Ethyl 1-(6-chloro-3-pyridylmeth­yl)-5-ethoxy­methyl­eneamino-1H-1,2,3-triazole-4-carboxyl­ate

Chen, X.-B.; Sun, F.-M.; Gao, H.-T.; Xu, J.; Zheng, A.-H.

doi:10.1107/S1600536808037197

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2352

doi:10.1107/S1600536808037197

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Ethyl 1-(6-chloro-3-pyridylmethyl)-5-ethoxymethyleneamino-1H-1,2,3-triazole-4-carboxylate

Xiao-Bao Chen,^a Feng-Mei Sun,^b Hai-Tao Gao,^a ^* Jing Xu ^a and Ai-Hua Zheng ^a

^aDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453003, Henan, People's Republic of China
^*Correspondence e-mail: chenxiaobao@yahoo.com.cn

(Received 9 November 2008; accepted 10 November 2008; online 13 November 2008)

In the title compound, C₁₄H₁₆ClN₅O₃, there is evidence for significant electron delocalization in the triazolyl system. Intramolecular C—H⋯O and intermolecular C—H⋯O and C—H⋯N hydrogen bonds stabilize the structure.

Related literature

Many derivatives of triazole have been prepared, and their biological activities have been studied, see: Ogura et al. (2000a ,b ); Najim et al. (2004 ); Banks & Chubb (1999a ,b ); Shuto et al. (1995a ,b ); Yuan et al. (2006 ); Chen et al. (2005 ); Liu et al. (2001 ). For the synthesis, see: Chen & Shi (2008 ). For bond-length data, see: Sasada (1984 ); Wang et al. (1998 ).

Experimental

Crystal data

C₁₄H₁₆ClN₅O₃
M_r = 337.77
Monoclinic, P 2₁ /c
a = 16.8823 (17) Å
b = 6.3134 (6) Å
c = 15.3065 (15) Å
β = 90.980 (1)°
V = 1631.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 291 (2) K
0.50 × 0.47 × 0.36 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
10092 measured reflections
2980 independent reflections
2551 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.04
2980 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N3ⁱ	0.93	2.57	3.488 (2)	167
C9—H9A⋯O2ⁱⁱ	0.97	2.53	3.246 (3)	131
C12—H12⋯O2	0.93	2.44	2.924 (3)	112
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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 global, I. DOI: 10.1107/S1600536808037197/at2675sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037197/at2675Isup2.hkl

checkCIF report

Comment top

It is well known that many triazole-related molecules play an important role in the development of agrochemicals such as insecticides, nematocides, acaricide and plant growth regulators (Ogura et al., 2000a,b; Najim et al., 2004; Banks & Chubb, 1999a,b); Shuto et al., 1995a,b; Yuan et al., 2006; Chen et al., 2005 and Liu et al., 2001). Since the structure-activity relationship is very useful in the rational design of pharmaceuticals and agrochemicals. We report here the crystal structure of the title compound, (I) (Fig. 1), which was synthesized by introducing pyridine rings into a 1,2,3-triazole molecular framework.

In the title compound (I), the C7—N4 and C11—N2 bonds [1.366 (2) and 1.348 (2) Å] are significantly shorter than that of the single bond of C—N (1.47 Å; Sasada, 1984) and close to the value of the double bond of C—N (1.28 Å; Wang et al., 1998). This indicates significant electron delocalization in the triazolyl system. Intramolecular C—H···O and intermolecular C—H···O and C—H···N hydrogen bonds contribute strongly to the stability of the molecular configuration (Fig.2, Table 1).

Related literature top

Many derivatives of triazole have been prepared, and their biological activities have been studied, see: Ogura et al. (2000a,b); Najim et al. (2004); Banks & Chubb (1999a,b); Shuto et al. (1995a,b); Yuan et al. (2006); Chen et al. (2005); Liu et al. (2001). For the synthesis, see: Chen & Shi (2008). For bond-length data, see: Sasada (1984); Wang et al. (1998).

