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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2954.
Published online 2010 October 30. doi:  10.1107/S1600536810042376
PMCID: PMC3009239

Triflumizole

Abstract

In the title compound {systematic name: 4-chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethyl­idene]-2-(trifluoro­meth­yl)aniline}, C15H15ClF3N3O, the dihedral angle between the aniline and imidazole ring planes is 81.80 (4)°. In the crystal structure, weak inter­molecular C—H(...)X (X = N, O or F) hydrogen bonds and C—H(...)π inter­actions help to consolidate the packing.

Related literature

For the toxicity and insecticidal properties of the title compound, see: İnam et al. (2006 [triangle]); Nakata et al. (1991 [triangle]). For related structures, see: Long et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2954-scheme1.jpg

Experimental

Crystal data

  • C15H15ClF3N3O
  • M r = 345.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2954-efi2.jpg
  • a = 9.2815 (6) Å
  • b = 20.5078 (14) Å
  • c = 8.6339 (6) Å
  • β = 100.835 (1)°
  • V = 1614.11 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 173 K
  • 0.15 × 0.13 × 0.11 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.960, T max = 0.971
  • 16571 measured reflections
  • 4028 independent reflections
  • 3317 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.096
  • S = 1.03
  • 4028 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.28 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042376/jh2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042376/jh2218Isup2.hkl

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

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0016386).

supplementary crystallographic information

Comment

Triflumizole (systematic name: [(E)-4-chloro-α,α,α-trifluoro- N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine]), is a well known fungicide discoverd by Nippon Soda Co. Ltd., Japan (İnam et al., 2006; Nakata et al., 1991). However it's crystal structure has not been reported yet.

In the title compound (Scheme 1, Fig.1), the dihedral angle between the paniline and imidazole ring planes is 81.80 (4)°. All bond lengths and bond angles of core part consisting of aniline and methylimidazole groups are are comparable to those observed in similar structures (Long et al., 2008).

In the crystal structure, as shown in Fig. 2, weak C—H···X (X = N, O or F) hydrogen bonds are observed (Table 1). Weak intermolecular C—H···π interactions with 3.64 Å also exist. These intermolecular interactions may be contribute to the stabilization of the packing.

Experimental

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

Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 and d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
Crystal packing of the title compound with intermolecular C—H···X (X = N, O, or F) and C—H···π interactions shown as dashed lines. H atoms not involved in intermolecular interactions ...

