Ethyl 2-(1H-1,2,3-benzotriazol-1-yl)acetate.

The title compound, C(10)H(11)N(3)O(2), was synthesized by the reaction of 1H-benzotriazole with ethyl 2-chloro-acetate in ethanol. The non-H atoms, excluding the benzotriazol-1-yl group, are almost coplanar (r.m.s. deviation of the non-H atoms = 0.0409 Å). The dihedral angle formed between this plane and the benzotriazole ring is 79.12 (5)° In the crystal, weak inter-molecular C-H⋯N and C-H⋯O inter-actions help to consolidate the three-dimensional network.

Related literature

For related structures, see: Shi et al. (2007a ▶,b ▶); Ji et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C10H11N3O2

M = 205.22

Monoclinic,

a = 20.6734 (9) Å

b = 11.9284 (5) Å

c = 9.3420 (4) Å

β = 111.770 (3)°

V = 2139.44 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.23 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.980, T max = 0.985

9605 measured reflections

2551 independent reflections

1360 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.231

S = 1.07

2551 reflections

137 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005138X/vm2062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005138X/vm2062Isup2.hkl

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

C10H11N3O2	F(000) = 864
Mr = 205.22	Dx = 1.274 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1764 reflections
a = 20.6734 (9) Å	θ = 2.8–21.8°
b = 11.9284 (5) Å	µ = 0.09 mm−1
c = 9.3420 (4) Å	T = 296 K
β = 111.770 (3)°	Block, colourless
V = 2139.44 (16) Å3	0.23 × 0.18 × 0.16 mm
Z = 8

Bruker SMART APEX CCD diffractometer	2551 independent reflections
Radiation source: fine-focus sealed tube	1360 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −24→27
Tmin = 0.980, Tmax = 0.985	k = −15→13
9605 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.231	w = 1/[σ2(Fo2) + (0.1115P)2 + 0.7271P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2551 reflections	Δρmax = 0.50 e Å−3
137 parameters	Δρmin = −0.24 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0044 (15)

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	0.22410 (13)	−0.01039 (19)	0.6218 (3)	0.0558 (6)
C2	0.19757 (14)	−0.1116 (2)	0.5489 (3)	0.0682 (7)
H2A	0.2148	−0.1805	0.5934	0.082*
C3	0.14480 (17)	−0.1032 (3)	0.4084 (3)	0.0850 (9)
H3A	0.1254	−0.1685	0.3554	0.102*
C4	0.11878 (19)	0.0009 (3)	0.3412 (4)	0.0953 (11)
H4A	0.0829	0.0026	0.2448	0.114*
C5	0.14479 (17)	0.0994 (3)	0.4138 (3)	0.0847 (9)
H5A	0.1273	0.1683	0.3695	0.102*
C6	0.19825 (14)	0.0923 (2)	0.5557 (3)	0.0646 (7)
C7	0.31980 (13)	−0.0550 (2)	0.8782 (3)	0.0599 (7)
H7A	0.2938	−0.1200	0.8893	0.072*
H7B	0.3356	−0.0143	0.9751	0.072*
C8	0.38177 (14)	−0.0931 (2)	0.8442 (3)	0.0656 (7)
C9	0.4915 (2)	−0.1815 (5)	0.9535 (4)	0.1336 (18)
H9A	0.4811	−0.2436	0.8814	0.160*
H9B	0.5121	−0.1219	0.9141	0.160*
C10	0.5370 (3)	−0.2152 (7)	1.0919 (6)	0.193 (3)
H10A	0.5790	−0.2408	1.0814	0.289*
H10B	0.5168	−0.2753	1.1299	0.289*
H10C	0.5474	−0.1536	1.1630	0.289*
N1	0.27471 (10)	0.01616 (16)	0.7579 (2)	0.0587 (6)
N2	0.28073 (12)	0.12909 (18)	0.7742 (3)	0.0746 (7)
N3	0.23544 (14)	0.17555 (18)	0.6542 (3)	0.0791 (7)
O1	0.39013 (12)	−0.0827 (2)	0.7269 (2)	0.1030 (8)
O2	0.42674 (10)	−0.1412 (2)	0.9665 (2)	0.0926 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0550 (14)	0.0542 (14)	0.0614 (14)	0.0012 (11)	0.0252 (11)	0.0022 (11)
C2	0.0740 (18)	0.0594 (15)	0.0700 (16)	−0.0027 (13)	0.0252 (14)	−0.0003 (12)
C3	0.086 (2)	0.088 (2)	0.0721 (18)	−0.0117 (17)	0.0185 (16)	−0.0098 (16)
C4	0.079 (2)	0.122 (3)	0.0710 (19)	0.005 (2)	0.0117 (16)	0.0104 (19)
C5	0.086 (2)	0.085 (2)	0.0772 (19)	0.0188 (17)	0.0246 (17)	0.0170 (16)
C6	0.0655 (16)	0.0586 (15)	0.0730 (16)	0.0084 (12)	0.0295 (14)	0.0083 (12)
C7	0.0588 (15)	0.0603 (15)	0.0571 (13)	0.0023 (11)	0.0173 (11)	0.0007 (11)
C8	0.0630 (16)	0.0714 (17)	0.0584 (15)	0.0066 (13)	0.0179 (12)	0.0009 (12)
C9	0.088 (3)	0.212 (5)	0.099 (3)	0.066 (3)	0.032 (2)	0.013 (3)
C10	0.095 (3)	0.328 (8)	0.153 (4)	0.078 (4)	0.043 (3)	0.042 (5)
N1	0.0619 (13)	0.0470 (11)	0.0653 (12)	0.0005 (9)	0.0214 (10)	−0.0025 (9)
N2	0.0837 (16)	0.0490 (12)	0.0866 (16)	0.0008 (11)	0.0264 (13)	−0.0048 (11)
N3	0.0919 (18)	0.0531 (13)	0.0878 (16)	0.0087 (12)	0.0282 (14)	0.0035 (12)
O1	0.0971 (17)	0.151 (2)	0.0722 (13)	0.0321 (14)	0.0445 (12)	0.0153 (13)
O2	0.0721 (13)	0.1303 (19)	0.0729 (12)	0.0370 (13)	0.0240 (10)	0.0187 (12)

