5-Fluoro-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536810025468

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1909

https://doi.org/10.1107/S1600536810025468

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5-Fluoro-3-(4-fluorophenylsulfonyl)-2-methyl-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 28 June 2010; accepted 29 June 2010; online 3 July 2010)

In the title compound, C₁₅H₁₀F₂O₃S, the 4-fluorophenyl ring makes a dihedral angle of 73.20 (4)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.805 (3) Å]. The crystal structure also exhibits weak intermolecular C—H⋯O and C—H⋯F interactions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the structures of related 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ,b ,c ).

Experimental

Crystal data

C₁₅H₁₀F₂O₃S
M_r = 308.29
Triclinic, $[P \overline 1]$
a = 7.2799 (9) Å
b = 9.5161 (12) Å
c = 10.1052 (13) Å
α = 89.844 (2)°
β = 75.057 (2)°
γ = 74.558 (2)°
V = 650.32 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.674, T_max = 0.746
5657 measured reflections
2797 independent reflections
2404 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.10
2797 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.93	2.45	3.247 (2)	144
C14—H14⋯F2ⁱⁱ	0.93	2.53	3.441 (2)	168
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -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: https://doi.org/10.1107/S1600536810025468/zl2288sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025468/zl2288Isup2.hkl

checkCIF report

Comment top

Compounds containing a benzofuran skeleton show diverse pharmacological properties such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), and antimicrobial (Khan et al., 2005) activities. These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al., 2008a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 73.20 (4)°. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the furan and the benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱⁱ distance of 3.805 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively). The molecular packing (Fig. 2) is further stabilized by a weak intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit (C11—H11···O2ⁱ, see Table 1 for symmetry operator and numerical values). The crystal packing (Fig. 2) also exhibits C—H···F hydrogen bonds between the 4-fluorophenyl H atom and the fluorine of 4-fluorophenyl ring (C14—H14···F2ⁱⁱ, Table 1).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the structures of related 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-fluoro-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (221 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 (benzene) to afford the title compound as a colorless solid [yield 76%, m.p. 426–427 K; R_f = 0.49 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Structure description top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the structures of related 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b,c).

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 a small spheres of arbitrary radius.
	Fig. 2. π–π, C—H···O, and C—H···F interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denote the ring centroids. [Symmetry codes: (i) - x + 1, - y, - z + 1; (ii) - x, - y, - z; (iii) - x, - y + 1, -z + 1.]