Crystal data

C15H15ClF3N3OF(000) = 712
Mr = 345.75Dx = 1.423 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5704 reflections
a = 9.2815 (6) Åθ = 2.2–28.2°
b = 20.5078 (14) ŵ = 0.27 mm1
c = 8.6339 (6) ÅT = 173 K
β = 100.835 (1)°Block, colourless
V = 1614.11 (19) Å30.15 × 0.13 × 0.11 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer4028 independent reflections
Radiation source: fine-focus sealed tube3317 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.960, Tmax = 0.971k = −27→26
16571 measured reflectionsl = −11→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0411P)2 + 0.5111P] where P = (Fo2 + 2Fc2)/3
4028 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/Ueq
Cl11.49537 (5)0.75199 (2)0.20992 (6)0.05563 (14)
F10.88158 (9)0.70250 (5)0.32069 (12)0.0519 (3)
F21.00525 (12)0.66642 (5)0.53792 (12)0.0601 (3)
F31.03828 (12)0.76378 (5)0.46407 (13)0.0573 (3)
N11.01160 (11)0.57214 (5)0.27790 (12)0.0262 (2)
N20.80266 (11)0.51277 (5)0.19825 (12)0.0253 (2)
N30.60502 (12)0.44946 (6)0.16697 (13)0.0331 (3)
O10.81606 (10)0.56645 (4)−0.10396 (10)0.0282 (2)
C11.01505 (16)0.70258 (7)0.41218 (17)0.0362 (3)
C21.13094 (14)0.67960 (6)0.32611 (15)0.0277 (3)
C31.24709 (15)0.72066 (6)0.31239 (16)0.0331 (3)
H31.25530.76220.36170.040*
C41.34990 (15)0.70066 (7)0.22698 (17)0.0340 (3)
C51.33924 (15)0.64078 (7)0.15219 (17)0.0337 (3)
H51.40960.62800.09110.040*
C61.22451 (14)0.59969 (6)0.16759 (15)0.0298 (3)
H61.21750.55820.11790.036*
C71.11926 (13)0.61799 (6)0.25445 (14)0.0250 (2)
C80.89657 (13)0.56432 (6)0.17534 (14)0.0244 (2)
C90.66245 (13)0.50171 (6)0.11769 (15)0.0276 (3)
H90.61310.52900.03560.033*
C100.71276 (16)0.42502 (7)0.28583 (17)0.0365 (3)
H100.70260.38670.34460.044*
C110.83378 (15)0.46272 (7)0.30736 (16)0.0328 (3)
H110.92200.45630.38180.039*
C120.84433 (15)0.60608 (6)0.03188 (15)0.0305 (3)
H12A0.75380.62950.04390.037*
H12B0.92020.63890.02110.037*
C130.74287 (15)0.60238 (7)−0.23828 (15)0.0316 (3)
H13A0.80800.6373−0.26430.038*
H13B0.65320.6230−0.21420.038*
C140.70299 (16)0.55717 (7)−0.37587 (16)0.0364 (3)
H14A0.64240.5211−0.34690.044*
H14B0.79360.5381−0.40180.044*
C150.61863 (18)0.59207 (9)−0.51998 (17)0.0450 (4)
H15A0.52880.6109−0.49480.067*
H15B0.59310.5609−0.60690.067*
H15C0.67960.6269−0.55120.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0433 (2)0.0460 (2)0.0761 (3)−0.02137 (18)0.0072 (2)0.0045 (2)
F10.0325 (5)0.0604 (6)0.0595 (6)0.0106 (4)0.0002 (4)−0.0165 (5)
F20.0738 (7)0.0644 (7)0.0487 (6)0.0213 (5)0.0286 (5)0.0098 (5)
F30.0570 (6)0.0406 (5)0.0737 (7)0.0044 (4)0.0108 (5)−0.0297 (5)
N10.0267 (5)0.0227 (5)0.0269 (5)−0.0006 (4)−0.0003 (4)−0.0005 (4)
N20.0244 (5)0.0243 (5)0.0253 (5)−0.0015 (4)−0.0002 (4)0.0002 (4)
N30.0271 (5)0.0376 (6)0.0344 (6)−0.0056 (5)0.0048 (5)−0.0006 (5)
O10.0319 (5)0.0266 (4)0.0238 (4)0.0014 (4)−0.0008 (3)0.0011 (3)
C10.0377 (7)0.0304 (7)0.0379 (7)0.0050 (6)0.0007 (6)−0.0067 (6)
C20.0290 (6)0.0236 (6)0.0273 (6)0.0025 (5)−0.0032 (5)−0.0023 (5)
C30.0363 (7)0.0219 (6)0.0363 (7)−0.0030 (5)−0.0057 (6)−0.0032 (5)
C40.0291 (6)0.0288 (7)0.0405 (7)−0.0075 (5)−0.0025 (5)0.0042 (5)
C50.0297 (7)0.0331 (7)0.0376 (7)0.0004 (5)0.0046 (5)0.0011 (5)
C60.0314 (6)0.0233 (6)0.0331 (6)0.0000 (5)0.0020 (5)−0.0043 (5)
C70.0251 (6)0.0210 (6)0.0255 (6)−0.0004 (4)−0.0036 (4)0.0001 (4)
C80.0269 (6)0.0199 (5)0.0251 (5)0.0006 (4)0.0015 (5)−0.0016 (4)
C90.0218 (6)0.0324 (6)0.0274 (6)−0.0008 (5)0.0017 (5)−0.0021 (5)
C100.0362 (7)0.0334 (7)0.0390 (7)−0.0065 (6)0.0047 (6)0.0067 (6)
C110.0318 (7)0.0303 (7)0.0330 (7)−0.0016 (5)−0.0023 (5)0.0068 (5)
C120.0368 (7)0.0221 (6)0.0282 (6)−0.0036 (5)−0.0049 (5)0.0016 (5)
C130.0366 (7)0.0303 (7)0.0255 (6)−0.0019 (5)0.0000 (5)0.0058 (5)
C140.0363 (7)0.0427 (8)0.0281 (6)0.0066 (6)0.0006 (5)−0.0022 (6)
C150.0466 (9)0.0602 (10)0.0257 (7)0.0056 (7)0.0005 (6)0.0017 (6)

Geometric parameters (Å, °)

