3-(4-Bromo­phenyl­sulfin­yl)-2,5,6-trimethyl-1-benzo­furan

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

doi:10.1107/S1600536813017753

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1205

doi:10.1107/S1600536813017753

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3-(4-Bromophenylsulfinyl)-2,5,6-trimethyl-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 19 June 2013; accepted 27 June 2013; online 6 July 2013)

In the title compound, C₁₇H₁₅BrO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.003 (2) Å] of the benzofuran ring system and the mean plane [r.m.s. deviation = 0.006 (2) Å] of the 4-bromophenyl ring is 83.09 (7)°. In the crystal, weak C—H⋯π interactions are observed.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ,b , 2012 ).

Experimental

Crystal data

C₁₇H₁₅BrO₂S
M_r = 363.26
Monoclinic, P 2₁ /c
a = 20.0084 (8) Å
b = 7.1890 (3) Å
c = 10.7804 (4) Å
β = 101.478 (2)°
V = 1519.65 (10) Å³
Z = 4
Mo Kα radiation
μ = 2.84 mm⁻¹
T = 173 K
0.37 × 0.26 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.425, T_max = 0.746
26485 measured reflections
3791 independent reflections
2928 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.05
3791 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯Cg1ⁱ	0.98	2.89	3.537 (4)	124
C11—H11C⋯Cg2ⁱⁱ	0.98	2.78	3.714 (4)	159
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813017753/nc2313sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017753/nc2313Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813017753/nc2313Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 2,5-dimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (Choi et al., 2010a), 4-chlorophenylsulfinyl (Choi et al., 2010b) and 4-bromophenylsulfinyl (Choi et al., 2012) substituents in 3-position, we report here the crystal structure of the title compound.

In the title molecule the benzofuran unit is essentially planar, with a mean deviation of 0.003 (2) Å from the least-squares plane defined by the nine constituent atoms (Fig. 1). The 4-bromophenyl ring is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle between the mean plane of the benzofuran ring system and the 4-bromophenyl ring is 83.09 (7)°. In the crystal structure the molecules are connected by weak C—H···π interactions (Table 1 and Fig. 2), Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively)

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2,5,6-trimethyl-1-benzofuran (278 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 446–447 K; R_f = 0.41 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of the solvent from 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 for Windows (Farrugia, 2012) 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. Fig. 2. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms that does not participate in this interaction are omitted for clarity.Symmetry codes: (i) x, - y + 1/2, z - 1/2; (ii) x, - y + 3/2, z + 1/2; (iii) x, - y +1/2, z + 1/2; (iv) x, - y + 3/2, z - 1/2.]

