Ethyl 1-(6-chloro-3-pyridylmeth-yl)-5-ethoxy-methyl-eneamino-1H-1,2,3-triazole-4-carboxyl-ate.

In the title compound, C(14)H(16)ClN(5)O(3), there is evidence for significant electron delocalization in the triazolyl system. Intra-molecular C-H⋯O and inter-molecular 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 = 337.77

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.04

2980 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.40 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037197/at2675sup1.cif

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

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

C14H16ClN5O3	F000 = 704
Mr = 337.77	Dx = 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 = 2.7–27.8º
b = 6.3134 (6) Å	µ = 0.26 mm−1
c = 15.3065 (15) Å	T = 291 (2) K
β = 90.9800 (10)º	Block, colourless
V = 1631.2 (3) Å3	0.50 × 0.47 × 0.36 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2551 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Monochromator: graphite	θmax = 25.5º
T = 291(2) K	θmin = 2.7º
φ and ω scans	h = −20→20
Absorption correction: none	k = −7→7
10092 measured reflections	l = −18→18
2980 independent reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.5005P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2980 reflections	Δρmax = 0.25 e Å−3
210 parameters	Δρmin = −0.40 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
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*

	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)

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)

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

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) ; (ii) .