Experimental top

A solution of compound 1-((6-chloropyridin-3-yl)methyl)-4-ethoxycarbonyl-5-amine-1H-1,2,3- triazole (2 mmol) in triethyl ortho formate (10 ml) was refluxed for 4 h, cooled briefly and evaporated. The residue was purified by chromatography on a silica gel column by eluting with petroleum ether/acetone (2:1, v/v) to give the title compound (yield 75%). Colourless crystals of (I) suitable for X-ray structure analysis were grown from acetone and petroleum ether (1:3, v/v).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. View of the molecular structure of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of (I), showing the formation of C—H···O and C—H···N hydrogen-bonding interactions (dashed lines).

Ethyl 1-(6-chloro-3-pyridylmethyl)-5-ethoxymethyleneamino-1H- 1,2,3-triazole-4-carboxylate top

Crystal data top

C₁₄H₁₆ClN₅O₃	F(000) = 704
M_r = 337.77	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4752 reflections
a = 16.8823 (17) Å	θ = 2.7–27.8°
b = 6.3134 (6) Å	µ = 0.26 mm⁻¹
c = 15.3065 (15) Å	T = 291 K
β = 90.980 (1)°	Block, colourless
V = 1631.2 (3) Å³	0.50 × 0.47 × 0.36 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2551 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 25.5°, θ_min = 2.7°
ϕ and ω scans	h = −20→20
10092 measured reflections	k = −7→7
2980 independent reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0449P)² + 0.5005P] where P = (F_o² + 2F_c²)/3
2980 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₄H₁₆ClN₅O₃	V = 1631.2 (3) Å³
M_r = 337.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8823 (17) Å	µ = 0.26 mm⁻¹
b = 6.3134 (6) Å	T = 291 K
c = 15.3065 (15) Å	0.50 × 0.47 × 0.36 mm
β = 90.980 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2551 reflections with I > 2σ(I)
10092 measured reflections	R_int = 0.014
2980 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
2980 reflections	Δρ_min = −0.40 e Å⁻³
210 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
Cl1	0.36873 (3)	0.34616 (9)	0.06142 (3)	0.07336 (19)
O1	0.89923 (7)	0.8586 (2)	−0.04595 (8)	0.0571 (3)
O2	0.91635 (9)	0.6353 (3)	0.06636 (11)	0.0821 (5)
O3	0.80412 (9)	0.27638 (19)	0.22225 (8)	0.0633 (4)
N1	0.50169 (9)	0.4258 (2)	0.14254 (10)	0.0559 (4)
N2	0.69532 (8)	0.9067 (2)	0.13235 (8)	0.0440 (3)
N3	0.69871 (8)	1.0541 (2)	0.06795 (9)	0.0499 (3)
N4	0.76295 (8)	1.0162 (2)	0.02373 (9)	0.0494 (3)
N5	0.76407 (8)	0.6142 (2)	0.19200 (8)	0.0470 (3)
C1	0.44375 (10)	0.5167 (3)	0.09780 (10)	0.0480 (4)
C2	0.43841 (11)	0.7289 (3)	0.07976 (12)	0.0582 (5)
H2	0.3959	0.7842	0.0477	0.070*
C3	0.49856 (10)	0.8571 (3)	0.11104 (12)	0.0545 (4)
H3	0.4972	1.0021	0.1004	0.065*
C4	0.56076 (9)	0.7699 (3)	0.15809 (10)	0.0422 (4)
C5	0.55899 (10)	0.5546 (3)	0.17194 (12)	0.0535 (4)
H5	0.6006	0.4946	0.2040	0.064*
C6	0.62874 (10)	0.9037 (3)	0.19223 (11)	0.0504 (4)
H6A	0.6103	1.0475	0.2012	0.061*
H6B	0.6466	0.8485	0.2483	0.061*
C7	0.80079 (9)	0.8443 (2)	0.05900 (10)	0.0443 (4)
C8	0.87732 (10)	0.7667 (3)	0.02805 (12)	0.0515 (4)
C9	0.97474 (11)	0.7873 (3)	−0.08109 (14)	0.0676 (5)
