2-(2-Iodo­phen­yl)isoindoline-1,3-dione

Abstract

In the title compound, C₁₄H₈INO₂, the dihedral angle between the isoindole ring and the phenyl ring of the 1-iodo­benzene group is 84.77 (15)°. There is a short inter­molecular 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 _r = 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) ų

• 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

• Δρ_max = 0.82 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

supplementary crystallographic information

Comment

The importance of the biological activity of the phthalimide group with reference to N-2-Iodophenylphthalimide is described by Kerrigan et al., (2000) and Lima et al., (2002).

The C—C bond distances are 1.485 (4) Å for C1—C2 and 1.481 (4)Å for C7—C8. The bond distances between carbon atoms in the aromatic rings range from 1.369 (6)Å to 1.390 (5)Å. The C1=O1 and C8=O2 bond distances are 1.204 (3)Å and 1.196 (4)Å, respectively. The N—C bond distances range from 1.399 (4) Å to 1.432 (4)Å. These values are consistent with those reported in the literature (Devarajegowda et al., 2010; Sakthivel et al., 2007a; Sakthivel et al.2007b; Nagaraj et al., 2005). C10—I1 bond distance is 2.094 (3) Å. An intermolecular I1···O2 contact of 3.068 (3)Å is present in the crystal.

Experimental

The compound N-2-Iodophenylphthalimide was prepared by refluxing a mixture of a solution containing N-hydroxyphthalimide (0.0113 g 0.069 mmol) in 20 ml ethanol and a solution containing 4-amino-4-methylphenol (0.0303 g 0.069 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1h under reflux. The crystals of N-2-Iodophenylphthalimide suitable for X-ray analysis were obtained from ethyl alcohol by slow evaporation (yield % 41; m.p 180.3–184.0 ^oC).

Refinement

All hydrogen atoms were positioned geometrically (C—H=0.93 Å) and treated as riding with U_iso(H)=1.1U_eq(C).

Figures

Fig. 1.

The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 2.

The crystal packing of the title compound in the unit cell.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)