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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 [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 14.7
Details
Open access

4-Nitrophenyl N-(2-sulfamoylphenyl)carbamate

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-H...O hydrogen bond forms an S(6) ring. In the crystal, molecules are linked via N-H...O hydrogen bonds into chains along [101] incorporating R22(8) and R22(16) rings.

Related literature

For the synthesis, see: Mallakpour & Rafiee (2007[Mallakpour, L. & Rafiee, Z. (2007). Synth. Commun. 37, 1927-1934.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N3O6S

  • Mr = 337.31

  • Triclinic, [P \overline 1]

  • a = 8.2730 (2) Å

  • b = 8.4881 (2) Å

  • c = 10.4288 (2) Å

  • [alpha] = 95.178 (1)°

  • [beta] = 103.507 (1)°

  • [gamma] = 94.109 (1)°

  • V = 705.91 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O3 0.802 (19) 2.02 (2) 2.6962 (18) 142.4 (18)
N2-H1N2...O1i 0.83 (2) 2.15 (2) 2.975 (2) 175.1 (19)
N2-H2N2...O4ii 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[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mallakpour, L. & Rafiee, Z. (2007). Synth. Commun. 37, 1927-1934.  [ISI] [CrossRef] [ChemPort]
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.  [CrossRef] [details]


Acta Cryst (2013). E69, o355  [ doi:10.1107/S1600536813003310 ]

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