8-Iodo-5,7-dimeth-oxy-4-methyl-2H-chromen-2-one.

In the title compound, C(12)H(11)IO(4), the C and O atoms of both meth-oxy groups lie very close to the mean plane of the six C atoms of the benzene ring. The O and C atoms of the group lying closest to the I atom are 0.012 (3) and 0.022 (4) Å, respectively, out of the mean plane. For the other meth-oxy group, the corresponding distances are 0.020 (3) and 0.078 (4) Å. In the crystal, there are only very weak inter-molecular C-H⋯O hydrogen bonds and O⋯I contacts [3.080 (2) Å]. The mol-ecules are approximately parallel to (100), forming a layered structure.

Related literature

For medicinal applications of coumarin derivatives, see: Lin et al. (2006 ▶); Massimo et al. (2003 ▶); Tyagi et al. (2003 ▶); Nawrot-Modranka et al. (2006 ▶); Sardari et al. (1999 ▶); Huang et al. (2005 ▶); Elinos-Baez et al. (2005 ▶). For the synthesis of the title compound, see: Ali & Ilyas (1986 ▶). For a similar structure, see: Pereira Silva et al. (2010 ▶).

Experimental

Crystal data

C12H11IO4

M = 346.11

Triclinic,

a = 7.1103 (7) Å

b = 9.5825 (10) Å

c = 9.9866 (9) Å

α = 109.645 (5)°

β = 94.734 (5)°

γ = 104.060 (5)°

V = 611.50 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.62 mm−1

T = 293 K

0.30 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.511, T max = 0.712

17329 measured reflections

2970 independent reflections

2701 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.090

S = 1.28

2970 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007549/fj2395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007549/fj2395Isup2.hkl

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

C12H11IO4	Z = 2
Mr = 346.11	F(000) = 336
Triclinic, P1	Dx = 1.880 Mg m−3
Hall symbol: -P 1	Melting point: 523 K
a = 7.1103 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5825 (10) Å	Cell parameters from 5373 reflections
c = 9.9866 (9) Å	θ = 2.6–28.2°
α = 109.645 (5)°	µ = 2.62 mm−1
β = 94.734 (5)°	T = 293 K
γ = 104.060 (5)°	Irregular block, light pink
V = 611.50 (10) Å3	0.30 × 0.18 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	2970 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.511, Tmax = 0.712	k = −12→12
17329 measured reflections	l = −13→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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.28	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.1088P] where P = (Fo2 + 2Fc2)/3
2970 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

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	0.85918 (3)	0.28855 (2)	0.398380 (19)	0.04982 (11)
O1	0.7959 (3)	0.3031 (2)	0.0951 (2)	0.0420 (4)
O2	0.7759 (5)	0.4881 (3)	0.0176 (3)	0.0674 (7)
O3	0.6758 (4)	−0.2218 (2)	−0.2155 (2)	0.0476 (5)
O4	0.7788 (4)	−0.0678 (3)	0.3021 (2)	0.0473 (5)
C2	0.7757 (5)	0.3557 (4)	−0.0158 (4)	0.0463 (7)
C3	0.7564 (5)	0.2457 (4)	−0.1588 (3)	0.0448 (6)
H3	0.7581	0.2808	−0.2350	0.054*
C4	0.7360 (4)	0.0940 (3)	−0.1890 (3)	0.0378 (5)
C5	0.7146 (4)	−0.1155 (3)	−0.0803 (3)	0.0345 (5)
C6	0.7277 (4)	−0.1539 (3)	0.0418 (3)	0.0357 (5)
H6	0.7109	−0.2565	0.0317	0.043*
C7	0.7659 (4)	−0.0396 (3)	0.1791 (3)	0.0359 (5)
C8	0.7918 (4)	0.1150 (3)	0.1944 (3)	0.0356 (5)
C9	0.7759 (4)	0.1501 (3)	0.0716 (3)	0.0335 (5)
C10	0.7408 (4)	0.0401 (3)	−0.0695 (3)	0.0328 (5)
C11	0.7118 (5)	−0.0087 (4)	−0.3441 (3)	0.0468 (7)
H11A	0.7269	0.0532	−0.4030	0.070*
H11B	0.5830	−0.0819	−0.3742	0.070*
H11C	0.8100	−0.0630	−0.3545	0.070*
C12	0.6410 (6)	−0.3812 (4)	−0.2349 (4)	0.0552 (8)
H12A	0.7577	−0.3960	−0.1932	0.083*
H12B	0.6080	−0.4433	−0.3362	0.083*
H12C	0.5340	−0.4114	−0.1882	0.083*
C13	0.7526 (6)	−0.2253 (4)	0.2918 (4)	0.0543 (8)
H13A	0.6194	−0.2857	0.2470	0.081*
H13B	0.7790	−0.2272	0.3869	0.081*
H13C	0.8418	−0.2677	0.2348	0.081*

