2-(2-Iodo­ethyl)isoindole-1,3-dione

The title compound, C₁₀H₈INO₂, is an N-substituted phthalimide derivative in which the crystallographic inter­molecular contact pattern consists of I...I, C—H...I, C—H...O and aromatic π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.068
• wR factor = 0.162
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B   ..  O11     ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B   ..  I14     ..       3.07 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

2-(2-Iodoethyl)-isoindole-1,3-dione

Crystal data

C10H8INO2	F(000) = 576
Mr = 301.07	Dx = 2.017 Mg m^−3
Monoclinic, P21/n	Melting point: 373 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.1099 (11) Å	Cell parameters from 3291 reflections
b = 4.7775 (2) Å	θ = 0.4–27.9°
c = 15.9655 (14) Å	µ = 3.20 mm^−1
β = 97.556 (3)°	T = 173 K
V = 991.28 (13) Å^3	Block, colourless
Z = 4	0.30 × 0.15 × 0.07 mm

Data collection

Bruker Kappa-APEX-II diffractometer	2357 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
Detector resolution: 9 pixels mm^-1	θmax = 27.9°, θmin = 2.6°
φ and ω scans	h = −11→17
Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995; Spek, 2003)	k = −6→4
Tmin = 0.447, Tmax = 0.807	l = −20→21
4909 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 15.0376P] where P = (Fo^2 + 2Fc^2)/3
2357 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.88 e Å^−3
0 restraints	Δρmin = −1.45 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
I14	0.66567 (5)	0.32893 (13)	0.30460 (4)	0.0328 (2)
O10	0.8627 (5)	−0.0112 (15)	0.4658 (4)	0.0333 (14)
O11	0.5942 (4)	0.3645 (14)	0.5830 (4)	0.0306 (14)
N2	0.7109 (5)	0.1411 (15)	0.5095 (4)	0.0229 (14)
C1	0.8188 (6)	0.1383 (19)	0.5102 (5)	0.0261 (17)
C3	0.6808 (6)	0.3272 (16)	0.5682 (4)	0.0182 (14)
C4	0.7767 (6)	0.4659 (16)	0.6086 (5)	0.0213 (15)
C5	0.7920 (7)	0.6710 (18)	0.6702 (5)	0.0260 (17)
H5	0.7357	0.7487	0.6941	0.031*
C6	0.8918 (7)	0.7597 (19)	0.6962 (5)	0.0297 (19)
H6	0.9041	0.8998	0.7385	0.036*
C7	0.9740 (6)	0.6466 (17)	0.6611 (5)	0.0264 (17)
H7	1.0414	0.7140	0.6795	0.032*
C8	0.9608 (6)	0.4357 (19)	0.5993 (5)	0.0261 (17)
H8	1.0172	0.3555	0.5761	0.031*
C9	0.8595 (6)	0.3517 (17)	0.5742 (5)	0.0227 (16)
C12	0.6406 (6)	−0.0364 (18)	0.4555 (5)	0.0265 (17)
H12A	0.5948	−0.1336	0.4907	0.032*
H12B	0.6809	−0.1809	0.4299	0.032*
C13	0.5749 (6)	0.1204 (19)	0.3854 (5)	0.0268 (18)
H13A	0.5318	0.2591	0.4106	0.032*
H13B	0.5284	−0.0133	0.3519	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I14	0.0384 (3)	0.0324 (3)	0.0281 (3)	0.0011 (3)	0.0055 (2)	0.0010 (3)
O10	0.027 (3)	0.041 (4)	0.032 (3)	0.011 (3)	0.006 (3)	−0.004 (3)
O11	0.024 (3)	0.039 (4)	0.029 (3)	−0.001 (3)	0.007 (2)	−0.004 (3)
N2	0.019 (3)	0.026 (4)	0.024 (3)	0.004 (3)	0.002 (2)	0.000 (3)
C1	0.024 (4)	0.035 (5)	0.018 (3)	0.006 (4)	−0.004 (3)	0.005 (4)
C3	0.021 (3)	0.017 (3)	0.017 (3)	0.007 (3)	0.002 (3)	0.000 (3)
C4	0.026 (4)	0.017 (4)	0.022 (4)	0.000 (3)	0.005 (3)	0.003 (3)
C5	0.038 (4)	0.019 (4)	0.023 (4)	0.006 (4)	0.009 (3)	−0.001 (3)
C6	0.044 (5)	0.022 (4)	0.022 (4)	0.001 (4)	0.001 (4)	−0.002 (3)
C7	0.026 (4)	0.022 (4)	0.029 (4)	−0.005 (3)	−0.005 (3)	0.002 (3)
C8	0.021 (4)	0.032 (4)	0.026 (4)	0.001 (3)	0.003 (3)	0.003 (3)
C9	0.025 (4)	0.022 (4)	0.020 (4)	0.006 (3)	0.001 (3)	0.003 (3)
C12	0.026 (4)	0.021 (4)	0.031 (4)	−0.002 (3)	0.000 (3)	−0.004 (3)
C13	0.018 (3)	0.034 (5)	0.028 (4)	−0.004 (3)	0.000 (3)	−0.005 (4)

