Isopropyl 2-(5-iodo-7-methyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808038671

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2431

doi:10.1107/S1600536808038671

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Isopropyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 13 November 2008; accepted 19 November 2008; online 26 November 2008)

In the title molecule, C₁₅H₁₇IO₄S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. In the crystal structure, intermolecular I⋯O [2.994 (3) Å] halogen bonding links the molecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by intermolecular sulfinyl–sulfinyl interactions [S⋯O 3.128 (3) Å].

Related literature

For the crystal structures of similar isopropyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see Choi et al. (2008a ,b ). For a review of halogen bonding, see Politzer et al. (2007 ). For a review of carbonyl–carbonyl interactions, see Allen et al. (1998 ).

Experimental

Crystal data

C₁₅H₁₇IO₄S
M_r = 420.25
Monoclinic, C 2/c
a = 17.615 (2) Å
b = 10.0905 (7) Å
c = 19.144 (1) Å
β = 99.177 (2)°
V = 3359.2 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.04 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.480, T_max = 0.667
6667 measured reflections
2897 independent reflections
2172 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.064
S = 1.24
2897 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected interatomic distances (Å)

I⋯O4ⁱ	2.994 (3)
S⋯O4ⁱⁱ	3.128 (3)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038671/cv2478sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038671/cv2478Isup2.hkl

checkCIF report

Comment top

This work is related to our previous communications on the synthesis and structure of isopropyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. isopropyl 2-(5-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and isopropyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008b). Here we report the crystal structure of the title compound, isopropyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.030 (3) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by intermolecular I···O halogen bonding (Politzer et al., 2007) of 2.994 (3) Å and a nearly linear C—I···O angle of 168.51 (9)°, which link the molecules into centrosymmetric dimers (Table 1). These dimers are further packed into ribbons along the c axis by sulfinyl–sulfinyl interactions (Table 1) interpreted as simliar to a type–II carbonyl–carbonyl interaction (Allen et al., 1998).

Related literature top

For the crystal structures of similar isopropyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see Choi et al. (2008a,b). For a review of halogen bonding, see Politzer et al. (2007). For a review of carbonyl–carbonyl interactions, see Allen et al. (1998).

Experimental top

77% 3-Chloroperoxybenzoic acid (123 mg, 0.55 mmol) was added in small portions to a stirred solution of isopropyl 2-(5-iodo-7-methyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (202 mg, 0.5 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 81%, m.p. 396-397 K; R_f = 0.74 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 1.27 (d, J = 6.24 Hz, 6H), 2.46 (s, 3H), 3.06 (s, 3H), 4.00 (s, 2H), 5.03-5.09 (m, 1H), 7.49 (s, 1H), 8.10 (s, 1H); EI-MS 420 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A portion of the crystal packing showing the I···O halogen bonding and S···O interactions by dotted lines [symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, y, -z+1/2; (iii) x, -y+1, z-1/2].

Isopropyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₅H₁₇IO₄S	F(000) = 1664
M_r = 420.25	D_x = 1.662 Mg m⁻³
Monoclinic, C2/c	Melting point = 420–421 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.615 (2) Å	Cell parameters from 5394 reflections
b = 10.0905 (7) Å	θ = 2.2–28.1°
c = 19.144 (1) Å	µ = 2.04 mm⁻¹
β = 99.177 (2)°	T = 298 K
V = 3359.2 (5) Å³	Block, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2172 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.5°
ϕ and ω scans	h = −12→21
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
T_min = 0.480, T_max = 0.667	l = −23→23
6667 measured reflections

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F²) = 0.064	H-atom parameters constrained
S = 1.24	w = 1/[σ²(F_o²)]
2897 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₅H₁₇IO₄S	V = 3359.2 (5) Å³
M_r = 420.25	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.615 (2) Å	µ = 2.04 mm⁻¹
b = 10.0905 (7) Å	T = 298 K
c = 19.144 (1) Å	0.40 × 0.30 × 0.20 mm
β = 99.177 (2)°

