1-Ethyl-5-iodo-indoline-2,3-dione.

There are two independent mol-ecules in the asymmetric unit of the title compound, C10H8INO2, which differ in the degree of planarity. The iodo-indoline-2,3-dione skeleton of mol-ecule 1 is essentially planar [mean deviation = 0.003 (2) Å for the nine non-H atoms of the indoline core, with a maximum deviation of 0.033 (1) Å for the I atom]. The I atom and O atom in the 3-position of mol-ecule 2 deviate by 0.195 (1) and 0.120 (2) Å, respectively, from the least-squares plane through the nine non-H atoms of the indoline core. Mol-ecules 1 and 2 are roughly coplanar, the mean planes through their cores making a dihedral angle of 6.84 (1)°. This coplanarity results in a layer-like structure parallel to (6,11,17) in the crystal, the distance between adjacent least-squares planes through the cores of mol-ecules 1 and 2 being 3.37 (1) Å. In such a layer, mol-ecules 1 and 2 are linked by C-H⋯O hydrogen bonds, forming chains along [11-1]. The chains are further coupled to construct a kind of double-chain structure via I⋯O inter-actions [3.270 (2) Å].

Related literature

For applications of indoline-2,3-dione in drug design, see: Silva et al. (2001 ▶). For the synthesis of the title compound, see: Ji et al. (2010 ▶). For related structures, see: Garden et al. (2006 ▶); Abid et al. (2008 ▶); Kurkin et al. (2008 ▶).

Experimental

Crystal data

C10H8INO2

M = 301.07

Triclinic,

a = 9.9658 (2) Å

b = 10.1453 (2) Å

c = 11.3007 (2) Å

α = 71.188 (1)°

β = 72.599 (1)°

γ = 84.434 (1)°

V = 1032.04 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.08 mm−1

T = 295 K

0.27 × 0.21 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.490, T max = 0.746

13515 measured reflections

5091 independent reflections

4358 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.066

S = 1.01

5091 reflections

279 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813033539/vm2202sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033539/vm2202Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033539/vm2202Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H8INO2	Z = 4
Mr = 301.07	F(000) = 576
Triclinic, P1	Dx = 1.938 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9658 (2) Å	Cell parameters from 7943 reflections
b = 10.1453 (2) Å	θ = 2.4–28.7°
c = 11.3007 (2) Å	µ = 3.08 mm−1
α = 71.188 (1)°	T = 295 K
β = 72.599 (1)°	Plank, orange
γ = 84.434 (1)°	0.27 × 0.21 × 0.10 mm
V = 1032.04 (3) Å3

Bruker APEXII CCD diffractometer	5091 independent reflections
Radiation source: fine-focus sealed tube	4358 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.3 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.490, Tmax = 0.746	l = −15→13
13515 measured reflections

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)] = 0.023	Hydrogen site location: mixed
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.529P] where P = (Fo2 + 2Fc2)/3
5091 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. Scan width 0.5° ω and φ, Crystal to detector distance 5.964 cm, exposure time 20 s, 19 h for data collection

