2-Methyl-5,6-methyl­enedi­oxy-3-phenyl­sulfonyl-1-benzofuran

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

doi:10.1107/S160053680800980X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o849

doi:10.1107/S160053680800980X

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2-Methyl-5,6-methylenedioxy-3-phenylsulfonyl-1-benzofuran

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 18 March 2008; accepted 10 April 2008; online 16 April 2008)

The title compound, C₁₆H₁₂O₅S, was prepared by oxidation of 2-methyl-5,6-methylenedioxy-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 83.64 (4)° with the mean plane of the 5,6-(methylenedioxy)benzofuran fragment. The crystal structure is stabilized by C—H⋯π interactions between a benzene H atom of the 5,6-(methylenedioxy)benzofuran unit and the phenyl ring of the phenylsulfonyl substituent. Additionally, the crystal structure exhibits inter- and intramolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 5,6-(methylenedioxy)benzofuran compounds, see: Choi et al. (2007a ,b ).

Experimental

Crystal data

C₁₆H₁₂O₅S
M_r = 316.32
Triclinic, $[P \overline 1]$
a = 7.4401 (3) Å
b = 8.8505 (4) Å
c = 11.2406 (5) Å
α = 89.801 (1)°
β = 72.565 (1)°
γ = 79.257 (1)°
V = 692.71 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 173 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
6000 measured reflections
2983 independent reflections
2746 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.05
2983 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgⁱ	0.95	2.83	3.722 (3)	152
C3—H3⋯O4ⁱⁱ	0.95	2.53	3.379 (2)	150
C12—H12⋯O2ⁱⁱⁱ	0.95	2.53	3.398 (2)	153
C16—H16C⋯O5	0.98	2.42	3.127 (3)	129
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1.

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/S160053680800980X/bh2167sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800980X/bh2167Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies on the synthesis and structure of 5,6-(methylenedioxy)benzofuran derivatives, the crystal structures of 5,6-methylenedioxy-3-methylsulfinyl-2-phenylbenzofuran (Choi et al., 2007a) and 2-methyl-5,6-methylenedioxy-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b) have been described to the literatures. Herein we report the molecular and crystal structure of the title compound, 2-methyl-5,6-methylenedioxy-3-phenylsulfonyl-1-benzofuran (Fig. 1).

The 5,6-(methylenedioxy)benzofuran unit is almost planar, with a mean deviation of 0.032 Å from the least-squares plane defined by the twelve constituent atoms. The crystal packing (Fig. 2) is stabilized by C—H···π interactions between a benzene H atom of 5,6-(methylenedioxy)benzofuran unit and the phenyl ring of the phenylsulfonyl substituent, with a C6—H6···Cgⁱ separation of 2.83 Å (Fig. 2 and Table 1; Cg is the centroid of the C9–C14 benzene ring, symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by intermolecular and intramolecular C—H···O interactions (Table 1 and Fig.2; symmetry codes as in Fig. 2).

Related literature top

For the crystal structures of similar 5,6-(methylenedioxy)benzofuran compounds, see: Choi et al. (2007a,b).

Experimental top

3-Chloroperoxybenzoic acid (77%, 560 mg, 2.50 mmol) was added in small portions to a stirred solution of 2-methyl-5,6-methylenedioxy-3-phenyl-sulfonyl-1-benzofuran (341 mg, 1.20 mmol) in dichloromethane (30 ml) at room temperature. After being stirred for 4 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 (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 442–443 K; R_f = 0.54 (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 acetone at room temperature.

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 50% probability level.
	Fig. 2. C—H···π and intra- and intermolecular C—H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (i) -x, -y + 2, -z + 1; (ii) -x + 1, -y + 1, -z + 1; iii) -x, -y + 1, -z + 1.]

2-Methyl-5,6-methylenedioxy-3-phenylsulfonyl-1-benzofuran top

Crystal data top

C₁₆H₁₂O₅S	Z = 2
M_r = 316.32	F(000) = 328
Triclinic, P1	D_x = 1.517 Mg m⁻³
Hall symbol: -P 1	Melting point = 442–443 K
a = 7.4401 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8505 (4) Å	Cell parameters from 4646 reflections
c = 11.2406 (5) Å	θ = 2.4–28.2°
α = 89.801 (1)°	µ = 0.26 mm⁻¹
β = 72.565 (1)°	T = 173 K
γ = 79.257 (1)°	Block, colourless
V = 692.71 (5) Å³	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2746 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 27.0°, θ_min = 2.9°
Detector resolution: 10.0 pixels mm^-1	h = −9→9
ϕ and ω scans	k = −11→11
6000 measured reflections	l = −14→13
2983 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0449P)² + 0.3658P] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₁₂O₅S	γ = 79.257 (1)°
M_r = 316.32	V = 692.71 (5) Å³
Triclinic, P1	Z = 2
a = 7.4401 (3) Å	Mo Kα radiation
b = 8.8505 (4) Å	µ = 0.26 mm⁻¹
c = 11.2406 (5) Å	T = 173 K
α = 89.801 (1)°	0.40 × 0.20 × 0.20 mm
β = 72.565 (1)°

