2-(4-Bromo-phen-yl)-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan.

In the title compound, C(24)H(15)BrO(2)S, the sulfinyl O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The phenyl ring is nearly perpendicular to the plane of the tricyclic naphthofuran system [81.77 (6)°] and is tilted slightly towards it. The 4-bromo-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 31.12 (4)°. In the crystal structure, non-classical inter-molecular C-H⋯O and C-H⋯Br hydrogen bonds are observed. The crystal structure also exhibits aromatic π-π inter-actions between the furan ring and the central benzene ring of the adjacent naphthofuran system [centroid-centroid distance = 3.768 (3) Å]. In addition, inter-molecular C-Br⋯π inter-actions [3.866 (2) Å] between the Br atom and the phenyl ring of the phenyl-sulfinyl substituent are present.

Related literature

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

Experimental

Crystal data

C24H15BrO2S

M = 447.33

Triclinic,

a = 9.2412 (5) Å

b = 10.3266 (6) Å

c = 10.7606 (6) Å

α = 71.424 (1)°

β = 77.933 (1)°

γ = 79.287 (1)°

V = 943.96 (9) Å3

Z = 2

Mo Kα radiation

μ = 2.31 mm−1

T = 273 K

0.50 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.392, T max = 0.724

8200 measured reflections

4057 independent reflections

3482 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.06

4057 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029250/im2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029250/im2130Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H15BrO2S	Z = 2
Mr = 447.33	F(000) = 452
Triclinic, P1	Dx = 1.574 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2412 (5) Å	Cell parameters from 4680 reflections
b = 10.3266 (6) Å	θ = 2.3–27.5°
c = 10.7606 (6) Å	µ = 2.31 mm−1
α = 71.424 (1)°	T = 273 K
β = 77.933 (1)°	Block, colorless
γ = 79.287 (1)°	0.50 × 0.20 × 0.15 mm
V = 943.96 (9) Å3

Bruker SMART CCD diffractometer	4057 independent reflections
Radiation source: fine-focus sealed tube	3482 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −13→12
Tmin = 0.392, Tmax = 0.724	l = −13→13
8200 measured reflections

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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.068	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0322P)2 + 0.4094P] where P = (Fo2 + 2Fc2)/3
4057 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br	1.42799 (2)	0.59150 (2)	0.28002 (2)	0.04232 (8)
S	0.86347 (5)	0.80600 (5)	0.75366 (4)	0.02428 (10)
O1	0.67887 (14)	0.76607 (13)	0.47329 (12)	0.0288 (3)
O2	0.81883 (15)	0.94123 (13)	0.78284 (13)	0.0311 (3)
C1	0.73992 (19)	0.78681 (18)	0.65760 (17)	0.0242 (4)
C2	0.57973 (19)	0.82284 (18)	0.66420 (17)	0.0246 (4)
C3	0.45921 (19)	0.86444 (18)	0.75651 (18)	0.0256 (4)
C4	0.4754 (2)	0.88062 (19)	0.87792 (19)	0.0290 (4)
H4	0.5700	0.8656	0.9009	0.035*
C5	0.3534 (2)	0.9183 (2)	0.9630 (2)	0.0328 (4)
H5	0.3659	0.9284	1.0428	0.039*
C6	0.2097 (2)	0.9413 (2)	0.9292 (2)	0.0350 (4)
H6	0.1275	0.9660	0.9873	0.042*
C7	0.1900 (2)	0.92773 (19)	0.8119 (2)	0.0342 (4)
H7	0.0943	0.9434	0.7912	0.041*
C8	0.3132 (2)	0.89007 (18)	0.7210 (2)	0.0293 (4)
C9	0.2929 (2)	0.8767 (2)	0.5981 (2)	0.0334 (4)
H9	0.1972	0.8955	0.5768	0.040*
C10	0.4087 (2)	0.83736 (19)	0.5108 (2)	0.0330 (4)
H10	0.3946	0.8296	0.4306	0.040*
C11	0.5507 (2)	0.80912 (18)	0.54840 (18)	0.0277 (4)
C12	0.7932 (2)	0.75313 (18)	0.54145 (18)	0.0262 (4)
C13	0.9424 (2)	0.70872 (18)	0.47959 (17)	0.0259 (4)
C14	0.9808 (2)	0.74611 (19)	0.34116 (18)	0.0306 (4)
H14	0.9093	0.7958	0.2886	0.037*
C15	1.1239 (2)	0.7101 (2)	0.28158 (19)	0.0333 (4)
H15	1.1488	0.7356	0.1895	0.040*
C16	1.2295 (2)	0.6357 (2)	0.36050 (19)	0.0298 (4)
C17	1.1936 (2)	0.5935 (2)	0.49761 (19)	0.0306 (4)
H17	1.2651	0.5419	0.5494	0.037*
C18	1.0501 (2)	0.62905 (19)	0.55646 (18)	0.0287 (4)
H18	1.0248	0.5996	0.6484	0.034*
C19	0.81395 (18)	0.67454 (18)	0.90586 (17)	0.0234 (3)
C24	0.8333 (2)	0.6950 (2)	1.0216 (2)	0.0345 (4)
H24	0.8639	0.7766	1.0198	0.041*
C20	0.7690 (2)	0.5535 (2)	0.90810 (19)	0.0350 (4)
H20	0.7560	0.5403	0.8298	0.042*
C21	0.7434 (3)	0.4515 (2)	1.0279 (2)	0.0379 (5)
H21	0.7124	0.3700	1.0300	0.045*
C22	0.7637 (2)	0.4706 (2)	1.1437 (2)	0.0342 (4)
H22	0.7485	0.4015	1.2236	0.041*
C23	0.8065 (3)	0.5924 (2)	1.1409 (2)	0.0408 (5)
H23	0.8176	0.6061	1.2196	0.049*

