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

In the title compound, C(16)H(12)FNO(3), the dihedral angle between the benzene ring and the plane of the indole ring system is 71.60 (6)°. In the crystal, mol-ecules stack along the b axis through π-π inter-actions between the adjacent indole-2,3-dione units with a centroid-centroid distance of 3.649 (3) Å. Inter-molecular C-H⋯O=C and C-H⋯π inter-actions further stabilize the structure, forming a three-dimensional framework.

Related literature

For background to the use of 5-fluoro­indoline-2,3-dione and its analogues as anti-tumour agents, see: Uddin et al. (2007 ▶); Penthala et al. (2010 ▶). For a related structure, see: Wu et al. (2011 ▶).

Experimental

Crystal data

C16H12FNO3

M = 285.27

Orthorhombic,

a = 17.779 (4) Å

b = 7.1575 (14) Å

c = 21.306 (4) Å

V = 2711.3 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.641, T max = 0.746

25325 measured reflections

3202 independent reflections

1604 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.136

S = 1.01

3202 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

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 datablock(s) I, global. DOI: 10.1107/S1600536811023488/sj5156sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023488/sj5156Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023488/sj5156Isup3.cml

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

C16H12FNO3	Z = 8
Mr = 285.27	F(000) = 1184
Orthorhombic, Pbca	Dx = 1.398 Mg m−3
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 17.779 (4) Å	µ = 0.11 mm−1
b = 7.1575 (14) Å	T = 296 K
c = 21.306 (4) Å	Block, yellow
V = 2711.3 (9) Å3	0.40 × 0.30 × 0.20 mm

Bruker APEXII CCD area-detector diffractometer	3202 independent reflections
Radiation source: fine-focus sealed tube	1604 reflections with I > 2σ(I)
graphite	Rint = 0.100
ω scans	θmax = 27.9°, θmin = 6.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −23→23
Tmin = 0.641, Tmax = 0.746	k = −9→9
25325 measured reflections	l = −28→27

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.1083P] where P = (Fo2 + 2Fc2)/3
3202 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 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 > 2sigma(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
F1	0.08487 (7)	0.2819 (2)	0.39404 (6)	0.0874 (4)
O1	0.38817 (8)	0.2815 (2)	0.34962 (7)	0.0788 (5)
O2	0.47658 (8)	0.2065 (2)	0.46416 (7)	0.0738 (5)
O3	0.36524 (10)	0.7189 (2)	0.74362 (7)	0.0833 (5)
N1	0.35821 (8)	0.1683 (2)	0.50669 (7)	0.0508 (4)
C1	0.42398 (10)	0.5766 (3)	0.65265 (9)	0.0569 (5)
H1A	0.4579	0.6745	0.6482	0.068*
C2	0.37197 (11)	0.5783 (3)	0.70053 (9)	0.0579 (5)
C3	0.32168 (12)	0.4322 (3)	0.70640 (9)	0.0668 (6)
H3A	0.2866	0.4325	0.7388	0.080*
C4	0.32346 (12)	0.2861 (3)	0.66446 (10)	0.0630 (6)
H4A	0.2890	0.1892	0.6687	0.076*
C5	0.37553 (11)	0.2802 (3)	0.61599 (8)	0.0502 (5)
C6	0.42526 (10)	0.4275 (3)	0.61115 (9)	0.0542 (5)
H6A	0.4607	0.4268	0.5791	0.065*
C7	0.37914 (11)	0.1181 (3)	0.57101 (9)	0.0576 (5)
H7A	0.4299	0.0683	0.5709	0.069*
H7B	0.3458	0.0202	0.5857	0.069*
C8	0.36179 (12)	0.2478 (3)	0.40047 (10)	0.0543 (5)
C9	0.40834 (11)	0.2057 (3)	0.45996 (9)	0.0545 (5)
C10	0.28347 (10)	0.1884 (2)	0.48441 (9)	0.0451 (4)
C11	0.28318 (10)	0.2373 (2)	0.42095 (9)	0.0472 (5)
C12	0.21641 (11)	0.2671 (3)	0.38876 (9)	0.0552 (5)
H12A	0.2157	0.2987	0.3464	0.066*
C13	0.15144 (11)	0.2476 (3)	0.42286 (10)	0.0570 (5)
C14	0.15047 (11)	0.1975 (3)	0.48525 (10)	0.0569 (5)
H14A	0.1048	0.1840	0.5060	0.068*
C15	0.21751 (10)	0.1671 (3)	0.51749 (9)	0.0522 (5)
H15A	0.2177	0.1337	0.5597	0.063*
C16	0.42269 (18)	0.8594 (4)	0.74439 (13)	0.0992 (9)
H16A	0.4116	0.9495	0.7764	0.149*
H16B	0.4245	0.9205	0.7043	0.149*
H16C	0.4704	0.8021	0.7529	0.149*

