7-Bromo-2-phenyl-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan benzene hemisolvate.

The title compound, C(24)H(15)BrO(2)S·0.5C(6)H(6), crystallizes as a benzene hemisolvate. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment, and the phenyl ring is almost perpendicular to the plane of the naphthofuran fragment [83.78 (8)°] and is tilted slightly towards it. The 2-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 25.2 (1)°. The crystal structure is stabilized by aromatic π-π inter-actions between the central benzene ring and the furan ring of the neighbouring naphthofuran systems [centroid-centroid distance = 3.611 (3) Å], and by inter-molecular C-H⋯π inter-actions between the benzene H atom of the phenyl-sulfinyl substituent and the 2-phenyl ring of an adjacent mol-ecule. In addition, the crystal structure exhibits a weak non-classical inter-molecular C-H⋯O hydrogen bond.

Related literature

For the crystal structures of similar 7–bromo­naphtho[2,1–b]furan derivatives, see: Choi et al. (2007 ▶, 2008 ▶). 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

C24H15BrO2S·0.5C6H6

M = 486.38

Triclinic,

a = 8.154 (1) Å

b = 10.268 (2) Å

c = 13.771 (2) Å

α = 80.656 (2)°

β = 86.431 (2)°

γ = 75.377 (2)°

V = 1100.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.98 mm−1

T = 298 K

0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.504, T max = 0.826

8221 measured reflections

3870 independent reflections

2968 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.06

3870 reflections

280 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.74 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/S1600536809025860/fl2249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025860/fl2249Isup2.hkl

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

C24H15BrO2S·0.5C6H6	Z = 2
Mr = 486.38	F(000) = 494
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.154 (1) Å	Cell parameters from 3339 reflections
b = 10.268 (2) Å	θ = 2.4–26.4°
c = 13.771 (2) Å	µ = 1.98 mm−1
α = 80.656 (2)°	T = 298 K
β = 86.431 (2)°	Block, colorless
γ = 75.377 (2)°	0.40 × 0.10 × 0.10 mm
V = 1100.6 (3) Å3

