1-Benzyl-3-[(4-methyl-phen-yl)imino]-indolin-2-one.

In the title compound, C(22)H(18)N(2)O, the phenyl and tolyl rings make dihedral angles of 84.71 (7) and 65.11 (6)°, respectively, with the isatin group. The aromatic rings make a dihedral angle of 60.90 (8)°. The imino C=N double bond, exists in an E conformation. In the crystal, mol-ecules are linked by weak π-π stacking inter-actions [centroid-centroid distance = 3.6598 (13) Å].

Related literature

For background to isatin, its derivatives and their biological significance, see: Chazeau et al. (1992 ▶); Igosheva et al. (2004 ▶); Medvedev et al. (1996 ▶); Abele et al. (2003 ▶). For metal complexes of isatin derivatives and their biological significance, see: Rodriguez-Arguelles et al. (2004 ▶); Singh et al. (2005 ▶); Chohan et al. (2006 ▶); Adetoye et al. (2009 ▶); Ikotun et al. (2012 ▶). For N-benzyl isatin, its derivatives and biological significance, see Akkurt et al. (2006 ▶); Jarrahpour & Khalili (2007 ▶); Cao et al. (2009 ▶).

Experimental

Crystal data

C22H18N2O

M = 326.38

Monoclinic,

a = 10.174 (2) Å

b = 15.086 (4) Å

c = 11.714 (3) Å

β = 113.596 (3)°

V = 1647.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.04 × 0.02 × 0.01 mm

Data collection

Bruker SMART CCD area-detector diffractometer

18815 measured reflections

3763 independent reflections

2456 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 0.92

3763 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024506/bx2411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024506/bx2411Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024506/bx2411Isup3.cml

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

C22H18N2O	F(000) = 688
Mr = 326.38	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Melting point: 427 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.174 (2) Å	Cell parameters from 3069 reflections
b = 15.086 (4) Å	θ = 2.6–25.6°
c = 11.714 (3) Å	µ = 0.08 mm−1
β = 113.596 (3)°	T = 296 K
V = 1647.5 (7) Å3	Rectangular plate, orange
Z = 4	0.04 × 0.02 × 0.01 mm

