Crystal structure of fenpropathrin.

In the title compound [systematic name: cyano-(3-phen-oxy-phen-yl)methyl 2,2,3,3-tetra-methyl-cyclo-propane-carboxyl-ate], C22H23NO3, which is the pyrethroid insecticide fenpropathrin, the dihedral angle between the cyclo-propane ring plane and the carboxyl-ate group plane is 88.25 (11)°. The dihedral angle between the benzene and phenyl rings in the phen-oxy-benzyl group is 82.99 (4)°. In the crystal, C-H⋯N hydrogen bonds and weak C-H⋯π inter-actions link adjacent mol-ecules, forming loop chains along the b-axis direction.

Related literature

For information on the toxicity and insecticidal properties of the title compound, see: Wu et al. (1999 ▶); Hall & Nguyen (2010 ▶). For related crystal structures, see: Baert & Guelzim (1991 ▶); Yang et al. (2011 ▶).

Experimental

Crystal data

C22H23NO3

M = 349.41

Monoclinic,

a = 16.2578 (4) Å

b = 6.4799 (1) Å

c = 19.2475 (4) Å

β = 112.453 (1)°

V = 1873.99 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.50 × 0.20 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.998

30999 measured reflections

4279 independent reflections

3703 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.05

4279 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681402474X/hg5417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402474X/hg5417Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681402474X/hg5417Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S160053681402474X/hg5417fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S160053681402474X/hg5417fig2.tif

Crystal packing of the title compound with C—H⋯N hydrogen bonds and weak inter­molecular C—H⋯π inter­actions are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity, except H atoms of inter­actions.

CCDC reference: 1033607

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H23NO3	F(000) = 744
Mr = 349.41	Dx = 1.238 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9894 reflections
a = 16.2578 (4) Å	θ = 2.7–27.5°
b = 6.4799 (1) Å	µ = 0.08 mm−1
c = 19.2475 (4) Å	T = 173 K
β = 112.453 (1)°	Block, colourless
V = 1873.99 (7) Å3	0.50 × 0.20 × 0.03 mm
Z = 4

