electronic reprint Redetermination of 4-nitrostilbene

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Oct 29, 2008 - Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, ... Park, G., Jung, W. S. & Ra, C. S. (2004). Bull. .... l @ K37X39.
electronic reprint Acta Crystallographica Section E

Structure Reports Online ISSN 1600-5368

Editors: W.T. A. Harrison, J. Simpson and M. Weil

Redetermination of 4-nitrostilbene Rodolfo Moreno-Fuquen, Lina Aguirre and Alan R. Kennedy

Acta Cryst. (2008). E64, o2259

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ISSN 1600-5368

Volume 61 Part 11 November 2005

Acta Crystallographica Section E

Structure Reports Online Editors: W. Clegg and D. G. Watson

Inorganic compounds

Metal-organic compounds

Organic compounds

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*

Acta Crystallographica Section E: Structure Reports Online is the IUCr’s highly popular open-access structural journal. It provides a simple and easily accessible publication mechanism for the growing number of inorganic, metal-organic and organic crystal structure determinations. The electronic submission, validation, refereeing and publication facilities of the journal ensure very rapid and high-quality publication, whilst key indicators and validation reports provide measures of structural reliability. In 2007, the journal published over 5000 structures. The average publication time is less than one month.

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Crystallography Journals Online is available from journals.iucr.org Acta Cryst. (2008). E64, o2259

Moreno-Fuquen et al. · C14 H11 NO2

organic compounds Acta Crystallographica Section E

Data collection

Structure Reports Online

Oxford Xcalibur-S diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008) Tmin = 0.965, Tmax = 0.985

ISSN 1600-5368

Redetermination of 4-nitrostilbene a

a

Rodolfo Moreno-Fuquen, * Lina Aguirre and Alan R. Kennedyb

13263 measured reflections 3173 independent reflections 2202 reflections with I > 2(I) Rint = 0.027

Refinement R[F 2 > 2(F 2)] = 0.048 wR(F 2) = 0.135 S = 1.09 3173 reflections

154 parameters H-atom parameters constrained ˚ 3 max = 0.32 e A ˚ 3 min = 0.18 e A

a

Departamento de Quı´mica, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bDepartment of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland Correspondence e-mail: [email protected] Received 20 October 2008; accepted 29 October 2008 ˚; Key indicators: single-crystal X-ray study; T = 123 K; mean (C–C) = 0.002 A R factor = 0.048; wR factor = 0.135; data-to-parameter ratio = 20.6.

Table 1

˚ ,  ). Hydrogen-bond geometry (A D—H  A

D—H

H  A

D  A

D—H  A

C2—H2  O1i C12—H12  O1ii C12—H12  O2iii C11—H11  O2iii

0.95 0.95 0.95 0.95

2.55 2.66 2.74 2.90

3.3762 (17) 3.4139 (16) 3.4046 (17) 3.4820 (17)

146 137 128 121

Symmetry codes: (i) x  12; y þ 12; z þ 2; (ii) x þ 32; y; z  12; (iii) x; y þ 12; z  12.

In the title compound, C14H11NO2, the benzene rings are inclined to each other with a dihedral angle between their mean planes of 8.42 (6) . The nitro group is almost coplanar with the attached benzene ring but is rotated about the C—N bond by 5.84 (12) . This redetermination results in a crystal structure with significantly higher precision than the original determination [Hertel & Romer (1931). Z. Kristallogr. 76, 467–469], and the intermolecular interactions have been established. In the crystal structure, molecules are linked by C—H  O hydrogen bonds to generate C(5), C(13) and edgefused R33(28) rings.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).

Related literature

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2430).

For a previous study of the title compound, see: Hertel & Romer (1931). For background information on photonic materials, see: Luo et al. (2003); Vidal et al. (2008); Park et al. (2004). For general background, see: Allen et al. (1987); Etter (1990); Nardelli (1995).

Experimental Crystal data C14H11NO2 Mr = 225.24 Orthorhombic, Pbca ˚ a = 10.0839 (3) A ˚ b = 7.6849 (2) A ˚ c = 28.1176 (8) A

Acta Cryst. (2008). E64, o2259

˚3 V = 2178.94 (11) A Z=8 Mo K radiation  = 0.09 mm1 T = 123 (2) K 0.40  0.40  0.18 mm

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database (Allen, 2002). RMF also thanks the Universidad del Valle, Colombia, for partial financial support.

References Allen, F. H. (2002). Acta Cryst. B58, 380–388. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. 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. Etter, M. (1990). Acc. Chem. Res. 23, 120–126. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Hertel, E. & Romer, G. H. (1931). Z. Kristallogr. 76, 467–469. Luo, J., Haller, M., Li, H., Kim, T.-D. & Jen, A. K.-Y. (2003). Adv. Mater. 15, 1635–1638. Nardelli, M. (1995). J. Appl. Cryst. 28, 659. Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wrocław, Poland. Park, G., Jung, W. S. & Ra, C. S. (2004). Bull. Korean Chem. Soc. 25, 1427– 1429. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Vidal, X., Fedyanin, A., Molinos-Gomez, A., Rao, S., Martorell, J. & Petrov, D. (2008). Opt. Lett. 33, 699–701.

doi:10.1107/S1600536808035459

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