1-Phenyl­isatin

Deepak Shukla; Manju Rajeswaran

doi:10.1107/S1600536811027334

. 2011 Jul 13;67(Pt 8):o2034. doi: 10.1107/S1600536811027334

1-Phenylisatin

Deepak Shukla ^a, Manju Rajeswaran ^a,^*

PMCID: PMC3213483 PMID: 22091062

Abstract

In the title compound, C₁₄H₉NO₂, the phenyl ring makes a dihedral angle of 50.59 (5)° with the mean plane of the isatin fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds. The crystal structure also exhibits two slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.968 (3) Å, interplanar distance = 3.484 (3) Å and slippage = 1.899 (3) Å], and between the phenyl rings of neighbouring molecules [centroid–centroid distance = 3.968 (3) Å, interplanar distance = 3.638 (3) Å and slippage = 1.584 (3) Å].

Related literature

For the pharmacological properties of isatin derivatives, see: Prakash et al. (2010 ▶). For C—C bond lengths in dikotone moieties, see: Rathna & Chandrasekhar, (1991 ▶).

Experimental

Crystal data

C₁₄H₉NO₂
M _r = 223.22
Orthorhombic,
a = 3.9677 (1) Å
b = 13.3259 (4) Å
c = 20.3397 (7) Å
V = 1075.42 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.37 × 0.30 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer
7556 measured reflections
1462 independent reflections
1085 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.081
S = 1.06
1462 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL, Mercury (Allen et al., 2004 ▶) and DIAMOND (Brandenburg, 1998 ▶)’; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027334/lx2190sup1.cif

e-67-o2034-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027334/lx2190Isup2.hkl

e-67-o2034-Isup2.hkl^{(72.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811027334/lx2190Isup3.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
C4—H4⋯O2ⁱ	0.93	2.58	3.297 (3)	134
C7—H7⋯O1ⁱⁱ	0.93	2.52	3.262 (2)	137
C11—H11⋯O2ⁱⁱⁱ	0.93	2.58	3.407 (3)	149

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

supplementary crystallographic information

Comment

Isatin is a commercially available indole derivative. Isatin derivatives are well known for their pharmacological properties such as anticonvulsant activity (Prakash et al., 2010). We report herein the crystal structure of the title compound.

In the title compound (Fig. 1), the isatin unit is essentially planar, with a mean deviation of 0.004 (2) Å from the least–squares plane defined by the nine constituent atoms. The phenyl ring makes a dihedral angle of 50.59 (5)° with the mean plane of the isatin fragment. The observed C—C bond length of 1.547 (3) Å in diketo moiety is slightly longer than normal C—C bond length (Rathna & Chandrasekhar, 1991). The crystal packing (Fig. 2) is stabilized by three weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the carbonyl unit (Table 1; C4—H4···O2ⁱ), the second one between a benzene H atom and the O atom of the carbonyl unit (Table 1; C7—H7···O1ⁱⁱ), and the third one between a phenyl H atom and the O atom of the carbonyl unit (Table 1; C11—H11···O2ⁱⁱⁱ).

The crystal packing (Fig. 3) is further stabilized by two weak slipped π···π interactions (Fig. 4); the first one between the benzene rings of neighbouring molecules, with a Cg1···Cg1ⁱ distance of 3.968 (3) Å and an interplanar distance of 3.484 (3) Å resulting in a slippage of 1.899 (3) Å (Cg1 is the centroid of the C3–C8 benzene ring), and the second one between the phenyl rings of neighbouring molecules, with a Cg2···Cg2ⁱdistance of 3.968 (3) Å and an interplanar distance of 3.638 (3) Å resulting in a slippage of 1.584 (3) Å (Cg2 is the centroid of the C9–C14 phenyl ring)

Experimental

The title compound, 1–phenylisatin, was purchased from Aldrich Chemical Co.. Single crystals suitable for X—ray diffraction were obtained by sublimation under reduced pressure.