2-(2-Iodo-phen-yl)isoindoline-1,3-dione.

In the title compound, C(14)H(8)INO(2), the dihedral angle between the isoindole ring and the phenyl ring of the 1-iodo-benzene group is 84.77 (15)°. There is a short inter-molecular I⋯O contact of 3.068 (3) Å in the crystal.

Related literature

For the biological activity of phthalimides, see: Kerrigan et al. (2000 ▶); Lima et al. (2002 ▶). For the crystal structures of phthalimide derivatives, see: Devarajegowda et al. (2010 ▶); Sakthivel et al. (2007a ▶,b ▶); Nagaraj et al. (2005 ▶).

Experimental

Crystal data

C14H8INO2

M = 349.11

Monoclinic,

a = 11.5318 (5) Å

b = 8.0597 (2) Å

c = 15.6134 (7) Å

β = 118.157 (3)°

V = 1279.42 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.50 mm−1

T = 296 K

0.69 × 0.51 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.291, T max = 0.590

13075 measured reflections

2517 independent reflections

2434 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.11

2517 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −1.05 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: WinGX (Farrugia, 1999 ▶) and SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: WinGX (Farrugia, 1999 ▶) and SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006544/lw2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006544/lw2057Isup2.hkl

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

C14H8INO2	F(000) = 672
Mr = 349.11	Dx = 1.812 Mg m−3
Monoclinic, P21/c	Melting point: 455 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.5318 (5) Å	Cell parameters from 26549 reflections
b = 8.0597 (2) Å	θ = 1.8–28.0°
c = 15.6134 (7) Å	µ = 2.50 mm−1
β = 118.157 (3)°	T = 296 K
V = 1279.42 (9) Å3	Prism, red
Z = 4	0.69 × 0.51 × 0.28 mm

Stoe IPDS 2 diffractometer	2517 independent reflections
Radiation source: fine-focus sealed tube	2434 reflections with I > 2σ(I)
plane graphite	Rint = 0.033
rotation method scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −14→14
Tmin = 0.291, Tmax = 0.590	k = −9→9
13075 measured reflections	l = −19→19

