4-(4-Iodo-anilino)-2-methyl-ene-4-oxo-butanoic acid.

In the title compound, C11H10INO3, an addition product of itaconic acid anhydride and 4-iodo-aniline, the least-squares planes defined by the atoms of the aromatic moiety and the non-H atoms of the carb-oxy-lic acid group enclose an angle of 74.82 (11)°. In the crystal, classical O-H⋯O hydrogen bonds formed by carb-oxy-lic groups, as well as N-H⋯O hydrogen bonds formed by amide groups, are present along with C-H⋯O contacts. Together, these connect the mol-ecules into dimeric chains along the b-axis direction.

Related literature

For applications of itaconic acid anhydride, see: Oishi (1980 ▶); Urzua et al. (1998 ▶); Shetgiri & Nayak (2005 ▶); Katla et al. (2011 ▶); Hanoon (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10INO3

M = 331.10

Monoclinic,

a = 23.1111 (6) Å

b = 4.7863 (1) Å

c = 10.4262 (2) Å

β = 97.071 (1)°

V = 1144.54 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 200 K

0.29 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.503, T max = 0.776

12435 measured reflections

2839 independent reflections

2612 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.047

S = 1.06

2839 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681205012X/gk2533sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205012X/gk2533Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205012X/gk2533Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205012X/gk2533Isup4.cml

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

C11H10INO3	F(000) = 640
Mr = 331.10	Dx = 1.921 Mg m−3
Monoclinic, P21/c	Melting point = 447–445 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.1111 (6) Å	Cell parameters from 9343 reflections
b = 4.7863 (1) Å	θ = 2.7–28.3°
c = 10.4262 (2) Å	µ = 2.79 mm−1
β = 97.071 (1)°	T = 200 K
V = 1144.54 (4) Å3	Rectangular, colourless
Z = 4	0.29 × 0.16 × 0.10 mm

Bruker APEXII CCD diffractometer	2839 independent reflections
Radiation source: fine-focus sealed tube	2612 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −30→30
Tmin = 0.503, Tmax = 0.776	k = −6→6
12435 measured reflections	l = −8→13

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0202P)2 + 0.979P] where P = (Fo2 + 2Fc2)/3
2839 reflections	(Δ/σ)max = 0.002
150 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

	x	y	z	Uiso*/Ueq
I1	0.056006 (5)	−0.19408 (3)	0.680940 (13)	0.03784 (5)
O1	0.48205 (6)	−0.1867 (3)	0.34828 (13)	0.0334 (3)
H1	0.5045	−0.1852	0.4180	0.050*
O2	0.43726 (6)	0.1500 (3)	0.44728 (13)	0.0335 (3)
O3	0.30129 (6)	−0.2166 (2)	0.35760 (14)	0.0301 (3)
N1	0.26626 (6)	0.2123 (3)	0.39810 (15)	0.0238 (3)
H71	0.2679 (10)	0.382 (5)	0.380 (2)	0.031 (6)*
C1	0.43994 (7)	−0.0058 (4)	0.35485 (16)	0.0232 (3)
C2	0.39444 (7)	0.0026 (3)	0.24115 (16)	0.0225 (3)
C3	0.34191 (7)	0.1767 (3)	0.25648 (16)	0.0232 (3)
H3A	0.3198	0.2104	0.1703	0.028*
H3B	0.3547	0.3601	0.2937	0.028*
C4	0.30202 (7)	0.0375 (3)	0.34331 (15)	0.0202 (3)
C5	0.40223 (8)	−0.1299 (4)	0.13366 (18)	0.0330 (4)
H5A	0.4371	−0.2318	0.1286	0.040*
H5B	0.3729	−0.1235	0.0614	0.040*
C11	0.21964 (7)	0.1204 (3)	0.46527 (16)	0.0218 (3)
C12	0.22773 (7)	−0.0842 (4)	0.55994 (17)	0.0263 (3)
H12	0.2652	−0.1644	0.5823	0.032*
C13	0.18104 (8)	−0.1721 (4)	0.62227 (18)	0.0284 (4)
H13	0.1864	−0.3137	0.6865	0.034*
C14	0.12659 (7)	−0.0515 (4)	0.58994 (16)	0.0265 (3)
C15	0.11850 (8)	0.1576 (4)	0.49805 (19)	0.0308 (4)
H15	0.0813	0.2421	0.4777	0.037*
C16	0.16521 (8)	0.2432 (4)	0.43571 (18)	0.0290 (4)
H16	0.1599	0.3867	0.3724	0.035*

