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Volume 69 
Part 8 
Page o1298  
August 2013  

Received 15 July 2013
Accepted 16 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.154
Data-to-parameter ratio = 16.0
Details
Open access

Thiophene-2-carbonyl azide

aDepartment of Chemistry & Biochemistry, Texas Tech University, Memorial Circle & Boston, Lubbock, TX 79409, USA
Correspondence e-mail: michael.findlater@ttu.edu

The title compound, C5H3N3OS, is almost planar (r.m.s. deviation for the ten non-H atoms = 0.018 Å) and forms an extended layer structure in the (100) plane, held together via hydrogen-bonding interactions between adjacent molecules. Of particular note is the occurrence of RC-H...N-=N+=NR interactions between an aromatic C-H group and an azide moiety which, in conjunction with a complementary C-H...O=C interaction, forms a nine-membered ring.

Related literature

For a previous preparation of the title compound, see: Binder et al. (1977[Binder, D., Habison, G. & Noe, C. R. (1977). Synthesis, pp. 255-256.]). For the synthesis of the starting material, 2-thiophenecarbonyl chloride, see: Kruse et al. (1989[Kruse, L. I., Ladd, D. L., Harrsch, P. B., McCabe, F. L., Mong, S.-M., Faucette, L. & Johnson, R. (1989). J. Med. Chem. 32, 409-417.]). For related structures, see: Arsenyan et al. (2008[Arsenyan, P., Petrenko, A. & Belyakov, S. (2008). Tetrahedron Lett. 49, 5255-5257.]); Elshaarawy & Janiak (2011[Elshaarawy, R. F. & Janiak, C. (2011). Z. Naturforsch. Teil B, 66, 1201-1208.]); Low et al. (2009[Low, J. N., Quesada, A., Santos, L. M. N. B. F., Schröder, B. & Gomes, L. R. (2009). J. Chem. Crystallogr. 39, 747-752.]).

[Scheme 1]

Experimental

Crystal data
  • C5H3N3OS

  • Mr = 153.16

  • Monoclinic, C 2/c

  • a = 12.668 (3) Å

  • b = 6.2153 (12) Å

  • c = 16.400 (3) Å

  • [beta] = 95.91 (3)°

  • V = 1284.4 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 153 K

  • 0.20 × 0.16 × 0.15 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO and 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.]) Tmin = 0.920, Tmax = 0.939

  • 2728 measured reflections

  • 1459 independent reflections

  • 1152 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.154

  • S = 1.13

  • 1459 reflections

  • 91 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N1i 0.95 2.63 3.512 (4) 155
C3-H3...N3ii 0.95 2.66 3.396 (4) 135
C4-H4...O1ii 0.95 2.47 3.415 (4) 173
Symmetry codes: (i) x, y-1, z; (ii) [x, -y, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: COLLECT; data reduction: DENZO and 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.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). SHELX2013. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL, enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5242 ).


Acknowledgements

The authors gratefully acknowledge the Robert A. Welch Foundation for their support of GCH via the Welch Summer Scholars Program, and Texas Tech University for start-up funds.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Arsenyan, P., Petrenko, A. & Belyakov, S. (2008). Tetrahedron Lett. 49, 5255-5257.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Binder, D., Habison, G. & Noe, C. R. (1977). Synthesis, pp. 255-256.  [CrossRef]
Elshaarawy, R. F. & Janiak, C. (2011). Z. Naturforsch. Teil B, 66, 1201-1208.
Kruse, L. I., Ladd, D. L., Harrsch, P. B., McCabe, F. L., Mong, S.-M., Faucette, L. & Johnson, R. (1989). J. Med. Chem. 32, 409-417.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Low, J. N., Quesada, A., Santos, L. M. N. B. F., Schröder, B. & Gomes, L. R. (2009). J. Chem. Crystallogr. 39, 747-752.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nonius (1998). 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] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2013). SHELX2013. University of Göttingen, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1298  [ doi:10.1107/S1600536813019740 ]

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