Data collection top

Bruker SMART CCD diffractometer	2746 reflections with I > 2σ(I)
6000 measured reflections	R_int = 0.026
2983 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
2983 reflections	Δρ_min = −0.38 e Å⁻³
200 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S	0.36347 (5)	0.72181 (4)	0.70730 (3)	0.02587 (12)
O1	0.16796 (16)	1.11741 (12)	0.58768 (11)	0.0317 (3)
O2	0.46615 (19)	0.74239 (14)	0.16742 (10)	0.0364 (3)
O3	0.3156 (2)	0.98837 (15)	0.14228 (11)	0.0399 (3)
O4	0.52005 (16)	0.61904 (13)	0.62032 (10)	0.0313 (3)
O5	0.38566 (18)	0.77361 (16)	0.82216 (11)	0.0388 (3)
C1	0.2989 (2)	0.88120 (17)	0.62765 (14)	0.0250 (3)
C2	0.3186 (2)	0.88013 (17)	0.49576 (14)	0.0236 (3)
C3	0.4015 (2)	0.76992 (17)	0.39479 (13)	0.0249 (3)
H3	0.4609	0.6676	0.4039	0.030*
C4	0.3893 (2)	0.82284 (18)	0.28230 (14)	0.0266 (3)
C5	0.3014 (2)	0.97239 (19)	0.26672 (15)	0.0290 (3)
C6	0.2216 (2)	1.08254 (18)	0.36244 (16)	0.0311 (3)
H6	0.1631	1.1847	0.3521	0.037*
C7	0.2350 (2)	1.02901 (17)	0.47682 (15)	0.0263 (3)
C8	0.2083 (2)	1.02469 (19)	0.67807 (15)	0.0299 (3)
C9	0.1598 (2)	0.63445 (17)	0.74530 (14)	0.0259 (3)
C10	0.1304 (2)	0.54383 (18)	0.65468 (16)	0.0311 (3)
H10	0.2229	0.5230	0.5745	0.037*
C11	−0.0363 (3)	0.4846 (2)	0.6836 (2)	0.0397 (4)
H11	−0.0595	0.4236	0.6225	0.048*
C12	−0.1687 (3)	0.5136 (2)	0.8009 (2)	0.0443 (5)
H12	−0.2836	0.4739	0.8194	0.053*
C13	−0.1355 (3)	0.6000 (2)	0.89174 (19)	0.0455 (5)
H13	−0.2253	0.6162	0.9731	0.055*
C14	0.0288 (3)	0.6630 (2)	0.86401 (16)	0.0366 (4)
H14	0.0512	0.7245	0.9252	0.044*
C15	0.4011 (3)	0.8388 (2)	0.08173 (17)	0.0467 (5)
H15A	0.3056	0.7952	0.0546	0.056*
H15B	0.5103	0.8463	0.0071	0.056*
C16	0.1447 (3)	1.0983 (2)	0.80603 (17)	0.0421 (4)
H16A	0.0064	1.1036	0.8430	0.063*
H16B	0.1720	1.2027	0.8021	0.063*
H16C	0.2137	1.0374	0.8574	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0256 (2)	0.0340 (2)	0.01994 (19)	−0.00685 (15)	−0.00916 (14)	0.00132 (14)
O1	0.0297 (6)	0.0249 (5)	0.0371 (6)	−0.0040 (4)	−0.0060 (5)	−0.0037 (5)
O2	0.0539 (8)	0.0377 (6)	0.0213 (5)	−0.0141 (6)	−0.0137 (5)	0.0014 (5)
O3	0.0539 (8)	0.0439 (7)	0.0329 (6)	−0.0191 (6)	−0.0238 (6)	0.0157 (5)
O4	0.0265 (6)	0.0366 (6)	0.0286 (6)	−0.0008 (5)	−0.0082 (4)	0.0029 (5)
O5	0.0428 (7)	0.0556 (8)	0.0249 (6)	−0.0163 (6)	−0.0164 (5)	0.0010 (5)
C1	0.0237 (7)	0.0285 (7)	0.0236 (7)	−0.0070 (6)	−0.0071 (5)	−0.0009 (6)
C2	0.0223 (7)	0.0257 (7)	0.0243 (7)	−0.0070 (5)	−0.0080 (5)	0.0024 (5)
C3	0.0284 (7)	0.0238 (7)	0.0236 (7)	−0.0054 (6)	−0.0091 (6)	0.0014 (6)
C4	0.0299 (7)	0.0295 (8)	0.0236 (7)	−0.0124 (6)	−0.0090 (6)	0.0024 (6)
C5	0.0296 (8)	0.0355 (8)	0.0291 (8)	−0.0148 (6)	−0.0145 (6)	0.0115 (6)
C6	0.0284 (8)	0.0262 (7)	0.0418 (9)	−0.0072 (6)	−0.0142 (7)	0.0107 (7)
C7	0.0226 (7)	0.0244 (7)	0.0319 (8)	−0.0065 (5)	−0.0069 (6)	−0.0002 (6)
C8	0.0252 (7)	0.0329 (8)	0.0304 (8)	−0.0093 (6)	−0.0044 (6)	−0.0045 (6)
C9	0.0254 (7)	0.0273 (7)	0.0257 (7)	−0.0053 (6)	−0.0089 (6)	0.0048 (6)
C10	0.0328 (8)	0.0276 (8)	0.0336 (8)	−0.0028 (6)	−0.0131 (7)	0.0014 (6)
C11	0.0406 (9)	0.0276 (8)	0.0580 (11)	−0.0083 (7)	−0.0244 (9)	0.0041 (8)
C12	0.0325 (9)	0.0333 (9)	0.0694 (13)	−0.0113 (7)	−0.0160 (9)	0.0172 (9)
C13	0.0332 (9)	0.0470 (11)	0.0467 (11)	−0.0073 (8)	0.0017 (8)	0.0132 (8)
C14	0.0366 (9)	0.0406 (9)	0.0290 (8)	−0.0078 (7)	−0.0045 (7)	0.0023 (7)
C15	0.0520 (11)	0.0598 (12)	0.0258 (9)	−0.0075 (9)	−0.0105 (8)	0.0105 (8)
C16	0.0381 (9)	0.0464 (10)	0.0364 (9)	−0.0107 (8)	−0.0017 (7)	−0.0164 (8)

