1,8-Bis(benz-yloxy)-3,6-diiodo-naphthalene.

In the crystal structure of the title compound, C(24)H(18)I(2)O(2), one benzene ring is almost coplanar with the naphthyl system [dihedral angle = 6.6 (4)°], whereas the other is almost orthogonal [73.1 (2)°]. The crystal structure is consolidated by C-H⋯O and C-H⋯π inter-actions.

Related literature

For biomarkers for the Melanin metabolic process, see: Minto & Townsend (1997 ▶); Thompson et al. (2000 ▶); Zhang et al. (2008 ▶). For the synthesis of the title compound, see: Paruch et al. (2000 ▶).

Experimental

Crystal data

C24H18I2O2

M = 592.18

Monoclinic,

a = 31.222 (4) Å

b = 5.5684 (8) Å

c = 27.445 (4) Å

β = 118.680 (2)°

V = 4186.1 (10) Å3

Z = 8

Mo Kα radiation

μ = 3.02 mm−1

T = 291 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.485, T max = 0.556

10700 measured reflections

4111 independent reflections

2679 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.101

S = 1.03

4111 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.86 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019355/tk2673sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019355/tk2673Isup2.hkl

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

C24H18I2O2	F(000) = 2272
Mr = 592.18	Dx = 1.879 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3618 reflections
a = 31.222 (4) Å	θ = 2.6–27.6°
b = 5.5684 (8) Å	µ = 3.02 mm−1
c = 27.445 (4) Å	T = 291 K
β = 118.680 (2)°	Block, brown
V = 4186.1 (10) Å3	0.28 × 0.24 × 0.22 mm
Z = 8

Bruker SMART APEX CCD diffractometer	4111 independent reflections
Radiation source: sealed tube	2679 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −38→36
Tmin = 0.485, Tmax = 0.556	k = −6→5
10700 measured reflections	l = −31→33

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.04P)2 + 1.22P] where P = (Fo2 + 2Fc2)/3
4111 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.86 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
I1BA	0.532315 (16)	−0.52925 (9)	0.184014 (16)	0.05132 (16)
