organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Minto, R. E. & Townsend, C. A. (1997). Chem. Rev. 97, 2537-2555.]); Thompson et al. (2000[Thompson, J. E., Fahnestock, S., Farrall, L., Liao, D.-I., Valent, B. & Jordan, D. B. (2000). J. Biol. Chem. 275, 34867-34872.]); Zhang et al. (2008[Zhang, Y. L., Hui, M. G., Zhao, W., Dong, H., Xu, Q., Li, S. H., Li, J., Zhang, J., Song, Y. C. & Tan, R. X. (2008). Angew. Chem. Int. Ed. 47, 5823-5826.]). For the synthesis of the title compound, see: Paruch et al. (2000[Paruch, K., Vyklicky, L., Katz, T. J., Incarvito, C. D. & Rheingold, A. L. (2000). J. Org. Chem. 65, 8774-8782.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18I2O2

  • Mr = 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.485, Tmax = 0.556

  • 10700 measured reflections

  • 4111 independent reflections

  • 2679 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C19A–C24A ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C24A—H24A⋯O1BAi 0.93 2.49 3.348 (8) 154
C18A—H18ACgii 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[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All the H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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
C24H18I2O2F(000) = 2272
Mr = 592.18Dx = 1.879 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3618 reflections
a = 31.222 (4) Åθ = 2.6–27.6°
b = 5.5684 (8) ŵ = 3.02 mm1
c = 27.445 (4) ÅT = 291 K
β = 118.680 (2)°Block, brown
V = 4186.1 (10) Å30.28 × 0.24 × 0.22 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer
4111 independent reflections
Radiation source: sealed tube2679 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 3836
Tmin = 0.485, Tmax = 0.556k = 65
10700 measured reflectionsl = 3133
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-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 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.86 e Å3
Crystal data top
C24H18I2O2V = 4186.1 (10) Å3
Mr = 592.18Z = 8
Monoclinic, C2/cMo Kα radiation
a = 31.222 (4) ŵ = 3.02 mm1
b = 5.5684 (8) ÅT = 291 K
c = 27.445 (4) Å0.28 × 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)
Tmin = 0.485, Tmax = 0.556Rint = 0.038
10700 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.03Δρmax = 0.81 e Å3
4111 reflectionsΔρmin = 0.86 e Å3
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
xyzUiso*/Ueq
I1BA0.532315 (16)0.52925 (9)0.184014 (16)0.05132 (16)
I2BA0.419035 (16)0.51148 (9)0.067214 (17)0.05151 (15)
O2BA0.35208 (14)0.3984 (7)0.08149 (16)0.0368 (9)
O1BA0.39304 (14)0.1087 (7)0.16410 (16)0.0363 (9)
C7BA0.3862 (2)0.4364 (11)0.0199 (2)0.0382 (14)
H7AA0.36640.56790.00240.046*
C1BA0.42086 (19)0.0189 (11)0.1420 (2)0.0324 (12)
C18A0.31949 (19)0.5945 (10)0.0502 (2)0.0328 (12)
