Crystal structure of mandipropamid

Hyunjin Park; Jineun Kim; Gihaeng Kang; Tae Ho Kim

doi:10.1107/S2056989015016643

. 2015 Sep 12;71(Pt 10):o727–o728. doi: 10.1107/S2056989015016643

Crystal structure of mandipropamid

Hyunjin Park ^a, Jineun Kim ^a,^*, Gihaeng Kang ^a, Tae Ho Kim ^a,^*

PMCID: PMC4647438 PMID: 26594445

Abstract

In the title compound, C₂₃H₂₂ClNO₄ (systematic name: (RS)-2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-ynyloxy)acetamide), an amide fungicide, the dihedral angle between the chlorobenzene and benzene rings is 65.36 (6)°. In the crystal, N—H⋯O hydrogen bonds lead to zigzag supramolecular chains along the c axis (glide symmetry). These are connected into layers by C—H⋯O and C—H⋯π interactions; the layers stack along the a axis with no specific intermolecular interactions between them.

Keywords: crystal structure, conformation, hydrogen bonding, C—H⋯π interactions, amide fungicide

Related literature

For information on the fungicidal properties of the title compound, see: Zhang et al. (2014 ▸). For a related crystal structure, see: Davis & Healy (2008 ▸). graphic file with name e-71-0o727-scheme1.jpg

Experimental

Crystal data

C₂₃H₂₂ClNO₄
M _r = 411.86
Monoclinic,
a = 26.3733 (17) Å
b = 9.4740 (6) Å
c = 8.4882 (5) Å
β = 91.013 (3)°
V = 2120.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.22 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T _min = 0.722, T _max = 0.746
36727 measured reflections
4885 independent reflections
3686 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.131
S = 1.04
4885 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); 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 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015016643/tk5382sup1.cif

e-71-0o727-sup1.cif^{(1.1MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016643/tk5382Isup2.hkl

e-71-0o727-Isup2.hkl^{(267.9KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015016643/tk5382Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989015016643/tk5382fig1.tif

The molecular structure 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.^{(1.1MB, tif)}

b . DOI: 10.1107/S2056989015016643/tk5382fig2.tif

Crystal packing viewed along the b axis. The hydrogen bonds are shown as dashed lines.

CCDC reference: 1422569

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

Table 1. Hydrogen-bond geometry (, ).

Cg2 is the centroid of the C14C19 ring.

DHA	DH	HA	D A	DHA
N1H1NO2ⁱ	0.88	2.04	2.850(2)	152
C10H10O2ⁱⁱ	0.95	2.35	3.218(3)	152
C12H12AO1ⁱⁱⁱ	0.99	2.53	3.232(3)	128
C20H20C Cg2^iv	0.98	2.84	3.709(3)	148

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

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 (grnat No. 2014R1A1A4A01009105).

supplementary crystallographic information

S1. Comment

Mandipropamid [systematic name: (RS)-2-(4-chlorophenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-2-ynyloxy)acetamide] is a the amide fungicide that is used on potato, tomato, pepper, grape, watermelon, and litchi. (Zhang et al., 2014). The dihedral angle between the chlorobenzene and the benzene rings is 65.36 (6)°. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Davis & Healy, 2008).

In the crystal structure (Fig. 2), N–H···O and C–H···O hydrogen bonds and weak C–H···π interactions (Table 1) link adjacent molecules.

S2. Experimental

The title compound was purchased from Dr. Ehrenstorfer GmbH. Slow evaporation of its solution in CH₃CN gave single crystals suitable for X-ray analysis.