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

Li, X.-X.; Chen, Z.

doi:10.1107/S160053681005138X

organic compounds

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Volume 67| Part 1| January 2011| Page o140

https://doi.org/10.1107/S160053681005138X

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

Xiao-Xia Li ^a ^* and Zhong Chen ^a

^aInstitute of Functional Materials, Jiangxi University of Finance & Economics, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: xiaoxialichen@yahoo.cn

(Received 17 November 2010; accepted 7 December 2010; online 15 December 2010)

The title compound, C₁₀H₁₁N₃O₂, was synthesized by the reaction of 1H-benzotriazole with ethyl 2-chloroacetate 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 intermolecular C—H⋯N and C—H⋯O interactions 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_r = 205.22
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.231
S = 1.07
2551 reflections
137 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681005138X/vm2062Isup2.hkl

checkCIF report

Comment top

The Schiff-bases derived from benzotriazol-1-yl-acetic acid hydrazide with a relevant aldehyde or ketone have been widely investigated in recent years (Shi et al., 2007a; Shi et al., 2007b; Ji et al., 2008). As an important intermediate in the synthesis procedure of benzotriazol-1-yl-acetic acid hydrazide (Zhang et al., 2009), the title compound, (I), was synthesized and characterized by X-ray diffraction. The asymmetric unit of (I) comprises one independent molecule (Fig. 1). All the bond lengths are comparable with those observed in benzotriazol-1-yl-acetic acid hydrazide. In the crystal, weak intermolecular C—H···N and C—H···O interactions are helpful to consolidate the three-dimensional network (Fig. 2, Table 1).

Related literature top

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

Experimental top

1H-benzotriazole (1 mmol) and sodium hydroxide (1 mmol) were dissolved in ethanol (10 ml), and an ethanol (5 ml) solution of ethyl 2-chloroacetate (1 mmol) was added dropwise. After stirring for 4 h at room temperature, the mixture was filtered and set aside to crystallize at room temperature for several days, giving colourless block crystals.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with the displacement ellipsoids shown at the 30% probability level.
	Fig. 2. The crystal packing for the title compound via C—H···O and C—H···N weak interactions shown as dashed lines.

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

Crystal data top

C₁₀H₁₁N₃O₂	F(000) = 864
M_r = 205.22	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1115P)² + 0.7271P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2551 reflections	Δρ_max = 0.50 e Å⁻³
137 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₁₁N₃O₂	V = 2139.44 (16) Å³
M_r = 205.22	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.6734 (9) Å	µ = 0.09 mm⁻¹
b = 11.9284 (5) Å	T = 296 K
c = 9.3420 (4) Å	0.23 × 0.18 × 0.16 mm
β = 111.770 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2551 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1360 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.039
9605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.231	H-atom parameters constrained
S = 1.07	Δρ_max = 0.50 e Å⁻³
2551 reflections	Δρ_min = −0.24 e Å⁻³
137 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	0.22410 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₃O₂
M_r	205.22
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	20.6734 (9), 11.9284 (5), 9.3420 (4)
β (°)	111.770 (3)
V (Å³)	2139.44 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	9605, 2551, 1360
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.231, 1.07
No. of reflections	2551
No. of parameters	137
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) x, −y, z+1/2.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA . Google Scholar
Ji, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o655. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007a). Acta Cryst. E63, o4561. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007b). Acta Cryst. E63, o4642. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, Y.-X. & Shi, Z.-Q. (2009). Acta Cryst. E65, o1538. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o140

https://doi.org/10.1107/S160053681005138X

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