Ethyl 2-{N-[N-(4-chloro-6-methoxy­pyrimidin-2-yl)carbamo­yl]sulfamo­yl}benzoate

Lu, C.; Li, F.-S.; Yu, D.-S.; Yao, W.; Liu, Y.-H.

doi:10.1107/S1600536808017029

Volume 64
Part 7
Page o1248
July 2008

Received 3 June 2008
Accepted 5 June 2008
Online 13 June 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R = 0.089
wR = 0.210
Data-to-parameter ratio = 15.3
Details

Ethyl 2-{N-[N-(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate

Chui Lu,^a Fang-Shi Li,^a ^* Da-Sheng Yu,^a Wei Yao ^a and Yin-Hong Liu ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
Correspondence e-mail: fangshi.li@njut.edu.cn

The asymmetric unit of the title compound, C₁₅H₁₅ClN₄O₆S, contains two independent molecules, in which the pyrimidine and benzene rings are oriented at dihedral angles of 75.21 (3) and 86.00 (3)°. Intramolecular N-HN and C-HO hydrogen bonds result in the formation of two five- and two six-membered rings. The six-membered rings have flattened-boat conformations, while the five-membered rings adopt envelope conformations. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules.

Related literature

For related literature, see: Zhao et al. (2006); Li & Liu (1995). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₅H₁₅ClN₄O₆S
M_r = 414.83
Triclinic, $[P \overline 1]$
a = 7.8210 (16) Å
b = 12.310 (3) Å
c = 20.200 (4) Å
= 94.97 (3)°
= 97.58 (3)°
= 93.76 (3)°
V = 1914.7 (7) Å³
Z = 4
Mo K radiation
= 0.35 mm^-1
T = 298 (2) K
0.40 × 0.30 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.873, T_max = 0.966
7430 measured reflections
6882 independent reflections
3809 reflections with I > 2(I)
R_int = 0.069
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.088
wR(F²) = 0.209
S = 1.07
6882 reflections
451 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.92 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN3	0.86	1.96	2.648 (6)	136
N2-H2AO5ⁱ	0.86	2.00	2.831 (8)	162
N5-H5BN7	0.86	1.96	2.651 (6)	136
N6-H6BO2ⁱⁱ	0.86	2.14	2.973 (7)	162
C8-H8AO4	0.93	2.43	2.821 (6)	105
C21-H21AO9	0.93	2.44	2.848 (8)	107
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2471 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Li, B. & Liu, C. L. (1995). Nongyao, 34, 36-37.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Zhao, J., Yi, G. X., He, S. P., Wang, B. M., Yu, C. X., Li, G., Zhai, Z. X., Li, Z. H. & Li, Q. X. (2006). J. Agric. Food Chem. 54, 4948-4953.

organic compounds