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

In the title compound, C(24)H(15)FO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 19.43 (4)° with the mean plane of the naphtho-furan fragment. The dihedral angle between the phenyl ring and the mean plane of the naphtho-furan fragment is 85.83 (4)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Goel & Dixit (2004 ▶); Hagiwara et al. (1999 ▶); Piloto et al. (2005 ▶). For structural studies of related 2-ar­yl-1-(phenyl­sulfin­yl)naphtho­[2,1-b]furan derivatives, see: Choi et al. (2009a ▶,b ▶).

Experimental

Crystal data

C24H15FO2S

M = 386.42

Triclinic,

a = 7.2853 (2) Å

b = 10.1619 (3) Å

c = 12.3137 (4) Å

α = 103.439 (2)°

β = 90.486 (2)°

γ = 96.422 (2)°

V = 880.53 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.29 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.941, T max = 0.954

16660 measured reflections

4392 independent reflections

3675 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.05

4392 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811034155/qm2024sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034155/qm2024Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034155/qm2024Isup3.cml

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

C24H15FO2S	Z = 2
Mr = 386.42	F(000) = 400
Triclinic, P1	Dx = 1.457 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2853 (2) Å	Cell parameters from 5489 reflections
b = 10.1619 (3) Å	θ = 2.8–28.2°
c = 12.3137 (4) Å	µ = 0.21 mm−1
α = 103.439 (2)°	T = 173 K
β = 90.486 (2)°	Block, colourless
γ = 96.422 (2)°	0.29 × 0.26 × 0.22 mm
V = 880.53 (5) Å3

