5-Bromo-2,4,6-trimethyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S160053680802669X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1826

doi:10.1107/S160053680802669X

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5-Bromo-2,4,6-trimethyl-3-phenylsulfinyl-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 15 August 2008; accepted 18 August 2008; online 23 August 2008)

The title compound, C₁₇H₁₅BrO₂S, which was synthesized by the oxidation of 5-bromo-2,4,6-trimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid, features a trigonally-coordinated S atom. The phenyl ring is approximately perpendicular to the plane of the benzofuran fragment [dihedral angle 75.11 (7)°]. The crystal structure is stabilized by non-classical C—H⋯O and Br⋯Br interactions [3.7169 (6) Å].

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Seo et al. (2007 ); Choi et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₅BrO₂S
M_r = 363.26
Monoclinic, C 2/c
a = 22.114 (2) Å
b = 10.4281 (8) Å
c = 16.675 (1) Å
β = 125.767 (1)°
V = 3120.1 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.77 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.528, T_max = 0.762
8646 measured reflections
3055 independent reflections
2607 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.05
3055 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2ⁱ	0.93	2.54	3.371 (3)	150
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 datablock I. DOI: 10.1107/S160053680802669X/ng2486sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802669X/ng2486Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structures of 2-methyl-3-phenylsulfinyl-1-benzofuran analogues, viz. 5-bromo-2-methyl-3-phenylsulfinyl-1-benzofuran (Seo et al., 2007) and 5-iodo-2,7-dimethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2008). Here we report the crystal structure of the title compound, 5-bromo-2,4,6-trimethyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.023 (2) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9—C14) is almost perpendicular to the plane of the benzofuran ring system [75.11 (7)°]. The crystal packing (Fig. 2) is stabilized by intermolecular C—H···O interactions between a phenyl H atom of the phenylsulfinyl substituent and the oxygen of S?O unit, with a C14—H14···O2ⁱ separation of 2.54 Å (Fig. 2 and Table 1; symmetry code as in Fig. 2). Further stability comes from a Br···Brⁱⁱ interaction at 3.7169 (6) Å (Fig. 2).

Related literature top

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Seo et al. (2007); Choi et al. (2008).

Experimental top

77% 3-Chloroperoxybenzoic acid (123 mg, 0.55 mmol) was added in small portions to a stirred solution of 5-bromo-2,4,6-trimethyl-3-phenylsulfanyl-1-benzofuran (174 mg, 0.5 mmol) in dichloromethane (20 ml) at 273 K. After being stirred at room temperature for 4 h, 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 78%, m.p. 446–447 K; R_f = 0.79 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.36 (s, 3H), 2.47 (s, 3H), 2.72 (s, 3H), 7.21 (s, 1H), 7.41–7.49 (m, 5H); EI—MS 364 [M+2], 362 [M⁺].

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 30% probability level.
	Fig. 2. C—H···O and Br···Br interactions (dotted lines) in the title compound. [Symmetry code: (i) -x + 3/2, y + 1/2, -z + 3/2; (ii) -x + 1, y, -z + 1/2; (iii) -x + 3/2, y - 1/2, -z + 3/2.]

5-Bromo-2,4,6-trimethyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₁₇H₁₅BrO₂S	F(000) = 1472
M_r = 363.26	D_x = 1.547 Mg m⁻³
Monoclinic, C2/c	Melting point = 446–447 K
Hall symbol: -C_2yc	Mo Kα radiation, λ = 0.71073 Å
a = 22.114 (2) Å	Cell parameters from 4364 reflections
b = 10.4281 (8) Å	θ = 2.3–27.6°
c = 16.675 (1) Å	µ = 2.77 mm⁻¹
β = 125.767 (1)°	T = 298 K
V = 3120.1 (4) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	3055 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ϕ and ω scans	h = −27→26
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −9→12
T_min = 0.528, T_max = 0.762	l = −20→19
8646 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0445P)² + 2.4497P] where P = (F_o² + 2F_c²)/3
3055 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₂S	V = 3120.1 (4) Å³
M_r = 363.26	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.114 (2) Å	µ = 2.77 mm⁻¹
b = 10.4281 (8) Å	T = 298 K
c = 16.675 (1) Å	0.30 × 0.20 × 0.10 mm
β = 125.767 (1)°

