5-Fluoro-2-methyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

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

doi:10.1107/S1600536814006321

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o482

doi:10.1107/S1600536814006321

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5-Fluoro-2-methyl-3-(3-methylphenylsulfonyl)-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 20 March 2014; accepted 21 March 2014; online 26 March 2014)

In the title compound, C₁₆H₁₃FO₃S, the dihedral angle between the mean planes of the benzofuran ring system and the 3-methylphenyl ring is 80.96 (4)°. In the crystal, molecules are linked via pairs of π–π interactions between furan and benzene rings, with centroid–centroid distances of 3.758 (1) and 3.771 (1) Å. A similar interaction is found between furan rings, with a centroid–centroid distance of 3.661 (1) Å between neighbouring molecules. The molecules stack along the a-axis direction. In addition, C—H⋯O and C—H⋯π hydrogen bonds are observed between inversion-related dimers.

CCDC reference: 993004

Related literature

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

Experimental

Crystal data

C₁₆H₁₃FO₃S
M_r = 304.32
Triclinic, $[P \overline 1]$
a = 7.4406 (1) Å
b = 9.1291 (2) Å
c = 11.2073 (2) Å
α = 82.891 (1)°
β = 73.301 (1)°
γ = 77.613 (1)°
V = 710.62 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.37 × 0.30 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.695, T_max = 0.746
12591 measured reflections
3263 independent reflections
2868 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.103
S = 1.07
3263 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 3-methylphenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.95	2.51	3.450 (2)	172
C6—H6⋯Cg3ⁱⁱ	0.95	2.76	3.556 (2)	142
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y+1, -z+1.

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

CCDC reference: 993004

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814006321/bg2523sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006321/bg2523Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006321/bg2523Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-fluoro-2-methyl-3-(3-methylphenylsulfanyl)-1-benzofuran (245 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with a 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. 375–376 K; R_f = 0.51 (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 diisopropyl ether, at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms, respectively. U_iso (H) = 1.2U_eq (C) for aryl and 1.5U_eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).

Results and discussion top

As a part of our ongoing study of 5-fluoro-2-methyl-1-benzofuran derivatives containing phenylsulfonyl (Choi et al., 2010a), 4-fluorophenylsulfonyl (Choi et al., 2010b) and 4-methylphenylsulfonyl (Choi et al., 2012) substituents in the 3-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.003 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 80.96 (4)°.

In the crystal structure (Fig. 2), the molecules are linked via pairs of π···π interactions between the furan and benzene rings, and between the furan rings of neighbouring molecules. The molecules stack along the a-axis direction. The relevant centroid names for π···π stacking interactions are Cg1 for the furan ring (C1/C2/C7/O1/O8) and Cg2 for the benzene ring (C2–C7). The centroid-centroid separations of Cg1···Cg2ⁱⁱ [(ii): - x + 1, - y + 1, - z + 1], Cg1···Cg2ⁱⁱⁱ and Cg1···Cg1ⁱⁱⁱ [(iii): - x + 2,- y + 1, - z + 1] are 3.758 (1), 3.771 (1) and 3.661 (1) Å, respectively. The slippages of Cg1···Cg2ⁱⁱ, Cg1···Cg2ⁱⁱⁱ and Cg1···Cg1ⁱⁱⁱ are 1.227 (1), 1.266 (1) Å and 0.887 (1) Å, respectively. In the crystal packing (Fig. 2), intermolecular C—H···O and C—H···π hydrogen bonds are observed between inversion-related dimers.

Related literature top

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

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 molecule with the atom numbering scheme The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H..O, C—H···π and π···π 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 + 2, - y, - z + 1 ; (ii) - x + 1,- y + 1,- z + 1; (iii)- x + 2,- y + 1, - z + 1

