1-Phenyl-isatin.

In the title compound, C(14)H(9)NO(2), the phenyl ring makes a dihedral angle of 50.59 (5)° with the mean plane of the isatin fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds. The crystal structure also exhibits two slipped π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.968 (3) Å, inter-planar distance = 3.484 (3) Å and slippage = 1.899 (3) Å], and between the phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.968 (3) Å, inter-planar 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 = 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

Δρmax = 0.16 e Å−3

Δρmin = −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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811027334/lx2190Isup3.cml

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

C14H9NO2	F(000) = 464
Mr = 223.22	Dx = 1.379 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4093 reflections
a = 3.9677 (1) Å	θ = 1.0–27.5°
b = 13.3259 (4) Å	µ = 0.09 mm−1
c = 20.3397 (7) Å	T = 293 K
V = 1075.42 (6) Å3	Rods, orange
Z = 4	0.37 × 0.30 × 0.15 mm

Nonius KappaCCD diffractometer	1085 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 27.4°, θmin = 4.3°
Detector resolution: 9 pixels mm-1	h = −5→4
φ and ω scans	k = −15→17
7556 measured reflections	l = −26→25
1462 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0318P)2 + 0.1048P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1462 reflections	Δρmax = 0.16 e Å−3
155 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.3503 (5)	0.20706 (10)	0.76634 (7)	0.0522 (4)
O1	0.0729 (4)	0.36020 (10)	0.75768 (7)	0.0685 (4)
O2	0.0940 (5)	0.34979 (11)	0.90098 (7)	0.0861 (6)
C1	0.1973 (6)	0.29305 (13)	0.78955 (9)	0.0544 (5)
C2	0.2117 (6)	0.28662 (15)	0.86534 (9)	0.0589 (6)
C3	0.3830 (6)	0.19284 (13)	0.87981 (9)	0.0550 (5)
C4	0.4654 (6)	0.14811 (16)	0.93889 (10)	0.0670 (6)
H4	0.4099	0.1786	0.9786	0.080*
C5	0.6316 (7)	0.05730 (16)	0.93787 (11)	0.0714 (7)
H5	0.6891	0.0258	0.9771	0.086*
C6	0.7124 (7)	0.01328 (16)	0.87866 (11)	0.0672 (6)
H6	0.8264	−0.0477	0.8789	0.081*
C7	0.6296 (6)	0.05666 (13)	0.81841 (10)	0.0572 (5)
H7	0.6849	0.0258	0.7788	0.069*
C8	0.4628 (5)	0.14699 (13)	0.82012 (8)	0.0497 (5)
C9	0.3944 (5)	0.18304 (13)	0.69803 (8)	0.0502 (5)
C10	0.2965 (6)	0.09053 (14)	0.67389 (10)	0.0591 (6)
H10	0.2021	0.0428	0.7017	0.071*
C11	0.3406 (7)	0.06987 (17)	0.60815 (10)	0.0697 (6)
H11	0.2796	0.0074	0.5916	0.084*
C12	0.4738 (7)	0.14081 (19)	0.56704 (11)	0.0746 (7)
H12	0.5012	0.1264	0.5226	0.090*
C13	0.5670 (7)	0.23267 (17)	0.59071 (10)	0.0706 (7)
H13	0.6557	0.2806	0.5623	0.085*
C14	0.5300 (6)	0.25464 (15)	0.65666 (10)	0.0580 (6)
H14	0.5956	0.3168	0.6730	0.070*

	U11	U22	U33	U12	U13	U23
N1	0.0648 (11)	0.0426 (8)	0.0491 (8)	0.0002 (9)	0.0042 (8)	0.0007 (7)
O1	0.0824 (11)	0.0514 (7)	0.0717 (9)	0.0092 (9)	−0.0031 (9)	0.0038 (7)
O2	0.1197 (16)	0.0691 (9)	0.0694 (9)	0.0189 (12)	0.0108 (11)	−0.0142 (8)
C1	0.0609 (13)	0.0437 (9)	0.0585 (11)	−0.0030 (10)	0.0017 (10)	−0.0003 (9)
C2	0.0685 (15)	0.0513 (10)	0.0570 (11)	−0.0023 (12)	0.0054 (11)	−0.0071 (9)
C3	0.0624 (13)	0.0509 (10)	0.0516 (10)	−0.0062 (11)	0.0002 (11)	−0.0008 (9)
C4	0.0776 (17)	0.0688 (12)	0.0547 (12)	−0.0082 (13)	−0.0035 (11)	−0.0005 (10)
C5	0.0798 (18)	0.0711 (13)	0.0632 (14)	−0.0008 (15)	−0.0110 (13)	0.0132 (11)
C6	0.0685 (16)	0.0564 (11)	0.0767 (14)	0.0005 (12)	−0.0096 (13)	0.0088 (11)
C7	0.0619 (13)	0.0499 (10)	0.0598 (12)	0.0004 (11)	0.0024 (12)	−0.0010 (9)
C8	0.0538 (12)	0.0448 (9)	0.0507 (10)	−0.0079 (10)	0.0012 (9)	0.0028 (8)
C9	0.0509 (12)	0.0521 (10)	0.0477 (10)	0.0018 (10)	0.0011 (9)	0.0003 (8)
C10	0.0625 (14)	0.0527 (11)	0.0622 (13)	−0.0027 (11)	0.0032 (12)	−0.0012 (9)
C11	0.0782 (17)	0.0662 (12)	0.0646 (14)	0.0101 (14)	−0.0076 (13)	−0.0139 (11)
C12	0.0856 (19)	0.0907 (16)	0.0475 (11)	0.0272 (16)	−0.0009 (12)	−0.0046 (12)
C13	0.0742 (17)	0.0805 (15)	0.0571 (12)	0.0090 (14)	0.0097 (13)	0.0159 (11)
C14	0.0598 (14)	0.0561 (10)	0.0581 (11)	−0.0023 (11)	0.0022 (11)	0.0069 (9)

