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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1258.
Published online 2009 May 14. doi:  10.1107/S160053680901678X
PMCID: PMC2969608

1-Benzyl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate

Abstract

In the title compound, C11H11N3O2·H2O, the planes of the triazole and phenyl rings are almost perpendicular to each other [dihedral angle 89.5 (3)°]. The crystal packing is stabilized by strong inter­molecular O—H(...)O and O—H(...)N hydrogen bonds involving the water mol­ecule as both donor and acceptor.

Related literature

For the synthesis of the title compound, see: El Khadem et al. (1968 [triangle]). For the biological activity of triazole compounds, see: Olesen et al. (2003 [triangle]); Tian et al. (2005 [triangle]). For related structures, see: Lin et al. (2008 [triangle]); Xiao et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1258-scheme1.jpg

Experimental

Crystal data

  • C11H11N3O2·H2O
  • M r = 235.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1258-efi1.jpg
  • a = 6.5808 (13) Å
  • b = 7.4995 (15) Å
  • c = 12.337 (3) Å
  • α = 99.87 (4)°
  • β = 93.75 (3)°
  • γ = 91.80 (3)°
  • V = 598.0 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 292 K
  • 0.35 × 0.30 × 0.25 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.963, T max = 0.976
  • 6256 measured reflections
  • 2730 independent reflections
  • 1540 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.174
  • S = 1.05
  • 2730 reflections
  • 156 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.15 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053680901678X/rz2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901678X/rz2316Isup2.hkl

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

Acknowledgments

This work was supported by funds provided by Southeast University for Young Researchers (4007041027). The author thanks Dr Z. R. Qu for her assistance with this work.

supplementary crystallographic information

Comment

Triazole-related molecules have attracted considerable attention due to their biological activities (Olesen et al., 2003; Tian et al., 2005). Recently, we have reported the cerystal structure of a few triazole compounds (Lin et al. 2008; Xiao et al.2008). As an extension of our work on the structural characterization of the triazole-related compounds, we report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), bond lengths and angles have normal values. The dihedral angle between the triazole and phenyl rings is 89.5 (3)°. The packing is stabilized by strong intermolecular O—H···O and O—H···N hydrogen bonds involving the triazole molecules and lattice water molecules (Fig.2; Table 1).

Experimental

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

Refinement

The water and carboxylic H atoms were located from a difference Fourier map but not refined [Uiso(H) = 1.5Ueq(O)]. All other H atoms were fixed geometrically and treated as riding, with C—H = 0.93-0.97 Å and with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Packing diagram of the title compound viewed along the b axis. Intermolecular H bonds are shown as dashed lines.

Crystal data

C11H11N3O2·H2OZ = 2
Mr = 235.24F(000) = 248
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5808 (13) ÅCell parameters from 1986 reflections
b = 7.4995 (15) Åθ = 2.6–27.5°
c = 12.337 (3) ŵ = 0.10 mm1
α = 99.87 (4)°T = 292 K
β = 93.75 (3)°Prism, colourless
γ = 91.80 (3)°0.35 × 0.30 × 0.25 mm
V = 598.0 (2) Å3

Data collection

Rigaku SCXmini diffractometer2730 independent reflections
Radiation source: fine-focus sealed tube1540 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −9→9
Tmin = 0.963, Tmax = 0.976l = −15→15
6256 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0599P)2 + 0.187P] where P = (Fo2 + 2Fc2)/3
2730 reflections(Δ/σ)max < 0.001
156 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.15 e Å3

Special details

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)