Data collection top

Bruker SMART CCD diffractometer	2897 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2172 reflections with I > 2σ(I)
T_min = 0.480, T_max = 0.667	R_int = 0.030
6667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.24	Δρ_max = 0.49 e Å⁻³
2897 reflections	Δρ_min = −0.37 e Å⁻³
192 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 > 2sigma(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
I	0.513353 (18)	0.743648 (18)	−0.024404 (13)	0.04774 (10)
S	0.60070 (6)	0.34161 (6)	0.23510 (5)	0.0450 (2)
O1	0.61238 (16)	0.71392 (18)	0.29955 (13)	0.0445 (7)
O2	0.71791 (17)	0.4874 (2)	0.48324 (13)	0.0503 (7)
O3	0.7643 (2)	0.5249 (3)	0.38247 (15)	0.0783 (10)
O4	0.53494 (17)	0.3086 (2)	0.17899 (13)	0.0554 (7)
C1	0.6014 (2)	0.5163 (3)	0.24557 (19)	0.0408 (9)
C2	0.5868 (2)	0.6160 (2)	0.19074 (19)	0.0382 (9)
C3	0.5656 (2)	0.6170 (3)	0.11784 (18)	0.0389 (9)
H3	0.5604	0.5386	0.0920	0.047*
C4	0.5524 (2)	0.7395 (2)	0.0848 (2)	0.0394 (8)
C5	0.5640 (2)	0.8584 (3)	0.12417 (19)	0.0430 (9)
H5	0.5567	0.9388	0.1003	0.052*
C6	0.5853 (2)	0.8597 (3)	0.19600 (19)	0.0414 (9)
C7	0.5950 (2)	0.7356 (2)	0.2277 (2)	0.0385 (8)
C8	0.6142 (2)	0.5781 (3)	0.30852 (19)	0.0409 (9)
C9	0.6276 (2)	0.5310 (3)	0.3828 (2)	0.0470 (10)
H9A	0.6021	0.4463	0.3851	0.056*
H9B	0.6042	0.5932	0.4116	0.056*
C10	0.7106 (3)	0.5155 (3)	0.4138 (2)	0.0452 (10)
C11	0.7939 (3)	0.4653 (4)	0.5226 (2)	0.0575 (11)
H11	0.8262	0.4217	0.4922	0.069*
C12	0.7830 (3)	0.3742 (4)	0.5829 (2)	0.0690 (13)
H12A	0.7593	0.2933	0.5642	0.083*
H12B	0.7507	0.4166	0.6121	0.083*
H12C	0.8321	0.3548	0.6106	0.083*
C13	0.8288 (3)	0.5958 (5)	0.5478 (3)	0.0918 (17)
H13A	0.7971	0.6382	0.5775	0.110*
H13B	0.8325	0.6513	0.5077	0.110*
H13C	0.8792	0.5813	0.5741	0.110*
C14	0.5999 (3)	0.9856 (3)	0.2391 (2)	0.0615 (12)
H14A	0.5901	0.9698	0.2863	0.092*
H14B	0.5664	1.0544	0.2176	0.092*
H14C	0.6525	1.0125	0.2407	0.092*
C15	0.6855 (3)	0.3293 (4)	0.1950 (3)	0.0887 (19)
H15A	0.6947	0.2381	0.1848	0.133*
H15B	0.7286	0.3636	0.2269	0.133*
H15C	0.6787	0.3796	0.1519	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.0565 (2)	0.04572 (12)	0.04033 (15)	−0.00107 (11)	0.00570 (13)	−0.00037 (10)
S	0.0481 (7)	0.0287 (3)	0.0571 (6)	−0.0014 (4)	0.0050 (5)	0.0060 (3)
O1	0.056 (2)	0.0353 (10)	0.0405 (15)	−0.0035 (10)	0.0028 (14)	0.0011 (9)
O2	0.0467 (19)	0.0623 (14)	0.0407 (16)	0.0041 (13)	0.0029 (14)	0.0026 (12)
O3	0.050 (2)	0.133 (2)	0.054 (2)	0.0157 (18)	0.0137 (18)	0.0208 (17)
O4	0.073 (2)	0.0443 (11)	0.0475 (17)	−0.0087 (12)	0.0045 (16)	−0.0040 (11)
C1	0.042 (2)	0.0309 (13)	0.048 (2)	−0.0029 (14)	0.0013 (18)	0.0044 (13)
C2	0.036 (2)	0.0290 (13)	0.049 (2)	−0.0007 (13)	0.0047 (19)	0.0011 (13)
C3	0.041 (2)	0.0303 (13)	0.044 (2)	−0.0048 (13)	0.0030 (19)	−0.0053 (13)
C4	0.038 (2)	0.0395 (15)	0.040 (2)	−0.0008 (14)	0.0057 (18)	0.0016 (13)
C5	0.049 (3)	0.0282 (13)	0.051 (2)	−0.0017 (14)	0.007 (2)	0.0047 (14)
C6	0.049 (3)	0.0318 (14)	0.042 (2)	−0.0027 (14)	0.0035 (19)	−0.0004 (13)
C7	0.040 (2)	0.0319 (14)	0.041 (2)	−0.0033 (13)	0.0007 (18)	−0.0019 (13)
C8	0.038 (2)	0.0351 (14)	0.048 (2)	−0.0014 (14)	0.0022 (19)	0.0053 (14)
C9	0.046 (3)	0.0473 (16)	0.047 (2)	−0.0063 (17)	0.004 (2)	0.0062 (15)
C10	0.047 (3)	0.0417 (15)	0.047 (2)	0.0019 (16)	0.008 (2)	0.0035 (15)
C11	0.047 (3)	0.078 (2)	0.045 (3)	0.019 (2)	−0.002 (2)	0.0008 (19)
C12	0.084 (4)	0.068 (2)	0.051 (3)	0.014 (2)	−0.002 (3)	0.0033 (19)
C13	0.077 (4)	0.117 (4)	0.076 (4)	−0.037 (3)	−0.004 (3)	0.007 (3)
C14	0.086 (4)	0.0306 (14)	0.064 (3)	−0.0021 (17)	−0.002 (2)	−0.0057 (15)
C15	0.073 (4)	0.052 (2)	0.151 (6)	0.006 (2)	0.049 (4)	−0.001 (2)