Bruker SMART APEXII CCD diffractometer	4392 independent reflections
Radiation source: rotating anode	3675 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.037
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.941, Tmax = 0.954	l = −16→16
16660 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.055P)2 + 0.2885P] where P = (Fo2 + 2Fc2)/3
4392 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.38 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
S1	0.45928 (5)	0.63116 (4)	0.30349 (3)	0.02511 (11)
O1	0.20787 (15)	0.47766 (10)	0.53486 (8)	0.0251 (2)
O2	0.60815 (15)	0.55620 (12)	0.24620 (9)	0.0325 (3)
F1	0.30192 (18)	1.08991 (10)	0.78434 (9)	0.0525 (3)
C1	0.3299 (2)	0.52987 (14)	0.38112 (11)	0.0227 (3)
C2	0.2802 (2)	0.38352 (14)	0.35730 (12)	0.0232 (3)
C3	0.2860 (2)	0.27066 (14)	0.26339 (12)	0.0241 (3)
C4	0.3429 (2)	0.28088 (15)	0.15649 (12)	0.0284 (3)
H4	0.3837	0.3678	0.1435	0.034*
C5	0.3403 (3)	0.16705 (17)	0.07079 (13)	0.0350 (4)
H5	0.3778	0.1759	−0.0011	0.042*
C6	0.2828 (3)	0.03789 (17)	0.08849 (14)	0.0396 (4)
H6	0.2823	−0.0404	0.0287	0.047*
C7	0.2276 (3)	0.02390 (16)	0.19071 (14)	0.0363 (4)
H7	0.1896	−0.0645	0.2017	0.044*
C8	0.2257 (2)	0.13876 (15)	0.28111 (13)	0.0277 (3)
C9	0.1638 (2)	0.12265 (16)	0.38691 (13)	0.0307 (3)
H9	0.1278	0.0334	0.3966	0.037*
C10	0.1545 (2)	0.23082 (15)	0.47463 (13)	0.0285 (3)
H10	0.1118	0.2198	0.5450	0.034*
C11	0.2112 (2)	0.35935 (14)	0.45543 (12)	0.0244 (3)
C13	0.2903 (2)	0.71658 (15)	0.56465 (11)	0.0246 (3)
C14	0.3198 (2)	0.83664 (15)	0.52753 (13)	0.0292 (3)
H14	0.3354	0.8320	0.4503	0.035*
C15	0.3266 (2)	0.96241 (16)	0.60182 (14)	0.0327 (3)
H15	0.3505	1.0441	0.5768	0.039*
C16	0.2981 (2)	0.96647 (16)	0.71221 (14)	0.0346 (4)
C17	0.2644 (3)	0.85122 (18)	0.75213 (13)	0.0376 (4)
H17	0.2433	0.8575	0.8291	0.045*
C18	0.2618 (2)	0.72569 (16)	0.67816 (12)	0.0315 (3)
H18	0.2404	0.6449	0.7047	0.038*
C19	0.2902 (2)	0.63310 (14)	0.19726 (12)	0.0243 (3)
C12	0.2825 (2)	0.58147 (14)	0.48933 (12)	0.0238 (3)
C20	0.3553 (2)	0.63478 (15)	0.09205 (12)	0.0284 (3)
H20	0.4813	0.6249	0.0766	0.034*
C21	0.2352 (2)	0.65096 (16)	0.00974 (13)	0.0341 (4)
H21	0.2779	0.6505	−0.0630	0.041*
C22	0.0532 (2)	0.66772 (17)	0.03334 (15)	0.0365 (4)