	U11	U22	U33	U12	U13	U23
Br	0.03273 (12)	0.05681 (15)	0.04193 (13)	−0.00596 (9)	0.00269 (9)	−0.02602 (11)
S	0.0218 (2)	0.0270 (2)	0.0262 (2)	−0.00630 (17)	−0.00274 (16)	−0.00963 (17)
O1	0.0327 (7)	0.0293 (7)	0.0271 (6)	−0.0064 (5)	−0.0082 (5)	−0.0083 (5)
O2	0.0335 (7)	0.0263 (7)	0.0368 (7)	−0.0081 (5)	−0.0050 (6)	−0.0117 (6)
C1	0.0242 (9)	0.0234 (9)	0.0258 (9)	−0.0049 (7)	−0.0049 (7)	−0.0065 (7)
C2	0.0244 (9)	0.0211 (8)	0.0283 (9)	−0.0059 (7)	−0.0063 (7)	−0.0043 (7)
C3	0.0225 (8)	0.0191 (8)	0.0342 (10)	−0.0052 (7)	−0.0054 (7)	−0.0044 (7)
C4	0.0222 (9)	0.0275 (9)	0.0378 (10)	−0.0026 (7)	−0.0042 (8)	−0.0109 (8)
C5	0.0281 (9)	0.0309 (10)	0.0409 (11)	−0.0041 (8)	−0.0012 (8)	−0.0150 (8)
C6	0.0225 (9)	0.0276 (10)	0.0526 (12)	−0.0018 (7)	0.0015 (8)	−0.0139 (9)
C7	0.0215 (9)	0.0225 (9)	0.0569 (13)	−0.0032 (7)	−0.0091 (8)	−0.0071 (9)
C8	0.0259 (9)	0.0189 (9)	0.0420 (11)	−0.0062 (7)	−0.0083 (8)	−0.0034 (8)
C9	0.0288 (10)	0.0266 (10)	0.0453 (12)	−0.0078 (8)	−0.0166 (9)	−0.0018 (8)
C10	0.0368 (11)	0.0280 (10)	0.0375 (11)	−0.0101 (8)	−0.0167 (9)	−0.0039 (8)
C11	0.0305 (9)	0.0226 (9)	0.0301 (9)	−0.0071 (7)	−0.0073 (7)	−0.0044 (7)
C12	0.0313 (9)	0.0216 (9)	0.0254 (9)	−0.0062 (7)	−0.0073 (7)	−0.0031 (7)
C13	0.0325 (9)	0.0214 (9)	0.0252 (9)	−0.0063 (7)	−0.0029 (7)	−0.0080 (7)
C14	0.0394 (10)	0.0257 (9)	0.0261 (9)	−0.0035 (8)	−0.0073 (8)	−0.0056 (7)
C15	0.0432 (11)	0.0319 (10)	0.0232 (9)	−0.0078 (8)	−0.0005 (8)	−0.0072 (8)
C16	0.0285 (9)	0.0320 (10)	0.0327 (10)	−0.0077 (8)	0.0009 (8)	−0.0163 (8)
C17	0.0340 (10)	0.0297 (10)	0.0305 (10)	−0.0007 (8)	−0.0083 (8)	−0.0120 (8)
C18	0.0368 (10)	0.0275 (9)	0.0227 (9)	−0.0050 (8)	−0.0042 (8)	−0.0085 (7)
C19	0.0194 (8)	0.0249 (9)	0.0265 (9)	−0.0010 (6)	−0.0045 (7)	−0.0087 (7)
C24	0.0450 (11)	0.0311 (10)	0.0329 (10)	−0.0109 (9)	−0.0146 (9)	−0.0085 (8)
C20	0.0500 (12)	0.0320 (10)	0.0270 (10)	−0.0104 (9)	−0.0055 (9)	−0.0117 (8)
C21	0.0525 (13)	0.0269 (10)	0.0360 (11)	−0.0115 (9)	−0.0038 (9)	−0.0100 (8)
C22	0.0388 (11)	0.0305 (10)	0.0289 (10)	−0.0020 (8)	−0.0056 (8)	−0.0038 (8)
C23	0.0583 (14)	0.0400 (12)	0.0282 (10)	−0.0096 (10)	−0.0168 (10)	−0.0075 (9)

