Methyl 2-methyl-2H-1,2,3-triazole-4-carboxyl-ate.

In the title compound, C(5)H(7)N(3)O(2), all non-H atoms lie in a common plane, with a maximum deviation of 0.061 (2)° for the ester methyl C atom. The structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to the applications of triazoles and their derivatives, see: Abu-Orabi et al. (1989 ▶); Fan & Katritzky (1996 ▶); Dehne (1994 ▶); Wang et al. (1998 ▶). For a related structure, see: Prabakaran et al. (2009 ▶).

Experimental

Crystal data

C5H7N3O2

M = 141.14

Monoclinic,

a = 3.9482 (10) Å

b = 7.9549 (15) Å

c = 21.655 (4) Å

β = 92.05 (2)°

V = 679.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 290 K

0.30 × 0.20 × 0.10 mm

Data collection

Oxford Xcalibur Eos(Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlisPro RED; Oxford Diffraction, 2009 ▶) T min = 0.926, T max = 0.989

7464 measured reflections

1262 independent reflections

910 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.07

1262 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlisPro CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro CCD; data reduction: CrysAlisPro RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024829/bt2973sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024829/bt2973Isup2.hkl

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

C5H7N3O2	F(000) = 296
Mr = 141.14	Dx = 1.379 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 783 reflections
a = 3.9482 (10) Å	θ = 2.0–21.4°
b = 7.9549 (15) Å	µ = 0.11 mm−1
c = 21.655 (4) Å	T = 290 K
β = 92.05 (2)°	Plate, colorless
V = 679.7 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Oxford Xcalibur Eos(Nova) CCD detector diffractometer	1262 independent reflections
Radiation source: Enhance (Mo) X-ray Source	910 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 25.5°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −4→4
Tmin = 0.926, Tmax = 0.989	k = −9→9
7464 measured reflections	l = −26→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.0659P] where P = (Fo2 + 2Fc2)/3
1262 reflections	(Δ/σ)max < 0.001
93 parameters	Δρmax = 0.19 e Å−3
0 restraints	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.

	x	y	z	Uiso*/Ueq
N1	0.2453 (4)	0.56849 (18)	0.43005 (7)	0.0442 (4)
N2	0.3338 (4)	0.71794 (19)	0.45090 (7)	0.0449 (4)
N3	0.4803 (5)	0.8185 (2)	0.41047 (7)	0.0562 (5)
O1	0.3755 (4)	0.42664 (18)	0.27655 (6)	0.0620 (5)
O2	0.1319 (4)	0.29948 (17)	0.35597 (6)	0.0539 (4)
C1	0.4849 (6)	0.7258 (2)	0.35967 (9)	0.0547 (6)
H1	0.5707	0.7596	0.3222	0.066*
C2	0.3408 (5)	0.5700 (2)	0.37131 (8)	0.0407 (5)
C3	0.2884 (5)	0.4274 (2)	0.32930 (8)	0.0435 (5)
C4	0.0524 (6)	0.1556 (3)	0.31750 (10)	0.0634 (6)
H4A	−0.0937	0.1895	0.2834	0.095*
H4B	−0.0597	0.0720	0.3414	0.095*
H4C	0.2579	0.1095	0.3022	0.095*
C5	0.2690 (6)	0.7700 (3)	0.51385 (9)	0.0567 (6)
H5A	0.1463	0.6831	0.5342	0.085*
H5B	0.1374	0.8715	0.5130	0.085*
H5C	0.4805	0.7896	0.5359	0.085*

	U11	U22	U33	U12	U13	U23
N1	0.0534 (11)	0.0371 (9)	0.0423 (9)	−0.0034 (7)	0.0041 (7)	0.0000 (7)
N2	0.0581 (11)	0.0348 (9)	0.0419 (9)	−0.0033 (7)	0.0029 (7)	−0.0004 (7)
N3	0.0755 (13)	0.0424 (10)	0.0511 (10)	−0.0100 (9)	0.0069 (9)	0.0050 (8)
O1	0.0904 (12)	0.0553 (9)	0.0413 (8)	0.0058 (8)	0.0164 (7)	0.0007 (6)
O2	0.0715 (10)	0.0457 (8)	0.0450 (8)	−0.0120 (7)	0.0066 (6)	−0.0058 (6)
C1	0.0740 (15)	0.0480 (12)	0.0427 (11)	−0.0060 (10)	0.0109 (10)	0.0065 (9)
C2	0.0454 (11)	0.0381 (10)	0.0388 (10)	0.0017 (8)	0.0034 (8)	0.0050 (8)
C3	0.0502 (12)	0.0422 (11)	0.0382 (10)	0.0072 (9)	0.0018 (8)	0.0038 (8)
C4	0.0752 (16)	0.0449 (12)	0.0699 (15)	−0.0064 (11)	0.0016 (12)	−0.0155 (10)
C5	0.0770 (16)	0.0479 (13)	0.0455 (11)	−0.0022 (10)	0.0067 (10)	−0.0084 (9)

N1—N2	1.315 (2)	C1—H1	0.9300
N1—C2	1.340 (2)	C2—C3	1.464 (3)
N2—N3	1.333 (2)	C4—H4A	0.9600
N2—C5	1.456 (2)	C4—H4B	0.9600
N3—C1	1.325 (2)	C4—H4C	0.9600
O1—C3	1.205 (2)	C5—H5A	0.9600
O2—C3	1.333 (2)	C5—H5B	0.9600
O2—C4	1.444 (2)	C5—H5C	0.9600
C1—C2	1.391 (3)
N2—N1—C2	103.75 (15)	O2—C3—C2	112.31 (16)
N1—N2—N3	115.69 (15)	O2—C4—H4A	109.5
N1—N2—C5	121.67 (15)	O2—C4—H4B	109.5
N3—N2—C5	122.63 (16)	H4A—C4—H4B	109.5
C1—N3—N2	103.33 (16)	O2—C4—H4C	109.5
C3—O2—C4	116.74 (16)	H4A—C4—H4C	109.5
N3—C1—C2	109.13 (17)	H4B—C4—H4C	109.5
N3—C1—H1	125.4	N2—C5—H5A	109.5
C2—C1—H1	125.4	N2—C5—H5B	109.5
N1—C2—C1	108.10 (16)	H5A—C5—H5B	109.5
N1—C2—C3	123.02 (17)	N2—C5—H5C	109.5
C1—C2—C3	128.88 (17)	H5A—C5—H5C	109.5
O1—C3—O2	124.03 (17)	H5B—C5—H5C	109.5
O1—C3—C2	123.65 (18)
C2—N1—N2—N3	0.1 (2)	N3—C1—C2—C3	179.47 (18)
C2—N1—N2—C5	179.01 (17)	C4—O2—C3—O1	−2.7 (3)
N1—N2—N3—C1	0.2 (2)	C4—O2—C3—C2	176.96 (16)
C5—N2—N3—C1	−178.75 (18)	N1—C2—C3—O1	−179.38 (18)
N2—N3—C1—C2	−0.3 (2)	C1—C2—C3—O1	1.7 (3)
N2—N1—C2—C1	−0.3 (2)	N1—C2—C3—O2	1.0 (3)
N2—N1—C2—C3	−179.42 (17)	C1—C2—C3—O2	−177.96 (19)
N3—C1—C2—N1	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.53	3.416 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.53	3.416 (3)	159

Symmetry code: (i) .