Crystal structure of pyriproxyfen.

In the title compound {systematic name: 4-phen-oxy-phenyl (RS)-2-[(pyridin-2-yl)-oxy]propyl ether}, C20H19NO3, which is a juvenile hormone mimic and insecticide, the dihedral angles between the plane of the central benene ring and those of the pendant pyridine ring and phenyl ring are 78.09 (6) and 82.14 (8)°, respectively. The conformation of the O-C-C-O linkage is gauche [torsion angle = -75.0 (2)°]. In the crystal, weak aromatic π-π stacking inter-actions [centroid-centroid separation = 3.8436 (13) Å] and C-H⋯π inter-actions link adjacent mol-ecules, forming a three-dimensional network.

Related literature

For information on the insecticidal properties of the title compound, see: Shah et al. (2015 ▸). For related crystal structures, see: Ji et al. (2013 ▸); Kang et al. (2014 ▸).

Experimental

Crystal data

C20H19NO3

M = 321.36

Orthorhombic,

a = 10.0676 (2) Å

b = 8.0279 (1) Å

c = 40.9129 (7) Å

V = 3306.65 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.25 × 0.13 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.979, T max = 0.997

52074 measured reflections

3238 independent reflections

2515 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.148

S = 1.04

3238 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015013481/hb7462sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013481/hb7462Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013481/hb7462Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015013481/hb7462fig1.tif

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

Click here for additional data file.

a . DOI: 10.1107/S2056989015013481/hb7462fig2.tif

Crystal packing viewed along the a axis. The weak C—H⋯π and π–π inter­actions are shown as dashed lines.

CCDC reference: 1412612

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

C20H19NO3	Dx = 1.291 Mg m−3
Mr = 321.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7580 reflections
a = 10.0676 (2) Å	θ = 2.3–22.0°
b = 8.0279 (1) Å	µ = 0.09 mm−1
c = 40.9129 (7) Å	T = 173 K
V = 3306.65 (10) Å3	Block, colourless
Z = 8	0.25 × 0.13 × 0.03 mm
F(000) = 1360

Bruker APEXII CCD diffractometer	2515 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.065
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 26.0°, θmin = 2.0°
Tmin = 0.979, Tmax = 0.997	h = −12→12
52074 measured reflections	k = −9→9
3238 independent reflections	l = −50→50

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0576P)2 + 2.9207P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3238 reflections	Δρmax = 0.66 e Å−3
218 parameters	Δρmin = −0.25 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.

