2,5-Dimethyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzofuran

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

doi:10.1107/S1600536812015450

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1410

doi:10.1107/S1600536812015450

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2,5-Dimethyl-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 23 March 2012; accepted 10 April 2012; online 18 April 2012)

In the title compound, C₁₇H₁₆O₂S, the 4-methylphenyl ring makes a dihedral angle of 88.28 (5)° with the mean plane [mean deviation = 0.009 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₁₇H₁₆O₂S
M_r = 284.36
Orthorhombic, P n a 2₁
a = 13.072 (2) Å
b = 6.1790 (11) Å
c = 17.979 (3) Å
V = 1452.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.37 × 0.23 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.624, T_max = 0.746
13920 measured reflections
3587 independent reflections
3101 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.03
3587 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1729 Friedel pairs
Flack parameter: −0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.95	2.60	3.334 (2)	134
C17—H17B⋯O1ⁱⁱ	0.98	2.52	3.387 (3)	148
C10—H10B⋯Cgⁱⁱⁱ	0.98	2.74	3.538 (3)	139
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iii) x, y-1, z.

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/S1600536812015450/fy2054sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015450/fy2054Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015450/fy2054Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2,5-dimethyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a), 3-(4-chlorophenylsulfinyl) (Choi et al., 2010b) and 3-(4-bromophenylsulfinyl) (Choi et al., 2012) 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 0.009 (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 benzofurn fragment is 88.28 (5)°. In the crystal structure, molecules are connected by weak intermolecular C—H···O hydrogen bonds (Fig. 2 & Table 1) and C—H···π interactions (Fig. 3 & Table 1, Cg is the centroid of the C2–C7 benzene ring).

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%, 291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2,5-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (322 mg, 1.2 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 412–413 K; R_f = 0.44 (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 benzene 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 hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen bonding were omitted for clarity. [Symmetry codes: (i) x - 1/2, - y + 1/2, z ; (ii) - x + 1, - y + 1, z + 1/2; (iv) x + 1/2, - y + 1/2, z; (v) - x + 1, - y + 1, z - 1/2.]
	Fig. 3. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen bonding were omitted for clarity. [Symmetry codes: (iii) x, y - 1, z; (vi) x, y + 1, z.]

2,5-Dimethyl-3-(4-methylphenylsulfinyl)-1-benzofuran top

Crystal data top

C₁₇H₁₆O₂S	F(000) = 600
M_r = 284.36	D_x = 1.301 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4157 reflections
a = 13.072 (2) Å	θ = 2.3–24.8°
b = 6.1790 (11) Å	µ = 0.22 mm⁻¹
c = 17.979 (3) Å	T = 173 K
V = 1452.2 (4) Å³	Block, colourless
Z = 4	0.37 × 0.23 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3587 independent reflections
Radiation source: rotating anode	3101 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.036
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
ϕ and ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
T_min = 0.624, T_max = 0.746	l = −23→23
13920 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0445P)² + 0.1605P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3587 reflections	Δρ_max = 0.20 e Å⁻³
184 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1729 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (7)

Crystal data top

C₁₇H₁₆O₂S	V = 1452.2 (4) Å³
M_r = 284.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.072 (2) Å	µ = 0.22 mm⁻¹
b = 6.1790 (11) Å	T = 173 K
c = 17.979 (3) Å	0.37 × 0.23 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3587 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3101 reflections with I > 2σ(I)
T_min = 0.624, T_max = 0.746	R_int = 0.036
13920 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.20 e Å⁻³
S = 1.03	Δρ_min = −0.24 e Å⁻³
3587 reflections	Absolute structure: Flack (1983), 1729 Friedel pairs
184 parameters	Absolute structure parameter: −0.01 (7)
1 restraint

