2-(2-Fluoro-4-hy-droxy-benz-yl)isoindoline-1,3-dione.

In the title compound, C(15)H(10)FNO(3), the dihedral angle between the isoindoline-1,3-dione and 3-fluoro-4-methyl-phenol groups is 86.88 (8)°. The isoindoline-1,3-dione fragment is almost planar, with an r.m.s. deviation of 0.0154 Å within the group. Inter-molecular C-H⋯O hydrogen bonds generate C(6) chains running parallel to the [010] direction.

Related literature

For background to indoline-1,3-dione and its derivatives, see: Raza et al. (2010 ▶). For discussion of the broad spectrum of properties of these compounds, see: Bhattacharya & Chakrabarti (1998 ▶). For discussion of their anti-inflammatory properties, see: Sridhar & Ramesh (2001 ▶). For discussion of their anxiogenic activities, see: Medvedev et al. (1996 ▶). For related structures, see: Asad et al. (2012 ▶); Fu et al. (2010 ▶). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H10FNO3

M = 271.24

Monoclinic,

a = 12.4362 (7) Å

b = 13.8189 (8) Å

c = 7.2376 (4) Å

β = 105.784 (6)°

V = 1196.92 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.49 × 0.36 × 0.16 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶) and Clark & Reid (1995 ▶)] T min = 0.977, T max = 0.995

6558 measured reflections

2475 independent reflections

1455 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.141

S = 1.04

2475 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812029923/mw2073sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029923/mw2073Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029923/mw2073Isup3.cml

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

C15H10FNO3	F(000) = 560
Mr = 271.24	Dx = 1.505 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1089 reflections
a = 12.4362 (7) Å	θ = 3.3–29.3°
b = 13.8189 (8) Å	µ = 0.12 mm−1
c = 7.2376 (4) Å	T = 296 K
β = 105.784 (6)°	Plate, yellow
V = 1196.92 (12) Å3	0.49 × 0.36 × 0.16 mm
Z = 4

Agilent Xcalibur Eos diffractometer	2475 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 16.1333 pixels mm-1	θmax = 26.5°, θmin = 3.3°
ω scans	h = −15→15
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012) and Clark & Reid (1995)]	k = −10→17
Tmin = 0.977, Tmax = 0.995	l = −9→9
6558 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.052P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2475 reflections	Δρmax = 0.27 e Å−3
182 parameters	Δρmin = −0.25 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

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
F1	0.51132 (13)	0.39770 (13)	0.2014 (2)	0.0744 (5)
O1	0.62844 (14)	0.34620 (14)	0.8605 (2)	0.0669 (6)
H1	0.6025	0.3378	0.9521	0.100*
O2	0.14305 (15)	0.22946 (14)	0.1784 (3)	0.0688 (6)
O3	0.15474 (15)	0.55595 (13)	0.2472 (2)	0.0640 (6)
C1	0.4371 (2)	0.3540 (2)	0.7088 (4)	0.0587 (7)
H2	0.4209	0.3437	0.8253	0.070*
C2	0.3525 (2)	0.36576 (18)	0.5413 (4)	0.0512 (7)
H6	0.2786	0.3635	0.5460	0.061*
C3	0.37512 (19)	0.38080 (16)	0.3672 (3)	0.0432 (6)
C4	0.4864 (2)	0.38324 (18)	0.3694 (3)	0.0489 (6)
C5	0.5730 (2)	0.37230 (18)	0.5324 (4)	0.0555 (7)
H3	0.6472	0.3745	0.5292	0.067*
C6	0.5443 (2)	0.35796 (19)	0.6992 (4)	0.0573 (7)
C7	0.2863 (2)	0.39461 (19)	0.1803 (3)	0.0513 (7)
H7A	0.2988	0.4560	0.1244	0.062*
H7B	0.2934	0.3438	0.0920	0.062*
C8	0.1105 (2)	0.31010 (19)	0.1968 (4)	0.0486 (7)
C9	0.00117 (19)	0.34221 (18)	0.2184 (3)	0.0443 (6)
C10	0.00446 (19)	0.44188 (18)	0.2373 (3)	0.0423 (6)
C11	0.1162 (2)	0.47537 (19)	0.2301 (3)	0.0464 (6)
C12	−0.0859 (2)	0.4927 (2)	0.2606 (3)	0.0536 (7)
H12	−0.0835	0.5596	0.2748	0.064*
C13	−0.1802 (2)	0.4405 (2)	0.2620 (3)	0.0603 (8)
H13	−0.2430	0.4731	0.2756	0.072*
C14	−0.1837 (2)	0.3410 (2)	0.2438 (4)	0.0602 (8)
H14	−0.2484	0.3079	0.2460	0.072*
C15	−0.0921 (2)	0.2898 (2)	0.2221 (4)	0.0553 (7)
H15	−0.0937	0.2228	0.2107	0.066*
N1	0.17380 (16)	0.39322 (15)	0.2016 (3)	0.0475 (5)