	U11	U22	U33	U12	U13	U23
F1	0.0514 (7)	0.1155 (11)	0.0953 (10)	0.0063 (7)	−0.0130 (6)	0.0019 (8)
O1	0.0704 (10)	0.1040 (13)	0.0619 (10)	−0.0115 (8)	0.0144 (8)	0.0097 (8)
O2	0.0460 (9)	0.0904 (11)	0.0851 (11)	−0.0052 (7)	0.0015 (7)	0.0017 (8)
O3	0.0923 (12)	0.0894 (12)	0.0682 (10)	−0.0015 (9)	0.0081 (8)	−0.0262 (9)
N1	0.0480 (9)	0.0532 (9)	0.0510 (9)	−0.0020 (7)	−0.0001 (7)	−0.0018 (7)
C1	0.0512 (11)	0.0608 (13)	0.0587 (12)	−0.0066 (9)	−0.0012 (9)	−0.0035 (10)
C2	0.0604 (12)	0.0652 (13)	0.0480 (11)	0.0062 (11)	−0.0031 (10)	−0.0060 (10)
C3	0.0643 (13)	0.0856 (17)	0.0504 (12)	−0.0053 (12)	0.0107 (10)	−0.0008 (11)
C4	0.0614 (13)	0.0679 (14)	0.0597 (13)	−0.0122 (10)	0.0016 (10)	0.0056 (11)
C5	0.0499 (11)	0.0530 (12)	0.0479 (11)	0.0043 (9)	−0.0050 (9)	0.0054 (9)
C6	0.0448 (11)	0.0656 (13)	0.0520 (11)	0.0007 (10)	0.0024 (8)	−0.0009 (10)
C7	0.0609 (12)	0.0558 (12)	0.0560 (12)	0.0012 (9)	−0.0057 (10)	0.0028 (10)
C8	0.0558 (12)	0.0522 (12)	0.0549 (12)	−0.0070 (9)	0.0042 (10)	0.0004 (9)
C9	0.0483 (12)	0.0524 (12)	0.0628 (13)	−0.0044 (9)	0.0039 (10)	−0.0036 (9)
C10	0.0448 (10)	0.0388 (10)	0.0516 (11)	−0.0020 (8)	0.0028 (8)	−0.0063 (8)
C11	0.0472 (11)	0.0432 (10)	0.0513 (11)	−0.0031 (8)	0.0022 (8)	−0.0030 (8)
C12	0.0584 (13)	0.0533 (12)	0.0539 (12)	−0.0027 (9)	−0.0025 (9)	0.0002 (9)
C13	0.0448 (11)	0.0568 (12)	0.0694 (14)	−0.0004 (9)	−0.0068 (10)	−0.0036 (10)
C14	0.0466 (11)	0.0541 (12)	0.0699 (14)	−0.0051 (9)	0.0086 (9)	−0.0061 (10)
C15	0.0542 (12)	0.0488 (11)	0.0536 (11)	−0.0029 (9)	0.0079 (9)	−0.0027 (9)
C16	0.138 (3)	0.0752 (17)	0.0848 (18)	−0.0146 (18)	−0.0027 (16)	−0.0240 (14)

F1—C13	1.356 (2)	C6—H6A	0.9300
O1—C8	1.205 (2)	C7—H7A	0.9700
O2—C9	1.217 (2)	C7—H7B	0.9700
O3—C2	1.368 (2)	C8—C11	1.466 (3)
O3—C16	1.433 (3)	C8—C9	1.544 (3)
N1—C9	1.363 (2)	C10—C15	1.377 (2)
N1—C10	1.418 (2)	C10—C11	1.396 (3)
N1—C7	1.465 (2)	C11—C12	1.388 (3)
C1—C2	1.377 (3)	C12—C13	1.372 (3)
C1—C6	1.386 (3)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.377 (3)
C2—C3	1.382 (3)	C14—C15	1.393 (3)
C3—C4	1.375 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.388 (3)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.380 (3)	C16—H16C	0.9600
C5—C7	1.507 (3)
C2—O3—C16	117.50 (18)	O1—C8—C9	124.66 (19)
C9—N1—C10	110.37 (15)	C11—C8—C9	104.88 (16)
C9—N1—C7	124.44 (16)	O2—C9—N1	126.83 (19)
C10—N1—C7	125.18 (15)	O2—C9—C8	126.46 (18)
C2—C1—C6	119.38 (18)	N1—C9—C8	106.71 (16)
C2—C1—H1A	120.3	C15—C10—C11	121.35 (17)
C6—C1—H1A	120.3	C15—C10—N1	127.97 (17)
O3—C2—C1	124.24 (19)	C11—C10—N1	110.67 (15)
O3—C2—C3	116.10 (18)	C12—C11—C10	121.35 (16)
C1—C2—C3	119.66 (18)	C12—C11—C8	131.34 (17)
C4—C3—C2	120.11 (19)	C10—C11—C8	107.31 (16)
C4—C3—H3A	119.9	C13—C12—C11	116.29 (18)
C2—C3—H3A	119.9	C13—C12—H12A	121.9
C3—C4—C5	121.47 (19)	C11—C12—H12A	121.9
C3—C4—H4A	119.3	F1—C13—C12	118.47 (19)
C5—C4—H4A	119.3	F1—C13—C14	118.25 (18)
C6—C5—C4	117.37 (18)	C12—C13—C14	123.27 (18)
C6—C5—C7	120.92 (17)	C13—C14—C15	120.39 (18)
C4—C5—C7	121.70 (18)	C13—C14—H14A	119.8
C5—C6—C1	122.01 (17)	C15—C14—H14A	119.8
C5—C6—H6A	119.0	C10—C15—C14	117.34 (18)
C1—C6—H6A	119.0	C10—C15—H15A	121.3
N1—C7—C5	113.29 (15)	C14—C15—H15A	121.3
N1—C7—H7A	108.9	O3—C16—H16A	109.5
C5—C7—H7A	108.9	O3—C16—H16B	109.5
N1—C7—H7B	108.9	H16A—C16—H16B	109.5
C5—C7—H7B	108.9	O3—C16—H16C	109.5
H7A—C7—H7B	107.7	H16A—C16—H16C	109.5
O1—C8—C11	130.47 (19)	H16B—C16—H16C	109.5

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1i	0.93	3.03	3.812 (2)	142
C14—H14A···O2ii	0.93	2.49	3.345 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1i	0.93	3.03	3.812 (2)	142
C14—H14A⋯O2ii	0.93	2.49	3.345 (2)	153

Symmetry codes: (i) ; (ii) .