6,8-Diiodo-5,7-dimeth-oxy-4-methyl-coumarin.

In the title compound, C(12)H(10)I(2)O(4), the meth-oxy groups are twisted considerably with respect to the plane of the aromatic ring [CH(3)-O-C-C torsion angles = -85.9 (3) and -92.8 (3)°]. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and O⋯I contacts [3.194 (2) Å].

Related literature

For the 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 ▶).

Experimental

Crystal data

C12H10I2O4

M = 472.00

Monoclinic,

a = 10.8681 (2) Å

b = 9.1179 (2) Å

c = 17.2315 (3) Å

β = 125.395 (1)°

V = 1391.95 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.52 mm−1

T = 293 K

0.30 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.396, T max = 0.485

27048 measured reflections

3928 independent reflections

3453 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.055

S = 1.06

3928 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.96 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011360/bt5225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011360/bt5225Isup2.hkl

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

C12H10I2O4	F(000) = 880
Mr = 472.00	Dx = 2.252 Mg m−3
Monoclinic, P21/c	Melting point: 490 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8681 (2) Å	Cell parameters from 7934 reflections
b = 9.1179 (2) Å	θ = 2.4–29.5°
c = 17.2315 (3) Å	µ = 4.52 mm−1
β = 125.395 (1)°	T = 293 K
V = 1391.95 (5) Å3	Irregular block, pale yellow
Z = 4	0.30 × 0.24 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	3928 independent reflections
Radiation source: fine-focus sealed tube	3453 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 29.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→15
Tmin = 0.396, Tmax = 0.485	k = −12→12
27048 measured reflections	l = −24→23

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: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0226P)2 + 1.1738P] where P = (Fo2 + 2Fc2)/3
3928 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.96 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.51053 (2)	0.82363 (2)	0.156895 (15)	0.05749 (7)
I2	0.11277 (2)	0.593603 (19)	0.266073 (13)	0.04546 (6)
O1	0.06827 (19)	0.35475 (17)	0.12276 (12)	0.0353 (3)
O2	−0.0507 (2)	0.1432 (2)	0.07590 (17)	0.0548 (5)
O3	0.39384 (18)	0.53122 (19)	0.03873 (12)	0.0383 (4)
O4	0.3379 (2)	0.79647 (18)	0.25451 (12)	0.0434 (4)
C8	0.1966 (3)	0.5766 (2)	0.18397 (16)	0.0317 (4)
C7	0.2959 (3)	0.6823 (2)	0.19268 (16)	0.0337 (5)
C6	0.3586 (3)	0.6668 (2)	0.14197 (17)	0.0352 (5)
C5	0.3273 (2)	0.5453 (3)	0.08510 (15)	0.0318 (4)
C10	0.2315 (2)	0.4324 (2)	0.07795 (15)	0.0297 (4)
C9	0.1647 (2)	0.4549 (2)	0.12598 (15)	0.0294 (4)
C4	0.2056 (3)	0.2920 (2)	0.03026 (16)	0.0352 (5)
C3	0.1095 (3)	0.1972 (3)	0.02911 (18)	0.0395 (5)
H3	0.0905	0.1087	−0.0028	0.047*
C2	0.0351 (3)	0.2248 (3)	0.07400 (18)	0.0379 (5)
C13	0.2462 (4)	0.9256 (3)	0.2126 (2)	0.0621 (8)
H13A	0.2393	0.9513	0.1562	0.093*
H13B	0.2911	1.0051	0.2573	0.093*
H13C	0.1470	0.9066	0.1964	0.093*
C12	0.3139 (3)	0.6047 (3)	−0.05204 (19)	0.0497 (6)
H12A	0.2153	0.5623	−0.0936	0.075*
H12B	0.3687	0.5937	−0.0797	0.075*
H12C	0.3044	0.7070	−0.0433	0.075*
C11	0.2873 (4)	0.2436 (3)	−0.0117 (2)	0.0582 (8)
H11A	0.2607	0.1440	−0.0331	0.087*
H11B	0.3942	0.2502	0.0357	0.087*
H11C	0.2592	0.3057	−0.0646	0.087*

