2-Phenyl-1-(phenyl-sulfin-yl)naphtho[2,1-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 [82.34 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21 (6)°. The crystal structure shows π-π inter-actions between the central benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.516 (3) Å], as well as non-classical C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar naphtho[2,1-b]furan derivatives, see: Choi et al. (2007 ▶, 2008 ▶). For the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ▶); Hagiwara et al. (1999 ▶); Piloto et al. (2005 ▶).

Experimental

Crystal data

C24H16O2S

M = 368.43

Triclinic,

a = 9.2262 (7) Å

b = 10.3430 (8) Å

c = 10.4296 (8) Å

α = 78.298 (1)°

β = 86.849 (1)°

γ = 67.506 (1)°

V = 900.15 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

6736 measured reflections

3140 independent reflections

2602 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.06

3140 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.36 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/S1600536809019977/ng2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019977/ng2587Isup2.hkl

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

C24H16O2S	Z = 2
Mr = 368.43	F(000) = 384
Triclinic, P1	Dx = 1.359 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2262 (7) Å	Cell parameters from 3903 reflections
b = 10.3430 (8) Å	θ = 2.2–28.1°
c = 10.4296 (8) Å	µ = 0.20 mm−1
α = 78.298 (1)°	T = 173 K
β = 86.849 (1)°	Block, colorless
γ = 67.506 (1)°	0.30 × 0.20 × 0.10 mm
V = 900.15 (12) Å3

Bruker SMART CCD diffractometer	2602 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
graphite	θmax = 25.0°, θmin = 2.6°
Detector resolution: 10.0 pixels mm-1	h = −10→10
φ and ω scans	k = −12→12
6736 measured reflections	l = −12→12
3140 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0292P)2 + 0.4516P] where P = (Fo2 + 2Fc2)/3
3140 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.36 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	0.92526 (5)	0.67298 (6)	0.63521 (5)	0.02249 (16)
O1	0.55628 (15)	0.80588 (16)	0.40427 (15)	0.0287 (4)
O2	1.01571 (15)	0.51840 (16)	0.68794 (15)	0.0304 (4)
C1	0.7484 (2)	0.6976 (2)	0.5575 (2)	0.0217 (4)
C2	0.6230 (2)	0.6466 (2)	0.5980 (2)	0.0225 (5)
C3	0.5963 (2)	0.5480 (2)	0.7043 (2)	0.0247 (5)
C4	0.7034 (2)	0.4667 (2)	0.8087 (2)	0.0288 (5)
H4	0.8013	0.4767	0.8114	0.035*
C5	0.6685 (3)	0.3735 (3)	0.9063 (2)	0.0369 (6)
H5	0.7423	0.3195	0.9760	0.044*
C6	0.5244 (3)	0.3568 (3)	0.9045 (3)	0.0409 (6)
H6	0.5006	0.2928	0.9733	0.049*
C7	0.4196 (3)	0.4323 (3)	0.8042 (3)	0.0367 (6)
H7	0.3231	0.4194	0.8033	0.044*
C8	0.4506 (2)	0.5296 (2)	0.7011 (2)	0.0304 (5)
C9	0.3413 (2)	0.6054 (3)	0.5950 (3)	0.0350 (6)
H9	0.2462	0.5900	0.5946	0.042*
C10	0.3676 (2)	0.6990 (3)	0.4943 (2)	0.0341 (6)
H10	0.2936	0.7499	0.4242	0.041*
C11	0.5109 (2)	0.7163 (2)	0.4998 (2)	0.0265 (5)
C12	0.7040 (2)	0.7901 (2)	0.4412 (2)	0.0240 (5)
C13	0.7758 (2)	0.8777 (2)	0.3541 (2)	0.0245 (5)
C14	0.6902 (3)	1.0219 (2)	0.3089 (2)	0.0310 (5)
H14	0.5843	1.0632	0.3339	0.037*
C15	0.7568 (3)	1.1061 (2)	0.2284 (2)	0.0355 (6)
H15	0.6975	1.2049	0.1987	0.043*
C16	0.9113 (3)	1.0456 (3)	0.1907 (2)	0.0362 (6)
H16	0.9579	1.1031	0.1350	0.043*
C17	0.9966 (3)	0.9026 (3)	0.2340 (2)	0.0332 (5)
H17	1.1020	0.8618	0.2076	0.040*
C18	0.9314 (2)	0.8173 (2)	0.3153 (2)	0.0280 (5)
H18	0.9914	0.7185	0.3448	0.034*
C19	0.8432 (2)	0.7532 (2)	0.7740 (2)	0.0233 (5)
C20	0.7332 (2)	0.8915 (2)	0.7556 (2)	0.0296 (5)
H20	0.6946	0.9429	0.6700	0.036*
C21	0.6802 (3)	0.9539 (3)	0.8632 (3)	0.0376 (6)
H21	0.6040	1.0485	0.8519	0.045*
C22	0.7381 (3)	0.8787 (3)	0.9879 (2)	0.0369 (6)
H22	0.7005	0.9218	1.0617	0.044*
C23	0.8501 (3)	0.7414 (3)	1.0049 (2)	0.0344 (5)
H23	0.8901	0.6904	1.0901	0.041*
C24	0.9038 (2)	0.6785 (2)	0.8972 (2)	0.0286 (5)
H24	0.9817	0.5846	0.9080	0.034*

