Triflumizole.

In the title compound {systematic name: 4-chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethyl-idene]-2-(trifluoro-meth-yl)aniline}, C(15)H(15)ClF(3)N(3)O, the dihedral angle between the aniline and imidazole ring planes is 81.80 (4)°. In the crystal structure, weak inter-molecular C-H⋯X (X = N, O or F) hydrogen bonds and C-H⋯π inter-actions help to consolidate the packing.

Related literature

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

Crystal data

C15H15ClF3N3O

M = 345.75

Monoclinic,

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

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

C15H15ClF3N3O	F(000) = 712
Mr = 345.75	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5704 reflections
a = 9.2815 (6) Å	θ = 2.2–28.2°
b = 20.5078 (14) Å	µ = 0.27 mm−1
c = 8.6339 (6) Å	T = 173 K
β = 100.835 (1)°	Block, colourless
V = 1614.11 (19) Å3	0.15 × 0.13 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	3317 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.960, Tmax = 0.971	k = −27→26
16571 measured reflections	l = −11→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-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 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.28 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
Cl1	1.49537 (5)	0.75199 (2)	0.20992 (6)	0.05563 (14)
F1	0.88158 (9)	0.70250 (5)	0.32069 (12)	0.0519 (3)
F2	1.00525 (12)	0.66642 (5)	0.53792 (12)	0.0601 (3)
F3	1.03828 (12)	0.76378 (5)	0.46407 (13)	0.0573 (3)
N1	1.01160 (11)	0.57214 (5)	0.27790 (12)	0.0262 (2)
N2	0.80266 (11)	0.51277 (5)	0.19825 (12)	0.0253 (2)
N3	0.60502 (12)	0.44946 (6)	0.16697 (13)	0.0331 (3)
O1	0.81606 (10)	0.56645 (4)	−0.10396 (10)	0.0282 (2)
C1	1.01505 (16)	0.70258 (7)	0.41218 (17)	0.0362 (3)
C2	1.13094 (14)	0.67960 (6)	0.32611 (15)	0.0277 (3)
C3	1.24709 (15)	0.72066 (6)	0.31239 (16)	0.0331 (3)
H3	1.2553	0.7622	0.3617	0.040*
C4	1.34990 (15)	0.70066 (7)	0.22698 (17)	0.0340 (3)
C5	1.33924 (15)	0.64078 (7)	0.15219 (17)	0.0337 (3)
H5	1.4096	0.6280	0.0911	0.040*
C6	1.22451 (14)	0.59969 (6)	0.16759 (15)	0.0298 (3)
H6	1.2175	0.5582	0.1179	0.036*
C7	1.11926 (13)	0.61799 (6)	0.25445 (14)	0.0250 (2)
C8	0.89657 (13)	0.56432 (6)	0.17534 (14)	0.0244 (2)
C9	0.66245 (13)	0.50171 (6)	0.11769 (15)	0.0276 (3)
H9	0.6131	0.5290	0.0356	0.033*
C10	0.71276 (16)	0.42502 (7)	0.28583 (17)	0.0365 (3)
H10	0.7026	0.3867	0.3446	0.044*
C11	0.83378 (15)	0.46272 (7)	0.30736 (16)	0.0328 (3)
H11	0.9220	0.4563	0.3818	0.039*
C12	0.84433 (15)	0.60608 (6)	0.03188 (15)	0.0305 (3)
H12A	0.7538	0.6295	0.0439	0.037*
H12B	0.9202	0.6389	0.0211	0.037*
C13	0.74287 (15)	0.60238 (7)	−0.23828 (15)	0.0316 (3)
H13A	0.8080	0.6373	−0.2643	0.038*
H13B	0.6532	0.6230	−0.2142	0.038*
C14	0.70299 (16)	0.55717 (7)	−0.37587 (16)	0.0364 (3)
H14A	0.6424	0.5211	−0.3469	0.044*
H14B	0.7936	0.5381	−0.4018	0.044*
C15	0.61863 (18)	0.59207 (9)	−0.51998 (17)	0.0450 (4)
H15A	0.5288	0.6109	−0.4948	0.067*
H15B	0.5931	0.5609	−0.6069	0.067*
H15C	0.6796	0.6269	−0.5512	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0433 (2)	0.0460 (2)	0.0761 (3)	−0.02137 (18)	0.0072 (2)	0.0045 (2)
F1	0.0325 (5)	0.0604 (6)	0.0595 (6)	0.0106 (4)	0.0002 (4)	−0.0165 (5)
F2	0.0738 (7)	0.0644 (7)	0.0487 (6)	0.0213 (5)	0.0286 (5)	0.0098 (5)
F3	0.0570 (6)	0.0406 (5)	0.0737 (7)	0.0044 (4)	0.0108 (5)	−0.0297 (5)
N1	0.0267 (5)	0.0227 (5)	0.0269 (5)	−0.0006 (4)	−0.0003 (4)	−0.0005 (4)
N2	0.0244 (5)	0.0243 (5)	0.0253 (5)	−0.0015 (4)	−0.0002 (4)	0.0002 (4)
N3	0.0271 (5)	0.0376 (6)	0.0344 (6)	−0.0056 (5)	0.0048 (5)	−0.0006 (5)
O1	0.0319 (5)	0.0266 (4)	0.0238 (4)	0.0014 (4)	−0.0008 (3)	0.0011 (3)
C1	0.0377 (7)	0.0304 (7)	0.0379 (7)	0.0050 (6)	0.0007 (6)	−0.0067 (6)
C2	0.0290 (6)	0.0236 (6)	0.0273 (6)	0.0025 (5)	−0.0032 (5)	−0.0023 (5)
C3	0.0363 (7)	0.0219 (6)	0.0363 (7)	−0.0030 (5)	−0.0057 (6)	−0.0032 (5)
C4	0.0291 (6)	0.0288 (7)	0.0405 (7)	−0.0075 (5)	−0.0025 (5)	0.0042 (5)
C5	0.0297 (7)	0.0331 (7)	0.0376 (7)	0.0004 (5)	0.0046 (5)	0.0011 (5)
C6	0.0314 (6)	0.0233 (6)	0.0331 (6)	0.0000 (5)	0.0020 (5)	−0.0043 (5)
C7	0.0251 (6)	0.0210 (6)	0.0255 (6)	−0.0004 (4)	−0.0036 (4)	0.0001 (4)
C8	0.0269 (6)	0.0199 (5)	0.0251 (5)	0.0006 (4)	0.0015 (5)	−0.0016 (4)
C9	0.0218 (6)	0.0324 (6)	0.0274 (6)	−0.0008 (5)	0.0017 (5)	−0.0021 (5)
C10	0.0362 (7)	0.0334 (7)	0.0390 (7)	−0.0065 (6)	0.0047 (6)	0.0067 (6)
C11	0.0318 (7)	0.0303 (7)	0.0330 (7)	−0.0016 (5)	−0.0023 (5)	0.0068 (5)
C12	0.0368 (7)	0.0221 (6)	0.0282 (6)	−0.0036 (5)	−0.0049 (5)	0.0016 (5)
C13	0.0366 (7)	0.0303 (7)	0.0255 (6)	−0.0019 (5)	0.0000 (5)	0.0058 (5)
C14	0.0363 (7)	0.0427 (8)	0.0281 (6)	0.0066 (6)	0.0006 (5)	−0.0022 (6)
C15	0.0466 (9)	0.0602 (10)	0.0257 (7)	0.0056 (7)	0.0005 (6)	0.0017 (6)