Data collection top

Bruker SMART CCD diffractometer	3055 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2607 reflections with I > 2σ(I)
T_min = 0.528, T_max = 0.762	R_int = 0.015
8646 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
3055 reflections	Δρ_min = −0.65 e Å⁻³
193 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Br	0.533506 (16)	0.68321 (3)	0.38143 (2)	0.06177 (12)
S	0.74509 (3)	0.26302 (5)	0.71578 (4)	0.03881 (14)
O1	0.64417 (8)	0.49816 (16)	0.78355 (11)	0.0445 (4)
O2	0.70046 (10)	0.17705 (14)	0.62807 (13)	0.0493 (4)
C1	0.68826 (11)	0.3831 (2)	0.71386 (15)	0.0353 (4)
C2	0.63826 (11)	0.48016 (19)	0.64269 (15)	0.0325 (4)
C3	0.61280 (11)	0.5170 (2)	0.54678 (15)	0.0344 (4)
C4	0.56708 (11)	0.6251 (2)	0.51013 (16)	0.0387 (5)
C5	0.54362 (12)	0.6941 (2)	0.55938 (18)	0.0437 (5)
C6	0.56699 (12)	0.6518 (2)	0.65185 (18)	0.0433 (5)
H6	0.5516	0.6927	0.6866	0.052*
C7	0.61363 (11)	0.5474 (2)	0.69097 (15)	0.0368 (5)
C8	0.68938 (12)	0.3992 (2)	0.79549 (16)	0.0426 (5)
C9	0.80112 (11)	0.3609 (2)	0.69393 (15)	0.0354 (4)
C10	0.81357 (13)	0.3179 (2)	0.62659 (18)	0.0434 (5)
H10	0.7914	0.2426	0.5915	0.052*
C11	0.85940 (14)	0.3879 (3)	0.6117 (2)	0.0549 (6)
H11	0.8672	0.3608	0.5652	0.066*
C12	0.89331 (16)	0.4973 (3)	0.6653 (2)	0.0638 (7)
H12	0.9245	0.5438	0.6558	0.077*
C13	0.88124 (15)	0.5388 (3)	0.7338 (2)	0.0634 (7)
H13	0.9043	0.6132	0.7699	0.076*
C14	0.83519 (13)	0.4705 (2)	0.74880 (17)	0.0477 (6)
H14	0.8272	0.4979	0.7950	0.057*
C15	0.63413 (14)	0.4441 (2)	0.48921 (17)	0.0464 (5)
H15A	0.5921	0.4395	0.4211	0.070*
H15B	0.6494	0.3590	0.5156	0.070*
H15C	0.6745	0.4873	0.4941	0.070*
C16	0.49532 (16)	0.8122 (3)	0.5165 (2)	0.0644 (8)
H16A	0.4891	0.8484	0.5642	0.097*
H16B	0.4475	0.7893	0.4580	0.097*
H16C	0.5187	0.8740	0.5001	0.097*
C17	0.73101 (17)	0.3360 (3)	0.89359 (19)	0.0639 (8)
H17A	0.7592	0.2654	0.8942	0.096*
H17B	0.6965	0.3049	0.9064	0.096*
H17C	0.7643	0.3966	0.9437	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.06404 (19)	0.0623 (2)	0.05692 (18)	0.01291 (13)	0.03418 (15)	0.02859 (12)
S	0.0454 (3)	0.0340 (3)	0.0419 (3)	0.0069 (2)	0.0283 (2)	0.0079 (2)
O1	0.0456 (8)	0.0564 (10)	0.0369 (8)	0.0034 (7)	0.0271 (7)	−0.0034 (7)
O2	0.0603 (10)	0.0352 (8)	0.0607 (11)	−0.0054 (7)	0.0400 (9)	−0.0046 (7)
C1	0.0386 (10)	0.0360 (11)	0.0338 (10)	0.0023 (9)	0.0226 (9)	0.0029 (9)
C2	0.0326 (9)	0.0303 (10)	0.0366 (10)	−0.0017 (8)	0.0214 (9)	−0.0003 (8)
C3	0.0342 (10)	0.0333 (11)	0.0367 (10)	−0.0025 (8)	0.0214 (9)	0.0011 (8)
C4	0.0359 (10)	0.0351 (11)	0.0411 (11)	−0.0027 (9)	0.0203 (9)	0.0058 (9)
C5	0.0334 (11)	0.0353 (12)	0.0542 (14)	−0.0009 (9)	0.0209 (10)	−0.0011 (10)
C6	0.0348 (11)	0.0436 (12)	0.0509 (13)	−0.0014 (9)	0.0247 (10)	−0.0110 (10)
C7	0.0342 (10)	0.0400 (11)	0.0377 (11)	−0.0045 (9)	0.0219 (9)	−0.0047 (9)
C8	0.0443 (11)	0.0491 (13)	0.0372 (11)	0.0020 (10)	0.0254 (10)	0.0040 (10)
C9	0.0354 (10)	0.0327 (10)	0.0371 (11)	0.0051 (8)	0.0206 (9)	0.0033 (9)
C10	0.0488 (13)	0.0405 (12)	0.0452 (12)	−0.0009 (10)	0.0298 (11)	−0.0044 (9)
C11	0.0593 (15)	0.0597 (16)	0.0608 (15)	−0.0007 (13)	0.0437 (13)	0.0003 (13)
C12	0.0615 (16)	0.0614 (17)	0.0824 (19)	−0.0138 (14)	0.0499 (16)	−0.0009 (15)
C13	0.0581 (15)	0.0517 (15)	0.0765 (19)	−0.0172 (13)	0.0371 (15)	−0.0170 (14)
C14	0.0487 (13)	0.0460 (13)	0.0479 (13)	−0.0011 (11)	0.0279 (11)	−0.0100 (10)
C15	0.0559 (13)	0.0511 (14)	0.0396 (12)	0.0086 (11)	0.0320 (11)	0.0078 (10)
C16	0.0557 (15)	0.0468 (15)	0.080 (2)	0.0150 (12)	0.0338 (15)	0.0080 (13)
C17	0.0720 (18)	0.082 (2)	0.0390 (13)	0.0163 (15)	0.0334 (13)	0.0139 (13)

Geometric parameters (Å, º) top

Br—Brⁱ	3.7169 (6)	C9—C14	1.380 (3)
Br—C4	1.914 (2)	C10—C11	1.385 (3)
S—O2	1.4930 (18)	C10—H10	0.9300
S—C1	1.761 (2)	C11—C12	1.371 (4)
S—C9	1.799 (2)	C11—H11	0.9300
O1—C8	1.368 (3)	C12—C13	1.385 (4)
O1—C7	1.373 (3)	C12—H12	0.9300
C1—C8	1.357 (3)	C13—C14	1.380 (4)
C1—C2	1.456 (3)	C13—H13	0.9300
C2—C7	1.396 (3)	C14—H14	0.9300
C2—C3	1.404 (3)	C15—H15A	0.9600
C3—C4	1.394 (3)	C15—H15B	0.9600
C3—C15	1.500 (3)	C15—H15C	0.9600
C4—C5	1.400 (3)	C16—H16A	0.9600
C5—C6	1.382 (4)	C16—H16B	0.9600
C5—C16	1.509 (3)	C16—H16C	0.9600
C6—C7	1.373 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C8—C17	1.483 (3)	C17—H17C	0.9600
C9—C10	1.378 (3)

O2—S—C1	110.68 (10)	C9—C10—H10	120.3
O2—S—C9	106.35 (10)	C11—C10—H10	120.3
C1—S—C9	99.28 (10)	C12—C11—C10	120.0 (2)
C8—O1—C7	106.46 (16)	C12—C11—H11	120.0
C8—C1—C2	106.94 (19)	C10—C11—H11	120.0
C8—C1—S	118.37 (17)	C11—C12—C13	120.2 (2)
C2—C1—S	134.65 (15)	C11—C12—H12	119.9
C7—C2—C3	119.17 (19)	C13—C12—H12	119.9
C7—C2—C1	104.22 (17)	C14—C13—C12	120.4 (2)
C3—C2—C1	136.61 (19)	C14—C13—H13	119.8
C4—C3—C2	115.22 (19)	C12—C13—H13	119.8
C4—C3—C15	123.21 (19)	C13—C14—C9	118.8 (2)
C2—C3—C15	121.57 (19)	C13—C14—H14	120.6
C3—C4—C5	125.5 (2)	C9—C14—H14	120.6
C3—C4—Br	117.02 (16)	C3—C15—H15A	109.5
C5—C4—Br	117.45 (16)	C3—C15—H15B	109.5
C6—C5—C4	117.7 (2)	H15A—C15—H15B	109.5
C6—C5—C16	119.3 (2)	C3—C15—H15C	109.5
C4—C5—C16	123.0 (2)	H15A—C15—H15C	109.5
C7—C6—C5	118.1 (2)	H15B—C15—H15C	109.5
C7—C6—H6	121.0	C5—C16—H16A	109.5
C5—C6—H6	121.0	C5—C16—H16B	109.5
O1—C7—C6	124.74 (19)	H16A—C16—H16B	109.5
O1—C7—C2	111.03 (18)	C5—C16—H16C	109.5
C6—C7—C2	124.2 (2)	H16A—C16—H16C	109.5
C1—C8—O1	111.34 (19)	H16B—C16—H16C	109.5
C1—C8—C17	133.4 (2)	C8—C17—H17A	109.5
O1—C8—C17	115.2 (2)	C8—C17—H17B	109.5
C10—C9—C14	121.2 (2)	H17A—C17—H17B	109.5
C10—C9—S	118.02 (17)	C8—C17—H17C	109.5
C14—C9—S	120.60 (17)	H17A—C17—H17C	109.5
C9—C10—C11	119.4 (2)	H17B—C17—H17C	109.5

