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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2954
https://doi.org/10.1107/S1600536810042376

Triflumizole

Tae Ho Kim,a Ki-Min Park,a* Yong Woon Shinb and Jineun Kima*

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, jekim@gnu.ac.kr

(Received 9 October 2010; accepted 19 October 2010; online 30 October 2010)

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[İnam, R., Gülerman, E. Z. & Sarigül, T. (2006). Anal. Chim. Acta, 579, 117-123.]); Nakata et al. (1991[Nakata, A., Hashimoto, S., Ikura, K. & Katsuura, K. (1991). J. Pestic. Sci. 16, 301-313.]). For related structures, see: Long et al. (2008[Long, S., Muthusamy, V., Willis, P. G., Parkin, S. & Cammers, A. (2008). Beilstein J. Org. Chem. 4, No. 23.]).

[Scheme 1]

Experimental

Crystal data

  • C15H15ClF3N3O

  • Mr = 345.75

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.960, Tmax = 0.971

  • 16571 measured reflections

  • 4028 independent reflections

  • 3317 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2,C9,N3,C10,C11 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯N3i 0.95 2.72 3.4383 (18) 133
C6—H6⋯O1i 0.95 2.58 3.4604 (16) 155
C11—H11⋯F2ii 0.95 2.66 3.2063 (17) 117
C12—H12B⋯F3iii 0.99 2.37 3.3320 (16) 163
C15—H15B⋯Cgiv 0.98 2.82 3.6385 (18) 141
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+1, -z+1; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) x, y, z-1.

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

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042376/jh2218Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

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, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] 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 have been omitted for clarity. Cg is the centroid of the N2/C9/N3/C10/C11 ring. [Symmetry codes: (i) -x + 2, -y + 1, -z; (ii) -x + 2, -y + 1, -z + 1; (iii) x, -y + 1.5, +z - 1/2; (iv) x, y, z + 1.)
4-chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethylidene]- 2-(trifluoromethyl)aniline top
Crystal data top
C15H15ClF3N3OF(000) = 712
Mr = 345.75Dx = 1.423 Mg m−3
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 mm−1
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 top
Bruker APEXII CCD
diffractometer		4028 independent reflections
Radiation source: fine-focus sealed tube3317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ 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 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.03 w = 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 Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C15H15ClF3N3OV = 1614.11 (19) Å3
Mr = 345.75Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2815 (6) ŵ = 0.27 mm−1
b = 20.5078 (14) ÅT = 173 K
c = 8.6339 (6) Å0.15 × 0.13 × 0.11 mm
β = 100.835 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		4028 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3317 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.971Rint = 0.029
16571 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å−3
4028 reflectionsΔρmin = −0.28 e Å−3
209 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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC15H15ClF3N3O
Mr345.75
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)9.2815 (6), 20.5078 (14), 8.6339 (6)
β (°) 100.835 (1)
V (Å3)1614.11 (19)
Z4
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.15 × 0.13 × 0.11
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.960, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections		16571, 4028, 3317
Rint0.029
(sin θ/λ)max (Å−1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.096, 1.03
No. of reflections4028
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.28

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

Hydrogen-bond geometry (Å, º) top
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.
 

Acknowledgements

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).

References

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 citationİnam, R., Gülerman, E. Z. & Sarigül, T. (2006). Anal. Chim. Acta, 579, 117–123.  Web of Science PubMed Google Scholar
 First citationLong, S., Muthusamy, V., Willis, P. G., Parkin, S. & Cammers, A. (2008). Beilstein J. Org. Chem. 4, No. 23.  Google Scholar
 First citationNakata, A., Hashimoto, S., Ikura, K. & Katsuura, K. (1991). J. Pestic. Sci. 16, 301–313.  CrossRef CAS 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2954
https://doi.org/10.1107/S1600536810042376
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