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Volume 69 
Part 8 
Pages o1301-o1302  
August 2013  

Received 19 June 2013
Accepted 16 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.072
wR = 0.167
Data-to-parameter ratio = 16.6
Details
Open access

N2-(4-Methoxysalicylidene)arginine hemihydrate

aDepartment of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore 641020, Tamil Nadu, India,bSchool of Chemistry, University of Hyderabad, Hyderabad 500 046, Andhra Pradesh, India, and cDepartment of Physics, The New College (Autonomous), Chennai 600 014, TamilNadu, India
Correspondence e-mail: mnizam_new@yahoo.in

The title compound, C14H20N4O4·0.5H2O [systematic name: (2S)-5-{[amino(iminiumyl)methyl]amino}-2-{[(1Z)-4-methoxy-2-oxidobenzylidene]azaniumyl}pentanoate hemihydrate], has been synthesized by the reaction of L-arginine and 4-methoxysalicylaldehyde and crystallizes with two independent substituted L-arginine molecules and one water molecule of solvation in the asymmetric unit. Each molecule exists as a zwitterion and adopts a Z configuration about the central C=N. The molecular conformation is stabilized by strong intramolecular N-H...O hydrogen bonds that generate S(6) and S(10) ring motifs. Intermolecular N-H...O and O-H...O hydrogen bonds involving also the water molecule and weak intermolecular C-H...Owater interactions link the molecules into an infinite one-dimensional ribbon structure extending along the b axis. The known (2S) absolute configuration for L-arginine was invoked. Weak intermolecular C-H...[pi] interactions are also present.

Related literature

For the synthesis of similar compounds, see: Srinivasan et al. (1986[Srinivasan, K., Michaud, P. & Kochi, J. K. (1986). J. Am. Chem. Soc. 108, 2309-2320.]); Moutet & Ourari (1997[Moutet, J. C. & Ourari, A. (1997). Electrochim. Acta, 42, 2525-2531.]). For general background on Schiff bases, see: von Konig et al. (1982[Konig, A. von, Moll, F. & Rosenhahn, L. (1982). US Patent 4358531.]); Lewis et al. (2009[Lewis, J., Matteucci, M., Chen, T. & Jiao, H. (2009). WO Patent 2009140553 A2.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Oueslati et al. (2007[Oueslati, A., Kefi, R., Ben Nasr, C. & Lefebvre, F. (2007). J. Mol. Struct. 871, 49-58.]).

[Scheme 1]

Experimental

Crystal data
  • C14H20N4O4·0.5H2O

  • Mr = 317.35

  • Monoclinic, P 21

  • a = 10.1828 (11) Å

  • b = 10.3414 (11) Å

  • c = 15.5542 (16) Å

  • [beta] = 102.688 (2)°

  • V = 1597.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.976

  • 18648 measured reflections

  • 7483 independent reflections

  • 5859 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.167

  • S = 1.10

  • 7483 reflections

  • 452 parameters

  • 14 restraints

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.89 (1) 1.94 (3) 2.638 (4) 134 (3)
N4-H4A...O4 0.90 (1) 2.06 (1) 2.935 (4) 165 (3)
N5-H5...O6 0.90 (1) 1.90 (3) 2.600 (4) 134 (3)
N8-H8A...O7 0.90 (1) 2.03 (1) 2.914 (4) 166 (3)
N2-H2...O2i 0.86 1.92 2.758 (4) 166
N3-H3A...O3i 0.89 (1) 2.58 (3) 3.333 (4) 142 (3)
N3-H3B...O4ii 0.89 (1) 1.93 (1) 2.817 (4) 175 (4)
N4-H4B...O3ii 0.89 (1) 2.03 (1) 2.912 (4) 171 (3)
N6-H6...O6iii 0.86 1.89 2.705 (4) 158
N7-H7A...O8iii 0.89 (1) 2.50 (3) 3.202 (4) 135 (3)
N7-H7B...O7iv 0.90 (1) 1.91 (1) 2.800 (4) 173 (3)
N8-H8B...O8iv 0.89 (1) 2.05 (2) 2.911 (4) 161 (3)
O1W-H2W...O3v 0.94 (1) 1.98 (2) 2.881 (5) 159 (6)
C15-H15C...O1Wi 0.96 2.56 3.451 (7) 155
C22-H22...O1W 0.93 2.53 3.359 (6) 149
C1-H1C...Cg1vi 0.96 2.96 3.669 (4) 132
C15-H15C...Cg2vii 0.96 2.98 3.762 (5) 139
Symmetry codes: (i) x, y-1, z; (ii) [-x, y-{\script{1\over 2}}, -z]; (iii) x, y+1, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+1]; (v) x+1, y, z; (vi) [-x, y-{\script{1\over 2}}, -z+1]; (vii) [-x+1, y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: ZS2267 ).


Acknowledgements

MS thanks the UGC Networking Centre, School of Chemistry, University of Hyderabad, India, for the award of a Visiting Research Fellowship to use the facilities at the School. The authors also thank for access to the X-ray diffraction equipment.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Konig, A. von, Moll, F. & Rosenhahn, L. (1982). US Patent 4358531.
Lewis, J., Matteucci, M., Chen, T. & Jiao, H. (2009). WO Patent 2009140553 A2.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Moutet, J. C. & Ourari, A. (1997). Electrochim. Acta, 42, 2525-2531.  [CrossRef] [ChemPort] [Web of Science]
Oueslati, A., Kefi, R., Ben Nasr, C. & Lefebvre, F. (2007). J. Mol. Struct. 871, 49-58.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Srinivasan, K., Michaud, P. & Kochi, J. K. (1986). J. Am. Chem. Soc. 108, 2309-2320.  [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1301-o1302   [ doi:10.1107/S1600536813019727 ]

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