3-(4-Fluoro­phenyl­sulfin­yl)-5-iodo-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536811012591

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1082

doi:10.1107/S1600536811012591

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3-(4-Fluorophenylsulfinyl)-5-iodo-2,7-dimethyl-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 17 February 2011; accepted 5 April 2011; online 13 April 2011)

In the title compound, C₁₆H₁₂FlO₂S, the 4-fluorophenyl ring makes a dihedral angle of 80.21 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds. The crystal structure also exhibits an intermolecular I⋯F contact [3.423 (2) Å].

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 our previous structural studies of related 3-(4-fluorophenylsulfinyl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ,c ).

Experimental

Crystal data

C₁₆H₁₂FIO₂S
M_r = 414.22
Triclinic, $[P \overline 1]$
a = 9.0845 (2) Å
b = 9.2761 (2) Å
c = 10.1252 (2) Å
α = 71.315 (1)°
β = 80.838 (1)°
γ = 70.485 (1)°
V = 760.53 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.25 mm⁻¹
T = 173 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.603, T_max = 0.666
13286 measured reflections
3477 independent reflections
3276 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.065
S = 1.15
3477 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.95	2.51	3.444 (3)	169
C9—H9A⋯O2ⁱⁱ	0.98	2.48	3.437 (3)	165
C15—H15⋯O1ⁱⁱⁱ	0.95	2.49	3.342 (3)	149
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (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/S1600536811012591/bv2179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012591/bv2179Isup2.hkl

checkCIF report

Comment top

A series of benzofuran ring system have attracted much attention owing to their interesting pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). 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 3-(4-fluorophenylsulfinyl)-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report here on 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 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the mean plane of the benzofuran fragment and the 4-fluorophenyl ring is 80.21 (6)°. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the oxygen of the S═O unit (Table 1: C3—H3···O2ⁱ), and the second one between a methyl H atom and the oxygen of the S═O unit (Table 1: C9—H9A···O2ⁱⁱ), and the third one between a 4-fluorophenyl H atom and the furan O atom (Table 1; C15—H15···O1ⁱⁱⁱ). The crystal packing (Fig. 2) is further stabilized by an I···F contact at 3.423 (2) Å [C4—I1···F1^iv = 161.10 (6) ° ].

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 our previous structural studies of related 3-(4-fluorophenylsulfinyl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2,7-dimethyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (40 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 423–424 K; Rf = 0.65 (hexane-ethyl acetate, 1:1 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: 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. A view of the C—H···O and I···F interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 2, - z + 1 ; (ii) - x + 1, - y + 1, - z + 1; (iii) x, y + 1, z; (iv) - x + 2, - y + 2, - z + 1; (v) x, y - 1, z; (vi) - x + 2, - y + 2, - z + 1.]

3-(4-Fluorophenylsulfinyl)-5-iodo-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₂FIO₂S	Z = 2
M_r = 414.22	F(000) = 404
Triclinic, P1	D_x = 1.809 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0845 (2) Å	Cell parameters from 9933 reflections
b = 9.2761 (2) Å	θ = 2.4–27.5°
c = 10.1252 (2) Å	µ = 2.25 mm⁻¹
α = 71.315 (1)°	T = 173 K
β = 80.838 (1)°	Block, colourless
γ = 70.485 (1)°	0.25 × 0.23 × 0.20 mm
V = 760.53 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3477 independent reflections
Radiation source: rotating anode	3276 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.033
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→11
T_min = 0.603, T_max = 0.666	l = −13→13
13286 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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F²) = 0.065	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0297P)² + 0.3709P] where P = (F_o² + 2F_c²)/3
3477 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

