2-(4-Eth-oxy-carbon-yl-5-methyl-1H-1,2,3-triazol-1-yl)acetic acid mono-hydrate.

The title compound, C(8)H(11)N(3)O(4)·H(2)O, was synthesized by reaction of 2-azido-acetic acid and ethyl acetyl-acetate. In the crystal packing, mol-ecules are linked by strong inter-molecular O-H⋯N and O-H⋯O hydrogen bonds into double layers parallel to the ab plane.

Related literature

For the biological activities of triazole derivatives, see: Olesen et al. (2003 ▶); Tian et al. (2005 ▶). For the synthesis, see: El Khadem et al. (1968 ▶). For related structures, see: Lin et al. (2008 ▶); Xiao et al. (2008 ▶); Zhao (2009 ▶).

Experimental

Crystal data

C8H11N3O4·H2O

M = 231.21

Monoclinic,

a = 18.6082 (15) Å

b = 8.2295 (15) Å

c = 14.986 (2) Å

β = 92.050 (5)°

V = 2293.4 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.35 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.960, T max = 0.970

10958 measured reflections

2490 independent reflections

1536 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.189

S = 1.09

2490 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043813/rz2507sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043813/rz2507Isup2.hkl

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

C8H11N3O4·H2O	F(000) = 976
Mr = 231.21	Dx = 1.339 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2099 reflections
a = 18.6082 (15) Å	θ = 2.7–27.5°
b = 8.2295 (15) Å	µ = 0.11 mm−1
c = 14.986 (2) Å	T = 295 K
β = 92.050 (5)°	Prism, colourless
V = 2293.4 (6) Å3	0.35 × 0.32 × 0.28 mm
Z = 8

Rigaku SCXmini diffractometer	2490 independent reflections
Radiation source: fine-focus sealed tube	1536 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 13.6612 pixels mm-1	θmax = 27.0°, θmin = 2.7°
CCD_Profile_fitting scans	h = −23→23
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.960, Tmax = 0.970	l = −19→19
10958 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0861P)2 + 0.6922P] where P = (Fo2 + 2Fc2)/3
2490 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.81442 (14)	−0.2524 (3)	0.37722 (19)	0.0552 (6)
C2	0.87508 (14)	−0.2098 (3)	0.44180 (18)	0.0611 (7)
H2A	0.8554	−0.1835	0.4991	0.073*
H2B	0.9059	−0.3041	0.4502	0.073*
C3	0.90266 (14)	0.0868 (3)	0.41202 (18)	0.0557 (6)
C4	0.83230 (16)	0.1554 (4)	0.4359 (3)	0.0936 (12)
H4A	0.7981	0.1402	0.3871	0.140*
H4B	0.8376	0.2694	0.4481	0.140*
H4C	0.8156	0.1012	0.4880	0.140*
C5	0.96537 (13)	0.1568 (3)	0.38496 (18)	0.0542 (6)
C6	0.98182 (15)	0.3313 (3)	0.3765 (2)	0.0631 (7)
N1	0.91816 (11)	−0.0742 (2)	0.41279 (14)	0.0552 (6)
N2	0.98618 (12)	−0.1025 (3)	0.38793 (17)	0.0658 (6)
N3	1.01479 (11)	0.0386 (2)	0.37055 (17)	0.0629 (6)
O1	0.77303 (11)	−0.3646 (2)	0.41090 (13)	0.0687 (6)
H1	0.7401	−0.3861	0.3750	0.103*
O2	0.80534 (12)	−0.1933 (3)	0.30435 (15)	0.0828 (7)
O3	0.93857 (12)	0.4367 (2)	0.38956 (19)	0.0963 (8)
O4	1.04841 (10)	0.3565 (2)	0.35401 (16)	0.0787 (7)
O1W	0.66222 (12)	0.5429 (3)	0.31857 (17)	0.1016 (9)
H1E	0.6157	0.5328	0.3366	0.152*
H1F	0.6724	0.4673	0.2751	0.152*
C7	1.07274 (18)	0.5254 (4)	0.3491 (3)	0.0975 (13)
H7A	1.0559	0.5733	0.2931	0.117*
H7B	1.0531	0.5877	0.3975	0.117*
C8	1.1478 (2)	0.5300 (5)	0.3554 (4)	0.1357 (19)
H8A	1.1645	0.4680	0.4063	0.204*
H8B	1.1635	0.6406	0.3620	0.204*
H8C	1.1669	0.4846	0.3022	0.204*