Bruker SMART CCD area-detector diffractometer	2456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
phi and ω scans	h = −12→13
18815 measured reflections	k = −19→19
3763 independent reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
3763 reflections	Δρmax = 0.35 e Å−3
227 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (12)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
O1	0.30165 (11)	0.19312 (7)	0.89390 (10)	0.0256 (3)
N1	0.23619 (13)	0.32278 (8)	0.77977 (12)	0.0192 (3)
N2	0.06155 (13)	0.22984 (8)	0.95540 (12)	0.0195 (3)
C18	−0.15861 (16)	0.18456 (10)	0.97075 (14)	0.0221 (4)
H18A	−0.1610	0.1353	0.9223	0.027*
C19	−0.26219 (17)	0.19479 (11)	1.01801 (15)	0.0237 (4)
H19A	−0.3354	0.1531	0.9984	0.028*
C6	−0.10985 (17)	0.48946 (10)	0.72028 (14)	0.0217 (4)
H6A	−0.1886	0.5253	0.7085	0.026*
C8	0.09598 (16)	0.45662 (10)	0.67264 (14)	0.0204 (4)
H8A	0.1541	0.4694	0.6305	0.024*
C9	0.12438 (16)	0.38541 (10)	0.75280 (14)	0.0179 (3)
C11	0.43743 (16)	0.40255 (10)	0.75565 (14)	0.0197 (4)
C22	−0.04756 (17)	0.32009 (10)	1.06994 (14)	0.0226 (4)
H22A	0.0236	0.3629	1.0872	0.027*
C5	−0.08057 (16)	0.41752 (10)	0.80063 (14)	0.0203 (4)
H5A	−0.1394	0.4046	0.8421	0.024*
C10	0.34082 (17)	0.32210 (10)	0.72300 (15)	0.0233 (4)
H10A	0.2900	0.3190	0.6332	0.028*
H10B	0.3996	0.2693	0.7499	0.028*
C17	−0.05075 (16)	0.24753 (10)	0.99516 (14)	0.0192 (3)
C4	0.03861 (16)	0.36512 (10)	0.81794 (14)	0.0178 (3)
C20	−0.25950 (16)	0.26584 (10)	1.09418 (14)	0.0211 (4)
C7	−0.02307 (16)	0.50861 (10)	0.65726 (14)	0.0209 (4)
H7A	−0.0449	0.5571	0.6038	0.025*
C21	−0.15100 (17)	0.32812 (10)	1.11853 (15)	0.0236 (4)
H21A	−0.1476	0.3765	1.1688	0.028*
C3	0.09602 (16)	0.28278 (10)	0.88691 (14)	0.0182 (3)
C2	0.22451 (16)	0.25759 (10)	0.85647 (14)	0.0196 (3)
C16	0.52131 (17)	0.42307 (11)	0.87874 (15)	0.0249 (4)
H16A	0.5174	0.3873	0.9420	0.030*
C12	0.44522 (17)	0.45665 (12)	0.66264 (16)	0.0289 (4)
H12A	0.3903	0.4435	0.5795	0.035*
C13	0.53422 (18)	0.53003 (12)	0.69284 (18)	0.0339 (5)
H13A	0.5386	0.5660	0.6300	0.041*
C15	0.61098 (18)	0.49624 (12)	0.90861 (17)	0.0315 (4)
H15A	0.6676	0.5090	0.9916	0.038*
C14	0.61647 (18)	0.54999 (11)	0.81580 (18)	0.0332 (5)
H14A	0.6755	0.5997	0.8359	0.040*
C23	−0.36913 (18)	0.27314 (12)	1.15025 (16)	0.0290 (4)
H23A	−0.3515	0.3259	1.2000	0.044*
H23B	−0.3622	0.2223	1.2016	0.044*
H23C	−0.4635	0.2759	1.0848	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0239 (6)	0.0211 (6)	0.0327 (7)	0.0069 (5)	0.0122 (5)	0.0020 (5)
N1	0.0175 (7)	0.0178 (7)	0.0251 (7)	0.0009 (5)	0.0115 (6)	0.0001 (5)
N2	0.0186 (7)	0.0179 (7)	0.0218 (7)	−0.0012 (5)	0.0077 (6)	−0.0007 (6)
C18	0.0239 (9)	0.0178 (8)	0.0236 (9)	−0.0010 (7)	0.0084 (7)	−0.0019 (7)
C19	0.0185 (8)	0.0245 (9)	0.0268 (9)	−0.0041 (7)	0.0076 (7)	0.0006 (7)
C6	0.0198 (8)	0.0183 (8)	0.0271 (9)	0.0023 (7)	0.0094 (7)	−0.0022 (7)
C8	0.0205 (8)	0.0195 (8)	0.0231 (8)	−0.0037 (7)	0.0108 (7)	−0.0019 (7)
C9	0.0169 (8)	0.0146 (8)	0.0224 (8)	−0.0011 (6)	0.0080 (7)	−0.0033 (6)
C11	0.0163 (8)	0.0205 (8)	0.0259 (9)	0.0039 (6)	0.0123 (7)	0.0011 (7)
C22	0.0214 (9)	0.0208 (9)	0.0255 (9)	−0.0043 (7)	0.0091 (7)	−0.0014 (7)
C5	0.0195 (8)	0.0198 (8)	0.0241 (9)	−0.0014 (7)	0.0112 (7)	−0.0015 (7)
C10	0.0207 (9)	0.0257 (9)	0.0277 (9)	0.0017 (7)	0.0140 (7)	−0.0037 (7)
C17	0.0194 (8)	0.0183 (8)	0.0188 (8)	0.0027 (6)	0.0067 (7)	0.0041 (6)
C4	0.0172 (8)	0.0158 (8)	0.0201 (8)	−0.0019 (6)	0.0071 (7)	−0.0020 (6)
C20	0.0189 (8)	0.0239 (9)	0.0192 (8)	0.0017 (7)	0.0065 (7)	0.0027 (7)
C7	0.0240 (9)	0.0161 (8)	0.0221 (9)	−0.0008 (7)	0.0086 (7)	0.0002 (6)
C21	0.0250 (9)	0.0242 (9)	0.0224 (9)	−0.0011 (7)	0.0102 (7)	−0.0043 (7)
C3	0.0161 (8)	0.0153 (8)	0.0215 (8)	−0.0018 (6)	0.0057 (7)	−0.0027 (6)
C2	0.0187 (8)	0.0181 (8)	0.0218 (8)	−0.0018 (7)	0.0078 (7)	−0.0036 (7)
C16	0.0245 (9)	0.0267 (9)	0.0266 (9)	0.0012 (7)	0.0136 (8)	0.0030 (7)
C12	0.0179 (8)	0.0421 (11)	0.0277 (9)	0.0035 (8)	0.0102 (7)	0.0101 (8)
C13	0.0218 (9)	0.0368 (11)	0.0476 (12)	0.0062 (8)	0.0185 (9)	0.0211 (9)
C15	0.0265 (10)	0.0343 (10)	0.0362 (11)	−0.0052 (8)	0.0152 (9)	−0.0097 (8)
C14	0.0229 (9)	0.0217 (9)	0.0617 (13)	−0.0011 (7)	0.0238 (9)	−0.0011 (9)
C23	0.0250 (9)	0.0378 (10)	0.0264 (9)	−0.0001 (8)	0.0125 (8)	0.0007 (8)

