2-Phenyl-3-(phenyl-sulfin-yl)naphtho[1,2-b]furan.

In the title compound, C(24)H(16)O(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [81.54 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 18.2 (1)°.

Related literature

For the crystal structures of similar naphtho[1,2-b]furan derivatives, see: Choi et al. (2008 ▶). For the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ▶); Piloto et al. (2005 ▶).

Experimental

Crystal data

C24H16O2S

M = 368.44

Monoclinic,

a = 10.123 (1) Å

b = 14.109 (2) Å

c = 12.410 (2) Å

β = 99.743 (2)°

V = 1746.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

10523 measured reflections

3804 independent reflections

2555 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.137

S = 1.05

3804 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.41 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023101/hg2520sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023101/hg2520Isup2.hkl

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

C24H16O2S	F(000) = 768
Mr = 368.44	Dx = 1.401 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2794 reflections
a = 10.123 (1) Å	θ = 2.4–28.0°
b = 14.109 (2) Å	µ = 0.20 mm−1
c = 12.410 (2) Å	T = 173 K
β = 99.743 (2)°	Block, colorless
V = 1746.9 (4) Å3	0.20 × 0.20 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	2555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.079
graphite	θmax = 27.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm-1	h = −12→12
φ and ω scans	k = −18→17
10523 measured reflections	l = −15→10
3804 independent 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)] = 0.053	Hydrogen site location: difference Fourier map
wR(F2) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.5717P] where P = (Fo2 + 2Fc2)/3
3804 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.41 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
S	0.28091 (6)	0.00804 (5)	0.16729 (5)	0.02695 (19)
O1	0.40566 (16)	0.15573 (12)	0.43697 (13)	0.0242 (4)
O2	0.20908 (19)	0.07138 (13)	0.08044 (15)	0.0371 (5)
C1	0.3042 (2)	0.07384 (17)	0.2906 (2)	0.0237 (5)
C2	0.2072 (2)	0.13705 (17)	0.3244 (2)	0.0245 (5)
C3	0.0698 (2)	0.15748 (18)	0.2865 (2)	0.0287 (6)
H3	0.0206	0.1244	0.2261	0.034*
C4	0.0109 (2)	0.22564 (19)	0.3393 (2)	0.0296 (6)
H4	−0.0810	0.2396	0.3146	0.035*
C5	0.0812 (2)	0.27738 (18)	0.4303 (2)	0.0257 (6)
C6	0.0202 (3)	0.34960 (19)	0.4835 (2)	0.0306 (6)
H6	−0.0720	0.3636	0.4600	0.037*
C7	0.0913 (3)	0.39968 (19)	0.5680 (2)	0.0331 (6)
H7	0.0481	0.4480	0.6025	0.040*
C8	0.2281 (3)	0.38060 (19)	0.6046 (2)	0.0322 (6)
H8	0.2768	0.4163	0.6631	0.039*
C9	0.2907 (3)	0.31082 (18)	0.5560 (2)	0.0287 (6)
H9	0.3829	0.2980	0.5812	0.034*
C19	0.1603 (2)	−0.07478 (17)	0.2024 (2)	0.0247 (5)
C10	0.2198 (2)	0.25777 (17)	0.4690 (2)	0.0234 (5)
C11	0.2748 (2)	0.18564 (17)	0.4126 (2)	0.0236 (5)
C12	0.4218 (2)	0.08750 (17)	0.3604 (2)	0.0238 (5)
C13	0.5573 (2)	0.04856 (18)	0.3710 (2)	0.0245 (6)
C14	0.5820 (3)	−0.03834 (18)	0.3242 (2)	0.0291 (6)
H14	0.5092	−0.0741	0.2861	0.035*
C15	0.7112 (3)	−0.07276 (19)	0.3326 (2)	0.0335 (6)
H15	0.7268	−0.1318	0.3001	0.040*
C16	0.8175 (3)	−0.0217 (2)	0.3881 (2)	0.0359 (7)
H16	0.9064	−0.0449	0.3927	0.043*
C17	0.7944 (3)	0.0634 (2)	0.4371 (2)	0.0372 (7)
H17	0.8673	0.0976	0.4773	0.045*
C18	0.6658 (3)	0.0989 (2)	0.4279 (2)	0.0311 (6)
H18	0.6512	0.1580	0.4605	0.037*
C20	0.0331 (3)	−0.07786 (19)	0.1411 (2)	0.0308 (6)
H20	0.0073	−0.0336	0.0837	0.037*
C21	−0.0565 (3)	−0.1460 (2)	0.1641 (2)	0.0349 (7)
H21	−0.1441	−0.1486	0.1222	0.042*
C22	−0.0190 (3)	−0.21003 (19)	0.2474 (2)	0.0351 (7)
H22	−0.0813	−0.2560	0.2636	0.042*
C23	0.1093 (3)	−0.20754 (19)	0.3078 (2)	0.0318 (6)
H23	0.1350	−0.2521	0.3649	0.038*
C24	0.1998 (3)	−0.14042 (18)	0.2852 (2)	0.0290 (6)
H24	0.2882	−0.1390	0.3257	0.035*