3-(4-Bromophenylsulfinyl)-2,5,6-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅BrO₂S	F(000) = 736
M_r = 363.26	D_x = 1.588 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 446–447 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 20.0084 (8) Å	Cell parameters from 6275 reflections
b = 7.1890 (3) Å	θ = 3.1–27.2°
c = 10.7804 (4) Å	µ = 2.84 mm⁻¹
β = 101.478 (2)°	T = 173 K
V = 1519.65 (10) Å³	Block, colourless
Z = 4	0.37 × 0.26 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3791 independent reflections
Radiation source: rotating anode	2928 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.071
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.1°
ϕ and ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −7→9
T_min = 0.425, T_max = 0.746	l = −14→14
26485 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0459P)² + 0.8553P] where P = (F_o² + 2F_c²)/3
3791 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₂S	V = 1519.65 (10) Å³
M_r = 363.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.0084 (8) Å	µ = 2.84 mm⁻¹
b = 7.1890 (3) Å	T = 173 K
c = 10.7804 (4) Å	0.37 × 0.26 × 0.05 mm
β = 101.478 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3791 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2928 reflections with I > 2σ(I)
T_min = 0.425, T_max = 0.746	R_int = 0.071
26485 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.75 e Å⁻³
3791 reflections	Δρ_min = −0.86 e Å⁻³
193 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	0.471187 (16)	0.90385 (6)	0.33352 (3)	0.06164 (16)
S1	0.30484 (3)	0.38470 (9)	0.64879 (6)	0.02963 (16)
O1	0.11729 (8)	0.5558 (2)	0.62907 (13)	0.0245 (4)
O2	0.30702 (10)	0.1917 (3)	0.5990 (2)	0.0456 (5)
C1	0.22159 (11)	0.4684 (3)	0.60389 (19)	0.0230 (5)
C2	0.17882 (11)	0.4857 (3)	0.47877 (19)	0.0218 (4)
C3	0.18654 (12)	0.4633 (3)	0.35339 (19)	0.0240 (5)
H3	0.2292	0.4267	0.3354	0.029*
C4	0.13130 (12)	0.4951 (3)	0.25574 (19)	0.0242 (5)
C5	0.06756 (12)	0.5501 (3)	0.28199 (19)	0.0230 (4)
C6	0.06000 (11)	0.5739 (3)	0.40622 (19)	0.0230 (5)
H6	0.0178	0.6124	0.4253	0.028*
C7	0.11582 (11)	0.5398 (3)	0.50083 (18)	0.0220 (4)
C8	0.18216 (12)	0.5111 (3)	0.68885 (19)	0.0245 (5)
C9	0.13935 (14)	0.4700 (4)	0.1205 (2)	0.0327 (6)
H9A	0.1875	0.4477	0.1187	0.049*
H9B	0.1238	0.5826	0.0720	0.049*
H9C	0.1120	0.3635	0.0831	0.049*
C10	0.00712 (13)	0.5824 (4)	0.1766 (2)	0.0302 (5)
H10A	−0.0325	0.6167	0.2123	0.045*
H10B	−0.0030	0.4683	0.1265	0.045*
H10C	0.0174	0.6831	0.1221	0.045*
C11	0.19543 (14)	0.5183 (4)	0.82940 (19)	0.0313 (5)
H11A	0.2425	0.4795	0.8633	0.047*
H11B	0.1639	0.4344	0.8607	0.047*
H11C	0.1887	0.6456	0.8569	0.047*
C12	0.34419 (11)	0.5327 (4)	0.5498 (2)	0.0270 (5)
C13	0.38253 (14)	0.4501 (4)	0.4718 (3)	0.0407 (7)
H13	0.3838	0.3186	0.4644	0.049*
C14	0.41911 (14)	0.5619 (5)	0.4046 (3)	0.0469 (8)
H14	0.4451	0.5078	0.3492	0.056*
C15	0.41750 (12)	0.7519 (5)	0.4186 (2)	0.0379 (7)
C16	0.37837 (13)	0.8355 (4)	0.4953 (2)	0.0354 (6)
H16	0.3768	0.9671	0.5022	0.042*
C17	0.34162 (12)	0.7238 (4)	0.5615 (2)	0.0302 (5)
H17	0.3146	0.7782	0.6151	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04327 (19)	0.1047 (4)	0.03699 (18)	−0.03020 (17)	0.00810 (13)	0.01789 (15)
S1	0.0254 (3)	0.0305 (4)	0.0322 (3)	0.0010 (2)	0.0038 (2)	0.0074 (2)
O1	0.0278 (8)	0.0287 (10)	0.0182 (7)	0.0021 (7)	0.0074 (6)	0.0007 (6)
O2	0.0385 (10)	0.0257 (12)	0.0747 (14)	0.0058 (9)	0.0161 (9)	0.0068 (9)
C1	0.0266 (11)	0.0214 (13)	0.0213 (10)	−0.0025 (9)	0.0052 (8)	0.0014 (8)
C2	0.0257 (10)	0.0181 (12)	0.0222 (10)	−0.0018 (9)	0.0059 (8)	0.0016 (8)
C3	0.0291 (11)	0.0215 (13)	0.0231 (10)	0.0034 (10)	0.0094 (8)	0.0024 (8)
C4	0.0351 (12)	0.0189 (12)	0.0199 (9)	0.0002 (10)	0.0088 (8)	0.0002 (8)
C5	0.0286 (11)	0.0179 (12)	0.0220 (10)	−0.0026 (9)	0.0039 (8)	0.0016 (7)
C6	0.0242 (10)	0.0223 (13)	0.0234 (10)	−0.0005 (9)	0.0067 (8)	0.0009 (8)
C7	0.0294 (11)	0.0198 (13)	0.0188 (9)	−0.0017 (9)	0.0094 (8)	0.0007 (7)
C8	0.0299 (11)	0.0223 (13)	0.0208 (10)	−0.0014 (10)	0.0042 (8)	0.0004 (8)
C9	0.0476 (14)	0.0308 (15)	0.0208 (10)	0.0117 (12)	0.0095 (10)	0.0008 (9)
C10	0.0330 (12)	0.0322 (15)	0.0234 (11)	−0.0006 (11)	0.0006 (9)	0.0014 (9)
C11	0.0427 (14)	0.0321 (15)	0.0186 (10)	0.0015 (12)	0.0052 (9)	−0.0006 (8)
C12	0.0225 (10)	0.0335 (15)	0.0242 (10)	−0.0014 (10)	0.0030 (8)	−0.0001 (9)
C13	0.0395 (15)	0.0385 (18)	0.0480 (15)	0.0000 (13)	0.0185 (12)	−0.0072 (12)
C14	0.0393 (16)	0.063 (2)	0.0438 (16)	−0.0047 (14)	0.0222 (13)	−0.0116 (13)
C15	0.0257 (12)	0.059 (2)	0.0288 (12)	−0.0102 (12)	0.0057 (9)	0.0066 (11)
C16	0.0296 (12)	0.0378 (16)	0.0376 (13)	−0.0048 (12)	0.0040 (10)	0.0070 (11)
C17	0.0272 (11)	0.0325 (15)	0.0322 (11)	−0.0010 (10)	0.0086 (9)	0.0005 (9)

