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Volume 68 
Part 1 
Page o190  
January 2012  

Received 12 December 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.077
Data-to-parameter ratio = 12.1
Details
Open access

Form II of adipic acid-nicotinohydrazide (1/2)

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, PO Wits 2050, South Africa,bFaculty of Science, NYU Abu Dhabi, PO Box 129188, Abu Dhabi, United Arab Emirates, and cInstitute of Mineralogy and Petrography, University of Innsbruck, Innsbruck 6020, Austria
Correspondence e-mail: andreas.lemmerer@wits.ac.za

The crystal structure of the title co-crystal, 2C6H7N3O·C6H10O4, is a second polymorph, designated form II, of the co-crystal formed between the two molecules [Lemmerer et al. (2011[Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2011). CrystEngComm, 13, 55-59.]). CrystEngComm, 13, 55-59]. The asymmetric unit comprises one molecule of nicotinic acid hydrazide, and one half-molecule of adipic acid (the entire molecule is completed by the application of a centre of inversion). In the crystal, molecules assemble into a three-dimensional network of hydrogen bonds, formed by three N-H...O hydrogen bonds and one O-H...N hydrogen bond. The O-H...N hydrogen bond formed between the carboxyl group and the pyridine ring is supported by a C-H...O hydrogen bond.

Related literature

For the first polymorph, see: Lemmerer et al. (2011[Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2011). CrystEngComm, 13, 55-59.]). For experimental techniques, see: Friscic et al. (2009[Friscic, T., Childs, S. L., Rizvi, S. A. A. & Jones, W. (2009). CrystEngComm, 11, 418-426.]); Skovsgaard & Bond (2009[Skovsgaard, S. & Bond, A. D. (2009). CrystEngComm, 11, 444-453.]); Karki et al. (2009[Karki, S., Friscic, T. & Jones, W. (2009). CrystEngComm, 11, 470-481.]). For hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • 2C6H7N3O·C6H10O4

  • Mr = 420.43

  • Monoclinic, P 21 /c

  • a = 15.9747 (4) Å

  • b = 7.3309 (2) Å

  • c = 8.7451 (2) Å

  • [beta] = 103.729 (3)°

  • V = 994.87 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.32 × 0.28 × 0.04 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini ultra Mo) detector

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.92, Tmax = 0.98

  • 6207 measured reflections

  • 1845 independent reflections

  • 1487 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.077

  • S = 1.02

  • 1845 reflections

  • 153 parameters

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.877 (14) 2.174 (15) 3.0409 (14) 169.7 (11)
N3-H3A...O1ii 0.934 (14) 2.129 (14) 3.0349 (14) 163.0 (12)
N3-H3B...O1iii 0.888 (15) 2.258 (16) 3.1426 (14) 173.7 (13)
O2-H2...N2 0.950 (19) 1.671 (19) 2.6126 (13) 170.3 (16)
C2-H2A...O3 0.95 2.73 3.3838 (14) 126
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5035 ).


Acknowledgements

This work was supported in part by grant No. 2004118 from the United States-Israel Binational Science Foundation (Jerusalem). AL thanks the South African National Research Foundation for a postdoctoral scholarship (SFP2007070400002) and the Oppenheimer Memorial Trust for financial support, and the Molecular Sciences Institute for infrastucture.

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Friscic, T., Childs, S. L., Rizvi, S. A. A. & Jones, W. (2009). CrystEngComm, 11, 418-426.
Karki, S., Friscic, T. & Jones, W. (2009). CrystEngComm, 11, 470-481.  [CSD] [CrossRef] [ChemPort]
Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2011). CrystEngComm, 13, 55-59.  [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Skovsgaard, S. & Bond, A. D. (2009). CrystEngComm, 11, 444-453.  [ISI] [CSD] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o190  [ doi:10.1107/S1600536811054043 ]

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