2-(4-Fluoro­phen­yl)-5,6-methyl­enedi­oxy-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536810004745

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o605

doi:10.1107/S1600536810004745

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2-(4-Fluorophenyl)-5,6-methylenedioxy-3-methylsulfinyl-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 5 January 2010; accepted 6 February 2010; online 13 February 2010)

In the title compound, C₁₆H₁₁FO₄S, the O atom and the methyl group of the methylsulfinyl substituent are located on opposite sides of the mean plane through the 5,6-(methylenedioxy)benzofuran fragment. The 4-fluorophenyl ring is rotated out of the 5,6-(methylenedioxy)benzofuran plane, making a dihedral angle of 29.90 (6)°. In the crystal structure, both intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The combination of C—H⋯O hydrogen bonds result in chains running along [1 $[\overline{1}]$ $[\overline{1}]$ ].

Related literature

For the structures of similar 5,6-methylenedioxy-1-benzofuran derivatives, see: Choi et al. (2007 , 2009 ). For the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999 ); Twyman & Allsop (1999 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); von Reuss & König (2004 ).

Experimental

Crystal data

C₁₆H₁₁FO₄S
M_r = 318.31
Triclinic, $[P \overline 1]$
a = 8.0283 (7) Å
b = 8.4072 (7) Å
c = 10.6611 (9) Å
α = 85.735 (1)°
β = 86.319 (1)°
γ = 68.110 (1)°
V = 665.33 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.899, T_max = 0.948
4954 measured reflections
2325 independent reflections
2153 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.04
2325 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.54	3.383 (2)	151
C14—H14⋯O4ⁱⁱ	0.93	2.57	3.368 (2)	144
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+2, -y, -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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810004745/kj2140sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004745/kj2140Isup2.hkl

checkCIF report

Comment top

Benzofuran ring systems have received considerable attention in view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999) and their occurrence as natural products (Akgul & Anil, 2003; von Reuss & König, 2004). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 5,6-methylenedioxy-1-benzofuran analogues (Choi et al., 2007,2009), we report the crystal structure of the title compound (Fig.1).

The 5,6-(methylenedioxy)benzofuran unit is essentially planar, with a mean deviation of 0.060 (2) Å from the least-squares plane defined by the twelve constituent atoms. The dihedral angle formed by the plane of the 5,6-(methylenedioxy)benzofuran ring and the plane of 4-fluorophenyl ring is 29.90 (6).

In the crystal packing, both intermolecular C—H···O hydrogen bonds (C3—H3···O2 and C14—H14···O4) link the molecules into dimers (Table 1, Figure 2). Together, the C—H···O hydrogen-bond interactions link the molecules into a one-dimensional chain running in the [1,-1,-1] direction.

Related literature top

For the structures of similar 5,6-methylenedioxy-1-benzofuran derivatives, see: Choi et al. (2007, 2009). For the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For natural products with benzofuran rings, see: Akgul & Anil (2003); von Reuss & König (2004).

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5,6-methylenedioxy-3-methylsulfanyl-1-benzofuran (302 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 2h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 488–489 K; R_f = 0.51 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroform 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.
	Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 1, - z + 2; (ii) - x + 2, - y, - z + 1.]

