2-(4-Eth­oxy­carbon­yl-5-methyl-1H-1,2,3-triazol-1-yl)acetic acid mono­hydrate

Wang, G.-G.; Zhao, H.

doi:10.1107/S1600536810043813

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o3001

https://doi.org/10.1107/S1600536810043813

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2-(4-Ethoxycarbonyl-5-methyl-1H-1,2,3-triazol-1-yl)acetic acid monohydrate

Gai-Gai Wang ^a and Hong Zhao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 20 October 2010; accepted 27 October 2010; online 31 October 2010)

The title compound, C₈H₁₁N₃O₄·H₂O, was synthesized by reaction of 2-azidoacetic acid and ethyl acetylacetate. In the crystal packing, molecules are linked by strong intermolecular 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_r = 231.21
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.189
S = 1.09
2490 reflections
148 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043813/rz2507Isup2.hkl

checkCIF report

Comment top

Triazole derivatives have attracted considerable attention due to their biological activities (Olesen et al., 2003; Tian et al., 2005). Recently, we have reported the crystal structures of a few triazole compounds (Lin et al., 2008; Xiao et al., 2008; Zhao, 2009). As an extension of our work on the structural characterization of triazole derivatives, the crystal structure of the title compound is reported here.

In the molecule of the title compound (Fig. 1) bond lengths and angles have normal values. The crystal packing is stabilized by strong intermolecular O—H···N and O—H···O hydrogen bonds involving the triazole and water molecules (Fig. 2; Table 1) forming double layers parallel to the ab plane.

Related literature top

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

Experimental top

The title compound was prepared from 2-azidoacetic acid according to the reported method (El Khadem et al., 1968). Colourless prismatic crystal suitable for X-ray analysis were obtained by slow evaporation of a 95% ethanol/water solution.

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Version 5.1; Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Version 5.1; Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound, showing the structure along the c axis.

2-(4-Ethoxycarbonyl-5-methyl-1H-1,2,3-triazol-1-yl)acetic acid monohydrate top

Crystal data top

C₈H₁₁N₃O₄·H₂O	F(000) = 976
M_r = 231.21	D_x = 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

Data collection top

Rigaku SCXmini diffractometer	2490 independent reflections
Radiation source: fine-focus sealed tube	1536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.0°, θ_min = 2.7°
CCD_Profile_fitting scans	h = −23→23
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.960, T_max = 0.970	l = −19→19
10958 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0861P)² + 0.6922P] where P = (F_o² + 2F_c²)/3
2490 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₈H₁₁N₃O₄·H₂O	V = 2293.4 (6) Å³
M_r = 231.21	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.6082 (15) Å	µ = 0.11 mm⁻¹
b = 8.2295 (15) Å	T = 295 K
c = 14.986 (2) Å	0.35 × 0.32 × 0.28 mm
β = 92.050 (5)°

Data collection top

Rigaku SCXmini diffractometer	2490 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1536 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.970	R_int = 0.051
10958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.09	Δρ_max = 0.28 e Å⁻³
2490 reflections	Δρ_min = −0.20 e Å⁻³
148 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₈H₁₁N₃O₄·H₂O
M_r	231.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	18.6082 (15), 8.2295 (15), 14.986 (2)
β (°)	92.050 (5)
V (Å³)	2293.4 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.32 × 0.28

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.960, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	10958, 2490, 1536
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.189, 1.09
No. of reflections	2490
No. of parameters	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Version 5.1; Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1F···O2ⁱ	0.93	1.84	2.759 (3)	175.7
O1W—H1E···N3ⁱⁱ	0.92	1.96	2.879 (3)	173.1
O1—H1···O1Wⁱⁱⁱ	0.82	1.75	2.558 (3)	166.9

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

Acknowledgements

This work was supported by financial support from Southeast University for young researchers (grant No. 4007041027).

References

El Khadem, H., Mansour, H. A. R. & Meshreki, M. H. (1968). J. Chem. Soc. C, pp. 1329–1331. Google Scholar
Lin, J. R., Yao, J. Y. & Zhao, H. (2008). Acta Cryst. E64, o1843. Web of Science CSD CrossRef IUCr Journals Google Scholar
Olesen, P. H., Sorensen, A. R., Urso, B., Kurtzhals, P., Bowler, A. N., Ehrbar, U. & Hansen, B. F. (2003). J. Med. Chem. 46, 3333–3341. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646–1652. Web of Science CSD CrossRef PubMed CAS Google Scholar
Xiao, J., Wang, W. X. & Zhao, H. (2008). Acta Cryst. E64, o2085. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, H. (2009). Acta Cryst. E65, o1258. Web of Science CSD CrossRef IUCr Journals Google Scholar