C₁₆H₁₂FIO₂S	γ = 70.485 (1)°
M_r = 414.22	V = 760.53 (3) Å³
Triclinic, P1	Z = 2
a = 9.0845 (2) Å	Mo Kα radiation
b = 9.2761 (2) Å	µ = 2.25 mm⁻¹
c = 10.1252 (2) Å	T = 173 K
α = 71.315 (1)°	0.25 × 0.23 × 0.20 mm
β = 80.838 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3477 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3276 reflections with I > 2σ(I)
T_min = 0.603, T_max = 0.666	R_int = 0.033
13286 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.15	Δρ_max = 0.29 e Å⁻³
3477 reflections	Δρ_min = −1.25 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
I1	0.885022 (19)	0.64773 (2)	0.817121 (15)	0.04100 (7)
S1	0.46511 (6)	0.87701 (6)	0.28833 (5)	0.02623 (11)
F1	0.91534 (19)	1.2241 (2)	0.00671 (16)	0.0487 (4)
O1	0.70380 (17)	0.42169 (18)	0.37299 (15)	0.0282 (3)
O2	0.39368 (18)	0.9370 (2)	0.41076 (16)	0.0337 (3)
C1	0.5892 (2)	0.6822 (2)	0.3520 (2)	0.0247 (4)
C2	0.6891 (2)	0.6179 (2)	0.4686 (2)	0.0242 (4)
C3	0.7247 (2)	0.6783 (3)	0.5651 (2)	0.0258 (4)
H3	0.6807	0.7873	0.5631	0.031*
C4	0.8280 (2)	0.5699 (3)	0.6641 (2)	0.0289 (4)
C5	0.8967 (2)	0.4099 (3)	0.6678 (2)	0.0302 (4)
H5	0.9687	0.3419	0.7369	0.036*
C6	0.8620 (2)	0.3475 (3)	0.5724 (2)	0.0283 (4)
C8	0.6016 (2)	0.5613 (3)	0.3001 (2)	0.0269 (4)
C7	0.7563 (2)	0.4570 (3)	0.4756 (2)	0.0255 (4)
C9	0.9340 (3)	0.1760 (3)	0.5733 (3)	0.0369 (5)
H9A	0.8521	0.1323	0.5663	0.055*
H9B	0.9865	0.1146	0.6604	0.055*
H9C	1.0105	0.1694	0.4937	0.055*
C10	0.5306 (3)	0.5520 (3)	0.1823 (3)	0.0362 (5)
H10A	0.4481	0.6521	0.1470	0.054*
H10B	0.4857	0.4632	0.2145	0.054*
H10C	0.6112	0.5344	0.1074	0.054*
C11	0.6111 (2)	0.9745 (2)	0.2075 (2)	0.0254 (4)
C12	0.6769 (3)	0.9632 (3)	0.0763 (2)	0.0313 (5)
H12	0.6505	0.8982	0.0337	0.038*
C13	0.7807 (3)	1.0468 (3)	0.0079 (2)	0.0353 (5)
H13	0.8270	1.0405	−0.0819	0.042*
C14	0.8148 (3)	1.1395 (3)	0.0736 (2)	0.0333 (5)
C15	0.7536 (3)	1.1507 (3)	0.2047 (2)	0.0328 (5)
H15	0.7828	1.2132	0.2481	0.039*
C16	0.6476 (3)	1.0676 (3)	0.2718 (2)	0.0296 (4)
H16	0.6007	1.0750	0.3612	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.05179 (11)	0.04985 (12)	0.02844 (9)	−0.02072 (8)	−0.01085 (7)	−0.01101 (7)
S1	0.0251 (2)	0.0264 (2)	0.0265 (2)	−0.0037 (2)	−0.00507 (18)	−0.0092 (2)
F1	0.0549 (9)	0.0500 (9)	0.0437 (8)	−0.0300 (8)	0.0008 (7)	−0.0036 (7)
O1	0.0311 (7)	0.0245 (7)	0.0302 (7)	−0.0066 (6)	−0.0046 (6)	−0.0101 (6)
O2	0.0319 (8)	0.0362 (9)	0.0336 (8)	−0.0068 (7)	0.0023 (6)	−0.0164 (7)
C1	0.0253 (9)	0.0243 (10)	0.0237 (9)	−0.0055 (8)	−0.0033 (7)	−0.0070 (8)
C2	0.0230 (9)	0.0262 (10)	0.0228 (9)	−0.0072 (8)	−0.0007 (7)	−0.0066 (8)
C3	0.0264 (9)	0.0276 (10)	0.0246 (9)	−0.0094 (8)	−0.0008 (7)	−0.0081 (8)
C4	0.0311 (10)	0.0363 (12)	0.0225 (9)	−0.0143 (9)	−0.0024 (8)	−0.0080 (9)
C5	0.0277 (10)	0.0325 (11)	0.0262 (10)	−0.0096 (9)	−0.0040 (8)	−0.0009 (9)
C6	0.0260 (9)	0.0261 (10)	0.0292 (10)	−0.0080 (8)	−0.0004 (8)	−0.0037 (8)
C8	0.0267 (9)	0.0278 (10)	0.0270 (10)	−0.0080 (8)	−0.0019 (7)	−0.0091 (8)
C7	0.0263 (9)	0.0257 (10)	0.0257 (9)	−0.0093 (8)	−0.0008 (7)	−0.0079 (8)
C9	0.0336 (11)	0.0255 (11)	0.0439 (13)	−0.0040 (9)	−0.0051 (9)	−0.0034 (10)
C10	0.0412 (12)	0.0362 (12)	0.0365 (12)	−0.0103 (10)	−0.0107 (9)	−0.0148 (10)
C11	0.0260 (9)	0.0222 (9)	0.0245 (9)	−0.0022 (8)	−0.0055 (7)	−0.0055 (8)
C12	0.0350 (11)	0.0338 (11)	0.0275 (10)	−0.0081 (9)	−0.0046 (8)	−0.0132 (9)
C13	0.0373 (11)	0.0436 (13)	0.0238 (10)	−0.0105 (10)	−0.0023 (8)	−0.0096 (10)
C14	0.0348 (11)	0.0284 (11)	0.0324 (11)	−0.0098 (9)	−0.0056 (9)	−0.0012 (9)
C15	0.0381 (11)	0.0257 (10)	0.0368 (12)	−0.0077 (9)	−0.0075 (9)	−0.0111 (9)
C16	0.0339 (10)	0.0270 (10)	0.0274 (10)	−0.0043 (9)	−0.0038 (8)	−0.0111 (9)

