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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2085.
Published online 2008 October 9. doi:  10.1107/S1600536808030584
PMCID: PMC2959515

5-Methyl-1-(3-nitro­benz­yl)-1H-1,2,3-triazole-4-carboxylic acid monohydrate

Abstract

The title compound, C11H10N4O4·H2O, was synthesized from 1-azido­methyl-3-nitro­benzene and ethyl acetyl­acetate. Single-crystal X-ray analysis reveals that the dihedral angle between the triazole and benzene ring planes is 84.80 (2)°. The packing of the mol­ecules is stabilized by strong O—H(...)O hydrogen bonds involving the solvent water mol­ecules as donors and acceptors. The resulting layers are arranged into a three-dimensional framework via weak C—H(...)O inter­actions.

Related literature

For the synthesis of the title compound, see: El Khadem et al. (1968 [triangle]). For related literature about biological activity of triazole-based compounds, see: Olesen et al. (2003 [triangle]); Tian et al. (2005 [triangle]).

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Object name is e-64-o2085-scheme1.jpg

Experimental

Crystal data

  • C11H10N4O4·H2O
  • M r = 280.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2085-efi1.jpg
  • a = 7.1649 (14) Å
  • b = 8.2064 (16) Å
  • c = 11.281 (2) Å
  • α = 84.88 (3)°
  • β = 77.70 (2)°
  • γ = 89.38 (3)°
  • V = 645.5 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 293.1 K
  • 0.20 × 0.18 × 0.15 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.965, T max = 0.977
  • 6749 measured reflections
  • 2959 independent reflections
  • 1824 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.181
  • S = 1.02
  • 2959 reflections
  • 186 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.21 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, global. DOI: 10.1107/S1600536808030584/bh2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030584/bh2192Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Southeast University to HZ.

supplementary crystallographic information

Comment

It is well known that many triazole-related molecules have received much attention due to their biological activities (Olesen et al., 2003; Tian et al., 2005). We report herein the crystal structure of the title compound, (I, Fig. 1). The bond lengths and angles have normal values. The dihedral angle between the triazole and phenyl planes is 84.80 (2)°. The packing of the molecules is stabilized by strong hydrogen bonds (Table 1) between the triazole molecules and lattice water molecules. Meanwhile, the 0D discrete molecules are arranged into a three-dimensional framework via hydrogen bond interactions and weak contacts (Fig. 2).

Experimental

The title compound was prepared from 1-(azidomethyl)-3-nitrobenzene, according to the reported method (EI Khadem et al., 1968), in 70% yield. Colourless prisms of (I) were obtained by slow evaporation of a 95% ethanol/water solution at room temperature.

Refinement

All H atoms were detected in a difference map. Nevertheless, all C-bonded H atoms were placed in calculated positions, and constrained in a riding motion approximation with fixed bond lengths and Uiso parameters: Caryl—H = 0.93 Å, with Uiso(H) = 1.2Ueq(C); Cmethyl—H = 0.96 Å, with Uiso(H) = 1.5Ueq(C); Cmethylene—H = 0.97 Å, with Uiso(H) = 1.2Ueq(C); O—H bonds for the water molecule were constrained to 0.94 Å and 0.85 Å, with Uiso(H) = 1.5Ueq(O1W). Finally, the hydroxyl H atom (H2) was refined freely.

Figures

Fig. 1.
The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Packing diagram of the title compound, showing the crystal structure along the b axis.

Crystal data

C11H10N4O4·H2OZ = 2
Mr = 280.25F(000) = 292
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1649 (14) ÅCell parameters from 5670 reflections
b = 8.2064 (16) Åθ = 3.1–27.5°
c = 11.281 (2) ŵ = 0.12 mm1
α = 84.88 (3)°T = 293 K
β = 77.70 (2)°Prism, colourless
γ = 89.38 (3)°0.20 × 0.18 × 0.15 mm
V = 645.5 (2) Å3