5-Fluoro-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran top

Crystal data top

C₁₅H₁₀F₂O₃S	Z = 2
M_r = 308.29	F(000) = 316
Triclinic, P1	D_x = 1.574 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2799 (9) Å	Cell parameters from 3365 reflections
b = 9.5161 (12) Å	θ = 2.9–27.5°
c = 10.1052 (13) Å	µ = 0.28 mm⁻¹
α = 89.844 (2)°	T = 173 K
β = 75.057 (2)°	Block, colourless
γ = 74.558 (2)°	0.40 × 0.40 × 0.30 mm
V = 650.32 (14) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	2797 independent reflections
Radiation source: rotating anode	2404 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.017
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.674, T_max = 0.746	l = −12→12
5657 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.092	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0387P)² + 0.2972P] where P = (F_o² + 2F_c²)/3
2797 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₅H₁₀F₂O₃S	γ = 74.558 (2)°
M_r = 308.29	V = 650.32 (14) Å³
Triclinic, P1	Z = 2
a = 7.2799 (9) Å	Mo Kα radiation
b = 9.5161 (12) Å	µ = 0.28 mm⁻¹
c = 10.1052 (13) Å	T = 173 K
α = 89.844 (2)°	0.40 × 0.40 × 0.30 mm
β = 75.057 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2797 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2404 reflections with I > 2σ(I)
T_min = 0.674, T_max = 0.746	R_int = 0.017
5657 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.10	Δρ_max = 0.25 e Å⁻³
2797 reflections	Δρ_min = −0.39 e Å⁻³
191 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	0.53634 (6)	0.20772 (5)	0.28012 (4)	0.02732 (13)
F1	0.23174 (19)	0.31294 (13)	0.87101 (11)	0.0452 (3)
F2	−0.00277 (18)	−0.11034 (13)	0.17822 (13)	0.0504 (3)
O1	0.20792 (17)	0.60640 (12)	0.41364 (12)	0.0278 (3)
O2	0.63798 (19)	0.12784 (14)	0.37331 (13)	0.0368 (3)
O3	0.64674 (18)	0.23753 (14)	0.14903 (13)	0.0370 (3)
C1	0.3867 (2)	0.37201 (17)	0.36913 (16)	0.0241 (3)
C2	0.3083 (2)	0.39702 (17)	0.51670 (16)	0.0237 (3)
C3	0.3194 (3)	0.31470 (19)	0.63059 (17)	0.0282 (4)
H3	0.3883	0.2162	0.6217	0.034*
C4	0.2220 (3)	0.3886 (2)	0.75675 (17)	0.0313 (4)
C5	0.1178 (3)	0.5354 (2)	0.77703 (18)	0.0315 (4)
H5	0.0569	0.5787	0.8654	0.038*
C6	0.1057 (2)	0.61649 (19)	0.66459 (18)	0.0295 (4)
H6	0.0370	0.7151	0.6742	0.035*
C7	0.2007 (2)	0.54383 (17)	0.53726 (17)	0.0240 (3)
C8	0.3217 (2)	0.50019 (18)	0.31296 (17)	0.0262 (3)
C9	0.3471 (3)	0.5460 (2)	0.17131 (18)	0.0368 (4)
H9A	0.4197	0.4629	0.1077	0.055*
H9B	0.4185	0.6187	0.1588	0.055*
H9C	0.2197	0.5861	0.1552	0.055*
C10	0.3712 (2)	0.11336 (17)	0.25046 (17)	0.0255 (3)
C11	0.2913 (3)	0.03091 (18)	0.35213 (18)	0.0318 (4)
H11	0.3231	0.0266	0.4357	0.038*
C12	0.1637 (3)	−0.04468 (19)	0.3270 (2)	0.0365 (4)
H12	0.1094	−0.1012	0.3929	0.044*
C13	0.1192 (3)	−0.03435 (19)	0.2028 (2)	0.0353 (4)
C14	0.1938 (3)	0.0481 (2)	0.10132 (19)	0.0349 (4)
H14	0.1589	0.0535	0.0188	0.042*
C15	0.3225 (3)	0.12286 (19)	0.12576 (17)	0.0299 (4)
H15	0.3760	0.1791	0.0591	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0230 (2)	0.0282 (2)	0.0273 (2)	−0.00234 (16)	−0.00558 (16)	−0.00427 (16)
F1	0.0603 (8)	0.0539 (7)	0.0261 (5)	−0.0203 (6)	−0.0153 (5)	0.0133 (5)
F2	0.0482 (7)	0.0426 (7)	0.0666 (8)	−0.0219 (6)	−0.0165 (6)	−0.0066 (6)
O1	0.0291 (6)	0.0244 (6)	0.0282 (6)	−0.0056 (5)	−0.0066 (5)	0.0038 (5)
O2	0.0312 (7)	0.0346 (7)	0.0412 (7)	0.0030 (5)	−0.0159 (6)	−0.0035 (6)
O3	0.0317 (7)	0.0438 (8)	0.0311 (7)	−0.0125 (6)	0.0014 (5)	−0.0081 (6)
C1	0.0227 (8)	0.0255 (8)	0.0235 (8)	−0.0062 (6)	−0.0058 (6)	−0.0006 (6)
C2	0.0209 (7)	0.0253 (8)	0.0257 (8)	−0.0071 (6)	−0.0070 (6)	0.0002 (6)
C3	0.0299 (9)	0.0266 (8)	0.0287 (9)	−0.0060 (7)	−0.0107 (7)	0.0035 (7)
C4	0.0338 (9)	0.0404 (10)	0.0242 (8)	−0.0162 (8)	−0.0095 (7)	0.0077 (7)
C5	0.0289 (9)	0.0405 (10)	0.0240 (8)	−0.0122 (7)	−0.0020 (7)	−0.0047 (7)
C6	0.0245 (8)	0.0281 (9)	0.0328 (9)	−0.0057 (7)	−0.0037 (7)	−0.0049 (7)
C7	0.0217 (8)	0.0250 (8)	0.0260 (8)	−0.0078 (6)	−0.0061 (6)	0.0028 (6)
C8	0.0246 (8)	0.0291 (8)	0.0256 (8)	−0.0091 (6)	−0.0060 (6)	0.0017 (6)
C9	0.0422 (11)	0.0401 (10)	0.0287 (9)	−0.0124 (8)	−0.0097 (8)	0.0092 (8)
C10	0.0240 (8)	0.0216 (8)	0.0271 (8)	−0.0009 (6)	−0.0058 (6)	−0.0023 (6)
C11	0.0357 (9)	0.0254 (8)	0.0322 (9)	−0.0031 (7)	−0.0112 (8)	0.0030 (7)
C12	0.0412 (11)	0.0247 (9)	0.0415 (10)	−0.0093 (8)	−0.0072 (8)	0.0063 (7)
C13	0.0318 (9)	0.0254 (9)	0.0478 (11)	−0.0068 (7)	−0.0101 (8)	−0.0070 (8)
C14	0.0346 (10)	0.0381 (10)	0.0314 (9)	−0.0072 (8)	−0.0106 (8)	−0.0053 (8)
C15	0.0302 (9)	0.0302 (9)	0.0259 (8)	−0.0055 (7)	−0.0045 (7)	−0.0008 (7)

