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

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ISSN: 2056-9890

Imaza­lil: 1-[2-(2,4-di­chloro­phen­yl)-2-(prop-2-en­yl­oxy)eth­yl]-1H-imidazole

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and bTest & Analytical Laboratory, Korea Food & Drug Administration, 123-7 Yongdang-dong, Busan 608-829, Republic of Korea
*Correspondence e-mail: kmpark@gnu.ac.kr, thkim@gnu.ac.kr

(Received 11 May 2011; accepted 13 May 2011; online 20 May 2011)

In the title compound, C14H14Cl2N2O, the imidazole ring is almost parallel to the benzene ring, the dihedral angle between them being 7.3 (2)°. In the crystal, there is an inter­molecular C—Cl⋯π inter­action (Cl⋯centroid = 3.36 Å and C—Cl⋯centroid = 89.2°). In addition, a Cl⋯Cl contact of 3.411 (1) Å and an inter­molecular C—H⋯N hydrogen bond are observed. These inter­actions contribute to the stabilization of the crystal packing.

Related literature

For information on the toxicity of the title compound, see: Sisman & Türkez (2010[Sisman, T. & Türkez, H. (2010). Toxicol. Ind. Health, 26, 641-648.]). For related structures, see: Bisaha et al. (2005[Bisaha, S. N., Malley, M. F., Pudzianowski, A., Monshizadegan, H., Wang, P., Madsen, C. S., Gougoutas, J. Z. & Stein, P. (2005). Bioorg. Med. Chem. Lett. 15, 2749-2751.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14Cl2N2O

  • Mr = 297.17

  • Monoclinic, P 21 /c

  • a = 7.9374 (6) Å

  • b = 13.4144 (12) Å

  • c = 13.479 (1) Å

  • β = 103.386 (5)°

  • V = 1396.19 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.46 mm−1

  • T = 173 K

  • 0.20 × 0.09 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.914, Tmax = 0.964

  • 12201 measured reflections

  • 3040 independent reflections

  • 2282 reflections with I > 2σ(I)

  • Rint = 0.069

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.119

  • S = 1.08

  • 3040 reflections

  • 172 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯N2i 0.95 2.66 3.562 (3) 159
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Imazalil (systematic name: 1-[2-(2,4-dichlorophenyl)-2- (2-propen-1-yloxy)ethyl]-1H-imidazole) is a fungicide widely used in agriculture, particularly in the growth of citrus fruits. It is also known as "enilconazole" (Sisman & Türkez, 2010). However,until now its crystal structure has not been reported.

In the title compound (Fig. 1), the imidazole ring is almost parallel to the benzene ring, the dihedral angle between them being 7.3 (2)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Bisaha et al. 2005).

In the crystal structure, as shown in Fig. 2, weak intermolecular C—H···N hydrogen bonds (Table 1) and a Cl···Cl contact of 3.411 (1) Å are observed. There are also C—Cl···π interactions involving chlorine Cl2 and benzene ring (C1–C6), with a Cl···centroid (Cgiii) distance of 3.36 Å and a C3—Cl2···Cgiii angle of 89.2° [symmetry code: (iii) -x + 1, -y + 2, -z + 1] (Fig. 2). These intermolecular interactions may contribute to the stabilization of the crystal packing.

Related literature top

For information on the toxicity of the title compound, see: Sisman & Türkez (2010). For related structures, see: Bisaha et al. (2005).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

