5,6-Dichloro-2-(2-fluoro-phen-yl)iso-indoline-1,3-dione.

The crystal structure of the title compound, C(14)H(6)Cl(2)FNO(2), exhibits C-H⋯π and π-π inter-actions, which generate C(3) chains in the [100] direction. The π-π inter-action occurs between the aromatic rings of isoindoline units, with a centroid-centroid distance of 3.672 Å and an inter-planar separation of 3.528 Å. The isoindoline unit is planar and inclined at an angle of 58.63 (18)° to the substituent benzene ring. The F atom is disordered over two positions, with refined occupancies of 0.669 (3) and 0.331 (3).

Related literature

For general background, see: Hall et al. (1987 ▶); Abdel-Hafez (2004 ▶); Sena et al. (2007 ▶). For related literature, see: Loudon (2002 ▶).

Experimental

Crystal data

C14H6Cl2FNO2

M = 310.11

Orthorhombic,

a = 8.0078 (3) Å

b = 27.3570 (9) Å

c = 11.5563 (5) Å

V = 2531.63 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.52 mm−1

T = 296 K

0.76 × 0.50 × 0.20 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.703, T max = 0.907

31181 measured reflections

2384 independent reflections

1956 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.03

2384 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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/S1600536808010544/bt2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010544/bt2693Isup2.hkl

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

C14H6Cl2FNO2	F000 = 1248
Mr = 310.11	Dx = 1.622 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 31181 reflections
a = 8.0078 (3) Å	θ = 1.5–26.2º
b = 27.3570 (9) Å	µ = 0.52 mm−1
c = 11.5563 (5) Å	T = 296 K
V = 2531.63 (17) Å3	Prism, colorless
Z = 8	0.76 × 0.50 × 0.20 mm

Stoe IPDSII diffractometer	2384 independent reflections
Monochromator: plane graphite	1956 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.063
T = 296 K	θmax = 25.6º
ω scan rotation method	θmin = 1.5º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.703, Tmax = 0.907	k = −33→33
31181 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3058P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.15 e Å−3
2384 reflections	Δρmin = −0.17 e Å−3
192 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0107 (9)
Secondary atom site location: difference Fourier map