Geometric parameters (Å, º) top

S—O3	1.4323 (13)	C6—C7	1.380 (2)
S—O2	1.4381 (13)	C6—H6	0.9300
S—C1	1.7422 (16)	C8—C9	1.475 (2)
S—C10	1.7618 (17)	C9—H9A	0.9600
F1—C4	1.3665 (19)	C9—H9B	0.9600
F2—C13	1.352 (2)	C9—H9C	0.9600
O1—C8	1.367 (2)	C10—C15	1.391 (2)
O1—C7	1.3771 (19)	C10—C11	1.393 (2)
C1—C8	1.364 (2)	C11—C12	1.387 (3)
C1—C2	1.448 (2)	C11—H11	0.9300
C2—C7	1.394 (2)	C12—C13	1.372 (3)
C2—C3	1.398 (2)	C12—H12	0.9300
C3—C4	1.377 (2)	C13—C14	1.378 (3)
C3—H3	0.9300	C14—C15	1.385 (2)
C4—C5	1.388 (3)	C14—H14	0.9300
C5—C6	1.380 (2)	C15—H15	0.9300
C5—H5	0.9300

O3—S—O2	119.98 (8)	C1—C8—O1	110.39 (14)
O3—S—C1	109.12 (8)	C1—C8—C9	134.23 (16)
O2—S—C1	106.45 (8)	O1—C8—C9	115.37 (15)
O3—S—C10	107.42 (8)	C8—C9—H9A	109.5
O2—S—C10	107.79 (8)	C8—C9—H9B	109.5
C1—S—C10	105.15 (7)	H9A—C9—H9B	109.5
C8—O1—C7	107.03 (12)	C8—C9—H9C	109.5
C8—C1—C2	107.54 (14)	H9A—C9—H9C	109.5
C8—C1—S	126.42 (13)	H9B—C9—H9C	109.5
C2—C1—S	126.04 (12)	C15—C10—C11	121.13 (16)
C7—C2—C3	119.16 (15)	C15—C10—S	119.32 (13)
C7—C2—C1	104.38 (14)	C11—C10—S	119.55 (13)
C3—C2—C1	136.45 (15)	C12—C11—C10	119.08 (17)
C4—C3—C2	115.79 (16)	C12—C11—H11	120.5
C4—C3—H3	122.1	C10—C11—H11	120.5
C2—C3—H3	122.1	C13—C12—C11	118.63 (17)
F1—C4—C3	117.75 (16)	C13—C12—H12	120.7
F1—C4—C5	117.29 (16)	C11—C12—H12	120.7
C3—C4—C5	124.94 (16)	F2—C13—C12	118.23 (17)
C6—C5—C4	119.29 (16)	F2—C13—C14	118.35 (17)
C6—C5—H5	120.4	C12—C13—C14	123.42 (17)
C4—C5—H5	120.4	C13—C14—C15	118.08 (17)
C7—C6—C5	116.58 (16)	C13—C14—H14	121.0
C7—C6—H6	121.7	C15—C14—H14	121.0
C5—C6—H6	121.7	C14—C15—C10	119.64 (17)
O1—C7—C6	125.09 (15)	C14—C15—H15	120.2
O1—C7—C2	110.65 (14)	C10—C15—H15	120.2
C6—C7—C2	124.23 (16)