Data collection

Rigaku SCXmini diffractometer2959 independent reflections
Radiation source: fine-focus sealed tube1824 reflections with I > 2σ(I)
graphiteRint = 0.040
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −10→10
Tmin = 0.965, Tmax = 0.977l = −14→14
6749 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) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0847P)2 + 0.0594P] where P = (Fo2 + 2Fc2)/3
2959 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.27 e Å3
3 restraintsΔρmin = −0.21 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.7354 (3)−0.2576 (3)0.1023 (2)0.0489 (6)
C20.8477 (3)−0.1276 (3)0.13603 (19)0.0445 (5)
C30.7947 (3)0.0281 (3)0.16613 (19)0.0453 (5)
C40.6141 (4)0.1200 (3)0.1754 (3)0.0662 (7)
H4A0.54760.11490.25910.099*
H4B0.53570.07250.12810.099*
H4C0.64190.23210.14510.099*
C50.9906 (4)0.2546 (3)0.2222 (2)0.0552 (6)
H5A0.95270.33520.16370.066*
H5B1.12660.26830.21660.066*
C60.8858 (3)0.2880 (3)0.3486 (2)0.0481 (6)
C70.8471 (3)0.4501 (3)0.3709 (2)0.0490 (6)
H70.87870.53340.30830.059*
C80.7616 (3)0.4858 (3)0.4866 (2)0.0525 (6)
C90.7117 (4)0.3678 (4)0.5813 (2)0.0673 (7)
H90.65490.39520.65890.081*
C100.7481 (5)0.2061 (4)0.5582 (2)0.0755 (8)
H100.71390.12330.62090.091*
C110.8352 (4)0.1670 (3)0.4426 (2)0.0634 (7)
H110.85970.05820.42820.076*
N11.0337 (3)−0.1508 (2)0.14233 (18)0.0543 (5)
N21.0999 (3)−0.0190 (2)0.17513 (19)0.0584 (6)
N30.9557 (3)0.0908 (2)0.18882 (17)0.0487 (5)
N40.7247 (3)0.6596 (3)0.5081 (3)0.0710 (7)
O10.8110 (3)−0.3876 (2)0.07308 (19)0.0758 (6)
O20.5593 (3)−0.2220 (3)0.1079 (2)0.0867 (7)
H20.506 (8)−0.295 (6)0.091 (5)0.18 (2)*
O30.7575 (4)0.7611 (3)0.4204 (3)0.1067 (9)
O40.6635 (3)0.6915 (3)0.6118 (2)0.1040 (8)
O1W0.2862 (2)0.5822 (2)0.09151 (18)0.0707 (6)
H1A0.26670.54120.02870.106*
H1B0.18130.65100.11110.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0516 (14)0.0470 (13)0.0509 (14)−0.0009 (11)−0.0142 (10)−0.0120 (10)
C20.0458 (13)0.0474 (12)0.0410 (12)0.0008 (10)−0.0070 (9)−0.0130 (9)
C30.0468 (13)0.0465 (12)0.0426 (12)−0.0009 (10)−0.0066 (9)−0.0113 (9)
C40.0578 (16)0.0592 (16)0.085 (2)0.0136 (13)−0.0185 (13)−0.0156 (14)
C50.0648 (16)0.0449 (13)0.0547 (14)−0.0102 (11)−0.0053 (11)−0.0150 (11)
C60.0523 (14)0.0444 (13)0.0492 (13)−0.0073 (10)−0.0112 (10)−0.0122 (10)
C70.0528 (14)0.0455 (13)0.0500 (13)−0.0056 (11)−0.0120 (10)−0.0087 (10)
C80.0467 (13)0.0567 (14)0.0573 (15)−0.0022 (11)−0.0113 (11)−0.0218 (12)
C90.0653 (17)0.086 (2)0.0511 (15)−0.0053 (15)−0.0088 (12)−0.0182 (14)
C100.093 (2)0.077 (2)0.0520 (17)−0.0084 (17)−0.0088 (14)0.0071 (14)
C110.0809 (19)0.0481 (14)0.0610 (17)−0.0022 (13)−0.0148 (13)−0.0049 (12)
N10.0478 (12)0.0561 (12)0.0629 (13)0.0029 (9)−0.0125 (9)−0.0257 (10)
N20.0509 (12)0.0593 (13)0.0689 (14)0.0023 (10)−0.0136 (10)−0.0255 (11)
N30.0495 (11)0.0448 (11)0.0521 (11)−0.0024 (9)−0.0068 (8)−0.0163 (9)
N40.0608 (14)0.0758 (17)0.0824 (18)0.0047 (12)−0.0141 (12)−0.0429 (15)
O10.0991 (15)0.0526 (11)0.0874 (14)0.0051 (10)−0.0357 (11)−0.0311 (10)
O20.0653 (14)0.0731 (14)0.132 (2)−0.0111 (11)−0.0395 (13)−0.0188 (13)
O30.144 (2)0.0529 (13)0.115 (2)−0.0030 (14)−0.0029 (17)−0.0215 (13)
O40.1111 (19)0.1131 (19)0.0943 (17)0.0254 (15)−0.0156 (14)−0.0625 (15)
O1W0.0632 (12)0.0561 (11)0.0935 (14)−0.0015 (9)−0.0099 (10)−0.0259 (10)