	U11	U22	U33	U12	U13	U23
I1	0.05881 (12)	0.05243 (11)	0.06135 (13)	−0.02587 (9)	0.03486 (10)	−0.01030 (8)
I2	0.05746 (11)	0.04523 (10)	0.04782 (10)	−0.00537 (7)	0.03859 (9)	−0.01056 (7)
O1	0.0400 (9)	0.0303 (7)	0.0438 (9)	−0.0055 (6)	0.0290 (8)	−0.0069 (7)
O2	0.0650 (13)	0.0391 (9)	0.0823 (15)	−0.0165 (9)	0.0552 (12)	−0.0145 (10)
O3	0.0370 (8)	0.0458 (9)	0.0384 (9)	0.0023 (7)	0.0255 (8)	0.0035 (7)
O4	0.0572 (11)	0.0325 (8)	0.0355 (9)	−0.0062 (8)	0.0239 (8)	−0.0092 (7)
C8	0.0355 (11)	0.0304 (10)	0.0307 (10)	0.0031 (8)	0.0200 (9)	−0.0015 (8)
C7	0.0380 (12)	0.0277 (10)	0.0286 (10)	−0.0006 (8)	0.0154 (9)	−0.0023 (8)
C6	0.0355 (11)	0.0325 (11)	0.0330 (11)	−0.0057 (9)	0.0172 (10)	0.0007 (9)
C5	0.0299 (10)	0.0357 (11)	0.0291 (10)	0.0019 (8)	0.0167 (9)	0.0032 (8)
C10	0.0307 (10)	0.0294 (10)	0.0271 (10)	0.0008 (8)	0.0157 (9)	−0.0008 (8)
C9	0.0293 (10)	0.0280 (9)	0.0296 (10)	0.0003 (8)	0.0162 (9)	−0.0005 (8)
C4	0.0400 (12)	0.0334 (11)	0.0338 (11)	0.0017 (9)	0.0224 (10)	−0.0036 (9)
C3	0.0477 (14)	0.0299 (11)	0.0453 (13)	−0.0041 (10)	0.0294 (12)	−0.0077 (9)
C2	0.0409 (12)	0.0290 (10)	0.0453 (13)	−0.0031 (9)	0.0257 (11)	−0.0049 (9)
C13	0.093 (2)	0.0340 (13)	0.0625 (19)	0.0072 (15)	0.0471 (19)	−0.0025 (12)
C12	0.0480 (15)	0.0696 (18)	0.0379 (13)	0.0039 (13)	0.0285 (12)	0.0077 (12)
C11	0.078 (2)	0.0493 (16)	0.077 (2)	−0.0089 (15)	0.0618 (19)	−0.0206 (15)