Geometric parameters (Å, º) top

Br1—C15	1.892 (3)	C9—H9A	0.9800
S1—O2	1.492 (2)	C9—H9B	0.9800
S1—C1	1.746 (2)	C9—H9C	0.9800
S1—C12	1.796 (2)	C10—H10A	0.9800
O1—C8	1.368 (3)	C10—H10B	0.9800
O1—C7	1.382 (2)	C10—H10C	0.9800
C1—C8	1.358 (3)	C11—H11A	0.9800
C1—C2	1.452 (3)	C11—H11B	0.9800
C2—C7	1.384 (3)	C11—H11C	0.9800
C2—C3	1.400 (3)	C12—C13	1.380 (3)
C3—C4	1.385 (3)	C12—C17	1.382 (4)
C3—H3	0.9500	C13—C14	1.385 (4)
C4—C5	1.417 (3)	C13—H13	0.9500
C4—C9	1.509 (3)	C14—C15	1.375 (5)
C5—C6	1.388 (3)	C14—H14	0.9500
C5—C10	1.504 (3)	C15—C16	1.384 (4)
C6—C7	1.376 (3)	C16—C17	1.380 (3)
C6—H6	0.9500	C16—H16	0.9500
C8—C11	1.486 (3)	C17—H17	0.9500

O2—S1—C1	108.38 (11)	H9A—C9—H9C	109.5
O2—S1—C12	106.81 (11)	H9B—C9—H9C	109.5
C1—S1—C12	97.93 (11)	C5—C10—H10A	109.5
C8—O1—C7	106.33 (16)	C5—C10—H10B	109.5
C8—C1—C2	107.05 (19)	H10A—C10—H10B	109.5
C8—C1—S1	122.76 (16)	C5—C10—H10C	109.5
C2—C1—S1	129.82 (16)	H10A—C10—H10C	109.5
C7—C2—C3	118.5 (2)	H10B—C10—H10C	109.5
C7—C2—C1	104.66 (18)	C8—C11—H11A	109.5
C3—C2—C1	136.8 (2)	C8—C11—H11B	109.5
C4—C3—C2	119.4 (2)	H11A—C11—H11B	109.5
C4—C3—H3	120.3	C8—C11—H11C	109.5
C2—C3—H3	120.3	H11A—C11—H11C	109.5
C3—C4—C5	120.54 (18)	H11B—C11—H11C	109.5
C3—C4—C9	119.5 (2)	C13—C12—C17	121.3 (2)
C5—C4—C9	120.0 (2)	C13—C12—S1	118.0 (2)
C6—C5—C4	120.2 (2)	C17—C12—S1	120.38 (17)
C6—C5—C10	119.0 (2)	C12—C13—C14	119.0 (3)
C4—C5—C10	120.84 (19)	C12—C13—H13	120.5
C7—C6—C5	117.7 (2)	C14—C13—H13	120.5
C7—C6—H6	121.1	C15—C14—C13	119.5 (2)
C5—C6—H6	121.1	C15—C14—H14	120.3
C6—C7—O1	125.39 (19)	C13—C14—H14	120.3
C6—C7—C2	123.72 (19)	C14—C15—C16	121.7 (2)
O1—C7—C2	110.88 (19)	C14—C15—Br1	119.5 (2)
C1—C8—O1	111.08 (18)	C16—C15—Br1	118.8 (2)
C1—C8—C11	133.3 (2)	C17—C16—C15	118.7 (3)
O1—C8—C11	115.63 (19)	C17—C16—H16	120.7
C4—C9—H9A	109.5	C15—C16—H16	120.7
C4—C9—H9B	109.5	C16—C17—C12	119.8 (2)
H9A—C9—H9B	109.5	C16—C17—H17	120.1
C4—C9—H9C	109.5	C12—C17—H17	120.1