H9A	0.9744	0.6348	−0.0885	0.081*
H9B	1.0179	0.8246	−0.0414	0.081*
C10	0.98505 (15)	0.8939 (5)	−0.16692 (17)	0.0994 (9)
H10A	0.9433	0.8509	−0.2065	0.149*
H10B	1.0353	0.8547	−0.1905	0.149*
H10C	0.9832	1.0446	−0.1591	0.149*
C11	0.75714 (9)	0.7719 (2)	0.12926 (10)	0.0424 (4)
C12	0.79167 (12)	0.4373 (3)	0.16850 (11)	0.0580 (5)
H12	0.8039	0.4194	0.1100	0.070*
C13	0.78506 (12)	0.3050 (3)	0.31347 (11)	0.0584 (5)
H13A	0.7281	0.3109	0.3205	0.070*
H13B	0.8080	0.4356	0.3357	0.070*
C14	0.81906 (16)	0.1190 (4)	0.36122 (14)	0.0812 (7)
H14A	0.7993	−0.0094	0.3353	0.122*
H14B	0.8040	0.1248	0.4214	0.122*
H14C	0.8758	0.1219	0.3578	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0601 (3)	0.0926 (4)	0.0674 (3)	−0.0200 (3)	0.0024 (2)	−0.0204 (3)
O1	0.0478 (7)	0.0593 (7)	0.0647 (7)	0.0024 (5)	0.0108 (6)	0.0029 (6)
O2	0.0658 (9)	0.0824 (10)	0.0985 (11)	0.0239 (8)	0.0096 (8)	0.0267 (9)
O3	0.0954 (10)	0.0428 (7)	0.0519 (7)	0.0049 (6)	0.0048 (7)	0.0053 (5)
N1	0.0510 (8)	0.0480 (8)	0.0687 (9)	−0.0032 (7)	−0.0003 (7)	0.0059 (7)
N2	0.0445 (7)	0.0411 (7)	0.0464 (7)	−0.0041 (6)	−0.0016 (6)	0.0019 (6)
N3	0.0495 (8)	0.0455 (8)	0.0546 (8)	−0.0002 (6)	−0.0009 (6)	0.0080 (6)
N4	0.0477 (8)	0.0475 (8)	0.0529 (8)	−0.0023 (6)	−0.0001 (6)	0.0067 (6)
N5	0.0504 (8)	0.0442 (8)	0.0461 (7)	−0.0011 (6)	−0.0046 (6)	0.0045 (6)
C1	0.0440 (9)	0.0595 (10)	0.0409 (8)	−0.0040 (7)	0.0085 (7)	−0.0054 (7)
C2	0.0475 (10)	0.0673 (12)	0.0596 (10)	0.0089 (8)	−0.0050 (8)	0.0090 (9)
C3	0.0537 (10)	0.0448 (9)	0.0652 (11)	0.0078 (8)	0.0022 (8)	0.0091 (8)
C4	0.0437 (8)	0.0440 (8)	0.0391 (8)	0.0033 (7)	0.0078 (6)	0.0001 (7)
C5	0.0482 (9)	0.0501 (10)	0.0620 (10)	0.0016 (8)	−0.0058 (8)	0.0132 (8)
C6	0.0540 (10)	0.0485 (9)	0.0490 (9)	−0.0009 (8)	0.0061 (7)	−0.0045 (7)
C7	0.0437 (9)	0.0413 (8)	0.0476 (9)	−0.0043 (7)	−0.0045 (7)	0.0016 (7)
C8	0.0461 (9)	0.0477 (9)	0.0607 (10)	−0.0032 (7)	−0.0022 (8)	0.0003 (8)
C9	0.0483 (10)	0.0690 (12)	0.0859 (14)	0.0012 (9)	0.0135 (10)	−0.0138 (11)
C10	0.0811 (16)	0.127 (2)	0.0917 (17)	0.0149 (16)	0.0392 (14)	0.0044 (16)
C11	0.0437 (8)	0.0391 (8)	0.0441 (8)	−0.0044 (7)	−0.0070 (7)	−0.0013 (7)
C12	0.0857 (13)	0.0450 (10)	0.0434 (9)	−0.0065 (9)	0.0000 (9)	0.0018 (8)
C13	0.0672 (12)	0.0585 (11)	0.0494 (9)	0.0055 (9)	0.0033 (8)	0.0074 (8)
C14	0.1104 (18)	0.0668 (13)	0.0665 (13)	0.0154 (12)	0.0013 (12)	0.0190 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.7462 (17)	C4—C5	1.376 (2)
O1—C8	1.331 (2)	C4—C6	1.511 (2)
O1—C9	1.463 (2)	C5—H5	0.9300
O2—C8	1.205 (2)	C6—H6A	0.9700
O3—C12	1.322 (2)	C6—H6B	0.9700
O3—C13	1.450 (2)	C7—C11	1.391 (2)
N1—C1	1.316 (2)	C7—C8	1.468 (2)
N1—C5	1.336 (2)	C9—C10	1.489 (3)
N2—C11	1.348 (2)	C9—H9A	0.9700
N2—N3	1.3579 (18)	C9—H9B	0.9700
N2—C6	1.463 (2)	C10—H10A	0.9600
N3—N4	1.3103 (19)	C10—H10B	0.9600
N4—C7	1.366 (2)	C10—H10C	0.9600
N5—C12	1.264 (2)	C12—H12	0.9300
N5—C11	1.387 (2)	C13—C14	1.493 (3)
C1—C2	1.371 (3)	C13—H13A	0.9700
C2—C3	1.378 (3)	C13—H13B	0.9700
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.378 (2)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600

