N-[(E)-1,3-Benzodioxol-5-yl­methyl­idene]-4-methyl­aniline

M Nawaz Tahir; Hazoor Ahmad Shad; Muhammad Naeem Khan; Riaz H Tariq

doi:10.1107/S1600536810048038

. 2010 Nov 24;66(Pt 12):o3293. doi: 10.1107/S1600536810048038

N-[(E)-1,3-Benzodioxol-5-ylmethylidene]-4-methylaniline

M Nawaz Tahir ^a,^*, Hazoor Ahmad Shad ^b, Muhammad Naeem Khan ^c, Riaz H Tariq ^d

PMCID: PMC3011519 PMID: 21589572

Abstract

The two symmetry-independent molecules in the asymmetric unit of the title compound, C₁₅H₁₃NO₂, differ in conformation, with the virtually planar 4-methylaniline (r.m.s. deviations of 0.0511 and 0.0082 Å) and piperonal groups (r.m.s. deviations of 0.0241 and 0.0486 Å) forming dihedral angles of 19.40 (5) and 42.90 (6)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯π interactions. The H atoms of the two methyl groups are disordered over two sets of sites of equal occupancy.

Related literature

For background to our ongoing project on the synthesis of various Schiff bases of piperonal and then their metal complexation and for a related structure, see: Tahir et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₃NO₂
M _r = 239.26
Triclinic,
a = 10.6914 (4) Å
b = 10.7680 (3) Å
c = 13.3332 (5) Å
α = 89.443 (2)°
β = 67.112 (2)°
γ = 62.534 (1)°
V = 1227.41 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.988
18069 measured reflections
4417 independent reflections
3294 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.110
S = 1.03
4417 reflections
323 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048038/gk2324sup1.cif

e-66-o3293-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048038/gk2324Isup2.hkl

e-66-o3293-Isup2.hkl^{(212KB, hkl)}

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

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

Cg3, Cg5 and Cg6 are the centroids of the C9–C14, C16–C21 and C24–C29 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯O2ⁱ	0.93	2.59	3.447 (2)	153
C17—H17⋯Cg3ⁱⁱ	0.93	2.73	3.5306 (16)	145
C22—H22B⋯Cg5ⁱⁱ	0.96	2.86	3.5480 (18)	130
C22—H22D⋯Cg5ⁱⁱ	0.96	2.71	3.5480 (18)	146
C22—H22E⋯Cg6ⁱⁱⁱ	0.96	2.91	3.8610 (18)	169

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is being reported as a part of our ongoing project related to synthesis of various Schiff bases of piperonal and then their metal complexation (Tahir et al., 2010).

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, 4-methylanilinic group A (C1—C7/N1) and the piperonalic group B (C8—C15/O1/O2) are almost planar with r. m. s deviation of 0.0511 and 0.0241 Å, respectively. The dihedral angle between A/B is 42.90 (6)°. In second molecule, the 4-methylanilinic group C (C16—C22/N2) and the piperonalic group D (C23—C30/O3/O4) are also almost planar with r. m. s deviation of 0.0082 and 0.0486 Å, respectively. The dihedral angle between C/D is 19.40 (5)°. The molecules are interlinked through hydrogen bonds of C—H···O type (Table 1, Fig. 2). The C—H···π interactions (Table 1) play important role in consolidating the crystal packing. The H atoms of methyl groups are disordered over two set of sites with equal occupancy ratio.

Experimental

Equimolar quantities of 4-methylaniline and and piperonal were refluxed in methanol along with few drops of acetic acid as catalyst for 30 min resulting in orange yellow solution. The solution was kept at room temperature which affoarded orange yellow prisms after a week.