Bruker APEXII CCD diffractometer	4279 independent reflections
Radiation source: fine-focus sealed tube	3703 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.960, Tmax = 0.998	k = −8→8
30999 measured reflections	l = −24→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.044P)2 + 0.8901P] where P = (Fo2 + 2Fc2)/3
4279 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 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
O1	0.25941 (6)	0.19890 (17)	0.14087 (5)	0.0316 (2)
O2	0.11426 (5)	0.23376 (13)	0.12141 (5)	0.01977 (19)
O3	−0.11802 (6)	0.44803 (17)	0.26198 (5)	0.0300 (2)
N1	0.13768 (10)	0.73437 (19)	0.16331 (8)	0.0395 (3)
C1	0.27819 (9)	0.1836 (2)	−0.01169 (8)	0.0265 (3)
H1A	0.3141	0.1697	0.0421	0.040*
H1B	0.2674	0.3301	−0.0246	0.040*
H1C	0.3101	0.1220	−0.0407	0.040*
C2	0.12837 (9)	0.1063 (2)	−0.11154 (7)	0.0291 (3)
H2A	0.1523	0.0346	−0.1446	0.044*
H2B	0.1236	0.2541	−0.1231	0.044*
H2C	0.0693	0.0510	−0.1195	0.044*
C3	0.27228 (8)	−0.2137 (2)	0.06589 (7)	0.0239 (3)
H3A	0.3072	−0.2780	0.0400	0.036*
H3B	0.2576	−0.3175	0.0964	0.036*
H3C	0.3071	−0.1027	0.0985	0.036*
C4	0.12233 (9)	−0.2931 (2)	−0.03358 (8)	0.0271 (3)
H4A	0.0656	−0.2302	−0.0653	0.041*
H4B	0.1127	−0.3870	0.0025	0.041*
H4C	0.1467	−0.3705	−0.0651	0.041*
C5	0.19010 (8)	0.07394 (19)	−0.03022 (7)	0.0202 (2)
C6	0.18727 (8)	−0.12554 (19)	0.00844 (6)	0.0193 (2)
C7	0.14512 (8)	0.06898 (19)	0.02724 (7)	0.0203 (2)
H7	0.0786	0.0709	0.0040	0.024*
C8	0.18266 (8)	0.16961 (19)	0.10115 (7)	0.0203 (2)
C9	0.14081 (8)	0.33957 (19)	0.19286 (7)	0.0196 (2)
H9	0.2032	0.2990	0.2249	0.024*
C10	0.13830 (9)	0.5631 (2)	0.17713 (7)	0.0256 (3)
C11	0.07965 (8)	0.27541 (18)	0.23146 (6)	0.0181 (2)
C12	0.09429 (8)	0.08420 (19)	0.26710 (7)	0.0222 (3)
H12	0.1421	−0.0002	0.2672	0.027*
C13	0.03936 (9)	0.0168 (2)	0.30239 (7)	0.0277 (3)
H13	0.0498	−0.1136	0.3268	0.033*
C14	−0.03081 (9)	0.1380 (2)	0.30238 (7)	0.0279 (3)
H14	−0.0689	0.0914	0.3262	0.034*
C15	−0.04459 (8)	0.3284 (2)	0.26703 (7)	0.0227 (3)
C16	0.01002 (8)	0.39989 (19)	0.23177 (6)	0.0193 (2)
H16	0.0001	0.5315	0.2082	0.023*
C17	−0.11112 (8)	0.5735 (2)	0.32213 (7)	0.0226 (3)
C18	−0.03504 (8)	0.5875 (2)	0.38729 (7)	0.0227 (3)
H18	0.0160	0.5068	0.3932	0.027*
C19	−0.03484 (9)	0.7219 (2)	0.44377 (7)	0.0245 (3)
H19	0.0170	0.7332	0.4885	0.029*
C20	−0.10902 (9)	0.8391 (2)	0.43572 (7)	0.0263 (3)
H20	−0.1081	0.9307	0.4746	0.032*
C21	−0.18498 (9)	0.8219 (2)	0.37035 (8)	0.0278 (3)
H21	−0.2363	0.9013	0.3648	0.033*
C22	−0.18637 (8)	0.6899 (2)	0.31336 (7)	0.0269 (3)
H22	−0.2382	0.6789	0.2687	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0183 (4)	0.0463 (6)	0.0292 (5)	−0.0037 (4)	0.0081 (4)	−0.0172 (4)
O2	0.0177 (4)	0.0230 (4)	0.0189 (4)	0.0006 (3)	0.0073 (3)	−0.0055 (3)
O3	0.0168 (4)	0.0493 (6)	0.0232 (5)	0.0028 (4)	0.0069 (4)	−0.0090 (4)
N1	0.0650 (9)	0.0256 (6)	0.0429 (7)	−0.0082 (6)	0.0374 (7)	−0.0051 (5)
C1	0.0277 (7)	0.0259 (7)	0.0297 (7)	−0.0020 (5)	0.0152 (5)	−0.0014 (5)
C2	0.0331 (7)	0.0301 (7)	0.0209 (6)	0.0069 (6)	0.0069 (5)	0.0019 (5)
C3	0.0224 (6)	0.0271 (7)	0.0220 (6)	0.0045 (5)	0.0082 (5)	0.0016 (5)
C4	0.0294 (7)	0.0242 (7)	0.0274 (7)	−0.0033 (5)	0.0104 (5)	−0.0072 (5)
C5	0.0210 (6)	0.0215 (6)	0.0179 (6)	0.0025 (5)	0.0071 (5)	−0.0019 (5)
C6	0.0191 (5)	0.0206 (6)	0.0183 (5)	0.0009 (5)	0.0074 (4)	−0.0030 (5)
C7	0.0159 (5)	0.0233 (6)	0.0210 (6)	0.0009 (4)	0.0064 (4)	−0.0047 (5)
C8	0.0185 (6)	0.0213 (6)	0.0224 (6)	−0.0004 (5)	0.0093 (5)	−0.0031 (5)
C9	0.0195 (6)	0.0208 (6)	0.0189 (6)	−0.0014 (4)	0.0077 (5)	−0.0048 (5)
C10	0.0319 (7)	0.0261 (7)	0.0259 (6)	−0.0057 (5)	0.0190 (5)	−0.0069 (5)
C11	0.0182 (5)	0.0196 (6)	0.0157 (5)	−0.0024 (4)	0.0054 (4)	−0.0035 (4)
C12	0.0241 (6)	0.0191 (6)	0.0203 (6)	0.0001 (5)	0.0050 (5)	−0.0032 (5)
C13	0.0346 (7)	0.0217 (6)	0.0230 (6)	−0.0064 (5)	0.0067 (5)	0.0015 (5)
C14	0.0275 (7)	0.0355 (7)	0.0219 (6)	−0.0117 (6)	0.0107 (5)	−0.0017 (5)
C15	0.0162 (6)	0.0329 (7)	0.0180 (6)	−0.0017 (5)	0.0055 (4)	−0.0057 (5)
C16	0.0195 (6)	0.0213 (6)	0.0161 (5)	0.0001 (5)	0.0056 (4)	−0.0011 (4)
C17	0.0203 (6)	0.0295 (7)	0.0215 (6)	−0.0032 (5)	0.0118 (5)	−0.0003 (5)
C18	0.0193 (6)	0.0266 (6)	0.0233 (6)	−0.0004 (5)	0.0093 (5)	0.0027 (5)
C19	0.0257 (6)	0.0254 (6)	0.0215 (6)	−0.0037 (5)	0.0081 (5)	0.0017 (5)
C20	0.0308 (7)	0.0250 (7)	0.0275 (7)	−0.0035 (5)	0.0162 (5)	−0.0015 (5)
C21	0.0242 (6)	0.0306 (7)	0.0329 (7)	0.0021 (5)	0.0158 (6)	0.0015 (6)
C22	0.0188 (6)	0.0370 (7)	0.0255 (6)	−0.0004 (5)	0.0091 (5)	0.0008 (6)