Br—C16	1.8973 (19)	C10—H10	0.9300
S—O2	1.4933 (13)	C12—C13	1.460 (3)
S—C1	1.7662 (18)	C13—C14	1.399 (3)
S—C19	1.7987 (18)	C13—C18	1.400 (3)
O1—C12	1.371 (2)	C14—C15	1.382 (3)
O1—C11	1.373 (2)	C14—H14	0.9300
C1—C12	1.372 (2)	C15—C16	1.384 (3)
C1—C2	1.450 (2)	C15—H15	0.9300
C2—C11	1.382 (3)	C16—C17	1.384 (3)
C2—C3	1.429 (2)	C17—C18	1.382 (3)
C3—C4	1.410 (3)	C17—H17	0.9300
C3—C8	1.434 (3)	C18—H18	0.9300
C4—C5	1.375 (3)	C19—C24	1.380 (3)
C4—H4	0.9300	C19—C20	1.381 (3)
C5—C6	1.408 (3)	C24—C23	1.390 (3)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.365 (3)	C20—C21	1.388 (3)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.419 (3)	C21—C22	1.376 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.426 (3)	C22—C23	1.376 (3)
C9—C10	1.361 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.405 (3)
O2—S—C1	109.42 (8)	O1—C12—C13	116.43 (15)
O2—S—C19	107.01 (8)	C1—C12—C13	133.04 (17)
C1—S—C19	99.88 (8)	C14—C13—C18	118.53 (17)
C12—O1—C11	106.49 (14)	C14—C13—C12	120.29 (17)
C12—C1—C2	106.91 (15)	C18—C13—C12	121.17 (16)
C12—C1—S	120.79 (14)	C15—C14—C13	120.79 (18)
C2—C1—S	131.42 (14)	C15—C14—H14	119.6
C11—C2—C3	119.50 (16)	C13—C14—H14	119.6
C11—C2—C1	104.65 (16)	C14—C15—C16	119.25 (17)
C3—C2—C1	135.85 (17)	C14—C15—H15	120.4
C4—C3—C2	124.40 (16)	C16—C15—H15	120.4
C4—C3—C8	119.09 (17)	C17—C16—C15	121.29 (18)
C2—C3—C8	116.51 (17)	C17—C16—Br	119.08 (15)
C5—C4—C3	121.00 (17)	C15—C16—Br	119.63 (14)
C5—C4—H4	119.5	C18—C17—C16	119.12 (18)
C3—C4—H4	119.5	C18—C17—H17	120.4
C4—C5—C6	119.96 (19)	C16—C17—H17	120.4
C4—C5—H5	120.0	C17—C18—C13	120.93 (17)
C6—C5—H5	120.0	C17—C18—H18	119.5
C7—C6—C5	120.60 (18)	C13—C18—H18	119.5
C7—C6—H6	119.7	C24—C19—C20	120.56 (17)
C5—C6—H6	119.7	C24—C19—S	116.87 (14)
C6—C7—C8	121.14 (18)	C20—C19—S	122.40 (14)
C6—C7—H7	119.4	C19—C24—C23	119.21 (18)
C8—C7—H7	119.4	C19—C24—H24	120.4
C7—C8—C9	121.21 (18)	C23—C24—H24	120.4
C7—C8—C3	118.20 (18)	C19—C20—C21	119.64 (18)
C9—C8—C3	120.59 (18)	C19—C20—H20	120.2
C10—C9—C8	122.32 (18)	C21—C20—H20	120.2
C10—C9—H9	118.8	C22—C21—C20	120.15 (19)
C8—C9—H9	118.8	C22—C21—H21	119.9
C9—C10—C11	116.50 (18)	C20—C21—H21	119.9
