Methyl 1-ethyl-7-methyl-4-oxo-1,4-di-hydro-1,8-naphthyridine-3-carboxyl-ate monohydrate.

In the structure of the title compound, C(13)H(14)N(2)O(3)·H(2)O, all atoms of the organic molecule except the terminal methyl group of the ethyl group attached to the N atom of the pyridinone ring are roughly coplanar, with an r.m.s. deviation of 0.0897 Å. In the crystal, C-H⋯O contacts link pairs of naphthyridine mol-ecules into head-to-tail dimers. These are joined by strong O-H⋯O hydrogen bonds from the water molecules into infinite chains along the a axis.

Related literature

For the coordination properties of 1,8-naphthyridine ligands, see: Gavrilova & Bosnich (2004 ▶); Mintert & Sheldrick (1995 ▶). For their biological activity, see: Chen et al. (2001 ▶); Ferrarini et al. (2000 ▶); Roma et al. (2000 ▶). For related structures, see: Deeba, Khan, Zia-ur-Rehman, Çaylak & Şahin (2009 ▶); Deeba, Khan, Zia-ur-Rehman, Şahin & Çaylak (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H14N2O3·H2O

M = 264.28

Monoclinic,

a = 4.6989 (1) Å

b = 23.7246 (7) Å

c = 11.3635 (3) Å

β = 91.646 (1)°

V = 1266.27 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.19 × 0.09 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

12165 measured reflections

3128 independent reflections

2152 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.163

S = 0.98

3128 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004333/sj5191sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004333/sj5191Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004333/sj5191Isup3.cml

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

C13H14N2O3·H2O	F(000) = 560
Mr = 264.28	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3082 reflections
a = 4.6989 (1) Å	θ = 2.5–27.9°
b = 23.7246 (7) Å	µ = 0.10 mm−1
c = 11.3635 (3) Å	T = 296 K
β = 91.646 (1)°	Needle, white
V = 1266.27 (6) Å3	0.19 × 0.09 × 0.07 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2152 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −6→6
12165 measured reflections	k = −29→31
3128 independent reflections	l = −14→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0956P)2 + 0.2245P] where P = (Fo2 + 2Fc2)/3
3128 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.6664 (3)	0.38694 (7)	0.77501 (14)	0.0320 (4)
C2	0.7843 (3)	0.42644 (7)	0.69281 (14)	0.0309 (4)
C3	0.6891 (3)	0.42666 (7)	0.57746 (15)	0.0328 (4)
H3	0.7687	0.4530	0.5274	0.039*
C4	0.3706 (3)	0.35103 (7)	0.60267 (14)	0.0307 (4)
C5	0.4552 (3)	0.34821 (7)	0.72122 (14)	0.0310 (4)
C6	0.3282 (4)	0.30618 (7)	0.78758 (16)	0.0381 (4)
H6	0.3764	0.3023	0.8671	0.046*
C7	0.1332 (4)	0.27070 (7)	0.73569 (16)	0.0398 (4)
H7	0.0481	0.2426	0.7796	0.048*
C8	0.0627 (3)	0.27700 (7)	0.61615 (15)	0.0349 (4)
C9	1.0005 (3)	0.46984 (7)	0.72231 (14)	0.0330 (4)
C10	1.2543 (4)	0.51876 (9)	0.87123 (18)	0.0525 (5)
H10A	1.4364	0.5102	0.8395	0.079*
H10B	1.2713	0.5202	0.9556	0.079*
H10C	1.1896	0.5546	0.8418	0.079*
C11	−0.1477 (4)	0.23821 (8)	0.55685 (18)	0.0448 (4)
H11A	−0.2117	0.2543	0.4833	0.067*
H11B	−0.3074	0.2329	0.6065	0.067*
H11C	−0.0590	0.2025	0.5428	0.067*
C12	0.3991 (4)	0.39784 (8)	0.40625 (15)	0.0421 (4)
H12A	0.4415	0.4358	0.3801	0.051*
H12B	0.1945	0.3926	0.3994	0.051*
C13	0.5409 (5)	0.35647 (9)	0.32742 (18)	0.0560 (6)
H19A	0.4711	0.3616	0.2479	0.084*
H19B	0.4995	0.3188	0.3527	0.084*
H19C	0.7430	0.3625	0.3311	0.084*
N1	0.1777 (3)	0.31671 (6)	0.55030 (12)	0.0346 (3)
N2	0.4905 (3)	0.39199 (6)	0.53125 (12)	0.0331 (3)
O1	0.7306 (3)	0.38354 (6)	0.88110 (11)	0.0449 (4)
O2	1.1179 (3)	0.49770 (6)	0.64973 (12)	0.0529 (4)
O3	1.0520 (3)	0.47558 (6)	0.83641 (11)	0.0483 (4)
O4	0.2506 (4)	0.38795 (8)	0.03949 (15)	0.0678 (5)
H4B	0.099 (7)	0.3912 (13)	−0.025 (3)	0.102*
H4A	0.394 (7)	0.3865 (14)	−0.003 (3)	0.102*

