(Z)-5-Fluoro-3-[(1H-pyrrol-2-yl)methyl-ene]indolin-2-one.

The title compound, C(13)H(9)FN(2)O, a potential neuroprotective agent, consists of an indolinone and a pyrrolyl unit [dihedral angle between the ring planes = 4.9 (1)°]. An intra-molecular hydrogen bond between the carbonyl O atom and the NH group of pyrrole correlates with the Z arrangement of the substituents at the C=C bond. In the crystal, inversion dimers occur, linked by pairs of N-H⋯O bonds.

Related literature

For 3-substituted indole-2-one derivatives tested as protein kinase inhibitors, see: Sun et al. (2003 ▶). For derivatives with anti­tumor activity, see: Andreani et al. (2006 ▶). For derivatives with neuroprotective properties, see: Balderamos et al. (2008 ▶); Johnson et al. (2005 ▶). For related structures, see: Ali et al. (2008 ▶); De (2008 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C13H9FN2O

M = 228.22

Monoclinic,

a = 7.6093 (5) Å

b = 6.1270 (4) Å

c = 22.8912 (16) Å

β = 91.390 (1)°

V = 1066.92 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.35 × 0.24 × 0.08 mm

Data collection

Bruker APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.992

12282 measured reflections

2552 independent reflections

2167 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.137

S = 1.10

2552 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040178/si2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040178/si2132Isup2.hkl

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

C13H9FN2O	F(000) = 472
Mr = 228.22	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6093 (5) Å	Cell parameters from 3595 reflections
b = 6.1270 (4) Å	θ = 2.7–25.4°
c = 22.8912 (16) Å	µ = 0.10 mm−1
β = 91.390 (1)°	T = 293 K
V = 1066.92 (12) Å3	Plates, orange
Z = 4	0.35 × 0.24 × 0.08 mm

Bruker APEX diffractometer	2552 independent reflections
Radiation source: fine-focus sealed tube	2167 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 83.33 pixels mm-1	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.964, Tmax = 0.992	l = −29→29
12282 measured 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3105P] where P = (Fo2 + 2Fc2)/3
2552 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.36941 (18)	0.7704 (2)	−0.02026 (6)	0.0462 (3)
H1	0.4156	0.8783	−0.0384	0.055*
C2	0.3608 (2)	0.7558 (3)	0.03865 (7)	0.0422 (4)
O2	0.41973 (16)	0.89761 (19)	0.07266 (5)	0.0515 (3)
C3	0.27094 (19)	0.5468 (2)	0.05187 (7)	0.0395 (3)
C4	0.1488 (2)	0.2559 (3)	−0.02156 (7)	0.0457 (4)
H4	0.1059	0.1591	0.0060	0.055*
C5	0.1325 (2)	0.2144 (3)	−0.08055 (8)	0.0503 (4)
F5	0.04936 (17)	0.0275 (2)	−0.09798 (5)	0.0727 (4)
C6	0.1934 (2)	0.3515 (3)	−0.12313 (7)	0.0536 (4)
H6	0.1788	0.3157	−0.1624	0.064*
C7	0.2772 (2)	0.5443 (3)	−0.10659 (7)	0.0511 (4)
H7	0.3204	0.6399	−0.1343	0.061*
C8	0.2942 (2)	0.5888 (3)	−0.04789 (7)	0.0421 (4)
C9	0.23179 (19)	0.4481 (2)	−0.00504 (6)	0.0395 (3)
C10	0.2305 (2)	0.4604 (3)	0.10429 (7)	0.0448 (4)
H10	0.1771	0.3241	0.1019	0.054*
N11	0.3347 (2)	0.7320 (3)	0.17745 (6)	0.0587 (4)
H11	0.3819	0.8215	0.1535	0.070*
C12	0.2548 (2)	0.5398 (3)	0.16222 (7)	0.0488 (4)
C13	0.1974 (3)	0.4470 (4)	0.21346 (8)	0.0667 (6)
H13	0.1390	0.3144	0.2167	0.080*
C14	0.2423 (4)	0.5862 (4)	0.25906 (9)	0.0792 (7)
H14	0.2184	0.5654	0.2983	0.095*
C15	0.3282 (4)	0.7598 (4)	0.23562 (9)	0.0756 (7)
H15	0.3746	0.8777	0.2564	0.091*