Geometric parameters (Å, º) top

I1—C4	2.101 (2)	C6—C9	1.502 (3)
I1—F1ⁱ	3.4226 (16)	C8—C10	1.481 (3)
S1—O2	1.4874 (16)	C9—H9A	0.9800
S1—C1	1.754 (2)	C9—H9B	0.9800
S1—C11	1.797 (2)	C9—H9C	0.9800
F1—C14	1.360 (3)	C10—H10A	0.9800
O1—C8	1.374 (3)	C10—H10B	0.9800
O1—C7	1.377 (3)	C10—H10C	0.9800
C1—C8	1.349 (3)	C11—C16	1.378 (3)
C1—C2	1.450 (3)	C11—C12	1.388 (3)
C2—C7	1.394 (3)	C12—C13	1.381 (3)
C2—C3	1.395 (3)	C12—H12	0.9500
C3—C4	1.385 (3)	C13—C14	1.374 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.396 (3)	C14—C15	1.378 (3)
C5—C6	1.395 (3)	C15—C16	1.391 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.387 (3)	C16—H16	0.9500

C4—I1—F1ⁱ	161.10 (6)	C6—C9—H9B	109.5
O2—S1—C1	107.49 (10)	H9A—C9—H9B	109.5
O2—S1—C11	106.55 (10)	C6—C9—H9C	109.5
C1—S1—C11	98.72 (9)	H9A—C9—H9C	109.5
C8—O1—C7	106.50 (16)	H9B—C9—H9C	109.5
C8—C1—C2	107.61 (18)	C8—C10—H10A	109.5
C8—C1—S1	123.72 (16)	C8—C10—H10B	109.5
C2—C1—S1	128.61 (16)	H10A—C10—H10B	109.5
C7—C2—C3	119.99 (19)	C8—C10—H10C	109.5
C7—C2—C1	104.33 (17)	H10A—C10—H10C	109.5
C3—C2—C1	135.67 (19)	H10B—C10—H10C	109.5
C4—C3—C2	116.1 (2)	C16—C11—C12	121.3 (2)
C4—C3—H3	122.0	C16—C11—S1	119.71 (16)
C2—C3—H3	122.0	C12—C11—S1	118.82 (17)
C3—C4—C5	123.2 (2)	C13—C12—C11	119.8 (2)
C3—C4—I1	119.05 (16)	C13—C12—H12	120.1
C5—C4—I1	117.79 (15)	C11—C12—H12	120.1
C6—C5—C4	121.5 (2)	C14—C13—C12	118.0 (2)
C6—C5—H5	119.3	C14—C13—H13	121.0
C4—C5—H5	119.3	C12—C13—H13	121.0
C7—C6—C5	114.6 (2)	F1—C14—C13	118.6 (2)
C7—C6—C9	122.6 (2)	F1—C14—C15	117.9 (2)
C5—C6—C9	122.8 (2)	C13—C14—C15	123.5 (2)
C1—C8—O1	110.86 (17)	C14—C15—C16	117.9 (2)
C1—C8—C10	133.1 (2)	C14—C15—H15	121.0
O1—C8—C10	116.02 (19)	C16—C15—H15	121.0
O1—C7—C6	124.59 (19)	C11—C16—C15	119.5 (2)
O1—C7—C2	110.69 (17)	C11—C16—H16	120.3
C6—C7—C2	124.7 (2)	C15—C16—H16	120.3
C6—C9—H9A	109.5