H22	−0.0281	0.6813	−0.0228	0.044*
C23	−0.0115 (2)	0.66481 (16)	0.13781 (15)	0.0352 (4)
H23	−0.1373	0.6754	0.1531	0.042*
C24	0.1062 (2)	0.64650 (15)	0.22047 (13)	0.0297 (3)
H24	0.0616	0.6431	0.2922	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.02566 (19)	0.02638 (19)	0.02358 (18)	0.00069 (14)	0.00323 (13)	0.00750 (13)
O1	0.0290 (5)	0.0258 (5)	0.0215 (5)	0.0044 (4)	0.0048 (4)	0.0068 (4)
O2	0.0266 (6)	0.0420 (6)	0.0325 (6)	0.0091 (5)	0.0074 (5)	0.0135 (5)
F1	0.0772 (8)	0.0330 (5)	0.0407 (6)	0.0154 (5)	−0.0018 (6)	−0.0089 (4)
C1	0.0234 (7)	0.0237 (6)	0.0214 (6)	0.0024 (5)	0.0024 (5)	0.0064 (5)
C2	0.0213 (6)	0.0250 (7)	0.0242 (7)	0.0029 (5)	0.0002 (5)	0.0074 (5)
C3	0.0223 (7)	0.0248 (7)	0.0252 (7)	0.0037 (5)	0.0000 (5)	0.0052 (5)
C4	0.0328 (8)	0.0270 (7)	0.0255 (7)	0.0038 (6)	0.0011 (6)	0.0062 (6)
C5	0.0454 (10)	0.0336 (8)	0.0247 (7)	0.0057 (7)	0.0028 (7)	0.0039 (6)
C6	0.0537 (11)	0.0273 (8)	0.0322 (8)	0.0022 (8)	−0.0007 (8)	−0.0027 (6)
C7	0.0447 (10)	0.0239 (7)	0.0377 (9)	0.0003 (7)	−0.0002 (7)	0.0040 (6)
C8	0.0266 (7)	0.0262 (7)	0.0300 (7)	0.0030 (6)	−0.0008 (6)	0.0064 (6)
C9	0.0310 (8)	0.0261 (7)	0.0367 (8)	0.0004 (6)	0.0023 (7)	0.0122 (6)
C10	0.0279 (7)	0.0313 (7)	0.0293 (7)	0.0037 (6)	0.0054 (6)	0.0131 (6)
C11	0.0236 (7)	0.0257 (7)	0.0240 (7)	0.0045 (6)	0.0023 (5)	0.0054 (5)
C13	0.0226 (7)	0.0275 (7)	0.0232 (7)	0.0057 (6)	0.0011 (5)	0.0039 (5)
C14	0.0318 (8)	0.0289 (7)	0.0265 (7)	0.0045 (6)	0.0044 (6)	0.0048 (6)
C15	0.0331 (8)	0.0261 (7)	0.0378 (8)	0.0038 (6)	0.0021 (7)	0.0048 (6)
C16	0.0377 (9)	0.0287 (8)	0.0328 (8)	0.0102 (7)	−0.0034 (7)	−0.0051 (6)
C17	0.0506 (10)	0.0412 (9)	0.0218 (7)	0.0167 (8)	0.0005 (7)	0.0036 (6)
C18	0.0396 (9)	0.0322 (8)	0.0243 (7)	0.0109 (7)	0.0002 (6)	0.0069 (6)
C19	0.0273 (7)	0.0208 (6)	0.0254 (7)	0.0032 (5)	0.0015 (6)	0.0064 (5)
C12	0.0228 (7)	0.0265 (7)	0.0233 (6)	0.0033 (6)	0.0009 (5)	0.0084 (5)
C20	0.0282 (7)	0.0304 (7)	0.0281 (7)	0.0041 (6)	0.0045 (6)	0.0096 (6)
C21	0.0400 (9)	0.0350 (8)	0.0292 (8)	0.0010 (7)	0.0007 (7)	0.0129 (6)
C22	0.0361 (9)	0.0332 (8)	0.0409 (9)	0.0022 (7)	−0.0092 (7)	0.0112 (7)
C23	0.0258 (8)	0.0317 (8)	0.0475 (9)	0.0041 (6)	0.0004 (7)	0.0082 (7)
C24	0.0299 (8)	0.0270 (7)	0.0319 (8)	0.0044 (6)	0.0062 (6)	0.0058 (6)