	x	y	z	Uiso*/Ueq
O1	0.93462 (16)	−0.1993 (2)	0.07340 (4)	0.0440 (4)
O2	0.97257 (17)	0.12811 (19)	0.10028 (4)	0.0407 (4)
O3	0.84983 (16)	0.6264 (2)	0.18833 (4)	0.0470 (4)
N1	0.9994 (2)	−0.2077 (3)	0.01922 (5)	0.0430 (5)
C1	0.8083 (2)	−0.3616 (3)	0.03714 (6)	0.0427 (6)
H1	0.7514	−0.3931	0.0546	0.051*
C2	0.7879 (2)	−0.4169 (3)	0.00560 (6)	0.0454 (6)
H2	0.7164	−0.4901	0.0008	0.054*
C3	0.8727 (2)	−0.3645 (3)	−0.01884 (6)	0.0446 (6)
H3	0.8595	−0.3993	−0.0408	0.054*
C4	0.9750 (2)	−0.2626 (3)	−0.01099 (6)	0.0443 (6)
H4	1.0329	−0.2280	−0.0280	0.053*
C5	0.9177 (2)	−0.2561 (3)	0.04197 (5)	0.0357 (5)
C6	1.0603 (2)	−0.1277 (3)	0.08188 (5)	0.0385 (5)
H6	1.0927	−0.0579	0.0633	0.046*
C7	1.1605 (3)	−0.2635 (3)	0.08878 (6)	0.0516 (7)
H7A	1.1273	−0.3353	0.1063	0.077*
H7B	1.2449	−0.2131	0.0955	0.077*
H7C	1.1743	−0.3300	0.0690	0.077*
C8	1.0369 (3)	−0.0192 (3)	0.11085 (6)	0.0413 (6)
H8A	0.9807	−0.0781	0.1270	0.050*
H8B	1.1225	0.0088	0.1214	0.050*
C9	0.9480 (2)	0.2473 (3)	0.12354 (5)	0.0328 (5)
C10	0.8926 (3)	0.3944 (3)	0.11212 (6)	0.0418 (6)
H10	0.8755	0.4079	0.0894	0.050*
C11	0.8624 (2)	0.5218 (3)	0.13372 (6)	0.0419 (6)
H11	0.8244	0.6227	0.1260	0.050*
C12	0.8880 (2)	0.5010 (3)	0.16646 (6)	0.0381 (5)
C13	0.9423 (2)	0.3563 (3)	0.17803 (6)	0.0405 (6)
H13	0.9588	0.3437	0.2008	0.049*
C14	0.9732 (2)	0.2277 (3)	0.15657 (5)	0.0389 (5)
H14	1.0114	0.1273	0.1645	0.047*
C15	0.9434 (2)	0.7403 (3)	0.19842 (5)	0.0335 (5)
C16	1.0758 (2)	0.7374 (3)	0.18908 (5)	0.0376 (5)
H16	1.1078	0.6548	0.1744	0.045*
C17	1.1612 (3)	0.8584 (3)	0.20167 (6)	0.0441 (6)
H17	1.2521	0.8581	0.1955	0.053*
C18	1.1157 (3)	0.9779 (3)	0.22293 (6)	0.0465 (6)
H18	1.1751	1.0585	0.2316	0.056*
C19	0.9830 (3)	0.9803 (3)	0.23162 (5)	0.0434 (6)
H19	0.9510	1.0640	0.2460	0.052*
C20	0.8970 (2)	0.8620 (3)	0.21951 (5)	0.0387 (5)
H20	0.8060	0.8639	0.2256	0.046*

	U11	U22	U33	U12	U13	U23
