7-Bromo-1-methyl­sulfinyl-2-phenyl­naphtho[2,1-b]furan

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

doi:10.1107/S1600536809028165

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1956

doi:10.1107/S1600536809028165

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7-Bromo-1-methylsulfinyl-2-phenylnaphtho[2,1-b]furan

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 July 2009; accepted 17 July 2009; online 22 July 2009)

In the title compound, C₁₉H₁₃BrO₂S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran unit. The phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 42.2 (1)°. The crystal structure is stabilized by two intermolecular C—H⋯π interactions, and by non-classical intermolecular C—H⋯O and C—H⋯Br hydrogen bonds.

Related literature

For the crystal structures of similar 2-phenylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2009a ,b ). For details of the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ); Hagiwara et al. (1999 ); Piloto et al. (2005 ).

Experimental

Crystal data

C₁₉H₁₃BrO₂S
M_r = 385.26
Monoclinic, P 2₁ /c
a = 6.0007 (4) Å
b = 22.699 (2) Å
c = 11.2151 (8) Å
β = 91.267 (1)°
V = 1527.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.84 mm⁻¹
T = 273 K
0.25 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.538, T_max = 0.765
13412 measured reflections
3476 independent reflections
2280 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.091
S = 1.09
3476 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg1ⁱ	0.93	2.70	3.377 (4)	131
C19—H19B⋯Cg2ⁱⁱ	0.96	2.99	3.497 (4)	114
C18—H18⋯O2ⁱⁱⁱ	0.93	2.54	3.283 (4)	137
C16—H16⋯Br^iv	0.93	2.97	3.823 (4)	153
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x-2, y, z-1. Cg1 and Cg2 are the centroids of the C2/C3/C8–C11 benzene and C13–C18 benzene rings, 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/S1600536809028165/rk2156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028165/rk2156Isup2.hkl

checkCIF report

Comment top

Molecules containing naphthofuran skeleton have attracted considerable interest in view of their biological and pharmacological activities (Goel & Dixit, 2004; Hagiwara et al., 1999; Piloto et al., 2005). This work is related to our communications on the synthesis and structures of 2-phenylnaphtho[2,1-b]furan analogues, viz. 2-phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2009a) and 7-bromo-2-phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2009b). Now we present the crystal structure of the title compound (I) (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.045 (3)Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle in I formed by the plane of the naphthofuran ring and the plane of 2-phenyl ring is 42.2 (1)°. The molecular packing (Fig. 2) is stabilized by two intermolecular C–H···π interactions; the first between an H atom of the 2-phenyl ring and the central benzene ring of the naphthofuran fragment (C14–H14···Cg1ⁱ), the second between the methyl H atom of the methylsulfinyl substituent and the phenyl ring (C19–H19B···Cg2ⁱⁱ), respectively (Table 1 and Fig. 2; Cg1 and Cg2 are the centroids of the C2/C3/C8/C9/C10/C11 benzene and C13-C18 benzene rings). Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z. In addition, weak non-classical intermolecular C–H···O and C–H···Br hydrogen bonds in the structure were observed (Table 1 and Fig. 3).

Related literature top

For the crystal structures of similar 2-phenylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2009a,b). For details of the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004); Hagiwara et al. (1999); Piloto et al. (2005). Cg1 and Cg2 are the centroids of the C2/C3/C8–C11 benzene and C13–C18 benzene rings, respectively.

Experimental top

The 77% 3-chloroperoxybenzoic acid (157 mg, 0.7 mmol) was added in small portions to a stirred solution of 7-bromo-1-methylsulfanyl-2-phenylnaphtho[2,1-b]furan (258 mg, 0.7 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 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 78%, m.p. 503-504 K; R_f = 0.72 (hexane-ethyl acetate, 1 : 2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in dichloromethane at room temperature.

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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The C–H···π interactions (dotted lines) in the crystal structure of title compound. Cg denotes the ring centroids. Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.
	Fig. 3. The C–H···O and C–H···Br interactions (dotted lines) in the title compound. Symmetry codes: (iii) x, -y+3/2, z-1/2; (iv) x-2, y, z-1; (v) x, -y+3/2, z+1/2; (vi) x+2, y, z+1.

