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

Lemmerer, A.; Bernstein, J.; Kahlenberg, V.

doi:10.1107/S1600536811054043

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 (C-C) = 0.002 Å
R = 0.029
wR = 0.077
Data-to-parameter ratio = 12.1
Details

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

Andreas Lemmerer,^a ^* Joel Bernstein ^b and Volker Kahlenberg ^c

^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). 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-HO hydrogen bonds and one O-HN hydrogen bond. The O-HN hydrogen bond formed between the carboxyl group and the pyridine ring is supported by a C-HO hydrogen bond.

Related literature

For the first polymorph, see: Lemmerer et al. (2011). For experimental techniques, see: Friscic et al. (2009); Skovsgaard & Bond (2009); Karki et al. (2009). For hydrogen-bonding motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

2C₆H₇N₃O·C₆H₁₀O₄
M_r = 420.43
Monoclinic, P 2₁ /c
a = 15.9747 (4) Å
b = 7.3309 (2) Å
c = 8.7451 (2) Å
= 103.729 (3)°
V = 994.87 (4) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.92, T_max = 0.98
6207 measured reflections
1845 independent reflections
1487 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(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
_max = 0.18 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3ⁱ	0.877 (14)	2.174 (15)	3.0409 (14)	169.7 (11)
N3-H3AO1ⁱⁱ	0.934 (14)	2.129 (14)	3.0349 (14)	163.0 (12)
N3-H3BO1ⁱⁱⁱ	0.888 (15)	2.258 (16)	3.1426 (14)	173.7 (13)
O2-H2N2	0.950 (19)	1.671 (19)	2.6126 (13)	170.3 (16)
C2-H2AO3	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2011). CrystEngComm, 13, 55-59.
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Skovsgaard, S. & Bond, A. D. (2009). CrystEngComm, 11, 444-453.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds