Ethyl 6-(4-cyclo-propyl-1H-1,2,3-triazol-1-yl)pyridine-3-carboxyl-ate.

In the title compound, C13H14N4O2, which has approximate mirror symmetry, the dihedral angles between the triazole ring and the cyclo-propane and pyridine rings are 87.1 (2) and 7.60 (9)°, respectively. In the crystal, inversion dimers linked by pairs of both C-H⋯N and C-H⋯O inter-actions generate R 2 (2)(6) and R 2 (2)(18) loops, respectively. Further C-H⋯N inter-actions form R 2 (2)(10) loops and link the dimers into [110] chains.

Related literature

For background to triazoles, see: Kiselyova et al. (2009 ▶). For the synthesis, see: Zhang et al. (2012 ▶).

Experimental

Crystal data

C13H14N4O2

M = 258.28

Triclinic,

a = 7.1565 (6) Å

b = 9.3521 (8) Å

c = 9.8747 (9) Å

α = 85.722 (4)°

β = 81.422 (4)°

γ = 86.941 (4)°

V = 651.09 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.42 × 0.30 × 0.28 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.964, T max = 0.975

8987 measured reflections

2484 independent reflections

1756 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.137

S = 1.04

2484 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.26 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813034673/hb7179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034673/hb7179Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034673/hb7179Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H14N4O2	Z = 2
Mr = 258.28	F(000) = 272
Triclinic, P1	Dx = 1.317 Mg m−3
a = 7.1565 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3521 (8) Å	Cell parameters from 1756 reflections
c = 9.8747 (9) Å	θ = 2.1–26.0°
α = 85.722 (4)°	µ = 0.09 mm−1
β = 81.422 (4)°	T = 296 K
γ = 86.941 (4)°	Prism, colourless
V = 651.09 (10) Å3	0.42 × 0.30 × 0.28 mm

Bruker Kappa APEXII CCD diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	1756 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.964, Tmax = 0.975	l = −12→12
8987 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1169P] where P = (Fo2 + 2Fc2)/3
2484 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.26 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.

