1-Benzyl-6-chloro-indoline-2,3-dione.

In the title compound, C(15)H(10)ClNO(2),the dihedral angle between the mean planes of the benzene and 6-chloro-indoline-2,3-dione ring systems, linked through a methyl-ene group, is 81.68 (10)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, generating C(6) chains propagating in [010].

Related literature

For general background to isatin derivatives, see: Vine et al. (2007 ▶); Matesic et al. (2008 ▶). For further synthetic details, see: Bouhfid et al. (2005 ▶).

Experimental

Crystal data

C15H10ClNO2

M = 271.69

Triclinic,

a = 7.1870 (14) Å

b = 7.5800 (15) Å

c = 12.012 (2) Å

α = 80.24 (3)°

β = 84.90 (3)°

γ = 79.74 (3)°

V = 633.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.916, T max = 0.971

2520 measured reflections

2322 independent reflections

1837 reflections with I > 2σ(I)

R int = 0.015

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.155

S = 1.00

2322 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048665/hb6512sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048665/hb6512Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048665/hb6512Isup3.cml

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

C15H10ClNO2	Z = 2
Mr = 271.69	F(000) = 280
Triclinic, P1	Dx = 1.424 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1870 (14) Å	Cell parameters from 25 reflections
b = 7.5800 (15) Å	θ = 10–13°
c = 12.012 (2) Å	µ = 0.30 mm−1
α = 80.24 (3)°	T = 293 K
β = 84.90 (3)°	Block, yellow
γ = 79.74 (3)°	0.30 × 0.20 × 0.10 mm
V = 633.4 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1837 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
graphite	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −8→9
Tmin = 0.916, Tmax = 0.971	l = −14→14
2520 measured reflections	3 standard reflections every 200 reflections
2322 independent reflections	intensity decay: 1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
2322 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

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
Cl	0.15893 (11)	0.74198 (12)	0.63411 (6)	0.0780 (3)
N	0.3532 (3)	0.5031 (3)	0.25370 (16)	0.0484 (5)
O1	0.3966 (3)	0.0350 (3)	0.3312 (2)	0.0835 (7)
C1	0.0178 (3)	0.6495 (3)	0.1103 (2)	0.0534 (6)
H1A	0.0667	0.5310	0.0999	0.064*
O2	0.4404 (3)	0.3028 (3)	0.12621 (18)	0.0805 (7)
C2	−0.1670 (4)	0.7221 (4)	0.0844 (2)	0.0599 (7)
H2A	−0.2413	0.6526	0.0567	0.072*
C3	−0.2404 (4)	0.8970 (4)	0.0998 (2)	0.0608 (7)
H3A	−0.3644	0.9461	0.0823	0.073*
C4	−0.1308 (4)	0.9994 (4)	0.1409 (2)	0.0640 (7)
H4A	−0.1809	1.1177	0.1515	0.077*
C5	0.0548 (4)	0.9268 (3)	0.1666 (2)	0.0562 (6)
H5A	0.1283	0.9973	0.1942	0.067*
C6	0.1314 (3)	0.7513 (3)	0.15178 (18)	0.0446 (5)
C7	0.3348 (3)	0.6736 (3)	0.1755 (2)	0.0514 (6)
H7A	0.4057	0.6538	0.1049	0.062*
H7B	0.3896	0.7609	0.2071	0.062*
C8	0.3061 (3)	0.4880 (3)	0.37094 (19)	0.0432 (5)
C9	0.2568 (3)	0.6255 (3)	0.4348 (2)	0.0477 (6)
H9A	0.2489	0.7470	0.4027	0.057*
C10	0.2197 (3)	0.5730 (4)	0.5496 (2)	0.0528 (6)
C11	0.2296 (4)	0.3939 (4)	0.6003 (2)	0.0634 (7)
H11A	0.2030	0.3650	0.6778	0.076*
C12	0.2797 (4)	0.2591 (4)	0.5343 (3)	0.0622 (7)
H12A	0.2875	0.1378	0.5668	0.075*
C13	0.3180 (3)	0.3053 (3)	0.4202 (2)	0.0502 (6)
C14	0.3748 (3)	0.1993 (3)	0.3277 (2)	0.0582 (7)
C15	0.3958 (3)	0.3341 (3)	0.2226 (2)	0.0569 (7)

	U11	U22	U33	U12	U13	U23
Cl	0.0726 (5)	0.1012 (7)	0.0686 (5)	−0.0153 (4)	0.0032 (4)	−0.0405 (4)
N	0.0482 (11)	0.0473 (11)	0.0489 (11)	0.0000 (8)	−0.0083 (9)	−0.0108 (8)
O1	0.0867 (15)	0.0451 (11)	0.1232 (19)	0.0015 (10)	−0.0367 (13)	−0.0231 (11)
C1	0.0524 (14)	0.0538 (14)	0.0537 (14)	−0.0048 (11)	−0.0034 (11)	−0.0114 (11)
O2	0.0847 (14)	0.0836 (15)	0.0721 (14)	0.0207 (11)	−0.0193 (11)	−0.0381 (11)
C2	0.0532 (15)	0.0760 (18)	0.0523 (15)	−0.0125 (13)	−0.0058 (11)	−0.0116 (12)
C3	0.0512 (14)	0.0773 (18)	0.0454 (13)	0.0050 (13)	−0.0029 (11)	−0.0023 (12)
C4	0.0730 (18)	0.0544 (15)	0.0553 (15)	0.0097 (13)	−0.0018 (13)	−0.0051 (12)
C5	0.0682 (16)	0.0525 (14)	0.0487 (14)	−0.0091 (12)	−0.0068 (12)	−0.0094 (11)
C6	0.0498 (13)	0.0476 (13)	0.0342 (11)	−0.0078 (10)	−0.0002 (9)	−0.0016 (9)
C7	0.0474 (13)	0.0574 (14)	0.0489 (13)	−0.0112 (11)	−0.0016 (10)	−0.0055 (11)
C8	0.0347 (11)	0.0441 (12)	0.0510 (13)	−0.0048 (9)	−0.0096 (9)	−0.0066 (9)
C9	0.0441 (12)	0.0449 (12)	0.0550 (14)	−0.0073 (10)	−0.0075 (10)	−0.0077 (10)
C10	0.0415 (12)	0.0674 (16)	0.0533 (14)	−0.0119 (11)	−0.0056 (10)	−0.0156 (12)
C11	0.0532 (15)	0.083 (2)	0.0517 (15)	−0.0192 (13)	−0.0068 (12)	0.0057 (13)
C12	0.0577 (15)	0.0552 (15)	0.0711 (18)	−0.0142 (12)	−0.0175 (13)	0.0090 (13)
C13	0.0419 (12)	0.0435 (13)	0.0656 (16)	−0.0075 (9)	−0.0162 (11)	−0.0027 (11)
C14	0.0484 (13)	0.0441 (13)	0.0858 (19)	0.0003 (10)	−0.0270 (13)	−0.0175 (12)
C15	0.0471 (13)	0.0589 (15)	0.0652 (16)	0.0085 (11)	−0.0178 (11)	−0.0216 (12)

Cl—C10	1.739 (3)	C5—H5A	0.9300
N—C15	1.370 (3)	C6—C7	1.509 (3)
N—C8	1.409 (3)	C7—H7A	0.9700
N—C7	1.456 (3)	C7—H7B	0.9700
O1—C14	1.221 (3)	C8—C9	1.375 (3)
C1—C2	1.385 (4)	C8—C13	1.402 (3)
C1—C6	1.391 (3)	C9—C10	1.385 (4)
C1—H1A	0.9300	C9—H9A	0.9300
O2—C15	1.224 (3)	C10—C11	1.383 (4)
C2—C3	1.374 (4)	C11—C12	1.377 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.372 (4)	C12—C13	1.372 (4)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.390 (4)	C13—C14	1.467 (4)
C4—H4A	0.9300	C14—C15	1.498 (3)
C5—C6	1.381 (3)
C15—N—C8	110.1 (2)	H7A—C7—H7B	107.8
C15—N—C7	125.0 (2)	C9—C8—C13	121.4 (2)
C8—N—C7	124.52 (19)	C9—C8—N	128.0 (2)
C2—C1—C6	121.0 (2)	C13—C8—N	110.6 (2)
C2—C1—H1A	119.5	C8—C9—C10	116.3 (2)
C6—C1—H1A	119.5	C8—C9—H9A	121.9
C3—C2—C1	119.8 (3)	C10—C9—H9A	121.9
C3—C2—H2A	120.1	C11—C10—C9	123.5 (2)
C1—C2—H2A	120.1	C11—C10—Cl	118.5 (2)
C4—C3—C2	120.0 (2)	C9—C10—Cl	118.0 (2)
C4—C3—H3A	120.0	C12—C11—C10	118.9 (3)
C2—C3—H3A	120.0	C12—C11—H11A	120.5
C3—C4—C5	120.1 (3)	C10—C11—H11A	120.5
C3—C4—H4A	119.9	C13—C12—C11	119.4 (2)
C5—C4—H4A	119.9	C13—C12—H12A	120.3
C6—C5—C4	120.7 (3)	C11—C12—H12A	120.3
C6—C5—H5A	119.6	C12—C13—C8	120.4 (2)
C4—C5—H5A	119.6	C12—C13—C14	133.5 (2)
C5—C6—C1	118.2 (2)	C8—C13—C14	106.1 (2)
C5—C6—C7	121.1 (2)	O1—C14—C13	128.7 (3)
C1—C6—C7	120.6 (2)	O1—C14—C15	125.0 (3)
N—C7—C6	112.49 (19)	C13—C14—C15	106.3 (2)
N—C7—H7A	109.1	O2—C15—N	125.5 (2)
C6—C7—H7A	109.1	O2—C15—C14	127.6 (2)
N—C7—H7B	109.1	N—C15—C14	107.0 (2)
C6—C7—H7B	109.1
C6—C1—C2—C3	−0.1 (4)	Cl—C10—C11—C12	−179.28 (19)
C1—C2—C3—C4	−0.1 (4)	C10—C11—C12—C13	−0.1 (4)
C2—C3—C4—C5	0.3 (4)	C11—C12—C13—C8	−0.1 (4)
C3—C4—C5—C6	−0.2 (4)	C11—C12—C13—C14	179.6 (2)
C4—C5—C6—C1	0.1 (4)	C9—C8—C13—C12	0.2 (3)
C4—C5—C6—C7	177.8 (2)	N—C8—C13—C12	179.4 (2)
C2—C1—C6—C5	0.1 (4)	C9—C8—C13—C14	−179.6 (2)
C2—C1—C6—C7	−177.6 (2)	N—C8—C13—C14	−0.4 (2)
C15—N—C7—C6	97.7 (3)	C12—C13—C14—O1	2.7 (5)
C8—N—C7—C6	−73.8 (3)	C8—C13—C14—O1	−177.6 (2)
C5—C6—C7—N	126.2 (2)	C12—C13—C14—C15	−179.3 (3)
C1—C6—C7—N	−56.1 (3)	C8—C13—C14—C15	0.4 (2)
C15—N—C8—C9	179.4 (2)	C8—N—C15—O2	179.3 (2)
C7—N—C8—C9	−8.0 (3)	C7—N—C15—O2	6.8 (4)
C15—N—C8—C13	0.3 (3)	C8—N—C15—C14	0.0 (3)
C7—N—C8—C13	172.9 (2)	C7—N—C15—C14	−172.6 (2)
C13—C8—C9—C10	−0.1 (3)	O1—C14—C15—O2	−1.5 (4)
N—C8—C9—C10	−179.1 (2)	C13—C14—C15—O2	−179.5 (3)
C8—C9—C10—C11	−0.1 (4)	O1—C14—C15—N	177.8 (2)
C8—C9—C10—Cl	179.39 (16)	C13—C14—C15—N	−0.2 (3)
C9—C10—C11—C12	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.93	2.58	3.431 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.93	2.58	3.431 (3)	152

Symmetry code: (i) .