Bruker SMART CCD diffractometer	3870 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 1.5°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
Tmin = 0.504, Tmax = 0.826	l = −16→16
8221 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.6613P] where P = (Fo2 + 2Fc2)/3
3870 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.41 e Å−3
3 restraints	Δρmin = −0.73 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	1.02842 (5)	0.72284 (4)	0.21176 (3)	0.06839 (16)
S	0.47922 (8)	0.81504 (7)	0.68119 (5)	0.03579 (18)
O1	0.5475 (2)	0.41820 (18)	0.70208 (14)	0.0414 (5)
O2	0.4093 (2)	0.90091 (19)	0.58833 (15)	0.0458 (5)
C1	0.5365 (3)	0.6416 (3)	0.66622 (19)	0.0329 (6)
C2	0.6310 (3)	0.5754 (3)	0.58705 (19)	0.0338 (6)
C3	0.7147 (3)	0.6160 (3)	0.4973 (2)	0.0351 (6)
C4	0.7098 (4)	0.7522 (3)	0.4566 (2)	0.0402 (7)
H4	0.6442	0.8226	0.4874	0.048*
C5	0.8001 (4)	0.7824 (3)	0.3723 (2)	0.0440 (7)
H5	0.7966	0.8725	0.3465	0.053*
C6	0.8974 (4)	0.6769 (4)	0.3254 (2)	0.0459 (7)
C7	0.8991 (4)	0.5447 (3)	0.3587 (2)	0.0475 (8)
H7	0.9617	0.4767	0.3246	0.057*
C8	0.8064 (3)	0.5098 (3)	0.4450 (2)	0.0395 (7)
C9	0.8021 (4)	0.3721 (3)	0.4790 (2)	0.0486 (8)
H9	0.8611	0.3048	0.4432	0.058*
C10	0.7148 (4)	0.3359 (3)	0.5616 (2)	0.0475 (7)
H10	0.7102	0.2460	0.5823	0.057*
C11	0.6323 (3)	0.4400 (3)	0.6141 (2)	0.0386 (6)
C12	0.4902 (3)	0.5427 (3)	0.7334 (2)	0.0362 (6)
C13	0.3985 (3)	0.5386 (3)	0.8286 (2)	0.0369 (6)
C14	0.3248 (4)	0.4299 (3)	0.8606 (2)	0.0483 (8)
H14	0.3349	0.3620	0.8218	0.058*
C15	0.2368 (4)	0.4225 (4)	0.9498 (2)	0.0558 (9)
H15	0.1892	0.3491	0.9708	0.067*
C16	0.2190 (4)	0.5227 (4)	1.0078 (2)	0.0545 (8)
H16	0.1571	0.5184	1.0668	0.065*
C17	0.2934 (4)	0.6293 (3)	0.9780 (2)	0.0487 (8)
H17	0.2833	0.6964	1.0176	0.058*
C18	0.3836 (4)	0.6372 (3)	0.8893 (2)	0.0438 (7)
H18	0.4345	0.7091	0.8702	0.053*
C19	0.6897 (3)	0.8360 (3)	0.6940 (2)	0.0360 (6)
C20	0.7429 (4)	0.9400 (3)	0.6352 (2)	0.0482 (8)
H20	0.6740	0.9970	0.5864	0.058*
C21	0.9020 (4)	0.9576 (4)	0.6506 (3)	0.0625 (9)
H21	0.9417	1.0254	0.6101	0.075*
C22	1.0016 (4)	0.8762 (4)	0.7248 (3)	0.0636 (10)
H22	1.1070	0.8903	0.7353	0.076*
C23	0.9455 (4)	0.7741 (4)	0.7834 (3)	0.0593 (9)
H23	1.0130	0.7191	0.8337	0.071*
C24	0.7895 (4)	0.7527 (3)	0.7681 (2)	0.0476 (7)
H24	0.7519	0.6829	0.8074	0.057*
C25	0.599 (4)	0.0294 (11)	0.9196 (17)	0.195 (5)
H25	0.6656	0.0503	0.8648	0.233*
C26	0.432 (5)	0.0346 (11)	0.9090 (14)	0.191 (5)
H26	0.3862	0.0575	0.8466	0.229*
C27	0.3318 (17)	0.0065 (14)	0.989 (3)	0.204 (5)
H27	0.2177	0.0118	0.9810	0.245*

