4-(Dimethyl­amino)benzaldehyde

Bo Gao; Jian-Liang Zhu

doi:10.1107/S160053680801581X

. 2008 Jun 7;64(Pt 7):o1182. doi: 10.1107/S160053680801581X

4-(Dimethylamino)benzaldehyde

Bo Gao ^a,^*, Jian-Liang Zhu ^a

PMCID: PMC2961670 PMID: 21202825

Abstract

The title compound, C₉H₁₁NO, crystallizes with two independent but essentially identical molecules in the asymmetric unit, which are linked via a C—H⋯π interaction. In both molecules, the aldehyde and dimethylamine groups are essentially coplanar with the attached benzene ring. In the crystal structure, C—H⋯O hydrogen bonds link one type of independent molecules into a chain along the a axis. In addition, the structure is stabilized by π–π stacking interactions involving the benzene rings [centroid-to-centroid distance = 3.697 (2) Å].

Related literature

For synthesis, see: Wu & Zhou (2005 ▶). For general background, see: Kawski et al. (2007 ▶). For related structures, see: Reffner & McCrone (1959 ▶); Dattagupta & Saha (1973 ▶); Herbstein et al. (1984 ▶); Mahadevan et al. (1982 ▶); Habibi et al. (2007 ▶).

Experimental

Crystal data

C₉H₁₁NO
M _r = 149.19
Monoclinic,
a = 10.356 (6) Å
b = 7.686 (4) Å
c = 20.8434 (13) Å
β = 96.808 (13)°
V = 1647.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 123 (2) K
0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.979, T _max = 0.981
9835 measured reflections
2869 independent reflections
1826 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.160
S = 1.01
2869 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablocks I, global. DOI: 10.1107/S160053680801581X/ci2602sup1.cif

e-64-o1182-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801581X/ci2602Isup2.hkl

e-64-o1182-Isup2.hkl^{(138KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1ⁱ	0.96	2.57	3.459 (3)	155
C3—H3⋯Cg1	0.93	2.78	3.593 (3)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Zhejiang Institute of Communications, People’s Republic of China, for financial support.

supplementary crystallographic information

Comment

4-Dimethylaminobenzaldehyde (DMABA) is an important intermediate of dyes and medicine. It belongs to the same family as 4-(dimethylamino)benzonitrile (DMABN) which exhibits dual fluorescence and was a subject of extensive investigations (Kawski et al., 2007). Although the unit-cell parameters of DMABA have been reported (Reffner & McCrone, 1959), to our knowledge there is no report on the crystal structure of DMABA. The crystal structures of DMABA hydrobromide (Dattagupta & Saha, 1973), a 1:1 complex in which DMABA acts as a guest molecule in channels (Herbstein et al., 1984), a tin complex in which DMABA serves as a ligand coordinating through its O atom (Mahadevan et al., 1982), and of a 1:1 cocrystal of DMABA and 6-phenyl-1,3,5-triazine-2,4-diamine (Habibi et al., 2007) have been reported. We report here the crystal structure of the title compound.

The title compound crystallizes with two independent but essentially identical molecules in the asymmetric unit (Fig. 1). In both molecules, the aldehyde and dimethylamino groups are essentially coplanar with the attached benzene ring, similar to those observed in above crystal structures. The mean planes through the non-hydrogen atoms of two independent molecules form a dihedral angle of 76.42 (5)°. The two independent molecules are linked via a C—H···π interaction involving the C3—H3 group and C11–C16 benzene ring (Table 1).

In the crystal structure, C—H···O hydrogen bonds (Table 1) link one type of independent molecules into a chain along the a axis. In addition, the structure is stabilized by stacking interactions between the inversion related C11–C16 benzene rings [centroid–centroid distance is 3.697 (2) Å].

Experimental

The title compound was prepared according to the literature method (Wu & Zhou, 2005). Crystals suitable for X-ray analysis were obtained by slow evaporation of a isoproanol solution at room temperature (m.p. 343–347 K).