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
S1	0.68387 (4)	0.23443 (8)	0.43774 (3)	0.05093 (14)
O1	0.60322 (10)	0.2839 (2)	0.22842 (8)	0.0447 (3)
O2	0.79502 (12)	0.2480 (3)	0.45451 (10)	0.0708 (5)
C1	0.66469 (12)	0.3081 (3)	0.34471 (11)	0.0379 (4)
C2	0.70684 (12)	0.4873 (2)	0.30262 (10)	0.0332 (3)
C3	0.77327 (12)	0.6586 (3)	0.31664 (11)	0.0372 (4)
H3	0.8017	0.6784	0.3648	0.045*
C4	0.79736 (14)	0.7997 (3)	0.25939 (12)	0.0424 (4)
C5	0.75333 (16)	0.7692 (3)	0.18910 (12)	0.0482 (5)
H5	0.7702	0.8677	0.1504	0.058*
C6	0.68661 (15)	0.6026 (3)	0.17362 (10)	0.0464 (4)
H6	0.6566	0.5850	0.1259	0.056*
C7	0.66586 (12)	0.4626 (3)	0.23164 (10)	0.0373 (4)
C8	0.60458 (13)	0.1927 (3)	0.29798 (12)	0.0419 (4)
C9	0.87197 (17)	0.9835 (3)	0.27175 (15)	0.0580 (6)
H9A	0.8709	1.0260	0.3243	0.087*
H9B	0.8523	1.1073	0.2408	0.087*
H9C	0.9410	0.9362	0.2582	0.087*
C10	0.54077 (15)	−0.0042 (3)	0.30769 (17)	0.0602 (6)
H10A	0.5488	−0.0592	0.3585	0.090*
H10B	0.5626	−0.1152	0.2722	0.090*
H10C	0.4688	0.0320	0.2988	0.090*
C11	0.62497 (13)	0.4678 (3)	0.47906 (10)	0.0407 (4)
C12	0.52077 (14)	0.4978 (3)	0.47194 (11)	0.0455 (4)
H12	0.4809	0.3981	0.4440	0.055*
C13	0.47520 (14)	0.6721 (4)	0.50530 (11)	0.0473 (4)
H13	0.4035	0.6923	0.5000	0.057*
C14	0.53160 (17)	0.8206 (3)	0.54687 (10)	0.0472 (5)
C15	0.63554 (18)	0.7839 (4)	0.55478 (11)	0.0529 (5)
H15	0.6753	0.8810	0.5838	0.063*
C16	0.68289 (14)	0.6082 (4)	0.52116 (11)	0.0486 (5)
H16	0.7543	0.5851	0.5271	0.058*
C17	0.4802 (2)	1.0140 (4)	0.58236 (13)	0.0626 (6)
H17A	0.5321	1.1069	0.6053	0.094*
H17B	0.4320	0.9643	0.6205	0.094*
H17C	0.4431	1.0960	0.5443	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0432 (2)	0.0524 (3)	0.0572 (3)	0.0094 (2)	0.0020 (2)	0.0228 (2)
O1	0.0372 (7)	0.0416 (7)	0.0554 (8)	0.0033 (5)	−0.0021 (6)	−0.0123 (6)
O2	0.0427 (8)	0.1013 (12)	0.0683 (12)	0.0268 (8)	−0.0071 (7)	0.0186 (9)
C1	0.0299 (8)	0.0329 (8)	0.0510 (10)	0.0048 (6)	0.0042 (7)	0.0049 (7)
C2	0.0281 (7)	0.0322 (7)	0.0393 (9)	0.0079 (6)	0.0039 (6)	0.0027 (7)
C3	0.0280 (8)	0.0372 (8)	0.0463 (10)	0.0022 (6)	0.0015 (7)	0.0002 (7)
C4	0.0330 (10)	0.0349 (9)	0.0592 (12)	0.0053 (7)	0.0113 (8)	0.0065 (8)
C5	0.0470 (12)	0.0485 (11)	0.0491 (12)	0.0105 (8)	0.0163 (9)	0.0134 (8)
C6	0.0486 (11)	0.0535 (11)	0.0372 (10)	0.0151 (9)	0.0034 (8)	0.0018 (8)
C7	0.0311 (8)	0.0378 (8)	0.0429 (9)	0.0078 (7)	0.0009 (7)	−0.0067 (7)
C8	0.0281 (9)	0.0335 (8)	0.0642 (12)	0.0062 (7)	0.0052 (8)	−0.0022 (8)
C9	0.0430 (11)	0.0409 (10)	0.0902 (17)	−0.0045 (9)	0.0144 (10)	0.0083 (10)
C10	0.0396 (10)	0.0380 (10)	0.1032 (19)	−0.0061 (8)	0.0087 (12)	−0.0085 (11)
C11	0.0326 (9)	0.0529 (10)	0.0367 (9)	−0.0013 (7)	0.0003 (7)	0.0173 (8)
C12	0.0329 (9)	0.0591 (11)	0.0445 (10)	−0.0029 (8)	−0.0024 (8)	0.0038 (9)
C13	0.0319 (9)	0.0677 (12)	0.0422 (10)	0.0019 (9)	0.0002 (8)	0.0051 (9)
C14	0.0505 (12)	0.0567 (11)	0.0344 (9)	−0.0048 (9)	0.0035 (8)	0.0120 (8)
C15	0.0536 (13)	0.0640 (13)	0.0411 (10)	−0.0184 (10)	−0.0084 (9)	0.0090 (9)
C16	0.0321 (9)	0.0685 (12)	0.0451 (11)	−0.0071 (9)	−0.0069 (8)	0.0181 (9)
C17	0.0751 (15)	0.0605 (13)	0.0521 (13)	−0.0027 (12)	0.0094 (11)	0.0035 (10)

