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

Li, Z.

doi:10.1107/S1600536811033599

organic compounds

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Volume 67| Part 9| September 2011| Page o2541

doi:10.1107/S1600536811033599

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

Zhen Li ^a ^*

^aFaculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, People's Republic of China
^*Correspondence e-mail: lizhen0520@139.com

(Received 6 August 2011; accepted 18 August 2011; online 31 August 2011)

In the crystal structure of the title compound, C₈H₇N₃O·H₂O, adjacent organic molecules 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 molecules are linked together to form a chain along the b axis through O—H⋯O hydrogen bonds. The water chains and the organic molecular tapes are further connected by intermolecular O—H⋯O hydrogen bonds, forming a three-dimensional network. In addition, a π–π stacking interaction between the 1,8-naphthyridine ring systems with an interplanar 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_r = 179.18
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.063
wR(F²) = 0.171
S = 1.00
1432 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811033599/is2766sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811033599/is2766Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811033599/is2766Isup4.cml

checkCIF report

Comment top

The 1,8-naphthyridine and its derivatives have attracted considerable attention as an polydentate nitrogen-donor ligand, since these ligands are linked to metals with several coordination modes such as monodentate and chelating bidentate fashion with short metal-metal bonds (Oskui et al., 1999). In addition, the metal 1,8-naphthyridine complexes can exhibit biocompatibility, interesting catalytic and fluorescence properties (Nakatani et al., 2003; Fang et al., 2004; Sinha et al., 2009). Previously, we have concentrated our investigation on the chemistry of 1,8-naphthyridine derivatives and related metal coordination compounds (Fu et al., 2009, 2010). Herein, we report herein the crystal structure of the title compound. Although the synthesis of the compound 7-amino-1,8-naphthyridin-2(1H)-one has been reported (Newcome et al., 1981), no crystallographic study has been reported on this ligand until now.

The asymmetric unit of the title compound contains a crystallographically independent molecules and one water molecule (Fig. 1), in which the bond lengths and angles are generally within normal ranges in accordance with the corresponding values reported (Goswami et al., 2007). The organic molecule is nearly planar with an r.m.s. deviation of 0.0146 Å. In the crystal structure, adjacent organic molecules are joined together into a one-dimensional tape propagating in the a axis direction (Fig. 2) through N—H···N and N—H···O hydrogen bonds (Table 1). Neighboring water molecules joined together to form a one-dimensional water chain extending along the b axis (Fig. 3) through OW—H···OW hydrogen bonds. These one-dimensional water chains are further connected to the adjacent one-dimensional tape motifs, forming a three-dimensional network (Fig. 3) by intermolecular OW—H···O hydrogen bonds (Table 1). In addition, a π–π stacking interaction between 1,8-naphthyridine rings may further stabilize the structure; the interplanar distance and the centrioid-centrioid distance are 3.246 (1) and 3.825 (2) Å, respectively.

Related literature top

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 top

The 7-amino-1,8-naphthyridin-2(1H)-one was synthesized according to the literature method (Newcome et al., 1981). The colorless crystals of the title compound suitable for X-ray diffraction were obtained by vapor diffusion of diethyl ether into the solution of the product 7-amino-1,8-naphthyridin-2(1H)-one in CH₃CN-MeOH (v:v = 4:1).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The tape structure of the organic molecules propagating in the a axis direction through N—H···N and N—H···O hydrogen bonds.
	Fig. 3. The three-dimensional packing of the title compound viewed along the a axis, showing the hydrogen bonds with dashed lines.

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

Crystal data top

C₈H₇N₃O·H₂O	F(000) = 376
M_r = 179.18	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0752P)²] where P = (F_o² + 2F_c²)/3
1432 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₈H₇N₃O·H₂O	V = 814.34 (13) Å³
M_r = 179.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5413 (9) Å	µ = 0.11 mm⁻¹
b = 17.1560 (16) Å	T = 113 K
c = 4.9954 (4) Å	0.22 × 0.20 × 0.02 mm
β = 95.19 (2)°

Data collection top

Bruker APEX CCD diffractometer	1432 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	906 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.998	R_int = 0.085
6502 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
1432 reflections	Δρ_min = −0.28 e Å⁻³
118 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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₇N₃O·H₂O
M_r	179.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	9.5413 (9), 17.1560 (16), 4.9954 (4)
β (°)	95.19 (2)
V (Å³)	814.34 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.20 × 0.02

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	6502, 1432, 906
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.171, 1.00
No. of reflections	1432
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.28

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.00	2.853 (3)	175.1
N1—H1B···O1ⁱⁱ	0.86	2.28	2.989 (3)	140.2
N3—H1···N2ⁱ	0.86	2.18	3.040 (3)	177.8
O2—H2A···O2ⁱⁱⁱ	0.85	1.93	2.7758 (18)	178.9
O2—H2B···O1	0.85	1.97	2.823 (3)	177.9

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) x, −y+3/2, z+1/2.

Acknowledgements

The author thanks the Science Foundation from the Education Department (grant No. 2010Y004) as well as the Science and Technology Department (grant No. 2010ZC070) of Yunnan Province for supporting this work.

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