The H atoms were geometrically positioned and refined as riding. C—H = 0.95 Å for Csp2, C—H = 0.99 Å for methylene C and C—H = 1.00 Å for methine C; Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing of the title compound with intermolecular C—H···N hydrogen bonds, C—Cl···π interactions and Cl···Cl contacts shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. [Symmetry codes: (i) -x + 2, -y + 2, -z + 1; (ii) x + 1, -y + 1.5, z + 1/2; (iii) -x + 1, -y + 2, -z + 1; (iv) -x, y + 1/2, -z + 1/2; (v) x - 1, y, z.]
1-[2-(2,4-dichlorophenyl)-2-(prop-2-enyloxy)ethyl]-1H-imidazole top
Crystal data top
C14H14Cl2N2OF(000) = 616
Mr = 297.17Dx = 1.414 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2420 reflections
a = 7.9374 (6) Åθ = 2.2–28.4°
b = 13.4144 (12) ŵ = 0.46 mm1
c = 13.479 (1) ÅT = 173 K
β = 103.386 (5)°Plate, colourless
V = 1396.19 (19) Å30.20 × 0.09 × 0.08 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3040 independent reflections
Radiation source: fine-focus sealed tube2282 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 910
Tmin = 0.914, Tmax = 0.964k = 1714
12201 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0525P)2 + 0.2498P]
where P = (Fo2 + 2Fc2)/3
3040 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C14H14Cl2N2OV = 1396.19 (19) Å3
Mr = 297.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9374 (6) ŵ = 0.46 mm1
b = 13.4144 (12) ÅT = 173 K
c = 13.479 (1) Å0.20 × 0.09 × 0.08 mm
β = 103.386 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
3040 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2282 reflections with I > 2σ(I)
Tmin = 0.914, Tmax = 0.964Rint = 0.069
12201 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.08Δρmax = 0.37 e Å3
3040 reflectionsΔρmin = 0.27 e Å3
172 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
xyzUiso*/Ueq
Cl10.41595 (8)0.69956 (5)0.57733 (5)0.0410 (2)
Cl20.77994 (7)0.98990 (4)0.47431 (5)0.03569 (19)
O10.0431 (2)0.71310 (11)0.25901 (12)0.0294 (4)
N10.1440 (2)0.69576 (14)0.40437 (15)0.0289 (4)
N20.3936 (3)0.60867 (17)0.34432 (19)0.0465 (6)
C10.4327 (3)0.78309 (16)0.48568 (17)0.0282 (5)
C20.5822 (3)0.84344 (16)0.51200 (18)0.0285 (5)
H20.66680.83630.57420.034*
C30.5937 (3)0.91175 (16)0.44116 (18)0.0279 (5)
C40.4636 (3)0.91953 (16)0.34627 (18)0.0297 (5)
H40.47750.96890.29820.036*
C50.3172 (3)0.85669 (16)0.32241 (18)0.0277 (5)
H50.23430.86320.25940.033*
C60.2977 (3)0.78727 (15)0.39102 (17)0.0255 (5)
C70.1325 (3)0.72205 (16)0.36550 (17)0.0253 (5)
H70.16050.65400.39490.030*
C80.0025 (3)0.76633 (17)0.40885 (19)0.0311 (5)
H8A0.04690.78540.48060.037*
H8B0.04740.82740.37040.037*
C90.3009 (3)0.68361 (19)0.3287 (2)0.0377 (6)
H90.33450.72690.27180.045*
C100.2883 (4)0.5710 (2)0.4355 (2)0.0505 (7)
H100.31970.51390.46880.061*
C110.1353 (4)0.6230 (2)0.4733 (2)0.0440 (6)
H110.04710.61020.53280.053*
C120.1149 (3)0.63442 (17)0.21546 (18)0.0312 (5)
H12A0.24260.64100.23440.037*
H12B0.07770.64010.14030.037*
C130.0682 (3)0.53464 (18)0.24568 (19)0.0350 (6)
H130.05080.51670.23110.042*
C140.1862 (4)0.4672 (2)0.2933 (2)0.0451 (7)
H14B0.30600.48330.30870.054*
H14A0.14930.40370.31120.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0519 (4)0.0404 (4)0.0294 (3)0.0131 (3)0.0066 (3)0.0096 (3)
Cl20.0339 (3)0.0338 (3)0.0442 (4)0.0075 (2)0.0189 (3)0.0031 (3)
O10.0340 (8)0.0319 (8)0.0244 (8)0.0010 (7)0.0111 (7)0.0023 (7)
N10.0320 (10)0.0296 (10)0.0285 (10)0.0003 (8)0.0139 (9)0.0005 (8)
N20.0390 (12)0.0524 (14)0.0515 (15)0.0104 (11)0.0170 (11)0.0142 (12)
C10.0376 (12)0.0253 (11)0.0253 (12)0.0009 (10)0.0147 (10)0.0020 (9)
C20.0310 (12)0.0305 (12)0.0256 (12)0.0001 (10)0.0098 (10)0.0012 (10)
C30.0286 (11)0.0249 (11)0.0347 (13)0.0021 (9)0.0168 (10)0.0065 (10)
C40.0362 (12)0.0251 (11)0.0337 (13)0.0022 (9)0.0203 (11)0.0035 (10)
C50.0305 (12)0.0288 (12)0.0256 (12)0.0033 (9)0.0104 (10)0.0002 (10)
C60.0315 (12)0.0233 (11)0.0253 (11)0.0030 (9)0.0142 (10)0.0022 (9)
C70.0313 (11)0.0236 (11)0.0225 (11)0.0007 (9)0.0090 (10)0.0019 (9)
