Propyl 2-(5-bromo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

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

doi:10.1107/S160053680900453X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o520

doi:10.1107/S160053680900453X

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Propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate

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 8 December 2008; accepted 8 February 2009; online 13 February 2009)

In the title compound, C₁₄H₁₅BrO₄S, the S atom has a distorted trigonal–pyramidal coordination. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The molecules form slightly slipped π-stacked inversion-symmetric dimers by intermolecular aromatic π–π interactions, with a centroid-to-centroid distance of 3.695 (4) Å between the benzene rings of neighbouring molecules. The crystal packing is further stabilized by intermolecular C—H⋯π interactions between the methylene H atoms of the propyl group towards the benzene and furan rings of neighbouring molecules, respectively. Additionally, the crystal structure exhibits weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₁₄H₁₅BrO₄S
M_r = 359.23
Triclinic, $[P \overline 1]$
a = 8.4538 (6) Å
b = 9.8823 (7) Å
c = 10.3231 (7) Å
α = 72.358 (1)°
β = 81.200 (1)°
γ = 65.443 (1)°
V = 747.16 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.90 mm⁻¹
T = 298 K
0.60 × 0.50 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.187, T_max = 0.556
3932 measured reflections
2593 independent reflections
2359 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.07
2593 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1ⁱ	0.97	3.02	3.720 (3)	130
C12—H12B⋯Cg2ⁱ	0.97	2.90	3.826 (3)	161
C3—H3⋯O4ⁱⁱ	0.93	2.54	3.424 (3)	159
C5—H5⋯O3ⁱⁱⁱ	0.93	2.58	3.430 (4)	152
C9—H9B⋯O4^iv	0.97	2.37	3.321 (3)	167
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+2. Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.

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 datablocks global, I. DOI: 10.1107/S160053680900453X/zl2167sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900453X/zl2167Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing research on the synthesis and structure of alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, we have recently described the crystal structures of isopropyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and methyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008b). Here we report the crystal structure of the title compound, propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by intermolecular π–π stacking interactions between the benzene rings of neighbouring molecules. Via this interaction the molecules form slightly slipped π-stacked inversion symmetric dimers, with a centroid–centroid distance Cg1···Cg1ⁱⁱⁱ of 3.695 (4) Å between the benzene rings of neighbouring molecules. (Cg is the centroid of the C2–C7 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions; one between the hydrogen of the C11-methylene group and the benzene ring of the benzofuran unit, with a C11—H11B···Cg1ⁱ separation of 3.02 Å, and a second between the hydrogen of the C12-methylene group and the furan ring of the benzofuran unit, with a C12—H12B···Cg2ⁱ separation of 2.90 Å (Table 1 and Fig. 2; Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively, symmetry code as in Fig. 2). In addition, three weak intermolecular C—H···O hydrogen bonds in the structure were observed (Table 1 and Fig. 3); one between the hydrogen on benzene ring and the oxygen of the S═O unit (C3—H3···O4ⁱⁱ), a second between the hydrogen on benzene ring and the oxygen of the C═O unit (C5—H5···O3ⁱⁱⁱ), and a third between the hydrogen of the C9–methylene group and the S═O unit (C9—H9B···O4^iv), respectively.

Related literature top

For the crystal structures of similar alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (179 mg, 0.8 mmol) was added in small portions to a stirred solution of propyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (629 mg, 0.75 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 3 h at room temperature, 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 413–413.5 K; R_f = 0.55 (hexane–ethyl acetate, 1:2 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 0.94 (t, J = 7.32 Hz, 3H), 1.63–1.72 (m, 2H), 3.07 (s, 3H), 4.05 (s, 2H), 4.11 (t, J = 6.96 Hz, 2H), 7.40 (d, J = 8.76 Hz, 1H), 7.48 (dd, J = 8.76 Hz and J = 1.84 Hz, 1H), 8.09 (d, J = 1.84 Hz, 1H); EI-MS 360 [M+2], 358 [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. π—π and C—H···π interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1.]
	Fig. 3. Intermolecular C—H···O hydrogen bonds (dotted lines) in the title compound. [Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+2.]

Propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₄H₁₅BrO₄S	Z = 2
M_r = 359.23	F(000) = 364
Triclinic, P1	D_x = 1.597 Mg m⁻³
Hall symbol: -p_1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4538 (6) Å	Cell parameters from 2872 reflections
b = 9.8823 (7) Å	θ = 2.7–28.0°
c = 10.3231 (7) Å	µ = 2.90 mm⁻¹
α = 72.358 (1)°	T = 298 K
β = 81.200 (1)°	Block, colourless
γ = 65.443 (1)°	0.60 × 0.50 × 0.20 mm
V = 747.16 (9) Å³

Data collection top

Bruker SMART CCD diffractometer	2593 independent reflections
Radiation source: fine-focus sealed tube	2359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ϕ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −10→11
T_min = 0.187, T_max = 0.556	l = −12→10
3932 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) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0598P)² + 0.3564P] where P = (F_o² + 2F_c²)/3
2593 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₄H₁₅BrO₄S	γ = 65.443 (1)°
M_r = 359.23	V = 747.16 (9) Å³
Triclinic, P1	Z = 2
a = 8.4538 (6) Å	Mo Kα radiation
b = 9.8823 (7) Å	µ = 2.90 mm⁻¹
c = 10.3231 (7) Å	T = 298 K
α = 72.358 (1)°	0.60 × 0.50 × 0.20 mm
β = 81.200 (1)°

Data collection top

Bruker SMART CCD diffractometer	2593 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2359 reflections with I > 2σ(I)
T_min = 0.187, T_max = 0.556	R_int = 0.014
3932 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.07	Δρ_max = 0.62 e Å⁻³
2593 reflections	Δρ_min = −0.38 e Å⁻³
182 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
Br	0.68856 (4)	0.78591 (4)	0.61232 (4)	0.06138 (16)
S	0.26099 (9)	0.40306 (8)	0.96326 (6)	0.04277 (19)
O1	0.1656 (2)	0.5416 (2)	0.57292 (17)	0.0389 (4)
O2	0.0410 (3)	0.1435 (2)	0.7276 (3)	0.0651 (6)
O3	0.2856 (3)	0.1366 (3)	0.7909 (3)	0.0628 (6)
O4	0.2583 (3)	0.5257 (3)	1.0205 (2)	0.0565 (5)
C1	0.2557 (3)	0.4773 (3)	0.7850 (2)	0.0355 (5)
C2	0.3457 (3)	0.5694 (3)	0.6968 (2)	0.0345 (5)
C3	0.4701 (3)	0.6215 (3)	0.7124 (3)	0.0390 (6)
H3	0.5166	0.5970	0.7965	0.047*
C4	0.5206 (3)	0.7106 (3)	0.5974 (3)	0.0411 (6)
C5	0.4525 (4)	0.7510 (3)	0.4691 (3)	0.0448 (6)
H5	0.4882	0.8144	0.3949	0.054*
C6	0.3327 (3)	0.6968 (3)	0.4533 (3)	0.0421 (6)
H6	0.2877	0.7199	0.3689	0.051*
C7	0.2826 (3)	0.6069 (3)	0.5677 (3)	0.0367 (5)
C8	0.1513 (3)	0.4645 (3)	0.7068 (3)	0.0368 (5)
