5-Bromo-2-methyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S160053681201389X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1298

doi:10.1107/S160053681201389X

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5-Bromo-2-methyl-3-(4-methylphenylsulfinyl)-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 28 March 2012; accepted 30 March 2012; online 4 April 2012)

In the title compound, C₁₆H₁₃BrO₂S, the 4-methylphenyl ring makes a dihedral angle of 87.83 (6)° with the mean plane [mean deviation = 0.007 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and Br⋯O contacts [3.099 (2) Å]. The crystal structure also exhibits π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.637 (2) Å, interplanar distance = 3.317 (2) Å and slippage = 1.492 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₃BrO₂S
M_r = 349.23
Monoclinic, P 2₁ /c
a = 14.3470 (2) Å
b = 11.2122 (1) Å
c = 9.6852 (1) Å
β = 107.556 (1)°
V = 1485.41 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 173 K
0.31 × 0.28 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.466, T_max = 0.579
14207 measured reflections
3671 independent reflections
2844 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.086
S = 1.03
3671 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95	2.49	3.420 (3)	165
C9—H9C⋯O2ⁱⁱ	0.98	2.48	3.294 (3)	141
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S160053681201389X/xu5502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201389X/xu5502Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201389X/xu5502Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-bromo-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a) and 3-(4-chlorophenylsulfinyl) (Choi et al., 2010b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofuran fragment is 87.83 (6)°. In the crystal structure (Fig. 2), molecules are linked by weak C–H···O hydrogen bonds (Table 1) and Br···O halogen-bondings between the bromine atom and the O atom of the S=O unit [Br1···O2ⁱ = 3.099 (2) Å, C4—Br1···O2ⁱ = 163.52 (8)°] (Politzer et al., 2007). The crystal packing (Fig. 3) also exhibits weak π···π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2^vii distance of 3.637 (2) Å and an interplanar distance of 3.317 (2) Å resulting in a slippage of 1.492 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran (300 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 424–425 K; R_f = 0.45 (hexane/ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and Br···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x,- y + 1/2,z + 1/2; (ii) - x + 2,y - 1/2,- z + 3/2; (iii) x,- y + 3/2 ,z + 1/2; (iv) x,- y + 1/2,z - 1/2.] (v) - x + 2,y + 1/2,- z + 3/2; (vi) x,- y + 3/2,z - 1/2;
	Fig. 3. A view of the π···π interactions (dotted lines) in the crystal structure of the title compound. H atoms were omitted for clarity. [Symmetry codes: (vii) - x + 2,- y + 1,- z + 1.]

5-Bromo-2-methyl-3-(4-methylphenylsulfinyl)-1-benzofuran top

Crystal data top

C₁₆H₁₃BrO₂S	F(000) = 704
M_r = 349.23	D_x = 1.562 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5020 reflections
a = 14.3470 (2) Å	θ = 2.4–28.1°
b = 11.2122 (1) Å	µ = 2.91 mm⁻¹
c = 9.6852 (1) Å	T = 173 K
β = 107.556 (1)°	Block, colourless
V = 1485.41 (3) Å³	0.31 × 0.28 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3671 independent reflections
Radiation source: rotating anode	2844 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.5°
ϕ and ω scans	h = −18→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.466, T_max = 0.579	l = −12→12
14207 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0381P)² + 0.8792P] where P = (F_o² + 2F_c²)/3
3671 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

