (14)
C7	0.0392 (17)	0.0243 (16)	0.0377 (19)	0.0039 (13)	0.0066 (15)	0.0055 (14)
C8	0.0364 (16)	0.0192 (15)	0.0300 (18)	−0.0014 (12)	0.0037 (14)	0.0056 (13)

O1—C7	1.273 (3)	C1—C2	1.425 (4)
O2—H2A	0.8500	C2—C3	1.353 (4)
O2—H2B	0.8500	C2—H2	0.9500
N1—C1	1.332 (4)	C3—C4	1.409 (4)
N1—H1A	0.8600	C3—H3	0.9500
N1—H1B	0.8600	C4—C8	1.418 (4)
N2—C8	1.353 (3)	C4—C5	1.419 (4)
N2—C1	1.360 (3)	C5—C6	1.363 (4)
N3—C8	1.370 (3)	C5—H5	0.9500
N3—C7	1.378 (3)	C6—C7	1.433 (4)
N3—H1	0.8600	C6—H6	0.9500
H2A—O2—H2B	102.5	C4—C3—H3	120.2
C1—N1—H1A	120.0	C3—C4—C8	116.9 (3)
C1—N1—H1B	120.0	C3—C4—C5	125.4 (3)
H1A—N1—H1B	120.0	C8—C4—C5	117.6 (3)
C8—N2—C1	116.8 (3)	C6—C5—C4	122.0 (3)
C8—N3—C7	124.0 (3)	C6—C5—H5	119.0
C8—N3—H1	118.0	C4—C5—H5	119.0
C7—N3—H1	118.0	C5—C6—C7	120.2 (3)
N1—C1—N2	117.2 (3)	C5—C6—H6	119.9
N1—C1—C2	121.1 (3)	C7—C6—H6	119.9
N2—C1—C2	121.7 (3)	O1—C7—N3	118.9 (3)
C3—C2—C1	120.5 (3)	O1—C7—C6	124.0 (3)
C3—C2—H2	119.8	N3—C7—C6	117.1 (3)
C1—C2—H2	119.8	N2—C8—N3	116.4 (3)
C2—C3—C4	119.5 (3)	N2—C8—C4	124.5 (3)
C2—C3—H3	120.2	N3—C8—C4	119.2 (3)
C8—N2—C1—N1	179.3 (3)	C8—N3—C7—C6	−1.6 (4)
C8—N2—C1—C2	1.0 (4)	C5—C6—C7—O1	−179.6 (3)
N1—C1—C2—C3	−178.7 (3)	C5—C6—C7—N3	0.9 (4)
N2—C1—C2—C3	−0.4 (4)	C1—N2—C8—N3	178.8 (2)
C1—C2—C3—C4	0.4 (5)	C1—N2—C8—C4	−1.7 (4)
C2—C3—C4—C8	−1.0 (4)	C7—N3—C8—N2	−179.4 (2)
C2—C3—C4—C5	−179.8 (3)	C7—N3—C8—C4	1.1 (4)
C3—C4—C5—C6	178.1 (3)	C3—C4—C8—N2	1.7 (4)
C8—C4—C5—C6	−0.7 (4)	C5—C4—C8—N2	−179.4 (3)
C4—C5—C6—C7	0.1 (4)	C3—C4—C8—N3	−178.8 (2)
C8—N3—C7—O1	179.0 (2)	C5—C4—C8—N3	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.00	2.853 (3)	175.
N1—H1B···O1ii	0.86	2.28	2.989 (3)	140.
N3—H1···N2i	0.86	2.18	3.040 (3)	178.
O2—H2A···O2iii	0.85	1.93	2.7758 (18)	179.
O2—H2B···O1	0.85	1.97	2.823 (3)	178.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.00	2.853 (3)	175
N1—H1B⋯O1ii	0.86	2.28	2.989 (3)	140
N3—H1⋯N2i	0.86	2.18	3.040 (3)	178
O2—H2A⋯O2iii	0.85	1.93	2.7758 (18)	179
O2—H2B⋯O1	0.85	1.97	2.823 (3)	178

Symmetry codes: (i) ; (ii) ; (iii) .