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	0.2414 (3)	0.6459 (2)	0.0441 (2)	0.0859 (7)
H1A	0.2315	0.7147	0.1125	0.129*
H1B	0.1520	0.6722	−0.0179	0.129*
H1C	0.3671	0.6441	−0.0061	0.129*
C2	0.2005 (3)	0.5009 (2)	0.1119 (2)	0.0751 (6)
H2A	0.0739	0.5012	0.1633	0.090*
H2B	0.2098	0.4302	0.0439	0.090*
C3	0.3330 (3)	0.33974 (18)	0.27255 (18)	0.0522 (5)
C4	0.4902 (2)	0.31531 (17)	0.35605 (16)	0.0458 (4)
C5	0.5060 (3)	0.18591 (18)	0.43204 (18)	0.0521 (5)
H5	0.4154	0.1186	0.4303	0.062*
C6	0.7698 (2)	0.25016 (17)	0.50747 (16)	0.0434 (4)
C7	0.7690 (3)	0.38274 (18)	0.43583 (19)	0.0556 (5)
H7	0.8617	0.4477	0.4394	0.067*
C8	0.6251 (3)	0.41465 (18)	0.35887 (19)	0.0545 (5)
H8	0.6188	0.5027	0.3090	0.065*
C9	0.9478 (2)	0.08458 (17)	0.66058 (16)	0.0470 (4)
H9	0.8839	0.0002	0.6628	0.056*
C10	1.0960 (2)	0.10746 (18)	0.72627 (17)	0.0480 (4)
C11	1.1936 (3)	0.0111 (2)	0.82036 (18)	0.0589 (5)
H11	1.1577	−0.0892	0.8280	0.071*
C12	1.2412 (3)	0.0654 (3)	0.9484 (2)	0.0734 (6)
H12A	1.2100	0.1655	0.9646	0.088*
H12B	1.2292	0.0006	1.0304	0.088*
C13	1.3932 (3)	0.0332 (3)	0.8366 (2)	0.0763 (6)
H13A	1.4747	−0.0514	0.8498	0.092*
H13B	1.4554	0.1135	0.7840	0.092*
N3	1.0348 (2)	0.30912 (16)	0.61267 (17)	0.0650 (5)
N4	1.1459 (2)	0.24626 (17)	0.69538 (17)	0.0640 (5)
N1	0.6440 (2)	0.15211 (14)	0.50782 (15)	0.0502 (4)
N2	0.9131 (2)	0.21107 (14)	0.59114 (13)	0.0466 (4)
O1	0.34012 (19)	0.46736 (13)	0.20353 (14)	0.0657 (4)
O2	0.2151 (2)	0.25401 (15)	0.26590 (15)	0.0774 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0925 (17)	0.0819 (16)	0.0814 (16)	0.0190 (13)	−0.0276 (13)	0.0204 (12)
C2	0.0823 (15)	0.0681 (13)	0.0825 (15)	0.0107 (11)	−0.0465 (12)	0.0050 (11)
C3	0.0573 (11)	0.0432 (9)	0.0584 (11)	−0.0001 (8)	−0.0188 (9)	0.0008 (8)
C4	0.0487 (10)	0.0421 (9)	0.0483 (10)	−0.0026 (7)	−0.0144 (8)	0.0011 (7)
C5	0.0559 (11)	0.0437 (9)	0.0606 (11)	−0.0134 (8)	−0.0224 (9)	0.0066 (8)
C6	0.0462 (9)	0.0407 (9)	0.0449 (9)	−0.0068 (7)	−0.0137 (7)	0.0048 (7)
C7	0.0581 (11)	0.0443 (9)	0.0680 (12)	−0.0169 (8)	−0.0240 (9)	0.0123 (8)
C8	0.0631 (11)	0.0400 (9)	0.0621 (11)	−0.0085 (8)	−0.0213 (9)	0.0140 (8)
C9	0.0543 (10)	0.0389 (9)	0.0490 (10)	−0.0059 (7)	−0.0149 (8)	0.0059 (7)
C10	0.0457 (10)	0.0507 (10)	0.0493 (10)	−0.0040 (8)	−0.0143 (8)	0.0019 (7)
C11	0.0604 (12)	0.0581 (11)	0.0621 (12)	−0.0009 (9)	−0.0283 (9)	0.0072 (9)
C12	0.0744 (14)	0.0934 (16)	0.0558 (12)	0.0060 (12)	−0.0259 (11)	−0.0001 (11)
C13	0.0583 (13)	0.1031 (17)	0.0695 (14)	0.0069 (11)	−0.0248 (11)	0.0038 (12)
N3	0.0659 (10)	0.0523 (9)	0.0836 (11)	−0.0223 (8)	−0.0369 (9)	0.0176 (8)
N4	0.0615 (10)	0.0589 (10)	0.0776 (11)	−0.0153 (8)	−0.0344 (8)	0.0137 (8)
N1	0.0543 (9)	0.0429 (8)	0.0570 (9)	−0.0127 (6)	−0.0219 (7)	0.0092 (6)
N2	0.0496 (8)	0.0417 (8)	0.0513 (8)	−0.0122 (6)	−0.0183 (6)	0.0073 (6)
O1	0.0711 (9)	0.0536 (8)	0.0781 (9)	−0.0014 (6)	−0.0386 (7)	0.0135 (6)
O2	0.0769 (10)	0.0619 (9)	0.1036 (11)	−0.0156 (8)	−0.0500 (9)	0.0114 (8)