I2BA	0.419035 (16)	0.51148 (9)	−0.067214 (17)	0.05151 (15)
O2BA	0.35208 (14)	0.3984 (7)	0.08149 (16)	0.0368 (9)
O1BA	0.39304 (14)	0.1087 (7)	0.16410 (16)	0.0363 (9)
C7BA	0.3862 (2)	0.4364 (11)	0.0199 (2)	0.0382 (14)
H7AA	0.3664	0.5679	0.0024	0.046*
C1BA	0.42086 (19)	0.0189 (11)	0.1420 (2)	0.0324 (12)
C18A	0.31949 (19)	0.5945 (10)	0.0502 (2)	0.0328 (12)
H18A	0.3029	0.5558	0.0109	0.039*
H18B	0.3382	0.7401	0.0554	0.039*
C9BA	0.41640 (19)	0.1355 (11)	0.0930 (2)	0.0320 (12)
C8BA	0.38423 (18)	0.3302 (10)	0.0639 (2)	0.0295 (12)
C3BA	0.4817 (2)	−0.2471 (10)	0.1437 (2)	0.0344 (13)
C12A	0.36459 (19)	0.1100 (11)	0.2302 (2)	0.0319 (12)
C16A	0.3090 (2)	0.4135 (12)	0.2268 (2)	0.0433 (15)
H16A	0.2918	0.5539	0.2108	0.052*
C24A	0.28382 (19)	0.8405 (11)	0.0981 (2)	0.0327 (13)
H24A	0.3086	0.9526	0.1070	0.039*
C10A	0.4473 (2)	0.0466 (11)	0.0720 (2)	0.0387 (14)
C20A	0.2453 (2)	0.4703 (11)	0.0574 (2)	0.0398 (14)
H20A	0.2444	0.3288	0.0389	0.048*
C5BA	0.4469 (2)	0.1581 (13)	0.0250 (3)	0.0464 (16)
H5AA	0.4667	0.0990	0.0111	0.056*
C23A	0.2477 (2)	0.8811 (13)	0.1134 (3)	0.0479 (16)
H23A	0.2486	1.0209	0.1324	0.057*
C17A	0.3387 (2)	0.3144 (11)	0.2077 (2)	0.0351 (13)
H17A	0.3411	0.3891	0.1788	0.042*
C21A	0.2097 (2)	0.5140 (13)	0.0718 (2)	0.0433 (14)
H21A	0.1843	0.4052	0.0619	0.052*
C19A	0.2827 (2)	0.6336 (11)	0.0698 (2)	0.0338 (13)
C4BA	0.4804 (2)	−0.1452 (11)	0.0988 (2)	0.0357 (13)
H4AA	0.5009	−0.1993	0.0854	0.043*
C14A	0.3307 (2)	0.1026 (12)	0.2930 (3)	0.0421 (15)
H14A	0.3280	0.0315	0.3221	0.051*
C22A	0.2115 (2)	0.7196 (11)	0.1009 (2)	0.0370 (14)
H22A	0.1879	0.7468	0.1119	0.044*
C6BA	0.4180 (2)	0.3482 (12)	0.0009 (2)	0.0397 (14)
C2BA	0.4528 (2)	−0.1716 (10)	0.1661 (2)	0.0331 (12)
H2AA	0.4547	−0.2482	0.1972	0.040*
C11A	0.3975 (2)	−0.0106 (11)	0.2126 (2)	0.0341 (12)
H11A	0.4310	−0.0026	0.2422	0.041*
H11B	0.3885	−0.1783	0.2044	0.041*
C15A	0.3048 (2)	0.3079 (13)	0.2684 (3)	0.0470 (16)
H15A	0.2842	0.3741	0.2806	0.056*
C13A	0.3607 (2)	0.0025 (13)	0.2745 (3)	0.0469 (15)
H13A	0.3784	−0.1359	0.2911	0.056*