	U11	U22	U33	U12	U13	U23
Br	0.0633 (2)	0.1022 (3)	0.0468 (2)	−0.0310 (2)	0.01776 (16)	−0.02234 (19)
S	0.0340 (4)	0.0318 (4)	0.0395 (4)	−0.0043 (3)	0.0015 (3)	−0.0064 (3)
O1	0.0450 (11)	0.0316 (10)	0.0488 (12)	−0.0119 (9)	0.0004 (9)	−0.0058 (9)
O2	0.0412 (11)	0.0394 (11)	0.0493 (12)	−0.0007 (9)	−0.0051 (9)	0.0019 (9)
C1	0.0308 (14)	0.0307 (14)	0.0374 (15)	−0.0069 (11)	−0.0039 (11)	−0.0050 (12)
C2	0.0304 (14)	0.0321 (15)	0.0382 (15)	−0.0040 (11)	−0.0042 (11)	−0.0078 (12)
C3	0.0296 (14)	0.0386 (16)	0.0379 (15)	−0.0054 (12)	−0.0032 (11)	−0.0122 (13)
C4	0.0390 (15)	0.0408 (17)	0.0406 (16)	−0.0072 (13)	0.0020 (12)	−0.0109 (13)
C5	0.0438 (16)	0.0482 (18)	0.0411 (17)	−0.0133 (14)	0.0013 (13)	−0.0081 (14)
C6	0.0370 (16)	0.067 (2)	0.0376 (16)	−0.0148 (15)	0.0028 (13)	−0.0161 (15)
C7	0.0379 (16)	0.061 (2)	0.0458 (18)	−0.0050 (15)	−0.0007 (13)	−0.0255 (16)
C8	0.0324 (14)	0.0437 (17)	0.0432 (16)	−0.0031 (13)	−0.0054 (12)	−0.0172 (14)
C9	0.0453 (17)	0.0418 (18)	0.059 (2)	−0.0006 (14)	−0.0038 (15)	−0.0248 (15)
C10	0.0506 (18)	0.0345 (17)	0.058 (2)	−0.0077 (14)	−0.0061 (15)	−0.0115 (15)
C11	0.0372 (15)	0.0357 (16)	0.0438 (16)	−0.0082 (13)	−0.0051 (13)	−0.0081 (13)
C12	0.0324 (14)	0.0357 (16)	0.0409 (16)	−0.0086 (12)	−0.0059 (12)	−0.0050 (13)
C13	0.0325 (14)	0.0393 (16)	0.0380 (16)	−0.0101 (12)	−0.0064 (12)	0.0008 (13)
C14	0.0516 (18)	0.0526 (19)	0.0446 (18)	−0.0212 (15)	−0.0074 (14)	−0.0030 (15)
C15	0.058 (2)	0.062 (2)	0.0495 (19)	−0.0296 (17)	0.0002 (16)	0.0068 (17)
C16	0.0504 (19)	0.070 (2)	0.0393 (17)	−0.0151 (17)	0.0028 (14)	0.0013 (17)
C17	0.0518 (18)	0.0525 (19)	0.0388 (17)	−0.0080 (15)	−0.0019 (14)	−0.0061 (14)
C18	0.0456 (17)	0.0441 (17)	0.0413 (17)	−0.0136 (14)	−0.0035 (13)	−0.0004 (14)
C19	0.0354 (14)	0.0325 (15)	0.0400 (16)	−0.0052 (12)	−0.0016 (12)	−0.0097 (12)
C20	0.0523 (19)	0.0350 (17)	0.058 (2)	−0.0147 (14)	−0.0078 (15)	0.0010 (14)
C21	0.059 (2)	0.050 (2)	0.084 (3)	−0.0277 (18)	0.0003 (19)	−0.0043 (19)
C22	0.0402 (18)	0.060 (2)	0.096 (3)	−0.0156 (17)	−0.0098 (19)	−0.018 (2)
C23	0.0481 (19)	0.058 (2)	0.069 (2)	−0.0060 (17)	−0.0187 (17)	−0.0054 (18)
C24	0.0461 (18)	0.0440 (18)	0.0513 (19)	−0.0105 (15)	−0.0059 (14)	−0.0023 (15)
C25	0.28 (2)	0.110 (6)	0.176 (15)	0.006 (9)	0.013 (10)	−0.058 (7)
C26	0.268 (19)	0.109 (6)	0.179 (15)	0.019 (10)	−0.068 (14)	−0.052 (8)
C27	0.211 (11)	0.117 (7)	0.281 (16)	0.002 (8)	−0.05 (2)	−0.074 (10)