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
I1	−0.188160 (18)	0.385210 (17)	0.659889 (17)	0.05692 (6)
I2	1.215992 (18)	0.17083 (2)	0.320573 (19)	0.06423 (7)
O1	0.1685 (2)	−0.30982 (18)	0.98576 (18)	0.0606 (5)
O2	−0.12166 (19)	−0.20187 (18)	1.00153 (18)	0.0587 (4)
O4	0.5791 (2)	0.1463 (2)	0.5519 (2)	0.0810 (7)
O3	0.41994 (19)	0.3947 (2)	0.4463 (2)	0.0673 (5)
N1	0.22397 (19)	−0.09288 (18)	0.83363 (18)	0.0448 (4)
C29	0.6039 (3)	0.5967 (3)	0.2206 (3)	0.0574 (6)
H29A	0.6799	0.6622	0.1950	0.069*
H29B	0.5200	0.6337	0.2693	0.069*
C5	−0.0444 (2)	0.2289 (2)	0.7122 (2)	0.0451 (5)
C6	0.0995 (3)	0.2509 (2)	0.6564 (2)	0.0492 (5)
C7	0.1973 (2)	0.1495 (2)	0.6900 (2)	0.0476 (5)
C8	0.1470 (2)	0.0250 (2)	0.7828 (2)	0.0408 (4)
C9	0.3765 (2)	−0.1004 (3)	0.8019 (3)	0.0521 (5)
H9A	0.4165	−0.0557	0.7092	0.063*
H9B	0.4054	−0.1973	0.8216	0.063*
C10	0.4329 (3)	−0.0314 (4)	0.8766 (3)	0.0731 (8)
H10A	0.3986	0.0625	0.8625	0.110*
H10B	0.5338	−0.0306	0.8470	0.110*
H10C	0.4023	−0.0820	0.9679	0.110*
C1	0.1354 (3)	−0.1967 (2)	0.9239 (2)	0.0453 (5)
C2	−0.0166 (2)	−0.1390 (2)	0.9316 (2)	0.0444 (5)
C3	0.0021 (2)	0.0023 (2)	0.8392 (2)	0.0409 (4)
C4	−0.0948 (2)	0.1026 (2)	0.8047 (2)	0.0441 (5)
C25	1.0250 (2)	0.2682 (2)	0.3052 (2)	0.0456 (5)
C24	0.9007 (3)	0.2058 (2)	0.3914 (2)	0.0492 (5)
C23	0.7765 (2)	0.2774 (2)	0.3829 (2)	0.0439 (5)
C28	0.7764 (2)	0.4083 (2)	0.2908 (2)	0.0404 (4)
N2	0.63970 (19)	0.4636 (2)	0.30430 (19)	0.0467 (4)
C30	0.5792 (4)	0.5831 (4)	0.1017 (3)	0.0877 (11)
H30A	0.6629	0.5489	0.0519	0.132*
H30B	0.5553	0.6724	0.0498	0.132*
H30C	0.5034	0.5191	0.1265	0.132*
C22	0.6307 (3)	0.2473 (3)	0.4615 (2)	0.0536 (6)
C21	0.5455 (2)	0.3764 (3)	0.4059 (2)	0.0514 (5)
C27	0.9001 (2)	0.4696 (2)	0.2032 (2)	0.0461 (5)
C26	1.0245 (2)	0.3975 (2)	0.2122 (2)	0.0468 (5)
H4	−0.189 (3)	0.089 (3)	0.843 (2)	0.046 (6)*
H6	0.132 (3)	0.339 (3)	0.596 (3)	0.055 (7)*
H7	0.299 (3)	0.166 (3)	0.650 (3)	0.050 (7)*
H26	1.110 (3)	0.439 (3)	0.149 (3)	0.055 (7)*
H27	0.897 (3)	0.557 (3)	0.142 (3)	0.052 (7)*
H24	0.903 (3)	0.124 (3)	0.449 (3)	0.055 (7)*