C1—N1	1.351 (3)	C7—H7A	0.9700
C1—C6	1.387 (3)	C7—H7B	0.9700
C1—C2	1.395 (3)	C8—O1	1.177 (3)
C2—C3	1.364 (4)	C8—O2	1.309 (3)
C2—H2A	0.9300	C9—C10	1.348 (5)
C3—C4	1.405 (5)	C9—O2	1.468 (4)
C3—H3A	0.9300	C9—H9A	0.9700
C4—C5	1.364 (5)	C9—H9B	0.9700
C4—H4A	0.9300	C10—H10A	0.9600
C5—C6	1.378 (4)	C10—H10B	0.9600
C5—H5A	0.9300	C10—H10C	0.9600
C6—N3	1.378 (3)	N1—N2	1.356 (3)
C7—N1	1.441 (3)	N2—N3	1.289 (3)
C7—C8	1.501 (4)
N1—C1—C6	104.3 (2)	H7A—C7—H7B	107.9
N1—C1—C2	133.6 (2)	O1—C8—O2	123.9 (3)
C6—C1—C2	122.1 (2)	O1—C8—C7	126.7 (3)
C3—C2—C1	115.8 (3)	O2—C8—C7	109.5 (2)
C3—C2—H2A	122.1	C10—C9—O2	110.6 (3)
C1—C2—H2A	122.1	C10—C9—H9A	109.5
C2—C3—C4	122.1 (3)	O2—C9—H9A	109.5
C2—C3—H3A	118.9	C10—C9—H9B	109.5
C4—C3—H3A	118.9	O2—C9—H9B	109.5
C5—C4—C3	121.6 (3)	H9A—C9—H9B	108.1
C5—C4—H4A	119.2	C9—C10—H10A	109.5
C3—C4—H4A	119.2	C9—C10—H10B	109.5
C4—C5—C6	116.9 (3)	H10A—C10—H10B	109.5
C4—C5—H5A	121.5	C9—C10—H10C	109.5
C6—C5—H5A	121.5	H10A—C10—H10C	109.5
N3—C6—C5	130.4 (3)	H10B—C10—H10C	109.5
N3—C6—C1	108.2 (2)	C1—N1—N2	110.22 (19)
C5—C6—C1	121.4 (3)	C1—N1—C7	130.4 (2)
N1—C7—C8	111.7 (2)	N2—N1—C7	119.4 (2)
N1—C7—H7A	109.3	N3—N2—N1	108.8 (2)
C8—C7—H7A	109.3	N2—N3—C6	108.5 (2)
N1—C7—H7B	109.3	C8—O2—C9	116.4 (2)
C8—C7—H7B	109.3
N1—C1—C2—C3	179.7 (3)	C2—C1—N1—N2	179.5 (3)
C6—C1—C2—C3	0.3 (4)	C6—C1—N1—C7	179.3 (2)
C1—C2—C3—C4	0.0 (5)	C2—C1—N1—C7	−0.2 (5)
C2—C3—C4—C5	−0.4 (5)	C8—C7—N1—C1	83.0 (3)
C3—C4—C5—C6	0.5 (5)	C8—C7—N1—N2	−96.6 (3)
C4—C5—C6—N3	178.7 (3)	C1—N1—N2—N3	0.6 (3)
C4—C5—C6—C1	−0.3 (4)	C7—N1—N2—N3	−179.7 (2)
N1—C1—C6—N3	1.1 (3)	N1—N2—N3—C6	0.1 (3)
C2—C1—C6—N3	−179.3 (2)	C5—C6—N3—N2	−179.9 (3)
N1—C1—C6—C5	−179.7 (2)	C1—C6—N3—N2	−0.8 (3)
C2—C1—C6—C5	−0.1 (4)	O1—C8—O2—C9	1.3 (5)
N1—C7—C8—O1	−10.6 (4)	C7—C8—O2—C9	−178.8 (3)
N1—C7—C8—O2	169.5 (2)	C10—C9—O2—C8	171.7 (5)
C6—C1—N1—N2	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N2i	0.93	2.57	3.457 (3)	159
C7—H7A···N3i	0.97	2.51	3.387 (3)	150
C7—H7B···O1ii	0.97	2.49	3.451 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯N2i	0.93	2.57	3.457 (3)	159
C7—H7A⋯N3i	0.97	2.51	3.387 (3)	150
C7—H7B⋯O1ii	0.97	2.49	3.451 (3)	173

Symmetry codes: (i) ; (ii) .