Geometric parameters (Å, º)

I14—C13	2.116 (9)	C6—C7	1.387 (13)
O10—C1	1.204 (10)	C6—H6	0.9500
O11—C3	1.203 (9)	C7—C8	1.405 (12)
N2—C3	1.386 (10)	C7—H7	0.9500
N2—C1	1.414 (10)	C8—C9	1.394 (11)
N2—C12	1.450 (10)	C8—H8	0.9500
C1—C9	1.492 (12)	C12—C13	1.518 (12)
C3—C4	1.490 (11)	C12—H12A	0.9900
C4—C5	1.384 (11)	C12—H12B	0.9900
C4—C9	1.391 (11)	C13—H13A	0.9900
C5—C6	1.386 (13)	C13—H13B	0.9900
C5—H5	0.9500
I14···I14^i	3.8275 (9)
C3—N2—C1	112.0 (7)	C8—C7—H7	118.9
C3—N2—C12	124.2 (6)	C9—C8—C7	115.6 (8)
C1—N2—C12	123.8 (7)	C9—C8—H8	122.2
O10—C1—N2	123.8 (8)	C7—C8—H8	122.2
O10—C1—C9	130.7 (8)	C4—C9—C8	122.5 (8)
N2—C1—C9	105.5 (7)	C4—C9—C1	108.1 (7)
O11—C3—N2	125.9 (7)	C8—C9—C1	129.4 (7)
O11—C3—C4	127.9 (7)	N2—C12—C13	113.9 (7)
N2—C3—C4	106.2 (6)	N2—C12—H12A	108.8
C5—C4—C9	120.6 (8)	C13—C12—H12A	108.8
C5—C4—C3	131.1 (7)	N2—C12—H12B	108.8
C9—C4—C3	108.2 (7)	C13—C12—H12B	108.8
C4—C5—C6	118.2 (8)	H12A—C12—H12B	107.7
C4—C5—H5	120.9	C12—C13—I14	111.8 (5)
C6—C5—H5	120.9	C12—C13—H13A	109.3
C5—C6—C7	120.8 (8)	I14—C13—H13A	109.3
C5—C6—H6	119.6	C12—C13—H13B	109.3
C7—C6—H6	119.6	I14—C13—H13B	109.3
C6—C7—C8	122.2 (8)	H13A—C13—H13B	107.9
C6—C7—H7	118.9
C3—N2—C1—O10	178.5 (8)	C5—C6—C7—C8	−1.1 (13)
C12—N2—C1—O10	0.2 (13)	C6—C7—C8—C9	1.3 (12)
C3—N2—C1—C9	−1.9 (9)	C5—C4—C9—C8	−0.1 (12)
C12—N2—C1—C9	179.9 (7)	C3—C4—C9—C8	−179.5 (7)
C1—N2—C3—O11	−177.4 (8)	C5—C4—C9—C1	180.0 (7)
C12—N2—C3—O11	0.9 (13)	C3—C4—C9—C1	0.6 (9)
C1—N2—C3—C4	2.2 (9)	C7—C8—C9—C4	−0.7 (12)
C12—N2—C3—C4	−179.5 (7)	C7—C8—C9—C1	179.2 (8)
O11—C3—C4—C5	−1.4 (14)	O10—C1—C9—C4	−179.6 (9)
N2—C3—C4—C5	179.0 (8)	N2—C1—C9—C4	0.7 (9)
O11—C3—C4—C9	177.9 (8)	O10—C1—C9—C8	0.4 (15)
N2—C3—C4—C9	−1.7 (8)	N2—C1—C9—C8	−179.2 (8)
C9—C4—C5—C6	0.4 (12)	C3—N2—C12—C13	72.3 (10)
C3—C4—C5—C6	179.6 (8)	C1—N2—C12—C13	−109.7 (9)
C4—C5—C6—C7	0.2 (13)	N2—C12—C13—I14	59.8 (8)

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O10	0.99	2.51	2.896 (10)	103
C13—H13B···O11^ii	0.99	2.63	3.291 (10)	124
C13—H13A···O11^iii	0.99	2.45	3.393 (11)	159
C8—H8···O10^iv	0.95	2.43	3.344 (11)	161
C12—H12B···I14^v	0.99	3.07	3.913 (8)	144

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y, −z+1; (v) x, y−1, z.