	U11	U22	U33	U12	U13	U23
I1	0.02465 (7)	0.04793 (9)	0.04370 (9)	−0.00628 (5)	0.01530 (5)	−0.00051 (6)
O1	0.0276 (6)	0.0373 (7)	0.0342 (7)	0.0105 (5)	−0.0003 (5)	−0.0044 (6)
O2	0.0336 (7)	0.0386 (8)	0.0276 (6)	0.0087 (6)	0.0003 (5)	−0.0064 (5)
O3	0.0333 (7)	0.0172 (5)	0.0428 (7)	0.0000 (5)	0.0167 (6)	0.0006 (5)
N1	0.0239 (7)	0.0160 (6)	0.0331 (7)	0.0002 (5)	0.0096 (6)	0.0033 (6)
C1	0.0217 (7)	0.0230 (7)	0.0258 (7)	0.0002 (6)	0.0066 (6)	0.0026 (6)
C2	0.0204 (7)	0.0216 (7)	0.0262 (7)	−0.0017 (6)	0.0060 (6)	0.0036 (6)
C3	0.0205 (7)	0.0223 (8)	0.0274 (8)	0.0007 (6)	0.0050 (6)	0.0052 (6)
C4	0.0179 (7)	0.0194 (7)	0.0230 (7)	−0.0010 (5)	0.0011 (5)	0.0009 (6)
C5	0.0271 (9)	0.0400 (10)	0.0320 (9)	0.0016 (7)	0.0040 (7)	−0.0066 (8)
C11	0.0201 (7)	0.0201 (7)	0.0261 (7)	−0.0020 (6)	0.0064 (6)	−0.0024 (6)
C12	0.0194 (7)	0.0279 (8)	0.0318 (8)	0.0017 (6)	0.0046 (6)	0.0035 (7)
C13	0.0251 (8)	0.0316 (9)	0.0294 (8)	−0.0007 (7)	0.0072 (7)	0.0045 (7)
C14	0.0194 (7)	0.0323 (9)	0.0291 (8)	−0.0046 (6)	0.0083 (6)	−0.0042 (7)
C15	0.0182 (7)	0.0390 (10)	0.0356 (9)	0.0038 (7)	0.0055 (7)	0.0012 (8)
C16	0.0246 (8)	0.0306 (9)	0.0324 (9)	0.0044 (7)	0.0060 (7)	0.0070 (7)

I1—C14	2.0994 (16)	C3—H3B	0.9900
O1—C1	1.311 (2)	C5—H5A	0.9500
O1—H1	0.8400	C5—H5B	0.9500
O2—C1	1.226 (2)	C11—C12	1.387 (2)
O3—C4	1.2258 (19)	C11—C16	1.388 (2)
N1—C4	1.351 (2)	C12—C13	1.392 (2)
N1—C11	1.425 (2)	C12—H12	0.9500
N1—H71	0.83 (2)	C13—C14	1.388 (2)
C1—C2	1.485 (2)	C13—H13	0.9500
C2—C5	1.319 (2)	C14—C15	1.382 (3)
C2—C3	1.497 (2)	C15—C16	1.389 (3)
C3—C4	1.523 (2)	C15—H15	0.9500
C3—H3A	0.9900	C16—H16	0.9500
C1—O1—H1	109.5	C2—C5—H5B	120.0
C4—N1—C11	123.75 (14)	H5A—C5—H5B	120.0
C4—N1—H71	117.5 (16)	C12—C11—C16	119.74 (15)
C11—N1—H71	117.8 (16)	C12—C11—N1	121.60 (15)
O2—C1—O1	123.55 (16)	C16—C11—N1	118.65 (15)
O2—C1—C2	120.76 (15)	C11—C12—C13	120.12 (16)
O1—C1—C2	115.69 (15)	C11—C12—H12	119.9
C5—C2—C1	120.52 (16)	C13—C12—H12	119.9
C5—C2—C3	123.74 (16)	C14—C13—C12	119.52 (16)
C1—C2—C3	115.70 (14)	C14—C13—H13	120.2
C2—C3—C4	112.22 (13)	C12—C13—H13	120.2
C2—C3—H3A	109.2	C15—C14—C13	120.72 (16)
C4—C3—H3A	109.2	C15—C14—I1	120.15 (13)
C2—C3—H3B	109.2	C13—C14—I1	119.13 (13)
C4—C3—H3B	109.2	C14—C15—C16	119.43 (16)
H3A—C3—H3B	107.9	C14—C15—H15	120.3
O3—C4—N1	123.00 (15)	C16—C15—H15	120.3
O3—C4—C3	121.66 (15)	C11—C16—C15	120.43 (17)
N1—C4—C3	115.28 (14)	C11—C16—H16	119.8
C2—C5—H5A	120.0	C15—C16—H16	119.8
O2—C1—C2—C5	168.65 (18)	C4—N1—C11—C16	−131.82 (18)
O1—C1—C2—C5	−11.0 (2)	C16—C11—C12—C13	2.0 (3)
O2—C1—C2—C3	−9.2 (2)	N1—C11—C12—C13	−179.01 (16)
O1—C1—C2—C3	171.13 (14)	C11—C12—C13—C14	−0.7 (3)
C5—C2—C3—C4	108.2 (2)	C12—C13—C14—C15	−1.0 (3)
C1—C2—C3—C4	−74.03 (18)	C12—C13—C14—I1	178.29 (14)
C11—N1—C4—O3	−7.6 (3)	C13—C14—C15—C16	1.4 (3)
C11—N1—C4—C3	169.68 (15)	I1—C14—C15—C16	−177.91 (14)
C2—C3—C4—O3	−25.0 (2)	C12—C11—C16—C15	−1.6 (3)
C2—C3—C4—N1	157.71 (14)	N1—C11—C16—C15	179.35 (17)
C4—N1—C11—C12	49.1 (2)	C14—C15—C16—C11	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.83	2.6597 (19)	170
N1—H71···O3ii	0.83 (2)	2.10 (2)	2.8963 (18)	161 (2)
C3—H3B···O3ii	0.99	2.51	3.266 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.83	2.6597 (19)	170
N1—H71⋯O3ii	0.83 (2)	2.10 (2)	2.8963 (18)	161 (2)
C3—H3B⋯O3ii	0.99	2.51	3.266 (2)	134

Symmetry codes: (i) ; (ii) .