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0373P)2 + 1.3378P] where P = (Fo2 + 2Fc2)/3
2517 reflections	(Δ/σ)max = 0.002
163 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −1.05 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
C1	0.6644 (3)	0.2407 (4)	0.1170 (2)	0.0391 (6)
C2	0.6487 (3)	0.3409 (4)	0.1906 (2)	0.0388 (6)
C3	0.5850 (3)	0.4891 (4)	0.1819 (2)	0.0500 (7)
H3	0.5418	0.5438	0.1225	0.060*
C4	0.5880 (4)	0.5537 (5)	0.2652 (3)	0.0581 (8)
H4	0.5485	0.6557	0.2622	0.070*
C5	0.6482 (4)	0.4699 (5)	0.3524 (3)	0.0588 (9)
H5	0.6469	0.5156	0.4066	0.071*
C6	0.7105 (4)	0.3194 (4)	0.3610 (2)	0.0535 (8)
H6	0.7506	0.2624	0.4197	0.064*
C7	0.7105 (3)	0.2578 (4)	0.2786 (2)	0.0405 (6)
C8	0.7669 (3)	0.1017 (4)	0.2642 (2)	0.0445 (6)
C9	0.7720 (3)	−0.0319 (3)	0.12144 (19)	0.0392 (6)
C10	0.8848 (3)	−0.0215 (4)	0.1120 (2)	0.0425 (6)
C11	0.9183 (4)	−0.1504 (5)	0.0691 (2)	0.0540 (8)
H11	0.9939	−0.1433	0.0621	0.065*
C12	0.8393 (5)	−0.2892 (4)	0.0369 (3)	0.0630 (10)
H12	0.8621	−0.3762	0.0087	0.076*
C13	0.7274 (5)	−0.2994 (4)	0.0464 (3)	0.0627 (10)
H13	0.6744	−0.3933	0.0243	0.075*
C14	0.6924 (4)	−0.1705 (4)	0.0887 (3)	0.0527 (8)
H14	0.6162	−0.1774	0.0949	0.063*
I1	1.00579 (2)	0.18859 (3)	0.158933 (17)	0.06096 (11)
N1	0.7345 (2)	0.0987 (3)	0.16550 (16)	0.0399 (5)
O1	0.6253 (2)	0.2689 (3)	0.03201 (15)	0.0534 (5)
O2	0.8266 (3)	−0.0042 (3)	0.32190 (18)	0.0722 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0420 (14)	0.0404 (14)	0.0373 (14)	0.0006 (12)	0.0207 (12)	0.0023 (12)
C2	0.0407 (14)	0.0423 (14)	0.0353 (13)	0.0008 (11)	0.0196 (12)	0.0009 (11)
C3	0.0539 (17)	0.0491 (17)	0.0505 (16)	0.0086 (14)	0.0277 (14)	0.0063 (14)
C4	0.060 (2)	0.0550 (19)	0.065 (2)	0.0098 (16)	0.0335 (17)	−0.0071 (16)
C5	0.0586 (19)	0.071 (2)	0.0498 (17)	0.0052 (17)	0.0283 (16)	−0.0170 (16)
C6	0.0536 (18)	0.070 (2)	0.0362 (15)	0.0082 (15)	0.0204 (14)	−0.0010 (14)
C7	0.0411 (14)	0.0462 (15)	0.0354 (13)	0.0040 (12)	0.0192 (12)	0.0000 (12)
C8	0.0501 (16)	0.0492 (17)	0.0353 (13)	0.0087 (13)	0.0211 (12)	0.0053 (12)
C9	0.0462 (15)	0.0376 (14)	0.0340 (13)	0.0001 (11)	0.0191 (12)	−0.0003 (11)
C10	0.0453 (15)	0.0443 (15)	0.0374 (14)	−0.0020 (12)	0.0191 (12)	−0.0035 (12)
C11	0.0600 (19)	0.0583 (19)	0.0499 (17)	0.0068 (16)	0.0309 (16)	−0.0063 (15)
C12	0.089 (3)	0.0476 (18)	0.058 (2)	0.0041 (17)	0.039 (2)	−0.0110 (15)
C13	0.087 (3)	0.0417 (17)	0.061 (2)	−0.0143 (17)	0.037 (2)	−0.0098 (15)
C14	0.064 (2)	0.0464 (17)	0.0532 (18)	−0.0091 (14)	0.0324 (16)	−0.0014 (14)
I1	0.05713 (16)	0.06921 (18)	0.05964 (17)	−0.02284 (10)	0.03011 (12)	−0.02193 (10)
N1	0.0480 (13)	0.0408 (12)	0.0341 (11)	0.0045 (10)	0.0222 (10)	0.0021 (9)
O1	0.0687 (15)	0.0578 (13)	0.0354 (11)	0.0109 (11)	0.0259 (11)	0.0079 (10)
O2	0.102 (2)	0.0705 (16)	0.0473 (13)	0.0420 (16)	0.0381 (14)	0.0217 (12)

