5-Chloro-1-(4-meth-oxy-benz-yl)indoline-2,3-dione.

In the title compound, C(16)H(12)ClNO(3), an arm-like 4-meth-oxy-benzene links to 5-chloro-indoline-2,3-dione through a methyl-ene group, with a dihedral angle between the mean planes of the benzene ring and the indole moiety of 88.44 (8)°. In the crystal, weak inter-molecular C-H⋯O and π-π stacking inter-actions [centroid-centroid distance = 3.383 (3) Å] link the mol-ecules together to form a three-dimensional framework.

Related literature

For the anti­tumor activity of N-benzyl isatin analogs, see: Vine et al. (2007 ▶); Matesic et al. (2008 ▶); Penthala et al. (2010 ▶). For the preparation of the title compound, see: Itoh et al. (2009 ▶).

Experimental

Crystal data

C16H12ClNO3

M = 301.72

Orthorhombic,

a = 7.5318 (17) Å

b = 16.587 (4) Å

c = 11.220 (3) Å

V = 1401.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.30 × 0.22 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

7665 measured reflections

3259 independent reflections

2113 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.091

S = 1.01

3259 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1514 Friedel pairs

Flack parameter: −0.01 (7)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052876/zq2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052876/zq2080Isup2.hkl

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

C16H12ClNO3	Z = 4
Mr = 301.72	F(000) = 624
Orthorhombic, Pna21	Dx = 1.430 Mg m−3Dm = 1.430 Mg m−3Dm measured by not measured
Hall symbol: P 2c -2n	Mo Kα radiation, λ = 0.71073 Å
a = 7.5318 (17) Å	µ = 0.28 mm−1
b = 16.587 (4) Å	T = 296 K
c = 11.220 (3) Å	Block, red
V = 1401.7 (6) Å3	0.30 × 0.22 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	2113 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 27.9°, θmin = 2.2°
φ and ω scans	h = −9→6
7665 measured reflections	k = −21→21
3259 independent reflections	l = −14→14

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.0529P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3259 reflections	Δρmax = 0.11 e Å−3
190 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 1514 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (7)

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
Cl1	0.68342 (11)	0.09999 (5)	0.75885 (8)	0.0978 (3)
O1	1.0165 (3)	0.41051 (12)	0.32537 (18)	0.0858 (6)
O2	1.0012 (3)	0.23283 (12)	0.33272 (17)	0.0861 (6)
O3	0.1766 (2)	0.61539 (11)	0.48186 (16)	0.0694 (5)
N1	0.8772 (3)	0.39659 (11)	0.50677 (17)	0.0571 (5)
C1	0.4538 (4)	0.61020 (13)	0.5928 (2)	0.0611 (7)
H1A	0.4197	0.6518	0.6435	0.073*
C2	0.3403 (3)	0.58404 (13)	0.5057 (2)	0.0542 (6)
C3	0.3907 (3)	0.52070 (13)	0.4320 (2)	0.0573 (6)
H3A	0.3127	0.5014	0.3745	0.069*
C4	0.5565 (3)	0.48649 (13)	0.4443 (2)	0.0545 (6)
H4A	0.5903	0.4448	0.3937	0.065*
C5	0.6734 (3)	0.51321 (13)	0.5309 (2)	0.0528 (6)
C6	0.6183 (4)	0.57500 (13)	0.6055 (2)	0.0600 (6)
H6A	0.6940	0.5930	0.6653	0.072*
C7	0.8599 (3)	0.48135 (14)	0.5399 (2)	0.0656 (7)
H7A	0.9362	0.5133	0.4887	0.079*
H7B	0.9012	0.4881	0.6212	0.079*
C8	0.9424 (3)	0.27675 (16)	0.4091 (2)	0.0619 (6)
C9	0.9526 (3)	0.37002 (16)	0.4045 (2)	0.0624 (6)
C10	0.8176 (3)	0.33139 (13)	0.5770 (2)	0.0489 (5)
C11	0.8551 (3)	0.25832 (13)	0.52206 (19)	0.0515 (5)
C12	0.7381 (3)	0.33395 (14)	0.6865 (2)	0.0585 (6)
H12A	0.7128	0.3829	0.7232	0.070*
C13	0.6964 (3)	0.26183 (16)	0.7410 (2)	0.0619 (6)
H13A	0.6416	0.2621	0.8153	0.074*
C14	0.7354 (3)	0.18880 (15)	0.6861 (2)	0.0611 (6)
C15	0.8143 (3)	0.18620 (13)	0.5764 (2)	0.0588 (6)
H15A	0.8396	0.1373	0.5397	0.071*
C16	0.1141 (4)	0.67967 (17)	0.5534 (3)	0.0917 (10)
H16A	−0.0019	0.6956	0.5268	0.138*
H16B	0.1939	0.7246	0.5470	0.138*
H16C	0.1078	0.6625	0.6350	0.138*