O3—S—C1—C8	23.50 (17)	C1—C2—C7—C6	−177.47 (15)
O2—S—C1—C8	154.33 (15)	C2—C1—C8—O1	0.33 (18)
C10—S—C1—C8	−91.47 (16)	S—C1—C8—O1	−179.79 (11)
O3—S—C1—C2	−156.64 (14)	C2—C1—C8—C9	−179.30 (18)
O2—S—C1—C2	−25.81 (16)	S—C1—C8—C9	0.6 (3)
C10—S—C1—C2	88.39 (15)	C7—O1—C8—C1	0.06 (18)
C8—C1—C2—C7	−0.58 (18)	C7—O1—C8—C9	179.77 (14)
S—C1—C2—C7	179.54 (12)	O3—S—C10—C15	−20.43 (15)
C8—C1—C2—C3	−179.31 (18)	O2—S—C10—C15	−151.02 (13)
S—C1—C2—C3	0.8 (3)	C1—S—C10—C15	95.72 (14)
C7—C2—C3—C4	−0.7 (2)	O3—S—C10—C11	159.71 (13)
C1—C2—C3—C4	177.87 (17)	O2—S—C10—C11	29.12 (15)
C2—C3—C4—F1	−178.93 (14)	C1—S—C10—C11	−84.14 (14)
C2—C3—C4—C5	−0.4 (3)	C15—C10—C11—C12	1.1 (2)
F1—C4—C5—C6	179.38 (15)	S—C10—C11—C12	−179.07 (13)
C3—C4—C5—C6	0.9 (3)	C10—C11—C12—C13	−0.6 (3)
C4—C5—C6—C7	−0.1 (2)	C11—C12—C13—F2	178.91 (15)
C8—O1—C7—C6	177.63 (15)	C11—C12—C13—C14	−0.4 (3)
C8—O1—C7—C2	−0.46 (17)	F2—C13—C14—C15	−178.45 (15)
C5—C6—C7—O1	−178.90 (15)	C12—C13—C14—C15	0.8 (3)
C5—C6—C7—C2	−1.1 (3)	C13—C14—C15—C10	−0.3 (3)
C3—C2—C7—O1	179.63 (14)	C11—C10—C15—C14	−0.6 (2)
C1—C2—C7—O1	0.64 (17)	S—C10—C15—C14	179.53 (13)
C3—C2—C7—C6	1.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.93	2.45	3.247 (2)	144
C14—H14···F2ⁱⁱ	0.93	2.53	3.441 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀F₂O₃S
M_r	308.29
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.2799 (9), 9.5161 (12), 10.1052 (13)
α, β, γ (°)	89.844 (2), 75.057 (2), 74.558 (2)
V (Å³)	650.32 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.674, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	5657, 2797, 2404
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.10
No. of reflections	2797
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.39

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
C11—H11···O2ⁱ	0.93	2.45	3.247 (2)	143.7
C14—H14···F2ⁱⁱ	0.93	2.53	3.441 (2)	168.0

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

References

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Volume 66| Part 8| August 2010| Page o1909

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