	U11	U22	U33	U12	U13	U23
C1	0.0303 (8)	0.0350 (9)	0.0306 (8)	0.0031 (6)	−0.0017 (6)	0.0001 (7)
C2	0.0285 (8)	0.0320 (8)	0.0322 (8)	0.0010 (6)	−0.0005 (6)	−0.0023 (7)
C3	0.0334 (8)	0.0311 (8)	0.0339 (9)	−0.0009 (6)	0.0000 (6)	0.0004 (7)
C4	0.0294 (8)	0.0304 (8)	0.0321 (8)	0.0033 (6)	−0.0007 (6)	−0.0006 (6)
C5	0.0301 (8)	0.0305 (8)	0.0324 (8)	0.0020 (6)	0.0002 (6)	0.0006 (7)
C6	0.0403 (9)	0.0399 (10)	0.0341 (9)	−0.0007 (7)	0.0005 (7)	0.0025 (7)
C7	0.0406 (9)	0.0368 (9)	0.0421 (10)	−0.0045 (7)	0.0036 (7)	0.0030 (8)
C8	0.0291 (8)	0.0325 (8)	0.0433 (9)	0.0011 (6)	0.0029 (7)	−0.0062 (7)
C9	0.0301 (8)	0.0349 (9)	0.0338 (9)	0.0015 (7)	−0.0019 (6)	−0.0006 (7)
C10	0.0581 (12)	0.0563 (12)	0.0427 (11)	−0.0220 (10)	−0.0066 (9)	−0.0083 (9)
C11	0.0428 (10)	0.0412 (10)	0.0505 (11)	−0.0069 (8)	0.0010 (8)	−0.0079 (8)
C12	0.0480 (10)	0.0434 (10)	0.0342 (9)	−0.0084 (8)	−0.0126 (8)	0.0078 (8)
C13	0.0709 (14)	0.0609 (13)	0.0361 (10)	−0.0118 (11)	−0.0036 (9)	−0.0068 (9)
N1	0.0317 (7)	0.0341 (7)	0.0377 (8)	−0.0003 (6)	−0.0017 (6)	−0.0028 (6)
N2	0.0348 (7)	0.0347 (8)	0.0296 (7)	−0.0011 (6)	−0.0041 (5)	0.0011 (6)
O1	0.0472 (7)	0.0558 (8)	0.0313 (7)	−0.0130 (6)	−0.0069 (5)	0.0055 (6)
O2	0.0583 (8)	0.0615 (9)	0.0388 (7)	−0.0266 (7)	−0.0020 (6)	0.0047 (6)
O3	0.0571 (8)	0.0544 (8)	0.0331 (7)	−0.0227 (6)	−0.0046 (6)	−0.0034 (6)
O4	0.0642 (10)	0.0912 (13)	0.0477 (9)	−0.0087 (9)	−0.0003 (8)	0.0004 (8)