C1—O1	1.204 (3)	C8—O2	1.196 (4)
C1—N1	1.399 (4)	C8—N1	1.403 (3)
C1—C2	1.485 (4)	C9—C10	1.379 (4)
C2—C3	1.374 (4)	C9—C14	1.382 (4)
C2—C7	1.385 (4)	C9—N1	1.432 (4)
C3—C4	1.387 (5)	C10—C11	1.385 (4)
C3—H3	0.9300	C10—I1	2.094 (3)
C4—C5	1.377 (5)	C11—C12	1.379 (5)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.384 (5)	C12—C13	1.369 (6)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.379 (4)	C13—C14	1.390 (5)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.481 (4)	C14—H14	0.9300
O1—C1—N1	124.8 (3)	N1—C8—C7	105.8 (2)
O1—C1—C2	129.2 (3)	C10—C9—C14	120.4 (3)
N1—C1—C2	106.0 (2)	C10—C9—N1	121.4 (3)
C3—C2—C7	121.3 (3)	C14—C9—N1	118.2 (3)
C3—C2—C1	130.5 (3)	C9—C10—C11	119.9 (3)
C7—C2—C1	108.1 (2)	C9—C10—I1	121.2 (2)
C2—C3—C4	117.2 (3)	C11—C10—I1	118.9 (2)
C2—C3—H3	121.4	C12—C11—C10	119.8 (3)
C4—C3—H3	121.4	C12—C11—H11	120.1
C5—C4—C3	121.4 (3)	C10—C11—H11	120.1
C5—C4—H4	119.3	C13—C12—C11	120.2 (3)
C3—C4—H4	119.3	C13—C12—H12	119.9
C4—C5—C6	121.5 (3)	C11—C12—H12	119.9
C4—C5—H5	119.3	C12—C13—C14	120.4 (3)
C6—C5—H5	119.3	C12—C13—H13	119.8
C7—C6—C5	117.0 (3)	C14—C13—H13	119.8
C7—C6—H6	121.5	C9—C14—C13	119.2 (3)
C5—C6—H6	121.5	C9—C14—H14	120.4
C6—C7—C2	121.6 (3)	C13—C14—H14	120.4
C6—C7—C8	129.9 (3)	C1—N1—C8	111.5 (2)
C2—C7—C8	108.5 (2)	C1—N1—C9	124.7 (2)
O2—C8—N1	125.1 (3)	C8—N1—C9	123.7 (2)
O2—C8—C7	129.0 (3)
O1—C1—C2—C3	1.0 (6)	C14—C9—C10—I1	179.0 (2)
N1—C1—C2—C3	−178.1 (3)	N1—C9—C10—I1	−1.4 (4)
O1—C1—C2—C7	180.0 (3)	C9—C10—C11—C12	−0.6 (5)
N1—C1—C2—C7	0.9 (3)	I1—C10—C11—C12	−179.4 (3)
C7—C2—C3—C4	1.5 (5)	C10—C11—C12—C13	0.6 (6)
C1—C2—C3—C4	−179.7 (3)	C11—C12—C13—C14	−0.2 (6)
C2—C3—C4—C5	−2.2 (5)	C10—C9—C14—C13	0.1 (5)
C3—C4—C5—C6	1.3 (6)	N1—C9—C14—C13	−179.5 (3)
C4—C5—C6—C7	0.5 (6)	C12—C13—C14—C9	−0.2 (6)
C5—C6—C7—C2	−1.2 (5)	O1—C1—N1—C8	179.7 (3)
C5—C6—C7—C8	−179.4 (3)	C2—C1—N1—C8	−1.2 (3)
C3—C2—C7—C6	0.3 (5)	O1—C1—N1—C9	1.3 (5)
C1—C2—C7—C6	−178.8 (3)	C2—C1—N1—C9	−179.6 (3)
C3—C2—C7—C8	178.8 (3)	O2—C8—N1—C1	−180.0 (3)
C1—C2—C7—C8	−0.3 (3)	C7—C8—N1—C1	1.0 (3)
C6—C7—C8—O2	−1.0 (6)	O2—C8—N1—C9	−1.5 (5)
C2—C7—C8—O2	−179.4 (4)	C7—C8—N1—C9	179.4 (3)
C6—C7—C8—N1	178.0 (3)	C10—C9—N1—C1	84.2 (4)
C2—C7—C8—N1	−0.4 (3)	C14—C9—N1—C1	−96.2 (3)
C14—C9—C10—C11	0.3 (4)	C10—C9—N1—C8	−94.1 (4)
N1—C9—C10—C11	179.9 (3)	C14—C9—N1—C8	85.6 (4)