	U11	U22	U33	U12	U13	U23
I1	0.05293 (10)	0.05269 (10)	0.06295 (11)	0.00741 (7)	−0.02024 (8)	−0.01363 (8)
I2	0.04713 (10)	0.07268 (13)	0.07074 (12)	0.01030 (8)	−0.01917 (8)	−0.02004 (9)
O1	0.0694 (12)	0.0412 (9)	0.0596 (10)	0.0013 (8)	−0.0147 (9)	−0.0037 (8)
O2	0.0541 (10)	0.0492 (9)	0.0564 (10)	−0.0162 (8)	−0.0007 (8)	−0.0034 (8)
O4	0.0520 (11)	0.0725 (13)	0.0778 (14)	−0.0168 (10)	−0.0029 (10)	0.0214 (11)
O3	0.0382 (9)	0.0733 (13)	0.0721 (12)	−0.0045 (8)	−0.0035 (8)	−0.0080 (10)
N1	0.0424 (10)	0.0391 (9)	0.0449 (10)	−0.0014 (7)	−0.0058 (8)	−0.0079 (8)
C29	0.0451 (13)	0.0429 (12)	0.0678 (16)	0.0045 (10)	−0.0062 (11)	−0.0056 (11)
C5	0.0458 (12)	0.0415 (11)	0.0449 (11)	0.0021 (9)	−0.0113 (9)	−0.0113 (9)
C6	0.0475 (12)	0.0407 (11)	0.0457 (12)	−0.0062 (9)	−0.0040 (9)	−0.0016 (9)
C7	0.0402 (11)	0.0448 (11)	0.0442 (11)	−0.0079 (9)	−0.0003 (9)	−0.0040 (9)
C8	0.0409 (10)	0.0389 (10)	0.0373 (10)	−0.0038 (8)	−0.0053 (8)	−0.0093 (8)
C9	0.0407 (11)	0.0510 (12)	0.0557 (13)	0.0068 (10)	−0.0043 (10)	−0.0152 (11)
C10	0.0457 (14)	0.097 (2)	0.086 (2)	0.0070 (14)	−0.0178 (14)	−0.0434 (18)
C1	0.0527 (13)	0.0380 (10)	0.0417 (11)	−0.0038 (9)	−0.0080 (9)	−0.0115 (9)
C2	0.0485 (12)	0.0391 (10)	0.0400 (10)	−0.0090 (9)	−0.0041 (9)	−0.0097 (9)
C3	0.0411 (11)	0.0373 (10)	0.0394 (10)	−0.0070 (8)	−0.0045 (8)	−0.0098 (8)
C4	0.0380 (11)	0.0454 (11)	0.0442 (11)	−0.0059 (9)	−0.0036 (9)	−0.0136 (9)
C25	0.0407 (11)	0.0471 (11)	0.0472 (11)	0.0010 (9)	−0.0094 (9)	−0.0151 (9)
C24	0.0499 (13)	0.0404 (11)	0.0476 (12)	−0.0034 (9)	−0.0104 (10)	−0.0027 (10)
C23	0.0414 (11)	0.0421 (11)	0.0403 (10)	−0.0076 (8)	−0.0052 (8)	−0.0058 (9)
C28	0.0401 (11)	0.0375 (10)	0.0388 (10)	−0.0039 (8)	−0.0059 (8)	−0.0094 (8)
N2	0.0378 (9)	0.0440 (9)	0.0481 (10)	−0.0031 (7)	−0.0045 (8)	−0.0067 (8)
C30	0.087 (2)	0.101 (3)	0.0606 (18)	0.025 (2)	−0.0243 (16)	−0.0097 (18)
C22	0.0448 (12)	0.0535 (13)	0.0496 (13)	−0.0112 (10)	−0.0068 (10)	−0.0017 (10)
C21	0.0404 (12)	0.0558 (13)	0.0505 (12)	−0.0079 (10)	−0.0050 (9)	−0.0115 (11)
C27	0.0435 (12)	0.0392 (11)	0.0445 (11)	−0.0066 (9)	−0.0032 (9)	−0.0047 (9)
C26	0.0394 (11)	0.0457 (11)	0.0464 (11)	−0.0057 (9)	−0.0011 (9)	−0.0108 (9)