	U11	U22	U33	U12	U13	U23
S	0.0174 (2)	0.0248 (3)	0.0242 (3)	−0.0081 (2)	−0.00033 (18)	−0.0022 (2)
O1	0.0238 (7)	0.0305 (9)	0.0299 (9)	−0.0084 (6)	−0.0053 (6)	−0.0044 (7)
O2	0.0223 (7)	0.0265 (9)	0.0369 (10)	−0.0036 (6)	−0.0003 (6)	−0.0050 (7)
C1	0.0188 (9)	0.0223 (11)	0.0238 (11)	−0.0064 (8)	0.0017 (8)	−0.0074 (9)
C2	0.0193 (9)	0.0216 (11)	0.0274 (12)	−0.0063 (8)	0.0018 (8)	−0.0095 (9)
C3	0.0232 (10)	0.0224 (11)	0.0308 (12)	−0.0091 (8)	0.0083 (8)	−0.0112 (9)
C4	0.0261 (11)	0.0277 (12)	0.0332 (13)	−0.0113 (9)	0.0050 (9)	−0.0062 (10)
C5	0.0389 (12)	0.0335 (14)	0.0367 (14)	−0.0142 (10)	0.0070 (10)	−0.0046 (11)
C6	0.0474 (14)	0.0377 (15)	0.0431 (16)	−0.0235 (12)	0.0206 (12)	−0.0106 (12)
C7	0.0319 (12)	0.0411 (15)	0.0481 (16)	−0.0229 (11)	0.0184 (11)	−0.0193 (12)
C8	0.0244 (10)	0.0321 (13)	0.0389 (14)	−0.0115 (9)	0.0105 (9)	−0.0172 (11)
C9	0.0197 (10)	0.0421 (15)	0.0493 (16)	−0.0135 (10)	0.0068 (10)	−0.0207 (12)
C10	0.0211 (10)	0.0397 (14)	0.0417 (15)	−0.0075 (10)	−0.0035 (9)	−0.0158 (11)
C11	0.0225 (10)	0.0256 (12)	0.0316 (13)	−0.0071 (9)	0.0020 (8)	−0.0104 (9)
C12	0.0207 (9)	0.0244 (11)	0.0257 (12)	−0.0053 (8)	−0.0019 (8)	−0.0085 (9)
C13	0.0281 (10)	0.0268 (12)	0.0196 (11)	−0.0105 (9)	−0.0003 (8)	−0.0064 (9)
C14	0.0325 (11)	0.0265 (13)	0.0302 (13)	−0.0064 (9)	0.0002 (9)	−0.0072 (10)
C15	0.0466 (13)	0.0213 (12)	0.0367 (14)	−0.0115 (10)	−0.0019 (10)	−0.0036 (10)
C16	0.0468 (13)	0.0354 (14)	0.0331 (14)	−0.0249 (11)	0.0010 (10)	−0.0027 (11)
C17	0.0305 (11)	0.0376 (14)	0.0325 (13)	−0.0144 (10)	0.0019 (9)	−0.0064 (11)
C18	0.0290 (11)	0.0247 (12)	0.0282 (12)	−0.0075 (9)	−0.0010 (9)	−0.0051 (9)
C19	0.0208 (10)	0.0268 (12)	0.0257 (12)	−0.0128 (9)	0.0000 (8)	−0.0045 (9)
C20	0.0261 (10)	0.0292 (13)	0.0314 (13)	−0.0080 (9)	−0.0063 (9)	−0.0045 (10)
C21	0.0298 (12)	0.0363 (14)	0.0453 (16)	−0.0060 (10)	−0.0018 (10)	−0.0173 (12)
C22	0.0374 (13)	0.0480 (16)	0.0337 (14)	−0.0202 (11)	0.0059 (10)	−0.0199 (12)
C23	0.0453 (13)	0.0397 (14)	0.0251 (13)	−0.0252 (11)	−0.0016 (10)	−0.0027 (10)
C24	0.0335 (11)	0.0244 (12)	0.0288 (13)	−0.0137 (9)	−0.0030 (9)	−0.0009 (9)

