N 2-o-Tolyl­benzamidine

Li-Zeng Zhang; Hong-Bo Tong

doi:10.1107/S1600536808017625

. 2008 Jun 19;64(Pt 7):o1276. doi: 10.1107/S1600536808017625

N ²-o-Tolylbenzamidine

Li-Zeng Zhang ^a, Hong-Bo Tong ^a,^*

PMCID: PMC2961687 PMID: 21202908

Abstract

The asymmetric unit of the title compound, C₁₄H₁₄N₂, contains two independent molecules with slightly different conformations; the dihedral angles formed by aromatic rings in the two molecules are 73.2 (1) and 75.0 (1)°. Intermolecular N—H⋯N hydrogen bonds link the molecules into chains extended in the [100] direction.

Related literature

For general background, see Bourget-Merle et al. (2002 ▶). For a related crystal structure, see Surma et al. (1988 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂
M _r = 210.27
Triclinic,
a = 10.347 (2) Å
b = 10.697 (2) Å
c = 11.495 (2) Å
α = 97.088 (4)°
β = 103.184 (4)°
γ = 95.898 (4)°
V = 1218.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T _min = 0.980, T _max = 0.986
4978 measured reflections
4158 independent reflections
2913 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.235
S = 1.09
4158 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017625/cv2419sup1.cif

e-64-o1276-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017625/cv2419Isup2.hkl

e-64-o1276-Isup2.hkl^{(203.7KB, hkl)}

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
N2—H2B⋯N3	0.86	2.25	3.049 (3)	156
N4—H4B⋯N1ⁱ	0.86	2.24	3.016 (3)	151

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Youth Foundation of Shanxi University (grant No. 2006026, China) for financial support.

supplementary crystallographic information

Comment

β-Diketiminate complexes are among the most common chelate systems in coordination chemistry (Bourget-Merle et al., 2002). Inspired by getting new chelate system with amidine motif, we got the title compound (I) by additional reaction of PhCN with o-methyl aniline lithium.

The asymmetric unit of (I) contains two independent molecules (Fig. 1), denoted A and B. The N=C bond lengths in both molecules (Table 1) agree well with the corresponding values reported for similar compounds (Surma et al., 1988). The conformations of the two independent molecules are slightly different. In molecule A, the mean plane N3/C22/N4 makes dihedral angles of 85.3 (1) and 21.5 (1)° with phenyl rings C16–C21and C23–C28, respectively. In molecule B, the mean plane N1/C8/N2 makes dihedral angles 86.8 (1) and 18.2 (1)° with phenyl rings C2–C7 and C9–C14, respectively.

In the crystal, intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into chains extended in direction [100].

Experimental

All experiments were performed under an atmosphere of pure argon using Schlenk apparatus and a vacuum line, unless otherwise stated. The solvents used were of reagent grade or better and were freshly distilled under dry dinitrogen and degassed prior to use. Slowly added PhCN(1.03 g,10 mmol)to the solution of compound o-methyl-PhNHLi (1.13 g,10 mmol) in hexane (ca 40 ml)at -0°C., and then stirred for further 12 h.Add it to cold water, and then use chlorform to extract organic phase.The organic phase was slowly concentrated and get the crystal of the title compound.