N-Benzyl-isatin.

In the title compound, C(15)H(11)NO(2), two C-H⋯O hydrogen bonds are observed in the crystal structure, as well as π-π stacking with a centroid-centroid distance of 3.623 (2) Å. The planarity of the two ring systems is illustrated by very small deviations of all the atoms from these planes [largest deviations = 0.003 (3) and 0.010 (3) Å for the phenyl and fused-benzene rings, respectively]. The dihedral angle between these two planes is 77.65 (9)°.

Related literature

For literature regarding the biological properties of N-benzyl­isatin, see: Palmer et al. (1987 ▶); Goldschmidt & Llewellyn (1950 ▶); Wei et al. (2004 ▶); Frolova et al. (1988 ▶); Akkurt et al. (2006 ▶). For background regarding the functionalization of isatin, see: Schutte (2011 ▶). For a similar structure, see: Akkurt et al. (2006 ▶).

Experimental

Crystal data

C15H11NO2

M = 237.25

Monoclinic,

a = 6.5766 (5) Å

b = 4.8877 (4) Å

c = 18.2211 (13) Å

β = 98.316 (7)°

V = 579.55 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 183 K

0.34 × 0.07 × 0.02 mm

Data collection

Oxford Xcalibur Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.881, T max = 0.921

5347 measured reflections

2095 independent reflections

1264 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.128

S = 0.99

2095 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006575/ez2282sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006575/ez2282Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006575/ez2282Isup3.cml

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

C15H11NO2	F(000) = 248
Mr = 237.25	Dx = 1.36 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.5766 (5) Å	Cell parameters from 972 reflections
b = 4.8877 (4) Å	θ = 3.1–29.2°
c = 18.2211 (13) Å	µ = 0.09 mm−1
β = 98.316 (7)°	T = 183 K
V = 579.55 (8) Å3	Plate, orange
Z = 2	0.34 × 0.07 × 0.02 mm

Oxford Xcalibur Ruby CCD diffractometer	2095 independent reflections
Graphite monochromator	1264 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm-1	Rint = 0.068
ο oscillation scan	θmax = 25.3°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	h = −7→7
Tmin = 0.881, Tmax = 0.921	k = −5→5
5347 measured reflections	l = −21→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0406P)2] where P = (Fo2 + 2Fc2)/3
2095 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Experimental. CrysAlis Pro (Oxford Diffraction Ltd, 2007) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
C8	0.7610 (6)	−0.1172 (9)	0.7201 (2)	0.0419 (11)
C7	0.6174 (6)	0.0052 (8)	0.6537 (2)	0.0398 (10)
C6	0.7413 (5)	0.2130 (8)	0.6238 (2)	0.0356 (10)
C5	0.6944 (5)	0.3865 (8)	0.5635 (2)	0.0396 (10)
H5	0.5629	0.3827	0.534	0.048*
C4	0.8453 (6)	0.5654 (8)	0.5477 (2)	0.0406 (11)
H4	0.8183	0.6855	0.5065	0.049*
C3	1.0351 (6)	0.5702 (8)	0.5917 (2)	0.0395 (10)
H3	1.1357	0.6967	0.5804	0.047*
C2	1.0833 (6)	0.3952 (8)	0.6520 (2)	0.0371 (10)
H2	1.2146	0.3986	0.6815	0.045*
C1	0.9315 (5)	0.2159 (9)	0.6670 (2)	0.0339 (10)
C9	1.1290 (5)	−0.0424 (8)	0.7759 (2)	0.0395 (10)
H9A	1.2449	−0.0664	0.7473	0.047*
H9B	1.1091	−0.2179	0.8011	0.047*
C10	1.1851 (6)	0.1760 (8)	0.8340 (2)	0.0358 (10)
C11	1.3769 (6)	0.2963 (9)	0.8421 (2)	0.0456 (11)
H11	1.4729	0.2444	0.8104	0.055*
C12	1.4297 (7)	0.4925 (10)	0.8963 (3)	0.0543 (13)
H12	1.5617	0.575	0.9013	0.065*
C13	1.2940 (8)	0.5685 (9)	0.9425 (2)	0.0561 (13)
H13	1.3316	0.7019	0.9799	0.067*
C14	1.1016 (7)	0.4498 (10)	0.9345 (2)	0.0550 (12)
H14	1.0056	0.5023	0.9661	0.066*
C15	1.0489 (6)	0.2540 (8)	0.8801 (2)	0.0451 (11)
H15	0.9164	0.1727	0.8747	0.054*
N1	0.9447 (4)	0.0189 (6)	0.72476 (17)	0.0355 (9)
O1	0.7208 (4)	−0.2996 (6)	0.76148 (16)	0.0584 (9)
O2	0.4417 (4)	−0.0659 (6)	0.63438 (16)	0.0561 (9)