O1	0.0434 (10)	0.0497 (10)	0.0389 (9)	−0.0070 (8)	0.0040 (7)	−0.0049 (7)
O2	0.0592 (10)	0.0341 (8)	0.0290 (8)	0.0042 (8)	−0.0059 (7)	0.0004 (6)
O3	0.0366 (9)	0.0428 (10)	0.0618 (11)	−0.0025 (8)	0.0069 (8)	−0.0159 (8)
N1	0.0424 (11)	0.0441 (12)	0.0424 (11)	0.0004 (9)	0.0015 (9)	−0.0029 (9)
C1	0.0396 (13)	0.0426 (14)	0.0459 (14)	0.0053 (11)	0.0021 (11)	0.0098 (11)
C2	0.0387 (13)	0.0353 (13)	0.0622 (16)	−0.0019 (11)	−0.0161 (12)	0.0006 (12)
C3	0.0472 (14)	0.0498 (14)	0.0368 (13)	0.0126 (12)	−0.0118 (11)	−0.0084 (11)
C4	0.0430 (14)	0.0494 (15)	0.0404 (13)	0.0033 (12)	0.0011 (11)	0.0014 (11)
C5	0.0401 (12)	0.0340 (12)	0.0330 (11)	0.0096 (10)	−0.0075 (10)	−0.0037 (9)
C6	0.0378 (13)	0.0424 (13)	0.0353 (12)	−0.0025 (11)	−0.0014 (10)	−0.0053 (10)
C7	0.0529 (16)	0.0536 (16)	0.0484 (14)	0.0071 (13)	−0.0012 (12)	−0.0074 (12)
C8	0.0508 (14)	0.0360 (13)	0.0372 (12)	0.0029 (11)	−0.0045 (10)	−0.0006 (10)
C9	0.0363 (12)	0.0306 (11)	0.0314 (11)	−0.0030 (9)	−0.0030 (9)	−0.0007 (9)
C10	0.0506 (14)	0.0385 (13)	0.0362 (12)	−0.0009 (11)	−0.0043 (11)	0.0079 (10)
C11	0.0430 (14)	0.0335 (12)	0.0493 (14)	0.0031 (11)	−0.0012 (11)	0.0057 (11)
C12	0.0315 (11)	0.0365 (12)	0.0461 (13)	−0.0038 (10)	0.0016 (10)	−0.0065 (10)
C13	0.0429 (13)	0.0452 (14)	0.0334 (12)	0.0002 (11)	−0.0040 (10)	−0.0040 (10)
C14	0.0470 (14)	0.0355 (12)	0.0343 (12)	0.0029 (11)	−0.0064 (10)	0.0017 (10)
C15	0.0376 (12)	0.0306 (11)	0.0322 (11)	−0.0006 (10)	−0.0030 (9)	0.0020 (9)
C16	0.0398 (13)	0.0362 (12)	0.0368 (12)	0.0040 (10)	0.0008 (10)	0.0029 (10)
C17	0.0384 (13)	0.0463 (14)	0.0477 (14)	−0.0033 (11)	−0.0069 (11)	0.0093 (12)
C18	0.0561 (16)	0.0392 (13)	0.0440 (13)	−0.0040 (12)	−0.0170 (12)	0.0032 (11)
C19	0.0605 (16)	0.0382 (13)	0.0314 (12)	0.0032 (12)	−0.0073 (11)	−0.0018 (10)
C20	0.0436 (13)	0.0390 (12)	0.0335 (12)	0.0068 (11)	−0.0007 (10)	0.0010 (10)