xyzUiso*/Ueq
C10.2853 (4)0.2569 (4)0.9216 (2)0.0526 (6)
C20.4367 (4)0.3462 (3)0.86392 (19)0.0484 (6)
C30.6073 (4)0.2769 (3)0.8171 (2)0.0531 (6)
C40.6958 (5)0.0956 (4)0.8063 (3)0.0767 (9)
H4A0.68780.03980.73000.115*
H4B0.62100.02120.84730.115*
H4C0.83590.10840.83460.115*
C50.8767 (4)0.4291 (5)0.7208 (2)0.0715 (8)
H5A0.98510.37380.75860.086*
H5B0.91670.55570.72420.086*
C60.8532 (4)0.3374 (4)0.6016 (2)0.0609 (7)
C70.6735 (6)0.3212 (6)0.5403 (3)0.0988 (12)
H70.55570.36040.57290.119*
C80.6638 (8)0.2462 (7)0.4289 (3)0.1207 (15)
H80.53990.23790.38720.145*
C90.8314 (11)0.1859 (6)0.3814 (3)0.1187 (17)
H90.82390.13270.30730.142*
C101.0096 (9)0.2029 (6)0.4414 (5)0.1221 (16)
H101.12710.16390.40830.146*
C111.0215 (5)0.2769 (5)0.5510 (3)0.0872 (10)
H111.14670.28600.59160.105*
N10.4242 (3)0.5221 (3)0.85113 (17)0.0557 (6)
N20.5786 (4)0.5666 (3)0.79918 (18)0.0624 (6)
N30.6905 (3)0.4179 (3)0.77838 (16)0.0567 (6)
O10.1510 (3)0.3660 (2)0.96493 (16)0.0649 (6)
H10.07760.31251.00120.097*
O20.2875 (4)0.0973 (3)0.9257 (2)0.0921 (8)
O1W0.1065 (3)0.7618 (2)0.91803 (16)0.0709 (6)
H1A0.21370.68760.90380.106*
H1B0.16860.86700.92790.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0594 (16)0.0472 (15)0.0502 (15)−0.0021 (12)0.0062 (12)0.0056 (11)
C20.0559 (15)0.0463 (13)0.0418 (13)−0.0018 (11)0.0051 (11)0.0043 (10)
C30.0562 (15)0.0564 (16)0.0425 (14)−0.0037 (12)0.0033 (11)−0.0016 (11)
C40.079 (2)0.0675 (19)0.079 (2)0.0093 (16)0.0153 (16)−0.0065 (16)
C50.0516 (16)0.108 (2)0.0536 (17)−0.0118 (15)0.0079 (13)0.0128 (16)
C60.0641 (18)0.0689 (18)0.0531 (16)0.0011 (14)0.0143 (14)0.0162 (13)
C70.080 (2)0.148 (4)0.059 (2)0.008 (2)−0.0022 (18)−0.007 (2)
C80.142 (4)0.149 (4)0.062 (2)−0.002 (3)−0.012 (3)0.003 (2)
C90.202 (6)0.096 (3)0.058 (2)−0.009 (3)0.048 (3)0.003 (2)
C100.147 (4)0.114 (3)0.108 (4)0.016 (3)0.072 (3)0.001 (3)
C110.083 (2)0.092 (2)0.090 (3)0.0129 (19)0.0349 (19)0.013 (2)
N10.0634 (14)0.0531 (13)0.0527 (13)−0.0007 (11)0.0119 (10)0.0125 (10)
N20.0677 (15)0.0653 (15)0.0570 (14)−0.0054 (12)0.0119 (11)0.0172 (11)
N30.0560 (13)0.0677 (15)0.0446 (12)−0.0065 (11)0.0065 (10)0.0052 (10)
O10.0683 (13)0.0601 (11)0.0732 (13)0.0066 (10)0.0273 (10)0.0220 (9)
O20.1035 (17)0.0458 (12)0.134 (2)−0.0006 (11)0.0516 (15)0.0183 (12)
O1W0.0752 (13)0.0540 (11)0.0874 (14)−0.0015 (10)0.0318 (11)0.0138 (10)

Geometric parameters (Å, °)

C1—O21.208 (3)C6—C111.359 (4)
C1—O11.302 (3)C7—C81.389 (5)
C1—C21.470 (3)C7—H70.9300
C2—N11.360 (3)C8—C91.338 (6)
C2—C31.372 (3)C8—H80.9300
C3—N31.347 (3)C9—C101.336 (6)
C3—C41.485 (4)C9—H90.9300
C4—H4A0.9600C10—C111.366 (6)
C4—H4B0.9600C10—H100.9300
C4—H4C0.9600C11—H110.9300
C5—N31.463 (3)N1—N21.301 (3)
C5—C61.509 (4)N2—N31.353 (3)
C5—H5A0.9700O1—H10.8200
C5—H5B0.9700O1W—H1A0.9192
C6—C71.352 (4)O1W—H1B0.8630
O2—C1—O1124.7 (2)C11—C6—C5119.0 (3)
O2—C1—C2122.0 (2)C6—C7—C8120.4 (4)
O1—C1—C2113.3 (2)C6—C7—H7119.8
N1—C2—C3109.0 (2)C8—C7—H7119.8
N1—C2—C1122.0 (2)C9—C8—C7120.4 (4)
C3—C2—C1129.0 (2)C9—C8—H8119.8
N3—C3—C2103.5 (2)C7—C8—H8119.8
N3—C3—C4123.9 (2)C10—C9—C8119.3 (4)
C2—C3—C4132.6 (2)C10—C9—H9120.3
C3—C4—H4A109.5C8—C9—H9120.3
C3—C4—H4B109.5C9—C10—C11120.8 (4)
H4A—C4—H4B109.5C9—C10—H10119.6
C3—C4—H4C109.5C11—C10—H10119.6
H4A—C4—H4C109.5C6—C11—C10121.0 (4)
H4B—C4—H4C109.5C6—C11—H11119.5
N3—C5—C6113.3 (2)C10—C11—H11119.5
N3—C5—H5A108.9N2—N1—C2109.1 (2)
C6—C5—H5A108.9N1—N2—N3106.8 (2)
N3—C5—H5B108.9C3—N3—N2111.6 (2)
C6—C5—H5B108.9C3—N3—C5129.6 (3)
H5A—C5—H5B107.7N2—N3—C5118.8 (2)
C7—C6—C11117.9 (3)C1—O1—H1109.5
C7—C6—C5123.0 (3)H1A—O1W—H1B100.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1A···N10.921.962.870 (3)172
O1W—H1B···O2i0.861.882.734 (3)171
O1—H1···O1Wii0.821.752.563 (3)168

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2316).

References

  • El Khadem, H., Mansour, H. A. R. & Meshreki, M. H. (1968). J. Chem. Soc. C, pp. 1329–1331.
  • Lin, J. R., Yao, J. Y. & Zhao, H. (2008). Acta Cryst. E64, o1843. [PMC free article] [PubMed]
  • 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. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem.99, 1646–1652. [PubMed]
  • Xiao, J., Wang, W. X. & Zhao, H. (2008). Acta Cryst. E64, o2085. [PMC free article] [PubMed]

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