2-(4-Fluorophenyl)-5,6-methylenedioxy-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₆H₁₁FO₄S	Z = 2
M_r = 318.31	F(000) = 328
Triclinic, P1	D_x = 1.589 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0283 (7) Å	Cell parameters from 4336 reflections
b = 8.4072 (7) Å	θ = 2.6–27.4°
c = 10.6611 (9) Å	µ = 0.27 mm⁻¹
α = 85.735 (1)°	T = 173 K
β = 86.319 (1)°	Block, colourless
γ = 68.110 (1)°	0.40 × 0.40 × 0.20 mm
V = 665.33 (10) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	2325 independent reflections
Radiation source: Rotating Anode	2153 reflections with I > 2σ(I)
HELIOS monochromator	R_int = 0.036
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→9
T_min = 0.899, T_max = 0.948	l = −12→12
4954 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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0477P)² + 0.4337P] where P = (F_o² + 2F_c²)/3
2325 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₁₁FO₄S	γ = 68.110 (1)°
M_r = 318.31	V = 665.33 (10) Å³
Triclinic, P1	Z = 2
a = 8.0283 (7) Å	Mo Kα radiation
b = 8.4072 (7) Å	µ = 0.27 mm⁻¹
c = 10.6611 (9) Å	T = 173 K
α = 85.735 (1)°	0.40 × 0.40 × 0.20 mm
β = 86.319 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2325 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2153 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.948	R_int = 0.036
4954 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.76 e Å⁻³
2325 reflections	Δρ_min = −0.34 e Å⁻³
200 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
S	0.80463 (5)	0.18763 (6)	0.60869 (4)	0.02335 (16)
F	0.68941 (16)	−0.01363 (16)	0.02490 (11)	0.0385 (3)
O1	0.29585 (16)	0.35961 (16)	0.51174 (11)	0.0228 (3)
O2	0.25335 (17)	0.57506 (17)	0.98364 (12)	0.0292 (3)
O3	−0.01602 (17)	0.65674 (17)	0.88470 (12)	0.0285 (3)
O4	0.84924 (18)	0.30301 (18)	0.68884 (15)	0.0372 (4)
C1	0.5684 (2)	0.2707 (2)	0.59585 (16)	0.0206 (4)
C2	0.4380 (2)	0.3671 (2)	0.68856 (16)	0.0204 (4)
C3	0.4467 (2)	0.4134 (2)	0.81182 (16)	0.0225 (4)
H3	0.5537	0.3792	0.8537	0.027*
C4	0.2853 (2)	0.5124 (2)	0.86443 (16)	0.0229 (4)
C5	0.0711 (3)	0.6920 (2)	0.98677 (18)	0.0289 (4)
H5A	0.0661	0.8093	0.9776	0.035*
H5B	0.0117	0.6769	1.0664	0.035*
C6	0.1218 (2)	0.5638 (2)	0.80438 (17)	0.0222 (4)
C7	0.1075 (2)	0.5200 (2)	0.68512 (17)	0.0237 (4)
H7	−0.0006	0.5531	0.6449	0.028*
C8	0.2736 (2)	0.4202 (2)	0.63084 (16)	0.0209 (4)
C9	0.4775 (2)	0.2695 (2)	0.49235 (16)	0.0214 (4)
C10	0.5313 (2)	0.1926 (2)	0.37027 (16)	0.0214 (4)
C11	0.4330 (2)	0.2717 (2)	0.26424 (16)	0.0227 (4)
H11	0.3323	0.3721	0.2719	0.027*
C12	0.4845 (2)	0.2015 (2)	0.14773 (17)	0.0251 (4)
H12	0.4192	0.2530	0.0769	0.030*
C13	0.6347 (2)	0.0537 (2)	0.13962 (17)	0.0259 (4)
C14	0.7337 (2)	−0.0306 (2)	0.24219 (17)	0.0272 (4)
H14	0.8334	−0.1315	0.2336	0.033*
C15	0.6797 (2)	0.0397 (2)	0.35841 (17)	0.0258 (4)
H15	0.7430	−0.0156	0.4292	0.031*
C16	0.8251 (3)	−0.0009 (3)	0.70708 (19)	0.0321 (4)
H16A	0.9492	−0.0629	0.7248	0.048*
H16B	0.7803	−0.0726	0.6646	0.048*
H16C	0.7568	0.0320	0.7845	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0165 (2)	0.0224 (3)	0.0292 (3)	−0.00522 (18)	−0.00198 (17)	0.00089 (18)
F	0.0361 (7)	0.0477 (7)	0.0256 (6)	−0.0067 (6)	0.0027 (5)	−0.0155 (5)
O1	0.0185 (6)	0.0260 (7)	0.0216 (6)	−0.0047 (5)	−0.0023 (5)	−0.0047 (5)
O2	0.0273 (7)	0.0341 (7)	0.0212 (6)	−0.0043 (6)	−0.0010 (5)	−0.0076 (5)
O3	0.0223 (7)	0.0311 (7)	0.0269 (7)	−0.0034 (5)	0.0030 (5)	−0.0071 (5)
O4	0.0264 (7)	0.0293 (8)	0.0570 (10)	−0.0088 (6)	−0.0137 (6)	−0.0068 (7)
C1	0.0175 (8)	0.0201 (8)	0.0224 (9)	−0.0050 (7)	−0.0004 (7)	−0.0011 (7)
C2	0.0193 (8)	0.0197 (8)	0.0217 (8)	−0.0065 (7)	−0.0012 (7)	−0.0004 (7)
C3	0.0210 (9)	0.0248 (9)	0.0218 (9)	−0.0082 (7)	−0.0034 (7)	−0.0004 (7)
C4	0.0262 (9)	0.0227 (9)	0.0194 (8)	−0.0083 (7)	−0.0011 (7)	−0.0018 (7)
C5	0.0283 (10)	0.0282 (10)	0.0266 (9)	−0.0056 (8)	0.0026 (8)	−0.0080 (8)
C6	0.0196 (9)	0.0194 (9)	0.0255 (9)	−0.0052 (7)	0.0020 (7)	−0.0009 (7)
C7	0.0175 (8)	0.0243 (9)	0.0271 (9)	−0.0050 (7)	−0.0030 (7)	−0.0013 (7)
C8	0.0217 (9)	0.0210 (9)	0.0197 (8)	−0.0072 (7)	−0.0015 (7)	−0.0026 (7)
C9	0.0176 (8)	0.0207 (9)	0.0236 (9)	−0.0044 (7)	−0.0003 (7)	−0.0010 (7)
C10	0.0212 (9)	0.0222 (9)	0.0219 (9)	−0.0093 (7)	0.0003 (7)	−0.0031 (7)
C11	0.0204 (9)	0.0211 (9)	0.0259 (9)	−0.0069 (7)	−0.0010 (7)	−0.0018 (7)
C12	0.0261 (9)	0.0283 (10)	0.0219 (9)	−0.0109 (8)	−0.0034 (7)	0.0000 (7)
C13	0.0274 (10)	0.0310 (10)	0.0218 (9)	−0.0130 (8)	0.0028 (7)	−0.0089 (7)
C14	0.0228 (9)	0.0252 (10)	0.0303 (10)	−0.0038 (7)	−0.0005 (7)	−0.0076 (8)
C15	0.0249 (9)	0.0254 (9)	0.0249 (9)	−0.0061 (8)	−0.0051 (7)	−0.0009 (7)
C16	0.0292 (10)	0.0277 (10)	0.0383 (11)	−0.0100 (8)	−0.0077 (8)	0.0079 (8)