Geometric parameters (Å, º) top

I—C4	2.095 (4)	C6—C14	1.514 (4)
I—O4ⁱ	2.994 (3)	C8—C9	1.483 (5)
S—O4	1.486 (3)	C9—C10	1.496 (5)
S—O4ⁱⁱ	3.128 (3)	C9—H9A	0.9700
S—C1	1.773 (3)	C9—H9B	0.9700
S—C15	1.789 (4)	C11—C13	1.500 (6)
O1—C7	1.378 (4)	C11—C12	1.511 (5)
O1—C8	1.381 (3)	C11—H11	0.9800
O2—C10	1.346 (4)	C12—H12A	0.9600
O2—C11	1.445 (6)	C12—H12B	0.9600
O3—C10	1.201 (4)	C12—H12C	0.9600
C1—C8	1.344 (5)	C13—H13A	0.9600
C1—C2	1.447 (5)	C13—H13B	0.9600
C2—C3	1.386 (5)	C13—H13C	0.9600
C2—C7	1.395 (4)	C14—H14A	0.9600
C3—C4	1.392 (4)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.414 (4)	C15—H15A	0.9600
C5—C6	1.367 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.390 (4)

I···O4ⁱ	2.994 (3)	S···O4ⁱⁱ	3.128 (3)

O4—S—C1	107.19 (17)	H9A—C9—H9B	107.6
C4—I—O4ⁱ	168.51 (9)	O3—C10—O2	123.5 (4)
O4—S—C15	106.4 (2)	O3—C10—C9	126.3 (4)
C1—S—C15	97.22 (16)	O2—C10—C9	110.3 (3)
C7—O1—C8	106.2 (2)	O2—C11—C13	109.3 (3)
C10—O2—C11	118.8 (3)	O2—C11—C12	105.8 (4)
C8—C1—C2	108.2 (3)	C13—C11—C12	112.6 (4)
C8—C1—S	124.1 (3)	O2—C11—H11	109.7
C2—C1—S	127.7 (3)	C13—C11—H11	109.7
C3—C2—C7	119.6 (3)	C12—C11—H11	109.7
C3—C2—C1	136.4 (3)	C11—C12—H12A	109.5
C7—C2—C1	104.0 (3)	C11—C12—H12B	109.5
C2—C3—C4	117.6 (3)	H12A—C12—H12B	109.5
C2—C3—H3	121.2	C11—C12—H12C	109.5
C4—C3—H3	121.2	H12A—C12—H12C	109.5
C3—C4—C5	120.8 (4)	H12B—C12—H12C	109.5
C3—C4—I	118.4 (2)	C11—C13—H13A	109.5
C5—C4—I	120.7 (2)	C11—C13—H13B	109.5
C6—C5—C4	122.5 (3)	H13A—C13—H13B	109.5
C6—C5—H5	118.7	C11—C13—H13C	109.5
C4—C5—H5	118.7	H13A—C13—H13C	109.5
C5—C6—C7	115.2 (3)	H13B—C13—H13C	109.5
C5—C6—C14	123.5 (3)	C6—C14—H14A	109.5
C7—C6—C14	121.3 (3)	C6—C14—H14B	109.5
O1—C7—C6	124.8 (3)	H14A—C14—H14B	109.5
O1—C7—C2	110.9 (2)	C6—C14—H14C	109.5
C6—C7—C2	124.2 (4)	H14A—C14—H14C	109.5
C1—C8—O1	110.6 (3)	H14B—C14—H14C	109.5
C1—C8—C9	133.6 (3)	S—C15—H15A	109.5
O1—C8—C9	115.8 (3)	S—C15—H15B	109.5
C8—C9—C10	114.2 (3)	H15A—C15—H15B	109.5
