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Volume 69 
Part 9 
Page o1413  
September 2013  

Received 26 July 2013
Accepted 6 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.078
Data-to-parameter ratio = 16.9
Details
Open access

tert-Butyl N-(thiophen-2-yl)carbamate

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

In the title compound, C9H13NO2S, the dihedral angle between the thiophene ring and the carbamate group is 15.79 (14)°. In the crystal structure, intramolecular C-H...O interactions in tandem with the tert-butyl groups render the packing of adjacent molecules in the [001] direction nearly perpendicular [the angle between adjacent thiophene rings is 74.83 (7)°]. An intermolecular N-H...O hydrogen bond gives rise to a chain extending along [001]. The crystal studied was found to be a racemic twin.

Related literature

For the synthesis of the title compound, see: Binder et al. (1977[Binder, D., Habison, G. & Noe, C. R. (1977). Synthesis, pp. 255-256.]); 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.]); Hsu et al. (2013[Hsu, G. C., Singer, L. M., Cordes, D. B. & Findlater, M. (2013). Acta Cryst. E69, o1298.]).

[Scheme 1]

Experimental

Crystal data
  • C9H13NO2S

  • Mr = 199.26

  • Orthorhombic, P c a 21

  • a = 11.732 (2) Å

  • b = 8.6513 (17) Å

  • c = 9.879 (2) Å

  • V = 1002.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 153 K

  • 0.20 × 0.10 × 0.08 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 = 0.944, Tmax = 0.977

  • 2112 measured reflections

  • 2112 independent reflections

  • 1816 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.078

  • S = 1.04

  • 2112 reflections

  • 125 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])

  • Absolute structure parameter: 0.53 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.90 (2) 2.04 (2) 2.920 (3) 165 (3)
C7-H7A...O1 0.98 2.33 2.938 (4) 119
C8-H8C...O1 0.98 2.55 3.109 (4) 116
Symmetry code: (i) [-x+{\script{1\over 2}}, 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: ZS2273 ).


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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Arsenyan, P., Petrenko, A. & Belyakov, S. (2008). Tetrahedron Lett. 49, 5255-5257.  [ISI] [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.
Hsu, G. C., Singer, L. M., Cordes, D. B. & Findlater, M. (2013). Acta Cryst. E69, o1298.  [CrossRef] [details]
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] [ISI]
Low, J. N., Quesada, A., Santos, L. M. N. B. F., Schröder, B. & Gomes, L. R. (2009). J. Chem. Crystallogr. 39, 747-752.  [ISI] [CSD] [CrossRef] [ChemPort]
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.
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1413  [ doi:10.1107/S160053681302196X ]

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