Hydrogen bonding in 1-carb­oxy­propanaminium nitrate

Messai, A.; Benali-Cherif, R.; Jeanneau, E.; Benali-Cherif, N.

doi:10.1107/S1600536812013682

Volume 68
Part 5
Pages o1307-o1308
May 2012

Received 7 March 2012
Accepted 29 March 2012
Online 4 April 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.109
Data-to-parameter ratio = 13.2
Details

Hydrogen bonding in 1-carboxypropanaminium nitrate

Amel Messai,^a Rim Benali-Cherif,^a ^* Erwann Jeanneau ^b and Nourredine Benali-Cherif ^a

^aLaboratoire des Structures, Propriétés et Interactions Interatomiques, Université Abbes Laghrour Khenchela, 40000 Khenchela, Algeria, and ^bUniversité Claude Bernard Lyon 1, Laboratoire des Multimatériaux et Interfaces (UMR 5615), 69622 Villeurbanne Cedex, France
Correspondence e-mail: benalicherif@hotmail.com

There are two crystallographically independent cations and two anions in the asymmetric unit of the title compound, C₄H₅NO₂⁺·NO₃^-. In the crystal, the 1-carboxypropanaminium cations and nitrate anions are linked to each other through strong N-HO and O-HO hydrogen bonds, forming a three-dimensional complex network. C-HO interactions also occur.

Related literature

For background to inorganic-organic hybrid materials, see: Benali-Cherif, Allouche et al. (2007); Benali-Cherif, Kateb et al. (2007); Messai et al. (2009); Cherouana et al. (2003). Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999) by multi-scan inter-frame scaling.

Experimental

Crystal data

C₄H₁₀NO₂⁺·NO₃^-
M_r = 166.14
Monoclinic, P 2₁ /c
a = 18.274 (2) Å
b = 5.6052 (4) Å
c = 16.536 (2) Å
= 116.224 (16)°
V = 1519.4 (3) Å³
Z = 8
Cu K radiation
= 1.18 mm^-1
T = 150 K
0.1 × 0.02 × 0.01 mm

Data collection

Oxford Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.987, T_max = 0.999
14871 measured reflections
2683 independent reflections
2441 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.109
S = 1.08
2683 reflections
203 parameters
H-atom parameters not refined
_max = 0.25 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AO1Aⁱ	0.89	2.11	2.8590 (18)	141
N1A-H1AO5Bⁱⁱ	0.89	2.48	2.9464 (18)	113
N1A-H1BO3Bⁱⁱⁱ	0.89	2.01	2.8877 (17)	169
N1A-H1BO4Bⁱⁱⁱ	0.89	2.44	3.0033 (16)	121
N1A-H1CO4B	0.89	1.93	2.8162 (16)	173
O2A-H2OO3B^iv	0.82	1.84	2.6295 (17)	160
N1B-H3CO1B^v	0.89	2.08	2.8470 (16)	143
N1B-H3CO5A^v	0.89	2.50	2.946 (2)	111
N1B-H3DO3A^vi	0.89	2.47	2.9917 (16)	118
N1B-H3DO4A^vi	0.89	2.02	2.9025 (16)	169
N1B-H3EO3A^vii	0.89	1.94	2.8126 (16)	168
O2B-H4O4A	0.82	1.84	2.6206 (16)	159
C4A-H4BO3Bⁱⁱⁱ	0.96	2.58	3.382 (2)	141
C2B-H6O3A^vi	0.98	2.57	3.189 (2)	121
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x, y-1, z; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: Gemini User Manual (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). Gemini User Manual. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RU2030 ).

Acknowledgements

We thank Professor Dominique Luneau (Laboratoire des Multimatériaux et Interfaces UMR 5615, Université Claude Bernard Lyon 1, France) for the diffraction facilities. We also thank Abbes Laghrour Khenchela University and the Ministère de l'Enseignement Supérieur et de la Recherche Scientifique-Algeria for financial support via the PNE programme.

References

Benali-Cherif, N., Allouche, F., Direm, A., Boukli-H-Benmenni, L. & Soudani, K. (2007). Acta Cryst. E63, o2643-o2645.
Benali-Cherif, N., Kateb, A., Boussekine, H., Boutobba, Z. & Messai, A. (2007). Acta Cryst. E63, o3251.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Cherouana, A., Benali-Cherif, N. & Bendjeddou, L. (2003). Acta Cryst. E59, o180-o182.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
Messai, A., Direm, A., Benali-Cherif, N., Luneau, D. & Jeanneau, E. (2009). Acta Cryst. E65, o460.
Oxford Diffraction (2006). Gemini User Manual. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds