1-[(2-Chloro-3-quinol-yl)meth-yl]indoline-2,3-dione.

In the title compound, C(18)H(11)ClN(2)O(2), the isatin and 2-chloro-3-methyl-quinoline units are both almost planar, with r.m.s. deviations of 0.0075 and 0.0086 Å, respectively, and the dihedral angle between the mean planes of the two units is 83.13 (7)°. In the crystal, a weak inter-molecular C-H⋯ O inter-action links the mol-ecules into chains along the c axis.

Related literature

For background to the use of N-substituted indole-2,3-diones as inter­mediates and synthetic precursors for the preparation of heterocyclic compounds, see: Silaicheva et al. (2009 ▶). For the biological activity of N-substituted indole-2,3-diones, see: Vine et al. (2007 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H11ClN2O2

M = 322.74

Monoclinic,

a = 21.4984 (8) Å

b = 5.3061 (2) Å

c = 13.0356 (4) Å

β = 99.718 (3)°

V = 1465.67 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.33 × 0.30 × 0.27 mm

Data collection

Oxford Diffraction Excalibur diffractometer

17920 measured reflections

2724 independent reflections

1731 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.085

S = 0.90

2724 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013966/pv2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013966/pv2276Isup2.hkl

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

C18H11ClN2O2	F(000) = 664
Mr = 322.74	Dx = 1.463 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2724 reflections
a = 21.4984 (8) Å	θ = 2.9–25.5°
b = 5.3061 (2) Å	µ = 0.27 mm−1
c = 13.0356 (4) Å	T = 293 K
β = 99.718 (3)°	Block, orange
V = 1465.67 (9) Å3	0.33 × 0.30 × 0.27 mm
Z = 4