Br—C6	1.902 (3)	C14—C15	1.385 (4)
S—O2	1.486 (2)	C14—H14	0.9300
S—C1	1.767 (3)	C15—C16	1.376 (5)
S—C19	1.805 (3)	C15—H15	0.9300
O1—C11	1.371 (3)	C16—C17	1.375 (4)
O1—C12	1.375 (3)	C16—H16	0.9300
C1—C12	1.369 (4)	C17—C18	1.388 (4)
C1—C2	1.455 (4)	C17—H17	0.9300
C2—C11	1.377 (4)	C18—H18	0.9300
C2—C3	1.428 (4)	C19—C20	1.376 (4)
C3—C4	1.411 (4)	C19—C24	1.379 (4)
C3—C8	1.429 (4)	C20—C21	1.387 (4)
C4—C5	1.370 (4)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.373 (5)
C5—C6	1.396 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.371 (5)
C6—C7	1.357 (4)	C22—H22	0.9300
C7—C8	1.414 (4)	C23—C24	1.379 (4)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.423 (4)	C24—H24	0.9300
C9—C10	1.354 (4)	C25—C26	1.37 (5)
C9—H9	0.9300	C25—C27i	1.37 (4)
C10—C11	1.396 (4)	C25—H25	0.9300
C10—H10	0.9300	C26—C27	1.37 (4)
C12—C13	1.468 (4)	C26—H26	0.9300
C13—C18	1.391 (4)	C27—C25i	1.37 (4)
C13—C14	1.396 (4)	C27—H27	0.9300
O2—S—C1	110.10 (12)	C15—C14—C13	120.4 (3)
O2—S—C19	107.93 (12)	C15—C14—H14	119.8
C1—S—C19	97.94 (12)	C13—C14—H14	119.8
C11—O1—C12	106.8 (2)	C16—C15—C14	120.7 (3)
C12—C1—C2	107.4 (2)	C16—C15—H15	119.7
C12—C1—S	122.2 (2)	C14—C15—H15	119.7
C2—C1—S	130.4 (2)	C17—C16—C15	119.6 (3)
C11—C2—C3	119.0 (2)	C17—C16—H16	120.2
C11—C2—C1	104.3 (2)	C15—C16—H16	120.2
C3—C2—C1	136.7 (2)	C16—C17—C18	120.3 (3)
C4—C3—C2	124.6 (2)	C16—C17—H17	119.8
C4—C3—C8	118.6 (3)	C18—C17—H17	119.8
C2—C3—C8	116.7 (3)	C17—C18—C13	120.7 (3)
C5—C4—C3	121.0 (3)	C17—C18—H18	119.7
C5—C4—H4	119.5	C13—C18—H18	119.7
C3—C4—H4	119.5	C20—C19—C24	121.2 (3)
C4—C5—C6	119.6 (3)	C20—C19—S	119.9 (2)
C4—C5—H5	120.2	C24—C19—S	118.7 (2)
C6—C5—H5	120.2	C19—C20—C21	118.4 (3)
C7—C6—C5	121.6 (3)	C19—C20—H20	120.8
C7—C6—Br	120.2 (2)	C21—C20—H20	120.8
C5—C6—Br	118.2 (2)	C22—C21—C20	120.8 (3)
C6—C7—C8	120.4 (3)	C22—C21—H21	119.6
C6—C7—H7	119.8	C20—C21—H21	119.6
C8—C7—H7	119.8	C23—C22—C21	119.9 (3)
C7—C8—C9	121.1 (3)	C23—C22—H22	120.0
C7—C8—C3	118.6 (3)	C21—C22—H22	120.0
C9—C8—C3	120.3 (3)	C22—C23—C24	120.3 (3)
C10—C9—C8	122.2 (3)	C22—C23—H23	119.8
C10—C9—H9	118.9	C24—C23—H23	119.8
C8—C9—H9	118.9	C23—C24—C19	119.3 (3)
C9—C10—C11	116.7 (3)	C23—C24—H24	120.3
C9—C10—H10	121.7	C19—C24—H24	120.3
C11—C10—H10	121.7	C26—C25—C27i	119.8 (11)