C1—O1	1.237 (2)	C9—O3	1.319 (2)
C1—C2	1.445 (2)	C10—O3	1.445 (2)
C1—C5	1.472 (2)	C10—H10A	0.9600
C2—C3	1.373 (2)	C10—H10B	0.9600
C2—C9	1.478 (2)	C10—H10C	0.9600
C3—N2	1.340 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—N1	1.344 (2)	C11—H11C	0.9600
C4—N2	1.395 (2)	C12—N2	1.479 (2)
C4—C5	1.395 (2)	C12—C13	1.498 (3)
C5—C6	1.395 (2)	C12—H12A	0.9700
C6—C7	1.366 (2)	C12—H12B	0.9700
C6—H6	0.9300	C13—H19A	0.9600
C7—C8	1.397 (2)	C13—H19B	0.9600
C7—H7	0.9300	C13—H19C	0.9600
C8—N1	1.328 (2)	O4—H4B	1.01 (4)
C8—C11	1.497 (2)	O4—H4A	0.84 (3)
C9—O2	1.203 (2)
O1—C1—C2	125.82 (15)	H10A—C10—H10B	109.5
O1—C1—C5	120.43 (15)	O3—C10—H10C	109.5
C2—C1—C5	113.75 (14)	H10A—C10—H10C	109.5
C3—C2—C1	119.95 (14)	H10B—C10—H10C	109.5
C3—C2—C9	114.64 (14)	C8—C11—H11A	109.5
C1—C2—C9	125.38 (14)	C8—C11—H11B	109.5
N2—C3—C2	125.18 (15)	H11A—C11—H11B	109.5
N2—C3—H3	117.4	C8—C11—H11C	109.5
C2—C3—H3	117.4	H11A—C11—H11C	109.5
N1—C4—N2	116.27 (14)	H11B—C11—H11C	109.5
N1—C4—C5	124.62 (15)	N2—C12—C13	113.02 (16)
N2—C4—C5	119.10 (14)	N2—C12—H12A	109.0
C6—C5—C4	116.23 (15)	C13—C12—H12A	109.0
C6—C5—C1	121.03 (15)	N2—C12—H12B	109.0
C4—C5—C1	122.75 (14)	C13—C12—H12B	109.0
C7—C6—C5	119.97 (16)	H12A—C12—H12B	107.8
C7—C6—H6	120.0	C12—C13—H19A	109.5
C5—C6—H6	120.0	C12—C13—H19B	109.5
C6—C7—C8	119.43 (16)	H19A—C13—H19B	109.5
C6—C7—H7	120.3	C12—C13—H19C	109.5
C8—C7—H7	120.3	H19A—C13—H19C	109.5
N1—C8—C7	122.34 (15)	H19B—C13—H19C	109.5
N1—C8—C11	117.19 (16)	C8—N1—C4	117.42 (14)
C7—C8—C11	120.48 (16)	C3—N2—C4	119.21 (14)
O2—C9—O3	122.85 (15)	C3—N2—C12	119.92 (14)
O2—C9—C2	123.56 (15)	C4—N2—C12	120.87 (13)
O3—C9—C2	113.58 (14)	C9—O3—C10	116.29 (14)
O3—C10—H10A	109.5	H4B—O4—H4A	99 (3)
O3—C10—H10B	109.5
O1—C1—C2—C3	−178.42 (16)	C3—C2—C9—O2	−10.8 (2)
C5—C1—C2—C3	2.3 (2)	C1—C2—C9—O2	171.14 (17)
O1—C1—C2—C9	−0.5 (3)	C3—C2—C9—O3	168.67 (15)
C5—C1—C2—C9	−179.75 (14)	C1—C2—C9—O3	−9.3 (2)
C1—C2—C3—N2	−0.6 (2)	C7—C8—N1—C4	0.8 (2)
C9—C2—C3—N2	−178.77 (15)	C11—C8—N1—C4	−178.85 (14)
N1—C4—C5—C6	0.4 (2)	N2—C4—N1—C8	179.33 (14)
N2—C4—C5—C6	−179.72 (14)	C5—C4—N1—C8	−0.8 (2)
N1—C4—C5—C1	−179.66 (14)	C2—C3—N2—C4	−1.5 (2)
N2—C4—C5—C1	0.2 (2)	C2—C3—N2—C12	177.86 (16)
O1—C1—C5—C6	−1.5 (2)	N1—C4—N2—C3	−178.45 (14)
C2—C1—C5—C6	177.77 (14)	C5—C4—N2—C3	1.7 (2)
O1—C1—C5—C4	178.56 (15)	N1—C4—N2—C12	2.2 (2)
C2—C1—C5—C4	−2.1 (2)	C5—C4—N2—C12	−177.68 (15)
C4—C5—C6—C7	0.0 (2)	C13—C12—N2—C3	99.01 (19)
C1—C5—C6—C7	−179.89 (16)	C13—C12—N2—C4	−81.6 (2)
C5—C6—C7—C8	0.0 (3)	O2—C9—O3—C10	1.6 (3)
C6—C7—C8—N1	−0.4 (3)	C2—C9—O3—C10	−177.90 (15)
C6—C7—C8—C11	179.24 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O1i	1.01 (4)	2.02 (4)	2.994 (2)	163 (3)
O4—H4A···O1ii	0.84 (3)	2.09 (3)	2.928 (2)	176 (3)
O4—H4B···O3i	1.01 (4)	2.56 (3)	3.224 (2)	124 (2)
C3—H3···O2iii	0.93	2.40	3.293 (2)	160
C11—H11C···O4iv	0.96	2.59	3.539 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯O1i	1.01 (4)	2.02 (4)	2.994 (2)	163 (3)
O4—H4A⋯O1ii	0.84 (3)	2.09 (3)	2.928 (2)	176 (3)
O4—H4B⋯O3i	1.01 (4)	2.56 (3)	3.224 (2)	124 (2)
C3—H3⋯O2iii	0.93	2.40	3.293 (2)	160
C11—H11C⋯O4iv	0.96	2.59	3.539 (3)	168

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