	U11	U22	U33	U12	U13	U23
S	0.0311 (3)	0.0275 (4)	0.0222 (3)	−0.0035 (3)	0.0044 (3)	−0.0006 (3)
O1	0.0217 (8)	0.0279 (10)	0.0219 (9)	0.0022 (7)	0.0003 (7)	−0.0001 (7)
O2	0.0493 (12)	0.0350 (11)	0.0250 (10)	−0.0060 (9)	0.0006 (9)	0.0065 (8)
C1	0.0273 (13)	0.0217 (13)	0.0215 (13)	−0.0017 (10)	0.0021 (10)	0.0016 (10)
C2	0.0269 (13)	0.0220 (13)	0.0238 (13)	−0.0018 (10)	0.0025 (11)	0.0047 (11)
C3	0.0259 (13)	0.0286 (14)	0.0291 (14)	−0.0024 (11)	−0.0027 (11)	0.0000 (12)
C4	0.0203 (12)	0.0316 (15)	0.0350 (15)	0.0024 (11)	−0.0007 (11)	0.0048 (12)
C5	0.0274 (13)	0.0259 (14)	0.0242 (13)	0.0018 (11)	0.0056 (11)	0.0062 (11)
C6	0.0280 (13)	0.0300 (15)	0.0350 (16)	0.0059 (11)	0.0087 (12)	0.0084 (12)
C7	0.0413 (15)	0.0288 (15)	0.0320 (15)	0.0071 (12)	0.0144 (13)	0.0011 (12)
C8	0.0397 (15)	0.0289 (15)	0.0278 (14)	0.0013 (12)	0.0056 (12)	−0.0007 (12)
C9	0.0290 (13)	0.0302 (15)	0.0264 (14)	0.0015 (11)	0.0038 (11)	0.0019 (11)
C19	0.0303 (13)	0.0212 (13)	0.0233 (13)	−0.0026 (11)	0.0061 (11)	−0.0048 (10)
C10	0.0253 (13)	0.0239 (13)	0.0216 (13)	−0.0006 (10)	0.0053 (10)	0.0046 (10)
C11	0.0221 (12)	0.0231 (13)	0.0246 (13)	0.0001 (10)	0.0011 (10)	0.0048 (10)
C12	0.0299 (13)	0.0209 (13)	0.0210 (13)	−0.0023 (11)	0.0056 (10)	0.0008 (10)
C13	0.0254 (12)	0.0293 (14)	0.0188 (12)	0.0019 (10)	0.0032 (10)	0.0054 (11)
C14	0.0288 (13)	0.0268 (14)	0.0313 (15)	−0.0017 (11)	0.0041 (12)	0.0022 (12)
C15	0.0359 (15)	0.0286 (15)	0.0365 (16)	0.0080 (12)	0.0077 (13)	0.0038 (13)
C16	0.0273 (14)	0.0436 (17)	0.0366 (16)	0.0120 (13)	0.0048 (12)	0.0081 (14)
C17	0.0300 (14)	0.0487 (19)	0.0302 (15)	0.0029 (13)	−0.0024 (12)	−0.0006 (13)
C18	0.0313 (14)	0.0335 (16)	0.0266 (14)	0.0035 (12)	−0.0006 (11)	−0.0020 (12)
C20	0.0333 (14)	0.0303 (15)	0.0277 (14)	0.0002 (12)	0.0017 (12)	−0.0001 (12)
C21	0.0285 (14)	0.0397 (17)	0.0363 (16)	−0.0065 (12)	0.0048 (12)	−0.0060 (13)
C22	0.0410 (16)	0.0260 (15)	0.0417 (17)	−0.0080 (12)	0.0167 (14)	−0.0075 (13)
C23	0.0446 (16)	0.0229 (14)	0.0294 (15)	0.0025 (12)	0.0103 (13)	0.0031 (11)
C24	0.0317 (14)	0.0298 (14)	0.0243 (13)	−0.0015 (11)	0.0011 (11)	−0.0007 (11)

