Crystal structure of (E)-5-di­ethyl­amino-2-({[4-(di­methyl­amino)­phen­yl]imino}­meth­yl)phenol

C Vidya Rani; G Chakkaravarthi; G Rajagopal

doi:10.1107/S2056989015011779

. 2015 Jun 24;71(Pt 7):o503. doi: 10.1107/S2056989015011779

Crystal structure of (E)-5-diethylamino-2-({[4-(dimethylamino)phenyl]imino}methyl)phenol

C Vidya Rani ^a, G Chakkaravarthi ^b,^*, G Rajagopal ^a,^*

PMCID: PMC4518928 PMID: 26279932

Abstract

The title Schiff base compound, C₁₉H₂₅N₃O, is approximately planar, with a dihedral angle of 9.03 (13)° between the planes of the aromatic rings, and has an E conformation about the N=C bond. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond, with an S(6) ring motif. In the crystal, molecules are linked by C—H⋯π interactions, forming sheets parallel to the bc plane.

Keywords: crystal structure, Schiff base, intramolecular O—H⋯N hydrogen bond, C—H⋯π interactions

Related literature

For biological activities of Schiff base derivatives, see: Savaliya et al. (2010 ▸); Xu et al. (2012 ▸). For the structures of similar compounds, see: Manvizhi et al. (2011 ▸); Thirugnanasundar et al. (2011 ▸). graphic file with name e-71-0o503-scheme1.jpg

Experimental

Crystal data

C₁₉H₂₅N₃O
M _r = 311.42
Monoclinic,
a = 8.8201 (7) Å
b = 7.8850 (7) Å
c = 13.0639 (10) Å
β = 108.407 (3)°
V = 862.06 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T _min = 0.981, T _max = 0.985
13009 measured reflections
3825 independent reflections
2438 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.159
S = 1.03
3825 reflections
214 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011779/su5157sup1.cif

e-71-0o503-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011779/su5157Isup2.hkl

e-71-0o503-Isup2.hkl^{(183.7KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015011779/su5157Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015011779/su5157fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular O—H.·N hydrogen bonds is shown as a dashd lines (see Table 1 for details).

Click here for additional data file.^{(2.2MB, tif)}

a . DOI: 10.1107/S2056989015011779/su5157fig2.tif

A view along the a axis of the crystal apcking of the title compound. The O—H.·N and C-H⋯π interactions are illustrated by dashed lines (see Table 1 for details).

CCDC reference: 1407678

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

Table 1. Hydrogen-bond geometry (, ).

Cg1 and Cg2 are the centroids of rings C3C8 and C10C15, respectively.

DHA	DH	HA	D A	DHA
O1H1N2	0.82	1.85	2.585(3)	148
C11H11Cg1ⁱ	0.93	2.71	3.517(3)	145
C17H17B Cg2ⁱⁱ	0.96	2.90	3.743(5)	147

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

Acknowledgments

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

S1. Structural commentary

Schiff base derivatives are known to exhibit antimicrobial (Savaliya et al., 2010) and antibacterial (Xu et al., 2012) activities. Herein we report on the synthesis and the crystal structure of a new Schiff base compound.

The molecular structure of the title compound is illustrated in Fg. 1. The geometric parameters are comparable to those reported for similar structures (Manvizhi et al., 2011; Thirugnanasundar et al., 2011). The dihedral angle between the benzene rings (C3—C8) and (C10—C15) is 9.03 (13)°. The molecular structure is stabilized by an intramolecular O—H···N hydrogen bond (Table 1 and Fig. 1).

In the crystal, molecules are linked by C—H···π interactions forming sheets parallel to the bc plane (Table 1 and Fig. 2).

S2. Synthesis and crystallization

To an ethanol solution (10 ml) of 5-(diethylamino)-2-hydroxybenzaldehyde (96.5 mg, 0.5 mol) was added N¹,N¹-dimethylbenzene-1,4-diamine (68 mg, 0.5 mol). The mixture was stirred and 2 to 3 drops of glacial acetic acid were added. Stirring was continued for 30 mins and then the reaction mixture was refluxed for 2 h. On completion of the reaction, monitored by TLC, the mixture was allowed to cool to room temperature and the solid yellow precipitate that formed was filtered, dried, and recrystallized from DMF, giving colourless block-like crystals.

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically and refined using riding model: O—H = 0.82 Å, C—H = 0.93 - 0.97 Å with U_iso(H) = 1.5Ueq(O,C) for the hydroxyl and methyl H atoms and 1.2U_eq(C) for other H atoms. The components of the anisotropic displacement parameters of the atoms in bonds N3—C16, N3—C18 and N1—C2 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command, and the C16—C17 bond distance was restrained to 1.54 (1) Å.