4-Nitro­phenyl N-(2-sulfamoylphen­yl)carbamate

Yu, W.; Li, C.

doi:10.1107/S1600536813003310

Volume 69
Part 3
Page o355
March 2013

Received 24 January 2013
Accepted 31 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 14.7
Details

4-Nitrophenyl N-(2-sulfamoylphenyl)carbamate

Wenying Yu ^a and Chenglong Li ^a ^*

^aDivision of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA
Correspondence e-mail: li.728@osu.edu

In the title molecule, C₁₃H₁₁N₃O₆S, the dihedral angle between the benzene rings is 35.52 (8)°. An intramolecular N-HO hydrogen bond forms an S(6) ring. In the crystal, molecules are linked via N-HO hydrogen bonds into chains along [101] incorporating R₂²(8) and R₂²(16) rings.

Related literature

For the synthesis, see: Mallakpour & Rafiee (2007). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₁₁N₃O₆S
M_r = 337.31
Triclinic, $[P \overline 1]$
a = 8.2730 (2) Å
b = 8.4881 (2) Å
c = 10.4288 (2) Å
= 95.178 (1)°
= 103.507 (1)°
= 94.109 (1)°
V = 705.91 (3) Å³
Z = 2
Mo K radiation
= 0.27 mm^-1
T = 180 K
0.27 × 0.27 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
21157 measured reflections
3227 independent reflections
2473 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.098
S = 1.05
3227 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O3	0.802 (19)	2.02 (2)	2.6962 (18)	142.4 (18)
N2-H1N2O1ⁱ	0.83 (2)	2.15 (2)	2.975 (2)	175.1 (19)
N2-H2N2O4ⁱⁱ	0.89 (2)	2.10 (2)	2.967 (2)	165 (2)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+1.

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5580 ).

Acknowledgements

We are grateful to Dr Sihui Long for providing the help with the crystallization and also in editing this paper. We are grateful to Dr Judith Ann Gallucci for the X-ray crystallographic experiments.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Mallakpour, L. & Rafiee, Z. (2007). Synth. Commun. 37, 1927-1934.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds