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Volume 62 
Part 5 
Pages o1816-o1818  
May 2006  

Received 31 March 2006
Accepted 31 March 2006
Online 11 April 2006

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© International Union of Crystallography 2006

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.098
Data-to-parameter ratio = 7.8
Details

A hydrogen-bonded C(6) chain in glyoxal 3-nitrophenylhydrazone

John N. Low,a James L. Wardellb and Christopher Glidewellc*

aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland,bInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, and cSchool of Chemistry, University of St Andrews, Fife, KY16 9ST, Scotland
Correspondence e-mail: cg@st-andrews.ac.uk

The molecules of the title compound, C8H7N3O3, which are nearly planar, are linked into simple C(6) chains by an N-H...O hydrogen bond.

Comment

The title compound, (I)[link], was prepared as part of our continuing study of the supramolecular arrangements of N-(nitropheny)imide and hydrazone derivatives. We have recently reported the supramolecular structure of the isomeric compound glyoxal 4-nitrophenylhydrazone, (II), in which triple helices enclose two types of channel lying respectively along [\overline{4}], and 41 or 43 axes in space group I41/a (Glidewell et al., 2005[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o493-o495.]): the supramolecular structure of (I)[link], by contrast, is very simple.

[Scheme 1]

The molecules of compound (I)[link] (Fig. 1[link]) are almost planar, as shown by the leading torsion angles (Table 1[link]); the side chain between atoms N1 and O1 adopts a planar all-trans conformation, and the nitro group is nearly coplanar with the aryl ring. There is strong bond fixation in the side chain with very short N2-C11 and C12-O1 bonds, with no evidence for bond polarization in this fragment.

A single hydrogen bond (Table 2[link]) links the molecules into chains; atom N1 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O1 in the molecule at (-[{1\over 2}] + x, [{1\over 2}] - y, [{1\over 2}] + z), forming a C(6) chain running parallel to the [10[\overline{1}]] direction and generated by the n-glide plane at y = 0.25 (Fig. 2[link]). Two such chains pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

[Figure 1]
Figure 1
A molecule of compound (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of compound (I)[link], showing the formation of a C(6) hydrogen-bonded chain along [10[\overline{1}]]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (-[{1\over 2}] + x, [{1\over 2}] - y, [{1\over 2}] + z) and ([{1\over 2}] + x, [{1\over 2}] - y, -[{1\over 2}] + z), respectively.

Experimental

Compound (I)[link] was prepared by heating under reflux for 1 h a solution of glyoxal (1 mmol as a 40% aqueous solution) and 3-nitrophenylhydrazine (1 mmol) in methanol (40 ml). The mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. The residue was crystallized from ethanol to yield crystals suitable for single-crystal X-ray diffraction.

Crystal data

  • C8H7N3O3

  • Mr = 193.17

  • Monoclinic, C c

  • a = 7.4737 (4) Å

  • b = 19.7711 (13) Å

  • c = 6.0262 (4) Å

  • [beta] = 107.080 (4)°

  • V = 851.18 (9) Å3

  • Z = 4

  • Dx = 1.507 Mg m-3

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 120 (2) K

  • Lath, yellow

  • 0.16 × 0.08 × 0.02 mm
Data collection

  • Bruker-Nonius KappaCCD diffractometer

  • [varphi] and [omega] scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.961, Tmax = 0.998

  • 7928 measured reflections

  • 987 independent reflections

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

  • Rint = 0.063

  • [theta]max = 27.6°
Refinement

  • Refinement on F2

  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.098

  • S = 1.08

  • 987 reflections

  • 127 parameters

  • H-atom parameters constrained

  • w = 1/[[sigma]2(Fo2) + (0.0568P)2 + 0.1446P] where P = (Fo2 + 2Fc2)/3

  • ([Delta]/[sigma])max < 0.001

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Selected geometric parameters (Å, °)

C1-N1 1.395 (3)
N1-N2 1.331 (3)
N2-C11 1.294 (3)
C11-C12 1.445 (4)
C12-O1 1.224 (3)
C2-C1-N1-N2 -3.6 (4)
C1-N1-N2-C11 -175.8 (2)
N1-N2-C11-C12 -179.1 (2)
N2-C11-C12-O1 -177.1 (3)
C2-C3-N3-O31 6.7 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.88 2.15 2.940 (3) 149
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

All H atoms were located in difference maps and then treated as riding atoms, with C-H = 0.95 Å and N-H = 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N). In the absence of significant anomalous dispersion the Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) parameter was indeterminate and it was not possible to determine the correct orientation of the structure with respect to the polar axis directions. Accordingly, the Friedel-equivalent reflections were merged prior to the final refinement.

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (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.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. The authors thank the staff for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Flack, H. D. (1983). Acta Cryst. A39, 876-881. [CrossRef] [details]
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o493-o495. [CrossRef] [details]
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.
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. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2006). E62, o1816-o1818   [ doi:10.1107/S160053680601186X ]