1-(4-Bromo­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan

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

doi:10.1107/S160053681202939X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2324

https://doi.org/10.1107/S160053681202939X

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1-(4-Bromophenylsulfonyl)-2-methylnaphtho[2,1-b]furan

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 25 June 2012; accepted 28 June 2012; online 4 July 2012)

In the title compound, C₁₉H₁₃BrO₃S, the 4-bromophenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphthofuran ring. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits slipped π–π interactions between the central naphthofuran benzene rings of neighbouring molecules [centroid–centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphthofuran benzene ring and the furan ring of neighbouring molecules [centroid–centroid distance = 3.655 (2), slippage = 1.136 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 , 2012 ).

Experimental

Crystal data

C₁₉H₁₃BrO₃S
M_r = 401.26
Triclinic, $[P \overline 1]$
a = 6.9579 (2) Å
b = 10.9709 (4) Å
c = 11.4207 (4) Å
α = 110.510 (2)°
β = 105.886 (2)°
γ = 91.656 (2)°
V = 777.77 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.79 mm⁻¹
T = 173 K
0.29 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.555, T_max = 0.746
14423 measured reflections
3876 independent reflections
3201 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.05
3876 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 4-bromophenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2ⁱ	0.95	2.49	3.197 (2)	131
C19—H19⋯O3ⁱⁱ	0.95	2.47	3.177 (2)	132
C9—H9⋯Cg1ⁱⁱⁱ	0.95	2.96	3.782 (2)	120
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x-1, -y-1, -z-1.

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/S160053681202939X/ff2074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202939X/ff2074Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202939X/ff2074Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfonyl (Choi et al., 2008) and 1-(4-methylphenylsulfonyl) (Choi et al., 2012) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the naphthofuran ring is 64.11 (2)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C14–C19 4-bromophenyl ring). In the crystal structure (Fig. 3), molecules are connected π–π interactions; the first one between the central naphthofuran benzene rings of neighbouring molecules, with a Cg2···Cg2ⁱⁱ distance of 3.559 (2) Å and an interplanar distance of 3.405 (2) Å resulting in a slippage of 1.036 (2) Å (Cg2 is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring), and the second one between the central naphthofuran benzene ring and the furan ring of neighbouring molecules, with a Cg2···Cg3ⁱ distance of 3.655 (2) Å and an interplanar distance of 3.474 (2) Å resulting in a slippage of 1.136 (2) Å (Cg3 is the centroid of the C1/C2/C11/O1/C12 furan ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 1-(4-bromophenylsulfanyl)-2-methylnaphtho [2,1-b]furan (332 mg, 0.9 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 71%, m.p. 452–453 K; R_f = 0.69 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Structure description top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2012).

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 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 non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z + 2; (ii) - x + 1, - y + 2, - z + 2; (iii) - x + 1, - y + 1, - z + 1.]
	Fig. 3. A view of the π–π interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. [Symmetry codes: (i) - x , - y + 1, - z + 1; (ii)- x + 1, - y + 1, - z + 1.]