S—O2	1.4926 (15)	C12—C13	1.464 (3)
S—C1	1.7690 (19)	C13—C14	1.388 (3)
S—C19	1.801 (2)	C13—C18	1.402 (3)
O1—C12	1.376 (2)	C14—C15	1.377 (3)
O1—C11	1.380 (3)	C14—H14	0.9500
C1—C12	1.356 (3)	C15—C16	1.391 (3)
C1—C2	1.455 (3)	C15—H15	0.9500
C2—C11	1.373 (3)	C16—C17	1.375 (3)
C2—C3	1.426 (3)	C16—H16	0.9500
C3—C4	1.407 (3)	C17—C18	1.381 (3)
C3—C8	1.431 (3)	C17—H17	0.9500
C4—C5	1.369 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C24	1.380 (3)
C5—C6	1.406 (3)	C19—C20	1.383 (3)
C5—H5	0.9500	C20—C21	1.381 (3)
C6—C7	1.357 (4)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.389 (4)
C7—C8	1.414 (3)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.382 (3)
C8—C9	1.423 (3)	C22—H22	0.9500
C9—C10	1.355 (4)	C23—C24	1.386 (3)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.406 (3)	C24—H24	0.9500
C10—H10	0.9500
O2—S—C1	110.64 (9)	C1—C12—C13	133.87 (18)
O2—S—C19	106.60 (9)	O1—C12—C13	115.97 (18)
C1—S—C19	98.59 (9)	C14—C13—C18	119.2 (2)
C12—O1—C11	106.29 (16)	C14—C13—C12	120.17 (18)
C12—C1—C2	107.88 (17)	C18—C13—C12	120.62 (19)
C12—C1—S	119.06 (15)	C15—C14—C13	120.8 (2)
C2—C1—S	132.80 (16)	C15—C14—H14	119.6
C11—C2—C3	119.15 (18)	C13—C14—H14	119.6
C11—C2—C1	104.07 (19)	C14—C15—C16	119.7 (2)
C3—C2—C1	136.75 (18)	C14—C15—H15	120.2
C4—C3—C2	124.79 (18)	C16—C15—H15	120.2
C4—C3—C8	118.6 (2)	C17—C16—C15	119.9 (2)
C2—C3—C8	116.6 (2)	C17—C16—H16	120.1
C5—C4—C3	120.9 (2)	C15—C16—H16	120.1
C5—C4—H4	119.5	C16—C17—C18	121.0 (2)
C3—C4—H4	119.5	C16—C17—H17	119.5
C4—C5—C6	120.6 (2)	C18—C17—H17	119.5
C4—C5—H5	119.7	C17—C18—C13	119.4 (2)
C6—C5—H5	119.7	C17—C18—H18	120.3
C7—C6—C5	119.8 (2)	C13—C18—H18	120.3
C7—C6—H6	120.1	C24—C19—C20	121.2 (2)
C5—C6—H6	120.1	C24—C19—S	118.22 (16)
C6—C7—C8	121.5 (2)	C20—C19—S	120.25 (17)
C6—C7—H7	119.2	C21—C20—C19	119.0 (2)
C8—C7—H7	119.2	C21—C20—H20	120.5
C7—C8—C9	121.0 (2)	C19—C20—H20	120.5
C7—C8—C3	118.5 (2)	C20—C21—C22	120.2 (2)
C9—C8—C3	120.5 (2)	C20—C21—H21	119.9
C10—C9—C8	122.5 (2)	C22—C21—H21	119.9
C10—C9—H9	118.8	C23—C22—C21	120.2 (2)
C8—C9—H9	118.8	C23—C22—H22	119.9