H18A0.30290.55580.01090.039*
H18B0.33820.74010.05540.039*
C9BA0.41640 (19)0.1355 (11)0.0930 (2)0.0320 (12)
C8BA0.38423 (18)0.3302 (10)0.0639 (2)0.0295 (12)
C3BA0.4817 (2)0.2471 (10)0.1437 (2)0.0344 (13)
C12A0.36459 (19)0.1100 (11)0.2302 (2)0.0319 (12)
C16A0.3090 (2)0.4135 (12)0.2268 (2)0.0433 (15)
H16A0.29180.55390.21080.052*
C24A0.28382 (19)0.8405 (11)0.0981 (2)0.0327 (13)
H24A0.30860.95260.10700.039*
C10A0.4473 (2)0.0466 (11)0.0720 (2)0.0387 (14)
C20A0.2453 (2)0.4703 (11)0.0574 (2)0.0398 (14)
H20A0.24440.32880.03890.048*
C5BA0.4469 (2)0.1581 (13)0.0250 (3)0.0464 (16)
H5AA0.46670.09900.01110.056*
C23A0.2477 (2)0.8811 (13)0.1134 (3)0.0479 (16)
H23A0.24861.02090.13240.057*
C17A0.3387 (2)0.3144 (11)0.2077 (2)0.0351 (13)
H17A0.34110.38910.17880.042*
C21A0.2097 (2)0.5140 (13)0.0718 (2)0.0433 (14)
H21A0.18430.40520.06190.052*
C19A0.2827 (2)0.6336 (11)0.0698 (2)0.0338 (13)
C4BA0.4804 (2)0.1452 (11)0.0988 (2)0.0357 (13)
H4AA0.50090.19930.08540.043*
C14A0.3307 (2)0.1026 (12)0.2930 (3)0.0421 (15)
H14A0.32800.03150.32210.051*
C22A0.2115 (2)0.7196 (11)0.1009 (2)0.0370 (14)
H22A0.18790.74680.11190.044*
C6BA0.4180 (2)0.3482 (12)0.0009 (2)0.0397 (14)
C2BA0.4528 (2)0.1716 (10)0.1661 (2)0.0331 (12)
H2AA0.45470.24820.19720.040*
C11A0.3975 (2)0.0106 (11)0.2126 (2)0.0341 (12)
H11A0.43100.00260.24220.041*
H11B0.38850.17830.20440.041*
C15A0.3048 (2)0.3079 (13)0.2684 (3)0.0470 (16)
H15A0.28420.37410.28060.056*
C13A0.3607 (2)0.0025 (13)0.2745 (3)0.0469 (15)
H13A0.37840.13590.29110.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I1BA0.0530 (3)0.0509 (3)0.0396 (2)0.0078 (2)0.0138 (2)0.0003 (2)
I2BA0.0522 (3)0.0498 (3)0.0435 (2)0.0144 (2)0.01566 (19)0.0142 (2)
O2BA0.030 (2)0.039 (2)0.036 (2)0.0099 (18)0.0113 (18)0.0087 (18)
O1BA0.030 (2)0.037 (2)0.037 (2)0.0072 (18)0.0116 (17)0.0099 (18)
C7BA0.036 (3)0.034 (4)0.039 (3)0.007 (2)0.014 (3)0.005 (3)
C1BA0.028 (3)0.037 (3)0.030 (2)0.005 (3)0.011 (2)0.001 (3)
C18A0.030 (3)0.028 (3)0.035 (3)0.005 (2)0.011 (2)0.007 (2)
C9BA0.024 (3)0.036 (3)0.032 (3)0.001 (2)0.011 (2)0.001 (3)
C8BA0.024 (3)0.033 (3)0.027 (3)0.003 (2)0.009 (2)0.001 (2)
C3BA0.030 (3)0.027 (3)0.039 (3)0.000 (2)0.011 (2)0.003 (2)
C12A0.029 (3)0.037 (3)0.029 (3)0.003 (2)0.013 (2)0.006 (2)
C16A0.039 (3)0.045 (4)0.036 (3)0.013 (3)0.011 (3)0.003 (3)
C24A0.021 (3)0.040 (3)0.032 (3)0.001 (2)0.009 (2)0.000 (2)
C10A0.039 (3)0.042 (4)0.036 (3)0.001 (3)0.018 (3)0.002 (3)
C20A0.041 (3)0.034 (4)0.041 (3)0.000 (3)0.017 (3)0.005 (3)
C5BA0.036 (3)0.053 (4)0.044 (3)0.008 (3)0.014 (3)0.003 (3)
C23A0.046 (4)0.048 (4)0.044 (3)0.014 (3)0.018 (3)0.000 (3)
C17A0.038 (3)0.034 (3)0.030 (3)0.002 (3)0.013 (3)0.000 (2)
C21A0.033 (3)0.046 (4)0.043 (3)0.002 (3)0.012 (3)0.002 (3)
C19A0.033 (3)0.038 (3)0.030 (3)0.007 (3)0.015 (2)0.006 (3)
