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

Choi, J.-H.; Subhan, M.A.; Ryoo, K.S.; Ng, S.W.

doi:10.1107/S160053681105272X

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 (C-C) = 0.002 Å
R = 0.049
wR = 0.126
Data-to-parameter ratio = 17.1
Details

3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane-(naphthalen-1-yl)methanol (1/2)

Jong-Ha Choi,^a Md Abdus Subhan,^a Keon Sang Ryoo ^a and Seik Weng Ng ^b,^c ^*

^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-HN 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).

Experimental

Crystal data

C₂₀H₄₀N₄·2C₁₁H₁₀O
M_r = 652.94
Triclinic, $[P \overline 1]$
a = 8.9706 (4) Å
b = 9.4967 (6) Å
c = 10.5580 (5) Å
= 92.500 (4)°
= 97.961 (4)°
= 96.666 (4)°
V = 883.13 (8) Å³
Z = 1
Mo K radiation
= 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) T_min = 0.978, T_max = 0.985
6926 measured reflections
3915 independent reflections
2958 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(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
_max = 0.29 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1oN1	0.85 (1)	1.94 (1)	2.786 (2)	171 (2)

Data collection: CrysAlis PRO (Agilent, 2010); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Kang, S. G. & Jeong, J. H. (2003). Bull. Kor. Chem. Soc, 24, 393-396.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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