	U11	U22	U33	U12	U13	U23
I1	0.06807 (17)	0.03768 (14)	0.03117 (13)	0.01100 (10)	0.00271 (9)	0.00155 (9)
O1	0.0595 (12)	0.0256 (9)	0.0397 (11)	0.0125 (8)	0.0081 (9)	0.0105 (8)
O2	0.110 (2)	0.0386 (13)	0.0677 (17)	0.0334 (14)	0.0261 (16)	0.0265 (13)
O3	0.0788 (15)	0.0293 (10)	0.0298 (10)	0.0149 (10)	0.0061 (9)	0.0062 (8)
O4	0.0766 (14)	0.0390 (11)	0.0294 (10)	0.0203 (10)	0.0069 (9)	0.0144 (9)
C2	0.0567 (16)	0.0366 (15)	0.0523 (18)	0.0160 (12)	0.0147 (14)	0.0217 (14)
C3	0.0577 (16)	0.0417 (16)	0.0433 (16)	0.0159 (13)	0.0127 (13)	0.0239 (13)
C4	0.0415 (13)	0.0402 (14)	0.0350 (14)	0.0121 (11)	0.0082 (10)	0.0175 (12)
C5	0.0409 (12)	0.0300 (12)	0.0297 (13)	0.0109 (10)	0.0054 (10)	0.0073 (10)
C6	0.0454 (13)	0.0277 (12)	0.0340 (13)	0.0114 (10)	0.0070 (10)	0.0112 (10)
C7	0.0422 (13)	0.0351 (13)	0.0314 (13)	0.0126 (10)	0.0052 (10)	0.0127 (11)
C8	0.0429 (13)	0.0300 (12)	0.0296 (13)	0.0100 (10)	0.0043 (10)	0.0066 (10)
C9	0.0366 (12)	0.0266 (12)	0.0346 (13)	0.0081 (9)	0.0057 (10)	0.0086 (10)
C10	0.0385 (12)	0.0294 (12)	0.0295 (12)	0.0097 (10)	0.0059 (9)	0.0099 (10)
C11	0.0625 (17)	0.0474 (17)	0.0293 (14)	0.0130 (14)	0.0084 (12)	0.0149 (13)
C12	0.089 (2)	0.0292 (14)	0.0413 (17)	0.0170 (15)	0.0137 (16)	0.0049 (13)
C13	0.087 (2)	0.0440 (17)	0.0436 (17)	0.0286 (17)	0.0147 (16)	0.0233 (15)