Geometric parameters (Å, º) top

S—O5	1.4369 (12)	C6—H6	0.9500
S—O4	1.4384 (12)	C8—C16	1.484 (2)
S—C1	1.7374 (16)	C9—C14	1.388 (2)
S—C9	1.7674 (15)	C9—C10	1.390 (2)
O1—C8	1.371 (2)	C10—C11	1.385 (2)
O1—C7	1.3794 (18)	C10—H10	0.9500
O2—C4	1.3833 (18)	C11—C12	1.380 (3)
O2—C15	1.418 (2)	C11—H11	0.9500
O3—C5	1.3797 (19)	C12—C13	1.384 (3)
O3—C15	1.433 (2)	C12—H12	0.9500
C1—C8	1.358 (2)	C13—C14	1.388 (3)
C1—C2	1.445 (2)	C13—H13	0.9500
C2—C7	1.393 (2)	C14—H14	0.9500
C2—C3	1.409 (2)	C15—H15A	0.9900
C3—C4	1.369 (2)	C15—H15B	0.9900
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.398 (2)	C16—H16B	0.9800
C5—C6	1.367 (2)	C16—H16C	0.9800
C6—C7	1.394 (2)

O5—S—O4	119.53 (7)	O1—C8—C16	115.53 (15)
O5—S—C1	108.96 (8)	C14—C9—C10	121.50 (15)
O4—S—C1	107.55 (7)	C14—C9—S	118.94 (13)
O5—S—C9	107.76 (7)	C10—C9—S	119.51 (12)
O4—S—C9	108.26 (7)	C11—C10—C9	118.71 (16)
C1—S—C9	103.65 (7)	C11—C10—H10	120.6
C8—O1—C7	107.02 (12)	C9—C10—H10	120.6
C4—O2—C15	105.85 (13)	C12—C11—C10	120.33 (17)
C5—O3—C15	105.87 (13)	C12—C11—H11	119.8
C8—C1—C2	107.71 (14)	C10—C11—H11	119.8
C8—C1—S	126.84 (12)	C11—C12—C13	120.56 (17)
C2—C1—S	125.26 (11)	C11—C12—H12	119.7
C7—C2—C3	120.48 (14)	C13—C12—H12	119.7
C7—C2—C1	104.66 (13)	C12—C13—C14	120.04 (18)
C3—C2—C1	134.85 (14)	C12—C13—H13	120.0
C4—C3—C2	114.24 (14)	C14—C13—H13	120.0
C4—C3—H3	122.9	C9—C14—C13	118.81 (17)
C2—C3—H3	122.9	C9—C14—H14	120.6
C3—C4—O2	126.58 (14)	C13—C14—H14	120.6
C3—C4—C5	123.90 (14)	O2—C15—O3	108.47 (14)
O2—C4—C5	109.48 (13)	O2—C15—H15A	110.0
C6—C5—O3	127.47 (15)	O3—C15—H15A	110.0
C6—C5—C4	123.31 (14)	O2—C15—H15B	110.0
O3—C5—C4	109.19 (14)	O3—C15—H15B	110.0
C5—C6—C7	112.80 (14)	H15A—C15—H15B	108.4
C5—C6—H6	123.6	C8—C16—H16A	109.5
C7—C6—H6	123.6	C8—C16—H16B	109.5
O1—C7—C2	110.33 (13)	H16A—C16—H16B	109.5
O1—C7—C6	124.42 (14)	C8—C16—H16C	109.5
C2—C7—C6	125.25 (15)	H16A—C16—H16C	109.5
C1—C8—O1	110.29 (14)	H16B—C16—H16C	109.5
C1—C8—C16	134.18 (17)