C8—C9—H9A	108.7	S—C15—H15C	109.5
C10—C9—H9A	108.7	H15A—C15—H15C	109.5
C8—C9—H9B	108.7	H15B—C15—H15C	109.5
C10—C9—H9B	108.7

O4—S—C1—C8	137.8 (3)	C5—C6—C7—C2	2.3 (6)
C15—S—C1—C8	−112.5 (4)	C14—C6—C7—C2	−176.2 (4)
O4—S—C1—C2	−40.3 (4)	C3—C2—C7—O1	176.9 (3)
C15—S—C1—C2	69.4 (4)	C1—C2—C7—O1	−0.6 (4)
C8—C1—C2—C3	−175.0 (4)	C3—C2—C7—C6	−1.9 (6)
S—C1—C2—C3	3.4 (7)	C1—C2—C7—C6	−179.4 (4)
C8—C1—C2—C7	1.9 (4)	C2—C1—C8—O1	−2.5 (4)
S—C1—C2—C7	−179.8 (3)	S—C1—C8—O1	179.1 (3)
C7—C2—C3—C4	−0.8 (5)	C2—C1—C8—C9	175.8 (4)
C1—C2—C3—C4	175.7 (4)	S—C1—C8—C9	−2.6 (6)
C2—C3—C4—C5	3.0 (5)	C7—O1—C8—C1	2.1 (4)
C2—C3—C4—I	−176.1 (2)	C7—O1—C8—C9	−176.6 (3)
C3—C4—C5—C6	−2.7 (6)	C1—C8—C9—C10	93.3 (5)
I—C4—C5—C6	176.4 (3)	O1—C8—C9—C10	−88.4 (4)
C4—C5—C6—C7	0.1 (5)	C11—O2—C10—O3	−0.9 (5)
C4—C5—C6—C14	178.5 (4)	C11—O2—C10—C9	178.4 (3)
C8—O1—C7—C6	178.0 (4)	C8—C9—C10—O3	−7.7 (5)
C8—O1—C7—C2	−0.8 (4)	C8—C9—C10—O2	172.9 (2)
C5—C6—C7—O1	−176.4 (3)	C10—O2—C11—C13	86.0 (4)
C14—C6—C7—O1	5.1 (6)	C10—O2—C11—C12	−152.5 (3)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇IO₄S
M_r	420.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	17.615 (2), 10.0905 (7), 19.144 (1)
β (°)	99.177 (2)
V (Å³)	3359.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.04
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.480, 0.667
No. of measured, independent and observed [I > 2σ(I)] reflections	6667, 2897, 2172
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.064, 1.24
No. of reflections	2897
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Selected interatomic distances (Å) top

I···O4ⁱ

2.994 (3)

S···O4ⁱⁱ

3.128 (3)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y, −z+1/2.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o2079. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2250. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2431

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