	U11	U22	U33	U12	U13	U23
C8	0.052 (3)	0.036 (3)	0.040 (3)	0.004 (2)	0.013 (2)	−0.007 (2)
C7	0.039 (2)	0.040 (3)	0.042 (3)	0.000 (2)	0.012 (2)	−0.012 (2)
C6	0.038 (2)	0.035 (2)	0.032 (3)	0.006 (2)	−0.0002 (19)	−0.005 (2)
C5	0.034 (2)	0.044 (3)	0.039 (3)	0.001 (2)	−0.0022 (18)	−0.009 (2)
C4	0.051 (3)	0.036 (3)	0.033 (3)	0.000 (2)	0.000 (2)	−0.001 (2)
C3	0.054 (3)	0.028 (2)	0.038 (3)	−0.001 (2)	0.013 (2)	−0.007 (2)
C2	0.046 (2)	0.035 (2)	0.031 (2)	0.004 (2)	0.0050 (18)	−0.003 (2)
C1	0.040 (2)	0.034 (2)	0.029 (2)	0.001 (2)	0.0087 (19)	−0.008 (2)
C9	0.045 (2)	0.038 (2)	0.034 (2)	0.006 (2)	0.0028 (18)	−0.001 (2)
C10	0.045 (2)	0.032 (2)	0.028 (3)	0.006 (2)	−0.0017 (19)	0.007 (2)
C11	0.045 (3)	0.046 (3)	0.043 (3)	0.004 (2)	0.000 (2)	0.003 (2)
C12	0.059 (3)	0.048 (3)	0.050 (3)	−0.002 (2)	−0.011 (2)	0.010 (3)
C13	0.084 (4)	0.044 (3)	0.035 (3)	−0.004 (3)	−0.010 (3)	−0.003 (2)
C14	0.080 (3)	0.046 (3)	0.041 (3)	0.005 (3)	0.014 (2)	−0.004 (3)
C15	0.060 (3)	0.039 (3)	0.037 (3)	−0.005 (2)	0.009 (2)	−0.001 (2)
N1	0.0379 (18)	0.036 (2)	0.032 (2)	−0.0020 (17)	0.0025 (15)	0.0040 (18)
O1	0.071 (2)	0.0487 (19)	0.058 (2)	−0.0078 (18)	0.0194 (16)	0.008 (2)
O2	0.0411 (16)	0.057 (2)	0.071 (2)	−0.0102 (16)	0.0099 (14)	−0.0093 (18)

