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

Wang, G.-G.; Zhao, H.

doi:10.1107/S1600536811056297

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o322

doi:10.1107/S1600536811056297

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

Gai-Gai Wang ^a and Hong Zhao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 23 December 2011; accepted 31 December 2011; online 11 January 2012)

In the title molecule, C₁₁H₁₁N₃O₂, the dihedral angle between the benzene and triazole rings is 76.47 (10)°. The crystal structure exhibits intermolecular 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_r = 217.23
Trigonal, P 3₁
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.115
S = 0.98
2435 reflections
147 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) $[-x+y+1, -x+1, z-{\script{1\over 3}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811056297/lr2044sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811056297/lr2044Isup3.cml

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 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 (Fig. 1), a monohydrate of which has been previously reported (Zhao et al., 2009) .

The dihedral angle between the benzene and tirazole rings is 76.47 (10)°. The crystal structure exhibits intermolecular O—H···N hydrogen bonds which lead to the formation of one-dimensional chains along the [001] direction (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: Xiao et al. (2008); Lin et al. (2008). For structural details of a monohydrate of the title compound, see: Zhao (2009).

Experimental top

The title compound was prepared from azidomethylbenzene according to the reported method (El Khadem et al. 1968). NiCl₂ (1 mmol), NaN₃ (2 mmol) and the title compound (2 mmol) were placed in a thick Pyrex tube (ca 20 cm in length). After addition of 2.0 ml of water, the tube was frozen with liquid N₂, evacuated under vacuum, and sealed with a torch. The tube was heated at 120 °C for 3 days to give colourless prismatic crystals suitable for X-ray analysis.

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

Figures top

	Fig. 1. The molecular structure of the title compound. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Diagram of the molecules linked into one dimensional chains by O—H···N hydrogen bonds.

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

Crystal data top

C₁₁H₁₁N₃O₂	D_x = 1.357 Mg m⁻³
M_r = 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

Data collection top

Rigaku SCXmini diffractometer	2435 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.4°, θ_min = 3.3°
CCD_Profile_fitting scans	h = −13→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.921, T_max = 1.000	l = −11→11
8294 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0487P)²] where P = (F_o² + 2F_c²)/3
2435 reflections	(Δ/σ)_max < 0.001
147 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₁H₁₁N₃O₂	Z = 3
M_r = 217.23	Mo Kα radiation
Trigonal, P3₁	µ = 0.10 mm⁻¹
a = 10.1178 (7) Å	T = 293 K
c = 8.9971 (8) Å	0.20 × 0.18 × 0.15 mm
V = 797.64 (11) Å³

Data collection top

Rigaku SCXmini diffractometer	2435 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1511 reflections with I > 2σ(I)
T_min = 0.921, T_max = 1.000	R_int = 0.049
8294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.115	H-atom parameters constrained
S = 0.98	Δρ_max = 0.13 e Å⁻³
2435 reflections	Δρ_min = −0.16 e Å⁻³
147 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	0.5374 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+y+1, −x+1, z−1/3.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₂
M_r	217.23
Crystal system, space group	Trigonal, P3₁
Temperature (K)	293
a, c (Å)	10.1178 (7), 8.9971 (8)
V (Å³)	797.64 (11)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.921, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8294, 2435, 1511
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.115, 0.98
No. of reflections	2435
No. of parameters	147
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.91	2.721 (3)	171.4

Symmetry code: (i) −x+y+1, −x+1, z−1/3.

Acknowledgements

This work was supported financially by the Southeast University Fund for Young Researchers.

References

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