S1—O2	1.4840 (11)	C10—H10	0.9500
S1—C1	1.7655 (15)	C13—C14	1.395 (2)
S1—C19	1.7939 (15)	C13—C18	1.398 (2)
O1—C11	1.3650 (16)	C13—C12	1.4623 (19)
O1—C12	1.3690 (17)	C14—C15	1.384 (2)
F1—C16	1.3554 (17)	C14—H14	0.9500
C1—C12	1.3761 (19)	C15—C16	1.369 (2)
C1—C2	1.4505 (19)	C15—H15	0.9500
C2—C11	1.376 (2)	C16—C17	1.371 (2)
C2—C3	1.4316 (19)	C17—C18	1.383 (2)
C3—C4	1.407 (2)	C17—H17	0.9500
C3—C8	1.429 (2)	C18—H18	0.9500
C4—C5	1.371 (2)	C19—C20	1.387 (2)
C4—H4	0.9500	C19—C24	1.388 (2)
C5—C6	1.399 (2)	C20—C21	1.384 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.358 (2)	C21—C22	1.380 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.415 (2)	C22—C23	1.379 (3)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.421 (2)	C23—C24	1.384 (2)
C9—C10	1.359 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C10—C11	1.399 (2)
O2—S1—C1	109.66 (7)	C14—C13—C12	122.77 (13)
O2—S1—C19	106.56 (7)	C18—C13—C12	118.58 (14)
C1—S1—C19	100.32 (7)	C15—C14—C13	120.83 (14)
C11—O1—C12	107.08 (11)	C15—C14—H14	119.6
C12—C1—C2	106.96 (12)	C13—C14—H14	119.6
C12—C1—S1	122.10 (11)	C16—C15—C14	118.52 (15)
C2—C1—S1	130.23 (11)	C16—C15—H15	120.7
C11—C2—C3	118.81 (13)	C14—C15—H15	120.7
C11—C2—C1	104.59 (12)	F1—C16—C15	118.28 (15)
C3—C2—C1	136.60 (13)	F1—C16—C17	119.01 (15)
C4—C3—C8	118.60 (13)	C15—C16—C17	122.71 (14)
C4—C3—C2	124.99 (13)	C16—C17—C18	118.67 (15)
C8—C3—C2	116.40 (13)	C16—C17—H17	120.7
C5—C4—C3	120.89 (15)	C18—C17—H17	120.7
C5—C4—H4	119.6	C17—C18—C13	120.61 (15)
C3—C4—H4	119.6	C17—C18—H18	119.7
C4—C5—C6	120.45 (15)	C13—C18—H18	119.7
C4—C5—H5	119.8	C20—C19—C24	120.76 (14)
C6—C5—H5	119.8	C20—C19—S1	116.63 (12)
C7—C6—C5	120.35 (15)	C24—C19—S1	122.28 (11)
C7—C6—H6	119.8	O1—C12—C1	109.83 (12)
C5—C6—H6	119.8	O1—C12—C13	114.08 (12)
C6—C7—C8	121.09 (15)	C1—C12—C13	136.09 (14)
C6—C7—H7	119.5	C21—C20—C19	119.39 (15)
C8—C7—H7	119.5	C21—C20—H20	120.3
C7—C8—C9	120.40 (14)	C19—C20—H20	120.3
C7—C8—C3	118.61 (14)	C22—C21—C20	120.00 (15)
C9—C8—C3	120.99 (13)	C22—C21—H21	120.0
C10—C9—C8	122.07 (14)	C20—C21—H21	120.0
C10—C9—H9	119.0	C23—C22—C21	120.45 (15)
C8—C9—H9	119.0	C23—C22—H22	119.8
C9—C10—C11	116.22 (14)	C21—C22—H22	119.8
C9—C10—H10	121.9	C22—C23—C24	120.23 (15)
C11—C10—H10	121.9	C22—C23—H23	119.9
O1—C11—C2	111.49 (12)	C24—C23—H23	119.9
O1—C11—C10	123.09 (13)	C23—C24—C19	119.14 (15)
C2—C11—C10	125.40 (13)	C23—C24—H24	120.4
C14—C13—C18	118.63 (13)	C19—C24—H24	120.4
O2—S1—C1—C12	134.17 (12)	C9—C10—C11—C2	−2.3 (2)
C19—S1—C1—C12	−113.94 (13)	C18—C13—C14—C15	2.0 (2)
O2—S1—C1—C2	−34.89 (15)	C12—C13—C14—C15	−179.88 (14)
C19—S1—C1—C2	77.00 (14)	C13—C14—C15—C16	−2.0 (2)
C12—C1—C2—C11	−1.64 (16)	C14—C15—C16—F1	−178.94 (15)
S1—C1—C2—C11	168.69 (12)	C14—C15—C16—C17	0.4 (3)
C12—C1—C2—C3	178.01 (16)	F1—C16—C17—C18	−179.64 (15)
S1—C1—C2—C3	−11.7 (3)	C15—C16—C17—C18	1.0 (3)
C11—C2—C3—C4	176.20 (14)	C16—C17—C18—C13	−0.9 (3)
C1—C2—C3—C4	−3.4 (3)	C14—C13—C18—C17	−0.6 (2)
C11—C2—C3—C8	−2.6 (2)	C12—C13—C18—C17	−178.74 (15)
C1—C2—C3—C8	177.77 (15)	O2—S1—C19—C20	−31.41 (13)
C8—C3—C4—C5	0.2 (2)	C1—S1—C19—C20	−145.68 (12)
C2—C3—C4—C5	−178.65 (15)	O2—S1—C19—C24	155.11 (12)
C3—C4—C5—C6	−0.7 (3)	C1—S1—C19—C24	40.84 (13)
C4—C5—C6—C7	0.5 (3)	C11—O1—C12—C1	1.02 (16)
C5—C6—C7—C8	0.4 (3)	C11—O1—C12—C13	−179.62 (12)
C6—C7—C8—C9	178.66 (16)	C2—C1—C12—O1	0.40 (16)
C6—C7—C8—C3	−1.0 (3)	S1—C1—C12—O1	−170.89 (10)
C4—C3—C8—C7	0.7 (2)	C2—C1—C12—C13	−178.75 (16)
C2—C3—C8—C7	179.59 (14)	S1—C1—C12—C13	10.0 (2)
C4—C3—C8—C9	−178.94 (14)	C14—C13—C12—O1	−164.53 (14)
C2—C3—C8—C9	0.0 (2)	C18—C13—C12—O1	13.57 (19)
C7—C8—C9—C10	−177.87 (16)	C14—C13—C12—C1	14.6 (3)
C3—C8—C9—C10	1.7 (2)	C18—C13—C12—C1	−167.30 (17)
C8—C9—C10—C11	−0.7 (2)	C24—C19—C20—C21	0.4 (2)
C12—O1—C11—C2	−2.16 (16)	S1—C19—C20—C21	−173.16 (12)
C12—O1—C11—C10	176.51 (14)	C19—C20—C21—C22	1.2 (2)
C3—C2—C11—O1	−177.37 (12)	C20—C21—C22—C23	−1.8 (2)
C1—C2—C11—O1	2.34 (16)	C21—C22—C23—C24	0.7 (3)
C3—C2—C11—C10	4.0 (2)	C22—C23—C24—C19	0.9 (2)
C1—C2—C11—C10	−176.29 (14)	C20—C19—C24—C23	−1.5 (2)
C9—C10—C11—O1	179.24 (13)	S1—C19—C24—C23	171.74 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O2i	0.95	2.53	3.277 (2)	136.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O2i	0.95	2.53	3.277 (2)	136

Symmetry code: (i) .