Geometric parameters (Å, º) top

S—O4	1.4903 (14)	C5—H5B	0.9700
S—C1	1.7707 (17)	C6—C7	1.373 (3)
S—C16	1.7944 (19)	C7—C8	1.398 (2)
F—C13	1.363 (2)	C7—H7	0.9300
O1—C8	1.380 (2)	C9—C10	1.464 (2)
O1—C9	1.380 (2)	C10—C15	1.397 (3)
O2—C4	1.384 (2)	C10—C11	1.398 (2)
O2—C5	1.426 (2)	C11—C12	1.387 (3)
O3—C6	1.379 (2)	C11—H11	0.9300
O3—C5	1.436 (2)	C12—C13	1.375 (3)
C1—C9	1.364 (2)	C12—H12	0.9300
C1—C2	1.443 (2)	C13—C14	1.380 (3)
C2—C8	1.395 (2)	C14—C15	1.386 (3)
C2—C3	1.411 (2)	C14—H14	0.9300
C3—C4	1.363 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C6	1.401 (3)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600

O4—S—C1	107.29 (8)	O1—C8—C2	110.69 (15)
O4—S—C16	105.76 (9)	O1—C8—C7	123.97 (15)
C1—S—C16	98.28 (9)	C2—C8—C7	125.34 (16)
C8—O1—C9	106.48 (13)	C1—C9—O1	110.48 (15)
C4—O2—C5	105.53 (13)	C1—C9—C10	133.97 (16)
C6—O3—C5	105.04 (14)	O1—C9—C10	115.53 (14)
C9—C1—C2	107.49 (15)	C15—C10—C11	119.35 (16)
C9—C1—S	126.25 (13)	C15—C10—C9	120.68 (16)
C2—C1—S	126.00 (13)	C11—C10—C9	119.97 (16)
C8—C2—C3	120.39 (16)	C12—C11—C10	120.44 (16)
C8—C2—C1	104.84 (15)	C12—C11—H11	119.8
C3—C2—C1	134.76 (16)	C10—C11—H11	119.8
C4—C3—C2	114.39 (16)	C13—C12—C11	118.26 (16)
C4—C3—H3	122.8	C13—C12—H12	120.9
C2—C3—H3	122.8	C11—C12—H12	120.9
C3—C4—O2	126.99 (16)	F—C13—C12	118.70 (16)
C3—C4—C6	124.06 (16)	F—C13—C14	118.04 (16)
O2—C4—C6	108.93 (15)	C12—C13—C14	123.25 (17)
O2—C5—O3	107.68 (14)	C13—C14—C15	117.97 (17)
O2—C5—H5A	110.2	C13—C14—H14	121.0
O3—C5—H5A	110.2	C15—C14—H14	121.0
O2—C5—H5B	110.2	C14—C15—C10	120.68 (17)
O3—C5—H5B	110.2	C14—C15—H15	119.7
H5A—C5—H5B	108.5	C10—C15—H15	119.7
C7—C6—O3	127.18 (16)	S—C16—H16A	109.5
C7—C6—C4	123.29 (16)	S—C16—H16B	109.5
O3—C6—C4	109.50 (15)	H16A—C16—H16B	109.5
C6—C7—C8	112.52 (16)	S—C16—H16C	109.5
C6—C7—H7	123.7	H16A—C16—H16C	109.5
C8—C7—H7	123.7	H16B—C16—H16C	109.5