Cl1—C41.7399 (14)C5—H50.9500
F1—C11.3382 (17)C6—C71.3903 (18)
F2—C11.3318 (18)C6—H60.9500
F3—C11.3364 (16)C8—C121.5089 (16)
N1—C81.2626 (15)C9—H90.9500
N1—C71.4141 (16)C10—C111.3473 (19)
N2—C91.3743 (16)C10—H100.9500
N2—C111.3865 (16)C11—H110.9500
N2—C81.4076 (16)C12—H12A0.9900
N3—C91.3033 (17)C12—H12B0.9900
N3—C101.3851 (18)C13—C141.4976 (19)
O1—C121.4104 (15)C13—H13A0.9900
O1—C131.4328 (15)C13—H13B0.9900
C1—C21.4940 (19)C14—C151.5189 (19)
C2—C31.3904 (19)C14—H14A0.9900
C2—C71.4022 (16)C14—H14B0.9900
C3—C41.374 (2)C15—H15A0.9800
C3—H30.9500C15—H15B0.9800
C4—C51.382 (2)C15—H15C0.9800
C5—C61.3839 (18)
C8—N1—C7120.74 (10)N3—C9—N2112.15 (11)
C9—N2—C11106.15 (10)N3—C9—H9123.9
C9—N2—C8127.26 (10)N2—C9—H9123.9
C11—N2—C8126.59 (10)C11—C10—N3111.21 (12)
C9—N3—C10104.87 (11)C11—C10—H10124.4
C12—O1—C13111.25 (9)N3—C10—H10124.4
F2—C1—F3106.33 (12)C10—C11—N2105.62 (12)
F2—C1—F1106.44 (13)C10—C11—H11127.2
F3—C1—F1105.80 (11)N2—C11—H11127.2
F2—C1—C2113.31 (11)O1—C12—C8109.66 (10)
F3—C1—C2112.15 (12)O1—C12—H12A109.7
F1—C1—C2112.28 (11)C8—C12—H12A109.7
C3—C2—C7120.33 (12)O1—C12—H12B109.7
C3—C2—C1119.58 (11)C8—C12—H12B109.7
C7—C2—C1120.04 (12)H12A—C12—H12B108.2
C4—C3—C2119.53 (12)O1—C13—C14109.42 (11)
C4—C3—H3120.2O1—C13—H13A109.8
C2—C3—H3120.2C14—C13—H13A109.8
C3—C4—C5121.34 (12)O1—C13—H13B109.8
C3—C4—Cl1119.55 (11)C14—C13—H13B109.8
C5—C4—Cl1119.10 (11)H13A—C13—H13B108.2
C4—C5—C6119.00 (13)C13—C14—C15111.75 (12)
C4—C5—H5120.5C13—C14—H14A109.3
C6—C5—H5120.5C15—C14—H14A109.3
C5—C6—C7121.26 (12)C13—C14—H14B109.3
C5—C6—H6119.4C15—C14—H14B109.3
C7—C6—H6119.4H14A—C14—H14B107.9
C6—C7—C2118.52 (11)C14—C15—H15A109.5
C6—C7—N1119.00 (11)C14—C15—H15B109.5
C2—C7—N1122.29 (11)H15A—C15—H15B109.5
N1—C8—N2117.46 (11)C14—C15—H15C109.5
N1—C8—C12127.05 (11)H15A—C15—H15C109.5
N2—C8—C12115.44 (10)H15B—C15—H15C109.5
F2—C1—C2—C3−118.75 (14)C8—N1—C7—C2100.78 (14)
F3—C1—C2—C31.64 (18)C7—N1—C8—N2172.85 (11)
F1—C1—C2—C3120.62 (14)C7—N1—C8—C12−9.71 (19)
F2—C1—C2—C763.75 (16)C9—N2—C8—N1168.55 (12)
F3—C1—C2—C7−175.86 (11)C11—N2—C8—N1−11.52 (18)
F1—C1—C2—C7−56.88 (17)C9—N2—C8—C12−9.19 (18)
C7—C2—C3—C40.52 (19)C11—N2—C8—C12170.74 (12)
C1—C2—C3—C4−176.98 (13)C10—N3—C9—N20.04 (15)
C2—C3—C4—C50.9 (2)C11—N2—C9—N3−0.19 (15)
C2—C3—C4—Cl1−179.94 (10)C8—N2—C9—N3179.75 (11)
C3—C4—C5—C6−1.7 (2)C9—N3—C10—C110.13 (16)
Cl1—C4—C5—C6179.17 (10)N3—C10—C11—N2−0.24 (16)
C4—C5—C6—C71.0 (2)C9—N2—C11—C100.25 (15)
C5—C6—C7—C20.40 (19)C8—N2—C11—C10−179.68 (12)
C5—C6—C7—N1−174.60 (11)C13—O1—C12—C8170.09 (10)
C3—C2—C7—C6−1.17 (18)N1—C8—C12—O1127.19 (13)
C1—C2—C7—C6176.31 (12)N2—C8—C12—O1−55.33 (14)
C3—C2—C7—N1173.65 (11)C12—O1—C13—C14−174.92 (11)
C1—C2—C7—N1−8.86 (18)O1—C13—C14—C15177.36 (12)
C8—N1—C7—C6−84.42 (15)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2,C9,N3,C10,C11 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···N3i0.952.723.4383 (18)133
C6—H6···O1i0.952.583.4604 (16)155
C11—H11···F2ii0.952.663.2063 (17)117
C12—H12B···F3iii0.992.373.3320 (16)163
C15—H15B···Cgiv0.982.823.6385 (18)141

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+1, −z+1; (iii) x, −y+3/2, z−1/2; (iv) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2218).

References

  • Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • İnam, R., Gülerman, E. Z. & Sarigül, T. (2006). Anal. Chim. Acta, 579, 117–123. [PubMed]
  • Long, S., Muthusamy, V., Willis, P. G., Parkin, S. & Cammers, A. (2008). Beilstein J. Org. Chem.4, No. 23. [PMC free article] [PubMed]
  • Nakata, A., Hashimoto, S., Ikura, K. & Katsuura, K. (1991). J. Pestic. Sci.16, 301–313.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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