Geometric parameters (Å, °)

C1—O11.230 (3)C7—C81.374 (3)
C1—O21.282 (3)C7—H70.9300
C1—C21.467 (3)C8—C91.366 (4)
C2—N11.360 (3)C8—N41.479 (3)
C2—C31.380 (3)C9—C101.386 (4)
C3—N31.350 (3)C9—H90.9300
C3—C41.479 (3)C10—C111.385 (4)
C4—H4A0.9600C10—H100.9300
C4—H4B0.9600C11—H110.9300
C4—H4C0.9600N1—N21.300 (3)
C5—N31.466 (3)N2—N31.356 (3)
C5—C61.510 (3)N4—O41.210 (3)
C5—H5A0.9700N4—O31.219 (3)
C5—H5B0.9700O2—H20.77 (5)
C6—C111.377 (3)O1W—H1B0.9349
C6—C71.391 (3)O1W—H1A0.8483
O1—C1—O2125.6 (2)C8—C7—H7120.4
O1—C1—C2120.3 (2)C6—C7—H7120.4
O2—C1—C2114.1 (2)C9—C8—C7122.6 (2)
N1—C2—C3109.06 (19)C9—C8—N4119.4 (2)
N1—C2—C1121.1 (2)C7—C8—N4118.0 (2)
C3—C2—C1129.8 (2)C8—C9—C10118.1 (2)
N3—C3—C2103.26 (19)C8—C9—H9121.0
N3—C3—C4123.4 (2)C10—C9—H9121.0
C2—C3—C4133.4 (2)C11—C10—C9120.4 (2)
C3—C4—H4A109.5C11—C10—H10119.8
C3—C4—H4B109.5C9—C10—H10119.8
H4A—C4—H4B109.5C6—C11—C10120.6 (2)
C3—C4—H4C109.5C6—C11—H11119.7
H4A—C4—H4C109.5C10—C11—H11119.7
H4B—C4—H4C109.5N2—N1—C2109.17 (19)
N3—C5—C6114.05 (19)N1—N2—N3106.90 (18)
N3—C5—H5A108.7C3—N3—N2111.60 (18)
C6—C5—H5A108.7C3—N3—C5129.1 (2)
N3—C5—H5B108.7N2—N3—C5119.26 (18)
C6—C5—H5B108.7O4—N4—O3124.3 (3)
H5A—C5—H5B107.6O4—N4—C8117.7 (3)
C11—C6—C7119.2 (2)O3—N4—C8118.0 (2)
C11—C6—C5123.2 (2)C1—O2—H2110 (4)
C7—C6—C5117.5 (2)H1B—O1W—H1A102.8
C8—C7—C6119.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4A···O4i0.962.523.267 (3)135
O1W—H1A···O1ii0.851.942.755 (3)161
O1W—H1B···N1iii0.931.952.846 (3)160
C11—H11···O3iv0.932.573.423 (4)153
O2—H2···O1Wiv0.77 (5)1.88 (5)2.592 (3)153 (6)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2192).

References

  • El Khadem, H., Mansour, H. A. R. & Meshriki, M. H. (1968). J. Chem. Soc. C, pp. 1329–1331.
  • Olesen, P. H., Sørensen, 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]

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