7-Bromo-1-methylsulfinyl-2-phenylnaphtho[2,1-b]furan top

Crystal data top

C₁₉H₁₃BrO₂S	F(000) = 776
M_r = 385.26	D_x = 1.676 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3117 reflections
a = 6.0007 (4) Å	θ = 2.6–27.3°
b = 22.699 (2) Å	µ = 2.84 mm⁻¹
c = 11.2151 (8) Å	T = 273 K
β = 91.267 (1)°	Block, colourless
V = 1527.2 (2) Å³	0.25 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3476 independent reflections
Radiation source: fine-focus sealed tube	2280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.8°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −29→29
T_min = 0.538, T_max = 0.765	l = −14→14
13412 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.091	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0234P)² + 2.3626P] where P = (F_o² + 2F_c²)/3
3476 reflections	(Δ/σ)_max = 0.002
209 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₉H₁₃BrO₂S	V = 1527.2 (2) Å³
M_r = 385.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0007 (4) Å	µ = 2.84 mm⁻¹
b = 22.699 (2) Å	T = 273 K
c = 11.2151 (8) Å	0.25 × 0.12 × 0.10 mm
β = 91.267 (1)°

Data collection top

Bruker SMART CCD diffractometer	3476 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2280 reflections with I > 2σ(I)
T_min = 0.538, T_max = 0.765	R_int = 0.056
13412 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.09	Δρ_max = 0.56 e Å⁻³
3476 reflections	Δρ_min = −0.49 e Å⁻³
209 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.04085 (7)	0.614541 (18)	1.06514 (4)	0.03289 (13)
S	0.04668 (16)	0.71912 (4)	0.66608 (8)	0.0231 (2)
O1	−0.0349 (4)	0.54760 (10)	0.6267 (2)	0.0208 (5)
O2	0.0802 (4)	0.74221 (11)	0.7894 (2)	0.0316 (7)
C1	0.0664 (6)	0.64129 (15)	0.6686 (3)	0.0191 (7)
C2	0.2146 (6)	0.60190 (15)	0.7355 (3)	0.0195 (8)
C3	0.4067 (6)	0.60777 (15)	0.8130 (3)	0.0194 (7)
C4	0.4927 (6)	0.66186 (16)	0.8559 (3)	0.0234 (8)
H4	0.4210	0.6967	0.8343	0.028*
C5	0.6794 (6)	0.66431 (17)	0.9287 (3)	0.0255 (9)
H5	0.7343	0.7003	0.9560	0.031*
C6	0.7857 (6)	0.61148 (17)	0.9610 (3)	0.0243 (8)
C7	0.7101 (6)	0.55824 (16)	0.9228 (3)	0.0237 (8)
H7	0.7854	0.5241	0.9455	0.028*
C8	0.5162 (6)	0.55461 (16)	0.8484 (3)	0.0210 (8)
C9	0.4331 (6)	0.49849 (16)	0.8115 (3)	0.0230 (8)
H9	0.5084	0.4646	0.8357	0.028*
C10	0.2455 (6)	0.49362 (15)	0.7415 (3)	0.0233 (8)
H10	0.1883	0.4571	0.7193	0.028*
C11	0.1437 (6)	0.54571 (15)	0.7050 (3)	0.0196 (8)
C12	−0.0772 (6)	0.60640 (15)	0.6050 (3)	0.0199 (8)