S—O2	1.4912 (19)	C19—C24	1.390 (3)
S—C1	1.771 (3)	C10—C11	1.403 (3)
S—C19	1.796 (3)	C12—C13	1.463 (3)
O1—C11	1.375 (3)	C13—C18	1.395 (3)
O1—C12	1.381 (3)	C13—C14	1.397 (4)
C1—C12	1.363 (3)	C14—C15	1.383 (4)
C1—C2	1.440 (3)	C14—H14	0.9500
C2—C11	1.372 (3)	C15—C16	1.378 (4)
C2—C3	1.420 (3)	C15—H15	0.9500
C3—C4	1.356 (4)	C16—C17	1.384 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.429 (4)	C17—C18	1.381 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.412 (4)	C18—H18	0.9500
C5—C10	1.431 (3)	C20—C21	1.384 (4)
C6—C7	1.365 (4)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.377 (4)
C7—C8	1.408 (4)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.386 (4)
C8—C9	1.365 (4)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.379 (4)
C9—C10	1.407 (3)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C19—C20	1.381 (3)
O2—S—C1	106.72 (11)	C2—C11—C10	125.0 (2)
O2—S—C19	107.27 (11)	O1—C11—C10	124.2 (2)
C1—S—C19	97.33 (11)	C1—C12—O1	110.1 (2)
C11—O1—C12	106.53 (18)	C1—C12—C13	135.2 (2)
C12—C1—C2	107.0 (2)	O1—C12—C13	114.7 (2)
C12—C1—S	126.7 (2)	C18—C13—C14	118.4 (2)
C2—C1—S	125.37 (18)	C18—C13—C12	120.0 (2)
C11—C2—C3	119.4 (2)	C14—C13—C12	121.5 (2)
C11—C2—C1	105.6 (2)	C15—C14—C13	120.7 (2)
C3—C2—C1	135.0 (2)	C15—C14—H14	119.7
C4—C3—C2	118.0 (2)	C13—C14—H14	119.7
C4—C3—H3	121.0	C16—C15—C14	120.2 (3)
C2—C3—H3	121.0	C16—C15—H15	119.9
C3—C4—C5	122.9 (2)	C14—C15—H15	119.9
C3—C4—H4	118.6	C15—C16—C17	119.8 (2)
C5—C4—H4	118.6	C15—C16—H16	120.1
C6—C5—C4	122.7 (2)	C17—C16—H16	120.1
C6—C5—C10	117.6 (2)	C18—C17—C16	120.3 (3)
C4—C5—C10	119.7 (2)	C18—C17—H17	119.8
C7—C6—C5	121.1 (2)	C16—C17—H17	119.8
C7—C6—H6	119.4	C17—C18—C13	120.5 (3)
C5—C6—H6	119.4	C17—C18—H18	119.7
C6—C7—C8	120.7 (3)	C13—C18—H18	119.7
C6—C7—H7	119.6	C19—C20—C21	119.4 (3)
C8—C7—H7	119.6	C19—C20—H20	120.3
C9—C8—C7	120.0 (3)	C21—C20—H20	120.3
C9—C8—H8	120.0	C22—C21—C20	120.2 (3)
C7—C8—H8	120.0	C22—C21—H21	119.9