O1—C2	1.2160 (18)	C22—H22A	0.9300
N1—C2	1.3690 (19)	C5—C4	1.393 (2)
N1—C9	1.4137 (19)	C5—H5A	0.9300
N1—C10	1.4636 (19)	C10—H10A	0.9700
N2—C3	1.2767 (19)	C10—H10B	0.9700
N2—C17	1.4210 (19)	C4—C3	1.469 (2)
C18—C19	1.381 (2)	C20—C21	1.389 (2)
C18—C17	1.392 (2)	C20—C23	1.508 (2)
C18—H18A	0.9300	C7—H7A	0.9300
C19—C20	1.388 (2)	C21—H21A	0.9300
C19—H19A	0.9300	C3—C2	1.534 (2)
C6—C5	1.389 (2)	C16—C15	1.385 (2)
C6—C7	1.389 (2)	C16—H16A	0.9300
C6—H6A	0.9300	C12—C13	1.383 (2)
C8—C9	1.379 (2)	C12—H12A	0.9300
C8—C7	1.393 (2)	C13—C14	1.379 (3)
C8—H8A	0.9300	C13—H13A	0.9300
C9—C4	1.404 (2)	C15—C14	1.375 (2)
C11—C16	1.385 (2)	C15—H15A	0.9300
C11—C12	1.389 (2)	C14—H14A	0.9300
C11—C10	1.511 (2)	C23—H23A	0.9600
C22—C21	1.388 (2)	C23—H23B	0.9600
C22—C17	1.394 (2)	C23—H23C	0.9600
C2—N1—C9	110.69 (13)	C5—C4—C3	133.73 (14)
C2—N1—C10	124.27 (13)	C9—C4—C3	106.64 (13)
C9—N1—C10	124.73 (13)	C19—C20—C21	117.63 (15)
C3—N2—C17	123.20 (13)	C19—C20—C23	120.58 (15)
C19—C18—C17	120.45 (15)	C21—C20—C23	121.78 (15)
C19—C18—H18A	119.8	C6—C7—C8	121.26 (15)
C17—C18—H18A	119.8	C6—C7—H7A	119.4
C18—C19—C20	121.47 (15)	C8—C7—H7A	119.4
C18—C19—H19A	119.3	C22—C21—C20	121.84 (15)
C20—C19—H19A	119.3	C22—C21—H21A	119.1
C5—C6—C7	120.88 (15)	C20—C21—H21A	119.1
C5—C6—H6A	119.6	N2—C3—C4	136.53 (14)
C7—C6—H6A	119.6	N2—C3—C2	117.71 (13)
C9—C8—C7	117.45 (14)	C4—C3—C2	105.65 (12)
C9—C8—H8A	121.3	O1—C2—N1	126.74 (15)
C7—C8—H8A	121.3	O1—C2—C3	126.97 (14)
C8—C9—C4	122.25 (14)	N1—C2—C3	106.29 (13)
C8—C9—N1	127.10 (14)	C15—C16—C11	120.69 (16)
C4—C9—N1	110.64 (13)	C15—C16—H16A	119.7
C16—C11—C12	118.72 (15)	C11—C16—H16A	119.7
C16—C11—C10	120.68 (14)	C13—C12—C11	120.44 (17)
C12—C11—C10	120.60 (15)	C13—C12—H12A	119.8
C21—C22—C17	119.70 (14)	C11—C12—H12A	119.8
C21—C22—H22A	120.1	C14—C13—C12	120.23 (16)
C17—C22—H22A	120.1	C14—C13—H13A	119.9
C6—C5—C4	118.71 (14)	C12—C13—H13A	119.9
C6—C5—H5A	120.6	C14—C15—C16	120.09 (17)
C4—C5—H5A	120.6	C14—C15—H15A	120.0
N1—C10—C11	113.38 (12)	C16—C15—H15A	120.0
N1—C10—H10A	108.9	C15—C14—C13	119.82 (17)
C11—C10—H10A	108.9	C15—C14—H14A	120.1
N1—C10—H10B	108.9	C13—C14—H14A	120.1
C11—C10—H10B	108.9	C20—C23—H23A	109.5
H10A—C10—H10B	107.7	C20—C23—H23B	109.5
C18—C17—C22	118.88 (15)	H23A—C23—H23B	109.5
C18—C17—N2	118.41 (14)	C20—C23—H23C	109.5
C22—C17—N2	122.27 (14)	H23A—C23—H23C	109.5
C5—C4—C9	119.44 (14)	H23B—C23—H23C	109.5