(9H-Carbazol-9-ylmeth­yl)diethyl­amine

Wei-Jin Gu; Zi-Ting Lin; Bing-Xiang Wang

doi:10.1107/S1600536810047197

. 2010 Nov 20;66(Pt 12):o3245. doi: 10.1107/S1600536810047197

(9H-Carbazol-9-ylmethyl)diethylamine

Wei-Jin Gu ^a,^*, Zi-Ting Lin ^a, Bing-Xiang Wang ^a

PMCID: PMC3011667 PMID: 21589532

Abstract

The asymmetric unit of the title compound, C₁₇H₂₀N₂, contains two molecules, whose bond lengths and angles differ only slightly. In the crystal, neighbouring molecules form pillar structures via edge-to-face π–π stacking interactions [edge-to-face distances = 3.538 (3) and 3.496 (3)Å].

Related literature

Carbazole-based compounds are widely used in OLEDs as emitters because of their intense luminescence, see: Adhikari et al. (2007 ▶); Liu et al. (2006 ▶); Palayangoda et al. (2008 ▶) and as organic fluorescence probes, see: Hao et al. (2010 ▶); Pappayee & Mishra, (2000 ▶). For our studies of organic fluorescence probes, see: Shen et al. (2006 ▶, 2008 ▶). For the preparation of the title compound, see: Gu et al. (1997 ▶).

Experimental

Crystal data

C₁₇H₂₀N₂
M _r = 252.35
Monoclinic,
a = 24.338 (2) Å
b = 6.3216 (11) Å
c = 19.133 (2) Å
β = 104.109 (2)°
V = 2854.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 291 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.981, T _max = 0.985
13429 measured reflections
5463 independent reflections
3052 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.120
S = 1.06
5463 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008) ▶; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047197/hg2745sup1.cif

e-66-o3245-sup1.cif^{(28.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047197/hg2745Isup2.hkl

e-66-o3245-Isup2.hkl^{(267.5KB, hkl)}

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

Acknowledgments

We thank the Natural Science Foundation of Jiangsu Province, China (grant No. BK2008435) and the National Natural Science Foundation of China (grant No. 20771060) for financial support.

supplementary crystallographic information

Comment

Carbazole-based compounds are known for their intense luminescence and widely used in OLEDs as emitters (Adhikari et al., 2007; Liu et al., 2006; Palayangoda et al., 2008). They can also be used as organic fluorescence probes (Hao et al., 2010; Pappayee et al., 2000). In our continuing studies in organic fluorescence probes (Shen et al., 2008; Shen et al., 2006), the 9-diethylaminomethyl carbazole(I) was synthesized.

The crystal structure of the title compound, C₁₇H₂₀N₂, reveals that all the bond lengths and angles have normal values. Each asymmetric unit contains two title molecules, which are similar to each other with only slightly difference in their bond lengths and angles (Figure 1 and Table 1).

In the crystal packing the edge-to-face π–π stacking interactions were observed. The distance from the edge of the molecular plane B (N1ⁱ/C1ⁱ/C2ⁱ/C3ⁱ/C4ⁱ/C5ⁱ/C6ⁱ/C7ⁱ/C8ⁱ/C9ⁱ/ C10ⁱ/C11ⁱ/C12ⁱ)(i: 1 - x,-1/2 + y,0.5 - z) to the face of the molecular plane A(N1/C1/C2/C3/C4/C5/C6/C7/C8/C9/C10/C11/C12) is 3.538 (3) Å, and the dihedral angle between plane A and B is 62.06 (3)°. Similar relationships were observed with the molecular plane C and D. The edge-to-face distance of the molecular plane D(N3ⁱⁱ/C18ⁱⁱ/C19ⁱⁱ/C20ⁱⁱ/C21ⁱⁱ/C22ⁱⁱ/C23ⁱⁱ/ C24ⁱⁱ/C25ⁱⁱ/C26ⁱⁱ/C27ⁱⁱ/C28ⁱⁱ/C29ⁱⁱ)(ii: -x,1/2 + y,0.5 - z) to the molecular plane C(N3/C18/C19/C20/C21/C22/C23/C24/C25/C26/C27 /C28/C29) is 3.496 (3) Å, and the dihedral angle between plane C and D is 61.41 (3)° (Figure 2).Through these edge-to-face π–π stacking interactions, the neighbouring molecules form pillar structures (Figure 3).

Experimental

9-Diethylaminomethyl carbazole was prepared according to a procedure described in the literature (Gu, et al., 1997). Colorless crystals were obtained by recrystallized from ethanol at room temperature.

¹H-NMR (CDCl₃, 400 MHz) δ: 1.07 (t, 6H, 2-CH3), 2.68 (q, 4H, 2-CH2-), 4.98 (s, 2H, –CH2-), 7.22 (t, 2H, ArH), 7.44 (t, 2H, ArH), 7.54 (d, 2H, ArH), 8.06 (d, 2H, ArH).