O1—C11—C2	111.6 (2)	C26—C25—H25	120.1
O1—C11—C10	123.5 (3)	C27i—C25—H25	120.1
C2—C11—C10	124.9 (3)	C25—C26—C27	120.9 (12)
C1—C12—O1	109.9 (2)	C25—C26—H26	119.5
C1—C12—C13	135.7 (3)	C27—C26—H26	119.5
O1—C12—C13	114.5 (2)	C26—C27—C25i	119.3 (11)
C18—C13—C14	118.3 (3)	C26—C27—H27	120.4
C18—C13—C12	123.1 (3)	C25i—C27—H27	120.4
C14—C13—C12	118.6 (3)
O2—S—C1—C12	−132.3 (2)	C9—C10—C11—O1	−176.0 (3)
C19—S—C1—C12	115.2 (2)	C9—C10—C11—C2	1.2 (4)
O2—S—C1—C2	46.3 (3)	C2—C1—C12—O1	−0.6 (3)
C19—S—C1—C2	−66.2 (3)	S—C1—C12—O1	178.36 (17)
C12—C1—C2—C11	0.4 (3)	C2—C1—C12—C13	178.5 (3)
S—C1—C2—C11	−178.4 (2)	S—C1—C12—C13	−2.6 (4)
C12—C1—C2—C3	−179.2 (3)	C11—O1—C12—C1	0.5 (3)
S—C1—C2—C3	2.0 (5)	C11—O1—C12—C13	−178.8 (2)
C11—C2—C3—C4	173.8 (3)	C1—C12—C13—C18	−22.7 (5)
C1—C2—C3—C4	−6.6 (5)	O1—C12—C13—C18	156.3 (3)
C11—C2—C3—C8	−4.8 (4)	C1—C12—C13—C14	158.2 (3)
C1—C2—C3—C8	174.8 (3)	O1—C12—C13—C14	−22.7 (3)
C2—C3—C4—C5	177.0 (3)	C18—C13—C14—C15	1.1 (4)
C8—C3—C4—C5	−4.4 (4)	C12—C13—C14—C15	−179.8 (3)
C3—C4—C5—C6	0.6 (4)	C13—C14—C15—C16	0.7 (5)
C4—C5—C6—C7	3.0 (4)	C14—C15—C16—C17	−1.8 (5)
C4—C5—C6—Br	−177.4 (2)	C15—C16—C17—C18	1.1 (5)
C5—C6—C7—C8	−2.4 (4)	C16—C17—C18—C13	0.7 (5)
Br—C6—C7—C8	177.9 (2)	C14—C13—C18—C17	−1.8 (4)
C6—C7—C8—C9	177.7 (3)	C12—C13—C18—C17	179.1 (3)
C6—C7—C8—C3	−1.5 (4)	O2—S—C19—C20	13.1 (3)
C4—C3—C8—C7	4.9 (4)	C1—S—C19—C20	127.3 (2)
C2—C3—C8—C7	−176.4 (2)	O2—S—C19—C24	−171.6 (2)
C4—C3—C8—C9	−174.4 (3)	C1—S—C19—C24	−57.4 (2)
C2—C3—C8—C9	4.3 (4)	C24—C19—C20—C21	1.5 (5)
C7—C8—C9—C10	179.7 (3)	S—C19—C20—C21	176.7 (2)
C3—C8—C9—C10	−1.0 (4)	C19—C20—C21—C22	−2.2 (5)
C8—C9—C10—C11	−1.7 (4)	C20—C21—C22—C23	1.4 (6)
C12—O1—C11—C2	−0.3 (3)	C21—C22—C23—C24	0.0 (6)
C12—O1—C11—C10	177.2 (3)	C22—C23—C24—C19	−0.7 (5)
C3—C2—C11—O1	179.7 (2)	C20—C19—C24—C23	0.0 (5)
C1—C2—C11—O1	0.0 (3)	S—C19—C24—C23	−175.3 (2)
C3—C2—C11—C10	2.2 (4)	C27i—C25—C26—C27	1.1 (19)
C1—C2—C11—C10	−177.5 (3)	C25—C26—C27—C25i	−1.1 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···Cg1ii	0.93	2.87	3.740 (4)	156
C20—H20···O2iii	0.93	2.52	3.392 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯Cg1i	0.93	2.87	3.740 (4)	156
C20—H20⋯O2ii	0.93	2.52	3.392 (4)	155

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C13–C18 benzene ring.