5-Fluoro-2-methyl-3-(3-methylphenylsulfonyl)-1-benzofuran top

Crystal data top

C₁₆H₁₃FO₃S	Z = 2
M_r = 304.32	F(000) = 316
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Melting point = 375–376 K
a = 7.4406 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1291 (2) Å	Cell parameters from 5506 reflections
c = 11.2073 (2) Å	θ = 2.9–27.5°
α = 82.891 (1)°	µ = 0.25 mm⁻¹
β = 73.301 (1)°	T = 173 K
γ = 77.613 (1)°	Block, colourless
V = 710.62 (2) Å³	0.37 × 0.30 × 0.28 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3263 independent reflections
Radiation source: rotating anode	2868 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.695, T_max = 0.746	l = −14→14
12591 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.056P)² + 0.1689P] where P = (F_o² + 2F_c²)/3
3263 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₆H₁₃FO₃S	γ = 77.613 (1)°
M_r = 304.32	V = 710.62 (2) Å³
Triclinic, P1	Z = 2
a = 7.4406 (1) Å	Mo Kα radiation
b = 9.1291 (2) Å	µ = 0.25 mm⁻¹
c = 11.2073 (2) Å	T = 173 K
α = 82.891 (1)°	0.37 × 0.30 × 0.28 mm
β = 73.301 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3263 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2868 reflections with I > 2σ(I)
T_min = 0.695, T_max = 0.746	R_int = 0.026
12591 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	Δρ_max = 0.26 e Å⁻³
3263 reflections	Δρ_min = −0.41 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
S1	0.87603 (5)	0.18979 (4)	0.70443 (3)	0.03242 (12)
F1	0.84714 (17)	0.30138 (12)	0.19261 (9)	0.0556 (3)
O1	0.69505 (15)	0.60973 (11)	0.60126 (11)	0.0391 (3)
O2	1.02286 (15)	0.10305 (12)	0.61294 (11)	0.0395 (3)
O3	0.91181 (16)	0.21354 (13)	0.81879 (11)	0.0432 (3)
C1	0.80671 (19)	0.36430 (15)	0.63233 (14)	0.0310 (3)
C2	0.79931 (18)	0.39130 (15)	0.50423 (14)	0.0295 (3)
C3	0.8409 (2)	0.30421 (15)	0.40267 (14)	0.0338 (3)
H3	0.8885	0.1990	0.4076	0.041*
C4	0.8087 (2)	0.38018 (17)	0.29498 (15)	0.0382 (3)
C5	0.7414 (2)	0.53393 (18)	0.28163 (16)	0.0404 (4)
H5	0.7240	0.5792	0.2037	0.048*
C6	0.7004 (2)	0.61985 (16)	0.38156 (16)	0.0389 (4)
H6	0.6545	0.7252	0.3756	0.047*
C7	0.7292 (2)	0.54522 (15)	0.49103 (15)	0.0333 (3)
C8	0.7415 (2)	0.49761 (17)	0.68625 (15)	0.0371 (3)
C9	0.7072 (3)	0.5457 (2)	0.81330 (18)	0.0531 (5)