C4BA0.031 (3)0.035 (3)0.041 (3)0.008 (3)0.017 (3)0.003 (3)
C14A0.035 (3)0.047 (4)0.043 (3)0.006 (3)0.018 (3)0.017 (3)
C22A0.031 (3)0.039 (4)0.036 (3)0.009 (3)0.012 (3)0.007 (3)
C6BA0.036 (3)0.047 (4)0.033 (3)0.002 (3)0.015 (3)0.005 (3)
C2BA0.030 (3)0.035 (3)0.035 (3)0.001 (2)0.016 (3)0.003 (3)
C11A0.034 (3)0.037 (3)0.031 (2)0.003 (3)0.015 (2)0.006 (3)
C15A0.040 (4)0.050 (4)0.043 (3)0.013 (3)0.014 (3)0.002 (3)
C13A0.046 (3)0.046 (4)0.044 (3)0.024 (3)0.017 (3)0.014 (3)
Geometric parameters (Å, º) top
I1BA—C3BA2.124 (6)C24A—C23A1.397 (8)
I2BA—C6BA2.092 (6)C24A—H24A0.9300
O2BA—C8BA1.361 (6)C10A—C4BA1.421 (8)
O2BA—C18A1.458 (6)C10A—C5BA1.425 (8)
O1BA—C1BA1.369 (7)C20A—C21A1.368 (9)
O1BA—C11A1.434 (6)C20A—C19A1.387 (8)
C7BA—C8BA1.371 (8)C20A—H20A0.9300
C7BA—C6BA1.414 (8)C5BA—C6BA1.342 (9)
C7BA—H7AA0.9300C5BA—H5AA0.9300
C1BA—C2BA1.387 (8)C23A—C22A1.354 (9)
C1BA—C9BA1.439 (7)C23A—H23A0.9300
C18A—C19A1.499 (7)C17A—H17A0.9300
C18A—H18A0.9700C21A—C22A1.382 (9)
C18A—H18B0.9700C21A—H21A0.9300
C9BA—C10A1.430 (8)C4BA—H4AA0.9300
C9BA—C8BA1.433 (8)C14A—C15A1.376 (9)
C3BA—C4BA1.338 (8)C14A—C13A1.381 (9)
C3BA—C2BA1.379 (8)C14A—H14A0.9300
C12A—C17A1.361 (8)C22A—H22A0.9300
C12A—C13A1.410 (8)C2BA—H2AA0.9300
C12A—C11A1.489 (8)C11A—H11A0.9700
C16A—C15A1.345 (9)C11A—H11B0.9700
C16A—C17A1.381 (8)C15A—H15A0.9300
C16A—H16A0.9300C13A—H13A0.9300
C24A—C19A1.380 (8)
C8BA—O2BA—C18A115.2 (4)C10A—C5BA—H5AA119.9
C1BA—O1BA—C11A116.2 (4)C22A—C23A—C24A120.9 (6)
C8BA—C7BA—C6BA120.7 (5)C22A—C23A—H23A119.6
C8BA—C7BA—H7AA119.6C24A—C23A—H23A119.6
C6BA—C7BA—H7AA119.6C12A—C17A—C16A121.5 (6)
O1BA—C1BA—C2BA122.2 (5)C12A—C17A—H17A119.2
O1BA—C1BA—C9BA116.8 (5)C16A—C17A—H17A119.2
C2BA—C1BA—C9BA121.0 (5)C20A—C21A—C22A120.2 (6)
O2BA—C18A—C19A109.6 (4)C20A—C21A—H21A119.9
O2BA—C18A—H18A109.7C22A—C21A—H21A119.9
C19A—C18A—H18A109.7C24A—C19A—C20A118.5 (5)
O2BA—C18A—H18B109.7C24A—C19A—C18A120.4 (5)
C19A—C18A—H18B109.7C20A—C19A—C18A121.0 (5)
H18A—C18A—H18B108.2C3BA—C4BA—C10A119.3 (5)
C10A—C9BA—C8BA117.7 (5)C3BA—C4BA—H4AA120.4
C10A—C9BA—C1BA116.1 (5)C10A—C4BA—H4AA120.4
C8BA—C9BA—C1BA126.2 (5)C15A—C14A—C13A119.8 (6)
O2BA—C8BA—C7BA123.0 (5)C15A—C14A—H14A120.1
O2BA—C8BA—C9BA116.9 (5)C13A—C14A—H14A120.1
C7BA—C8BA—C9BA120.2 (5)C23A—C22A—C21A119.5 (6)
C4BA—C3BA—C2BA122.9 (5)C23A—C22A—H22A120.2
C4BA—C3BA—I1BA118.7 (4)C21A—C22A—H22A120.2
C2BA—C3BA—I1BA118.4 (4)C5BA—C6BA—C7BA121.1 (6)
C17A—C12A—C13A117.9 (5)C5BA—C6BA—I2BA119.3 (5)
C17A—C12A—C11A125.6 (5)C7BA—C6BA—I2BA119.6 (4)
C13A—C12A—C11A116.5 (5)C3BA—C2BA—C1BA119.7 (5)
C15A—C16A—C17A120.3 (6)C3BA—C2BA—H2AA120.1
C15A—C16A—H16A119.9C1BA—C2BA—H2AA120.1
C17A—C16A—H16A119.9O1BA—C11A—C12A108.6 (5)
C19A—C24A—C23A119.9 (6)O1BA—C11A—H11A110.0
C19A—C24A—H24A120.1C12A—C11A—H11A110.0
C23A—C24A—H24A120.1O1BA—C11A—H11B110.0