Geometric parameters (Å, º) top

S1—O2	1.4864 (17)	C9—H9B	0.9800
S1—C1	1.751 (2)	C9—H9C	0.9800
S1—C11	1.795 (2)	C10—H10A	0.9800
O1—C8	1.372 (3)	C10—H10B	0.9800
O1—C7	1.376 (2)	C10—H10C	0.9800
C1—C8	1.354 (3)	C11—C16	1.378 (3)
C1—C2	1.450 (2)	C11—C12	1.381 (3)
C2—C3	1.392 (2)	C12—C13	1.369 (3)
C2—C7	1.392 (3)	C12—H12	0.9500
C3—C4	1.385 (3)	C13—C14	1.394 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.401 (3)	C14—C15	1.385 (3)
C4—C9	1.513 (3)	C14—C17	1.512 (3)
C5—C6	1.378 (3)	C15—C16	1.388 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.382 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—H17A	0.9800
C8—C10	1.485 (2)	C17—H17B	0.9800
C9—H9A	0.9800	C17—H17C	0.9800

O2—S1—C1	108.60 (9)	H9A—C9—H9C	109.5
O2—S1—C11	106.86 (10)	H9B—C9—H9C	109.5
C1—S1—C11	97.17 (8)	C8—C10—H10A	109.5
C8—O1—C7	106.49 (14)	C8—C10—H10B	109.5
C8—C1—C2	107.41 (17)	H10A—C10—H10B	109.5
C8—C1—S1	122.59 (14)	C8—C10—H10C	109.5
C2—C1—S1	129.99 (14)	H10A—C10—H10C	109.5
C3—C2—C7	119.29 (16)	H10B—C10—H10C	109.5
C3—C2—C1	136.31 (17)	C16—C11—C12	120.55 (18)
C7—C2—C1	104.40 (15)	C16—C11—S1	119.83 (14)
C4—C3—C2	119.07 (17)	C12—C11—S1	119.51 (15)
C4—C3—H3	120.5	C13—C12—C11	119.63 (19)
C2—C3—H3	120.5	C13—C12—H12	120.2
C3—C4—C5	119.48 (17)	C11—C12—H12	120.2
C3—C4—C9	120.64 (19)	C12—C13—C14	121.49 (18)
C5—C4—C9	119.87 (18)	C12—C13—H13	119.3
C6—C5—C4	122.87 (18)	C14—C13—H13	119.3
C6—C5—H5	118.6	C15—C14—C13	117.8 (2)
C4—C5—H5	118.6	C15—C14—C17	121.5 (2)
C5—C6—C7	116.07 (18)	C13—C14—C17	120.7 (2)
C5—C6—H6	122.0	C14—C15—C16	121.39 (19)
C7—C6—H6	122.0	C14—C15—H15	119.3
O1—C7—C6	125.98 (17)	C16—C15—H15	119.3
O1—C7—C2	110.81 (16)	C11—C16—C15	119.12 (18)
C6—C7—C2	123.22 (17)	C11—C16—H16	120.4
C1—C8—O1	110.90 (15)	C15—C16—H16	120.4
C1—C8—C10	133.2 (2)	C14—C17—H17A	109.5
O1—C8—C10	115.87 (19)	C14—C17—H17B	109.5
C4—C9—H9A	109.5	H17A—C17—H17B	109.5
C4—C9—H9B	109.5	C14—C17—H17C	109.5
H9A—C9—H9B	109.5	H17A—C17—H17C	109.5
C4—C9—H9C	109.5	H17B—C17—H17C	109.5

