5,6-Dimeth­yl-1,10-phenanthroline

Sergio S Rozenel

doi:10.1107/S1600536813025087

. 2013 Sep 18;69(Pt 10):o1560. doi: 10.1107/S1600536813025087

5,6-Dimethyl-1,10-phenanthroline

Sergio S Rozenel ^a,^*

PMCID: PMC3790421 PMID: 24098240

Abstract

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 π–π 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 ▶) and Gasque et al. (1999 ▶), respectively. For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂
M _r = 208.26
Monoclinic,
a = 7.1932 (7) Å
b = 10.0572 (10) Å
c = 13.8729 (13) Å
β = 93.673 (5)°
V = 1001.55 (17) Å³
Z = 4
Mo Kα radiation
μ = 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 ▶) T _min = 0.991, T _max = 0.993
16500 measured reflections
1855 independent reflections
1613 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.100
S = 1.06
1855 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare, et al. 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-32 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) srd3013, I. DOI: 10.1107/S1600536813025087/bx2451sup1.cif

e-69-o1560-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025087/bx2451Isup2.hkl

e-69-o1560-Isup2.hkl^{(91.3KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813025087/bx2451Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

1. Comment

5,6-dimethyl-1,10-phenanthroline was obtained from Sigma-Aldrich. The distances and angles are consistent with those observed for [1,10]phenanthroline (Ton & Bolte, 2005) and coordinated 5,6-dimethyl-1,10-phenanthroline (Gasque, et al., 1999). The crystal packing is stabilized by an intermolecular C—H···N hydrogen bond interaction which links the molecules into chains with graph-set notation C(4) (Bernstein, et al., 1995) running parallel to the b axis. Weak intermolecular π-π interactions, involving the benzene rings, and the pyridine rings, respectively with an average plane-to plane separation of 3.5982 (7) Å further stabilize and reinforce the crystal structure.

2. Experimental

Crystals of the title compound, 5,6-dimethyl-1,10-phenanthroline, were obtained by sublimation at 160 °C under dynamic vacuum.