organic compounds
of pyriproxyfen
aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr
In the title compound {systematic name: 4-phenoxyphenyl (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 interactions [centroid–centroid separation = 3.8436 (13) Å] and C—H⋯π interactions link adjacent molecules, forming a three-dimensional network.
Keywords: crystal structure; pyriproxyfen; ether; juvenile hormone mimic; insecticide; π–π stacking.
CCDC reference: 1412612
1. 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).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
CCDC reference: 1412612
https://doi.org/10.1107/S2056989015013481/hb7462sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013481/hb7462Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013481/hb7462Isup3.cml
The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis in the form of colourless blocks.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 groups, d(C—H) = 0.98 Å, Uiso = 1.2Ueq(C) for CH3 groups, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.
Pyriproxyfen, [systematic name: 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether], is the juvenile hormone mimics and it has been used for the management of many insect pests including the house fly (Shah et al., 2015). However, until now its
has not been reported. In the title compound (Fig. 1), the dihedral angles between the planes of the central benzyl ring and the terminal pyridine ring and phenyl ring system are 78.09 (6) and 82.14 (8)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the of a similar compound (Ji et al., 2013; Kang et al., 2014).In the crystal (Fig. 2), weak intermolecular C—H···π interactions link adjacent molecules, forming a three-dimensional network (Table. 1). In addition, weak π–π interactions [Cg1···Cg1iv, 3.8436 (13) Å] are present (Cg1 is the centroid of the N1–C5 ring)[for symmetry codes: (iv),-x + 2,-y - 1,-z].
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).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).Fig. 1. 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. | |
Fig. 2. Crystal packing viewed along the a axis. The weak C—H···π and π–π interactions are shown as dashed lines. |
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 |
C20H19NO3 | V = 3306.65 (10) Å3 |
Mr = 321.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.0676 (2) Å | µ = 0.09 mm−1 |
b = 8.0279 (1) Å | T = 173 K |
c = 40.9129 (7) Å | 0.25 × 0.13 × 0.03 mm |
Bruker APEXII CCD diffractometer | 3238 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2515 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.997 | Rint = 0.065 |
52074 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.66 e Å−3 |
3238 reflections | Δρmin = −0.25 e Å−3 |
218 parameters |
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) |
Cg1 and Cg2 are the centroids of the N1/C4/C3/C2/C1/C5 and C15–C20 rings, respectively. |
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 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, y−1, z; (iii) −x+2, y+1/2, −z+1/2. |
Cg1 and Cg2 are the centroids of the N1/C4/C3/C2/C1/C5 and C15–C20 rings, respectively. |
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 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, y−1, z; (iii) −x+2, y+1/2, −z+1/2. |
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. 2015R1D1A4A01020317).
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Pyriproxyfen, [systematic name: 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether], is the juvenile hormone mimics and it has been used for the management of many insect pests including the house fly (Shah et al., 2015). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angles between the planes of the central benzyl ring and the terminal pyridine ring and phenyl ring system are 78.09 (6) and 82.14 (8)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the crystal structure of a similar compound (Ji et al., 2013; Kang et al., 2014).
In the crystal (Fig. 2), weak intermolecular C—H···π interactions link adjacent molecules, forming a three-dimensional network (Table. 1). In addition, weak π–π interactions [Cg1···Cg1iv, 3.8436 (13) Å] are present (Cg1 is the centroid of the N1–C5 ring)[for symmetry codes: (iv),-x + 2,-y - 1,-z].