Crystal structure of oryzalin

Gihaeng Kang; Jineun Kim; Youngeun Jeon; Tae Ho Kim

doi:10.1107/S205698901500955X

. 2015 May 30;71(Pt 6):o429. doi: 10.1107/S205698901500955X

Crystal structure of oryzalin

Gihaeng Kang ^a, Jineun Kim ^a,^*, Youngeun Jeon ^a, Tae Ho Kim ^a,^*

PMCID: PMC4459385 PMID: 26090208

Abstract

The title compound, C₁₂H₁₈N₄O₆S (systematic name: 4-dipropylamino-3,5-dinitrobenzenesulfonamide), is a sulfonamide with herbicidal properties marketed as oryzalin. The dihedral angles between the benzene ring and the mean planes of the nitro groups are 26.15 (11) and 54.80 (9)°. The propyl arms of the dipropylamino substituent lie on opposite sides of this ring plane. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds generate a three-dimensional network.

Keywords: crystal structure, oryzalin, sulfonamide, herbicidal properties, hydrogen bonding

Related literature

For information on the toxicity and herbicidal properties of the title compound, see: Naqvi & Leung (1983 ▸). For related crystal structures, see: O’Connell & Maslen (1967 ▸); Tremayne et al. (2002 ▸). graphic file with name e-71-0o429-scheme1.jpg

Experimental

Crystal data

C₁₂H₁₈N₄O₆S
M _r = 346.36
Triclinic,
a = 7.6057 (2) Å
b = 8.2463 (2) Å
c = 12.8657 (2) Å
α = 73.901 (1)°
β = 86.059 (1)°
γ = 83.549 (1)°
V = 769.77 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.49 × 0.17 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.888, T _max = 0.988
14199 measured reflections
3778 independent reflections
3506 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.090
S = 1.05
3778 reflections
218 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.42 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500955X/sj5462sup1.cif

e-71-0o429-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500955X/sj5462Isup2.hkl

e-71-0o429-Isup2.hkl^{(185.2KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supporting information file. DOI: 10.1107/S205698901500955X/sj5462Isup3.cml

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S205698901500955X/sj5462fig1.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.^{(1.5MB, tif)}

a . DOI: 10.1107/S205698901500955X/sj5462fig2.tif

Crystal packing viewed along the a axis. The intermolecular N—H⋯O and C—H⋯O hydrogen bonds are shown as dashed lines.

CCDC reference: 1401628

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H2NO6ⁱ	0.86(2)	2.529(19)	2.9956(15)	114.9(15)
N1H2NO2ⁱⁱ	0.86(2)	2.26(2)	3.0839(16)	160.5(17)
N1H1NO3ⁱⁱⁱ	0.81(2)	2.15(2)	2.9474(16)	170.0(19)
C2H2N1ⁱⁱ	0.95	2.74	3.6843(17)	171
C9H9AO4^iv	0.98	2.69	3.3192(18)	122
C10H10AO2^v	0.99	2.59	3.4033(15)	140
C12H12CO3^vi	0.98	2.71	3.249(2)	115
C12H12AO5^vii	0.98	2.61	3.492(2)	150

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

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 (No. 2012R1A1B3003337).

supplementary crystallographic information

S1. Comment

Oryzalin, C₁₂H₁₈N₄O₆S, is a sulfonamide herbicide for soybean and crop weeds (Naqvi & Leung, 1983). Its crystal structure is reported herein. In this compound (Scheme 1, Fig. 1), the dihedral angles between the central phenyl ring and the mean planes of two nitro groups are 26.15 (11) and 54.80 (9)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of similar compounds (O'Connell & Maslen, 1967; Tremayne et al., 2002).

In the crystal structure (Fig. 2), the crystal structure is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), resulting in a three-dimensional architechture.

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.