Oxford Diffraction Excalibur diffractometer	1731 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 25.5°, θmin = 2.9°
Detector resolution: 0 pixels mm-1	h = −26→26
ω scans	k = −6→6
17920 measured reflections	l = −15→15
2724 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3
2724 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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 > 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	0.32510 (3)	1.40527 (10)	0.51979 (4)	0.0614 (2)
N1	0.38948 (7)	1.0493 (3)	0.45048 (11)	0.0458 (4)
C2	0.28707 (8)	1.1294 (3)	0.34507 (13)	0.0360 (4)
C3	0.29797 (8)	0.9460 (3)	0.27719 (13)	0.0379 (4)
H3	0.2675	0.9121	0.2192	0.046*
N2	0.18214 (7)	1.2157 (3)	0.24049 (11)	0.0398 (4)
C13	0.10081 (8)	1.0002 (3)	0.13973 (13)	0.0376 (4)
C1	0.33623 (9)	1.1692 (3)	0.43088 (13)	0.0406 (5)
C14	0.13853 (8)	1.0147 (3)	0.23746 (14)	0.0377 (4)
C8	0.39988 (8)	0.8632 (3)	0.38138 (14)	0.0407 (5)
O1	0.20473 (6)	1.5156 (3)	0.12348 (11)	0.0579 (4)
C4	0.36754 (9)	0.6131 (3)	0.22547 (15)	0.0481 (5)
H4	0.3382	0.5751	0.1666	0.058*
O2	0.10171 (7)	1.2586 (3)	−0.01339 (11)	0.0635 (4)
C10	0.22789 (9)	1.2877 (3)	0.33140 (14)	0.0463 (5)
H10A	0.2085	1.2717	0.3931	0.056*
H10B	0.2392	1.4632	0.3249	0.056*
C9	0.35465 (8)	0.8066 (3)	0.29322 (13)	0.0375 (4)
C15	0.05482 (9)	0.8170 (4)	0.11805 (15)	0.0477 (5)
H15	0.0300	0.8064	0.0525	0.057*
C12	0.12083 (8)	1.1985 (3)	0.07592 (15)	0.0423 (5)
C7	0.45672 (9)	0.7252 (4)	0.39988 (16)	0.0547 (6)
H7	0.4871	0.7616	0.4576	0.066*
C5	0.42260 (10)	0.4820 (4)	0.24572 (18)	0.0587 (6)
H5	0.4306	0.3541	0.2010	0.070*
C11	0.17522 (9)	1.3370 (4)	0.14680 (15)	0.0418 (5)
C6	0.46691 (10)	0.5389 (4)	0.33319 (19)	0.0588 (6)
H6	0.5043	0.4475	0.3463	0.071*
C18	0.13105 (9)	0.8492 (4)	0.31574 (15)	0.0476 (5)
H18	0.1561	0.8586	0.3812	0.057*
C16	0.04657 (9)	0.6503 (4)	0.19561 (18)	0.0542 (6)
H16	0.0156	0.5264	0.1829	0.065*
C17	0.08426 (10)	0.6670 (4)	0.29230 (18)	0.0552 (6)
H17	0.0781	0.5524	0.3436	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.0765 (4)	0.0609 (4)	0.0442 (3)	−0.0082 (3)	0.0028 (3)	−0.0161 (2)
N1	0.0427 (10)	0.0504 (10)	0.0406 (9)	−0.0072 (8)	−0.0039 (8)	0.0046 (8)
C2	0.0363 (10)	0.0362 (10)	0.0346 (10)	−0.0046 (9)	0.0038 (8)	−0.0006 (8)
C3	0.0337 (10)	0.0422 (11)	0.0359 (10)	−0.0036 (9)	0.0000 (8)	0.0003 (9)
N2	0.0341 (9)	0.0400 (9)	0.0425 (10)	0.0007 (7)	−0.0016 (7)	−0.0043 (7)
C13	0.0320 (10)	0.0364 (10)	0.0436 (12)	0.0019 (9)	0.0040 (9)	0.0000 (9)
C1	0.0460 (12)	0.0415 (11)	0.0335 (11)	−0.0096 (10)	0.0042 (9)	−0.0009 (9)
C14	0.0340 (11)	0.0335 (10)	0.0461 (12)	0.0066 (9)	0.0078 (9)	−0.0017 (9)
C8	0.0319 (11)	0.0430 (11)	0.0457 (12)	−0.0052 (9)	0.0027 (9)	0.0079 (9)
O1	0.0489 (9)	0.0526 (9)	0.0719 (10)	−0.0123 (7)	0.0092 (7)	0.0042 (7)
C4	0.0427 (12)	0.0496 (12)	0.0520 (13)	0.0032 (10)	0.0078 (10)	−0.0040 (10)
O2	0.0690 (10)	0.0721 (10)	0.0457 (9)	−0.0133 (8)	−0.0013 (8)	0.0077 (7)
C10	0.0439 (12)	0.0458 (11)	0.0465 (12)	0.0017 (10)	0.0004 (10)	−0.0106 (9)
C9	0.0326 (11)	0.0405 (10)	0.0388 (11)	−0.0039 (9)	0.0045 (9)	0.0038 (9)
C15	0.0394 (12)	0.0460 (11)	0.0554 (13)	−0.0005 (10)	0.0008 (10)	−0.0040 (10)
C12	0.0402 (12)	0.0448 (11)	0.0410 (12)	0.0026 (9)	0.0045 (10)	−0.0006 (10)
C7	0.0337 (12)	0.0623 (14)	0.0632 (14)	−0.0041 (11)	−0.0062 (10)	0.0136 (12)
C5	0.0492 (14)	0.0546 (13)	0.0741 (16)	0.0050 (11)	0.0160 (12)	−0.0028 (11)
C11	0.0330 (11)	0.0405 (11)	0.0516 (13)	0.0026 (10)	0.0069 (9)	0.0001 (10)
C6	0.0395 (13)	0.0548 (14)	0.0824 (17)	0.0074 (11)	0.0107 (12)	0.0099 (12)
C18	0.0476 (13)	0.0477 (12)	0.0477 (12)	0.0142 (11)	0.0087 (10)	0.0045 (10)
C16	0.0413 (13)	0.0421 (12)	0.0810 (17)	−0.0023 (10)	0.0155 (12)	−0.0007 (12)
C17	0.0576 (14)	0.0415 (12)	0.0726 (16)	0.0104 (11)	0.0282 (13)	0.0122 (11)