	U11	U22	U33	U12	U13	U23
F1	0.0609 (10)	0.1071 (14)	0.0657 (9)	−0.0106 (9)	0.0350 (8)	−0.0019 (9)
O1	0.0467 (11)	0.0929 (15)	0.0528 (9)	−0.0076 (10)	−0.0006 (7)	0.0201 (10)
O2	0.0605 (13)	0.0456 (12)	0.1070 (15)	0.0039 (10)	0.0341 (11)	−0.0083 (11)
O3	0.0674 (13)	0.0437 (11)	0.0819 (13)	−0.0074 (10)	0.0220 (10)	−0.0014 (10)
C1	0.0578 (18)	0.0648 (18)	0.0557 (16)	−0.0048 (15)	0.0195 (13)	0.0081 (14)
C2	0.0432 (15)	0.0527 (16)	0.0620 (16)	−0.0025 (12)	0.0217 (12)	0.0039 (13)
C3	0.0406 (14)	0.0352 (13)	0.0560 (14)	−0.0028 (11)	0.0168 (11)	−0.0023 (11)
C4	0.0478 (16)	0.0486 (16)	0.0568 (15)	−0.0043 (13)	0.0253 (13)	−0.0021 (12)
C5	0.0404 (15)	0.0561 (18)	0.0729 (18)	−0.0019 (13)	0.0201 (14)	0.0016 (14)
C6	0.0463 (16)	0.0572 (17)	0.0596 (15)	−0.0028 (13)	−0.0008 (10)	0.0059 (14)
C7	0.0428 (14)	0.0555 (16)	0.0582 (14)	−0.0021 (13)	0.0182 (12)	0.0023 (13)
C8	0.0467 (16)	0.0416 (16)	0.0569 (15)	−0.0002 (13)	0.0132 (12)	−0.0039 (12)
C9	0.0415 (15)	0.0431 (15)	0.0461 (13)	0.0022 (12)	0.0084 (11)	−0.0006 (12)
C10	0.0400 (15)	0.0453 (15)	0.0389 (12)	0.0038 (12)	0.0061 (10)	−0.0012 (11)
C11	0.0489 (16)	0.0408 (16)	0.0465 (13)	−0.0005 (13)	0.0078 (11)	0.0014 (12)
C12	0.0541 (17)	0.0522 (16)	0.0524 (14)	0.0086 (14)	0.0108 (12)	−0.0037 (13)
C13	0.0474 (17)	0.075 (2)	0.0585 (15)	0.0138 (16)	0.0148 (13)	−0.0021 (15)
C14	0.0421 (16)	0.076 (2)	0.0631 (16)	−0.0033 (15)	0.0163 (13)	−0.0001 (15)
C15	0.0466 (16)	0.0528 (16)	0.0664 (16)	−0.0080 (14)	0.0153 (13)	−0.0047 (14)
N1	0.0387 (12)	0.0445 (12)	0.0589 (12)	0.0009 (10)	0.0126 (10)	−0.0005 (10)

