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

Wang, M.-Y.

doi:10.1107/S160053680803599X

Volume 64
Part 12
Page o2296
December 2008

Received 16 October 2008
Accepted 3 November 2008
Online 8 November 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R = 0.042
wR = 0.120
Data-to-parameter ratio = 11.9
Details

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

Mei-Yi Wang ^a ^*

^aCollege of Chemistry and Chemical Engineering, The North University for Ethnics, Yinchuan, 750021, People's Republic of China
Correspondence e-mail: nkulxh@gmail.com

The title compound, C₁₆H₁₆N₂O₅S, is a potent new fungicide. There are two molecules in the asymmetric unit which are linked by C-H [pi] 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-HO 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).

Experimental

Crystal data

C₁₆H₁₆N₂O₅S
M_r = 348.37
Triclinic, $[P \overline 1]$
a = 9.1968 (16) Å
b = 11.078 (2) Å
c = 15.914 (3) Å
= 75.894 (3)°
= 87.124 (3)°
= 84.123 (3)°
V = 1563.7 (5) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.120
S = 1.01
5479 reflections
461 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO7ⁱ	0.890 (10)	2.414 (15)	3.256 (3)	158 (2)
N2-H2AO8ⁱⁱ	0.888 (10)	2.166 (12)	2.993 (3)	155 (2)
N3-H3AO8ⁱⁱⁱ	0.889 (10)	2.59 (2)	3.254 (3)	132 (2)
N4-H4AO1ⁱⁱⁱ	0.886 (10)	2.088 (11)	2.958 (3)	168 (3)
N2-H2BO4	0.892 (10)	2.149 (18)	2.905 (3)	142 (2)
N4-H4BO9	0.888 (10)	2.10 (2)	2.789 (3)	134 (2)
N4-H4BO6^iv	0.888 (10)	2.59 (2)	3.298 (3)	137 (2)
C7-H7ACg1ⁱⁱ	0.96	2.87	3.7491	148 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+2, -z+2; (iv) -x+2, -y+2, -z+2. Cg1 is the centroid of the C17--C22 ring.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2101 ).

References

Bruker. (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Gong, Y., Barbay, J. K., Buntinx, M., Li, J., Van Wauweb, J., Claes, C., Van Lommen, G., Hornby, P. J. & He, W. (2008). Bioorg. Med. Chem. Lett. 18, 3852-3855.
Liu, X. H., Chen, P. Q., He, F. Q., Wang, S. H., Song, H. B. & Li, Z. M. (2007a). Struct. Chem. 18, 563-568.
Liu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007b). Bioorg. Med. Chem. Lett. 17, 3784-3788.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, M. Y., Guo, W. C., Lan, F., Li, Y. H. & Li, Z. M. (2008). Chin. J. Org. Chem. 287, 649-656.

organic compounds