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

Zhao, H.

doi:10.1107/S160053680901678X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1258

doi:10.1107/S160053680901678X

Open

access

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

Hong Zhao ^a ^*

^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 25 April 2009; accepted 5 May 2009; online 14 May 2009)

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 ). For the biological activity of triazole compounds, see: Olesen et al. (2003 ); Tian et al. (2005 ). For related structures, see: Lin et al. (2008 ); Xiao et al. (2008 ).

Experimental

Crystal data

C₁₁H₁₁N₃O₂·H₂O
M_r = 235.24
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.174
S = 1.05
2730 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯N1	0.92	1.96	2.870 (3)	172
O1W—H1B⋯O2ⁱ	0.86	1.88	2.734 (3)	171
O1—H1⋯O1Wⁱⁱ	0.82	1.75	2.563 (3)	168
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+2.

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

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

	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.

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

Crystal data top

C₁₁H₁₁N₃O₂·H₂O	Z = 2
M_r = 235.24	F(000) = 248
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5808 (13) Å	Cell parameters from 1986 reflections
b = 7.4995 (15) Å	θ = 2.6–27.5°
c = 12.337 (3) Å	µ = 0.10 mm⁻¹
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 top

Rigaku SCXmini diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.963, T_max = 0.976	l = −15→15
6256 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0599P)² + 0.187P] where P = (F_o² + 2F_c²)/3
2730 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₁H₁₁N₃O₂·H₂O	γ = 91.80 (3)°
M_r = 235.24	V = 598.0 (2) Å³
Triclinic, P1	Z = 2
a = 6.5808 (13) Å	Mo Kα radiation
b = 7.4995 (15) Å	µ = 0.10 mm⁻¹
c = 12.337 (3) Å	T = 292 K
α = 99.87 (4)°	0.35 × 0.30 × 0.25 mm
β = 93.75 (3)°

Data collection top

Rigaku SCXmini diffractometer	2730 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1540 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.976	R_int = 0.042
6256 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
2730 reflections	Δρ_min = −0.15 e Å⁻³
156 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	0.2853 (4)	0.2569 (4)	0.9216 (2)	0.0526 (6)
C2	0.4367 (4)	0.3462 (3)	0.86392 (19)	0.0484 (6)
C3	0.6073 (4)	0.2769 (3)	0.8171 (2)	0.0531 (6)
C4	0.6958 (5)	0.0956 (4)	0.8063 (3)	0.0767 (9)
H4A	0.6878	0.0398	0.7300	0.115*
H4B	0.6210	0.0212	0.8473	0.115*
H4C	0.8359	0.1084	0.8346	0.115*
C5	0.8767 (4)	0.4291 (5)	0.7208 (2)	0.0715 (8)
H5A	0.9851	0.3738	0.7586	0.086*
H5B	0.9167	0.5557	0.7242	0.086*
C6	0.8532 (4)	0.3374 (4)	0.6016 (2)	0.0609 (7)
C7	0.6735 (6)	0.3212 (6)	0.5403 (3)	0.0988 (12)
H7	0.5557	0.3604	0.5729	0.119*
C8	0.6638 (8)	0.2462 (7)	0.4289 (3)	0.1207 (15)
H8	0.5399	0.2379	0.3872	0.145*
C9	0.8314 (11)	0.1859 (6)	0.3814 (3)	0.1187 (17)
H9	0.8239	0.1327	0.3073	0.142*
C10	1.0096 (9)	0.2029 (6)	0.4414 (5)	0.1221 (16)
H10	1.1271	0.1639	0.4083	0.146*
C11	1.0215 (5)	0.2769 (5)	0.5510 (3)	0.0872 (10)
H11	1.1467	0.2860	0.5916	0.105*
N1	0.4242 (3)	0.5221 (3)	0.85113 (17)	0.0557 (6)
N2	0.5786 (4)	0.5666 (3)	0.79918 (18)	0.0624 (6)
N3	0.6905 (3)	0.4179 (3)	0.77838 (16)	0.0567 (6)
O1	0.1510 (3)	0.3660 (2)	0.96493 (16)	0.0649 (6)
H1	0.0776	0.3125	1.0012	0.097*
O2	0.2875 (4)	0.0973 (3)	0.9257 (2)	0.0921 (8)
O1W	0.1065 (3)	0.7618 (2)	0.91803 (16)	0.0709 (6)
H1A	0.2137	0.6876	0.9038	0.106*
H1B	0.1686	0.8670	0.9279	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0594 (16)	0.0472 (15)	0.0502 (15)	−0.0021 (12)	0.0062 (12)	0.0056 (11)
C2	0.0559 (15)	0.0463 (13)	0.0418 (13)	−0.0018 (11)	0.0051 (11)	0.0043 (10)
C3	0.0562 (15)	0.0564 (16)	0.0425 (14)	−0.0037 (12)	0.0033 (11)	−0.0016 (11)
C4	0.079 (2)	0.0675 (19)	0.079 (2)	0.0093 (16)	0.0153 (16)	−0.0065 (16)
C5	0.0516 (16)	0.108 (2)	0.0536 (17)	−0.0118 (15)	0.0079 (13)	0.0128 (16)
C6	0.0641 (18)	0.0689 (18)	0.0531 (16)	0.0011 (14)	0.0143 (14)	0.0162 (13)
C7	0.080 (2)	0.148 (4)	0.059 (2)	0.008 (2)	−0.0022 (18)	−0.007 (2)
C8	0.142 (4)	0.149 (4)	0.062 (2)	−0.002 (3)	−0.012 (3)	0.003 (2)
C9	0.202 (6)	0.096 (3)	0.058 (2)	−0.009 (3)	0.048 (3)	0.003 (2)
C10	0.147 (4)	0.114 (3)	0.108 (4)	0.016 (3)	0.072 (3)	0.001 (3)
C11	0.083 (2)	0.092 (2)	0.090 (3)	0.0129 (19)	0.0349 (19)	0.013 (2)
N1	0.0634 (14)	0.0531 (13)	0.0527 (13)	−0.0007 (11)	0.0119 (10)	0.0125 (10)
N2	0.0677 (15)	0.0653 (15)	0.0570 (14)	−0.0054 (12)	0.0119 (11)	0.0172 (11)
N3	0.0560 (13)	0.0677 (15)	0.0446 (12)	−0.0065 (11)	0.0065 (10)	0.0052 (10)
O1	0.0683 (13)	0.0601 (11)	0.0732 (13)	0.0066 (10)	0.0273 (10)	0.0220 (9)
O2	0.1035 (17)	0.0458 (12)	0.134 (2)	−0.0006 (11)	0.0516 (15)	0.0183 (12)
O1W	0.0752 (13)	0.0540 (11)	0.0874 (14)	−0.0015 (10)	0.0318 (11)	0.0138 (10)