I1—C5	2.092 (2)	C10—H10A	0.9600
I2—C25	2.086 (2)	C10—H10B	0.9600
O1—C1	1.209 (3)	C10—H10C	0.9600
O2—C2	1.198 (3)	C1—C2	1.558 (3)
O4—C22	1.213 (3)	C2—C3	1.467 (3)
O3—C21	1.215 (3)	C3—C4	1.378 (3)
N1—C1	1.371 (3)	C4—H4	0.91 (3)
N1—C8	1.411 (3)	C25—C24	1.384 (3)
N1—C9	1.454 (3)	C25—C26	1.392 (3)
C29—N2	1.459 (3)	C24—C23	1.386 (3)
C29—C30	1.486 (5)	C24—H24	0.88 (3)
C29—H29A	0.9700	C23—C28	1.399 (3)
C29—H29B	0.9700	C23—C22	1.460 (3)
C5—C4	1.391 (3)	C28—C27	1.381 (3)
C5—C6	1.391 (3)	C28—N2	1.406 (3)
C6—C7	1.388 (3)	N2—C21	1.358 (3)
C6—H6	0.95 (3)	C30—H30A	0.9600
C7—C8	1.378 (3)	C30—H30B	0.9600
C7—H7	0.99 (3)	C30—H30C	0.9600
C8—C3	1.401 (3)	C22—C21	1.551 (4)
C9—C10	1.503 (4)	C27—C26	1.391 (3)
C9—H9A	0.9700	C27—H27	0.93 (3)
C9—H9B	0.9700	C26—H26	0.96 (3)
C1—N1—C8	110.78 (18)	C4—C3—C8	121.64 (19)
C1—N1—C9	124.24 (19)	C4—C3—C2	131.1 (2)
C8—N1—C9	124.86 (18)	C8—C3—C2	107.30 (19)
N2—C29—C30	112.1 (2)	C3—C4—C5	117.8 (2)
N2—C29—H29A	109.2	C3—C4—H4	121.8 (16)
C30—C29—H29A	109.2	C5—C4—H4	120.4 (16)
N2—C29—H29B	109.2	C24—C25—C26	121.0 (2)
C30—C29—H29B	109.2	C24—C25—I2	119.38 (17)
H29A—C29—H29B	107.9	C26—C25—I2	119.59 (17)
C4—C5—C6	120.3 (2)	C25—C24—C23	117.7 (2)
C4—C5—I1	118.94 (17)	C25—C24—H24	119.6 (18)
C6—C5—I1	120.75 (16)	C23—C24—H24	122.7 (18)
C7—C6—C5	122.0 (2)	C24—C23—C28	121.3 (2)
C7—C6—H6	118.8 (17)	C24—C23—C22	132.1 (2)
C5—C6—H6	119.2 (17)	C28—C23—C22	106.5 (2)
C8—C7—C6	117.6 (2)	C27—C28—C23	121.1 (2)
C8—C7—H7	121.0 (16)	C27—C28—N2	127.6 (2)
C6—C7—H7	121.5 (16)	C23—C28—N2	111.23 (18)
C7—C8—C3	120.7 (2)	C21—N2—C28	110.83 (18)
C7—C8—N1	128.4 (2)	C21—N2—C29	124.6 (2)
C3—C8—N1	110.93 (18)	C28—N2—C29	124.59 (18)
N1—C9—C10	112.0 (2)	C29—C30—H30A	109.5
N1—C9—H9A	109.2	C29—C30—H30B	109.5
C10—C9—H9A	109.2	H30A—C30—H30B	109.5
N1—C9—H9B	109.2	C29—C30—H30C	109.5
C10—C9—H9B	109.2	H30A—C30—H30C	109.5
H9A—C9—H9B	107.9	H30B—C30—H30C	109.5
C9—C10—H10A	109.5	O4—C22—C23	130.6 (3)
C9—C10—H10B	109.5	O4—C22—C21	124.0 (2)
H10A—C10—H10B	109.5	C23—C22—C21	105.38 (19)
C9—C10—H10C	109.5	O3—C21—N2	127.6 (2)
H10A—C10—H10C	109.5	O3—C21—C22	126.4 (2)