I1—C6	2.084 (2)	C10—C4	1.458 (3)
I2—C8	2.085 (2)	C4—C3	1.347 (3)
O1—C9	1.367 (3)	C4—C11	1.500 (3)
O1—C2	1.375 (3)	C3—C2	1.428 (3)
O2—C2	1.208 (3)	C3—H3	0.9300
O3—C5	1.359 (3)	C13—H13A	0.9600
O3—C12	1.441 (3)	C13—H13B	0.9600
O4—C7	1.365 (3)	C13—H13C	0.9600
O4—C13	1.438 (3)	C12—H12A	0.9600
C8—C7	1.389 (3)	C12—H12B	0.9600
C8—C9	1.396 (3)	C12—H12C	0.9600
C7—C6	1.392 (3)	C11—H11A	0.9600
C6—C5	1.385 (3)	C11—H11B	0.9600
C5—C10	1.418 (3)	C11—H11C	0.9600
C10—C9	1.397 (3)
C9—O1—C2	121.60 (18)	C4—C3—C2	123.8 (2)
C5—O3—C12	113.74 (18)	C4—C3—H3	118.1
C7—O4—C13	114.3 (2)	C2—C3—H3	118.1
C7—C8—C9	118.9 (2)	O2—C2—O1	116.6 (2)
C7—C8—I2	119.53 (16)	O2—C2—C3	126.5 (2)
C9—C8—I2	121.34 (16)	O1—C2—C3	116.9 (2)
O4—C7—C8	120.0 (2)	O4—C13—H13A	109.5
O4—C7—C6	120.2 (2)	O4—C13—H13B	109.5
C8—C7—C6	119.6 (2)	H13A—C13—H13B	109.5
C5—C6—C7	121.1 (2)	O4—C13—H13C	109.5
C5—C6—I1	119.26 (17)	H13A—C13—H13C	109.5
C7—C6—I1	119.58 (16)	H13B—C13—H13C	109.5
O3—C5—C6	119.7 (2)	O3—C12—H12A	109.5
O3—C5—C10	119.6 (2)	O3—C12—H12B	109.5
C6—C5—C10	120.6 (2)	H12A—C12—H12B	109.5
C9—C10—C5	116.74 (19)	O3—C12—H12C	109.5
C9—C10—C4	117.8 (2)	H12A—C12—H12C	109.5
C5—C10—C4	125.4 (2)	H12B—C12—H12C	109.5
O1—C9—C10	121.85 (19)	C4—C11—H11A	109.5
O1—C9—C8	115.25 (19)	C4—C11—H11B	109.5
C10—C9—C8	122.8 (2)	H11A—C11—H11B	109.5
C3—C4—C10	117.8 (2)	C4—C11—H11C	109.5
C3—C4—C11	118.3 (2)	H11A—C11—H11C	109.5
C10—C4—C11	123.7 (2)	H11B—C11—H11C	109.5
C13—O4—C7—C8	−92.8 (3)	C2—O1—C9—C10	1.7 (3)
C13—O4—C7—C6	90.7 (3)	C2—O1—C9—C8	−175.3 (2)
C9—C8—C7—O4	−175.0 (2)	C5—C10—C9—O1	178.85 (19)
I2—C8—C7—O4	−0.1 (3)	C4—C10—C9—O1	−5.2 (3)
C9—C8—C7—C6	1.5 (3)	C5—C10—C9—C8	−4.3 (3)
I2—C8—C7—C6	176.40 (17)	C4—C10—C9—C8	171.7 (2)
O4—C7—C6—C5	174.5 (2)	C7—C8—C9—O1	178.8 (2)
C8—C7—C6—C5	−2.0 (3)	I2—C8—C9—O1	4.0 (3)
O4—C7—C6—I1	−2.4 (3)	C7—C8—C9—C10	1.7 (3)
C8—C7—C6—I1	−178.96 (17)	I2—C8—C9—C10	−173.05 (16)
C12—O3—C5—C6	−85.9 (3)	C9—C10—C4—C3	5.1 (3)
C12—O3—C5—C10	96.7 (3)	C5—C10—C4—C3	−179.3 (2)
C7—C6—C5—O3	−178.0 (2)	C9—C10—C4—C11	−170.8 (3)
I1—C6—C5—O3	−1.1 (3)	C5—C10—C4—C11	4.8 (4)
C7—C6—C5—C10	−0.7 (3)	C10—C4—C3—C2	−1.8 (4)
I1—C6—C5—C10	176.25 (16)	C11—C4—C3—C2	174.3 (3)
O3—C5—C10—C9	−178.92 (19)	C9—O1—C2—O2	179.6 (2)
C6—C5—C10—C9	3.7 (3)	C9—O1—C2—C3	1.7 (3)
O3—C5—C10—C4	5.4 (3)	C4—C3—C2—O2	−179.2 (3)
C6—C5—C10—C4	−171.9 (2)	C4—C3—C2—O1	−1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.53	3.460 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.53	3.460 (3)	175

Symmetry code: (i) .