1-[2-(2,4-Dichloro-phenyl)-pent-yl]-1H-1,2,4-triazole.

The title compound, C(13)H(15)Cl(2)N(3), also known as penconazole, crystallizes as a racemate. The dihedral angle between the benzene and triazole rings is 24.96 (13)°. In the crystal structure, mol-ecules are linked into chains running parallel to the c axis by inter-molecular C-H⋯N hydrogen-bonding inter-actions.

Related literature

For the synthesis and toxicity of the title compound, see: Maier et al. (1987 ▶); Worthing (1987 ▶); Tao et al. (2003 ▶). For the crystal structure of a related compound, see: Peeters et al. (1993 ▶).

Experimental

Crystal data

C13H15Cl2N3

M = 284.18

Monoclinic,

a = 25.083 (8) Å

b = 10.763 (2) Å

c = 11.206 (3) Å

β = 105.654 (3)°

V = 2913.1 (13) Å3

Z = 8

Cu Kα radiation

μ = 3.89 mm−1

T = 297 K

0.23 × 0.20 × 0.16 mm

Data collection

Siemens AED diffractometer

Absorption correction: empirical (refined from ΔF) (DIFABS; Walker & Stuart, 1983 ▶) T min = 0.432, T max = 0.538

2737 measured reflections

2611 independent reflections

1183 reflections with I > 2σ(I)

R int = 0.060

3 standard reflections every 100 reflections intensity decay: 0.01%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.127

S = 0.99

2611 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

Data collection: AED (Belletti et al., 1993 ▶); cell refinement: AED; data reduction: AED; 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, 1997 ▶) and SCHAKAL (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007120/hg2483sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007120/hg2483Isup2.hkl

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

C13H15Cl2N3	F(000) = 1184
Mr = 284.18	Dx = 1.296 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 48 reflections
a = 25.083 (8) Å	θ = 18.4–42.5°
b = 10.763 (2) Å	µ = 3.89 mm−1
c = 11.206 (3) Å	T = 297 K
β = 105.654 (3)°	Block, colourless
V = 2913.1 (13) Å3	0.23 × 0.20 × 0.16 mm
Z = 8

Siemens AED diffractometer	1183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
graphite	θmax = 67.9°, θmin = 3.7°
θ/2θ scans	h = −29→28
Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)	k = −2→12
Tmin = 0.432, Tmax = 0.538	l = −5→13
2737 measured reflections	3 standard reflections every 100 reflections
2611 independent reflections	intensity decay: 0.01%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0456P)2] where P = (Fo2 + 2Fc2)/3
2611 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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
Cl1	0.08070 (6)	0.51687 (9)	0.93474 (12)	0.1422 (6)
Cl2	0.08744 (5)	0.18168 (11)	1.28987 (10)	0.1305 (5)
N1	0.22774 (10)	0.3780 (2)	0.7443 (2)	0.0595 (7)
N2	0.24356 (12)	0.3032 (2)	0.6633 (2)	0.0757 (8)
N3	0.25582 (12)	0.5043 (2)	0.6210 (3)	0.0815 (9)
C1	0.25951 (15)	0.3839 (3)	0.5932 (3)	0.0808 (10)
H1	0.2728	0.3591	0.5270	0.097*
C2	0.23549 (13)	0.4960 (3)	0.7196 (3)	0.0714 (9)
H2	0.2279	0.5634	0.7644	0.086*
C3	0.20829 (13)	0.3285 (3)	0.8460 (3)	0.0638 (8)
H3A	0.2230	0.3790	0.9192	0.077*
H3B	0.2226	0.2449	0.8646	0.077*
C4	0.14554 (13)	0.3253 (3)	0.8180 (3)	0.0666 (8)
H4	0.1313	0.4086	0.7921	0.080*
C5	0.13060 (12)	0.2927 (3)	0.9380 (3)	0.0648 (8)
C6	0.10164 (15)	0.3713 (3)	0.9946 (3)	0.0807 (10)
C7	0.08852 (16)	0.3387 (3)	1.1047 (4)	0.0927 (11)
H7	0.0695	0.3937	1.1424	0.111*
C8	0.10441 (15)	0.2235 (4)	1.1558 (3)	0.0790 (10)
C9	0.13257 (14)	0.1450 (3)	1.1013 (3)	0.0787 (10)
H9	0.1435	0.0680	1.1372	0.094*
C10	0.14543 (13)	0.1774 (3)	0.9930 (3)	0.0724 (9)
H10	0.1643	0.1211	0.9562	0.087*
C11	0.11930 (14)	0.2323 (3)	0.7113 (3)	0.0830 (10)
H11A	0.1315	0.2537	0.6389	0.100*
H11B	0.1326	0.1492	0.7368	0.100*
C12	0.05814 (16)	0.2321 (4)	0.6773 (3)	0.1057 (13)
H12A	0.0450	0.3152	0.6514	0.127*
H12B	0.0460	0.2115	0.7501	0.127*
C13	0.03234 (16)	0.1433 (4)	0.5764 (4)	0.1191 (15)
H131	−0.0072	0.1482	0.5589	0.179*
H132	0.0442	0.0604	0.6020	0.179*
H133	0.0434	0.1640	0.5032	0.179*