	U11	U22	U33	U12	U13	U23
Cl1	0.1025 (6)	0.0832 (5)	0.1078 (6)	−0.0071 (4)	−0.0163 (5)	0.0446 (5)
O1	0.0912 (14)	0.0996 (15)	0.0667 (12)	−0.0161 (12)	0.0144 (11)	0.0145 (11)
O2	0.0987 (15)	0.0962 (14)	0.0634 (11)	0.0152 (12)	0.0085 (11)	−0.0211 (11)
O3	0.0674 (12)	0.0639 (11)	0.0768 (12)	0.0064 (9)	−0.0015 (9)	−0.0028 (9)
N1	0.0626 (12)	0.0543 (12)	0.0542 (12)	−0.0024 (9)	0.0045 (10)	−0.0012 (9)
C1	0.0826 (19)	0.0469 (12)	0.0538 (15)	0.0005 (13)	0.0015 (13)	−0.0052 (11)
C2	0.0622 (15)	0.0478 (13)	0.0528 (14)	−0.0045 (11)	0.0026 (13)	0.0042 (10)
C3	0.0680 (16)	0.0484 (13)	0.0555 (15)	−0.0070 (12)	−0.0092 (13)	−0.0014 (11)
C4	0.0656 (16)	0.0463 (13)	0.0516 (14)	−0.0069 (12)	0.0003 (12)	−0.0040 (10)
C5	0.0626 (15)	0.0420 (11)	0.0536 (13)	−0.0073 (11)	−0.0012 (12)	0.0035 (10)
C6	0.0775 (18)	0.0508 (13)	0.0515 (14)	−0.0073 (13)	−0.0070 (12)	−0.0052 (11)
C7	0.0719 (17)	0.0473 (13)	0.0775 (18)	−0.0101 (12)	−0.0107 (14)	−0.0034 (12)
C8	0.0628 (16)	0.0724 (16)	0.0504 (14)	0.0086 (13)	−0.0054 (12)	−0.0097 (13)
C9	0.0605 (16)	0.0754 (16)	0.0513 (14)	−0.0047 (13)	0.0019 (13)	0.0033 (14)
C10	0.0485 (12)	0.0515 (12)	0.0468 (12)	0.0001 (11)	−0.0045 (10)	−0.0013 (11)
C11	0.0510 (12)	0.0551 (13)	0.0482 (13)	0.0033 (10)	−0.0085 (11)	−0.0051 (11)
C12	0.0649 (15)	0.0583 (14)	0.0522 (14)	−0.0016 (12)	0.0009 (12)	−0.0101 (11)
C13	0.0601 (15)	0.0795 (17)	0.0460 (13)	−0.0036 (13)	−0.0033 (12)	0.0020 (13)
C14	0.0565 (15)	0.0637 (15)	0.0630 (16)	−0.0028 (12)	−0.0136 (13)	0.0138 (13)
C15	0.0588 (15)	0.0506 (13)	0.0669 (16)	0.0049 (11)	−0.0166 (13)	−0.0035 (12)
C16	0.087 (2)	0.088 (2)	0.100 (2)	0.0183 (17)	0.0142 (18)	−0.0122 (18)

