1-Benzyl-5-methyl-1H-1,2,3-triazole-4-carb-oxy-lic acid.

In the title mol-ecule, C(11)H(11)N(3)O(2), the dihedral angle between the benzene and triazole rings is 76.47 (10)°. The crystal structure exhibits inter-molecular O-H⋯N hydrogen bonds, which lead to the formation of helical chains along [001].

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: Xiao et al. (2008 ▶); Lin et al. (2008 ▶). For structural details of a monohydrate of the title compound, see: Zhao (2009 ▶).

Experimental

Crystal data

C11H11N3O2

M = 217.23

Trigonal,

a = 10.1178 (7) Å

c = 8.9971 (8) Å

V = 797.64 (11) Å3

Z = 3

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.921, T max = 1.000

8294 measured reflections

2435 independent reflections

1511 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.115

S = 0.98

2435 reflections

147 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811056297/lr2044sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056297/lr2044Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056297/lr2044Isup3.cml

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

C11H11N3O2	Dx = 1.357 Mg m−3
Mr = 217.23	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 1614 reflections
Hall symbol: P 31	θ = 3.2–27.4°
a = 10.1178 (7) Å	µ = 0.10 mm−1
c = 8.9971 (8) Å	T = 293 K
V = 797.64 (11) Å3	Prism, colourless
Z = 3	0.20 × 0.18 × 0.15 mm
F(000) = 342

Rigaku SCXmini diffractometer	2435 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
graphite	Rint = 0.049
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 3.3°
CCD_Profile_fitting scans	h = −13→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.921, Tmax = 1.000	l = −11→11
8294 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0487P)2] where P = (Fo2 + 2Fc2)/3
2435 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.5374 (3)	0.4836 (3)	−0.0739 (3)	0.0501 (7)
C2	0.4072 (3)	0.4056 (3)	0.0273 (3)	0.0440 (6)
C3	0.2816 (3)	0.4222 (3)	0.0376 (3)	0.0505 (6)
C4	0.2356 (4)	0.5194 (4)	−0.0452 (4)	0.0751 (9)
H4A	0.1509	0.4566	−0.1088	0.113*
H4B	0.3198	0.5920	−0.1042	0.113*
H4C	0.2064	0.5725	0.0239	0.113*
C5	0.0466 (3)	0.2884 (4)	0.2051 (3)	0.0709 (9)
H5A	0.0400	0.3806	0.2120	0.085*
H5B	0.0333	0.2457	0.3042	0.085*
C6	−0.0779 (3)	0.1758 (3)	0.1057 (3)	0.0545 (7)
C7	−0.1626 (4)	0.2174 (4)	0.0197 (4)	0.0715 (9)
H7	−0.1439	0.3172	0.0231	0.086*
C8	−0.2762 (4)	0.1118 (5)	−0.0726 (4)	0.0880 (11)
H8	−0.3333	0.1408	−0.1309	0.106*
C9	−0.3039 (4)	−0.0348 (4)	−0.0778 (4)	0.0846 (11)
H9	−0.3792	−0.1056	−0.1405	0.102*
C10	−0.2215 (4)	−0.0772 (4)	0.0086 (4)	0.0809 (10)
H10	−0.2417	−0.1775	0.0060	0.097*
C11	−0.1093 (4)	0.0259 (4)	0.0992 (4)	0.0675 (8)
H11	−0.0531	−0.0045	0.1573	0.081*
N1	0.3952 (3)	0.3015 (3)	0.1301 (2)	0.0558 (6)
N2	0.2667 (3)	0.2531 (3)	0.2037 (2)	0.0650 (7)
N3	0.1987 (3)	0.3270 (3)	0.1477 (2)	0.0559 (6)
O1	0.6345 (2)	0.4335 (2)	−0.0625 (2)	0.0648 (6)
H1	0.7135	0.4916	−0.1068	0.097*
O2	0.5511 (2)	0.5822 (2)	−0.1573 (2)	0.0758 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0500 (16)	0.0416 (15)	0.0522 (16)	0.0180 (13)	−0.0017 (13)	−0.0012 (13)
C2	0.0462 (15)	0.0386 (13)	0.0462 (14)	0.0204 (12)	−0.0054 (12)	−0.0015 (11)
C3	0.0554 (16)	0.0502 (16)	0.0471 (14)	0.0273 (14)	−0.0109 (14)	−0.0081 (13)
C4	0.084 (2)	0.076 (2)	0.085 (2)	0.054 (2)	−0.0121 (19)	0.0013 (18)
C5	0.0624 (19)	0.102 (2)	0.0573 (18)	0.0480 (19)	0.0045 (14)	−0.0167 (17)
C6	0.0455 (16)	0.077 (2)	0.0447 (15)	0.0331 (15)	0.0101 (13)	−0.0023 (14)
C7	0.059 (2)	0.076 (2)	0.088 (2)	0.0399 (19)	−0.0039 (18)	0.0008 (19)
C8	0.060 (2)	0.120 (3)	0.084 (2)	0.044 (2)	−0.0097 (18)	0.013 (2)
C9	0.056 (2)	0.096 (3)	0.078 (2)	0.019 (2)	0.0024 (17)	−0.012 (2)
C10	0.059 (2)	0.069 (2)	0.103 (3)	0.0232 (19)	0.018 (2)	−0.001 (2)
C11	0.061 (2)	0.079 (2)	0.070 (2)	0.0404 (18)	0.0098 (16)	0.0132 (18)
N1	0.0510 (14)	0.0652 (15)	0.0546 (14)	0.0315 (13)	0.0046 (11)	0.0118 (12)
N2	0.0598 (16)	0.087 (2)	0.0519 (14)	0.0393 (15)	0.0036 (12)	0.0153 (14)
N3	0.0499 (14)	0.0745 (16)	0.0479 (13)	0.0345 (13)	−0.0050 (11)	−0.0088 (12)
O1	0.0511 (11)	0.0661 (13)	0.0756 (14)	0.0281 (11)	0.0128 (10)	0.0121 (11)
O2	0.0828 (15)	0.0580 (13)	0.0785 (15)	0.0292 (11)	0.0135 (12)	0.0270 (12)

