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

The title compound, C(4)H(5)N(3)O(2), features an essentially planar mol-ecule (r.m.s. deviation for all non-H atoms = 0.013 Å). The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds and π-π stacking inter-actions (centroid-centroid distance 3.882 Å).

Related literature

For general background, see: Abu-Orabi et al. (1989 ▶); Fan & Katritzky (1996 ▶); Dehne (1994 ▶). For a related structure, see: Wang et al. (1998 ▶).

Experimental

Crystal data

C4H5N3O2

M = 127.11

Monoclinic,

a = 3.8823 (7) Å

b = 17.499 (3) Å

c = 8.8171 (17) Å

β = 100.938 (3)°

V = 588.12 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 290 (2) K

0.30 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.956, T max = 0.977

4285 measured reflections

1098 independent reflections

917 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.06

1098 reflections

91 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1999 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000877/bt2847sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000877/bt2847Isup2.hkl

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

C4H5N3O2	F(000) = 264
Mr = 127.11	Dx = 1.436 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1804 reflections
a = 3.8823 (7) Å	θ = 2.4–25.5°
b = 17.499 (3) Å	µ = 0.12 mm−1
c = 8.8171 (17) Å	T = 290 K
β = 100.938 (3)°	Block, pale yellow
V = 588.12 (19) Å3	0.30 × 0.23 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1098 independent reflections
Radiation source: fine-focus sealed tube	917 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −4→4
Tmin = 0.956, Tmax = 0.977	k = −21→20
4285 measured reflections	l = −10→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0657P)2 + 0.085P] where P = (Fo2 + 2Fc2)/3
1098 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.12 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
H3N	0.668 (5)	0.1865 (11)	0.529 (2)	0.069 (6)*
H1	0.630 (5)	0.3213 (10)	0.510 (2)	0.067 (5)*
O1	0.2633 (4)	0.39888 (6)	0.89548 (14)	0.0672 (4)
O2	0.4220 (4)	0.44536 (7)	0.68279 (14)	0.0670 (4)
C3	0.3702 (4)	0.38941 (9)	0.77686 (18)	0.0502 (4)
N3	0.5970 (4)	0.21920 (8)	0.59504 (15)	0.0520 (4)
C2	0.4540 (4)	0.31459 (8)	0.71907 (16)	0.0440 (4)
N2	0.5029 (4)	0.19156 (8)	0.72315 (16)	0.0577 (4)
C1	0.5704 (4)	0.29447 (9)	0.58856 (18)	0.0495 (4)
N1	0.4149 (4)	0.25012 (7)	0.79947 (15)	0.0541 (4)
C4	0.3391 (8)	0.52244 (11)	0.7273 (3)	0.0937 (8)
H4A	0.0894	0.5296	0.7056	0.141*
H4B	0.4472	0.5590	0.6700	0.141*
H4C	0.4261	0.5295	0.8358	0.141*

	U11	U22	U33	U12	U13	U23
O1	0.0984 (10)	0.0524 (7)	0.0599 (8)	−0.0045 (6)	0.0379 (7)	−0.0077 (5)
O2	0.0959 (10)	0.0450 (7)	0.0671 (8)	0.0012 (6)	0.0330 (7)	0.0062 (5)
C3	0.0556 (9)	0.0481 (9)	0.0482 (9)	−0.0045 (7)	0.0137 (7)	−0.0012 (7)
N3	0.0643 (9)	0.0499 (8)	0.0443 (8)	0.0026 (6)	0.0167 (6)	−0.0038 (6)
C2	0.0478 (8)	0.0464 (8)	0.0384 (8)	−0.0034 (6)	0.0095 (6)	0.0015 (6)
N2	0.0754 (10)	0.0480 (8)	0.0532 (8)	0.0009 (6)	0.0213 (7)	0.0017 (6)
C1	0.0597 (10)	0.0499 (9)	0.0410 (9)	−0.0013 (7)	0.0152 (7)	0.0031 (7)
N1	0.0702 (9)	0.0480 (8)	0.0478 (8)	−0.0016 (6)	0.0207 (7)	0.0011 (5)
C4	0.134 (2)	0.0464 (11)	0.1117 (18)	0.0019 (11)	0.0499 (16)	0.0029 (11)

O1—C3	1.2075 (19)	C2—N1	1.3561 (19)
O2—C3	1.3231 (19)	C2—C1	1.360 (2)
O2—C4	1.458 (2)	N2—N1	1.3065 (19)
C3—C2	1.464 (2)	C1—H1	0.906 (19)
N3—C1	1.322 (2)	C4—H4A	0.9600
N3—N2	1.3416 (19)	C4—H4B	0.9600
N3—H3N	0.90 (2)	C4—H4C	0.9600
C3—O2—C4	116.63 (15)	N3—C1—C2	104.91 (14)
O1—C3—O2	124.02 (15)	N3—C1—H1	121.4 (12)
O1—C3—C2	124.05 (14)	C2—C1—H1	133.7 (12)
O2—C3—C2	111.92 (13)	N2—N1—C2	108.49 (13)
C1—N3—N2	111.36 (14)	O2—C4—H4A	109.5
C1—N3—H3N	129.6 (12)	O2—C4—H4B	109.5
N2—N3—H3N	119.0 (12)	H4A—C4—H4B	109.5
N1—C2—C1	108.37 (14)	O2—C4—H4C	109.5
N1—C2—C3	120.51 (13)	H4A—C4—H4C	109.5
C1—C2—C3	131.12 (14)	H4B—C4—H4C	109.5
N1—N2—N3	106.88 (13)
C4—O2—C3—O1	−0.7 (3)	N2—N3—C1—C2	0.00 (17)
C4—O2—C3—C2	178.67 (17)	N1—C2—C1—N3	−0.01 (17)
O1—C3—C2—N1	−0.2 (2)	C3—C2—C1—N3	−179.24 (16)
O2—C3—C2—N1	−179.54 (14)	N3—N2—N1—C2	−0.03 (18)
O1—C3—C2—C1	178.95 (17)	C1—C2—N1—N2	0.03 (18)
O2—C3—C2—C1	−0.4 (2)	C3—C2—N1—N2	179.35 (13)
C1—N3—N2—N1	0.02 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1i	0.896 (19)	1.980 (19)	2.8659 (19)	169.56 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1i	0.896 (19)	1.980 (19)	2.8659 (19)	169.56 (18)

Symmetry code: (i) .