O1—C5	1.375 (3)	C8—H8B	0.9900
O1—C6	1.432 (3)	C9—C14	1.384 (3)
O2—C9	1.372 (3)	C9—C10	1.387 (3)
O2—C8	1.416 (3)	C10—C11	1.386 (3)
O3—C15	1.376 (3)	C10—H10	0.9500
O3—C12	1.401 (3)	C11—C12	1.374 (3)
N1—C5	1.302 (3)	C11—H11	0.9500
N1—C4	1.335 (3)	C12—C13	1.368 (3)
C1—C2	1.380 (3)	C13—C14	1.391 (3)
C1—C5	1.404 (3)	C13—H13	0.9500
C1—H1	0.9500	C14—H14	0.9500
C2—C3	1.380 (4)	C15—C20	1.385 (3)
C2—H2	0.9500	C15—C16	1.387 (3)
C3—C4	1.354 (4)	C16—C17	1.395 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.373 (4)
C6—C8	1.490 (3)	C17—H17	0.9500
C6—C7	1.511 (3)	C18—C19	1.382 (4)
C6—H6	1.0000	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.377 (3)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—H20	0.9500
C8—H8A	0.9900
C5—O1—C6	117.96 (18)	O2—C9—C14	124.4 (2)
C9—O2—C8	116.94 (16)	O2—C9—C10	115.65 (19)
C15—O3—C12	118.77 (17)	C14—C9—C10	120.0 (2)
C5—N1—C4	116.5 (2)	C11—C10—C9	120.1 (2)
C2—C1—C5	116.3 (2)	C11—C10—H10	119.9
C2—C1—H1	121.9	C9—C10—H10	119.9
C5—C1—H1	121.9	C12—C11—C10	119.4 (2)
C1—C2—C3	119.1 (2)	C12—C11—H11	120.3
C1—C2—H2	120.4	C10—C11—H11	120.3
C3—C2—H2	120.4	C13—C12—C11	121.0 (2)
C4—C3—C2	118.9 (2)	C13—C12—O3	119.9 (2)
C4—C3—H3	120.6	C11—C12—O3	118.9 (2)
C2—C3—H3	120.6	C12—C13—C14	120.1 (2)
N1—C4—C3	124.0 (2)	C12—C13—H13	119.9
N1—C4—H4	118.0	C14—C13—H13	119.9
C3—C4—H4	118.0	C9—C14—C13	119.4 (2)
N1—C5—O1	119.5 (2)	C9—C14—H14	120.3
N1—C5—C1	125.1 (2)	C13—C14—H14	120.3
O1—C5—C1	115.4 (2)	O3—C15—C20	115.1 (2)
O1—C6—C8	106.72 (19)	O3—C15—C16	124.4 (2)
O1—C6—C7	110.2 (2)	C20—C15—C16	120.5 (2)
C8—C6—C7	112.2 (2)	C15—C16—C17	118.6 (2)
O1—C6—H6	109.2	C15—C16—H16	120.7
C8—C6—H6	109.2	C17—C16—H16	120.7
C7—C6—H6	109.2	C18—C17—C16	121.0 (2)
C6—C7—H7A	109.5	C18—C17—H17	119.5
C6—C7—H7B	109.5	C16—C17—H17	119.5
H7A—C7—H7B	109.5	C17—C18—C19	119.6 (2)
C6—C7—H7C	109.5	C17—C18—H18	120.2
H7A—C7—H7C	109.5	C19—C18—H18	120.2
H7B—C7—H7C	109.5	C20—C19—C18	120.4 (2)
O2—C8—C6	108.52 (18)	C20—C19—H19	119.8
O2—C8—H8A	110.0	C18—C19—H19	119.8
C6—C8—H8A	110.0	C19—C20—C15	119.9 (2)
O2—C8—H8B	110.0	C19—C20—H20	120.1
C6—C8—H8B	110.0	C15—C20—H20	120.1
H8A—C8—H8B	108.4
C5—C1—C2—C3	−1.1 (3)	C10—C11—C12—C13	−0.3 (4)
C1—C2—C3—C4	1.2 (4)	C10—C11—C12—O3	−176.2 (2)
C5—N1—C4—C3	−0.5 (4)	C15—O3—C12—C13	86.0 (3)
C2—C3—C4—N1	−0.4 (4)	C15—O3—C12—C11	−98.0 (3)
C4—N1—C5—O1	−177.7 (2)	C11—C12—C13—C14	0.4 (4)
C4—N1—C5—C1	0.7 (3)	O3—C12—C13—C14	176.3 (2)
C6—O1—C5—N1	−17.0 (3)	O2—C9—C14—C13	−179.0 (2)
C6—O1—C5—C1	164.4 (2)	C10—C9—C14—C13	0.2 (3)
C2—C1—C5—N1	0.1 (3)	C12—C13—C14—C9	−0.4 (4)
C2—C1—C5—O1	178.6 (2)	C12—O3—C15—C20	178.8 (2)
C5—O1—C6—C8	157.85 (19)	C12—O3—C15—C16	−1.8 (3)
C5—O1—C6—C7	−80.0 (2)	O3—C15—C16—C17	−178.6 (2)
C9—O2—C8—C6	−177.21 (19)	C20—C15—C16—C17	0.7 (3)
O1—C6—C8—O2	−75.0 (2)	C15—C16—C17—C18	0.1 (3)
C7—C6—C8—O2	164.1 (2)	C16—C17—C18—C19	−1.0 (4)
C8—O2—C9—C14	−4.7 (3)	C17—C18—C19—C20	1.1 (3)
C8—O2—C9—C10	176.0 (2)	C18—C19—C20—C15	−0.2 (3)
O2—C9—C10—C11	179.2 (2)	O3—C15—C20—C19	178.7 (2)
C14—C9—C10—C11	−0.1 (4)	C16—C15—C20—C19	−0.7 (3)
C9—C10—C11—C12	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1i	0.95	2.85	3.667 (3)	145
C14—H14···Cg2ii	0.95	2.86	3.733 (2)	152
C19—H19···Cg2iii	0.95	2.97	3.857 (2)	156

Table 1

CH interactions (, )

Cg1 and Cg2 are the centroids of the N1/C4/C3/C2/C1/C5 and C15C20 rings, respectively.

DHA	DH	HA	D A	DHA
C2H2Cg1i	0.95	2.85	3.667(3)	145
C14H14Cg2ii	0.95	2.86	3.733(2)	152
C19H19Cg2iii	0.95	2.97	3.857(2)	156

Symmetry codes: (i) ; (ii) ; (iii) .