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Volume 70 
Part 1 
Page o50  
January 2014  

Received 13 September 2013
Accepted 13 November 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.185
Data-to-parameter ratio = 26.0
Details
Open access

5,5,7,12,12,14-Hexamethyl-1,8-bis­(4-nitro­benz­yl)-1,4,8,11-tetra­aza­cyclo­tetra­deca­ne

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Inorganic Chemistry, University of Madras, Maraimalai Campus, Chennai-25, Tamilnadu, India
Correspondence e-mail: guqmc@yahoo.com

The asymmetric unit of the title compound, C30H46N6O4, contains one half-mol­ecule. The C(benzene)-C(CH2)-N-C(-Me) torsion angle is -79.89 (13)° suggesting a synclinal orientation of the nitro­benzene ring with respect to the macrocycle. The conformation of the macrocycle is stabilized by intra­molecular N-H...N hydrogen bonds.

Related literature

For the biological activity of cyclam derivatives, see: Cronin et al. (1999[Cronin, L., Mount, A. R., Parsons, S. & Robertson, N. (1999). J. Chem. Soc. Dalton Trans. pp. 1925-1927.]); Fzerov et al. (2005[Fzerov, S., Kotek, J., Csaov, I., Hermann, P., Koen Binnemans, K. & Luke, I. (2005). Dalton Trans. pp. 2908-2915.]). For related structures, see: Xie et al. (2008[Xie, B., Zou, L.-K., He, Y.-G., Feng, J.-S. & Zhang, X.-L. (2008). Acta Cryst. E64, m622.]); Feng et al. (2009[Feng, J.-S., Zou, L.-K., Xie, B. & Wu, Y. (2009). Acta Cryst. E65, m1022.]).

[Scheme 1]

Experimental

Crystal data
  • C30H46N6O4

  • Mr = 554.73

  • Triclinic, [P \overline 1]

  • a = 8.6407 (4) Å

  • b = 9.1433 (3) Å

  • c = 11.0008 (5) Å

  • [alpha] = 107.742 (2)°

  • [beta] = 104.898 (2)°

  • [gamma] = 102.372 (2)°

  • V = 758.45 (6) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 273 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.980

  • 18201 measured reflections

  • 4819 independent reflections

  • 3340 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.185

  • S = 0.96

  • 4819 reflections

  • 185 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...N2i 0.883 (17) 2.284 (17) 2.9770 (15) 135.3 (15)
Symmetry code: (i) -x, -y+1, -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: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2199 ).


Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cronin, L., Mount, A. R., Parsons, S. & Robertson, N. (1999). J. Chem. Soc. Dalton Trans. pp. 1925-1927.  [CSD] [CrossRef]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Feng, J.-S., Zou, L.-K., Xie, B. & Wu, Y. (2009). Acta Cryst. E65, m1022.  [CSD] [CrossRef] [IUCr Journals]
Fzerov, S., Kotek, J., Csaov, I., Hermann, P., Koen Binnemans, K. & Luke, I. (2005). Dalton Trans. pp. 2908-2915.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Xie, B., Zou, L.-K., He, Y.-G., Feng, J.-S. & Zhang, X.-L. (2008). Acta Cryst. E64, m622.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2014). E70, o50  [ doi:10.1107/S1600536813031164 ]

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