	U11	U22	U33	U12	U13	U23
Cl1	0.2339 (15)	0.0687 (6)	0.1461 (10)	0.0447 (8)	0.0895 (10)	0.0118 (7)
Cl2	0.1620 (11)	0.1516 (11)	0.0905 (7)	−0.0169 (8)	0.0558 (7)	0.0066 (7)
N1	0.0728 (18)	0.0384 (12)	0.0602 (15)	−0.0030 (12)	0.0061 (13)	−0.0050 (12)
N2	0.103 (2)	0.0486 (14)	0.0760 (18)	−0.0110 (15)	0.0248 (16)	−0.0087 (14)
N3	0.101 (2)	0.0588 (17)	0.081 (2)	−0.0131 (15)	0.0183 (18)	0.0088 (15)
C1	0.111 (3)	0.0566 (19)	0.075 (2)	−0.016 (2)	0.026 (2)	−0.0020 (18)
C2	0.084 (3)	0.0447 (17)	0.079 (2)	−0.0054 (16)	0.0105 (19)	−0.0048 (17)
C3	0.076 (2)	0.0485 (16)	0.0612 (19)	−0.0073 (15)	0.0083 (16)	0.0029 (15)
C4	0.072 (2)	0.0545 (18)	0.067 (2)	0.0001 (16)	0.0072 (17)	0.0065 (16)
C5	0.064 (2)	0.0564 (18)	0.066 (2)	−0.0038 (16)	0.0049 (16)	−0.0013 (16)
C6	0.105 (3)	0.057 (2)	0.082 (2)	−0.003 (2)	0.027 (2)	−0.0030 (19)
C7	0.109 (3)	0.079 (3)	0.094 (3)	−0.006 (2)	0.035 (2)	−0.019 (2)
C8	0.086 (3)	0.089 (3)	0.064 (2)	−0.015 (2)	0.0244 (19)	0.002 (2)
C9	0.079 (2)	0.074 (2)	0.079 (2)	−0.0020 (19)	0.014 (2)	0.019 (2)
C10	0.073 (2)	0.066 (2)	0.076 (2)	0.0035 (17)	0.0154 (18)	0.0082 (18)
C11	0.084 (3)	0.094 (3)	0.060 (2)	−0.011 (2)	0.0009 (18)	−0.0074 (19)
C12	0.096 (3)	0.121 (3)	0.091 (3)	−0.026 (3)	0.011 (2)	−0.011 (3)
C13	0.095 (3)	0.140 (4)	0.100 (3)	−0.016 (3)	−0.013 (2)	−0.030 (3)

Cl1—C6	1.729 (3)	C5—C10	1.391 (4)
Cl2—C8	1.728 (3)	C6—C7	1.404 (5)
N1—C2	1.326 (3)	C7—C8	1.379 (4)
N1—N2	1.351 (3)	C7—H7	0.9300
N1—C3	1.457 (3)	C8—C9	1.348 (4)
N2—C1	1.304 (4)	C9—C10	1.382 (4)
N3—C2	1.339 (4)	C9—H9	0.9300
N3—C1	1.342 (4)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.478 (4)
C2—H2	0.9300	C11—H11A	0.9700
C3—C4	1.520 (4)	C11—H11B	0.9700
C3—H3A	0.9700	C12—C13	1.488 (5)
C3—H3B	0.9700	C12—H12A	0.9700
C4—C5	1.530 (4)	C12—H12B	0.9700
C4—C11	1.562 (4)	C13—H131	0.9600
C4—H4	0.9800	C13—H132	0.9600
C5—C6	1.377 (4)	C13—H133	0.9600
C2—N1—N2	110.2 (3)	C8—C7—H7	120.7
C2—N1—C3	127.8 (3)	C6—C7—H7	120.7
N2—N1—C3	122.0 (2)	C9—C8—C7	120.2 (3)
C1—N2—N1	101.6 (2)	C9—C8—Cl2	120.9 (3)
C2—N3—C1	101.1 (3)	C7—C8—Cl2	118.9 (3)
N2—C1—N3	116.8 (3)	C8—C9—C10	121.0 (3)
N2—C1—H1	121.6	C8—C9—H9	119.5
N3—C1—H1	121.6	C10—C9—H9	119.5
N1—C2—N3	110.2 (3)	C9—C10—C5	121.1 (3)
N1—C2—H2	124.9	C9—C10—H10	119.5
N3—C2—H2	124.9	C5—C10—H10	119.5
N1—C3—C4	113.2 (2)	C12—C11—C4	113.1 (3)
N1—C3—H3A	108.9	C12—C11—H11A	109.0
C4—C3—H3A	108.9	C4—C11—H11A	109.0
N1—C3—H3B	108.9	C12—C11—H11B	109.0
C4—C3—H3B	108.9	C4—C11—H11B	109.0
H3A—C3—H3B	107.8	H11A—C11—H11B	107.8
C3—C4—C5	108.0 (2)	C11—C12—C13	113.9 (3)
C3—C4—C11	111.8 (3)	C11—C12—H12A	108.8
C5—C4—C11	111.9 (2)	C13—C12—H12A	108.8
C3—C4—H4	108.3	C11—C12—H12B	108.8
C5—C4—H4	108.3	C13—C12—H12B	108.8
C11—C4—H4	108.3	H12A—C12—H12B	107.7
C6—C5—C10	117.1 (3)	C12—C13—H131	109.5
C6—C5—C4	123.3 (3)	C12—C13—H132	109.5
C10—C5—C4	119.6 (3)	H131—C13—H132	109.5
C5—C6—C7	122.0 (3)	C12—C13—H133	109.5
C5—C6—Cl1	121.4 (3)	H131—C13—H133	109.5
C7—C6—Cl1	116.7 (3)	H132—C13—H133	109.5
C8—C7—C6	118.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N3i	0.97	2.52	3.489 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N3i	0.97	2.52	3.489 (4)	174

Symmetry code: (i) .