O1—C8	1.2036 (15)	C7—H7	1.0000
O2—C8	1.3758 (14)	C9—C10	1.4773 (18)
O2—C9	1.4472 (14)	C9—C11	1.5093 (16)
O3—C17	1.3838 (15)	C9—H9	1.0000
O3—C15	1.3953 (15)	C11—C16	1.3919 (16)
N1—C10	1.1402 (18)	C11—C12	1.3919 (17)
C1—C5	1.5143 (17)	C12—C13	1.3833 (18)
C1—H1A	0.9800	C12—H12	0.9500
C1—H1B	0.9800	C13—C14	1.385 (2)
C1—H1C	0.9800	C13—H13	0.9500
C2—C5	1.5170 (17)	C14—C15	1.3852 (19)
C2—H2A	0.9800	C14—H14	0.9500
C2—H2B	0.9800	C15—C16	1.3869 (17)
C2—H2C	0.9800	C16—H16	0.9500
C3—C6	1.5139 (16)	C17—C18	1.3879 (17)
C3—H3A	0.9800	C17—C22	1.3916 (18)
C3—H3B	0.9800	C18—C19	1.3918 (18)
C3—H3C	0.9800	C18—H18	0.9500
C4—C6	1.5150 (17)	C19—C20	1.3831 (19)
C4—H4A	0.9800	C19—H19	0.9500
C4—H4B	0.9800	C20—C21	1.3905 (19)
C4—H4C	0.9800	C20—H20	0.9500
C5—C6	1.5009 (17)	C21—C22	1.3843 (19)
C5—C7	1.5416 (16)	C21—H21	0.9500
C6—C7	1.5423 (16)	C22—H22	0.9500
C7—C8	1.4691 (16)
C8—O2—C9	115.62 (9)	O1—C8—C7	129.17 (11)
C17—O3—C15	118.32 (9)	O2—C8—C7	109.07 (10)
C5—C1—H1A	109.5	O2—C9—C10	107.16 (10)
C5—C1—H1B	109.5	O2—C9—C11	108.90 (9)
H1A—C1—H1B	109.5	C10—C9—C11	113.52 (10)
C5—C1—H1C	109.5	O2—C9—H9	109.1
H1A—C1—H1C	109.5	C10—C9—H9	109.1
H1B—C1—H1C	109.5	C11—C9—H9	109.1
C5—C2—H2A	109.5	N1—C10—C9	177.69 (14)
C5—C2—H2B	109.5	C16—C11—C12	120.00 (11)
H2A—C2—H2B	109.5	C16—C11—C9	122.16 (11)
C5—C2—H2C	109.5	C12—C11—C9	117.84 (11)
H2A—C2—H2C	109.5	C13—C12—C11	120.14 (12)
H2B—C2—H2C	109.5	C13—C12—H12	119.9
C6—C3—H3A	109.5	C11—C12—H12	119.9
C6—C3—H3B	109.5	C12—C13—C14	120.46 (12)
H3A—C3—H3B	109.5	C12—C13—H13	119.8
C6—C3—H3C	109.5	C14—C13—H13	119.8
H3A—C3—H3C	109.5	C13—C14—C15	118.95 (12)
H3B—C3—H3C	109.5	C13—C14—H14	120.5
C6—C4—H4A	109.5	C15—C14—H14	120.5
C6—C4—H4B	109.5	C14—C15—C16	121.61 (12)
H4A—C4—H4B	109.5	C14—C15—O3	120.16 (11)
C6—C4—H4C	109.5	C16—C15—O3	118.11 (12)
H4A—C4—H4C	109.5	C15—C16—C11	118.83 (11)
H4B—C4—H4C	109.5	C15—C16—H16	120.6
C6—C5—C1	119.52 (10)	C11—C16—H16	120.6
C6—C5—C2	119.80 (11)	O3—C17—C18	123.63 (11)
C1—C5—C2	111.82 (11)	O3—C17—C22	115.50 (11)
C6—C5—C7	60.90 (8)	C18—C17—C22	120.87 (12)
C1—C5—C7	120.39 (10)	C17—C18—C19	118.82 (12)
C2—C5—C7	115.78 (10)	C17—C18—H18	120.6
