1,8-Bis(benz­yloxy)-3,6-diiodo­naphthalene

Liu, Y.; Wang, L.; Wang, J.; Liu, L.; Teng, M.

doi:10.1107/S1600536810019355

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1577

doi:10.1107/S1600536810019355

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1,8-Bis(benzyloxy)-3,6-diiodonaphthalene

Ying Liu,^a Leyong Wang,^a ^* Jingjing Wang,^a Li Liu ^a and Mingyu Teng ^a

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Hankou Road 22, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: lywang@nju.edu.cn

(Received 6 May 2010; accepted 24 May 2010; online 5 June 2010)

In the crystal structure of the title compound, C₂₄H₁₈I₂O₂, 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 interactions.

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_r = 592.18
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.101
S = 1.03
4111 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.86 e Å⁻³

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) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound (I), a known compound (Paruch et al., 2000), was obtained as an intermediate during deuterium substitution reactions for generating biomarkers for the melanin metabolic process (Minto & Townsend, 1997; Thompson et al., 2000; Zhang et al., 2008). In order to reduce steric congestion, the benzene rings have different orientations with respect to the central naphthyl ring. Thus, one benzene ring (C12A–C17A) is almost co-planar with the naphthyl ring [dihedral angle = 6.6 (4)°] whereas the other (C19A–C24A) is almost orthogonal [dihedral angle = 73.1 (2)°].

Molecules are linked via weak intermolecular C–H···O [C24A–H24A···O1BAⁱ = 2.49 Å, C24A···O1BAⁱ = 3.348 (8) Å with angle at H24A = 15° for i: x, 1+y, z] and C–H···π [C18A–H18A···Cg(C19A–C24A)ⁱⁱ = 2.77 Å, C18A···Cg(C19A–C24A)ⁱⁱ = 3.513 (5) Å with angle at H = 134° for ii: 1/2-x, 3/2-y, -z] interactions.

Related literature top

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 top

The precursor, 3,6-diiodonaphthalene-1,8-diol (0.4 g, 0.97 mmol), was added to a mixture of (bromomethyl)benzene (0.5 g, 2.92 mmol), potassium carbonate (0.53 g, 3.84 mmol), and acetone (40 mL) in a 50 mL flask. The mixture was heated to reflux for 4.5 hours and the solvent removed. The crude product was purified by column chromatography to give the pure title compound (I). The single crystals were obtained by slowly evaporating the solution of (I) from a petroleum and ethyl acetate mixture solvent.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

1,8-Bis(benzyloxy)-3,6-diiodonaphthalene top

Crystal data top

C₂₄H₁₈I₂O₂	F(000) = 2272
M_r = 592.18	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.04P)² + 1.22P] where P = (F_o² + 2F_c²)/3
4111 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

C₂₄H₁₈I₂O₂	V = 4186.1 (10) Å³
M_r = 592.18	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 31.222 (4) Å	µ = 3.02 mm⁻¹
b = 5.5684 (8) Å	T = 291 K
c = 27.445 (4) Å	0.28 × 0.24 × 0.22 mm
β = 118.680 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	4111 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2679 reflections with I > 2σ(I)
T_min = 0.485, T_max = 0.556	R_int = 0.038
10700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.81 e Å⁻³
4111 reflections	Δρ_min = −0.86 e Å⁻³
253 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈I₂O₂
M_r	592.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	31.222 (4), 5.5684 (8), 27.445 (4)
β (°)	118.680 (2)
V (Å³)	4186.1 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.02
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.485, 0.556
No. of measured, independent and observed [I > 2σ(I)] reflections	10700, 4111, 2679
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.101, 1.03
No. of reflections	4111
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.86

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1/2, −y+3/2, −z.

Acknowledgements

The authors gratefully acknowledge financial support by the Natural Science Foundation of Jiangsu (BK 2008259).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 66| Part 7| July 2010| Page o1577

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