	U11	U22	U33	U12	U13	U23
N1	0.0597 (8)	0.0390 (7)	0.0402 (7)	−0.0043 (6)	0.0079 (6)	0.0063 (5)
C2	0.0462 (8)	0.0393 (8)	0.0414 (8)	0.0013 (6)	0.0063 (6)	0.0043 (6)
O2	0.0673 (8)	0.0445 (6)	0.0431 (6)	−0.0124 (5)	0.0075 (5)	−0.0007 (5)
C3	0.0408 (7)	0.0384 (8)	0.0395 (8)	0.0016 (6)	0.0050 (6)	0.0011 (6)
C4	0.0496 (9)	0.0423 (9)	0.0453 (9)	−0.0009 (7)	0.0042 (7)	0.0017 (7)
C5	0.0562 (10)	0.0442 (9)	0.0505 (10)	0.0006 (7)	−0.0014 (7)	−0.0068 (7)
F5	0.0964 (9)	0.0608 (7)	0.0608 (7)	−0.0194 (6)	−0.0027 (6)	−0.0137 (6)
C6	0.0669 (11)	0.0565 (10)	0.0374 (8)	0.0071 (9)	−0.0002 (7)	−0.0055 (7)
C7	0.0663 (11)	0.0503 (10)	0.0370 (8)	0.0057 (8)	0.0066 (7)	0.0063 (7)
C8	0.0465 (8)	0.0390 (8)	0.0409 (8)	0.0055 (6)	0.0036 (6)	0.0038 (6)
C9	0.0411 (7)	0.0401 (8)	0.0374 (8)	0.0053 (6)	0.0047 (6)	0.0027 (6)
C10	0.0473 (8)	0.0448 (9)	0.0425 (9)	−0.0051 (7)	0.0041 (6)	0.0037 (7)
N11	0.0806 (11)	0.0554 (9)	0.0404 (8)	−0.0147 (8)	0.0106 (7)	0.0001 (6)
C12	0.0545 (9)	0.0523 (10)	0.0398 (9)	−0.0033 (7)	0.0046 (7)	0.0045 (7)
C13	0.0903 (15)	0.0664 (13)	0.0436 (10)	−0.0170 (11)	0.0087 (9)	0.0076 (9)
C14	0.124 (2)	0.0762 (15)	0.0380 (10)	−0.0175 (14)	0.0131 (11)	0.0031 (9)
C15	0.1179 (18)	0.0673 (13)	0.0420 (10)	−0.0167 (13)	0.0082 (11)	−0.0050 (9)

N1—C2	1.355 (2)	C7—C8	1.374 (2)
N1—C8	1.396 (2)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.397 (2)
C2—O2	1.2429 (19)	C10—C12	1.421 (2)
C2—C3	1.486 (2)	C10—H10	0.9300
C3—C10	1.354 (2)	N11—C15	1.344 (2)
C3—C9	1.460 (2)	N11—C12	1.367 (2)
C4—C5	1.377 (2)	N11—H11	0.8600
C4—C9	1.385 (2)	C12—C13	1.384 (2)
C4—H4	0.9300	C13—C14	1.385 (3)
C5—F5	1.364 (2)	C13—H13	0.9300
C5—C6	1.376 (3)	C14—C15	1.365 (3)
C6—C7	1.390 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C2—N1—C8	111.66 (13)	N1—C8—C9	108.45 (14)
C2—N1—H1	124.2	C4—C9—C8	119.57 (14)
C8—N1—H1	124.2	C4—C9—C3	132.66 (14)
O2—C2—N1	123.50 (14)	C8—C9—C3	107.77 (14)
O2—C2—C3	129.46 (14)	C3—C10—C12	131.79 (16)
N1—C2—C3	107.04 (14)	C3—C10—H10	114.1
C10—C3—C9	125.66 (15)	C12—C10—H10	114.1
C10—C3—C2	129.26 (15)	C15—N11—C12	109.57 (16)
C9—C3—C2	105.08 (13)	C15—N11—H11	125.2
C5—C4—C9	117.01 (15)	C12—N11—H11	125.2
C5—C4—H4	121.5	N11—C12—C13	106.60 (16)
C9—C4—H4	121.5	N11—C12—C10	125.47 (15)
F5—C5—C6	117.86 (15)	C13—C12—C10	127.88 (17)
F5—C5—C4	118.16 (16)	C12—C13—C14	107.97 (19)
C6—C5—C4	123.97 (16)	C12—C13—H13	126.0
C5—C6—C7	119.06 (15)	C14—C13—H13	126.0
C5—C6—H6	120.5	C15—C14—C13	107.19 (18)
C7—C6—H6	120.5	C15—C14—H14	126.4
C8—C7—C6	117.81 (15)	C13—C14—H14	126.4
C8—C7—H7	121.1	N11—C15—C14	108.66 (19)
C6—C7—H7	121.1	N11—C15—H15	125.7
C7—C8—N1	128.97 (15)	C14—C15—H15	125.7
C7—C8—C9	122.58 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.03	2.8711 (17)	166
N11—H11···O2	0.86	1.94	2.6977 (19)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.03	2.8711 (17)	166
N11—H11⋯O2	0.86	1.94	2.6977 (19)	147

Symmetry code: (i) .