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Volume 69 
Part 2 
Page o246  
February 2013  

Received 20 December 2012
Accepted 10 January 2013
Online 19 January 2013

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Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.133
Data-to-parameter ratio = 13.0
Details
Open access

2,2-Dimethyl-2,3-dihydro-1H-perimidine

Sarah Maloney,a Alexandra M. Z. Slawina and J. Derek Woollinsa*

aEaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland
Correspondence e-mail: jdw3@st-and.ac.uk

The title compound, C13H14N2, was obtained from reaction of diaminonaphthalene with acetone. In both independent molecules in the asymmetric unit, the tricyclic perimidine consists of a planar (r.m.s. deviations = 0.0125 and 0.0181 Å) naphthalene ring system and an envelope conformation C4N2 ringwith the NCN group hinged with respect to the naphthalene backbone by 36.9 (2) and 41.3 (2)° in the two independent molecules. The methyl substituents are arranged approximately axial and equatorial on the apical C atom. In the crystal, one of the N-H groups of one independent molecule is involved in classical N-H...N hydrogen bonding. Short intermolecular (C/N)-H...[pi](arene) interactions, near the short T-shaped limit, link molecules in the absence of strong acceptors.

Related literature

For general background to perimidines and their biological activity, see: Shaabani & Maleki (2008[Shaabani, A. & Maleki, A. (2008). Chem. Pharm. Bull. 56, 79-81.]); Sauer et al. (2006[Sauer, M., Yeung, C., Lai, C.-C. & Chiu, S.-H. (2006). J. Org. Chem. 71, 775-788.]). For related structures, see: Martinez-Belmonte et al. (2010[Martinez-Belmonte, M., Escudero-Adan, E. C., Benet-Buchholz, J., Haak, R. M. & Kleij, A. W. (2010). Eur. J. Inorg. Chem. pp. 4823-4831.]).

[Scheme 1]

Experimental

Crystal data

  • C13H14N2

  • Mr = 198.27

  • Monoclinic, P 21 /c

  • a = 16.261 (10) Å

  • b = 7.710 (4) Å

  • c = 17.483 (10) Å

  • [beta] = 106.131 (12)°

  • V = 2105.6 (19) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 93 K

  • 0.12 × 0.12 × 0.12 mm
Data collection

  • Rigaku Mercury70 diffractometer

  • Absorption correction: multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.706, Tmax = 0.991

  • 12841 measured reflections

  • 3743 independent reflections

  • 2356 reflections with F2 > 2[sigma](F2)

  • Rint = 0.072
Refinement

  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.133

  • S = 0.96

  • 3743 reflections

  • 287 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C21-C25/C30, C25-C30 and C5-C10 rings, respectively.
D-H...A D-H H...A D...A D-H...A
N21-H21N...N29i 0.88 (2) 2.36 (2) 3.229 (4) 170 (2)
N1-H1N...Cg1ii 0.93 (3) 2.93 (3) 3.853 (3) 170 (2)
N9-H9N...Cg1 0.88 (4) 2.85 (2) 3.703 (3) 164 (2)
C12-H12C...Cg2 0.98 2.55 3.521 (3) 172
C26-H26...Cg3iii 0.95 2.53 3.456 (3) 164
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) x, y-1, z.

Data collection: CrystalClear-SM Expert (Rigaku, 2009[Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2107 ).

Acknowledgements

We are grateful to EPSRC for support.

References

Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Martinez-Belmonte, M., Escudero-Adan, E. C., Benet-Buchholz, J., Haak, R. M. & Kleij, A. W. (2010). Eur. J. Inorg. Chem. pp. 4823-4831.
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.
Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sauer, M., Yeung, C., Lai, C.-C. & Chiu, S.-H. (2006). J. Org. Chem. 71, 775-788.  [CSD] [CrossRef] [PubMed] [ChemPort]
Shaabani, A. & Maleki, A. (2008). Chem. Pharm. Bull. 56, 79-81.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2013). E69, o246  [ doi:10.1107/S1600536813000986 ]

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