C5—C6—C3	119.66 (10)	C19—C18—H18	120.6
C5—C6—C4	119.97 (10)	C20—C19—C18	120.95 (12)
C3—C6—C4	112.04 (11)	C20—C19—H19	119.5
C5—C6—C7	60.86 (8)	C18—C19—H19	119.5
C3—C6—C7	120.03 (10)	C19—C20—C21	119.50 (12)
C4—C6—C7	115.43 (10)	C19—C20—H20	120.3
C8—C7—C5	123.36 (10)	C21—C20—H20	120.3
C8—C7—C6	122.17 (10)	C22—C21—C20	120.44 (12)
C5—C7—C6	58.24 (7)	C22—C21—H21	119.8
C8—C7—H7	114.0	C20—C21—H21	119.8
C5—C7—H7	114.0	C21—C22—C17	119.42 (12)
C6—C7—H7	114.0	C21—C22—H22	120.3
O1—C8—O2	121.77 (11)	C17—C22—H22	120.3
C1—C5—C6—C3	0.51 (16)	O2—C9—C11—C16	−101.40 (12)
C2—C5—C6—C3	145.25 (12)	C10—C9—C11—C16	17.88 (16)
C7—C5—C6—C3	−109.99 (12)	O2—C9—C11—C12	78.15 (13)
C1—C5—C6—C4	−145.25 (11)	C10—C9—C11—C12	−162.58 (11)
C2—C5—C6—C4	−0.52 (17)	C16—C11—C12—C13	0.47 (17)
C7—C5—C6—C4	104.24 (12)	C9—C11—C12—C13	−179.08 (11)
C1—C5—C6—C7	110.50 (12)	C11—C12—C13—C14	0.28 (19)
C2—C5—C6—C7	−104.76 (12)	C12—C13—C14—C15	−0.53 (19)
C6—C5—C7—C8	110.01 (13)	C13—C14—C15—C16	0.04 (19)
C1—C5—C7—C8	0.90 (18)	C13—C14—C15—O3	175.92 (11)
C2—C5—C7—C8	−138.72 (12)	C17—O3—C15—C14	84.56 (15)
C1—C5—C7—C6	−109.10 (12)	C17—O3—C15—C16	−99.42 (13)
C2—C5—C7—C6	111.28 (12)	C14—C15—C16—C11	0.69 (18)
C5—C6—C7—C8	−112.01 (13)	O3—C15—C16—C11	−175.27 (10)
C3—C6—C7—C8	−2.61 (17)	C12—C11—C16—C15	−0.94 (17)
C4—C6—C7—C8	136.39 (12)	C9—C11—C16—C15	178.59 (10)
C3—C6—C7—C5	109.39 (12)	C15—O3—C17—C18	0.13 (18)
C4—C6—C7—C5	−111.60 (12)	C15—O3—C17—C22	179.54 (11)
C9—O2—C8—O1	0.52 (17)	O3—C17—C18—C19	178.79 (12)
C9—O2—C8—C7	−179.00 (10)	C22—C17—C18—C19	−0.60 (19)
C5—C7—C8—O1	−30.9 (2)	C17—C18—C19—C20	0.34 (19)
C6—C7—C8—O1	39.8 (2)	C18—C19—C20—C21	0.21 (19)
C5—C7—C8—O2	148.58 (11)	C19—C20—C21—C22	−0.5 (2)
C6—C7—C8—O2	−140.71 (11)	C20—C21—C22—C17	0.3 (2)
C8—O2—C9—C10	94.85 (12)	O3—C17—C22—C21	−179.15 (12)
C8—O2—C9—C11	−141.98 (10)	C18—C17—C22—C21	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1i	0.95	2.62	3.2715 (17)	126
C14—H14···Cg1i	0.95	2.87	3.6234 (15)	137

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C17C22 ring.

DHA	DH	HA	D A	DHA
C12H12N1i	0.95	2.62	3.2715(17)	126
C14H14Cg1i	0.95	2.87	3.6234(15)	137

Symmetry code: (i) .