O4—S—C1—C9	144.09 (16)	C3—C2—C8—O1	−179.45 (15)
C16—S—C1—C9	−106.47 (17)	C1—C2—C8—O1	1.26 (19)
O4—S—C1—C2	−29.26 (18)	C3—C2—C8—C7	0.1 (3)
C16—S—C1—C2	80.17 (17)	C1—C2—C8—C7	−179.22 (17)
C9—C1—C2—C8	−0.86 (19)	C6—C7—C8—O1	179.98 (16)
S—C1—C2—C8	173.53 (13)	C6—C7—C8—C2	0.5 (3)
C9—C1—C2—C3	−179.99 (19)	C2—C1—C9—O1	0.2 (2)
S—C1—C2—C3	−5.6 (3)	S—C1—C9—O1	−174.20 (12)
C8—C2—C3—C4	−0.8 (2)	C2—C1—C9—C10	−178.74 (18)
C1—C2—C3—C4	178.23 (18)	S—C1—C9—C10	6.9 (3)
C2—C3—C4—O2	179.41 (16)	C8—O1—C9—C1	0.61 (19)
C2—C3—C4—C6	1.0 (3)	C8—O1—C9—C10	179.74 (14)
C5—O2—C4—C3	171.11 (18)	C1—C9—C10—C15	30.2 (3)
C5—O2—C4—C6	−10.26 (19)	O1—C9—C10—C15	−148.66 (16)
C4—O2—C5—O3	17.49 (19)	C1—C9—C10—C11	−150.3 (2)
C6—O3—C5—O2	−18.03 (19)	O1—C9—C10—C11	30.9 (2)
C5—O3—C6—C7	−170.31 (18)	C15—C10—C11—C12	−1.5 (3)
C5—O3—C6—C4	11.72 (19)	C9—C10—C11—C12	178.93 (16)
C3—C4—C6—C7	−0.4 (3)	C10—C11—C12—C13	−0.5 (3)
O2—C4—C6—C7	−179.07 (16)	C11—C12—C13—F	−178.17 (16)
C3—C4—C6—O3	177.68 (16)	C11—C12—C13—C14	1.8 (3)
O2—C4—C6—O3	−1.0 (2)	F—C13—C14—C15	178.87 (17)
O3—C6—C7—C8	−178.09 (16)	C12—C13—C14—C15	−1.1 (3)
C4—C6—C7—C8	−0.4 (3)	C13—C14—C15—C10	−1.0 (3)
C9—O1—C8—C2	−1.19 (19)	C11—C10—C15—C14	2.3 (3)
C9—O1—C8—C7	179.28 (16)	C9—C10—C15—C14	−178.20 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.54	3.383 (2)	151
C14—H14···O4ⁱⁱ	0.93	2.57	3.368 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁FO₄S
M_r	318.31
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.0283 (7), 8.4072 (7), 10.6611 (9)
α, β, γ (°)	85.735 (1), 86.319 (1), 68.110 (1)
V (Å³)	665.33 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.899, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	4954, 2325, 2153
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.04
No. of reflections	2325
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.34

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
C3—H3···O2ⁱ	0.93	2.54	3.383 (2)	151.1
C14—H14···O4ⁱⁱ	0.93	2.57	3.368 (2)	144.1

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

References

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Volume 66| Part 3| March 2010| Page o605

doi:10.1107/S1600536810004745

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