	U11	U22	U33	U12	U13	U23
I1BA	0.0530 (3)	0.0509 (3)	0.0396 (2)	0.0078 (2)	0.0138 (2)	0.0003 (2)
I2BA	0.0522 (3)	0.0498 (3)	0.0435 (2)	0.0144 (2)	0.01566 (19)	0.0142 (2)
O2BA	0.030 (2)	0.039 (2)	0.036 (2)	0.0099 (18)	0.0113 (18)	0.0087 (18)
O1BA	0.030 (2)	0.037 (2)	0.037 (2)	0.0072 (18)	0.0116 (17)	0.0099 (18)
C7BA	0.036 (3)	0.034 (4)	0.039 (3)	0.007 (2)	0.014 (3)	0.005 (3)
C1BA	0.028 (3)	0.037 (3)	0.030 (2)	−0.005 (3)	0.011 (2)	−0.001 (3)
C18A	0.030 (3)	0.028 (3)	0.035 (3)	0.005 (2)	0.011 (2)	0.007 (2)
C9BA	0.024 (3)	0.036 (3)	0.032 (3)	−0.001 (2)	0.011 (2)	0.001 (3)
C8BA	0.024 (3)	0.033 (3)	0.027 (3)	−0.003 (2)	0.009 (2)	−0.001 (2)
C3BA	0.030 (3)	0.027 (3)	0.039 (3)	0.000 (2)	0.011 (2)	−0.003 (2)
C12A	0.029 (3)	0.037 (3)	0.029 (3)	0.003 (2)	0.013 (2)	−0.006 (2)
C16A	0.039 (3)	0.045 (4)	0.036 (3)	0.013 (3)	0.011 (3)	−0.003 (3)
C24A	0.021 (3)	0.040 (3)	0.032 (3)	0.001 (2)	0.009 (2)	0.000 (2)
C10A	0.039 (3)	0.042 (4)	0.036 (3)	0.001 (3)	0.018 (3)	0.002 (3)
C20A	0.041 (3)	0.034 (4)	0.041 (3)	0.000 (3)	0.017 (3)	−0.005 (3)
C5BA	0.036 (3)	0.053 (4)	0.044 (3)	0.008 (3)	0.014 (3)	0.003 (3)
C23A	0.046 (4)	0.048 (4)	0.044 (3)	0.014 (3)	0.018 (3)	0.000 (3)
C17A	0.038 (3)	0.034 (3)	0.030 (3)	−0.002 (3)	0.013 (3)	0.000 (2)
C21A	0.033 (3)	0.046 (4)	0.043 (3)	−0.002 (3)	0.012 (3)	−0.002 (3)
C19A	0.033 (3)	0.038 (3)	0.030 (3)	0.007 (3)	0.015 (2)	0.006 (3)
C4BA	0.031 (3)	0.035 (3)	0.041 (3)	0.008 (3)	0.017 (3)	−0.003 (3)
C14A	0.035 (3)	0.047 (4)	0.043 (3)	0.006 (3)	0.018 (3)	0.017 (3)
C22A	0.031 (3)	0.039 (4)	0.036 (3)	0.009 (3)	0.012 (3)	0.007 (3)
C6BA	0.036 (3)	0.047 (4)	0.033 (3)	0.002 (3)	0.015 (3)	0.005 (3)
C2BA	0.030 (3)	0.035 (3)	0.035 (3)	0.001 (2)	0.016 (3)	0.003 (3)
C11A	0.034 (3)	0.037 (3)	0.031 (2)	0.003 (3)	0.015 (2)	0.006 (3)
C15A	0.040 (4)	0.050 (4)	0.043 (3)	0.013 (3)	0.014 (3)	0.002 (3)
C13A	0.046 (3)	0.046 (4)	0.044 (3)	0.024 (3)	0.017 (3)	0.014 (3)