Cl1—C1	1.7503 (18)	C4—C9	1.412 (2)
N1—C1	1.297 (2)	C4—H4	0.9300
N1—C8	1.380 (2)	O2—C12	1.210 (2)
C2—C3	1.362 (2)	C10—H10A	0.9700
C2—C1	1.419 (3)	C10—H10B	0.9700
C2—C10	1.510 (2)	C15—C16	1.377 (3)
C3—C9	1.411 (2)	C15—H15	0.9300
C3—H3	0.9300	C12—C11	1.548 (3)
N2—C11	1.366 (2)	C7—C6	1.358 (3)
N2—C14	1.416 (2)	C7—H7	0.9300
N2—C10	1.457 (2)	C5—C6	1.390 (3)
C13—C15	1.381 (2)	C5—H5	0.9300
C13—C14	1.392 (2)	C6—H6	0.9300
C13—C12	1.451 (3)	C18—C17	1.391 (3)
C14—C18	1.376 (2)	C18—H18	0.9300
C8—C9	1.407 (2)	C16—C17	1.381 (3)
C8—C7	1.410 (3)	C16—H16	0.9300
O1—C11	1.208 (2)	C17—H17	0.9300
C4—C5	1.360 (3)
C1—N1—C8	117.22 (16)	C8—C9—C3	118.02 (17)
C3—C2—C1	115.56 (17)	C8—C9—C4	118.98 (17)
C3—C2—C10	123.70 (16)	C3—C9—C4	123.00 (17)
C1—C2—C10	120.73 (16)	C16—C15—C13	118.58 (18)
C2—C3—C9	121.17 (17)	C16—C15—H15	120.7
C2—C3—H3	119.4	C13—C15—H15	120.7
C9—C3—H3	119.4	O2—C12—C13	131.09 (18)
C11—N2—C14	110.98 (15)	O2—C12—C11	123.28 (17)
C11—N2—C10	124.07 (15)	C13—C12—C11	105.62 (16)
C14—N2—C10	124.94 (15)	C6—C7—C8	119.8 (2)
C15—C13—C14	120.82 (16)	C6—C7—H7	120.1
C15—C13—C12	131.64 (17)	C8—C7—H7	120.1
C14—C13—C12	107.54 (16)	C4—C5—C6	120.1 (2)
N1—C1—C2	126.69 (17)	C4—C5—H5	119.9
N1—C1—Cl1	115.82 (14)	C6—C5—H5	119.9
C2—C1—Cl1	117.49 (15)	O1—C11—N2	127.74 (18)
C18—C14—C13	121.36 (17)	O1—C11—C12	126.75 (18)
C18—C14—N2	128.29 (17)	N2—C11—C12	105.50 (16)
C13—C14—N2	110.35 (15)	C7—C6—C5	121.4 (2)
N1—C8—C9	121.33 (17)	C7—C6—H6	119.3
N1—C8—C7	119.42 (18)	C5—C6—H6	119.3
C9—C8—C7	119.24 (18)	C14—C18—C17	116.82 (19)
C5—C4—C9	120.46 (19)	C14—C18—H18	121.6
C5—C4—H4	119.8	C17—C18—H18	121.6
C9—C4—H4	119.8	C15—C16—C17	120.00 (19)
N2—C10—C2	112.95 (14)	C15—C16—H16	120.0
N2—C10—H10A	109.0	C17—C16—H16	120.0
C2—C10—H10A	109.0	C16—C17—C18	122.42 (19)
N2—C10—H10B	109.0	C16—C17—H17	118.8
C2—C10—H10B	109.0	C18—C17—H17	118.8
H10A—C10—H10B	107.8
C1—C2—C3—C9	0.3 (2)	C2—C3—C9—C4	179.27 (16)
C10—C2—C3—C9	179.03 (16)	C5—C4—C9—C8	0.6 (3)
C8—N1—C1—C2	−0.1 (3)	C5—C4—C9—C3	−178.91 (17)
C8—N1—C1—Cl1	−179.53 (12)	C14—C13—C15—C16	0.7 (3)
C3—C2—C1—N1	−0.2 (3)	C12—C13—C15—C16	179.68 (17)
C10—C2—C1—N1	−178.90 (17)	C15—C13—C12—O2	1.3 (3)
C3—C2—C1—Cl1	179.28 (12)	C14—C13—C12—O2	−179.6 (2)
C10—C2—C1—Cl1	0.5 (2)	C15—C13—C12—C11	−179.36 (18)
C15—C13—C14—C18	−0.5 (3)	C14—C13—C12—C11	−0.28 (18)
C12—C13—C14—C18	−179.71 (16)	N1—C8—C7—C6	178.92 (17)
C15—C13—C14—N2	179.64 (15)	C9—C8—C7—C6	−0.5 (3)
C12—C13—C14—N2	0.45 (19)	C9—C4—C5—C6	−0.4 (3)
C11—N2—C14—C18	179.71 (17)	C14—N2—C11—O1	179.81 (17)
C10—N2—C14—C18	−1.1 (3)	C10—N2—C11—O1	0.6 (3)
C11—N2—C14—C13	−0.46 (19)	C14—N2—C11—C12	0.25 (18)
C10—N2—C14—C13	178.72 (15)	C10—N2—C11—C12	−178.93 (15)
C1—N1—C8—C9	0.2 (3)	O2—C12—C11—O1	−0.2 (3)
C1—N1—C8—C7	−179.23 (16)	C13—C12—C11—O1	−179.55 (17)
C11—N2—C10—C2	−98.40 (18)	O2—C12—C11—N2	179.41 (17)
C14—N2—C10—C2	82.5 (2)	C13—C12—C11—N2	0.02 (18)
C3—C2—C10—N2	2.8 (2)	C8—C7—C6—C5	0.7 (3)
C1—C2—C10—N2	−178.58 (16)	C4—C5—C6—C7	−0.2 (3)
N1—C8—C9—C3	0.0 (3)	C13—C14—C18—C17	0.2 (3)
C7—C8—C9—C3	179.40 (16)	N2—C14—C18—C17	180.00 (16)
N1—C8—C9—C4	−179.55 (15)	C13—C15—C16—C17	−0.6 (3)
C7—C8—C9—C4	−0.2 (3)	C15—C16—C17—C18	0.3 (3)
C2—C3—C9—C8	−0.3 (2)	C14—C18—C17—C16	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2	0.93	2.49	2.842 (2)	102
C17—H17···O2i	0.93	2.48	3.367 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2i	0.93	2.48	3.367 (3)	160

Symmetry code: (i) .