Crystal structure of 3-(3,4-di­methyl­anilino)-2-benzo­furan-1(3H)-one

Muhammad Salim; Muhammad Nawaz Tahir; Muhammad Shahid; Munawar Ali Munawar

doi:10.1107/S2056989015009299

. 2015 May 20;71(Pt 6):o413. doi: 10.1107/S2056989015009299

Crystal structure of 3-(3,4-dimethylanilino)-2-benzofuran-1(3H)-one

Muhammad Salim ^a, Muhammad Nawaz Tahir ^b,^*, Muhammad Shahid ^a, Munawar Ali Munawar ^a

PMCID: PMC4459309 PMID: 26090197

Abstract

In the title compound, C₁₆H₁₅NO₂, the 2-benzofuran-1(3H)-one and 3,4-dimethylaniline fragments are oriented with a dihedral angle of 89.12 (5)°. N—H⋯O hydrogen-bond interactions join molecules into C(6) chains propagating along the a axis. In addition, there are π–π stacking interactions between the 2-benzofuranone benzene rings [centroid–centroid distance = 3.7870 (13) Å] and C—H⋯π interactions between one of the methyl groups and the 3,4-dimethylaniline benzene ring.

Keywords: crystal structure, 2-benzofuranone, hydrogen bonding

Related literature

For related crystal structures, see: Li et al. (2009 ▸); Odabaşoğlu & Büyükgüngör (2006a ▸,b ▸, 2007a ▸,b ▸). For graph-set notation, see: Bernstein et al. (1995 ▸). graphic file with name e-71-0o413-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₅NO₂
M _r = 253.29
Orthorhombic,
a = 7.3386 (7) Å
b = 14.9133 (11) Å
c = 24.3322 (18) Å
V = 2663.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.38 × 0.23 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T _min = 0.970, T _max = 0.988
20839 measured reflections
2906 independent reflections
1660 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.144
S = 1.02
2906 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (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: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015009299/gk2634sup1.cif

e-71-0o413-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009299/gk2634Isup2.hkl

e-71-0o413-Isup2.hkl^{(159.8KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015009299/gk2634Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015009299/gk2634fig1.tif

Molecular structure with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.

Click here for additional data file.^{(1.1MB, tif)}

a via PLATON . DOI: 10.1107/S2056989015009299/gk2634fig2.tif

The chains of molecules along the a axis via N—H⋯O hydrogen bond (PLATON; Spek, 2009).

CCDC reference: 1401225

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

Table 1. Hydrogen-bond geometry (, ).

Cg3 is the centroid of the C9C14

DHA	DH	HA	D A	DHA
N1H1O2ⁱ	0.86	2.31	3.025(2)	141
C15H15B Cg3ⁱⁱ	0.96	2.88	3.661(3)	139

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

Acknowledgments

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

supplementary crystallographic information

S1. Comment

The crystal structures of 3-anilinoisobenzofuran-1(3H)-one (Odabaşoğlu & Büyükgüngör, 2006a), 3-(2,6-dimethylanilino)isobenzofuran-1(3H) -one (Odabaşoğlu & Büyükgüngör, 2006b), 3-(4-methylanilino)isobenzo furan-1(3H)-one (Odabaşoğlu & Büyükgüngör, 2007a), 3-(2- (hydroxymethyl)anilino)isobenzofuran-1(3H)-one (Odabaşoğlu & Büyükgüngör, 2007b), and 3-((3-oxo-1,3-dihydroisobenzofuran-1-yl)amino) benzoic acid Li et al., 2009) have been published which are related to the title compound (I, Fig. 1). The title compound was synthesized for the biological studies and for the preparation of further derivitives.

The benzofuran ring A (C1–C8/O1/O2) and the 3,4-dmethylaniline group B (C9–C16/N1) are planar with r. m. s. deviation of 0.0209 and 0.0101 Å, respectively. The dihedral angle between A/B fragments is 89.12 (5)°. Intermolecular hydrogen bond of N—H···O type generates C (6) chains (Bernstein et al., 1995) along the crystallographic a axis (Table 1, Fig. 2). The π–π interactions are observed between the 2-benzofuranone fragments [ Cg1—Cg2ⁱ 3.6204 (12) Å; Cg1—Cg1ⁱ 3.8138 (13) Å; Cg2—Cg2ⁱ 3.7870 (13) Å, Cg1 - centroid of C1/C2/C7/C8/O1, Cg2 - centroid of C2–C7); i = - 1/2 + x, y, 1/2 - z ]. In addition there are also C—H···π interactions (Table 1).

S2. Experimental

Equimolar quantities of 3,4-dimethylaniline (0.605 g. 5 mmol) and 2-formylbenzoic acid (0.751 g, 5 mmol) were stirred in methanol for 2 h. The solution was kept at room temperature for crystallization which afforded light brown needles after 48 h.