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	Occ. (<1)
C1	0.28581 (19)	0.61572 (6)	0.53527 (14)	0.0525 (4)
C2	0.30531 (19)	0.56310 (6)	0.56377 (13)	0.0503 (4)
C3	0.2424 (2)	0.52248 (6)	0.50902 (14)	0.0548 (4)
H3	0.1761	0.5254	0.4433	0.066*
C4	0.2809 (2)	0.47693 (6)	0.55490 (15)	0.0554 (4)
C5	0.3825 (2)	0.47286 (6)	0.65266 (15)	0.0578 (4)
C6	0.4455 (2)	0.51427 (7)	0.70638 (15)	0.0585 (4)
H6	0.5133	0.5118	0.7715	0.070*
C7	0.40453 (19)	0.55905 (6)	0.66043 (14)	0.0516 (4)
C8	0.4518 (2)	0.60897 (7)	0.69910 (14)	0.0569 (4)
C9	0.3879 (2)	0.69277 (6)	0.62605 (15)	0.0557 (4)
C10	0.3223 (3)	0.71816 (7)	0.71829 (17)	0.0702 (5)
C11	0.3314 (3)	0.76849 (8)	0.7209 (2)	0.0850 (6)
H11	0.2870	0.7857	0.7831	0.102*
C12	0.4067 (3)	0.79318 (8)	0.6309 (2)	0.0867 (7)
H12	0.4126	0.8271	0.6326	0.104*
C13	0.4725 (3)	0.76831 (8)	0.5395 (2)	0.0867 (7)
H13	0.5230	0.7851	0.4790	0.104*
C14	0.4637 (2)	0.71824 (7)	0.53769 (17)	0.0687 (5)
N1	0.37841 (17)	0.64082 (5)	0.61972 (11)	0.0540 (3)
O1	0.20978 (16)	0.63434 (4)	0.45785 (10)	0.0670 (3)
O2	0.53535 (19)	0.62065 (5)	0.78115 (12)	0.0813 (4)
Cl1	0.20110 (7)	0.425557 (17)	0.48901 (4)	0.07471 (19)
Cl2	0.43176 (8)	0.416515 (19)	0.70844 (5)	0.0847 (2)
F1	0.5355 (3)	0.69169 (7)	0.45401 (16)	0.0918 (7)	0.669 (3)
F2	0.2785 (5)	0.68818 (15)	0.8105 (3)	0.0846 (14)	0.331 (3)
H10	0.2721	0.7019	0.7812	0.102*	0.669 (3)
H14	0.5077	0.7027	0.4724	0.102*	0.331 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0502 (9)	0.0555 (9)	0.0519 (8)	0.0034 (7)	−0.0010 (7)	0.0013 (7)
C2	0.0466 (8)	0.0536 (9)	0.0508 (8)	0.0033 (7)	0.0030 (7)	0.0024 (7)
C3	0.0548 (9)	0.0580 (9)	0.0517 (9)	0.0044 (7)	−0.0005 (7)	0.0001 (7)
C4	0.0535 (9)	0.0547 (9)	0.0579 (9)	0.0009 (7)	0.0110 (8)	−0.0015 (7)
C5	0.0549 (9)	0.0571 (10)	0.0613 (9)	0.0070 (7)	0.0107 (8)	0.0102 (8)
C6	0.0530 (9)	0.0664 (11)	0.0559 (9)	0.0022 (8)	−0.0015 (7)	0.0100 (8)
C7	0.0451 (8)	0.0571 (9)	0.0527 (8)	0.0007 (7)	0.0012 (7)	0.0051 (7)
C8	0.0490 (9)	0.0633 (11)	0.0583 (9)	−0.0074 (8)	−0.0035 (8)	0.0073 (8)
C9	0.0495 (9)	0.0536 (9)	0.0642 (10)	−0.0071 (7)	−0.0033 (8)	0.0033 (8)
C10	0.0716 (12)	0.0697 (12)	0.0694 (12)	−0.0167 (10)	0.0057 (10)	−0.0074 (9)
C11	0.0756 (14)	0.0754 (13)	0.1040 (17)	−0.0095 (11)	0.0001 (12)	−0.0284 (12)
C12	0.0862 (15)	0.0553 (11)	0.1186 (19)	−0.0149 (10)	−0.0175 (14)	0.0007 (12)
C13	0.0981 (17)	0.0699 (13)	0.0921 (15)	−0.0261 (12)	−0.0062 (13)	0.0163 (11)
C14	0.0676 (12)	0.0668 (11)	0.0717 (11)	−0.0108 (9)	0.0053 (10)	0.0052 (9)
N1	0.0530 (8)	0.0533 (7)	0.0556 (7)	−0.0044 (6)	−0.0038 (6)	0.0048 (6)
O1	0.0792 (9)	0.0590 (7)	0.0629 (7)	0.0081 (6)	−0.0172 (6)	0.0035 (5)
O2	0.0848 (10)	0.0764 (9)	0.0826 (9)	−0.0197 (7)	−0.0339 (8)	0.0115 (7)
Cl1	0.0859 (4)	0.0561 (3)	0.0822 (3)	−0.0074 (2)	0.0026 (3)	−0.0062 (2)
Cl2	0.0989 (4)	0.0610 (3)	0.0943 (4)	0.0118 (3)	−0.0031 (3)	0.0214 (2)
F1	0.1037 (15)	0.0859 (13)	0.0857 (12)	−0.0125 (10)	0.0384 (11)	0.0034 (10)
F2	0.086 (3)	0.095 (3)	0.073 (2)	−0.018 (2)	0.0152 (18)	−0.0176 (18)