C1—C2	1.490 (3)	C7—H7	0.9300
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—N2	1.353 (2)
C1—H1C	0.9600	C9—C10	1.357 (2)
C2—O1	1.453 (2)	C9—H9	0.9300
C2—H2A	0.9700	C10—N4	1.365 (2)
C2—H2B	0.9700	C10—C11	1.471 (2)
C3—O2	1.206 (2)	C11—C13	1.488 (3)
C3—O1	1.329 (2)	C11—C12	1.489 (3)
C3—C4	1.490 (2)	C11—H11	0.9800
C4—C8	1.380 (2)	C12—C13	1.466 (3)
C4—C5	1.384 (2)	C12—H12A	0.9700
C5—N1	1.337 (2)	C12—H12B	0.9700
C5—H5	0.9300	C13—H13A	0.9700
C6—N1	1.318 (2)	C13—H13B	0.9700
C6—C7	1.381 (2)	N3—N4	1.310 (2)
C6—N2	1.427 (2)	N3—N2	1.347 (2)
C7—C8	1.376 (2)
C2—C1—H1A	109.5	N2—C9—H9	127.5
C2—C1—H1B	109.5	C10—C9—H9	127.5
H1A—C1—H1B	109.5	C9—C10—N4	108.25 (15)
C2—C1—H1C	109.5	C9—C10—C11	130.37 (16)
H1A—C1—H1C	109.5	N4—C10—C11	121.34 (16)
H1B—C1—H1C	109.5	C10—C11—C13	120.71 (18)
O1—C2—C1	106.77 (18)	C10—C11—C12	119.78 (17)
O1—C2—H2A	110.4	C13—C11—C12	58.99 (13)
C1—C2—H2A	110.4	C10—C11—H11	115.3
O1—C2—H2B	110.4	C13—C11—H11	115.3
C1—C2—H2B	110.4	C12—C11—H11	115.3
H2A—C2—H2B	108.6	C13—C12—C11	60.47 (14)
O2—C3—O1	123.76 (17)	C13—C12—H12A	117.7
O2—C3—C4	124.61 (16)	C11—C12—H12A	117.7
O1—C3—C4	111.62 (15)	C13—C12—H12B	117.7
C8—C4—C5	117.89 (16)	C11—C12—H12B	117.7
C8—C4—C3	123.04 (15)	H12A—C12—H12B	114.8
C5—C4—C3	119.04 (15)	C12—C13—C11	60.54 (14)
N1—C5—C4	123.74 (16)	C12—C13—H13A	117.7
N1—C5—H5	118.1	C11—C13—H13A	117.7
C4—C5—H5	118.1	C12—C13—H13B	117.7
N1—C6—C7	125.18 (15)	C11—C13—H13B	117.7
N1—C6—N2	114.66 (14)	H13A—C13—H13B	114.8
C7—C6—N2	120.14 (15)	N4—N3—N2	107.00 (14)
C8—C7—C6	117.21 (16)	N3—N4—C10	109.09 (14)
C8—C7—H7	121.4	C6—N1—C5	116.32 (14)
C6—C7—H7	121.4	N3—N2—C9	110.61 (14)
C7—C8—C4	119.65 (15)	N3—N2—C6	119.87 (13)
C7—C8—H8	120.2	C9—N2—C6	129.50 (14)
C4—C8—H8	120.2	C3—O1—C2	116.97 (15)
N2—C9—C10	105.05 (14)
O2—C3—C4—C8	178.53 (18)	C10—C11—C13—C12	108.5 (2)
O1—C3—C4—C8	−0.3 (2)	N2—N3—N4—C10	0.3 (2)
O2—C3—C4—C5	0.2 (3)	C9—C10—N4—N3	−0.4 (2)
O1—C3—C4—C5	−178.58 (15)	C11—C10—N4—N3	−178.48 (16)
C8—C4—C5—N1	0.1 (3)	C7—C6—N1—C5	0.1 (3)
C3—C4—C5—N1	178.47 (16)	N2—C6—N1—C5	179.08 (14)
N1—C6—C7—C8	0.0 (3)	C4—C5—N1—C6	−0.1 (3)
N2—C6—C7—C8	−178.94 (15)	N4—N3—N2—C9	−0.2 (2)
C6—C7—C8—C4	−0.1 (3)	N4—N3—N2—C6	178.13 (15)
C5—C4—C8—C7	0.0 (3)	C10—C9—N2—N3	−0.04 (19)
C3—C4—C8—C7	−178.31 (16)	C10—C9—N2—C6	−178.15 (16)
N2—C9—C10—N4	0.24 (19)	N1—C6—N2—N3	−171.57 (14)
N2—C9—C10—C11	178.12 (17)	C7—C6—N2—N3	7.5 (2)
C9—C10—C11—C13	155.10 (19)	N1—C6—N2—C9	6.4 (3)
N4—C10—C11—C13	−27.3 (3)	C7—C6—N2—C9	−174.54 (16)
C9—C10—C11—C12	−135.4 (2)	O2—C3—O1—C2	−2.2 (3)
N4—C10—C11—C12	42.2 (3)	C4—C3—O1—C2	176.58 (15)
C10—C11—C12—C13	−110.0 (2)	C1—C2—O1—C3	−178.22 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1i	0.93	2.60	3.375 (2)	141
C7—H7···N3ii	0.93	2.42	3.245 (2)	147
C9—H9···O2i	0.93	2.54	3.422 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1i	0.93	2.60	3.375 (2)	141
C7—H7⋯N3ii	0.93	2.42	3.245 (2)	147
C9—H9⋯O2i	0.93	2.54	3.422 (2)	159

Symmetry codes: (i) ; (ii) .