O2—S1—C1—C8	139.60 (18)	C8—O1—C7—C2	−0.2 (2)
C11—S1—C1—C8	−109.88 (19)	C5—C6—C7—O1	−179.19 (19)
O2—S1—C1—C2	−37.4 (2)	C9—C6—C7—O1	1.3 (3)
C11—S1—C1—C2	73.1 (2)	C5—C6—C7—C2	1.0 (3)
C8—C1—C2—C7	0.5 (2)	C9—C6—C7—C2	−178.5 (2)
S1—C1—C2—C7	177.84 (16)	C3—C2—C7—O1	178.93 (17)
C8—C1—C2—C3	−178.4 (2)	C1—C2—C7—O1	−0.1 (2)
S1—C1—C2—C3	−1.0 (4)	C3—C2—C7—C6	−1.2 (3)
C7—C2—C3—C4	0.1 (3)	C1—C2—C7—C6	179.7 (2)
C1—C2—C3—C4	178.8 (2)	O2—S1—C11—C16	7.08 (19)
C2—C3—C4—C5	1.3 (3)	C1—S1—C11—C16	−104.19 (18)
C2—C3—C4—I1	−178.54 (14)	O2—S1—C11—C12	−168.41 (16)
C3—C4—C5—C6	−1.5 (3)	C1—S1—C11—C12	80.32 (18)
I1—C4—C5—C6	178.28 (16)	C16—C11—C12—C13	−0.2 (3)
C4—C5—C6—C7	0.4 (3)	S1—C11—C12—C13	175.24 (17)
C4—C5—C6—C9	179.8 (2)	C11—C12—C13—C14	−0.1 (3)
C2—C1—C8—O1	−0.6 (2)	C12—C13—C14—F1	−179.2 (2)
S1—C1—C8—O1	−178.17 (14)	C12—C13—C14—C15	1.3 (4)
C2—C1—C8—C10	−179.3 (2)	F1—C14—C15—C16	178.33 (19)
S1—C1—C8—C10	3.1 (4)	C13—C14—C15—C16	−2.2 (4)
C7—O1—C8—C1	0.5 (2)	C12—C11—C16—C15	−0.7 (3)
C7—O1—C8—C10	179.49 (18)	S1—C11—C16—C15	−176.06 (16)
C8—O1—C7—C6	179.94 (19)	C14—C15—C16—C11	1.8 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱⁱ	0.95	2.51	3.444 (3)	169
C9—H9A···O2ⁱⁱⁱ	0.98	2.48	3.437 (3)	165
C15—H15···O1^iv	0.95	2.49	3.342 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂FIO₂S
M_r	414.22
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.0845 (2), 9.2761 (2), 10.1252 (2)
α, β, γ (°)	71.315 (1), 80.838 (1), 70.485 (1)
V (Å³)	760.53 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.25
Crystal size (mm)	0.25 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.603, 0.666
No. of measured, independent and observed [I > 2σ(I)] reflections	13286, 3477, 3276
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.065, 1.15
No. of reflections	3477
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −1.25

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	0.95	2.51	3.444 (3)	169
C9—H9A···O2ⁱⁱ	0.98	2.48	3.437 (3)	165
C15—H15···O1ⁱⁱⁱ	0.95	2.49	3.342 (3)	149

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

References

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Volume 67| Part 5| May 2011| Page o1082

doi:10.1107/S1600536811012591

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