I1BA—C3BA	2.124 (6)	C24A—C23A	1.397 (8)
I2BA—C6BA	2.092 (6)	C24A—H24A	0.9300
O2BA—C8BA	1.361 (6)	C10A—C4BA	1.421 (8)
O2BA—C18A	1.458 (6)	C10A—C5BA	1.425 (8)
O1BA—C1BA	1.369 (7)	C20A—C21A	1.368 (9)
O1BA—C11A	1.434 (6)	C20A—C19A	1.387 (8)
C7BA—C8BA	1.371 (8)	C20A—H20A	0.9300
C7BA—C6BA	1.414 (8)	C5BA—C6BA	1.342 (9)
C7BA—H7AA	0.9300	C5BA—H5AA	0.9300
C1BA—C2BA	1.387 (8)	C23A—C22A	1.354 (9)
C1BA—C9BA	1.439 (7)	C23A—H23A	0.9300
C18A—C19A	1.499 (7)	C17A—H17A	0.9300
C18A—H18A	0.9700	C21A—C22A	1.382 (9)
C18A—H18B	0.9700	C21A—H21A	0.9300
C9BA—C10A	1.430 (8)	C4BA—H4AA	0.9300
C9BA—C8BA	1.433 (8)	C14A—C15A	1.376 (9)
C3BA—C4BA	1.338 (8)	C14A—C13A	1.381 (9)
C3BA—C2BA	1.379 (8)	C14A—H14A	0.9300
C12A—C17A	1.361 (8)	C22A—H22A	0.9300
C12A—C13A	1.410 (8)	C2BA—H2AA	0.9300
C12A—C11A	1.489 (8)	C11A—H11A	0.9700
C16A—C15A	1.345 (9)	C11A—H11B	0.9700
C16A—C17A	1.381 (8)	C15A—H15A	0.9300
C16A—H16A	0.9300	C13A—H13A	0.9300
C24A—C19A	1.380 (8)
C8BA—O2BA—C18A	115.2 (4)	C10A—C5BA—H5AA	119.9
C1BA—O1BA—C11A	116.2 (4)	C22A—C23A—C24A	120.9 (6)
C8BA—C7BA—C6BA	120.7 (5)	C22A—C23A—H23A	119.6
C8BA—C7BA—H7AA	119.6	C24A—C23A—H23A	119.6
C6BA—C7BA—H7AA	119.6	C12A—C17A—C16A	121.5 (6)
O1BA—C1BA—C2BA	122.2 (5)	C12A—C17A—H17A	119.2
O1BA—C1BA—C9BA	116.8 (5)	C16A—C17A—H17A	119.2
C2BA—C1BA—C9BA	121.0 (5)	C20A—C21A—C22A	120.2 (6)
O2BA—C18A—C19A	109.6 (4)	C20A—C21A—H21A	119.9
O2BA—C18A—H18A	109.7	C22A—C21A—H21A	119.9
C19A—C18A—H18A	109.7	C24A—C19A—C20A	118.5 (5)
O2BA—C18A—H18B	109.7	C24A—C19A—C18A	120.4 (5)
C19A—C18A—H18B	109.7	C20A—C19A—C18A	121.0 (5)
H18A—C18A—H18B	108.2	C3BA—C4BA—C10A	119.3 (5)
C10A—C9BA—C8BA	117.7 (5)	C3BA—C4BA—H4AA	120.4
C10A—C9BA—C1BA	116.1 (5)	C10A—C4BA—H4AA	120.4
C8BA—C9BA—C1BA	126.2 (5)	C15A—C14A—C13A	119.8 (6)
O2BA—C8BA—C7BA	123.0 (5)	C15A—C14A—H14A	120.1
O2BA—C8BA—C9BA	116.9 (5)	C13A—C14A—H14A	120.1
C7BA—C8BA—C9BA	120.2 (5)	C23A—C22A—C21A	119.5 (6)
C4BA—C3BA—C2BA	122.9 (5)	C23A—C22A—H22A	120.2
C4BA—C3BA—I1BA	118.7 (4)	C21A—C22A—H22A	120.2
C2BA—C3BA—I1BA	118.4 (4)	C5BA—C6BA—C7BA	121.1 (6)
C17A—C12A—C13A	117.9 (5)	C5BA—C6BA—I2BA	119.3 (5)
C17A—C12A—C11A	125.6 (5)	C7BA—C6BA—I2BA	119.6 (4)
C13A—C12A—C11A	116.5 (5)	C3BA—C2BA—C1BA	119.7 (5)
C15A—C16A—C17A	120.3 (6)	C3BA—C2BA—H2AA	120.1
C15A—C16A—H16A	119.9	C1BA—C2BA—H2AA	120.1
C17A—C16A—H16A	119.9	O1BA—C11A—C12A	108.6 (5)
C19A—C24A—C23A	119.9 (6)	O1BA—C11A—H11A	110.0
C19A—C24A—H24A	120.1	C12A—C11A—H11A	110.0