C9	0.0363 (3)	0.3784 (3)	0.7351 (3)	0.0408 (6)
H9A	−0.0412	0.4178	0.6600	0.049*
H9B	−0.0347	0.3956	0.8164	0.049*
C10	0.1380 (4)	0.2072 (3)	0.7546 (3)	0.0448 (6)
C11	0.1221 (5)	−0.0227 (4)	0.7402 (6)	0.0860 (14)
H11A	0.1843	−0.0769	0.8242	0.103*
H11B	0.2040	−0.0434	0.6648	0.103*
C12	−0.0195 (6)	−0.0757 (5)	0.7394 (6)	0.0900 (14)
H12A	−0.0800	−0.0196	0.6548	0.108*
H12B	0.0329	−0.1842	0.7418	0.108*
C13	−0.1468 (9)	−0.0548 (7)	0.8527 (6)	0.122 (2)
H13A	−0.2019	0.0527	0.8501	0.147*
H13B	−0.0889	−0.1122	0.9372	0.147*
H13C	−0.2332	−0.0913	0.8452	0.147*
C14	0.4798 (4)	0.2618 (4)	0.9755 (3)	0.0575 (8)
H14A	0.5592	0.3128	0.9465	0.086*
H14B	0.4965	0.1959	0.9185	0.086*
H14C	0.5011	0.2010	1.0681	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0581 (2)	0.0617 (2)	0.0766 (3)	−0.03898 (17)	−0.00471 (16)	−0.01173 (17)
S	0.0443 (4)	0.0525 (4)	0.0332 (3)	−0.0238 (3)	−0.0022 (3)	−0.0064 (3)
O1	0.0385 (9)	0.0443 (10)	0.0356 (9)	−0.0182 (8)	−0.0059 (7)	−0.0078 (8)
O2	0.0436 (11)	0.0429 (11)	0.114 (2)	−0.0170 (9)	−0.0113 (12)	−0.0243 (12)
O3	0.0443 (12)	0.0509 (12)	0.0865 (16)	−0.0157 (10)	−0.0153 (11)	−0.0066 (11)
O4	0.0607 (13)	0.0705 (14)	0.0457 (11)	−0.0259 (11)	0.0001 (10)	−0.0262 (10)
C1	0.0360 (12)	0.0366 (12)	0.0339 (12)	−0.0145 (10)	−0.0016 (10)	−0.0087 (10)
C2	0.0341 (12)	0.0333 (12)	0.0356 (12)	−0.0117 (10)	−0.0021 (10)	−0.0102 (10)
C3	0.0394 (13)	0.0395 (13)	0.0412 (14)	−0.0160 (11)	−0.0047 (10)	−0.0123 (11)
C4	0.0376 (13)	0.0365 (13)	0.0513 (16)	−0.0157 (11)	−0.0002 (11)	−0.0137 (11)
C5	0.0430 (14)	0.0394 (14)	0.0465 (15)	−0.0165 (12)	0.0019 (12)	−0.0049 (12)
C6	0.0429 (14)	0.0438 (14)	0.0348 (13)	−0.0143 (12)	−0.0048 (11)	−0.0060 (11)
C7	0.0335 (12)	0.0342 (12)	0.0409 (14)	−0.0108 (10)	−0.0047 (10)	−0.0097 (10)
C8	0.0340 (12)	0.0382 (13)	0.0373 (13)	−0.0142 (10)	−0.0016 (10)	−0.0084 (10)
C9	0.0366 (13)	0.0446 (14)	0.0449 (14)	−0.0186 (11)	−0.0029 (11)	−0.0123 (11)
C10	0.0401 (14)	0.0463 (15)	0.0491 (15)	−0.0210 (12)	−0.0001 (12)	−0.0089 (12)
C11	0.055 (2)	0.0450 (19)	0.158 (4)	−0.0120 (16)	−0.004 (2)	−0.039 (2)
C12	0.075 (3)	0.047 (2)	0.151 (4)	−0.0233 (18)	−0.005 (3)	−0.032 (2)
C13	0.138 (5)	0.095 (4)	0.140 (5)	−0.073 (4)	0.050 (4)	−0.026 (3)
C14	0.0550 (18)	0.0543 (18)	0.0555 (18)	−0.0142 (15)	−0.0160 (14)	−0.0075 (14)