C1—O2	1.199 (3)	C6—C7	1.368 (4)
C1—O1	1.316 (3)	C6—C11	1.387 (4)
C1—C2	1.465 (4)	C7—C8	1.387 (5)
C2—N1	1.361 (3)	C7—H7	0.9300
C2—C3	1.366 (4)	C8—C9	1.366 (4)
C3—N3	1.343 (3)	C8—H8	0.9300
C3—C4	1.482 (4)	C9—C10	1.357 (5)
C4—H4A	0.9600	C9—H9	0.9300
C4—H4B	0.9600	C10—C11	1.363 (5)
C4—H4C	0.9600	C10—H10	0.9300
C5—N3	1.479 (3)	C11—H11	0.9300
C5—C6	1.500 (4)	N1—N2	1.315 (3)
C5—H5A	0.9700	N2—N3	1.342 (3)
C5—H5B	0.9700	O1—H1	0.8200
O2—C1—O1	124.8 (3)	C11—C6—C5	120.1 (3)
O2—C1—C2	122.4 (3)	C6—C7—C8	120.4 (3)
O1—C1—C2	112.8 (2)	C6—C7—H7	119.8
N1—C2—C3	108.7 (2)	C8—C7—H7	119.8
N1—C2—C1	123.2 (2)	C9—C8—C7	119.9 (3)
C3—C2—C1	128.1 (2)	C9—C8—H8	120.0
N3—C3—C2	104.3 (2)	C7—C8—H8	120.0
N3—C3—C4	123.8 (3)	C10—C9—C8	119.9 (4)
C2—C3—C4	131.9 (3)	C10—C9—H9	120.1
C3—C4—H4A	109.5	C8—C9—H9	120.1
C3—C4—H4B	109.5	C9—C10—C11	120.6 (4)
H4A—C4—H4B	109.5	C9—C10—H10	119.7
C3—C4—H4C	109.5	C11—C10—H10	119.7
H4A—C4—H4C	109.5	C10—C11—C6	120.7 (3)
H4B—C4—H4C	109.5	C10—C11—H11	119.7
N3—C5—C6	111.1 (2)	C6—C11—H11	119.7
N3—C5—H5A	109.4	N2—N1—C2	108.6 (2)
C6—C5—H5A	109.4	N1—N2—N3	106.9 (2)
N3—C5—H5B	109.4	N2—N3—C3	111.5 (2)
C6—C5—H5B	109.4	N2—N3—C5	118.5 (2)
H5A—C5—H5B	108.0	C3—N3—C5	129.9 (2)
C7—C6—C11	118.5 (3)	C1—O1—H1	109.5
C7—C6—C5	121.4 (3)
O2—C1—C2—N1	−175.1 (3)	C9—C10—C11—C6	0.5 (5)
O1—C1—C2—N1	5.0 (4)	C7—C6—C11—C10	0.3 (4)
O2—C1—C2—C3	4.5 (4)	C5—C6—C11—C10	−179.6 (3)
O1—C1—C2—C3	−175.4 (3)	C3—C2—N1—N2	0.0 (3)
N1—C2—C3—N3	0.3 (3)	C1—C2—N1—N2	179.7 (2)
C1—C2—C3—N3	−179.4 (2)	C2—N1—N2—N3	−0.2 (3)
N1—C2—C3—C4	179.6 (3)	N1—N2—N3—C3	0.4 (3)
C1—C2—C3—C4	0.0 (5)	N1—N2—N3—C5	176.9 (2)
N3—C5—C6—C7	−109.3 (3)	C2—C3—N3—N2	−0.4 (3)
N3—C5—C6—C11	70.6 (3)	C4—C3—N3—N2	−179.9 (2)
C11—C6—C7—C8	−0.5 (5)	C2—C3—N3—C5	−176.4 (2)
C5—C6—C7—C8	179.3 (3)	C4—C3—N3—C5	4.2 (4)
C6—C7—C8—C9	0.0 (5)	C6—C5—N3—N2	−96.9 (3)
C7—C8—C9—C10	0.8 (5)	C6—C5—N3—C3	78.8 (4)
C8—C9—C10—C11	−1.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.91	2.721 (3)	171.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.91	2.721 (3)	171

Symmetry code: (i) .