Methyl 4-(4-methyl­benzamido)-2-sulfamoylbenzoate

Mei-Yi Wang

doi:10.1107/S160053680803599X

. 2008 Nov 8;64(Pt 12):o2296. doi: 10.1107/S160053680803599X

Methyl 4-(4-methylbenzamido)-2-sulfamoylbenzoate

Mei-Yi Wang ^a,^*

PMCID: PMC2959991 PMID: 21581274

Abstract

The title compound, C₁₆H₁₆N₂O₅S, is a potent new fungicide. There are two molecules in the asymmetric unit which are linked by C—H⋯π interactions, forming a dimer. The two phenyl rings in each molecules are almost coplanar, with C—N—C—C torsion angles of 177.6 (2) and −172.5 (2)°. There are intermolecular and intramolecular N—H⋯O hydrogen bonds in the crystal structure.

Related literature

For the preparation and properties of substituted amides, see: Gong et al. (2008 ▶); Liu et al. (2007a ▶,b ▶); Wang et al. (2008 ▶). graphic file with name e-64-o2296-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O₅S
M _r = 348.37
Triclinic,
a = 9.1968 (16) Å
b = 11.078 (2) Å
c = 15.914 (3) Å
α = 75.894 (3)°
β = 87.124 (3)°
γ = 84.123 (3)°
V = 1563.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 294 (2) K
0.24 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.945, T _max = 0.968
8144 measured reflections
5479 independent reflections
3677 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.120
S = 1.01
5479 reflections
461 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks 070704Bc, I. DOI: 10.1107/S160053680803599X/bq2101sup1.cif

e-64-o2296-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803599X/bq2101Isup2.hkl

e-64-o2296-Isup2.hkl^{(268.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O7ⁱ	0.890 (10)	2.414 (15)	3.256 (3)	158 (2)
N2—H2A⋯O8ⁱⁱ	0.888 (10)	2.166 (12)	2.993 (3)	155 (2)
N3—H3A⋯O8ⁱⁱⁱ	0.889 (10)	2.59 (2)	3.254 (3)	132 (2)
N4—H4A⋯O1ⁱⁱⁱ	0.886 (10)	2.088 (11)	2.958 (3)	168 (3)
N2—H2B⋯O4	0.892 (10)	2.149 (18)	2.905 (3)	142 (2)
N4—H4B⋯O9	0.888 (10)	2.10 (2)	2.789 (3)	134 (2)
N4—H4B⋯O6^iv	0.888 (10)	2.59 (2)	3.298 (3)	137 (2)
C7—H7A⋯Cg1ⁱⁱ	0.96	2.87	3.7491	148 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C17--C22 ring.

supplementary crystallographic information

Comment

Amide derivative as a kind of highly bioactive compound has been studied broadly for many years. Whereas numerous references to the preparations and properties of a large variety of substituted amides exist in the literature (Liu et al., 2007a). These compounds had long been used in agriculture (Liu et al., 2007b) and medicine (Gong et al.,2008). In view of these facts and in continuation of our interest in the agriculture, we attempted to synthesize a series of amide derivatives, some of which have comparatively high fungicidal activity.

The molecular structure of title compound is showing in Fig.1. The X-ray analysis reveals that the benzene ring is planar. The carboxamide moiety is coplanar with the benzene ring [dihedral angle -1.5 (4)°]. The crystal structure is stabilized by the formation of inversion related dimers linked by C-H···π interactions (Table 1, Fig. 2).

Experimental

The title compound was prepared according to the similar reported procedure (Wang, et al., 2008). Dropwised 4-methylbenzoyl chloride (7.5 mmol) to methyl 4-amino-2-sulfamoylbenzoate (7.50 mmol) in THF (20 ml) solution, then refluxed for 4 h. Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from a mixture of ethyl acetate and petroleum ether.