H10B—C10—H10C	109.5	N2—C21—C22	105.98 (19)
O1—C1—N1	126.9 (2)	C28—C27—C26	117.4 (2)
O1—C1—C2	127.0 (2)	C28—C27—H27	119.1 (17)
N1—C1—C2	106.10 (18)	C26—C27—H27	123.5 (17)
O2—C2—C3	130.5 (2)	C27—C26—C25	121.5 (2)
O2—C2—C1	124.6 (2)	C27—C26—H26	116.9 (17)
C3—C2—C1	104.89 (18)	C25—C26—H26	121.6 (17)
C4—C5—C6—C7	−0.1 (4)	C26—C25—C24—C23	−0.8 (4)
I1—C5—C6—C7	179.48 (19)	I2—C25—C24—C23	176.44 (18)
C5—C6—C7—C8	−0.7 (4)	C25—C24—C23—C28	−0.2 (4)
C6—C7—C8—C3	0.7 (4)	C25—C24—C23—C22	−175.8 (3)
C6—C7—C8—N1	−179.6 (2)	C24—C23—C28—C27	1.4 (4)
C1—N1—C8—C7	−179.6 (2)	C22—C23—C28—C27	177.9 (2)
C9—N1—C8—C7	4.4 (4)	C24—C23—C28—N2	−177.2 (2)
C1—N1—C8—C3	0.1 (3)	C22—C23—C28—N2	−0.6 (3)
C9—N1—C8—C3	−175.9 (2)	C27—C28—N2—C21	−176.6 (2)
C1—N1—C9—C10	−95.9 (3)	C23—C28—N2—C21	1.9 (3)
C8—N1—C9—C10	79.5 (3)	C27—C28—N2—C29	3.4 (4)
C8—N1—C1—O1	−179.3 (2)	C23—C28—N2—C29	−178.2 (2)
C9—N1—C1—O1	−3.2 (4)	C30—C29—N2—C21	−93.7 (3)
C8—N1—C1—C2	0.2 (2)	C30—C29—N2—C28	86.3 (3)
C9—N1—C1—C2	176.3 (2)	C24—C23—C22—O4	−4.6 (5)
O1—C1—C2—O2	−0.2 (4)	C28—C23—C22—O4	179.4 (3)
N1—C1—C2—O2	−179.7 (2)	C24—C23—C22—C21	175.4 (3)
O1—C1—C2—C3	179.0 (2)	C28—C23—C22—C21	−0.7 (3)
N1—C1—C2—C3	−0.5 (2)	C28—N2—C21—O3	177.6 (3)
C7—C8—C3—C4	−0.1 (3)	C29—N2—C21—O3	−2.3 (4)
N1—C8—C3—C4	−179.8 (2)	C28—N2—C21—C22	−2.2 (3)
C7—C8—C3—C2	179.3 (2)	C29—N2—C21—C22	177.9 (2)
N1—C8—C3—C2	−0.4 (2)	O4—C22—C21—O3	1.9 (5)
O2—C2—C3—C4	−0.9 (4)	C23—C22—C21—O3	−178.0 (3)
C1—C2—C3—C4	179.9 (2)	O4—C22—C21—N2	−178.3 (3)
O2—C2—C3—C8	179.7 (3)	C23—C22—C21—N2	1.7 (3)
C1—C2—C3—C8	0.5 (2)	C23—C28—C27—C26	−1.4 (3)
C8—C3—C4—C5	−0.6 (3)	N2—C28—C27—C26	176.9 (2)
C2—C3—C4—C5	−179.9 (2)	C28—C27—C26—C25	0.4 (4)
C6—C5—C4—C3	0.7 (3)	C24—C25—C26—C27	0.8 (4)
I1—C5—C4—C3	−178.87 (16)	I2—C25—C26—C27	−176.51 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···O2i	0.97	2.57	3.399 (3)	144
C27—H27···O2i	0.93 (3)	2.48 (3)	3.407 (3)	174 (3)
C9—H9A···O4	0.97	2.56	3.366 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29A⋯O2i	0.97	2.57	3.399 (3)	144
C27—H27⋯O2i	0.93 (3)	2.48 (3)	3.407 (3)	174 (3)
C9—H9A⋯O4	0.97	2.56	3.366 (3)	140

Symmetry code: (i) .