I1—C8	2.078 (3)	C6—C7	1.392 (4)
O1—C2	1.374 (4)	C6—H6	0.9300
O1—C9	1.374 (3)	C7—C8	1.401 (4)
O2—C2	1.198 (4)	C8—C9	1.380 (4)
O3—C5	1.346 (3)	C9—C10	1.405 (4)
O3—C12	1.429 (4)	C11—H11A	0.9600
O4—C7	1.345 (3)	C11—H11B	0.9600
O4—C13	1.441 (4)	C11—H11C	0.9600
C2—C3	1.433 (5)	C12—H12A	0.9600
C3—C4	1.350 (4)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C10	1.452 (4)	C13—H13A	0.9600
C4—C11	1.498 (4)	C13—H13B	0.9600
C5—C6	1.389 (4)	C13—H13C	0.9600
C5—C10	1.423 (4)
C2—O1—C9	122.5 (2)	O1—C9—C8	115.4 (2)
C5—O3—C12	118.9 (2)	O1—C9—C10	120.7 (2)
C7—O4—C13	118.3 (2)	C8—C9—C10	123.9 (2)
O2—C2—O1	116.5 (3)	C9—C10—C5	115.6 (2)
O2—C2—C3	127.3 (3)	C9—C10—C4	118.2 (2)
O1—C2—C3	116.3 (2)	C5—C10—C4	126.3 (2)
C4—C3—C2	123.6 (3)	C4—C11—H11A	109.5
C4—C3—H3	118.2	C4—C11—H11B	109.5
C2—C3—H3	118.2	H11A—C11—H11B	109.5
C3—C4—C10	118.2 (3)	C4—C11—H11C	109.5
C3—C4—C11	117.9 (3)	H11A—C11—H11C	109.5
C10—C4—C11	123.9 (3)	H11B—C11—H11C	109.5
O3—C5—C6	122.7 (2)	O3—C12—H12A	109.5
O3—C5—C10	115.8 (2)	O3—C12—H12B	109.5
C6—C5—C10	121.5 (2)	H12A—C12—H12B	109.5
C5—C6—C7	120.3 (2)	O3—C12—H12C	109.5
C5—C6—H6	119.8	H12A—C12—H12C	109.5
C7—C6—H6	119.8	H12B—C12—H12C	109.5
O4—C7—C6	123.8 (2)	O4—C13—H13A	109.5
O4—C7—C8	116.3 (2)	O4—C13—H13B	109.5
C6—C7—C8	119.9 (2)	H13A—C13—H13B	109.5
C9—C8—C7	118.7 (2)	O4—C13—H13C	109.5
C9—C8—I1	120.70 (19)	H13A—C13—H13C	109.5
C7—C8—I1	120.6 (2)	H13B—C13—H13C	109.5
C9—O1—C2—O2	172.5 (3)	C2—O1—C9—C8	−177.2 (3)
C9—O1—C2—C3	−7.4 (4)	C2—O1—C9—C10	2.5 (4)
O2—C2—C3—C4	−172.5 (4)	C7—C8—C9—O1	177.7 (2)
O1—C2—C3—C4	7.4 (5)	I1—C8—C9—O1	−3.7 (3)
C2—C3—C4—C10	−2.2 (4)	C7—C8—C9—C10	−1.9 (4)
C2—C3—C4—C11	178.4 (3)	I1—C8—C9—C10	176.7 (2)
C12—O3—C5—C6	1.8 (4)	O1—C9—C10—C5	−177.5 (2)
C12—O3—C5—C10	−177.9 (3)	C8—C9—C10—C5	2.1 (4)
O3—C5—C6—C7	−179.2 (3)	O1—C9—C10—C4	3.0 (4)
C10—C5—C6—C7	0.4 (4)	C8—C9—C10—C4	−177.3 (2)
C13—O4—C7—C6	0.3 (4)	O3—C5—C10—C9	178.3 (2)
C13—O4—C7—C8	179.8 (3)	C6—C5—C10—C9	−1.3 (4)
C5—C6—C7—O4	179.3 (3)	O3—C5—C10—C4	−2.2 (4)
C5—C6—C7—C8	−0.2 (4)	C6—C5—C10—C4	178.1 (3)
O4—C7—C8—C9	−178.6 (2)	C3—C4—C10—C9	−3.1 (4)
C6—C7—C8—C9	0.9 (4)	C11—C4—C10—C9	176.3 (3)
O4—C7—C8—I1	2.8 (3)	C3—C4—C10—C5	177.5 (3)
C6—C7—C8—I1	−177.7 (2)	C11—C4—C10—C5	−3.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.56	3.460 (4)	163
C13—H13C···O2i	0.96	2.51	3.211 (5)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.56	3.460 (4)	163
C13—H13C⋯O2i	0.96	2.51	3.211 (5)	130

Symmetry code: (i) .