Geometric parameters (Å, º) top

Br—C4	1.899 (3)	C6—C7	1.374 (4)
S—O4	1.492 (2)	C6—H6	0.9300
S—C1	1.763 (3)	C8—C9	1.486 (4)
S—C14	1.790 (3)	C9—C10	1.509 (4)
O1—C8	1.375 (3)	C9—H9A	0.9700
O1—C7	1.375 (3)	C9—H9B	0.9700
O2—C10	1.323 (4)	C11—C12	1.494 (6)
O2—C11	1.465 (4)	C11—H11A	0.9700
O3—C10	1.202 (4)	C11—H11B	0.9700
C1—C8	1.349 (4)	C12—C13	1.465 (7)
C1—C2	1.448 (4)	C12—H12A	0.9700
C2—C3	1.396 (4)	C12—H12B	0.9700
C2—C7	1.397 (3)	C13—H13A	0.9600
C3—C4	1.376 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.402 (4)	C14—H14A	0.9600
C5—C6	1.377 (4)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600

O4—S—C1	107.01 (13)	C10—C9—H9A	109.2
O4—S—C14	106.32 (14)	C8—C9—H9B	109.2
C1—S—C14	98.46 (14)	C10—C9—H9B	109.2
C8—O1—C7	106.53 (19)	H9A—C9—H9B	107.9
C10—O2—C11	117.2 (2)	O3—C10—O2	124.0 (3)
C8—C1—C2	107.4 (2)	O3—C10—C9	125.6 (3)
C8—C1—S	123.4 (2)	O2—C10—C9	110.4 (2)
C2—C1—S	129.00 (19)	O2—C11—C12	107.7 (3)
C3—C2—C7	119.3 (2)	O2—C11—H11A	110.2
C3—C2—C1	136.1 (2)	C12—C11—H11A	110.2
C7—C2—C1	104.6 (2)	O2—C11—H11B	110.2
C4—C3—C2	116.8 (2)	C12—C11—H11B	110.2
C4—C3—H3	121.6	H11A—C11—H11B	108.5
C2—C3—H3	121.6	C13—C12—C11	114.4 (5)
C3—C4—C5	123.3 (3)	C13—C12—H12A	108.7
C3—C4—Br	118.7 (2)	C11—C12—H12A	108.7
C5—C4—Br	117.9 (2)	C13—C12—H12B	108.7
C6—C5—C4	119.8 (3)	C11—C12—H12B	108.7
C6—C5—H5	120.1	H12A—C12—H12B	107.6
C4—C5—H5	120.1	C12—C13—H13A	109.5
C7—C6—C5	117.1 (2)	C12—C13—H13B	109.5
C7—C6—H6	121.5	H13A—C13—H13B	109.5
C5—C6—H6	121.5	C12—C13—H13C	109.5
O1—C7—C6	125.9 (2)	H13A—C13—H13C	109.5
O1—C7—C2	110.5 (2)	H13B—C13—H13C	109.5
C6—C7—C2	123.6 (2)	S—C14—H14A	109.5
C1—C8—O1	111.0 (2)	S—C14—H14B	109.5
C1—C8—C9	133.2 (2)	H14A—C14—H14B	109.5
O1—C8—C9	115.7 (2)	S—C14—H14C	109.5
C8—C9—C10	112.2 (2)	H14A—C14—H14C	109.5
C8—C9—H9A	109.2	H14B—C14—H14C	109.5

O4—S—C1—C8	−134.5 (2)	C3—C2—C7—O1	178.3 (2)
C14—S—C1—C8	115.5 (2)	C1—C2—C7—O1	−1.2 (3)
O4—S—C1—C2	40.5 (3)	C3—C2—C7—C6	−1.8 (4)
C14—S—C1—C2	−69.5 (3)	C1—C2—C7—C6	178.8 (2)
C8—C1—C2—C3	−178.6 (3)	C2—C1—C8—O1	0.0 (3)
S—C1—C2—C3	5.7 (4)	S—C1—C8—O1	175.96 (17)
C8—C1—C2—C7	0.7 (3)	C2—C1—C8—C9	175.7 (3)
S—C1—C2—C7	−174.95 (19)	S—C1—C8—C9	−8.3 (4)
C7—C2—C3—C4	1.3 (4)	C7—O1—C8—C1	−0.7 (3)
C1—C2—C3—C4	−179.5 (3)	C7—O1—C8—C9	−177.3 (2)
C2—C3—C4—C5	0.6 (4)	C1—C8—C9—C10	−73.6 (4)
C2—C3—C4—Br	179.65 (18)	O1—C8—C9—C10	102.0 (3)
C3—C4—C5—C6	−2.0 (4)	C11—O2—C10—O3	−1.5 (5)
Br—C4—C5—C6	178.9 (2)	C11—O2—C10—C9	179.2 (3)
C4—C5—C6—C7	1.5 (4)	C8—C9—C10—O3	24.7 (4)
C8—O1—C7—C6	−178.8 (2)	C8—C9—C10—O2	−156.0 (2)
C8—O1—C7—C2	1.2 (3)	C10—O2—C11—C12	166.2 (4)
C5—C6—C7—O1	−179.7 (2)	O2—C11—C12—C13	−62.0 (6)
C5—C6—C7—C2	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1ⁱ	0.97	3.02	3.720 (3)	130
C12—H12B···Cg2ⁱ	0.97	2.90	3.826 (3)	161
C3—H3···O4ⁱⁱ	0.93	2.54	3.424 (3)	159
C5—H5···O3ⁱⁱⁱ	0.93	2.58	3.430 (4)	152
C9—H9B···O4^iv	0.97	2.37	3.321 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅BrO₄S
M_r	359.23
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.4538 (6), 9.8823 (7), 10.3231 (7)
α, β, γ (°)	72.358 (1), 81.200 (1), 65.443 (1)
V (Å³)	747.16 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.90
Crystal size (mm)	0.60 × 0.50 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.187, 0.556
No. of measured, independent and observed [I > 2σ(I)] reflections	3932, 2593, 2359
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.07
No. of reflections	2593
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.38

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
C11—H11B···Cg1ⁱ	0.97	3.02	3.720 (3)	130.0
C12—H12B···Cg2ⁱ	0.97	2.90	3.826 (3)	161.1
C3—H3···O4ⁱⁱ	0.93	2.54	3.424 (3)	158.7
C5—H5···O3ⁱⁱⁱ	0.93	2.58	3.430 (4)	152.1
C9—H9B···O4^iv	0.97	2.37	3.321 (3)	167.1

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+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. (2008a). Acta Cryst. E64, o2250. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2397. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 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 65| Part 3| March 2009| Page o520

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