N1—C1	1.380 (2)	C6—H6	0.9300
N1—C8	1.427 (2)	C7—C8	1.374 (3)
N1—C9	1.436 (2)	C7—H7	0.9300
O1—C1	1.210 (2)	C9—C14	1.381 (3)
O2—C2	1.205 (2)	C9—C10	1.383 (3)
C1—C2	1.545 (3)	C10—C11	1.376 (3)
C2—C3	1.453 (3)	C10—H10	0.9300
C3—C4	1.381 (3)	C11—C12	1.368 (3)
C3—C8	1.395 (3)	C11—H11	0.9300
C4—C5	1.378 (3)	C12—C13	1.366 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.377 (3)	C13—C14	1.381 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.394 (3)	C14—H14	0.9300
C1—N1—C8	109.94 (15)	C6—C7—H7	121.5
C1—N1—C9	124.71 (15)	C7—C8—C3	120.98 (17)
C8—N1—C9	125.34 (15)	C7—C8—N1	128.50 (16)
O1—C1—N1	127.60 (18)	C3—C8—N1	110.52 (16)
O1—C1—C2	126.19 (18)	C14—C9—C10	120.60 (17)
N1—C1—C2	106.20 (16)	C14—C9—N1	118.86 (16)
O2—C2—C3	131.34 (19)	C10—C9—N1	120.53 (17)
O2—C2—C1	123.17 (19)	C11—C10—C9	119.18 (19)
C3—C2—C1	105.49 (16)	C11—C10—H10	120.4
C4—C3—C8	120.96 (19)	C9—C10—H10	120.4
C4—C3—C2	131.19 (19)	C12—C11—C10	120.3 (2)
C8—C3—C2	107.85 (16)	C12—C11—H11	119.8
C5—C4—C3	118.6 (2)	C10—C11—H11	119.8
C5—C4—H4	120.7	C13—C12—C11	120.5 (2)
C3—C4—H4	120.7	C13—C12—H12	119.7
C6—C5—C4	119.9 (2)	C11—C12—H12	119.7
C6—C5—H5	120.1	C12—C13—C14	120.2 (2)
C4—C5—H5	120.1	C12—C13—H13	119.9
C5—C6—C7	122.5 (2)	C14—C13—H13	119.9
C5—C6—H6	118.8	C13—C14—C9	119.12 (19)
C7—C6—H6	118.8	C13—C14—H14	120.4
C8—C7—C6	117.03 (19)	C9—C14—H14	120.4
C8—C7—H7	121.5
C8—N1—C1—O1	−179.8 (2)	C2—C3—C8—C7	179.5 (2)
C9—N1—C1—O1	1.2 (3)	C4—C3—C8—N1	179.6 (2)
C8—N1—C1—C2	−0.4 (2)	C2—C3—C8—N1	0.0 (2)
C9—N1—C1—C2	−179.38 (19)	C1—N1—C8—C7	−179.2 (2)
O1—C1—C2—O2	0.6 (4)	C9—N1—C8—C7	−0.3 (3)
N1—C1—C2—O2	−178.8 (2)	C1—N1—C8—C3	0.3 (2)
O1—C1—C2—C3	179.8 (2)	C9—N1—C8—C3	179.23 (19)
N1—C1—C2—C3	0.4 (2)	C1—N1—C9—C14	49.4 (3)
O2—C2—C3—C4	−0.6 (4)	C8—N1—C9—C14	−129.4 (2)
C1—C2—C3—C4	−179.8 (2)	C1—N1—C9—C10	−129.4 (2)
O2—C2—C3—C8	178.9 (3)	C8—N1—C9—C10	51.9 (3)
C1—C2—C3—C8	−0.3 (2)	C14—C9—C10—C11	1.0 (3)
C8—C3—C4—C5	0.6 (3)	N1—C9—C10—C11	179.7 (2)
C2—C3—C4—C5	−179.9 (2)	C9—C10—C11—C12	−1.2 (4)
C3—C4—C5—C6	0.1 (4)	C10—C11—C12—C13	0.5 (4)
C4—C5—C6—C7	−0.6 (4)	C11—C12—C13—C14	0.5 (4)
C5—C6—C7—C8	0.3 (4)	C12—C13—C14—C9	−0.7 (4)
C6—C7—C8—C3	0.4 (3)	C10—C9—C14—C13	0.0 (3)
C6—C7—C8—N1	179.8 (2)	N1—C9—C14—C13	−178.8 (2)
C4—C3—C8—C7	−0.9 (3)

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.

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

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