C13	−0.2527 (6)	0.61732 (16)	0.5143 (3)	0.0206 (7)
C14	−0.4437 (6)	0.58201 (15)	0.5112 (3)	0.0226 (8)
H14	−0.4595	0.5521	0.5671	0.027*
C15	−0.6085 (6)	0.59122 (17)	0.4259 (3)	0.0273 (9)
H15	−0.7349	0.5675	0.4241	0.033*
C16	−0.5855 (7)	0.63605 (17)	0.3422 (3)	0.0286 (9)
H16	−0.6985	0.6430	0.2859	0.034*
C17	−0.3945 (7)	0.67033 (16)	0.3429 (3)	0.0284 (9)
H17	−0.3785	0.6998	0.2861	0.034*
C18	−0.2277 (6)	0.66085 (15)	0.4275 (3)	0.0229 (8)
H18	−0.0985	0.6835	0.4267	0.028*
C19	0.2979 (7)	0.73401 (16)	0.5874 (3)	0.0284 (9)
H19A	0.3314	0.7753	0.5921	0.043*
H19B	0.2779	0.7228	0.5053	0.043*
H19C	0.4187	0.7119	0.6226	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0306 (2)	0.0375 (2)	0.0302 (2)	−0.0047 (2)	−0.00788 (15)	0.0030 (2)
S	0.0258 (5)	0.0177 (5)	0.0260 (5)	0.0017 (4)	0.0018 (4)	−0.0027 (4)
O1	0.0258 (14)	0.0156 (12)	0.0210 (13)	−0.0033 (10)	0.0000 (11)	0.0003 (10)
O2	0.0401 (17)	0.0287 (15)	0.0262 (15)	0.0017 (13)	0.0037 (12)	−0.0113 (12)
C1	0.0228 (19)	0.0155 (17)	0.0191 (18)	−0.0026 (15)	0.0037 (14)	−0.0009 (14)
C2	0.0244 (19)	0.0190 (19)	0.0154 (17)	−0.0003 (15)	0.0047 (14)	0.0001 (14)
C3	0.0215 (18)	0.0202 (18)	0.0168 (17)	−0.0005 (15)	0.0030 (14)	0.0011 (15)
C4	0.028 (2)	0.0196 (19)	0.022 (2)	−0.0003 (16)	0.0027 (16)	0.0015 (15)
C5	0.028 (2)	0.026 (2)	0.022 (2)	−0.0066 (17)	0.0003 (16)	−0.0022 (16)
C6	0.0241 (19)	0.031 (2)	0.0177 (17)	−0.0044 (18)	−0.0007 (14)	0.0000 (17)
C7	0.027 (2)	0.025 (2)	0.0191 (18)	0.0043 (17)	0.0010 (15)	0.0022 (16)
C8	0.026 (2)	0.0229 (19)	0.0148 (17)	0.0037 (16)	0.0037 (15)	0.0005 (15)
C9	0.030 (2)	0.0195 (19)	0.0193 (19)	0.0040 (16)	0.0005 (16)	0.0020 (15)
C10	0.036 (2)	0.0162 (18)	0.0184 (19)	−0.0054 (16)	0.0037 (16)	−0.0006 (15)
C11	0.0215 (19)	0.0195 (18)	0.0178 (18)	−0.0020 (15)	0.0018 (15)	−0.0009 (14)
C12	0.0227 (19)	0.0163 (19)	0.0210 (18)	−0.0006 (15)	0.0060 (14)	−0.0019 (14)
C13	0.0211 (18)	0.0220 (18)	0.0188 (17)	0.0031 (16)	0.0041 (14)	−0.0055 (16)
C14	0.026 (2)	0.0186 (19)	0.0236 (19)	0.0014 (16)	0.0055 (16)	−0.0032 (15)
C15	0.021 (2)	0.032 (2)	0.029 (2)	0.0007 (16)	−0.0001 (16)	−0.0096 (17)
C16	0.032 (2)	0.030 (2)	0.024 (2)	0.0073 (18)	−0.0055 (17)	−0.0074 (17)
C17	0.040 (2)	0.023 (2)	0.022 (2)	0.0049 (18)	0.0018 (18)	0.0003 (16)
C18	0.023 (2)	0.0210 (19)	0.025 (2)	−0.0013 (16)	0.0005 (16)	−0.0022 (15)
C19	0.037 (2)	0.022 (2)	0.026 (2)	−0.0037 (18)	0.0034 (17)	−0.0001 (16)