F1—C4	1.349 (3)	C7—H7A	0.9700
O1—C6	1.349 (3)	C7—H7B	0.9700
O1—H1	0.8200	C8—N1	1.388 (3)
O2—C8	1.205 (3)	C8—C9	1.478 (3)
O3—C11	1.205 (3)	C9—C15	1.374 (3)
C1—C6	1.354 (4)	C9—C10	1.384 (3)
C1—C2	1.382 (3)	C10—C12	1.373 (3)
C1—H2	0.9300	C10—C11	1.479 (3)
C2—C3	1.379 (3)	C11—N1	1.388 (3)
C2—H6	0.9300	C12—C13	1.380 (4)
C3—C4	1.380 (3)	C12—H12	0.9300
C3—C7	1.508 (3)	C13—C14	1.380 (4)
C4—C5	1.372 (3)	C13—H13	0.9300
C5—C6	1.364 (4)	C14—C15	1.385 (4)
C5—H3	0.9300	C14—H14	0.9300
C7—N1	1.449 (3)	C15—H15	0.9300
C6—O1—H1	109.5	O2—C8—C9	129.5 (2)
C6—C1—C2	118.4 (2)	N1—C8—C9	106.3 (2)
C6—C1—H2	120.8	C15—C9—C10	121.7 (2)
C2—C1—H2	120.8	C15—C9—C8	130.5 (2)
C3—C2—C1	121.5 (2)	C10—C9—C8	107.8 (2)
C3—C2—H6	119.2	C12—C10—C9	121.2 (2)
C1—C2—H6	119.2	C12—C10—C11	130.7 (2)
C2—C3—C4	116.5 (2)	C9—C10—C11	108.1 (2)
C2—C3—C7	123.9 (2)	O3—C11—N1	124.3 (2)
C4—C3—C7	119.6 (2)	O3—C11—C10	129.6 (2)
F1—C4—C5	118.2 (2)	N1—C11—C10	106.1 (2)
F1—C4—C3	118.0 (2)	C10—C12—C13	117.3 (3)
C5—C4—C3	123.9 (2)	C10—C12—H12	121.3
C6—C5—C4	116.3 (2)	C13—C12—H12	121.3
C6—C5—H3	121.8	C12—C13—C14	121.6 (3)
C4—C5—H3	121.8	C12—C13—H13	119.2
O1—C6—C1	119.6 (3)	C14—C13—H13	119.2
O1—C6—C5	117.1 (3)	C13—C14—C15	120.9 (3)
C1—C6—C5	123.3 (2)	C13—C14—H14	119.5
N1—C7—C3	113.3 (2)	C15—C14—H14	119.5
N1—C7—H7A	108.9	C9—C15—C14	117.2 (3)
C3—C7—H7A	108.9	C9—C15—H15	121.4
N1—C7—H7B	108.9	C14—C15—H15	121.4
C3—C7—H7B	108.9	C11—N1—C8	111.6 (2)
H7A—C7—H7B	107.7	C11—N1—C7	123.9 (2)
O2—C8—N1	124.2 (2)	C8—N1—C7	124.5 (2)
C6—C1—C2—C3	0.2 (4)	C8—C9—C10—C11	−0.5 (2)
C1—C2—C3—C4	0.2 (4)	C12—C10—C11—O3	1.8 (4)
C1—C2—C3—C7	−179.6 (2)	C9—C10—C11—O3	−177.4 (2)
C2—C3—C4—F1	179.9 (2)	C12—C10—C11—N1	−179.3 (2)
C7—C3—C4—F1	−0.3 (3)	C9—C10—C11—N1	1.6 (2)
C2—C3—C4—C5	−0.4 (4)	C9—C10—C12—C13	−0.7 (3)
C7—C3—C4—C5	179.4 (2)	C11—C10—C12—C13	−179.8 (2)
F1—C4—C5—C6	179.9 (2)	C10—C12—C13—C14	1.0 (3)
C3—C4—C5—C6	0.2 (4)	C12—C13—C14—C15	−0.4 (4)
C2—C1—C6—O1	−179.6 (2)	C10—C9—C15—C14	0.7 (3)
C2—C1—C6—C5	−0.4 (4)	C8—C9—C15—C14	−179.7 (2)
C4—C5—C6—O1	179.4 (2)	C13—C14—C15—C9	−0.4 (4)
C4—C5—C6—C1	0.2 (4)	O3—C11—N1—C8	177.0 (2)
C2—C3—C7—N1	1.6 (3)	C10—C11—N1—C8	−2.1 (2)
C4—C3—C7—N1	−178.2 (2)	O3—C11—N1—C7	−2.8 (4)
O2—C8—C9—C15	−0.5 (4)	C10—C11—N1—C7	178.11 (18)
N1—C8—C9—C15	179.6 (2)	O2—C8—N1—C11	−178.1 (2)
O2—C8—C9—C10	179.2 (3)	C9—C8—N1—C11	1.8 (3)
N1—C8—C9—C10	−0.7 (2)	O2—C8—N1—C7	1.7 (4)
C15—C9—C10—C12	−0.1 (3)	C9—C8—N1—C7	−178.4 (2)
C8—C9—C10—C12	−179.79 (19)	C3—C7—N1—C11	92.4 (3)
C15—C9—C10—C11	179.2 (2)	C3—C7—N1—C8	−87.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···F1i	0.82	2.52	3.267 (2)	152
C2—H6···O2ii	0.93	2.51	3.303 (3)	144
C12—H12···O2iii	0.93	2.51	3.403 (3)	161
C15—H15···O3iv	0.93	2.47	3.346 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯F1i	0.82	2.52	3.267 (2)	152
C2—H6⋯O2ii	0.93	2.51	3.303 (3)	144
C12—H12⋯O2iii	0.93	2.51	3.403 (3)	161
C15—H15⋯O3iv	0.93	2.47	3.346 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .