3-(4-Bromo­phenyl­sulfon­yl)-5-ethyl-2-methyl-1-benzofuran

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

doi:10.1107/S1600536812048313

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3487

doi:10.1107/S1600536812048313

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3-(4-Bromophenylsulfonyl)-5-ethyl-2-methyl-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 8 November 2012; accepted 25 November 2012; online 30 November 2012)

In the title compound, C₁₇H₁₅BrO₃S, the 4-bromophenyl ring makes a dihedral angle of 76.58 (9)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For the crystal structures of related compounds, see: Choi et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₇H₁₅BrO₃S
M_r = 379.26
Tetragonal, P 4₃
a = 10.2785 (3) Å
c = 15.2899 (6) Å
V = 1615.34 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.68 mm⁻¹
T = 173 K
0.31 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.450, T_max = 0.746
8518 measured reflections
3085 independent reflections
2558 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.067
S = 1.03
3085 reflections
201 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1000 Friedel pairs
Flack parameter: 0.001 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.53	3.238 (4)	131
C11—H11A⋯O3ⁱⁱ	0.98	2.58	3.321 (4)	132
C14—H14⋯Cgⁱⁱⁱ	0.95	2.70	3.495 (4)	142
Symmetry codes: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-y+1, x, z-{\script{1\over 4}}]$ ; (iii) $[y, -x+1, z+{\script{1\over 4}}]$ .

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, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812048313/rn2111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048313/rn2111Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048313/rn2111Isup3.cml

checkCIF report

Comment top

Many compounds containing the benzofuran skeleton have attracted much interest owing to their biological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). As a part of our ongoing study of 5-ethyl-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) or 3-fluorophenylsulfonyl (Choi et al., 2011) substituents in the 3-position, we report herein the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group P4₃ in spite of having no asymmetric C atoms.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofuran ring is 76.58 (9)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For the crystal structures of related compounds, see: Choi et al. (2010, 2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-ethyl-2-methyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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 68%, m.p. 404–405 K; R_f = 0.61 (benzene)]. 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.

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, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Bruker, 2009).

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 small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry code: (i) - x, - y + 1, z - 1/2 (ii) - y + 1, x, z - 1/4 (iii) y, - x + 1, z + 1/4 (iv) - x, - y + 1, z + 1/2

3-(4-Bromophenylsulfonyl)-5-ethyl-2-methyl-1-benzofuran top

Crystal data top

C₁₇H₁₅BrO₃S	D_x = 1.559 Mg m⁻³
M_r = 379.26	Melting point = 404–405 K
Tetragonal, P4₃	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4cw	Cell parameters from 2851 reflections
a = 10.2785 (3) Å	θ = 2.4–23.1°
c = 15.2899 (6) Å	µ = 2.68 mm⁻¹
V = 1615.34 (9) Å³	T = 173 K
Z = 4	Block, colourless
F(000) = 768	0.31 × 0.17 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3085 independent reflections
Radiation source: rotating anode	2558 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ϕ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→12
T_min = 0.450, T_max = 0.746	l = −20→13
8518 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0094P)² + 0.1451P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3085 reflections	Δρ_max = 0.35 e Å⁻³
201 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1000 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.001 (7)

Crystal data top

C₁₇H₁₅BrO₃S	Z = 4
M_r = 379.26	Mo Kα radiation
Tetragonal, P4₃	µ = 2.68 mm⁻¹
a = 10.2785 (3) Å	T = 173 K
c = 15.2899 (6) Å	0.31 × 0.17 × 0.15 mm
V = 1615.34 (9) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3085 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2558 reflections with I > 2σ(I)
T_min = 0.450, T_max = 0.746	R_int = 0.035
8518 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.35 e Å⁻³
S = 1.03	Δρ_min = −0.29 e Å⁻³
3085 reflections	Absolute structure: Flack (1983), 1000 Friedel pairs
201 parameters	Absolute structure parameter: 0.001 (7)
1 restraint

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
Br1	0.83341 (3)	0.52123 (5)	0.64403 (3)	0.06379 (15)
S1	0.22891 (7)	0.40370 (7)	0.69506 (5)	0.02917 (17)
O1	0.1117 (2)	0.2989 (2)	0.46167 (13)	0.0331 (5)
O2	0.2142 (2)	0.2825 (2)	0.73957 (15)	0.0401 (6)
O3	0.1697 (2)	0.5188 (2)	0.73023 (15)	0.0372 (5)
C12	0.3955 (3)	0.4357 (3)	0.68213 (18)	0.0248 (6)
C2	0.1292 (3)	0.4919 (3)	0.5329 (2)	0.0250 (6)
C17	0.4835 (3)	0.3333 (3)	0.6829 (2)	0.0357 (7)
H17	0.4546	0.2464	0.6912	0.043*
C13	0.4374 (3)	0.5626 (3)	0.6707 (2)	0.0346 (8)
H13	0.3763	0.6319	0.6705	0.042*
C16	0.6140 (3)	0.3604 (3)	0.6713 (2)	0.0394 (8)
H16	0.6757	0.2916	0.6712	0.047*
C15	0.6542 (3)	0.4857 (4)	0.66010 (19)	0.0390 (8)
C6	0.0458 (3)	0.4963 (3)	0.3844 (2)	0.0370 (7)
H6	0.0223	0.4525	0.3320	0.044*
C7	0.0933 (3)	0.4311 (3)	0.4558 (2)	0.0287 (7)
C5	0.0339 (3)	0.6299 (3)	0.3931 (3)	0.0382 (7)
H5	0.0008	0.6787	0.3452	0.046*
C3	0.1165 (3)	0.6262 (3)	0.5399 (2)	0.0299 (7)
H3	0.1403	0.6696	0.5923	0.036*
C8	0.1590 (3)	0.2747 (3)	0.5441 (2)	0.0295 (7)
C9	0.0514 (4)	0.8410 (3)	0.4760 (3)	0.0454 (9)
H9A	0.0846	0.8705	0.5335	0.054*
H9B	0.1046	0.8832	0.4301	0.054*
C14	0.5674 (3)	0.5881 (3)	0.6595 (2)	0.0392 (8)
H14	0.5971	0.6748	0.6515	0.047*
C4	0.0687 (3)	0.6956 (3)	0.4694 (2)	0.0359 (8)
C1	0.1709 (3)	0.3870 (3)	0.58850 (19)	0.0275 (7)
C11	0.1847 (3)	0.1373 (3)	0.5637 (2)	0.0399 (8)
H11A	0.2469	0.1025	0.5212	0.060*
H11B	0.1033	0.0880	0.5603	0.060*
H11C	0.2210	0.1297	0.6228	0.060*
C10	−0.0874 (4)	0.8851 (4)	0.4663 (3)	0.0598 (11)
H10A	−0.1202	0.8595	0.4086	0.090*
H10B	−0.0917	0.9799	0.4721	0.090*
H10C	−0.1409	0.8446	0.5119	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02640 (18)	0.1092 (4)	0.0558 (2)	−0.00760 (19)	0.00298 (19)	−0.0095 (3)
S1	0.0271 (4)	0.0358 (4)	0.0246 (3)	−0.0022 (3)	0.0028 (3)	−0.0006 (4)
O1	0.0342 (12)	0.0308 (12)	0.0344 (12)	−0.0039 (9)	−0.0097 (10)	−0.0053 (10)
O2	0.0447 (14)	0.0415 (14)	0.0340 (12)	−0.0079 (10)	0.0037 (11)	0.0077 (11)
O3	0.0330 (13)	0.0478 (14)	0.0308 (12)	0.0037 (10)	0.0048 (10)	−0.0083 (11)
C12	0.0189 (14)	0.0371 (17)	0.0183 (13)	−0.0009 (12)	0.0012 (12)	−0.0052 (13)
C2	0.0176 (14)	0.0285 (16)	0.0288 (16)	−0.0047 (12)	0.0025 (13)	−0.0043 (13)
C17	0.0399 (19)	0.0355 (18)	0.0316 (16)	0.0026 (13)	0.0022 (15)	0.0029 (15)
C13	0.0315 (17)	0.0337 (18)	0.0387 (19)	0.0036 (13)	0.0008 (14)	−0.0074 (14)
C16	0.0329 (18)	0.052 (2)	0.0330 (18)	0.0134 (15)	−0.0038 (14)	−0.0043 (16)
C15	0.0219 (15)	0.071 (3)	0.0243 (17)	−0.0017 (15)	0.0011 (14)	−0.0056 (17)
C6	0.0384 (18)	0.0387 (17)	0.0338 (17)	−0.0044 (14)	−0.0098 (16)	−0.0033 (16)
C7	0.0233 (15)	0.0279 (16)	0.0348 (17)	−0.0020 (12)	−0.0040 (13)	−0.0018 (14)
C5	0.0345 (18)	0.0388 (18)	0.0414 (17)	−0.0023 (14)	−0.0121 (17)	0.006 (2)
C3	0.0296 (17)	0.0273 (17)	0.0329 (17)	−0.0052 (13)	−0.0018 (14)	−0.0028 (14)
C8	0.0272 (17)	0.0302 (17)	0.0312 (17)	−0.0024 (13)	−0.0016 (14)	0.0012 (14)
C9	0.058 (2)	0.0264 (18)	0.052 (2)	−0.0003 (16)	−0.0081 (19)	0.0021 (16)
C14	0.0355 (18)	0.0398 (19)	0.042 (2)	−0.0093 (14)	0.0031 (16)	−0.0073 (16)
C4	0.0341 (18)	0.0313 (18)	0.0423 (19)	−0.0045 (13)	−0.0024 (15)	−0.0010 (15)
C1	0.0221 (16)	0.0302 (17)	0.0302 (16)	−0.0048 (12)	0.0000 (13)	0.0004 (14)
C11	0.043 (2)	0.0305 (18)	0.047 (2)	−0.0022 (15)	−0.0034 (17)	−0.0018 (16)
C10	0.072 (3)	0.034 (2)	0.074 (3)	0.0137 (18)	−0.004 (2)	0.000 (2)

Geometric parameters (Å, º) top

Br1—C15	1.894 (3)	C6—C5	1.384 (4)
S1—O2	1.427 (2)	C6—H6	0.9500
S1—O3	1.435 (2)	C5—C4	1.395 (5)
S1—C1	1.743 (3)	C5—H5	0.9500
S1—C12	1.754 (3)	C3—C4	1.382 (4)
O1—C8	1.374 (4)	C3—H3	0.9500
O1—C7	1.376 (3)	C8—C1	1.345 (4)
C12—C13	1.385 (4)	C8—C11	1.467 (4)
C12—C17	1.388 (4)	C9—C10	1.505 (5)
C2—C7	1.384 (4)	C9—C4	1.509 (4)
C2—C3	1.391 (4)	C9—H9A	0.9900
C2—C1	1.438 (4)	C9—H9B	0.9900
C17—C16	1.381 (4)	C14—H14	0.9500
C17—H17	0.9500	C11—H11A	0.9800
C13—C14	1.372 (4)	C11—H11B	0.9800
C13—H13	0.9500	C11—H11C	0.9800
C16—C15	1.364 (5)	C10—H10A	0.9800
C16—H16	0.9500	C10—H10B	0.9800
C15—C14	1.381 (5)	C10—H10C	0.9800
C6—C7	1.371 (4)

O2—S1—O3	119.73 (14)	C4—C3—C2	119.0 (3)
O2—S1—C1	108.87 (14)	C4—C3—H3	120.5
O3—S1—C1	106.63 (14)	C2—C3—H3	120.5
O2—S1—C12	108.70 (14)	C1—C8—O1	109.9 (3)
O3—S1—C12	107.56 (13)	C1—C8—C11	134.9 (3)
C1—S1—C12	104.29 (13)	O1—C8—C11	115.2 (3)
C8—O1—C7	106.7 (2)	C10—C9—C4	113.8 (3)
C13—C12—C17	120.8 (3)	C10—C9—H9A	108.8
C13—C12—S1	119.7 (2)	C4—C9—H9A	108.8
C17—C12—S1	119.6 (2)	C10—C9—H9B	108.8
C7—C2—C3	119.2 (3)	C4—C9—H9B	108.8
C7—C2—C1	104.2 (2)	H9A—C9—H9B	107.7
C3—C2—C1	136.6 (3)	C13—C14—C15	118.9 (3)
C16—C17—C12	118.7 (3)	C13—C14—H14	120.6
C16—C17—H17	120.7	C15—C14—H14	120.6
C12—C17—H17	120.7	C3—C4—C5	119.6 (3)
C14—C13—C12	120.0 (3)	C3—C4—C9	120.1 (3)
C14—C13—H13	120.0	C5—C4—C9	120.3 (3)
C12—C13—H13	120.0	C8—C1—C2	108.5 (3)
C15—C16—C17	120.1 (3)	C8—C1—S1	126.0 (2)
C15—C16—H16	120.0	C2—C1—S1	125.5 (2)
C17—C16—H16	120.0	C8—C11—H11A	109.5
C16—C15—C14	121.7 (3)	C8—C11—H11B	109.5
C16—C15—Br1	119.6 (3)	H11A—C11—H11B	109.5
C14—C15—Br1	118.7 (3)	C8—C11—H11C	109.5
C7—C6—C5	116.1 (3)	H11A—C11—H11C	109.5
C7—C6—H6	122.0	H11B—C11—H11C	109.5
C5—C6—H6	122.0	C9—C10—H10A	109.5
C6—C7—O1	125.7 (3)	C9—C10—H10B	109.5
C6—C7—C2	123.6 (3)	H10A—C10—H10B	109.5
O1—C7—C2	110.7 (3)	C9—C10—H10C	109.5
C6—C5—C4	122.5 (3)	H10A—C10—H10C	109.5
C6—C5—H5	118.7	H10B—C10—H10C	109.5
C4—C5—H5	118.7

O2—S1—C12—C13	−156.8 (2)	C7—O1—C8—C11	179.7 (3)
O3—S1—C12—C13	−25.8 (3)	C12—C13—C14—C15	−0.1 (5)
C1—S1—C12—C13	87.2 (3)	C16—C15—C14—C13	0.1 (5)
O2—S1—C12—C17	23.7 (3)	Br1—C15—C14—C13	179.6 (2)
O3—S1—C12—C17	154.7 (2)	C2—C3—C4—C5	0.2 (5)
C1—S1—C12—C17	−92.3 (3)	C2—C3—C4—C9	178.8 (3)
C13—C12—C17—C16	−0.5 (4)	C6—C5—C4—C3	−0.3 (5)
S1—C12—C17—C16	179.1 (2)	C6—C5—C4—C9	−178.8 (3)
C17—C12—C13—C14	0.3 (4)	C10—C9—C4—C3	−117.6 (4)
S1—C12—C13—C14	−179.3 (3)	C10—C9—C4—C5	60.9 (5)
C12—C17—C16—C15	0.5 (5)	O1—C8—C1—C2	0.1 (3)
C17—C16—C15—C14	−0.3 (5)	C11—C8—C1—C2	180.0 (3)
C17—C16—C15—Br1	−179.8 (2)	O1—C8—C1—S1	−179.2 (2)
C5—C6—C7—O1	179.4 (3)	C11—C8—C1—S1	0.7 (5)
C5—C6—C7—C2	−0.4 (5)	C7—C2—C1—C8	0.2 (3)
C8—O1—C7—C6	−179.2 (3)	C3—C2—C1—C8	178.9 (3)
C8—O1—C7—C2	0.6 (3)	C7—C2—C1—S1	179.5 (2)
C3—C2—C7—C6	0.4 (5)	C3—C2—C1—S1	−1.8 (5)
C1—C2—C7—C6	179.3 (3)	O2—S1—C1—C8	−22.4 (3)
C3—C2—C7—O1	−179.4 (3)	O3—S1—C1—C8	−152.8 (3)
C1—C2—C7—O1	−0.5 (3)	C12—S1—C1—C8	93.5 (3)
C7—C6—C5—C4	0.4 (5)	O2—S1—C1—C2	158.4 (2)
C7—C2—C3—C4	−0.2 (4)	O3—S1—C1—C2	28.0 (3)
C1—C2—C3—C4	−178.8 (3)	C12—S1—C1—C2	−85.7 (3)
C7—O1—C8—C1	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.53	3.238 (4)	131
C11—H11A···O3ⁱⁱ	0.98	2.58	3.321 (4)	132
C14—H14···Cgⁱⁱⁱ	0.95	2.70	3.495 (4)	142

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) −y+1, x, z−1/4; (iii) y, −x+1, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₃S
M_r	379.26
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	173
a, c (Å)	10.2785 (3), 15.2899 (6)
V (Å³)	1615.34 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.68
Crystal size (mm)	0.31 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.450, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	8518, 3085, 2558
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.067, 1.03
No. of reflections	3085
No. of parameters	201
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29
Absolute structure	Flack (1983), 1000 Friedel pairs
Absolute structure parameter	0.001 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998), SHELXL97 (Bruker, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.53	3.238 (4)	131.3
C11—H11A···O3ⁱⁱ	0.98	2.58	3.321 (4)	132.3
C14—H14···Cgⁱⁱⁱ	0.95	2.70	3.495 (4)	141.6

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) −y+1, x, z−1/4; (iii) y, −x+1, z+1/4.

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

References

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Volume 68| Part 12| December 2012| Page o3487

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