C₁₆H₁₃BrO₂S	V = 1485.41 (3) Å³
M_r = 349.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3470 (2) Å	µ = 2.91 mm⁻¹
b = 11.2122 (1) Å	T = 173 K
c = 9.6852 (1) Å	0.31 × 0.28 × 0.21 mm
β = 107.556 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3671 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2844 reflections with I > 2σ(I)
T_min = 0.466, T_max = 0.579	R_int = 0.032
14207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
3671 reflections	Δρ_min = −0.77 e Å⁻³
183 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
Br1	0.79550 (2)	0.16838 (2)	0.52417 (3)	0.04775 (11)
S1	0.73033 (4)	0.67240 (5)	0.20895 (5)	0.02775 (13)
O1	0.94299 (11)	0.66889 (13)	0.57489 (16)	0.0296 (3)
O2	0.73660 (12)	0.58439 (15)	0.09690 (16)	0.0386 (4)
C1	0.81812 (15)	0.63651 (19)	0.3736 (2)	0.0253 (4)
C2	0.83871 (14)	0.52469 (18)	0.4514 (2)	0.0244 (4)
C3	0.80193 (15)	0.40884 (19)	0.4307 (2)	0.0282 (4)
H3	0.7502	0.3872	0.3471	0.034*
C4	0.84473 (17)	0.32647 (19)	0.5384 (2)	0.0312 (5)
C5	0.92198 (17)	0.3549 (2)	0.6600 (2)	0.0339 (5)
H5	0.9485	0.2953	0.7306	0.041*
C6	0.96063 (16)	0.4685 (2)	0.6796 (2)	0.0320 (5)
H6	1.0146	0.4889	0.7608	0.038*
C7	0.91637 (15)	0.55073 (19)	0.5743 (2)	0.0258 (4)
C8	0.88224 (15)	0.7186 (2)	0.4515 (2)	0.0267 (4)
C9	0.89826 (18)	0.84651 (19)	0.4301 (3)	0.0356 (5)
H9A	0.8605	0.8699	0.3316	0.053*
H9B	0.9679	0.8607	0.4442	0.053*
H9C	0.8770	0.8937	0.5002	0.053*
C10	0.62293 (15)	0.63534 (19)	0.2582 (2)	0.0263 (4)
C11	0.59828 (17)	0.7053 (2)	0.3594 (2)	0.0350 (5)
H11	0.6393	0.7691	0.4059	0.042*
C12	0.51270 (19)	0.6806 (2)	0.3919 (3)	0.0444 (6)
H12	0.4960	0.7275	0.4627	0.053*
C13	0.45106 (17)	0.5896 (2)	0.3241 (3)	0.0438 (6)
C14	0.47699 (19)	0.5233 (3)	0.2218 (3)	0.0516 (7)
H14	0.4349	0.4611	0.1728	0.062*
C15	0.56315 (18)	0.5448 (2)	0.1883 (3)	0.0422 (6)
H15	0.5802	0.4976	0.1181	0.051*
C16	0.3583 (2)	0.5640 (3)	0.3611 (4)	0.0680 (9)
H16A	0.3730	0.5576	0.4665	0.102*
H16B	0.3299	0.4889	0.3157	0.102*
H16C	0.3115	0.6290	0.3253	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.05663 (18)	0.02626 (14)	0.05713 (18)	0.00091 (11)	0.01230 (13)	0.00537 (11)
S1	0.0306 (3)	0.0274 (3)	0.0236 (2)	0.0031 (2)	0.0058 (2)	0.00431 (19)
O1	0.0262 (7)	0.0322 (8)	0.0285 (7)	−0.0028 (6)	0.0055 (6)	−0.0021 (6)
O2	0.0464 (10)	0.0442 (10)	0.0271 (8)	0.0076 (8)	0.0138 (7)	−0.0025 (7)
C1	0.0230 (10)	0.0281 (10)	0.0249 (10)	0.0010 (8)	0.0074 (8)	0.0031 (8)
C2	0.0211 (9)	0.0297 (10)	0.0231 (9)	0.0033 (8)	0.0077 (8)	0.0017 (8)
C3	0.0251 (10)	0.0289 (11)	0.0289 (10)	0.0016 (9)	0.0055 (8)	0.0001 (8)
C4	0.0342 (12)	0.0247 (10)	0.0364 (12)	0.0039 (9)	0.0130 (9)	0.0016 (9)
C5	0.0366 (12)	0.0357 (12)	0.0288 (11)	0.0144 (10)	0.0090 (9)	0.0058 (9)
C6	0.0286 (11)	0.0414 (13)	0.0239 (10)	0.0092 (10)	0.0048 (8)	−0.0005 (9)
C7	0.0230 (10)	0.0303 (11)	0.0254 (10)	0.0018 (8)	0.0092 (8)	−0.0019 (8)
C8	0.0243 (10)	0.0314 (11)	0.0267 (10)	0.0008 (9)	0.0108 (8)	0.0010 (8)
C9	0.0413 (13)	0.0290 (12)	0.0384 (12)	−0.0070 (10)	0.0152 (10)	−0.0013 (9)
C10	0.0237 (10)	0.0273 (10)	0.0241 (10)	0.0040 (8)	0.0015 (8)	0.0021 (8)
C11	0.0341 (12)	0.0352 (12)	0.0333 (12)	0.0022 (10)	0.0063 (10)	−0.0069 (9)
C12	0.0373 (13)	0.0571 (17)	0.0396 (14)	0.0115 (12)	0.0127 (11)	−0.0027 (12)
C13	0.0282 (12)	0.0504 (15)	0.0513 (15)	0.0074 (11)	0.0099 (11)	0.0130 (12)
C14	0.0347 (14)	0.0459 (16)	0.0705 (19)	−0.0131 (12)	0.0103 (13)	−0.0137 (14)
C15	0.0379 (13)	0.0411 (14)	0.0459 (14)	−0.0026 (11)	0.0099 (11)	−0.0151 (11)
C16	0.0352 (15)	0.089 (3)	0.082 (2)	0.0073 (16)	0.0223 (15)	0.025 (2)

