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 ▶). 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,

• 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) ų

• 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[F ² > 2σ(F ²)] = 0.064

• wR(F ²) = 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

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.

Supplementary Material

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

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) ; (ii) .

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 [U_iso(H) = 1.5U_eq(O)]. All other H atoms were fixed geometrically and treated as riding, with C—H = 0.93-0.97 Å and with U_iso(H) = 1.2U_eq(C) or 1.5 U_eq(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·H2O	Z = 2
Mr = 235.24	F(000) = 248
Triclinic, P1	Dx = 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

Rigaku SCXmini diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.963, Tmax = 0.976	l = −15→15
6256 measured reflections

Refinement

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(Fo2) + (0.0599P)2 + 0.187P] where P = (Fo2 + 2Fc2)/3
2730 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.