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Volume 68 
Part 1 
Page o102  
January 2012  

Received 7 December 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.126
Data-to-parameter ratio = 17.1
Details
Open access

3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosane-(naphthalen-1-yl)methanol (1/2)

aDepartment of Chemistry, Andong National University, Andong 760-749, Republic of Korea,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

In the title co-crystal, C20H40N4·2C11H10O, the macrocycle is generated by a crystallographic inversion centre. The N atoms show a pyramidal coordination, and the cyclohexane ring that is fused to the 14-membered C10N4 ring exists in a chair conformation, whereas the methyl substituent occupies an axial site. The (naphthalen-1-yl)methanol molecule forms an O-H...N hydrogen bond to a cyclam N atom. The mean-square-plane passing through the 14-membered ring is approximately coplanar with the naphthalene fused-ring [dihedral angle = 6.6 (1)°].

Related literature

For the synthesis of the cyclam, see: Kang & Jeong (2003[Kang, S. G. & Jeong, J. H. (2003). Bull. Kor. Chem. Soc, 24, 393-396.]).

[Scheme 1]

Experimental

Crystal data
  • C20H40N4·2C11H10O

  • Mr = 652.94

  • Triclinic, [P \overline 1]

  • a = 8.9706 (4) Å

  • b = 9.4967 (6) Å

  • c = 10.5580 (5) Å

  • [alpha] = 92.500 (4)°

  • [beta] = 97.961 (4)°

  • [gamma] = 96.666 (4)°

  • V = 883.13 (8) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.978, Tmax = 0.985

  • 6926 measured reflections

  • 3915 independent reflections

  • 2958 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.126

  • S = 1.00

  • 3915 reflections

  • 229 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1o...N1 0.85 (1) 1.94 (1) 2.786 (2) 171 (2)

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5151 ).


Acknowledgements

We thank Andong National University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Kang, S. G. & Jeong, J. H. (2003). Bull. Kor. Chem. Soc, 24, 393-396.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o102  [ doi:10.1107/S160053681105272X ]

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