C9—C10—C11	116.1 (2)	C21—C22—H22	119.9
C9—C10—H10	122.0	C22—C23—C24	119.8 (2)
C11—C10—H10	122.0	C22—C23—H23	120.1
C2—C11—O1	111.62 (17)	C24—C23—H23	120.1
C2—C11—C10	125.1 (2)	C19—C24—C23	119.5 (2)
O1—C11—C10	123.3 (2)	C19—C24—H24	120.3
C1—C12—O1	110.10 (18)	C23—C24—H24	120.3
O2—S—C1—C12	−136.67 (16)	C9—C10—C11—C2	−0.1 (3)
C19—S—C1—C12	111.89 (17)	C9—C10—C11—O1	179.1 (2)
O2—S—C1—C2	50.0 (2)	C2—C1—C12—O1	1.4 (2)
C19—S—C1—C2	−61.5 (2)	S—C1—C12—O1	−173.45 (13)
C12—C1—C2—C11	−0.5 (2)	C2—C1—C12—C13	178.2 (2)
S—C1—C2—C11	173.40 (17)	S—C1—C12—C13	3.3 (3)
C12—C1—C2—C3	177.6 (2)	C11—O1—C12—C1	−1.8 (2)
S—C1—C2—C3	−8.5 (4)	C11—O1—C12—C13	−179.21 (17)
C11—C2—C3—C4	178.0 (2)	C1—C12—C13—C14	−129.7 (3)
C1—C2—C3—C4	0.1 (4)	O1—C12—C13—C14	47.0 (3)
C11—C2—C3—C8	−0.6 (3)	C1—C12—C13—C18	50.2 (3)
C1—C2—C3—C8	−178.5 (2)	O1—C12—C13—C18	−133.2 (2)
C2—C3—C4—C5	−179.5 (2)	C18—C13—C14—C15	−0.8 (3)
C8—C3—C4—C5	−0.9 (3)	C12—C13—C14—C15	179.1 (2)
C3—C4—C5—C6	0.0 (3)	C13—C14—C15—C16	0.6 (4)
C4—C5—C6—C7	0.9 (4)	C14—C15—C16—C17	−0.1 (4)
C5—C6—C7—C8	−0.8 (4)	C15—C16—C17—C18	−0.3 (4)
C6—C7—C8—C9	178.5 (2)	C16—C17—C18—C13	0.1 (3)
C6—C7—C8—C3	−0.2 (3)	C14—C13—C18—C17	0.5 (3)
C4—C3—C8—C7	1.1 (3)	C12—C13—C18—C17	−179.4 (2)
C2—C3—C8—C7	179.70 (19)	O2—S—C19—C24	16.08 (18)
C4—C3—C8—C9	−177.6 (2)	C1—S—C19—C24	130.73 (17)
C2—C3—C8—C9	1.0 (3)	O2—S—C19—C20	−170.04 (16)
C7—C8—C9—C10	−179.7 (2)	C1—S—C19—C20	−55.39 (18)
C3—C8—C9—C10	−1.1 (3)	C24—C19—C20—C21	−1.9 (3)
C8—C9—C10—C11	0.6 (3)	S—C19—C20—C21	−175.57 (17)
C3—C2—C11—O1	−179.15 (17)	C19—C20—C21—C22	0.6 (3)
C1—C2—C11—O1	−0.6 (2)	C20—C21—C22—C23	0.6 (4)
C3—C2—C11—C10	0.1 (3)	C21—C22—C23—C24	−0.5 (3)
C1—C2—C11—C10	178.7 (2)	C20—C19—C24—C23	2.0 (3)
C12—O1—C11—C2	1.5 (2)	S—C19—C24—C23	175.80 (15)
C12—O1—C11—C10	−177.8 (2)	C22—C23—C24—C19	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2i	0.95	2.59	3.488 (3)	158
C18—H18···O2ii	0.95	2.57	3.323 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2i	0.95	2.59	3.488 (3)	158
C18—H18⋯O2ii	0.95	2.57	3.323 (3)	137

Symmetry codes: (i) ; (ii) .