	U11	U22	U33	U12	U13	U23
C1	0.0569 (15)	0.0444 (13)	0.0649 (16)	−0.0084 (11)	0.0111 (12)	−0.0044 (12)
C2	0.0590 (16)	0.0525 (15)	0.0720 (17)	−0.0113 (12)	0.0030 (13)	0.0027 (13)
C3	0.0483 (14)	0.0482 (14)	0.0705 (16)	−0.0026 (11)	0.0034 (12)	−0.0085 (12)
C4	0.0614 (19)	0.068 (2)	0.154 (3)	−0.0031 (16)	0.031 (2)	−0.017 (2)
C5	0.0462 (14)	0.0448 (13)	0.0713 (16)	−0.0019 (11)	−0.0012 (12)	−0.0070 (12)
C6	0.0556 (16)	0.0482 (14)	0.085 (2)	−0.0050 (13)	−0.0067 (14)	−0.0044 (13)
N1	0.0482 (12)	0.0445 (11)	0.0729 (14)	−0.0073 (9)	0.0042 (10)	−0.0021 (10)
N2	0.0493 (13)	0.0470 (12)	0.1013 (18)	−0.0040 (10)	0.0066 (12)	0.0008 (12)
N3	0.0462 (12)	0.0470 (12)	0.0956 (17)	−0.0039 (9)	0.0059 (11)	−0.0033 (11)
O1	0.0652 (12)	0.0675 (12)	0.0739 (12)	−0.0251 (10)	0.0078 (9)	−0.0006 (10)
O2	0.0906 (16)	0.0848 (15)	0.0724 (13)	−0.0321 (12)	−0.0074 (11)	0.0157 (12)
O3	0.0744 (15)	0.0479 (11)	0.167 (2)	0.0032 (11)	0.0108 (15)	−0.0080 (13)
O4	0.0532 (11)	0.0499 (11)	0.1330 (19)	−0.0134 (9)	0.0037 (11)	0.0032 (11)
O1W	0.0557 (13)	0.122 (2)	0.128 (2)	−0.0154 (12)	0.0168 (13)	−0.0639 (16)
C7	0.075 (2)	0.0488 (17)	0.168 (4)	−0.0179 (15)	−0.011 (2)	0.014 (2)
C8	0.095 (3)	0.094 (3)	0.216 (5)	−0.049 (2)	−0.031 (3)	0.050 (3)

C1—O2	1.202 (3)	C6—O3	1.204 (3)
C1—O1	1.315 (3)	C6—O4	1.312 (3)
C1—C2	1.502 (4)	N1—N2	1.352 (3)
C2—N1	1.450 (3)	N2—N3	1.307 (3)
C2—H2A	0.9700	O1—H1	0.8200
C2—H2B	0.9700	O4—C7	1.465 (3)
C3—N1	1.356 (3)	O1W—H1E	0.9194
C3—C5	1.375 (3)	O1W—H1F	0.9251
C3—C4	1.481 (4)	C7—C8	1.396 (5)
C4—H4A	0.9600	C7—H7A	0.9700
C4—H4B	0.9600	C7—H7B	0.9700
C4—H4C	0.9600	C8—H8A	0.9600
C5—N3	1.361 (3)	C8—H8B	0.9600
C5—C6	1.475 (3)	C8—H8C	0.9600
O2—C1—O1	124.6 (3)	O3—C6—C5	123.0 (3)
O2—C1—C2	124.7 (2)	O4—C6—C5	112.1 (2)
O1—C1—C2	110.7 (2)	N2—N1—C3	111.5 (2)
N1—C2—C1	113.4 (2)	N2—N1—C2	118.9 (2)
N1—C2—H2A	108.9	C3—N1—C2	129.4 (2)
C1—C2—H2A	108.9	N3—N2—N1	107.1 (2)
N1—C2—H2B	108.9	N2—N3—C5	108.7 (2)
C1—C2—H2B	108.9	C1—O1—H1	109.5
H2A—C2—H2B	107.7	C6—O4—C7	117.3 (2)
N1—C3—C5	103.2 (2)	H1E—O1W—H1F	111.4
N1—C3—C4	124.1 (2)	C8—C7—O4	109.4 (3)
C5—C3—C4	132.7 (2)	C8—C7—H7A	109.8
C3—C4—H4A	109.5	O4—C7—H7A	109.8
C3—C4—H4B	109.5	C8—C7—H7B	109.8
H4A—C4—H4B	109.5	O4—C7—H7B	109.8
C3—C4—H4C	109.5	H7A—C7—H7B	108.2
H4A—C4—H4C	109.5	C7—C8—H8A	109.5
H4B—C4—H4C	109.5	C7—C8—H8B	109.5
N3—C5—C3	109.4 (2)	H8A—C8—H8B	109.5
N3—C5—C6	122.6 (2)	C7—C8—H8C	109.5
C3—C5—C6	127.9 (2)	H8A—C8—H8C	109.5
O3—C6—O4	124.8 (3)	H8B—C8—H8C	109.5
O2—C1—C2—N1	7.1 (4)	C5—C3—N1—C2	175.1 (3)
O1—C1—C2—N1	−173.6 (2)	C4—C3—N1—C2	−5.1 (4)
N1—C3—C5—N3	0.2 (3)	C1—C2—N1—N2	−110.4 (3)
C4—C3—C5—N3	−179.6 (3)	C1—C2—N1—C3	74.9 (3)
N1—C3—C5—C6	−176.4 (3)	C3—N1—N2—N3	−0.4 (3)
C4—C3—C5—C6	3.8 (5)	C2—N1—N2—N3	−176.0 (2)
N3—C5—C6—O3	−179.6 (3)	N1—N2—N3—C5	0.5 (3)
C3—C5—C6—O3	−3.4 (5)	C3—C5—N3—N2	−0.4 (3)
N3—C5—C6—O4	−0.1 (4)	C6—C5—N3—N2	176.4 (3)
C3—C5—C6—O4	176.1 (3)	O3—C6—O4—C7	3.4 (5)
C5—C3—N1—N2	0.1 (3)	C5—C6—O4—C7	−176.1 (3)
C4—C3—N1—N2	179.9 (3)	C6—O4—C7—C8	159.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1F···O2i	0.93	1.84	2.759 (3)	176
O1W—H1E···N3ii	0.92	1.96	2.879 (3)	173
O1—H1···O1Wiii	0.82	1.75	2.558 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1F⋯O2i	0.93	1.84	2.759 (3)	176
O1W—H1E⋯N3ii	0.92	1.96	2.879 (3)	173
O1—H1⋯O1Wiii	0.82	1.75	2.558 (3)	167

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