Geometric parameters (Å, º) top

Br—C6	1.906 (3)	C9—C10	1.362 (5)
S—O2	1.489 (3)	C9—H9	0.9300
S—C1	1.771 (3)	C10—C11	1.389 (5)
S—C19	1.796 (4)	C10—H10	0.9300
O1—C11	1.371 (4)	C12—C13	1.469 (5)
O1—C12	1.379 (4)	C13—C18	1.398 (5)
C1—C12	1.360 (5)	C13—C14	1.398 (5)
C1—C2	1.457 (5)	C14—C15	1.377 (5)
C2—C11	1.385 (5)	C14—H14	0.9300
C2—C3	1.434 (5)	C15—C16	1.393 (5)
C3—C4	1.412 (5)	C15—H15	0.9300
C3—C8	1.426 (5)	C16—C17	1.385 (5)
C4—C5	1.373 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.381 (5)
C5—C6	1.402 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.357 (5)	C19—H19A	0.9600
C7—C8	1.420 (5)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—C9	1.426 (5)

O2—S—C1	109.20 (16)	C9—C10—H10	121.5
O2—S—C19	107.03 (17)	C11—C10—H10	121.5
C1—S—C19	97.99 (17)	O1—C11—C2	111.2 (3)
C11—O1—C12	106.3 (3)	O1—C11—C10	123.2 (3)
C12—C1—C2	106.6 (3)	C2—C11—C10	125.5 (3)
C12—C1—S	122.1 (3)	C1—C12—O1	111.1 (3)
C2—C1—S	131.3 (3)	C1—C12—C13	134.5 (3)
C11—C2—C3	118.3 (3)	O1—C12—C13	114.3 (3)
C11—C2—C1	104.9 (3)	C18—C13—C14	119.2 (3)
C3—C2—C1	136.7 (3)	C18—C13—C12	121.0 (3)
C4—C3—C8	118.6 (3)	C14—C13—C12	119.7 (3)
C4—C3—C2	124.8 (3)	C15—C14—C13	120.4 (3)
C8—C3—C2	116.7 (3)	C15—C14—H14	119.8
C5—C4—C3	121.7 (3)	C13—C14—H14	119.8
C5—C4—H4	119.2	C14—C15—C16	119.9 (4)
C3—C4—H4	119.2	C14—C15—H15	120.0
C4—C5—C6	118.7 (3)	C16—C15—H15	120.0
C4—C5—H5	120.7	C17—C16—C15	120.1 (4)
C6—C5—H5	120.7	C17—C16—H16	120.0
C7—C6—C5	122.2 (3)	C15—C16—H16	120.0
C7—C6—Br	119.0 (3)	C18—C17—C16	120.2 (4)
C5—C6—Br	118.8 (3)	C18—C17—H17	119.9
C6—C7—C8	120.1 (3)	C16—C17—H17	119.9
C6—C7—H7	120.0	C17—C18—C13	120.1 (3)
C8—C7—H7	120.0	C17—C18—H18	119.9
C7—C8—C9	119.9 (3)	C13—C18—H18	119.9
C7—C8—C3	118.8 (3)	S—C19—H19A	109.5
C9—C8—C3	121.3 (3)	S—C19—H19B	109.5
C10—C9—C8	121.2 (3)	H19A—C19—H19B	109.5
C10—C9—H9	119.4	S—C19—H19C	109.5
C8—C9—H9	119.4	H19A—C19—H19C	109.5
C9—C10—C11	117.0 (3)	H19B—C19—H19C	109.5

