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

Demirtaş, G.; Dege, N.; Alaman Ağar, A.; Büyükgüngör, O.

doi:10.1107/S1600536811006544

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o857

doi:10.1107/S1600536811006544

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

Güneş Demirtaş,^a ^* Necmi Dege,^a Ayşen Alaman Ağar ^b and Orhan Büyükgüngör ^a

^aOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and ^bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Chemistry, 55139 Samsun, Turkey
^*Correspondence e-mail: gunesd@omu.edu.tr

(Received 18 February 2011; accepted 21 February 2011; online 12 March 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.031
wR(F²) = 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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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 (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	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.

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

Crystal data top

C₁₄H₈INO₂	F(000) = 672
M_r = 349.11	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0373P)² + 1.3378P] where P = (F_o² + 2F_c²)/3
2517 reflections	(Δ/σ)_max = 0.002
163 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

C₁₄H₈INO₂	V = 1279.42 (9) Å³
M_r = 349.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5318 (5) Å	µ = 2.50 mm⁻¹
b = 8.0597 (2) Å	T = 296 K
c = 15.6134 (7) Å	0.69 × 0.51 × 0.28 mm
β = 118.157 (3)°

Data collection top

Stoe IPDS 2 diffractometer	2517 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2434 reflections with I > 2σ(I)
T_min = 0.291, T_max = 0.590	R_int = 0.033
13075 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.11	Δρ_max = 0.82 e Å⁻³
2517 reflections	Δρ_min = −1.05 e Å⁻³
163 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₄H₈INO₂
M_r	349.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.5318 (5), 8.0597 (2), 15.6134 (7)
β (°)	118.157 (3)
V (Å³)	1279.42 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.50
Crystal size (mm)	0.69 × 0.51 × 0.28

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.291, 0.590
No. of measured, independent and observed [I > 2σ(I)] reflections	13075, 2517, 2434
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.11
No. of reflections	2517
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −1.05

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), WinGX (Farrugia, 1999) and SHELXS97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Acknowledgements

The authors thanks the Ondokuz Mayis University Research Fund for financial support of this project.

References

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