data reports Monoclinic, C2=c ˚ a = 25.6913 (13) A ˚ b = 10.0220 (4) A ˚ c = 14.6417 (6) A  = 93.439 (4) ˚3 V = 3763.1 (3) A

ISSN 1600-5368

Z=8 Mo K radiation  = 0.37 mm1 T = 173 K 0.50  0.42  0.34 mm

2.2. Data collection

Crystal structure of difenoconazole Seonghwa Cho, Gihaeng Kang, Sangjin Lee and Tae Ho Kim* Department of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea. *Correspondence e-mail: [email protected] Received 9 October 2014; accepted 13 October 2014

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.837, Tmax = 0.885

28161 measured reflections 3694 independent reflections 3251 reflections with I > 2(I) Rint = 0.040

2.3. Refinement R[F 2 > 2(F 2)] = 0.059 wR(F 2) = 0.160 S = 1.06 3694 reflections

254 parameters H-atom parameters constrained ˚ 3 max = 1.08 e A ˚ 3 min = 0.82 e A

Edited by P. C. Healy, Griffith University, Australia

In the title compound difenoconazole [systematic name: 1-({2[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan2-yl}methyl)-1H-1,2,4-triazole], C19H17Cl2N3O3, the dihedral angle between the planes of the 4-chlorophenyl and 2chlorophenyl rings is 79.34 (9) , while the dihedral angle between the planes of the triazole ring and the dioxolanyl group is 59.45 (19) . In the crystal, pairs of C—H  N hydrogen bonds link adjacent molecules, forming dimers with R22(6) loops. In addition, the dimers are linked by C—H  O hydrogen bonds, resulting in a three-dimensional architecture. Disorder was modeled for one C atom of the dioxolanyl group over two sets of sites with an occupancy ratio of 0.566 (17):0.434 (17). Keywords: crystal structure; difenoconazole; triazole fungicide; hydrogen bonds.

Table 1 ˚ ,  ). Hydrogen-bond geometry (A D—H  A i

C6—H6  O3 C12—H12  O2ii C17—H17A  O1iii C18—H18  N3iv

D—H

H  A

D  A

D—H  A

0.95 0.95 0.99 0.95

2.48 2.40 2.58 2.57

3.314 (3) 3.226 (3) 3.378 (3) 3.323 (4)

146 145 138 136

Symmetry codes: (i) x þ 1; y; z; (ii) x þ 1; y; z þ 12; (iii) x þ 1; y þ 1; z; (iv) x þ 12; y þ 12; z.

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.

Acknowledgements

CCDC reference: 1028719

1. Related literature For information on the toxicity and fungicidal properties of the title compound, see: Dong et al. (2013); Mu et al. (2013). For a related crystal structure, see: Jeon et al. (2013).

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. 2012R1A1B3003337). Supporting information for this paper is available from the IUCr electronic archives (Reference: HG5412).

References Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Dong, F., Li, J., Chankvetadze, B., Cheng, Y., Xu, J., Liu, X., Li, Y., Chen, X., Bertucci, C., Tedesco, D., Zanasi, R. & Zheng, Y. (2013). Environ. Sci. Technol. 47, 3386–3394. Jeon, Y., Kim, J., Cho, S. & Kim, T. H. (2013). Acta Cryst. E69, o1206. Mu, X., Pang, S., Sun, X., Gao, J., Chen, J., Chen, X., Li, X. & Wang, C. (2013). Environ. Pollut. 175, 147–157. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

2. Experimental 2.1. Crystal data C19H17Cl2N3O3

Mr = 406.26

Acta Cryst. (2014). E70, o1173

doi:10.1107/S1600536814022429

Cho et al.

o1173

supporting information

supporting information Acta Cryst. (2014). E70, o1173

[doi:10.1107/S1600536814022429]

Crystal structure of difenoconazole Seonghwa Cho, Gihaeng Kang, Sangjin Lee and Tae Ho Kim S1. Comment Difenoconazole, C19H17Cl2N3O3, is a member of the triazoles group of fungicides and it has been used for the control of fungal diseases on fruits, vegetables, cereals, and other field crops (Dong et al., 2013; Mu et al., 2013). The structure of this compound is reported herein. In this compound (Fig. 1), the dihedral angle between the 4-chlorophenyl ring and the 2-chlorophenyl ring is 79.34 (9)°, while the dihedral angle between the triazole ring and dioxolanyl group plane is 59.45 (19)°. Disorder was modeled for one C atom (C15) of the dioxolanyl group group over two sets of sites with an occupancy ratio of 0.566 (17):0.434 (17). All bond lengths and bond angles are normal and comparable to those observed in the crystal structure of a similar compound (Jeon et al., 2013). In the crystal lattice (Fig. 2, Table 1), two C18—H18···N3 hydrogen bonds link adjacent molecules, forming dimers with R22(6) loops. In addition, the dimers linked by C6—H6···O3, C12—H12···O2, and C17—H17A···O1 hydrogen bonds, resulting in a three-dimensional architecture. S2. Experimental 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. S3. Refinement During refinement, the C15 atom of the dioxolanyl group was disordered and was refined using a split model. The corresponding site-occupation factors were refined so that their sum was unity [0.566 (17) and 0.434 (17)]. All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H, and d(C —H) = 1.00 Å, Uiso = 1.5Ueq(C) for Csp3—H.

Acta Cryst. (2014). E70, o1173

sup-1

supporting information

Figure 1 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. Only atoms of the major disorder components are shown.