1-(4-Bromophenylsulfonyl)-2-methylnaphtho[2,1-b]furan top

Crystal data top

C₁₉H₁₃BrO₃S	Z = 2
M_r = 401.26	F(000) = 404
Triclinic, P1	D_x = 1.713 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9579 (2) Å	Cell parameters from 6011 reflections
b = 10.9709 (4) Å	θ = 2.2–27.9°
c = 11.4207 (4) Å	µ = 2.79 mm⁻¹
α = 110.510 (2)°	T = 173 K
β = 105.886 (2)°	Block, colourless
γ = 91.656 (2)°	0.29 × 0.13 × 0.10 mm
V = 777.77 (5) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3876 independent reflections
Radiation source: rotating anode	3201 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.036
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
φ and ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.555, T_max = 0.746	l = −15→15
14423 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0411P)² + 0.2709P] where P = (F_o² + 2F_c²)/3
3876 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₃BrO₃S	γ = 91.656 (2)°
M_r = 401.26	V = 777.77 (5) Å³
Triclinic, P1	Z = 2
a = 6.9579 (2) Å	Mo Kα radiation
b = 10.9709 (4) Å	µ = 2.79 mm⁻¹
c = 11.4207 (4) Å	T = 173 K
α = 110.510 (2)°	0.29 × 0.13 × 0.10 mm
β = 105.886 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3876 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3201 reflections with I > 2σ(I)
T_min = 0.555, T_max = 0.746	R_int = 0.036
14423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	Δρ_max = 0.49 e Å⁻³
3876 reflections	Δρ_min = −0.35 e Å⁻³
218 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
Br1	1.25056 (3)	0.78521 (2)	1.20765 (2)	0.04071 (10)
S1	0.33058 (8)	0.71206 (4)	0.86111 (5)	0.02364 (12)
O1	0.2860 (2)	0.71224 (15)	0.51468 (15)	0.0292 (3)
O2	0.2305 (2)	0.60540 (13)	0.87692 (14)	0.0279 (3)
O3	0.2685 (2)	0.83982 (14)	0.90608 (16)	0.0316 (3)
C1	0.3103 (3)	0.67109 (19)	0.6958 (2)	0.0239 (4)
C2	0.2740 (3)	0.54502 (19)	0.5872 (2)	0.0230 (4)
C3	0.2529 (3)	0.40719 (19)	0.5655 (2)	0.0237 (4)
C4	0.2678 (3)	0.3548 (2)	0.6634 (2)	0.0290 (4)
H4	0.2924	0.4128	0.7518	0.035*
C5	0.2476 (4)	0.2215 (2)	0.6336 (2)	0.0337 (5)
H5	0.2587	0.1886	0.7015	0.040*
C6	0.2108 (4)	0.1340 (2)	0.5044 (2)	0.0366 (5)
H6	0.1970	0.0419	0.4844	0.044*
C7	0.1949 (3)	0.1816 (2)	0.4076 (2)	0.0342 (5)
H7	0.1694	0.1215	0.3199	0.041*
C8	0.2153 (3)	0.3179 (2)	0.4338 (2)	0.0270 (4)
C9	0.1972 (3)	0.3626 (2)	0.3291 (2)	0.0321 (5)
H9	0.1690	0.3001	0.2422	0.038*
C10	0.2193 (3)	0.4924 (2)	0.3507 (2)	0.0310 (5)
H10	0.2082	0.5229	0.2812	0.037*
C11	0.2592 (3)	0.5787 (2)	0.4802 (2)	0.0270 (4)
C12	0.3190 (3)	0.7668 (2)	0.6459 (2)	0.0272 (4)
C13	0.3533 (4)	0.9123 (2)	0.6993 (2)	0.0350 (5)
H13A	0.4214	0.9430	0.6481	0.053*
H13B	0.4376	0.9444	0.7911	0.053*
H13C	0.2234	0.9458	0.6940	0.053*
C14	0.5890 (3)	0.72911 (18)	0.94600 (19)	0.0234 (4)
C15	0.6697 (3)	0.62392 (19)	0.9740 (2)	0.0274 (4)
H15	0.5888	0.5408	0.9405	0.033*
C16	0.8677 (3)	0.6410 (2)	1.0507 (2)	0.0284 (4)
H16	0.9231	0.5704	1.0717	0.034*
C17	0.9844 (3)	0.7619 (2)	1.0966 (2)	0.0280 (4)
C18	0.9081 (3)	0.8657 (2)	1.0663 (2)	0.0310 (5)
H18	0.9915	0.9474	1.0965	0.037*
C19	0.7094 (3)	0.84936 (19)	0.9916 (2)	0.0280 (4)
H19	0.6548	0.9205	0.9713	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03136 (14)	0.04733 (16)	0.03750 (15)	−0.00121 (10)	−0.00038 (10)	0.01757 (12)
S1	0.0257 (2)	0.0192 (2)	0.0267 (3)	0.00392 (18)	0.0099 (2)	0.00780 (19)
O1	0.0271 (8)	0.0331 (8)	0.0317 (8)	0.0034 (6)	0.0083 (7)	0.0178 (7)
O2	0.0308 (8)	0.0245 (7)	0.0309 (8)	0.0017 (6)	0.0122 (7)	0.0113 (6)
O3	0.0346 (8)	0.0241 (7)	0.0386 (9)	0.0103 (6)	0.0165 (7)	0.0102 (6)
C1	0.0223 (10)	0.0236 (9)	0.0261 (10)	0.0041 (8)	0.0067 (8)	0.0100 (8)
C2	0.0161 (9)	0.0265 (9)	0.0263 (10)	0.0037 (7)	0.0062 (8)	0.0101 (8)
C3	0.0161 (9)	0.0245 (9)	0.0269 (10)	0.0035 (7)	0.0041 (8)	0.0072 (8)
C4	0.0297 (11)	0.0254 (10)	0.0304 (11)	0.0052 (8)	0.0068 (9)	0.0100 (9)
C5	0.0369 (12)	0.0254 (10)	0.0367 (13)	0.0050 (9)	0.0075 (10)	0.0119 (10)
C6	0.0354 (12)	0.0223 (10)	0.0458 (14)	0.0048 (9)	0.0109 (11)	0.0064 (10)
C7	0.0295 (11)	0.0288 (11)	0.0328 (12)	0.0015 (9)	0.0077 (10)	−0.0007 (9)
C8	0.0176 (9)	0.0305 (10)	0.0292 (11)	0.0035 (8)	0.0067 (8)	0.0070 (9)
C9	0.0243 (10)	0.0408 (12)	0.0245 (11)	0.0016 (9)	0.0066 (9)	0.0050 (9)
C10	0.0241 (10)	0.0431 (12)	0.0275 (11)	0.0044 (9)	0.0077 (9)	0.0153 (10)
C11	0.0190 (9)	0.0314 (10)	0.0325 (11)	0.0056 (8)	0.0079 (8)	0.0139 (9)
C12	0.0233 (10)	0.0285 (10)	0.0319 (11)	0.0046 (8)	0.0088 (9)	0.0134 (9)
C13	0.0399 (13)	0.0276 (11)	0.0429 (14)	0.0050 (9)	0.0135 (11)	0.0186 (10)
C14	0.0263 (10)	0.0204 (9)	0.0231 (10)	0.0033 (7)	0.0085 (8)	0.0068 (8)
C15	0.0298 (11)	0.0200 (9)	0.0318 (11)	0.0026 (8)	0.0103 (9)	0.0084 (8)
C16	0.0311 (11)	0.0257 (10)	0.0304 (11)	0.0060 (8)	0.0101 (9)	0.0120 (9)
C17	0.0263 (10)	0.0319 (11)	0.0250 (11)	0.0020 (8)	0.0076 (9)	0.0100 (9)
C18	0.0335 (11)	0.0259 (10)	0.0287 (11)	−0.0037 (9)	0.0056 (9)	0.0079 (9)
C19	0.0344 (11)	0.0207 (9)	0.0278 (11)	0.0032 (8)	0.0080 (9)	0.0091 (8)

