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Volume 68 
Part 9 
Page o2652  
September 2012  

Received 27 July 2012
Accepted 30 July 2012
Online 8 August 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.123
Data-to-parameter ratio = 33.7
Details
Open access

4-Nitro-1-[(trimethylsilyl)ethynyl]benzene: low-temperature polymorph at 100 K1

Jasmine N. Millican,a Frank R. Fronczeka* and Steve F. Watkinsa

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C11H13NO2Si, is a low-temperature form of the previously reported room-temperature structure [Garcia et al. (1998[Garcia, J. G., Asfaw, B., Rodriguez, A. & Fronczek, F. R. (1998). Acta Cryst. C54, 489-491.]). Acta Cryst. C54, 489-491]. At 298 K, the material crystallizes in the space group Pnma and occupies a crystallographic mirror plane, but at 100 K the space group changes to P212121, the volume decreases by 5% and the molecule distorts. The greatest molecular distortions from Cs symmetry are rotations of the trimethylsilyl and nitro groups by 10.56 (8) and 11.47 (9)°, respectively, to the benzene mean plane. At low temperature, the crystal also becomes an inversion twin, the refined ratio of the twin components being 0.35 (15):0.65 (15).

Related literature

For the synthesis of the title compound, see: Takahashi et al. (1980[Takahashi, S., Kuroyama, Y., Sonogashira, K. & Hagihara, N. (1980). Synthesis, 8, 627-630.]). For the crystal structure of the room temperature form of the title compound, see: Garcia et al. (1998[Garcia, J. G., Asfaw, B., Rodriguez, A. & Fronczek, F. R. (1998). Acta Cryst. C54, 489-491.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For Hooft analysis of Bijvoet pairs, see: Hooft et al. (2008[Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.]).

[Scheme 1]

Experimental

Crystal data

  • C11H13NO2Si

  • Mr = 219.31

  • Orthorhombic, P 21 21 21

  • a = 10.222 (2) Å

  • b = 7.128 (2) Å

  • c = 16.537 (4) Å

  • V = 1204.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 100 K

  • 0.20 × 0.15 × 0.12 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (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 = 0.966, Tmax = 0.979

  • 17805 measured reflections

  • 4690 independent reflections

  • 3538 reflections with I > 2[sigma](I)

  • Rint = 0.032
Refinement

  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.123

  • S = 1.02

  • 4690 reflections

  • 139 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1953 Bijvoet pairs

  • Flack parameter: 0.35 (15)

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: 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.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2491 ).

Acknowledgements

Purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ESH-TR-13, administered by the Louisiana Board of Regents.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Garcia, J. G., Asfaw, B., Rodriguez, A. & Fronczek, F. R. (1998). Acta Cryst. C54, 489-491.  [CrossRef] [details]
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.  [ISI] [CrossRef] [ChemPort] [details]
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]
Takahashi, S., Kuroyama, Y., Sonogashira, K. & Hagihara, N. (1980). Synthesis, 8, 627-630.  [CrossRef]

Acta Cryst (2012). E68, o2652  [ doi:10.1107/S1600536812034034 ]

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