Geometric parameters (Å, º) top

C1—O2	1.208 (3)	C6—C11	1.359 (4)
C1—O1	1.302 (3)	C7—C8	1.389 (5)
C1—C2	1.470 (3)	C7—H7	0.9300
C2—N1	1.360 (3)	C8—C9	1.338 (6)
C2—C3	1.372 (3)	C8—H8	0.9300
C3—N3	1.347 (3)	C9—C10	1.336 (6)
C3—C4	1.485 (4)	C9—H9	0.9300
C4—H4A	0.9600	C10—C11	1.366 (6)
C4—H4B	0.9600	C10—H10	0.9300
C4—H4C	0.9600	C11—H11	0.9300
C5—N3	1.463 (3)	N1—N2	1.301 (3)
C5—C6	1.509 (4)	N2—N3	1.353 (3)
C5—H5A	0.9700	O1—H1	0.8200
C5—H5B	0.9700	O1W—H1A	0.9192
C6—C7	1.352 (4)	O1W—H1B	0.8630

O2—C1—O1	124.7 (2)	C11—C6—C5	119.0 (3)
O2—C1—C2	122.0 (2)	C6—C7—C8	120.4 (4)
O1—C1—C2	113.3 (2)	C6—C7—H7	119.8
N1—C2—C3	109.0 (2)	C8—C7—H7	119.8
N1—C2—C1	122.0 (2)	C9—C8—C7	120.4 (4)
C3—C2—C1	129.0 (2)	C9—C8—H8	119.8
N3—C3—C2	103.5 (2)	C7—C8—H8	119.8
N3—C3—C4	123.9 (2)	C10—C9—C8	119.3 (4)
C2—C3—C4	132.6 (2)	C10—C9—H9	120.3
C3—C4—H4A	109.5	C8—C9—H9	120.3
C3—C4—H4B	109.5	C9—C10—C11	120.8 (4)
H4A—C4—H4B	109.5	C9—C10—H10	119.6
C3—C4—H4C	109.5	C11—C10—H10	119.6
H4A—C4—H4C	109.5	C6—C11—C10	121.0 (4)
H4B—C4—H4C	109.5	C6—C11—H11	119.5
N3—C5—C6	113.3 (2)	C10—C11—H11	119.5
N3—C5—H5A	108.9	N2—N1—C2	109.1 (2)
C6—C5—H5A	108.9	N1—N2—N3	106.8 (2)
N3—C5—H5B	108.9	C3—N3—N2	111.6 (2)
C6—C5—H5B	108.9	C3—N3—C5	129.6 (3)
H5A—C5—H5B	107.7	N2—N3—C5	118.8 (2)
C7—C6—C11	117.9 (3)	C1—O1—H1	109.5
C7—C6—C5	123.0 (3)	H1A—O1W—H1B	100.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···N1	0.92	1.96	2.870 (3)	172
O1W—H1B···O2ⁱ	0.86	1.88	2.734 (3)	171
O1—H1···O1Wⁱⁱ	0.82	1.75	2.563 (3)	168

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₂·H₂O
M_r	235.24
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	6.5808 (13), 7.4995 (15), 12.337 (3)
α, β, γ (°)	99.87 (4), 93.75 (3), 91.80 (3)
V (Å³)	598.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.963, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	6256, 2730, 1540
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.174, 1.05
No. of reflections	2730
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···N1	0.92	1.96	2.870 (3)	171.6
O1W—H1B···O2ⁱ	0.86	1.88	2.734 (3)	170.7
O1—H1···O1Wⁱⁱ	0.82	1.75	2.563 (3)	168.4

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

Acknowledgements

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.

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