C1—O1	1.1961 (19)	C9—C10	1.376 (3)
C1—N1	1.405 (2)	C9—C14	1.377 (2)
C1—C2	1.485 (2)	C9—N1	1.425 (2)
C2—C3	1.374 (2)	C10—C11	1.379 (3)
C2—C7	1.375 (2)	C10—F2	1.390 (4)
C3—C4	1.389 (2)	C10—H10	0.942 (2)
C3—H3	0.9300	C11—C12	1.379 (3)
C4—C5	1.396 (3)	C11—H11	0.9300
C4—Cl1	1.7213 (17)	C12—C13	1.362 (3)
C5—C6	1.387 (3)	C12—H12	0.9300
C5—Cl2	1.7169 (17)	C13—C14	1.372 (3)
C6—C7	1.375 (2)	C13—H13	0.9300
C6—H6	0.9300	C14—F1	1.339 (3)
C7—C8	1.486 (2)	C14—H14	0.935 (2)
C8—O2	1.204 (2)	F1—H14	0.4311 (19)
C8—N1	1.395 (2)	F2—H10	0.509 (4)
O1—C1—N1	125.46 (15)	C10—C9—N1	121.51 (15)
O1—C1—C2	129.22 (15)	C14—C9—N1	119.33 (16)
N1—C1—C2	105.32 (13)	C9—C10—C11	120.04 (19)
C3—C2—C7	121.37 (15)	C9—C10—F2	113.1 (2)
C3—C2—C1	130.02 (15)	C11—C10—F2	125.8 (2)
C7—C2—C1	108.60 (14)	C9—C10—H10	121.51 (19)
C2—C3—C4	117.92 (16)	C11—C10—H10	118.4 (2)
C2—C3—H3	121.0	C10—C11—C12	119.7 (2)
C4—C3—H3	121.0	C10—C11—H11	120.1
C3—C4—C5	120.63 (16)	C12—C11—H11	120.1
C3—C4—Cl1	118.77 (14)	C13—C12—C11	120.6 (2)
C5—C4—Cl1	120.61 (13)	C13—C12—H12	119.7
C6—C5—C4	120.61 (15)	C11—C12—H12	119.7
C6—C5—Cl2	118.79 (14)	C12—C13—C14	119.4 (2)
C4—C5—Cl2	120.60 (14)	C12—C13—H13	120.3
C7—C6—C5	117.91 (16)	C14—C13—H13	120.3
C7—C6—H6	121.0	F1—C14—C13	122.1 (2)
C5—C6—H6	121.0	F1—C14—C9	116.75 (17)
C6—C7—C2	121.55 (16)	C13—C14—C9	121.1 (2)
C6—C7—C8	129.94 (15)	C13—C14—H14	116.5 (2)
C2—C7—C8	108.50 (14)	C9—C14—H14	122.33 (19)
O2—C8—N1	125.90 (17)	C8—N1—C1	111.95 (13)
O2—C8—C7	128.49 (16)	C8—N1—C9	124.52 (14)
N1—C8—C7	105.61 (14)	C1—N1—C9	123.45 (14)
C10—C9—C14	119.16 (17)
O1—C1—C2—C3	0.3 (3)	N1—C9—C10—C11	−179.04 (18)
N1—C1—C2—C3	−179.36 (16)	C14—C9—C10—F2	−168.5 (2)
O1—C1—C2—C7	179.79 (17)	N1—C9—C10—F2	11.8 (3)
N1—C1—C2—C7	0.13 (17)	C9—C10—C11—C12	−0.1 (3)
C7—C2—C3—C4	0.5 (2)	F2—C10—C11—C12	167.6 (3)
C1—C2—C3—C4	179.97 (15)	C10—C11—C12—C13	−0.2 (4)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—C14	−0.1 (4)
C2—C3—C4—Cl1	179.09 (12)	C12—C13—C14—F1	−175.6 (2)
C3—C4—C5—C6	0.6 (3)	C12—C13—C14—C9	0.7 (3)
Cl1—C4—C5—C6	−179.39 (13)	C10—C9—C14—F1	175.55 (19)
C3—C4—C5—Cl2	−179.33 (13)	N1—C9—C14—F1	−4.7 (3)
Cl1—C4—C5—Cl2	0.7 (2)	C10—C9—C14—C13	−1.0 (3)
C4—C5—C6—C7	0.1 (2)	N1—C9—C14—C13	178.76 (19)
Cl2—C5—C6—C7	−179.98 (12)	O2—C8—N1—C1	−178.75 (17)
C5—C6—C7—C2	−0.5 (2)	C7—C8—N1—C1	1.21 (18)
C5—C6—C7—C8	179.55 (16)	O2—C8—N1—C9	−1.9 (3)
C3—C2—C7—C6	0.2 (2)	C7—C8—N1—C9	178.08 (14)
C1—C2—C7—C6	−179.39 (14)	O1—C1—N1—C8	179.45 (16)
C3—C2—C7—C8	−179.87 (15)	C2—C1—N1—C8	−0.86 (17)
C1—C2—C7—C8	0.59 (18)	O1—C1—N1—C9	2.5 (3)
C6—C7—C8—O2	−1.2 (3)	C2—C1—N1—C9	−177.77 (14)
C2—C7—C8—O2	178.87 (17)	C10—C9—N1—C8	−62.0 (2)
C6—C7—C8—N1	178.88 (16)	C14—C9—N1—C8	118.29 (19)
C2—C7—C8—N1	−1.10 (18)	C10—C9—N1—C1	114.5 (2)
C14—C9—C10—C11	0.7 (3)	C14—C9—N1—C1	−65.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1i	0.93	2.99	3.844 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1i	0.93	2.99	3.844 (4)	153

Symmetry code: (i) . Cg1 is the centroid of atoms C2–C7.