C8—O1—C9	115.82 (15)	O2—C8—O1	123.82 (16)
C12—O3—C13	117.92 (14)	O2—C8—C7	123.34 (17)
C1—N1—C5	115.93 (15)	O1—C8—C7	112.83 (15)
C11—N2—N3	111.41 (13)	O1—C9—C10	107.54 (18)
C11—N2—C6	128.15 (13)	O1—C9—H9A	110.2
N3—N2—C6	120.40 (13)	C10—C9—H9A	110.2
N4—N3—N2	107.16 (13)	O1—C9—H9B	110.2
N3—N4—C7	109.08 (13)	C10—C9—H9B	110.2
C12—N5—C11	117.65 (14)	H9A—C9—H9B	108.5
N1—C1—C2	125.22 (16)	C9—C10—H10A	109.5
N1—C1—Cl1	115.20 (13)	C9—C10—H10B	109.5
C2—C1—Cl1	119.57 (14)	H10A—C10—H10B	109.5
C1—C2—C3	117.28 (16)	C9—C10—H10C	109.5
C1—C2—H2	121.4	H10A—C10—H10C	109.5
C3—C2—H2	121.4	H10B—C10—H10C	109.5
C4—C3—C2	119.84 (16)	N2—C11—N5	119.02 (14)
C4—C3—H3	120.1	N2—C11—C7	103.90 (13)
C2—C3—H3	120.1	N5—C11—C7	137.02 (15)
C5—C4—C3	117.18 (16)	N5—C12—O3	123.85 (16)
C5—C4—C6	121.16 (15)	N5—C12—H12	118.1
C3—C4—C6	121.65 (15)	O3—C12—H12	118.1
N1—C5—C4	124.54 (16)	O3—C13—C14	106.49 (16)
N1—C5—H5	117.7	O3—C13—H13A	110.4
C4—C5—H5	117.7	C14—C13—H13A	110.4
N2—C6—C4	112.19 (13)	O3—C13—H13B	110.4
N2—C6—H6A	109.2	C14—C13—H13B	110.4
C4—C6—H6A	109.2	H13A—C13—H13B	108.6
N2—C6—H6B	109.2	C13—C14—H14A	109.5
C4—C6—H6B	109.2	C13—C14—H14B	109.5
H6A—C6—H6B	107.9	H14A—C14—H14B	109.5
N4—C7—C11	108.44 (14)	C13—C14—H14C	109.5
N4—C7—C8	123.09 (14)	H14A—C14—H14C	109.5
C11—C7—C8	128.35 (15)	H14B—C14—H14C	109.5

C11—N2—N3—N4	−0.55 (17)	C9—O1—C8—C7	−179.47 (14)
C6—N2—N3—N4	−178.53 (13)	N4—C7—C8—O2	169.02 (17)
N2—N3—N4—C7	0.30 (17)	C11—C7—C8—O2	−6.6 (3)
C5—N1—C1—C2	0.0 (3)	N4—C7—C8—O1	−10.2 (2)
C5—N1—C1—Cl1	−179.06 (13)	C11—C7—C8—O1	174.16 (15)
N1—C1—C2—C3	0.0 (3)	C8—O1—C9—C10	175.16 (19)
Cl1—C1—C2—C3	179.07 (13)	N3—N2—C11—N5	178.28 (13)
C1—C2—C3—C4	0.2 (3)	C6—N2—C11—N5	−3.9 (2)
C2—C3—C4—C5	−0.4 (2)	N3—N2—C11—C7	0.55 (17)
C2—C3—C4—C6	178.87 (15)	C6—N2—C11—C7	178.34 (14)
C1—N1—C5—C4	−0.3 (3)	C12—N5—C11—N2	144.61 (16)
C3—C4—C5—N1	0.4 (3)	C12—N5—C11—C7	−38.6 (3)
C6—C4—C5—N1	−178.81 (16)	N4—C7—C11—N2	−0.36 (17)
C11—N2—C6—C4	−88.86 (19)	C8—C7—C11—N2	175.79 (15)
N3—N2—C6—C4	88.75 (17)	N4—C7—C11—N5	−177.45 (17)
C5—C4—C6—N2	85.12 (19)	C8—C7—C11—N5	−1.3 (3)
C3—C4—C6—N2	−94.08 (18)	C11—N5—C12—O3	177.40 (16)
N3—N4—C7—C11	0.04 (18)	C13—O3—C12—N5	−0.1 (3)
N3—N4—C7—C8	−176.36 (15)	C12—O3—C13—C14	−169.17 (18)
C9—O1—C8—O2	1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N3ⁱ	0.93	2.57	3.488 (2)	167
C9—H9A···O2ⁱⁱ	0.97	2.53	3.246 (3)	131
C12—H12···O2	0.93	2.44	2.924 (3)	112

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆ClN₅O₃
M_r	337.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	16.8823 (17), 6.3134 (6), 15.3065 (15)
β (°)	90.980 (1)
V (Å³)	1631.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.50 × 0.47 × 0.36

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10092, 2980, 2551
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.04
No. of reflections	2980
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.40

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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—H2···N3ⁱ	0.93	2.57	3.488 (2)	167.00
C9—H9A···O2ⁱⁱ	0.97	2.53	3.246 (3)	131.00
C12—H12···O2	0.93	2.44	2.924 (3)	112.00

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z.

Acknowledgements

The authors gratefully acknowledge financial support of this work by Yunyang Medical College (grant No. 2007ZQB24).

References

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Volume 64| Part 12| December 2008| Page o2352

doi:10.1107/S1600536808037197

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-(6-chloro-3-pyridylmeth­yl)-5-eth­oxy­methyl­ene­amino-1H-1,2,3-triazole-4-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 1-(6-chloro-3-pyridylmethyl)-5-ethoxymethyleneamino-1H-1,2,3-triazole-4-carboxylate