Geometric parameters (Å, º) top

Br1—C4	1.898 (2)	C8—C9	1.477 (3)
Br1—O2ⁱ	3.0986 (16)	C9—H9A	0.9800
S1—O2	1.4895 (16)	C9—H9B	0.9800
S1—C1	1.755 (2)	C9—H9C	0.9800
S1—C10	1.794 (2)	C10—C15	1.369 (3)
O1—C8	1.368 (2)	C10—C11	1.382 (3)
O1—C7	1.378 (3)	C11—C12	1.384 (4)
C1—C8	1.357 (3)	C11—H11	0.9500
C1—C2	1.446 (3)	C12—C13	1.379 (4)
C2—C3	1.394 (3)	C12—H12	0.9500
C2—C7	1.394 (3)	C13—C14	1.377 (4)
C3—C4	1.390 (3)	C13—C16	1.507 (4)
C3—H3	0.9500	C14—C15	1.391 (4)
C4—C5	1.389 (3)	C14—H14	0.9500
C5—C6	1.379 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.379 (3)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800

C4—Br1—O2ⁱ	163.52 (8)	C8—C9—H9B	109.5
O2—S1—C1	109.01 (10)	H9A—C9—H9B	109.5
O2—S1—C10	106.61 (10)	C8—C9—H9C	109.5
C1—S1—C10	98.26 (9)	H9A—C9—H9C	109.5
C8—O1—C7	106.57 (16)	H9B—C9—H9C	109.5
C8—C1—C2	107.50 (18)	C15—C10—C11	121.0 (2)
C8—C1—S1	121.98 (16)	C15—C10—S1	120.02 (17)
C2—C1—S1	130.52 (16)	C11—C10—S1	118.78 (17)
C3—C2—C7	119.24 (19)	C10—C11—C12	118.8 (2)
C3—C2—C1	136.39 (19)	C10—C11—H11	120.6
C7—C2—C1	104.36 (18)	C12—C11—H11	120.6
C4—C3—C2	116.68 (19)	C13—C12—C11	121.7 (2)
C4—C3—H3	121.7	C13—C12—H12	119.2
C2—C3—H3	121.7	C11—C12—H12	119.2
C5—C4—C3	122.9 (2)	C14—C13—C12	117.9 (2)
C5—C4—Br1	117.37 (17)	C14—C13—C16	121.2 (3)
C3—C4—Br1	119.72 (17)	C12—C13—C16	120.9 (3)
C6—C5—C4	120.9 (2)	C13—C14—C15	121.8 (2)
C6—C5—H5	119.6	C13—C14—H14	119.1
C4—C5—H5	119.6	C15—C14—H14	119.1
C7—C6—C5	116.1 (2)	C10—C15—C14	118.8 (2)
C7—C6—H6	122.0	C10—C15—H15	120.6
C5—C6—H6	122.0	C14—C15—H15	120.6
O1—C7—C6	125.05 (19)	C13—C16—H16A	109.5
O1—C7—C2	110.73 (18)	C13—C16—H16B	109.5
C6—C7—C2	124.2 (2)	H16A—C16—H16B	109.5
C1—C8—O1	110.84 (18)	C13—C16—H16C	109.5
C1—C8—C9	133.5 (2)	H16A—C16—H16C	109.5
O1—C8—C9	115.66 (18)	H16B—C16—H16C	109.5
C8—C9—H9A	109.5