Geometric parameters (Å, º) top

Br1—C17	1.888 (2)	C7—H7	0.9500
S1—O2	1.4340 (14)	C8—C9	1.421 (3)
S1—O3	1.4376 (15)	C9—C10	1.354 (3)
S1—C1	1.744 (2)	C9—H9	0.9500
S1—C14	1.763 (2)	C10—C11	1.393 (3)
O1—C12	1.353 (3)	C10—H10	0.9500
O1—C11	1.370 (2)	C12—C13	1.482 (3)
C1—C12	1.366 (3)	C13—H13A	0.9800
C1—C2	1.457 (3)	C13—H13B	0.9800
C2—C11	1.375 (3)	C13—H13C	0.9800
C2—C3	1.440 (3)	C14—C19	1.389 (3)
C3—C4	1.407 (3)	C14—C15	1.396 (3)
C3—C8	1.424 (3)	C15—C16	1.382 (3)
C4—C5	1.374 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.383 (3)
C5—C6	1.396 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.381 (3)
C6—C7	1.360 (3)	C18—C19	1.380 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.413 (3)	C19—H19	0.9500

O2—S1—O3	118.77 (9)	C9—C10—C11	116.5 (2)
O2—S1—C1	109.36 (9)	C9—C10—H10	121.8
O3—S1—C1	107.02 (9)	C11—C10—H10	121.8
O2—S1—C14	107.25 (9)	O1—C11—C2	111.59 (18)
O3—S1—C14	106.85 (9)	O1—C11—C10	121.95 (19)
C1—S1—C14	107.03 (9)	C2—C11—C10	126.4 (2)
C12—O1—C11	107.05 (16)	O1—C12—C1	110.30 (18)
C12—C1—C2	107.19 (18)	O1—C12—C13	113.74 (18)
C12—C1—S1	120.68 (16)	C1—C12—C13	136.0 (2)
C2—C1—S1	132.06 (15)	C12—C13—H13A	109.5
C11—C2—C3	117.54 (19)	C12—C13—H13B	109.5
C11—C2—C1	103.83 (17)	H13A—C13—H13B	109.5
C3—C2—C1	138.62 (19)	C12—C13—H13C	109.5
C4—C3—C8	118.08 (19)	H13A—C13—H13C	109.5
C4—C3—C2	125.39 (19)	H13B—C13—H13C	109.5
C8—C3—C2	116.52 (19)	C19—C14—C15	120.02 (19)
C5—C4—C3	121.3 (2)	C19—C14—S1	119.99 (16)
C5—C4—H4	119.4	C15—C14—S1	119.88 (15)
C3—C4—H4	119.4	C16—C15—C14	119.82 (18)
C4—C5—C6	120.6 (2)	C16—C15—H15	120.1
C4—C5—H5	119.7	C14—C15—H15	120.1
C6—C5—H5	119.7	C15—C16—C17	119.3 (2)
C7—C6—C5	119.4 (2)	C15—C16—H16	120.4
C7—C6—H6	120.3	C17—C16—H16	120.4
C5—C6—H6	120.3	C18—C17—C16	121.5 (2)
C6—C7—C8	121.9 (2)	C18—C17—Br1	119.98 (16)
C6—C7—H7	119.1	C16—C17—Br1	118.51 (17)
C8—C7—H7	119.1	C19—C18—C17	119.25 (19)
C7—C8—C9	119.7 (2)	C19—C18—H18	120.4
C7—C8—C3	118.7 (2)	C17—C18—H18	120.4
C9—C8—C3	121.7 (2)	C18—C19—C14	120.12 (19)
C10—C9—C8	121.3 (2)	C18—C19—H19	119.9
C10—C9—H9	119.3	C14—C19—H19	119.9
C8—C9—H9	119.3