C23A—C24A—H24A	120.1	O1BA—C11A—H11B	110.0
C4BA—C10A—C5BA	119.0 (6)	C12A—C11A—H11B	110.0
C4BA—C10A—C9BA	121.0 (5)	H11A—C11A—H11B	108.4
C5BA—C10A—C9BA	120.0 (6)	C16A—C15A—C14A	120.5 (6)
C21A—C20A—C19A	121.1 (6)	C16A—C15A—H15A	119.8
C21A—C20A—H20A	119.5	C14A—C15A—H15A	119.8
C19A—C20A—H20A	119.5	C14A—C13A—C12A	120.0 (6)
C6BA—C5BA—C10A	120.2 (6)	C14A—C13A—H13A	120.0
C6BA—C5BA—H5AA	119.9	C12A—C13A—H13A	120.0
C11A—O1BA—C1BA—C2BA	−2.1 (8)	C23A—C24A—C19A—C18A	176.4 (5)
C11A—O1BA—C1BA—C9BA	179.4 (5)	C21A—C20A—C19A—C24A	1.1 (9)
C8BA—O2BA—C18A—C19A	174.0 (5)	C21A—C20A—C19A—C18A	−175.3 (5)
O1BA—C1BA—C9BA—C10A	177.3 (5)	O2BA—C18A—C19A—C24A	111.8 (6)
C2BA—C1BA—C9BA—C10A	−1.2 (8)	O2BA—C18A—C19A—C20A	−71.8 (6)
O1BA—C1BA—C9BA—C8BA	−2.7 (8)	C2BA—C3BA—C4BA—C10A	−1.2 (9)
C2BA—C1BA—C9BA—C8BA	178.8 (6)	I1BA—C3BA—C4BA—C10A	−179.0 (4)
C18A—O2BA—C8BA—C7BA	−0.1 (8)	C5BA—C10A—C4BA—C3BA	178.5 (6)
C18A—O2BA—C8BA—C9BA	−179.1 (5)	C9BA—C10A—C4BA—C3BA	1.5 (9)
C6BA—C7BA—C8BA—O2BA	−175.7 (5)	C24A—C23A—C22A—C21A	−1.2 (9)
C6BA—C7BA—C8BA—C9BA	3.3 (9)	C20A—C21A—C22A—C23A	2.2 (9)
C10A—C9BA—C8BA—O2BA	174.3 (5)	C10A—C5BA—C6BA—C7BA	−2.3 (10)
C1BA—C9BA—C8BA—O2BA	−5.7 (8)	C10A—C5BA—C6BA—I2BA	179.0 (5)
C10A—C9BA—C8BA—C7BA	−4.7 (8)	C8BA—C7BA—C6BA—C5BA	0.3 (10)
C1BA—C9BA—C8BA—C7BA	175.3 (5)	C8BA—C7BA—C6BA—I2BA	179.0 (4)
C8BA—C9BA—C10A—C4BA	179.6 (5)	C4BA—C3BA—C2BA—C1BA	−0.4 (9)
C1BA—C9BA—C10A—C4BA	−0.3 (8)	I1BA—C3BA—C2BA—C1BA	177.4 (4)
C8BA—C9BA—C10A—C5BA	2.7 (8)	O1BA—C1BA—C2BA—C3BA	−176.8 (5)
C1BA—C9BA—C10A—C5BA	−177.3 (5)	C9BA—C1BA—C2BA—C3BA	1.7 (8)
C4BA—C10A—C5BA—C6BA	−176.2 (6)	C1BA—O1BA—C11A—C12A	−179.6 (4)
C9BA—C10A—C5BA—C6BA	0.8 (9)	C17A—C12A—C11A—O1BA	−6.4 (8)
C19A—C24A—C23A—C22A	0.2 (9)	C13A—C12A—C11A—O1BA	174.3 (5)
C13A—C12A—C17A—C16A	−0.8 (9)	C17A—C16A—C15A—C14A	1.2 (10)
C11A—C12A—C17A—C16A	180.0 (6)	C13A—C14A—C15A—C16A	−0.8 (10)
C15A—C16A—C17A—C12A	−0.3 (9)	C15A—C14A—C13A—C12A	−0.3 (10)
C19A—C20A—C21A—C22A	−2.2 (9)	C17A—C12A—C13A—C14A	1.1 (9)
C23A—C24A—C19A—C20A	−0.1 (8)	C11A—C12A—C13A—C14A	−179.6 (6)

Cg is the centroid of the C19A–C24A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C24A—H24A···O1BAi	0.93	2.49	3.348 (8)	154
C18A—H18A···Cgii	0.97	2.77	3.513 (5)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C19A–C24A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24A—H24A⋯O1BAi	0.93	2.49	3.348 (8)	154
C18A—H18A⋯Cgii	0.97	2.77	3.513 (5)	134

Symmetry codes: (i) ; (ii) .