Cl1—C4	1.7399 (14)	C5—H5	0.9500
F1—C1	1.3382 (17)	C6—C7	1.3903 (18)
F2—C1	1.3318 (18)	C6—H6	0.9500
F3—C1	1.3364 (16)	C8—C12	1.5089 (16)
N1—C8	1.2626 (15)	C9—H9	0.9500
N1—C7	1.4141 (16)	C10—C11	1.3473 (19)
N2—C9	1.3743 (16)	C10—H10	0.9500
N2—C11	1.3865 (16)	C11—H11	0.9500
N2—C8	1.4076 (16)	C12—H12A	0.9900
N3—C9	1.3033 (17)	C12—H12B	0.9900
N3—C10	1.3851 (18)	C13—C14	1.4976 (19)
O1—C12	1.4104 (15)	C13—H13A	0.9900
O1—C13	1.4328 (15)	C13—H13B	0.9900
C1—C2	1.4940 (19)	C14—C15	1.5189 (19)
C2—C3	1.3904 (19)	C14—H14A	0.9900
C2—C7	1.4022 (16)	C14—H14B	0.9900
C3—C4	1.374 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.382 (2)	C15—H15C	0.9800
C5—C6	1.3839 (18)
C8—N1—C7	120.74 (10)	N3—C9—N2	112.15 (11)
C9—N2—C11	106.15 (10)	N3—C9—H9	123.9
C9—N2—C8	127.26 (10)	N2—C9—H9	123.9
C11—N2—C8	126.59 (10)	C11—C10—N3	111.21 (12)
C9—N3—C10	104.87 (11)	C11—C10—H10	124.4
C12—O1—C13	111.25 (9)	N3—C10—H10	124.4
F2—C1—F3	106.33 (12)	C10—C11—N2	105.62 (12)
F2—C1—F1	106.44 (13)	C10—C11—H11	127.2
F3—C1—F1	105.80 (11)	N2—C11—H11	127.2
F2—C1—C2	113.31 (11)	O1—C12—C8	109.66 (10)
F3—C1—C2	112.15 (12)	O1—C12—H12A	109.7
F1—C1—C2	112.28 (11)	C8—C12—H12A	109.7
C3—C2—C7	120.33 (12)	O1—C12—H12B	109.7
C3—C2—C1	119.58 (11)	C8—C12—H12B	109.7
C7—C2—C1	120.04 (12)	H12A—C12—H12B	108.2
C4—C3—C2	119.53 (12)	O1—C13—C14	109.42 (11)
C4—C3—H3	120.2	O1—C13—H13A	109.8
C2—C3—H3	120.2	C14—C13—H13A	109.8
C3—C4—C5	121.34 (12)	O1—C13—H13B	109.8
C3—C4—Cl1	119.55 (11)	C14—C13—H13B	109.8
C5—C4—Cl1	119.10 (11)	H13A—C13—H13B	108.2
C4—C5—C6	119.00 (13)	C13—C14—C15	111.75 (12)
C4—C5—H5	120.5	C13—C14—H14A	109.3
C6—C5—H5	120.5	C15—C14—H14A	109.3
C5—C6—C7	121.26 (12)	C13—C14—H14B	109.3
C5—C6—H6	119.4	C15—C14—H14B	109.3
C7—C6—H6	119.4	H14A—C14—H14B	107.9
C6—C7—C2	118.52 (11)	C14—C15—H15A	109.5
C6—C7—N1	119.00 (11)	C14—C15—H15B	109.5
C2—C7—N1	122.29 (11)	H15A—C15—H15B	109.5
N1—C8—N2	117.46 (11)	C14—C15—H15C	109.5
N1—C8—C12	127.05 (11)	H15A—C15—H15C	109.5
N2—C8—C12	115.44 (10)	H15B—C15—H15C	109.5
F2—C1—C2—C3	−118.75 (14)	C8—N1—C7—C2	100.78 (14)
F3—C1—C2—C3	1.64 (18)	C7—N1—C8—N2	172.85 (11)
F1—C1—C2—C3	120.62 (14)	C7—N1—C8—C12	−9.71 (19)
F2—C1—C2—C7	63.75 (16)	C9—N2—C8—N1	168.55 (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—C4	0.52 (19)	C11—N2—C8—C12	170.74 (12)
C1—C2—C3—C4	−176.98 (13)	C10—N3—C9—N2	0.04 (15)
C2—C3—C4—C5	0.9 (2)	C11—N2—C9—N3	−0.19 (15)
C2—C3—C4—Cl1	−179.94 (10)	C8—N2—C9—N3	179.75 (11)
C3—C4—C5—C6	−1.7 (2)	C9—N3—C10—C11	0.13 (16)
Cl1—C4—C5—C6	179.17 (10)	N3—C10—C11—N2	−0.24 (16)
C4—C5—C6—C7	1.0 (2)	C9—N2—C11—C10	0.25 (15)
C5—C6—C7—C2	0.40 (19)	C8—N2—C11—C10	−179.68 (12)
C5—C6—C7—N1	−174.60 (11)	C13—O1—C12—C8	170.09 (10)
C3—C2—C7—C6	−1.17 (18)	N1—C8—C12—O1	127.19 (13)
C1—C2—C7—C6	176.31 (12)	N2—C8—C12—O1	−55.33 (14)
C3—C2—C7—N1	173.65 (11)	C12—O1—C13—C14	−174.92 (11)
C1—C2—C7—N1	−8.86 (18)	O1—C13—C14—C15	177.36 (12)
C8—N1—C7—C6	−84.42 (15)

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

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) ; (ii) ; (iii) ; (iv) .