H9A	0.5697	0.5784	0.8494	0.080*
H9B	0.7729	0.6292	0.8091	0.080*
H9C	0.7562	0.4613	0.8656	0.080*
C10	0.6704 (2)	0.10864 (15)	0.74169 (13)	0.0300 (3)
C11	0.6516 (2)	0.01107 (16)	0.66260 (14)	0.0354 (3)
H11	0.7496	−0.0155	0.5888	0.042*
C12	0.4846 (2)	−0.04647 (17)	0.69504 (16)	0.0404 (4)
H12	0.4678	−0.1138	0.6427	0.048*
C13	0.3430 (2)	−0.00721 (16)	0.80208 (16)	0.0373 (3)
H13	0.2298	−0.0480	0.8220	0.045*
C14	0.3615 (2)	0.09077 (15)	0.88184 (14)	0.0319 (3)
C15	0.5287 (2)	0.14767 (16)	0.85034 (13)	0.0311 (3)
H15	0.5465	0.2137	0.9034	0.037*
C16	0.2048 (2)	0.13571 (19)	0.99669 (14)	0.0414 (4)
H16A	0.1115	0.2202	0.9746	0.062*
H16B	0.2589	0.1658	1.0579	0.062*
H16C	0.1415	0.0505	1.0327	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02348 (19)	0.0338 (2)	0.0379 (2)	−0.00384 (14)	−0.00764 (15)	0.00143 (14)
F1	0.0765 (8)	0.0477 (6)	0.0407 (5)	−0.0112 (5)	−0.0125 (5)	−0.0050 (4)
O1	0.0349 (6)	0.0270 (5)	0.0518 (6)	−0.0042 (4)	−0.0050 (5)	−0.0076 (4)
O2	0.0261 (5)	0.0355 (5)	0.0482 (6)	0.0016 (4)	−0.0033 (5)	0.0008 (5)
O3	0.0350 (6)	0.0538 (7)	0.0446 (6)	−0.0116 (5)	−0.0163 (5)	0.0018 (5)
C1	0.0224 (6)	0.0298 (7)	0.0390 (7)	−0.0061 (5)	−0.0045 (6)	−0.0022 (5)
C2	0.0202 (6)	0.0248 (6)	0.0407 (7)	−0.0046 (5)	−0.0047 (6)	0.0014 (5)
C3	0.0300 (7)	0.0251 (6)	0.0421 (8)	−0.0036 (5)	−0.0050 (6)	−0.0009 (6)
C4	0.0370 (8)	0.0356 (7)	0.0403 (8)	−0.0089 (6)	−0.0062 (7)	−0.0025 (6)
C5	0.0354 (8)	0.0374 (8)	0.0460 (9)	−0.0085 (6)	−0.0112 (7)	0.0091 (7)
C6	0.0309 (8)	0.0252 (7)	0.0568 (10)	−0.0034 (6)	−0.0106 (7)	0.0058 (6)
C7	0.0230 (7)	0.0253 (6)	0.0478 (8)	−0.0043 (5)	−0.0034 (6)	−0.0036 (6)
C8	0.0279 (7)	0.0357 (7)	0.0464 (8)	−0.0093 (6)	−0.0042 (6)	−0.0065 (6)
C9	0.0540 (11)	0.0512 (10)	0.0535 (10)	−0.0120 (8)	−0.0058 (9)	−0.0193 (8)
C10	0.0257 (7)	0.0277 (6)	0.0346 (7)	−0.0026 (5)	−0.0089 (6)	0.0033 (5)
C11	0.0317 (7)	0.0290 (7)	0.0405 (8)	0.0006 (6)	−0.0056 (6)	−0.0045 (6)
C12	0.0374 (8)	0.0281 (7)	0.0556 (10)	−0.0032 (6)	−0.0113 (7)	−0.0110 (6)
C13	0.0303 (7)	0.0280 (7)	0.0519 (9)	−0.0065 (6)	−0.0093 (7)	0.0009 (6)
C14	0.0282 (7)	0.0289 (7)	0.0354 (7)	−0.0022 (5)	−0.0090 (6)	0.0059 (5)
C15	0.0295 (7)	0.0311 (7)	0.0319 (7)	−0.0031 (5)	−0.0103 (6)	0.0008 (5)
C16	0.0314 (8)	0.0525 (9)	0.0358 (8)	−0.0078 (7)	−0.0045 (6)	0.0025 (7)