O2—S1—C1—C8	115.6 (2)	C1—C2—C7—C6	179.3 (2)
C12—S1—C1—C8	−133.6 (2)	C3—C2—C7—O1	−179.8 (2)
O2—S1—C1—C2	−56.5 (3)	C1—C2—C7—O1	−0.2 (3)
C12—S1—C1—C2	54.3 (2)	C2—C1—C8—O1	−0.3 (3)
C8—C1—C2—C7	0.3 (3)	S1—C1—C8—O1	−174.01 (17)
S1—C1—C2—C7	173.37 (19)	C2—C1—C8—C11	179.6 (3)
C8—C1—C2—C3	179.8 (3)	S1—C1—C8—C11	6.0 (4)
S1—C1—C2—C3	−7.1 (4)	C7—O1—C8—C1	0.2 (3)
C7—C2—C3—C4	−0.2 (3)	C7—O1—C8—C11	−179.7 (2)
C1—C2—C3—C4	−179.7 (3)	O2—S1—C12—C13	−15.3 (2)
C2—C3—C4—C5	0.1 (4)	C1—S1—C12—C13	−127.3 (2)
C2—C3—C4—C9	−179.7 (2)	O2—S1—C12—C17	171.18 (18)
C3—C4—C5—C6	0.4 (4)	C1—S1—C12—C17	59.2 (2)
C9—C4—C5—C6	−179.8 (2)	C17—C12—C13—C14	0.1 (4)
C3—C4—C5—C10	−179.2 (2)	S1—C12—C13—C14	−173.3 (2)
C9—C4—C5—C10	0.6 (3)	C12—C13—C14—C15	1.2 (4)
C4—C5—C6—C7	−0.9 (3)	C13—C14—C15—C16	−2.2 (4)
C10—C5—C6—C7	178.7 (2)	C13—C14—C15—Br1	176.7 (2)
C5—C6—C7—O1	−179.7 (2)	C14—C15—C16—C17	1.7 (4)
C5—C6—C7—C2	0.8 (4)	Br1—C15—C16—C17	−177.17 (18)
C8—O1—C7—C6	−179.5 (2)	C15—C16—C17—C12	−0.4 (4)
C8—O1—C7—C2	0.0 (3)	C13—C12—C17—C16	−0.5 (4)
C3—C2—C7—C6	−0.3 (4)	S1—C12—C17—C16	172.77 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cg1ⁱ	0.98	2.89	3.537 (4)	124
C11—H11C···Cg2ⁱⁱ	0.98	2.78	3.714 (4)	159

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₂S
M_r	363.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	20.0084 (8), 7.1890 (3), 10.7804 (4)
β (°)	101.478 (2)
V (Å³)	1519.65 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.84
Crystal size (mm)	0.37 × 0.26 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.425, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	26485, 3791, 2928
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.05
No. of reflections	3791
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.86

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cg1ⁱ	0.98	2.89	3.537 (4)	124.4
C11—H11C···Cg2ⁱⁱ	0.98	2.78	3.714 (4)	159.0

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

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

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. & Lee, U. (2012). Acta Cryst. E68, o584. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o543. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2551. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals 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 69| Part 8| August 2013| Page o1205

doi:10.1107/S1600536813017753

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