Cl1—C14	1.729 (2)	C6—H6A	0.9300
O1—C9	1.213 (3)	C7—H7A	0.9700
O2—C8	1.208 (3)	C7—H7B	0.9700
O3—C2	1.364 (3)	C8—C11	1.461 (3)
O3—C16	1.415 (3)	C8—C9	1.550 (4)
N1—C9	1.354 (3)	C10—C12	1.367 (3)
N1—C10	1.412 (3)	C10—C11	1.389 (3)
N1—C7	1.460 (3)	C11—C15	1.378 (3)
C1—C2	1.369 (3)	C12—C13	1.380 (3)
C1—C6	1.378 (3)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.391 (3)
C2—C3	1.390 (3)	C13—H13A	0.9300
C3—C4	1.379 (3)	C14—C15	1.367 (4)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.384 (3)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.386 (3)	C16—H16C	0.9600
C5—C7	1.504 (3)
C2—O3—C16	118.5 (2)	O2—C8—C9	124.1 (2)
C9—N1—C10	110.92 (18)	C11—C8—C9	105.0 (2)
C9—N1—C7	124.5 (2)	O1—C9—N1	127.4 (2)
C10—N1—C7	124.6 (2)	O1—C9—C8	126.6 (2)
C2—C1—C6	120.1 (2)	N1—C9—C8	106.1 (2)
C2—C1—H1A	120.0	C12—C10—C11	121.0 (2)
C6—C1—H1A	120.0	C12—C10—N1	128.1 (2)
O3—C2—C1	125.7 (2)	C11—C10—N1	110.85 (19)
O3—C2—C3	114.8 (2)	C15—C11—C10	121.0 (2)
C1—C2—C3	119.6 (2)	C15—C11—C8	131.8 (2)
C4—C3—C2	119.9 (2)	C10—C11—C8	107.1 (2)
C4—C3—H3A	120.0	C10—C12—C13	118.1 (2)
C2—C3—H3A	120.0	C10—C12—H12A	121.0
C3—C4—C5	121.0 (2)	C13—C12—H12A	121.0
C3—C4—H4A	119.5	C12—C13—C14	120.7 (2)
C5—C4—H4A	119.5	C12—C13—H13A	119.6
C4—C5—C6	118.1 (2)	C14—C13—H13A	119.6
C4—C5—C7	121.9 (2)	C15—C14—C13	121.2 (2)
C6—C5—C7	119.9 (2)	C15—C14—Cl1	119.8 (2)
C1—C6—C5	121.3 (2)	C13—C14—Cl1	119.0 (2)
C1—C6—H6A	119.3	C14—C15—C11	117.9 (2)
C5—C6—H6A	119.3	C14—C15—H15A	121.0
N1—C7—C5	113.85 (19)	C11—C15—H15A	121.0
N1—C7—H7A	108.8	O3—C16—H16A	109.5
C5—C7—H7A	108.8	O3—C16—H16B	109.5
N1—C7—H7B	108.8	H16A—C16—H16B	109.5
C5—C7—H7B	108.8	O3—C16—H16C	109.5
H7A—C7—H7B	107.7	H16A—C16—H16C	109.5
O2—C8—C11	130.8 (2)	H16B—C16—H16C	109.5
C16—O3—C2—C1	−1.2 (3)	C11—C8—C9—N1	0.1 (3)
C16—O3—C2—C3	179.4 (2)	C9—N1—C10—C12	178.7 (2)
C6—C1—C2—O3	−178.0 (2)	C7—N1—C10—C12	−1.2 (4)
C6—C1—C2—C3	1.4 (3)	C9—N1—C10—C11	0.7 (3)
O3—C2—C3—C4	177.2 (2)	C7—N1—C10—C11	−179.2 (2)
C1—C2—C3—C4	−2.2 (3)	C12—C10—C11—C15	−0.4 (3)
C2—C3—C4—C5	1.3 (3)	N1—C10—C11—C15	177.8 (2)
C3—C4—C5—C6	0.5 (3)	C12—C10—C11—C8	−178.8 (2)
C3—C4—C5—C7	−175.1 (2)	N1—C10—C11—C8	−0.6 (2)
C2—C1—C6—C5	0.4 (3)	O2—C8—C11—C15	0.5 (5)
C4—C5—C6—C1	−1.3 (3)	C9—C8—C11—C15	−177.9 (2)
C7—C5—C6—C1	174.4 (2)	O2—C8—C11—C10	178.7 (3)
C9—N1—C7—C5	107.0 (3)	C9—C8—C11—C10	0.3 (2)
C10—N1—C7—C5	−73.1 (3)	C11—C10—C12—C13	0.1 (3)
C4—C5—C7—N1	−33.9 (3)	N1—C10—C12—C13	−177.7 (2)
C6—C5—C7—N1	150.6 (2)	C10—C12—C13—C14	0.4 (3)
C10—N1—C9—O1	179.9 (2)	C12—C13—C14—C15	−0.6 (4)
C7—N1—C9—O1	−0.1 (4)	C12—C13—C14—Cl1	179.08 (19)
C10—N1—C9—C8	−0.5 (3)	C13—C14—C15—C11	0.4 (3)
C7—N1—C9—C8	179.5 (2)	Cl1—C14—C15—C11	−179.33 (18)
O2—C8—C9—O1	1.2 (4)	C10—C11—C15—C14	0.1 (3)
C11—C8—C9—O1	179.7 (2)	C8—C11—C15—C14	178.0 (2)
O2—C8—C9—N1	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O1i	0.96	2.63	3.537 (4)	159
C1—H1A···O2ii	0.93	2.58	3.391 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O1i	0.96	2.63	3.537 (4)	159
C1—H1A⋯O2ii	0.93	2.58	3.391 (3)	146

Symmetry codes: (i) ; (ii) .