Geometric parameters (Å, º) top

S1—O3	1.4319 (12)	C8—C9	1.478 (2)
S1—O2	1.4346 (11)	C9—H9A	0.9800
S1—C1	1.7394 (14)	C9—H9B	0.9800
S1—C10	1.7626 (14)	C9—H9C	0.9800
F1—C4	1.3575 (18)	C10—C11	1.385 (2)
O1—C8	1.368 (2)	C10—C15	1.389 (2)
O1—C7	1.3686 (18)	C11—C12	1.387 (2)
C1—C8	1.357 (2)	C11—H11	0.9500
C1—C2	1.441 (2)	C12—C13	1.377 (2)
C2—C3	1.393 (2)	C12—H12	0.9500
C2—C7	1.3954 (19)	C13—C14	1.393 (2)
C3—C4	1.372 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.386 (2)
C4—C5	1.390 (2)	C14—C16	1.499 (2)
C5—C6	1.371 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.377 (2)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800

O3—S1—O2	119.73 (7)	C8—C9—H9A	109.5
O3—S1—C1	108.28 (7)	C8—C9—H9B	109.5
O2—S1—C1	107.74 (7)	H9A—C9—H9B	109.5
O3—S1—C10	108.10 (7)	C8—C9—H9C	109.5
O2—S1—C10	108.25 (7)	H9A—C9—H9C	109.5
C1—S1—C10	103.57 (6)	H9B—C9—H9C	109.5
C8—O1—C7	107.14 (11)	C11—C10—C15	121.75 (13)
C8—C1—C2	107.50 (13)	C11—C10—S1	120.15 (11)
C8—C1—S1	127.01 (12)	C15—C10—S1	118.09 (11)
C2—C1—S1	125.42 (11)	C10—C11—C12	117.64 (14)
C3—C2—C7	119.40 (14)	C10—C11—H11	121.2
C3—C2—C1	136.00 (13)	C12—C11—H11	121.2
C7—C2—C1	104.60 (13)	C13—C12—C11	120.88 (14)
C4—C3—C2	115.65 (13)	C13—C12—H12	119.6
C4—C3—H3	122.2	C11—C12—H12	119.6
C2—C3—H3	122.2	C12—C13—C14	121.61 (14)
F1—C4—C3	118.38 (14)	C12—C13—H13	119.2
F1—C4—C5	116.81 (15)	C14—C13—H13	119.2
C3—C4—C5	124.80 (15)	C15—C14—C13	117.73 (14)
C6—C5—C4	119.62 (15)	C15—C14—C16	120.97 (13)
C6—C5—H5	120.2	C13—C14—C16	121.30 (14)
C4—C5—H5	120.2	C14—C15—C10	120.38 (13)
C5—C6—C7	116.43 (13)	C14—C15—H15	119.8
C5—C6—H6	121.8	C10—C15—H15	119.8
C7—C6—H6	121.8	C14—C16—H16A	109.5
O1—C7—C6	125.55 (13)	C14—C16—H16B	109.5
O1—C7—C2	110.36 (13)	H16A—C16—H16B	109.5
C6—C7—C2	124.09 (14)	C14—C16—H16C	109.5
C1—C8—O1	110.40 (14)	H16A—C16—H16C	109.5
C1—C8—C9	134.70 (16)	H16B—C16—H16C	109.5
O1—C8—C9	114.88 (14)

O3—S1—C1—C8	−18.19 (15)	C1—C2—C7—C6	179.58 (13)
O2—S1—C1—C8	−149.03 (13)	C2—C1—C8—O1	−0.94 (16)
C10—S1—C1—C8	96.42 (14)	S1—C1—C8—O1	−178.00 (10)
O3—S1—C1—C2	165.25 (11)	C2—C1—C8—C9	177.59 (17)
O2—S1—C1—C2	34.41 (13)	S1—C1—C8—C9	0.5 (3)
C10—S1—C1—C2	−80.14 (13)	C7—O1—C8—C1	0.89 (16)
C8—C1—C2—C3	−178.42 (16)	C7—O1—C8—C9	−177.96 (13)
S1—C1—C2—C3	−1.3 (2)	O3—S1—C10—C11	−149.08 (12)
C8—C1—C2—C7	0.61 (15)	O2—S1—C10—C11	−18.00 (14)
S1—C1—C2—C7	177.72 (10)	C1—S1—C10—C11	96.18 (13)
C7—C2—C3—C4	0.2 (2)	O3—S1—C10—C15	32.04 (13)
C1—C2—C3—C4	179.12 (15)	O2—S1—C10—C15	163.13 (11)
C2—C3—C4—F1	179.80 (13)	C1—S1—C10—C15	−82.69 (12)
C2—C3—C4—C5	0.8 (2)	C15—C10—C11—C12	0.4 (2)
F1—C4—C5—C6	−179.85 (14)	S1—C10—C11—C12	−178.41 (11)
C3—C4—C5—C6	−0.8 (3)	C10—C11—C12—C13	0.1 (2)
C4—C5—C6—C7	−0.2 (2)	C11—C12—C13—C14	−0.2 (2)
C8—O1—C7—C6	179.87 (14)	C12—C13—C14—C15	−0.3 (2)
C8—O1—C7—C2	−0.49 (15)	C12—C13—C14—C16	178.60 (14)
C5—C6—C7—O1	−179.25 (14)	C13—C14—C15—C10	0.8 (2)
C5—C6—C7—C2	1.2 (2)	C16—C14—C15—C10	−178.06 (13)
C3—C2—C7—O1	179.16 (12)	C11—C10—C15—C14	−0.9 (2)
C1—C2—C7—O1	−0.07 (15)	S1—C10—C15—C14	177.93 (10)
C3—C2—C7—C6	−1.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 3-methylphenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.51	3.450 (2)	172
C6—H6···Cg3ⁱⁱ	0.95	2.76	3.556 (2)	142

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

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 3-methylphenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.51	3.450 (2)	172.3
C6—H6···Cg3ⁱⁱ	0.95	2.76	3.556 (2)	141.8

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

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, o455. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o258. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1909. Web of Science 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 70| Part 4| April 2014| Page o482

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