organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 29 August 2008; accepted 23 September 2008; online 9 October 2008)

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[El Khadem, H., Mansour, H. A. R. & Meshriki, M. H. (1968). J. Chem. Soc. C, pp. 1329-1331.]). For related literature about biological activity of triazole-based compounds, see: Olesen et al. (2003[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.]); Tian et al. (2005[Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646-1652.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N4O4·H2O

  • Mr = 280.25

  • Triclinic, [P \overline 1]

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.965, Tmax = 0.977

  • 6749 measured reflections

  • 2959 independent reflections

  • 1824 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4A⋯O4i 0.96 2.52 3.267 (3) 135
O1W—H1A⋯O1ii 0.85 1.94 2.755 (3) 161
O1W—H1B⋯N1iii 0.93 1.95 2.846 (3) 160
C11—H11⋯O3iv 0.93 2.57 3.423 (4) 153
O2—H2⋯O1Wiv 0.77 (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.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound, showing the crystal structure along the b axis.
5-Methyl-1-(3-nitrobenzyl)-1H-1,2,3-triazole-4-carboxylic acid monohydrate top
Crystal data top
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 top
Rigaku SCXmini
diffractometer
2959 independent reflections
Radiation source: fine-focus sealed tube1824 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1010
Tmin = 0.965, Tmax = 0.977l = 1414
6749 measured reflections
Refinement top
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 = 1.03 w = 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
Crystal data top
C11H10N4O4·H2Oγ = 89.38 (3)°
Mr = 280.25V = 645.5 (2) Å3
Triclinic, P1Z = 2
a = 7.1649 (14) ÅMo Kα radiation
b = 8.2064 (16) ŵ = 0.12 mm1
c = 11.281 (2) ÅT = 293 K
α = 84.88 (3)°0.20 × 0.18 × 0.15 mm
β = 77.70 (2)°
Data collection top
Rigaku SCXmini
diffractometer
2959 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1824 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.977Rint = 0.040
6749 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0643 restraints
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.27 e Å3
2959 reflectionsΔρmin = 0.21 e Å3
186 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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, º) top
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) x1, y+1, z; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC11H10N4O4·H2O
Mr280.25
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.1649 (14), 8.2064 (16), 11.281 (2)
α, β, γ (°)84.88 (3), 77.70 (2), 89.38 (3)
V3)645.5 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.20 × 0.18 × 0.15
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.965, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
6749, 2959, 1824
Rint0.040
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.181, 1.03
No. of reflections2959
No. of parameters186
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.21

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O4i0.962.523.267 (3)135
O1W—H1A···O1ii0.851.942.755 (3)160.5
O1W—H1B···N1iii0.931.952.846 (3)160.3
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) x1, y+1, z; (iv) x, y1, z.
 

Acknowledgements

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

References

First citationEl Khadem, H., Mansour, H. A. R. & Meshriki, M. H. (1968). J. Chem. Soc. C, pp. 1329–1331.  Google Scholar
First citationOlesen, P. H., Sørensen, 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
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTian, 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

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ISSN: 2056-9890
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