O2—S—C1—C8	127.65 (18)	C5—C6—C7—O1	176.8 (2)
C9—S—C1—C8	−120.85 (19)	C5—C6—C7—C2	−0.9 (3)
O2—S—C1—C2	−55.0 (2)	C3—C2—C7—O1	179.99 (17)
C9—S—C1—C2	56.5 (2)	C1—C2—C7—O1	−0.4 (2)
C8—C1—C2—C7	0.1 (2)	C3—C2—C7—C6	−2.0 (3)
S—C1—C2—C7	−177.40 (18)	C1—C2—C7—C6	177.5 (2)
C8—C1—C2—C3	179.6 (2)	C2—C1—C8—O1	0.2 (3)
S—C1—C2—C3	2.0 (4)	S—C1—C8—O1	178.23 (15)
C7—C2—C3—C4	3.4 (3)	C2—C1—C8—C17	−177.0 (3)
C1—C2—C3—C4	−176.0 (2)	S—C1—C8—C17	1.1 (4)
C7—C2—C3—C15	−176.74 (19)	C7—O1—C8—C1	−0.5 (2)
C1—C2—C3—C15	3.9 (4)	C7—O1—C8—C17	177.2 (2)
C2—C3—C4—C5	−2.3 (3)	O2—S—C9—C10	−20.6 (2)
C15—C3—C4—C5	177.9 (2)	C1—S—C9—C10	−135.45 (18)
C2—C3—C4—Br	177.91 (14)	O2—S—C9—C14	164.37 (18)
C15—C3—C4—Br	−1.9 (3)	C1—S—C9—C14	49.5 (2)
C3—C4—C5—C6	−0.5 (3)	C14—C9—C10—C11	−1.9 (3)
Br—C4—C5—C6	179.28 (16)	S—C9—C10—C11	−176.89 (19)
C3—C4—C5—C16	178.7 (2)	C9—C10—C11—C12	1.5 (4)
Br—C4—C5—C16	−1.5 (3)	C10—C11—C12—C13	−0.7 (4)
C4—C5—C6—C7	2.1 (3)	C11—C12—C13—C14	0.1 (5)
C16—C5—C6—C7	−177.1 (2)	C12—C13—C14—C9	−0.4 (4)
C8—O1—C7—C6	−177.4 (2)	C10—C9—C14—C13	1.3 (4)
C8—O1—C7—C2	0.6 (2)	S—C9—C14—C13	176.2 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱⁱ	0.93	2.54	3.371 (3)	150
C15—H15A···Br	0.96	2.75	3.118 (2)	103

Symmetry code: (ii) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₂S
M_r	363.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	22.114 (2), 10.4281 (8), 16.675 (1)
β (°)	125.767 (1)
V (Å³)	3120.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.77
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.528, 0.762
No. of measured, independent and observed [I > 2σ(I)] reflections	8646, 3055, 2607
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.05
No. of reflections	3055
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.65

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
C14—H14···O2ⁱ	0.93	2.54	3.371 (3)	149.6
C15—H15A···Br	0.96	2.75	3.118 (2)	103

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

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., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o486. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o3204. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. 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 9| September 2008| Page o1826

doi:10.1107/S160053680802669X

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