C80.0399 (13)0.0259 (12)0.0324 (13)0.0017 (10)0.0183 (11)0.0032 (10)
C90.0362 (13)0.0440 (14)0.0357 (14)0.0031 (11)0.0136 (12)0.0004 (12)
C100.0503 (16)0.0398 (15)0.066 (2)0.0085 (13)0.0237 (16)0.0085 (14)
C110.0441 (15)0.0475 (15)0.0410 (15)0.0023 (12)0.0109 (13)0.0163 (13)
C120.0367 (13)0.0334 (12)0.0277 (12)0.0062 (10)0.0159 (11)0.0058 (10)
C130.0403 (13)0.0357 (13)0.0319 (13)0.0111 (11)0.0143 (11)0.0077 (11)
C140.0631 (18)0.0383 (14)0.0387 (15)0.0040 (13)0.0219 (14)0.0038 (12)
Geometric parameters (Å, º) top
Cl1—C11.696 (2)C5—H50.9500
Cl2—C31.783 (2)C6—C71.547 (3)
O1—C121.392 (3)C7—C81.461 (3)
O1—C71.452 (3)C7—H71.0000
N1—C111.338 (3)C8—H8A0.9900
N1—C91.425 (3)C8—H8B0.9900
N1—C81.459 (3)C9—H90.9500
N2—C91.291 (3)C10—C111.391 (4)
N2—C101.410 (4)C10—H100.9500
C1—C21.412 (3)C11—H110.9500
C1—C61.465 (3)C12—C131.471 (3)
C2—C31.342 (3)C12—H12A0.9900
C2—H20.9500C12—H12B0.9900
C3—C41.450 (3)C13—C141.353 (4)
C4—C51.411 (3)C13—H130.9500
C4—H40.9500C14—H14B0.9500
C5—C61.346 (3)C14—H14A0.9500
C12—O1—C7108.98 (17)C6—C7—H7109.2
C11—N1—C9108.0 (2)N1—C8—C7110.39 (18)
C11—N1—C8121.9 (2)N1—C8—H8A109.6
C9—N1—C8129.8 (2)C7—C8—H8A109.6
C9—N2—C10100.1 (2)N1—C8—H8B109.6
C2—C1—C6126.8 (2)C7—C8—H8B109.6
C2—C1—Cl1113.51 (18)H8A—C8—H8B108.1
C6—C1—Cl1119.65 (16)N2—C9—N1114.1 (2)
C3—C2—C1113.9 (2)N2—C9—H9122.9
C3—C2—H2123.1N1—C9—H9122.9
C1—C2—H2123.1C11—C10—N2115.5 (2)
C2—C3—C4121.7 (2)C11—C10—H10122.2
C2—C3—Cl2114.37 (18)N2—C10—H10122.2
C4—C3—Cl2123.96 (17)N1—C11—C10102.2 (2)
C5—C4—C3122.6 (2)N1—C11—H11128.9
C5—C4—H4118.7C10—C11—H11128.9
C3—C4—H4118.7O1—C12—C13114.76 (18)
C6—C5—C4118.4 (2)O1—C12—H12A108.6
C6—C5—H5120.8C13—C12—H12A108.6
C4—C5—H5120.8O1—C12—H12B108.6
C5—C6—C1116.6 (2)C13—C12—H12B108.6
C5—C6—C7117.7 (2)H12A—C12—H12B107.6
C1—C6—C7125.69 (19)C14—C13—C12123.3 (2)
O1—C7—C8101.13 (18)C14—C13—H13118.4
O1—C7—C6117.51 (17)C12—C13—H13118.4
C8—C7—C6110.10 (17)C13—C14—H14B120.0
O1—C7—H7109.2C13—C14—H14A120.0
C8—C7—H7109.2H14B—C14—H14A120.0
C6—C1—C2—C31.4 (3)C1—C6—C7—O1160.79 (18)
Cl1—C1—C2—C3178.10 (16)C5—C6—C7—C893.1 (2)
C1—C2—C3—C41.0 (3)C1—C6—C7—C884.2 (3)
C1—C2—C3—Cl2179.00 (15)C11—N1—C8—C780.7 (3)
C2—C3—C4—C50.3 (3)C9—N1—C8—C793.6 (3)
Cl2—C3—C4—C5179.78 (16)O1—C7—C8—N167.1 (2)
C3—C4—C5—C60.4 (3)C6—C7—C8—N1167.88 (18)
C4—C5—C6—C10.1 (3)C10—N2—C9—N10.1 (3)
C4—C5—C6—C7177.48 (18)C11—N1—C9—N20.2 (3)
C2—C1—C6—C50.8 (3)C8—N1—C9—N2175.2 (2)
Cl1—C1—C6—C5178.64 (16)C9—N2—C10—C110.0 (3)
C2—C1—C6—C7178.2 (2)C9—N1—C11—C100.2 (3)
Cl1—C1—C6—C71.3 (3)C8—N1—C11—C10175.6 (2)
C12—O1—C7—C8152.67 (17)N2—C10—C11—N10.2 (3)
C12—O1—C7—C687.5 (2)C7—O1—C12—C1373.9 (2)
C5—C6—C7—O121.8 (3)O1—C12—C13—C14120.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N2i0.952.663.562 (3)159
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H14Cl2N2O
Mr297.17
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)7.9374 (6), 13.4144 (12), 13.479 (1)
β (°) 103.386 (5)
V3)1396.19 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.46
Crystal size (mm)0.20 × 0.09 × 0.08
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.914, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
12201, 3040, 2282
Rint0.069
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.119, 1.08
No. of reflections3040
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.27

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N2i0.952.663.562 (3)159
Symmetry code: (i) x, y+1/2, z+1/2.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Korea government (MEST) (No. 2010–0018586).

References

First citationBisaha, S. N., Malley, M. F., Pudzianowski, A., Monshizadegan, H., Wang, P., Madsen, C. S., Gougoutas, J. Z. & Stein, P. (2005). Bioorg. Med. Chem. Lett. 15, 2749–2751.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSisman, T. & Türkez, H. (2010). Toxicol. Ind. Health, 26, 641–648.  Web of Science CrossRef CAS PubMed Google Scholar

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