O2—S1—C1—C12	154.18 (16)	C12—O1—C11—C10	179.18 (19)
O3—S1—C1—C12	24.32 (19)	C3—C2—C11—O1	−178.77 (16)
C14—S1—C1—C12	−89.95 (18)	C1—C2—C11—O1	0.9 (2)
O2—S1—C1—C2	−22.4 (2)	C3—C2—C11—C10	2.2 (3)
O3—S1—C1—C2	−152.26 (19)	C1—C2—C11—C10	−178.2 (2)
C14—S1—C1—C2	93.5 (2)	C9—C10—C11—O1	179.53 (18)
C12—C1—C2—C11	−1.5 (2)	C9—C10—C11—C2	−1.5 (3)
S1—C1—C2—C11	175.45 (16)	C11—O1—C12—C1	−1.1 (2)
C12—C1—C2—C3	178.0 (2)	C11—O1—C12—C13	179.40 (17)
S1—C1—C2—C3	−5.0 (4)	C2—C1—C12—O1	1.6 (2)
C11—C2—C3—C4	178.58 (19)	S1—C1—C12—O1	−175.75 (14)
C1—C2—C3—C4	−0.9 (4)	C2—C1—C12—C13	−179.0 (2)
C11—C2—C3—C8	−0.9 (3)	S1—C1—C12—C13	3.7 (4)
C1—C2—C3—C8	179.6 (2)	O2—S1—C14—C19	−155.16 (16)
C8—C3—C4—C5	0.2 (3)	O3—S1—C14—C19	−26.80 (19)
C2—C3—C4—C5	−179.3 (2)	C1—S1—C14—C19	87.57 (18)
C3—C4—C5—C6	−0.2 (4)	O2—S1—C14—C15	21.08 (19)
C4—C5—C6—C7	0.0 (4)	O3—S1—C14—C15	149.44 (16)
C5—C6—C7—C8	0.2 (3)	C1—S1—C14—C15	−96.18 (17)
C6—C7—C8—C9	−179.9 (2)	C19—C14—C15—C16	2.1 (3)
C6—C7—C8—C3	−0.2 (3)	S1—C14—C15—C16	−174.17 (15)
C4—C3—C8—C7	0.0 (3)	C14—C15—C16—C17	−1.2 (3)
C2—C3—C8—C7	179.52 (18)	C15—C16—C17—C18	−0.7 (3)
C4—C3—C8—C9	179.72 (19)	C15—C16—C17—Br1	177.18 (15)
C2—C3—C8—C9	−0.7 (3)	C16—C17—C18—C19	1.8 (3)
C7—C8—C9—C10	−178.8 (2)	Br1—C17—C18—C19	−176.05 (16)
C3—C8—C9—C10	1.4 (3)	C17—C18—C19—C14	−1.0 (3)
C8—C9—C10—C11	−0.4 (3)	C15—C14—C19—C18	−1.0 (3)
C12—O1—C11—C2	0.1 (2)	S1—C14—C19—C18	175.27 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 4-bromophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2ⁱ	0.95	2.49	3.197 (2)	131
C19—H19···O3ⁱⁱ	0.95	2.47	3.177 (2)	132
C9—H9···Cg1ⁱⁱⁱ	0.95	2.96	3.782 (2)	120

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃BrO₃S
M_r	401.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.9579 (2), 10.9709 (4), 11.4207 (4)
α, β, γ (°)	110.510 (2), 105.886 (2), 91.656 (2)
V (Å³)	777.77 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.79
Crystal size (mm)	0.29 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.555, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14423, 3876, 3201
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.05
No. of reflections	3876
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.35

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

Cg1 is the centroid of the C14–C19 4-bromophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2ⁱ	0.95	2.49	3.197 (2)	130.8
C19—H19···O3ⁱⁱ	0.95	2.47	3.177 (2)	131.5
C9—H9···Cg1ⁱⁱⁱ	0.95	2.96	3.782 (2)	119.6

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

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1193. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o727. 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. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 8| August 2012| Page o2324

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