O2—S1—C1—C8	128.69 (18)	C1—C2—C7—C6	−179.4 (2)
C10—S1—C1—C8	−120.49 (18)	C2—C1—C8—O1	−0.3 (2)
O2—S1—C1—C2	−50.8 (2)	S1—C1—C8—O1	−179.90 (14)
C10—S1—C1—C2	60.1 (2)	C2—C1—C8—C9	−179.9 (2)
C8—C1—C2—C3	−179.0 (2)	S1—C1—C8—C9	0.5 (4)
S1—C1—C2—C3	0.5 (4)	C7—O1—C8—C1	0.3 (2)
C8—C1—C2—C7	0.2 (2)	C7—O1—C8—C9	−179.99 (18)
S1—C1—C2—C7	179.73 (17)	O2—S1—C10—C15	−3.5 (2)
C7—C2—C3—C4	1.6 (3)	C1—S1—C10—C15	−116.2 (2)
C1—C2—C3—C4	−179.3 (2)	O2—S1—C10—C11	−178.65 (17)
C2—C3—C4—C5	−1.5 (3)	C1—S1—C10—C11	68.59 (19)
C2—C3—C4—Br1	177.05 (15)	C15—C10—C11—C12	1.5 (3)
C3—C4—C5—C6	−0.2 (4)	S1—C10—C11—C12	176.65 (18)
Br1—C4—C5—C6	−178.77 (17)	C10—C11—C12—C13	−1.1 (4)
C4—C5—C6—C7	1.7 (3)	C11—C12—C13—C14	−0.1 (4)
C8—O1—C7—C6	179.2 (2)	C11—C12—C13—C16	179.9 (2)
C8—O1—C7—C2	−0.2 (2)	C12—C13—C14—C15	1.0 (4)
C5—C6—C7—O1	179.0 (2)	C16—C13—C14—C15	−179.0 (3)
C5—C6—C7—C2	−1.7 (3)	C11—C10—C15—C14	−0.6 (4)
C3—C2—C7—O1	179.38 (18)	S1—C10—C15—C14	−175.7 (2)
C1—C2—C7—O1	0.0 (2)	C13—C14—C15—C10	−0.7 (4)
C3—C2—C7—C6	0.0 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱⁱ	0.95	2.49	3.420 (3)	165
C9—H9C···O2ⁱⁱⁱ	0.98	2.48	3.294 (3)	141

Symmetry codes: (ii) −x+2, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO₂S
M_r	349.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.3470 (2), 11.2122 (1), 9.6852 (1)
β (°)	107.556 (1)
V (Å³)	1485.41 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.31 × 0.28 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.466, 0.579
No. of measured, independent and observed [I > 2σ(I)] reflections	14207, 3671, 2844
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.086, 1.03
No. of reflections	3671
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.77

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.49	3.420 (3)	165.4
C9—H9C···O2ⁱⁱ	0.98	2.48	3.294 (3)	140.8

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+3/2, z+1/2.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o1297. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2721. 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. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1298

doi:10.1107/S160053681201389X

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