O5—S—C1—C8	−25.07 (16)	C1—C2—C7—O1	0.06 (16)
O4—S—C1—C8	−156.01 (14)	C3—C2—C7—C6	1.1 (2)
C9—S—C1—C8	89.47 (15)	C1—C2—C7—C6	179.64 (14)
O5—S—C1—C2	160.50 (12)	C5—C6—C7—O1	179.15 (13)
O4—S—C1—C2	29.55 (15)	C5—C6—C7—C2	−0.4 (2)
C9—S—C1—C2	−84.96 (14)	C2—C1—C8—O1	−0.16 (17)
C8—C1—C2—C7	0.06 (16)	S—C1—C8—O1	−175.39 (11)
S—C1—C2—C7	175.39 (11)	C2—C1—C8—C16	179.14 (17)
C8—C1—C2—C3	178.25 (16)	S—C1—C8—C16	3.9 (3)
S—C1—C2—C3	−6.4 (3)	C7—O1—C8—C1	0.19 (17)
C7—C2—C3—C4	−0.6 (2)	C7—O1—C8—C16	−179.25 (13)
C1—C2—C3—C4	−178.60 (15)	O5—S—C9—C14	17.03 (15)
C2—C3—C4—O2	176.68 (14)	O4—S—C9—C14	147.62 (13)
C2—C3—C4—C5	−0.5 (2)	C1—S—C9—C14	−98.37 (14)
C15—O2—C4—C3	174.65 (16)	O5—S—C9—C10	−165.42 (12)
C15—O2—C4—C5	−7.83 (18)	O4—S—C9—C10	−34.83 (14)
C15—O3—C5—C6	−177.05 (17)	C1—S—C9—C10	79.18 (13)
C15—O3—C5—C4	4.93 (18)	C14—C9—C10—C11	1.7 (2)
C3—C4—C5—C6	1.3 (2)	S—C9—C10—C11	−175.83 (12)
O2—C4—C5—C6	−176.29 (14)	C9—C10—C11—C12	−0.9 (2)
C3—C4—C5—O3	179.42 (14)	C10—C11—C12—C13	−1.1 (3)
O2—C4—C5—O3	1.82 (17)	C11—C12—C13—C14	2.3 (3)
O3—C5—C6—C7	−178.56 (14)	C10—C9—C14—C13	−0.5 (3)
C4—C5—C6—C7	−0.8 (2)	S—C9—C14—C13	177.04 (14)
C8—O1—C7—C2	−0.15 (16)	C12—C13—C14—C9	−1.5 (3)
C8—O1—C7—C6	−179.74 (14)	C4—O2—C15—O3	10.86 (19)
C3—C2—C7—O1	−178.45 (12)	C5—O3—C15—O2	−9.81 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgⁱ	0.95	2.83	3.722 (3)	152
C3—H3···O4ⁱⁱ	0.95	2.53	3.379 (2)	150
C12—H12···O2ⁱⁱⁱ	0.95	2.53	3.398 (2)	153
C16—H16C···O5	0.98	2.42	3.127 (3)	129

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₅S
M_r	316.32
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.4401 (3), 8.8505 (4), 11.2406 (5)
α, β, γ (°)	89.801 (1), 72.565 (1), 79.257 (1)
V (Å³)	692.71 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6000, 2983, 2746
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.05
No. of reflections	2983
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.38

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C6—H6···Cgⁱ	0.95	2.83	3.722 (3)	152.2
C3—H3···O4ⁱⁱ	0.95	2.53	3.379 (2)	149.5
C12—H12···O2ⁱⁱⁱ	0.95	2.53	3.398 (2)	152.8
C16—H16C···O5	0.98	2.42	3.127 (3)	129.0

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

References

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., Lee, H. K., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o519–o520. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Lee, J. B., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o2050–o2051. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef 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 64| Part 5| May 2008| Page o849

doi:10.1107/S160053680800980X

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