C8—O1	1.221 (5)	C9—N1	1.449 (4)
C8—N1	1.371 (5)	C9—C10	1.511 (5)
C8—C7	1.544 (5)	C9—H9A	0.99
C7—O2	1.209 (4)	C9—H9B	0.99
C7—C6	1.457 (5)	C10—C15	1.368 (5)
C6—C1	1.379 (5)	C10—C11	1.380 (5)
C6—C5	1.386 (5)	C11—C12	1.384 (6)
C5—C4	1.384 (5)	C11—H11	0.95
C5—H5	0.95	C12—C13	1.364 (6)
C4—C3	1.382 (5)	C12—H12	0.95
C4—H4	0.95	C13—C14	1.380 (6)
C3—C2	1.392 (5)	C13—H13	0.95
C3—H3	0.95	C14—C15	1.385 (6)
C2—C1	1.385 (5)	C14—H14	0.95
C2—H2	0.95	C15—H15	0.95
C1—N1	1.420 (5)
O1—C8—N1	125.7 (4)	C10—C9—H9A	108.8
O1—C8—C7	127.2 (4)	N1—C9—H9B	108.8
N1—C8—C7	107.1 (4)	C10—C9—H9B	108.8
O2—C7—C6	130.8 (4)	H9A—C9—H9B	107.7
O2—C7—C8	124.6 (4)	C15—C10—C11	119.0 (4)
C6—C7—C8	104.6 (3)	C15—C10—C9	120.8 (4)
C1—C6—C5	121.7 (4)	C11—C10—C9	120.2 (4)
C1—C6—C7	107.7 (4)	C10—C11—C12	120.2 (4)
C5—C6—C7	130.6 (4)	C10—C11—H11	119.9
C4—C5—C6	117.9 (4)	C12—C11—H11	119.9
C4—C5—H5	121.1	C13—C12—C11	120.7 (5)
C6—C5—H5	121.1	C13—C12—H12	119.7
C3—C4—C5	120.3 (4)	C11—C12—H12	119.7
C3—C4—H4	119.8	C12—C13—C14	119.4 (4)
C5—C4—H4	119.8	C12—C13—H13	120.3
C4—C3—C2	122.0 (4)	C14—C13—H13	120.3
C4—C3—H3	119	C13—C14—C15	119.8 (4)
C2—C3—H3	119	C13—C14—H14	120.1
C1—C2—C3	117.2 (4)	C15—C14—H14	120.1
C1—C2—H2	121.4	C10—C15—C14	120.9 (4)
C3—C2—H2	121.4	C10—C15—H15	119.6
C6—C1—C2	120.9 (4)	C14—C15—H15	119.6
C6—C1—N1	111.7 (3)	C8—N1—C1	108.9 (3)
C2—C1—N1	127.4 (3)	C8—N1—C9	125.9 (3)
N1—C9—C10	113.6 (3)	C1—N1—C9	124.9 (3)
N1—C9—H9A	108.8
O1—C8—C7—O2	0.5 (6)	N1—C9—C10—C11	−124.2 (4)
N1—C8—C7—O2	−179.1 (4)	C15—C10—C11—C12	0.1 (6)
O1—C8—C7—C6	−179.8 (4)	C9—C10—C11—C12	−178.7 (4)
N1—C8—C7—C6	0.6 (4)	C10—C11—C12—C13	0.3 (6)
O2—C7—C6—C1	179.0 (4)	C11—C12—C13—C14	−0.6 (7)
C8—C7—C6—C1	−0.7 (4)	C12—C13—C14—C15	0.5 (6)
O2—C7—C6—C5	−1.2 (7)	C11—C10—C15—C14	−0.2 (6)
C8—C7—C6—C5	179.1 (4)	C9—C10—C15—C14	178.6 (4)
C1—C6—C5—C4	−0.1 (6)	C13—C14—C15—C10	0.0 (6)
C7—C6—C5—C4	−179.8 (4)	O1—C8—N1—C1	−180.0 (4)
C6—C5—C4—C3	−0.7 (6)	C7—C8—N1—C1	−0.4 (4)
C5—C4—C3—C2	1.1 (6)	O1—C8—N1—C9	5.0 (6)
C4—C3—C2—C1	−0.7 (5)	C7—C8—N1—C9	−175.4 (3)
C5—C6—C1—C2	0.4 (6)	C6—C1—N1—C8	−0.1 (4)
C7—C6—C1—C2	−179.8 (3)	C2—C1—N1—C8	−179.8 (4)
C5—C6—C1—N1	−179.3 (3)	C6—C1—N1—C9	175.0 (3)
C7—C6—C1—N1	0.5 (4)	C2—C1—N1—C9	−4.7 (6)
C3—C2—C1—C6	−0.1 (5)	C10—C9—N1—C8	−111.7 (4)
C3—C2—C1—N1	179.6 (4)	C10—C9—N1—C1	74.0 (4)
N1—C9—C10—C15	57.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.41	3.213 (5)	143
C9—H9A···O2ii	0.99	2.59	3.525 (4)	159
C9—H9B···O1	0.99	2.58	2.941 (5)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.41	3.213 (5)	143
C9—H9A⋯O2ii	0.99	2.59	3.525 (4)	159

Symmetry codes: (i) ; (ii) .