C4BA—C10A—C5BA119.0 (6)C12A—C11A—H11B110.0
C4BA—C10A—C9BA121.0 (5)H11A—C11A—H11B108.4
C5BA—C10A—C9BA120.0 (6)C16A—C15A—C14A120.5 (6)
C21A—C20A—C19A121.1 (6)C16A—C15A—H15A119.8
C21A—C20A—H20A119.5C14A—C15A—H15A119.8
C19A—C20A—H20A119.5C14A—C13A—C12A120.0 (6)
C6BA—C5BA—C10A120.2 (6)C14A—C13A—H13A120.0
C6BA—C5BA—H5AA119.9C12A—C13A—H13A120.0
C11A—O1BA—C1BA—C2BA2.1 (8)C23A—C24A—C19A—C18A176.4 (5)
C11A—O1BA—C1BA—C9BA179.4 (5)C21A—C20A—C19A—C24A1.1 (9)
C8BA—O2BA—C18A—C19A174.0 (5)C21A—C20A—C19A—C18A175.3 (5)
O1BA—C1BA—C9BA—C10A177.3 (5)O2BA—C18A—C19A—C24A111.8 (6)
C2BA—C1BA—C9BA—C10A1.2 (8)O2BA—C18A—C19A—C20A71.8 (6)
O1BA—C1BA—C9BA—C8BA2.7 (8)C2BA—C3BA—C4BA—C10A1.2 (9)
C2BA—C1BA—C9BA—C8BA178.8 (6)I1BA—C3BA—C4BA—C10A179.0 (4)
C18A—O2BA—C8BA—C7BA0.1 (8)C5BA—C10A—C4BA—C3BA178.5 (6)
C18A—O2BA—C8BA—C9BA179.1 (5)C9BA—C10A—C4BA—C3BA1.5 (9)
C6BA—C7BA—C8BA—O2BA175.7 (5)C24A—C23A—C22A—C21A1.2 (9)
C6BA—C7BA—C8BA—C9BA3.3 (9)C20A—C21A—C22A—C23A2.2 (9)
C10A—C9BA—C8BA—O2BA174.3 (5)C10A—C5BA—C6BA—C7BA2.3 (10)
C1BA—C9BA—C8BA—O2BA5.7 (8)C10A—C5BA—C6BA—I2BA179.0 (5)
C10A—C9BA—C8BA—C7BA4.7 (8)C8BA—C7BA—C6BA—C5BA0.3 (10)
C1BA—C9BA—C8BA—C7BA175.3 (5)C8BA—C7BA—C6BA—I2BA179.0 (4)
C8BA—C9BA—C10A—C4BA179.6 (5)C4BA—C3BA—C2BA—C1BA0.4 (9)
C1BA—C9BA—C10A—C4BA0.3 (8)I1BA—C3BA—C2BA—C1BA177.4 (4)
C8BA—C9BA—C10A—C5BA2.7 (8)O1BA—C1BA—C2BA—C3BA176.8 (5)
C1BA—C9BA—C10A—C5BA177.3 (5)C9BA—C1BA—C2BA—C3BA1.7 (8)
C4BA—C10A—C5BA—C6BA176.2 (6)C1BA—O1BA—C11A—C12A179.6 (4)
C9BA—C10A—C5BA—C6BA0.8 (9)C17A—C12A—C11A—O1BA6.4 (8)
C19A—C24A—C23A—C22A0.2 (9)C13A—C12A—C11A—O1BA174.3 (5)
C13A—C12A—C17A—C16A0.8 (9)C17A—C16A—C15A—C14A1.2 (10)
C11A—C12A—C17A—C16A180.0 (6)C13A—C14A—C15A—C16A0.8 (10)
C15A—C16A—C17A—C12A0.3 (9)C15A—C14A—C13A—C12A0.3 (10)
C19A—C20A—C21A—C22A2.2 (9)C17A—C12A—C13A—C14A1.1 (9)
C23A—C24A—C19A—C20A0.1 (8)C11A—C12A—C13A—C14A179.6 (6)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C19A–C24A ring.
D—H···AD—HH···AD···AD—H···A
C24A—H24A···O1BAi0.932.493.348 (8)154
C18A—H18A···Cgii0.972.773.513 (5)134
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC24H18I2O2
Mr592.18
Crystal system, space groupMonoclinic, C2/c
Temperature (K)291
a, b, c (Å)31.222 (4), 5.5684 (8), 27.445 (4)
β (°) 118.680 (2)
V3)4186.1 (10)
Z8
Radiation typeMo Kα
µ (mm1)3.02
Crystal size (mm)0.28 × 0.24 × 0.22
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.485, 0.556
No. of measured, independent and
observed [I > 2σ(I)] reflections
10700, 4111, 2679
Rint0.038
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.101, 1.03
No. of reflections4111
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C24A—H24A···O1BAi0.932.493.348 (8)154
C18A—H18A···Cgii0.972.773.513 (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

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