1-Benz­yloxy-4-(2-nitro­ethen­yl)benzene

Kennedy, A.R.; Kipkorir, Z.R.; Muhanji, C.I.; Okoth, M.O.

doi:10.1107/S1600536810042960

Volume 66
Part 11
Pages o2984-o2985
November 2010

Received 19 October 2010
Accepted 21 October 2010
Online 30 October 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.006 Å
R = 0.088
wR = 0.170
Data-to-parameter ratio = 14.3
Details

1-Benzyloxy-4-(2-nitroethenyl)benzene

Alan R. Kennedy,^a Zaccheus R. Kipkorir,^b Claire I. Muhanji ^b and Maurice O. Okoth ^b ^*

^aDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, and ^bDepartment of Chemistry and Biochemistry, Moi University, PO Box 1125-30100, Eldoret, Kenya
Correspondence e-mail: okothmdo@mu.ac.ke

The title compound, C₁₅H₁₃NO₃, crystallizes with three independent molecules per asymmetric unit (Z' = 3). One of these molecules is found to have a configuration with a greater twist between its two aromatic rings than the other two [compare 70.26 (13) and 72.31 (12)° with 84.22 (12)°]. There are also differences in the number and nature of the weak intermolecular C-HO contacts formed by each of the three molecules.

Related literature

For discussion of C-HO contacts in related derivatives, see: Gerkin (1999). For other related structures, see: Gao et al. (2008); Stomberg & Lundquist (1994); Wang et al. (2007); Zheng et al. (2008); Kennedy et al. (2010). On the design of new small molecules that target HIV-1 binding sites, see: Younis et al. (2010); Hunter et al. (2008); Jones et al. (2006). For background to the antiretroviral treatment programme for AIDS, see: UNAIDS/WHO (2009).

Experimental

Crystal data

C₁₅H₁₃NO₃
M_r = 255.26
Triclinic, $[P \overline 1]$
a = 9.9522 (8) Å
b = 14.0456 (13) Å
c = 14.2506 (10) Å
= 74.416 (5)°
= 84.188 (5)°
= 80.888 (4)°
V = 1891.0 (3) Å³
Z = 6
Mo K radiation
= 0.09 mm^-1
T = 120 K
0.12 × 0.10 × 0.05 mm

Data collection

Bruker-Nonius APEXII CCD diffractometer
25754 measured reflections
7366 independent reflections
4735 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.088
wR(F²) = 0.170
S = 1.14
7366 reflections
514 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O8ⁱ	0.95	2.56	3.503 (5)	175
C8-H8O8ⁱ	0.95	2.38	3.322 (5)	175
C5-H5O9ⁱⁱ	0.95	2.58	3.493 (4)	162
C12-H12O4ⁱⁱⁱ	0.95	2.46	3.284 (5)	145
C20-H20O5^iv	0.95	2.49	3.373 (4)	155
C22-H22O5^iv	0.95	2.59	3.448 (4)	150
C18-H18O6^v	0.95	2.40	3.326 (4)	166
C33-H33O3ⁱⁱ	0.95	2.40	3.325 (4)	163
C45-H45O1^vi	0.95	2.58	3.413 (5)	147
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y, -z+2; (iii) x, y, z-1; (iv) -x+2, -y+2, -z+1; (v) -x+1, -y+2, -z+1; (vi) -x+1, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2304 ).

Acknowledgements

We are grateful to the National Crystallography Service, University of Southampton, for data collection. MOO also thanks the Commonwealth Scholarship Commission and the British Council for funding and Moi University for sabatical leave.

References

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Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
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UNAIDS/WHO (2009). Report on the global AIDS epidemic, 17th April 2009. http://www.unaids.org 2008.
Wang, D.-J., Fan, L. & Zheng, J. (2007). Acta Cryst. E63, o2979.
Younis, Y., Hunter, R., Muhanji, C. I., Hale, I., Singh, R., Bailey, C. M., Sullivan, T. J. & Anderson, K. S. (2010). Bioorg. Med. Chem. 18, 4661-4673.
Zheng, C.-Y., Wang, D.-J. & Fan, L. (2008). Acta Cryst. E64, o2326.

organic compounds