Figure 2 Crystal packing of the title compound with C—H···N and C—H···O hydrogen bonds are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity, except H atoms of hydrogen bonds. Only atoms of the major disorder components are shown. 1-({2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole Crystal data C19H17Cl2N3O3 Mr = 406.26 Monoclinic, C2/c Hall symbol: -C 2yc a = 25.6913 (13) Å b = 10.0220 (4) Å c = 14.6417 (6) Å β = 93.439 (4)°

Acta Cryst. (2014). E70, o1173

V = 3763.1 (3) Å3 Z=8 F(000) = 1680 Dx = 1.434 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 9891 reflections θ = 2.2–27.5° µ = 0.37 mm−1

sup-2

supporting information T = 173 K Block, colourless

0.50 × 0.42 × 0.34 mm

Data collection Bruker APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.837, Tmax = 0.885

28161 measured reflections 3694 independent reflections 3251 reflections with I > 2σ(I) Rint = 0.040 θmax = 26.0°, θmin = 1.6° h = −31→31 k = −12→11 l = −16→18

Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.059 wR(F2) = 0.160 S = 1.06 3694 reflections 254 parameters 0 restraints Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0826P)2 + 11.4923P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001 Δρmax = 1.08 e Å−3 Δρmin = −0.82 e Å−3

Special details 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)

Cl1 Cl2 O1 O2 O3 N1 N2 N3 C1 C2 C3 H3 C4 C5

x

y

z

Uiso*/Ueq

0.42744 (2) 0.82170 (3) 0.62242 (7) 0.39803 (7) 0.44578 (7) 0.35985 (8) 0.35747 (10) 0.27774 (9) 0.48411 (10) 0.48477 (10) 0.53104 (10) 0.5305 0.57807 (10) 0.57897 (10)

0.49115 (6) 0.20023 (10) 0.48045 (19) 0.19880 (19) 0.04892 (18) 0.1646 (2) 0.0522 (3) 0.1059 (2) 0.2656 (3) 0.4006 (2) 0.4691 (3) 0.5600 0.4041 (3) 0.2708 (3)

0.12241 (5) 0.20260 (9) 0.13830 (15) 0.13311 (13) 0.05807 (14) −0.04986 (15) −0.10262 (18) −0.05524 (16) 0.08715 (18) 0.11281 (17) 0.13124 (17) 0.1496 0.12269 (18) 0.09724 (19)

0.0266 (2) 0.0669 (4) 0.0310 (5) 0.0278 (4) 0.0310 (5) 0.0238 (5) 0.0351 (6) 0.0311 (5) 0.0234 (5) 0.0217 (5) 0.0232 (5) 0.028* 0.0241 (5) 0.0280 (6)

Acta Cryst. (2014). E70, o1173

Occ. (

Crystal structure of difenoconazole.

In the title compound difenoconazole [systematic name: 1-({2-[2-chloro-4-(4-chloro-phen-oxy)phen-yl]-4-methyl-1,3-dioxolan-2-yl}meth-yl)-1H-1,2,4-tria...
315KB Sizes 2 Downloads 24 Views

Recommend Documents


Crystal structure of fenbuconazole.
In the title compound, C19H17ClN4 [systematic name: (RS)-4-(4-chloro-phen-yl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmeth-yl)butyro-nitrile], which is the conazole fungicide fenbuconazole, the dihedral angles between the planes of the central benzene and t

Crystal structure of triclopyr.
In the title compound {systematic name: 2-[(3,5,6-tri-chloro-pyridin-2-yl)-oxy]acetic acid}, the herbicide triclopyr, C7H4Cl3NO3, the asymmetric unit comprises two independent mol-ecules in which the dihedral angles between the mean plane of the carb

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 c

Crystal structure of cyproconazole.
The title compound [systematic name: 2-(4-chloro-phen-yl)-3-cyclo-propyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol], C15H18ClN3O, is a conazole fungicide. The asymmetric unit comprises two enanti-omeric pairs (mol-ecules A and B) in which the dihedral angl

Crystal structure of pymetrozine.
The title compound, C10H11N5O {systematic name: 6-methyl-4-[(E)-(pyridin-3-yl-methyl-idene)amino]-4,5-di-hydro-1,2,4-triazin-3(2H)-one}, C10H11N5O, is used as an anti-feedant in pest control. The asymmetric unit comprises two independent mol-ecules,

Crystal structure of metobromuron.
The title compound [systematic name: 3-(4-bromo-phen-yl)-1-meth-oxy-1-methyl-urea], C9H11BrN2O2, is a phenyl-urea herbicide. The dihedral angle between the plane of the urea group and that of the bromo-phenyl ring is 39.13 (10)°. In the crystal, N-H⋯

Crystal structure of fenclorim.
In the title compound, C10H6Cl2N2 (systematic name: 4,6-di-chloro-2-phenyl-pyrimidine), which is used commercially as the herbicide safener, fenclorim, the dihedral angle between the di-chloro-pyrimidyl and phenyl rings is 9.45 (10)°. In the crystal,

Crystal structure of Ba5In4Sb6.
The title compound, penta-barium tetra-indium hexa-anti-mony, was synthesized by an indium-flux reaction and its structure features layers composed of edge-sharing In2Sb6 units. The voids between the In4Sb6 layers are filled by Ba(2+) cations, which

Crystal structure of azimsulfuron.
The title compound {systematic name: 1-(4,6-di-meth-oxy-pyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetra-zol-5-yl)pyrazol-5-ylsulfon-yl]urea}, C13H16N10O5S, is a sulfonyl-urea herbicide. In this compound, the dihedral angles between the planes of the

Crystal structure of dimethomorph.
In the title compound, C21H22ClNO4 [systematic name: (E)-3-(4-chloro-phen-yl)-3-(3,4-di-meth-oxy-phen-yl)-1-(morpholin-4-yl)prop-2-en-1-one], which is the morpholine fungicide dimethomorph, the dihedral angles between the mean planes of the central c