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Volume 69 
Part 10 
Page o1560  
October 2013  

Received 29 August 2013
Accepted 9 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.100
Data-to-parameter ratio = 10.8
Details
Open access

5,6-Dimethyl-1,10-phenanthroline

aChemistry Department and Chemical Sciences Division of Lawrence Berkeley National Laboratory, University of California, Berkeley, California 94720, USA
Correspondence e-mail: SSrozenel@lbl.gov

In the title compound, C14H12N2, the N...N distance is 2.719 (1) Å. The N-C-C-N torsion angle [0.9 (1)°] is close to the ideal value of 0° as expected. Bond lengths and angles are consistent with those observed for [1,10]phenanthroline and coordinated 5,6 dimethyl[1,10]phenanthroline. In the crystal, C-H...N hydrogen bonds link the molecules into C(4) chains running parallel to the b axis. Weak [pi]-[pi] interactions between benzene and pyridine rings [centroid-centroid distance = 3.5337 (7) Å] and between benzene rings [centroid-centroid distances = 3.6627 (7) and 3.8391 (7)Å] also occur.

Related literature

For [1,10]phenanthroline and 5,6-dimethyl[1,10]phenanthroline, see: Ton & Bolte (2005[Ton, Q. C. & Bolte, M. (2005). Acta Cryst. E61, o1406-o1407.]) and Gasque et al. (1999[Gasque, L., Moreno-Esparza, R., Mollins, E., Briansó-Penalva, J. L., Ruiz-Ramírez, L. & Medina-Dickinson, G. (1999). Acta Cryst. C55, 158-160.]), respectively. 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.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2

  • Mr = 208.26

  • Monoclinic, P 21 /c

  • a = 7.1932 (7) Å

  • b = 10.0572 (10) Å

  • c = 13.8729 (13) Å

  • [beta] = 93.673 (5)°

  • V = 1001.55 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.11 × 0.10 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.991, Tmax = 0.993

  • 16500 measured reflections

  • 1855 independent reflections

  • 1613 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.100

  • S = 1.06

  • 1855 reflections

  • 171 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N1i 0.945 (14) 2.439 (13) 3.3718 (15) 169.0 (10)
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare, et al. 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-32 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2451 ).


Acknowledgements

The author thanks Professor Richard Andersen and Dr DiPasquale for their support. This work was supported by the Director, Office of Science, Office of Basic Energy Sciences, and the Division of Chemical Sciences, Geosciences, and Biosciences of the US Department of Energy under contract No. DE-AC02-05CH11231.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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 (2009). APEX2, SAINT 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]
Gasque, L., Moreno-Esparza, R., Mollins, E., Briansó-Penalva, J. L., Ruiz-Ramírez, L. & Medina-Dickinson, G. (1999). Acta Cryst. C55, 158-160.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Ton, Q. C. & Bolte, M. (2005). Acta Cryst. E61, o1406-o1407.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1560  [ doi:10.1107/S1600536813025087 ]

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