C8—C9—C10	120.5 (2)	C20—C21—H21	119.9
C8—C9—H9	119.8	C21—C22—C23	120.2 (3)
C10—C9—H9	119.8	C21—C22—H22	119.9
C20—C19—C24	120.7 (2)	C23—C22—H22	119.9
C20—C19—S	119.7 (2)	C24—C23—C22	120.1 (3)
C24—C19—S	119.35 (19)	C24—C23—H23	120.0
C11—C10—C9	125.1 (2)	C22—C23—H23	120.0
C11—C10—C5	115.0 (2)	C23—C24—C19	119.3 (2)
C9—C10—C5	120.0 (2)	C23—C24—H24	120.3
C2—C11—O1	110.7 (2)	C19—C24—H24	120.3
O2—S—C1—C12	−127.7 (2)	C12—O1—C11—C2	1.2 (3)
C19—S—C1—C12	121.7 (2)	C12—O1—C11—C10	−177.3 (2)
O2—S—C1—C2	39.8 (2)	C9—C10—C11—C2	−176.7 (2)
C19—S—C1—C2	−70.8 (2)	C5—C10—C11—C2	1.9 (4)
C12—C1—C2—C11	0.7 (3)	C9—C10—C11—O1	1.6 (4)
S—C1—C2—C11	−168.88 (19)	C5—C10—C11—O1	−179.8 (2)
C12—C1—C2—C3	179.5 (3)	C2—C1—C12—O1	0.0 (3)
S—C1—C2—C3	10.0 (4)	S—C1—C12—O1	169.41 (17)
C11—C2—C3—C4	0.6 (4)	C2—C1—C12—C13	−178.7 (3)
C1—C2—C3—C4	−178.1 (3)	S—C1—C12—C13	−9.4 (4)
C2—C3—C4—C5	0.2 (4)	C11—O1—C12—C1	−0.7 (3)
C3—C4—C5—C6	178.7 (2)	C11—O1—C12—C13	178.3 (2)
C3—C4—C5—C10	0.0 (4)	C1—C12—C13—C18	158.3 (3)
C4—C5—C6—C7	−177.9 (2)	O1—C12—C13—C18	−20.4 (3)
C10—C5—C6—C7	0.8 (4)	C1—C12—C13—C14	−20.9 (4)
C5—C6—C7—C8	0.0 (4)	O1—C12—C13—C14	160.3 (2)
C6—C7—C8—C9	−0.5 (4)	C18—C13—C14—C15	−1.0 (4)
C7—C8—C9—C10	0.3 (4)	C12—C13—C14—C15	178.3 (2)
O2—S—C19—C20	7.9 (2)	C13—C14—C15—C16	0.3 (4)
C1—S—C19—C20	118.0 (2)	C14—C15—C16—C17	1.2 (4)
O2—S—C19—C24	−177.6 (2)	C15—C16—C17—C18	−2.0 (4)
C1—S—C19—C24	−67.5 (2)	C16—C17—C18—C13	1.3 (4)
C8—C9—C10—C11	179.1 (2)	C14—C13—C18—C17	0.2 (4)
C8—C9—C10—C5	0.5 (4)	C12—C13—C18—C17	−179.1 (2)
C6—C5—C10—C11	−179.7 (2)	C24—C19—C20—C21	1.3 (4)
C4—C5—C10—C11	−1.0 (3)	S—C19—C20—C21	175.7 (2)
C6—C5—C10—C9	−1.0 (4)	C19—C20—C21—C22	0.1 (4)
C4—C5—C10—C9	177.7 (2)	C20—C21—C22—C23	−1.0 (4)
C3—C2—C11—O1	179.8 (2)	C21—C22—C23—C24	0.5 (4)
C1—C2—C11—O1	−1.2 (3)	C22—C23—C24—C19	0.9 (4)
C3—C2—C11—C10	−1.8 (4)	C20—C19—C24—C23	−1.8 (4)
C1—C2—C11—C10	177.3 (2)	S—C19—C24—C23	−176.2 (2)