4-(Dimethyl­amino)­benzaldehyde–2,4-di­nitro­aniline (1/1)

Ruitao Zhu; Haoyang Li; Yuewen Zhang

doi:10.1107/S160053681102232X

. 2011 Jun 18;67(Pt 7):o1676. doi: 10.1107/S160053681102232X

4-(Dimethylamino)benzaldehyde–2,4-dinitroaniline (1/1)

Ruitao Zhu ^a, Haoyang Li ^a, Yuewen Zhang ^a,^*

PMCID: PMC3152079 PMID: 21837075

Abstract

The asymmetric unit of the title compound, C₉H₁₁NO·C₆H₅N₃O₄, contains two independent molecules each of 4-(dimethylamino)benzaldehyde and 2,4-dinitroaniline. In the crystal, the components are linked by intermolecular N—H⋯O hydrogen bonds to form one-dimensional chains along [10 Inline graphic ]. Intramolecular N—H⋯O hydrogen bonds are also present.

Related literature

For related structures, see: Nesterov et al. (2000 ▶); Weber & Sheldrick (1981 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₉H₁₁NO·C₆H₅N₃O₄
M _r = 332.32
Monoclinic,
a = 18.7512 (18) Å
b = 7.3182 (6) Å
c = 24.338 (2) Å
β = 109.493 (1)°
V = 3148.4 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.48 × 0.18 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.950, T _max = 0.988
15396 measured reflections
5547 independent reflections
2303 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.087
S = 1.02
5547 reflections
433 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102232X/lh5267sup1.cif

e-67-o1676-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102232X/lh5267Isup2.hkl

e-67-o1676-Isup2.hkl^{(271.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102232X/lh5267Isup3.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
N1—H1A⋯O10ⁱ	0.86	2.18	3.010 (3)	163
N1—H1B⋯O1	0.86	2.03	2.640 (3)	127
N1—H1B⋯O7ⁱⁱ	0.86	2.49	3.170 (3)	136
N4—H4A⋯O9ⁱⁱⁱ	0.86	2.04	2.889 (3)	171
N4—H4B⋯O5	0.86	2.02	2.636 (3)	128
N4—H4B⋯O3ⁱⁱⁱ	0.86	2.42	3.047 (3)	130

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors gratefully acknowledge the University Technology Development Project in Shanxi Province (grant Nos. 20091144 and 20101116).

supplementary crystallographic information

Comment

The crystal structures of some molecular complexes of 2,4-dinitroaniline have already been published (Nesterov et al., 2000; Weber & Sheldrick, 1981). In this paper, we present the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are normal . The asymmetric unit contains two independent molecules of 4-(dimethylamino)benzaldehyde and two indpendent molecules of 2,4-Dinitroaniline. In the crystal, the components are linked by intermolecular N—H···O hydrogen bonds to form one-dimensional chains along [101].

Experimental

A mixture of 4-(dimethylamino)benzaldehyde (0.75 g, 5 mmol) and 2,4-dinitroaniline (0.92 g, 5 mmol) were refluxed in ethanol (50 ml) for 30 min and rotary evaporated. Recrystallization from ethanol solution produced the crystals of the title compound.