O2—S—C1—C12	137.3 (3)	C8—C9—C10—C11	1.9 (5)
C19—S—C1—C12	−111.5 (3)	C12—O1—C11—C2	1.0 (4)
O2—S—C1—C2	−39.4 (4)	C12—O1—C11—C10	−175.3 (3)
C19—S—C1—C2	71.8 (4)	C3—C2—C11—O1	−177.3 (3)
C12—C1—C2—C11	−0.1 (4)	C1—C2—C11—O1	−0.6 (4)
S—C1—C2—C11	177.1 (3)	C3—C2—C11—C10	−1.1 (5)
C12—C1—C2—C3	175.8 (4)	C1—C2—C11—C10	175.6 (3)
S—C1—C2—C3	−7.1 (6)	C9—C10—C11—O1	174.5 (3)
C11—C2—C3—C4	−177.2 (3)	C9—C10—C11—C2	−1.3 (5)
C1—C2—C3—C4	7.4 (7)	C2—C1—C12—O1	0.7 (4)
C11—C2—C3—C8	2.7 (5)	S—C1—C12—O1	−176.8 (2)
C1—C2—C3—C8	−172.7 (4)	C2—C1—C12—C13	−174.3 (4)
C8—C3—C4—C5	1.0 (5)	S—C1—C12—C13	8.3 (6)
C2—C3—C4—C5	−179.1 (3)	C11—O1—C12—C1	−1.0 (4)
C3—C4—C5—C6	−0.2 (6)	C11—O1—C12—C13	175.0 (3)
C4—C5—C6—C7	0.0 (6)	C1—C12—C13—C18	37.7 (6)
C4—C5—C6—Br	−178.5 (3)	O1—C12—C13—C18	−137.1 (3)
C5—C6—C7—C8	−0.5 (5)	C1—C12—C13—C14	−145.2 (4)
Br—C6—C7—C8	178.0 (3)	O1—C12—C13—C14	40.0 (4)
C6—C7—C8—C9	−178.0 (3)	C18—C13—C14—C15	−2.0 (5)
C6—C7—C8—C3	1.3 (5)	C12—C13—C14—C15	−179.2 (3)
C4—C3—C8—C7	−1.5 (5)	C13—C14—C15—C16	−0.2 (5)
C2—C3—C8—C7	178.6 (3)	C14—C15—C16—C17	1.7 (6)
C4—C3—C8—C9	177.8 (3)	C15—C16—C17—C18	−1.0 (6)
C2—C3—C8—C9	−2.1 (5)	C16—C17—C18—C13	−1.2 (6)
C7—C8—C9—C10	179.0 (3)	C14—C13—C18—C17	2.7 (5)
C3—C8—C9—C10	−0.3 (5)	C12—C13—C18—C17	179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg1ⁱ	0.93	2.70	3.377 (4)	131
C19—H19B···Cg2ⁱⁱ	0.96	2.99	3.497 (4)	114
C18—H18···O2ⁱⁱⁱ	0.93	2.54	3.283 (4)	137
C16—H16···Br^iv	0.93	2.97	3.823 (4)	153

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, −y+3/2, z−1/2; (iv) x−2, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃BrO₂S
M_r	385.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	6.0007 (4), 22.699 (2), 11.2151 (8)
β (°)	91.267 (1)
V (Å³)	1527.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.84
Crystal size (mm)	0.25 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.538, 0.765
No. of measured, independent and observed [I > 2σ(I)] reflections	13412, 3476, 2280
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.091, 1.09
No. of reflections	3476
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.49

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···Cg1ⁱ	0.93	2.70	3.377 (4)	130.8
C19—H19B···Cg2ⁱⁱ	0.96	2.99	3.497 (4)	114.2
C18—H18···O2ⁱⁱⁱ	0.93	2.54	3.283 (4)	137.4
C16—H16···Br^iv	0.93	2.97	3.823 (4)	153.2

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, −y+3/2, z−1/2; (iv) x−2, y, z−1.

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. (2009a). Acta Cryst. E65, o1443. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1812. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Goel, A. & Dixit, M. (2004). Tetrahedron Lett. 45, 8819–8821. Web of Science CrossRef CAS Google Scholar
Hagiwara, H., Sato, K., Suzuki, T. & Ando, M. (1999). Heterocycles, 51, 497–500. CrossRef CAS Google Scholar
Piloto, A. M., Costa, S. P. G. & Goncalves, M. S. T. (2005). Tetrahedron Lett. 46, 4757–4760. Web of Science CrossRef CAS 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 8| August 2009| Page o1956

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