Crystal structure of 9-butyl-6-[2-(pyridin-4-yl)ethen­yl]carbazol-3-amine

Ping Zhang; Xiang-Yang Bai; Ting Zhang

doi:10.1107/S2056989015007975

. 2015 Apr 25;71(Pt 5):o345–o346. doi: 10.1107/S2056989015007975

Crystal structure of 9-butyl-6-[2-(pyridin-4-yl)ethenyl]carbazol-3-amine

Ping Zhang ^a, Xiang-Yang Bai ^b, Ting Zhang ^a,^*

PMCID: PMC4420045 PMID: 25995940

Abstract

The asymmetric unit of the title compound, C₂₃H₂₃N₃, consists of two molecules, A and B, with different conformations. In molecule A, the dihedral angle between the carbazole ring system (r.m.s. deviation = 0.028 Å) and the pyridine ring is 20.28 (9)° and the N—C—C—C torsion angle of the butyl side chain is −63.4 (3)°. The equivalent data for molecule B are 0.065 Å, 48.28 (11)° and 61.0 (3)°, respectively. In the crystal, the components are connected by weak N—H⋯N hydrogen bonds, generating [030] C(14) chains of alternating A and B molecules.

Keywords: crystal structure, carbazol-3-amine, hydrogen bonding

Related literature

For background to the applications of carbazoles, see: Wang et al. (2013 ▸); Feng et al. (2013 ▸); Park et al. (2015 ▸). For further synthetic details, see: Zhang et al. (2014 ▸).

Experimental

Crystal data

C₂₃H₂₃N₃
M _r = 341.44
Monoclinic,
a = 11.296 (4) Å
b = 18.719 (7) Å
c = 17.829 (7) Å
β = 95.362 (5)°
V = 3753 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
26552 measured reflections
6604 independent reflections
4780 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.166
S = 1.14
6604 reflections
471 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989015007975/hb7392sup1.cif

e-71-0o345-sup1.cif^{(31.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007975/hb7392Isup2.hkl

e-71-0o345-Isup2.hkl^{(323.2KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015007975/hb7392Isup3.cml

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S2056989015007975/hb7392fig1.tif

The molecular structure of the title compound.

CCDC reference: 1061103

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N2H2DN6	0.86	2.56	3.154(3)	128
N5H5BN3ⁱ	0.86	2.36	3.163(3)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

We gratefully acknowledge the Natural Science Foundation of Anhui Province (grant No. 1508085QB41) for supporting this study.

supplementary crystallographic information

S1. Comment

The title compound is a carbazole derivative with an amine group and a pyridine group. Carbazole is usually utilized in organic functional materials due to it is a large conjugated system with prominent hole-transporting(Wang et al., 2013). The pyridine group havebeen used as heavy metal sensors (Feng et al., 2013) and the amino groupcan be regulated by acid-base based on intermolecular charge transfer(Park et al., 2015). The title compound might be able to get multiple application fields.

In (I) (Fig.1),

The bond distances of C15—N2 is not equal to the bond distance of C31—N5, which are 1.403 Å and 1.395 Å. The torsion angle of C8–C17—C18–C19 are similiar to C36–C40—C41–C42, but the dihedral angles of the phenyl group and pyridine group is different in the two molecular, which are 18.97° and 45.44°, respectively.

The crystal packing shows that the related molecules are linking by N6···H2D—N2, N5···H16—C16 hydrogen bonds.