O2—S1—C1—C8	133.66 (16)	C1—C2—C7—C6	179.67 (15)
C11—S1—C1—C8	−115.81 (15)	C2—C1—C8—O1	−0.62 (18)
O2—S1—C1—C2	−44.98 (18)	S1—C1—C8—O1	−179.53 (11)
C11—S1—C1—C2	65.56 (16)	C2—C1—C8—C10	−179.34 (18)
C8—C1—C2—C3	−178.81 (18)	S1—C1—C8—C10	1.8 (3)
S1—C1—C2—C3	0.0 (3)	C7—O1—C8—C1	0.57 (18)
C8—C1—C2—C7	0.41 (17)	C7—O1—C8—C10	179.54 (14)
S1—C1—C2—C7	179.21 (13)	O2—S1—C11—C16	−4.03 (17)
C7—C2—C3—C4	−0.3 (2)	C1—S1—C11—C16	−115.99 (15)
C1—C2—C3—C4	178.80 (17)	O2—S1—C11—C12	179.77 (14)
C2—C3—C4—C5	1.0 (2)	C1—S1—C11—C12	67.80 (15)
C2—C3—C4—C9	−177.99 (16)	C16—C11—C12—C13	1.8 (3)
C3—C4—C5—C6	−0.4 (3)	S1—C11—C12—C13	178.02 (15)
C9—C4—C5—C6	178.59 (17)	C11—C12—C13—C14	−0.3 (3)
C4—C5—C6—C7	−0.8 (3)	C12—C13—C14—C15	−1.3 (3)
C8—O1—C7—C6	179.98 (16)	C12—C13—C14—C17	179.07 (18)
C8—O1—C7—C2	−0.30 (17)	C13—C14—C15—C16	1.5 (3)
C5—C6—C7—O1	−178.81 (15)	C17—C14—C15—C16	−178.94 (19)
C5—C6—C7—C2	1.5 (3)	C12—C11—C16—C15	−1.7 (3)
C3—C2—C7—O1	179.32 (13)	S1—C11—C16—C15	−177.86 (14)
C1—C2—C7—O1	−0.07 (17)	C14—C15—C16—C11	0.0 (3)
C3—C2—C7—C6	−0.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.95	2.60	3.334 (2)	134
C17—H17B···O1ⁱⁱ	0.98	2.52	3.387 (3)	148
C10—H10B···Cgⁱⁱⁱ	0.98	2.74	3.538 (3)	139

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₂S
M_r	284.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	13.072 (2), 6.1790 (11), 17.979 (3)
V (Å³)	1452.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.37 × 0.23 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.624, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13920, 3587, 3101
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.03
No. of reflections	3587
No. of parameters	184
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24
Absolute structure	Flack (1983), 1729 Friedel pairs
Absolute structure parameter	−0.01 (7)

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

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.95	2.60	3.334 (2)	134.4
C17—H17B···O1ⁱⁱ	0.98	2.52	3.387 (3)	148.0
C10—H10B···Cgⁱⁱⁱ	0.98	2.74	3.538 (3)	138.5

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

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. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science 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 68| Part 5| May 2012| Page o1410

doi:10.1107/S1600536812015450

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