C9—C10—H10	121.7	C23—C22—C21	119.87 (19)
C11—C10—H10	121.7	C23—C22—H22	120.1
O1—C11—C2	111.42 (16)	C21—C22—H22	120.1
O1—C11—C10	124.05 (17)	C22—C23—C24	120.55 (19)
C2—C11—C10	124.53 (18)	C22—C23—H23	119.7
O1—C12—C1	110.53 (16)	C24—C23—H23	119.7
O2—S—C1—C12	128.31 (15)	C9—C10—C11—C2	−2.1 (3)
C19—S—C1—C12	−119.58 (15)	C11—O1—C12—C1	0.08 (19)
O2—S—C1—C2	−39.51 (19)	C11—O1—C12—C13	−179.65 (15)
C19—S—C1—C2	72.60 (18)	C2—C1—C12—O1	0.4 (2)
C12—C1—C2—C11	−0.79 (19)	S—C1—C12—O1	−170.03 (12)
S—C1—C2—C11	168.29 (14)	C2—C1—C12—C13	−179.88 (18)
C12—C1—C2—C3	178.88 (19)	S—C1—C12—C13	9.6 (3)
S—C1—C2—C3	−12.0 (3)	O1—C12—C13—C14	32.4 (2)
C11—C2—C3—C4	179.44 (17)	C1—C12—C13—C14	−147.3 (2)
C1—C2—C3—C4	−0.2 (3)	O1—C12—C13—C18	−148.06 (17)
C11—C2—C3—C8	−0.2 (2)	C1—C12—C13—C18	32.3 (3)
C1—C2—C3—C8	−179.86 (19)	C18—C13—C14—C15	−2.7 (3)
C2—C3—C4—C5	−178.61 (17)	C12—C13—C14—C15	176.95 (17)
C8—C3—C4—C5	1.0 (3)	C13—C14—C15—C16	0.3 (3)
C3—C4—C5—C6	−0.1 (3)	C14—C15—C16—C17	1.8 (3)
C4—C5—C6—C7	−0.5 (3)	C14—C15—C16—Br	−177.73 (15)
C5—C6—C7—C8	0.0 (3)	C15—C16—C17—C18	−1.4 (3)
C6—C7—C8—C9	−179.59 (18)	Br—C16—C17—C18	178.17 (14)
C6—C7—C8—C3	1.0 (3)	C16—C17—C18—C13	−1.1 (3)
C4—C3—C8—C7	−1.5 (3)	C14—C13—C18—C17	3.1 (3)
C2—C3—C8—C7	178.21 (16)	C12—C13—C18—C17	−176.49 (17)
C4—C3—C8—C9	179.06 (17)	O2—S—C19—C24	−37.46 (17)
C2—C3—C8—C9	−1.2 (3)	C1—S—C19—C24	−151.42 (15)
C7—C8—C9—C10	−178.31 (18)	O2—S—C19—C20	147.24 (16)
C3—C8—C9—C10	1.1 (3)	C1—S—C19—C20	33.28 (18)
C8—C9—C10—C11	0.5 (3)	C20—C19—C24—C23	−0.2 (3)
C12—O1—C11—C2	−0.62 (19)	S—C19—C24—C23	−175.62 (17)
C12—O1—C11—C10	178.53 (17)	C24—C19—C20—C21	−0.1 (3)
C3—C2—C11—O1	−178.87 (15)	S—C19—C20—C21	175.04 (16)
C1—C2—C11—O1	0.9 (2)	C19—C20—C21—C22	−0.5 (3)
C3—C2—C11—C10	2.0 (3)	C20—C21—C22—C23	1.4 (3)
C1—C2—C11—C10	−178.27 (17)	C21—C22—C23—C24	−1.7 (3)
C9—C10—C11—O1	178.85 (16)	C19—C24—C23—C22	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2i	0.93	2.57	3.482 (2)	167
C20—H20···Brii	0.93	2.98	3.760 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2i	0.93	2.57	3.482 (2)	167
C20—H20⋯Brii	0.93	2.98	3.760 (2)	143

Symmetry codes: (i) ; (ii) .