1-Ethyl-sulfinyl-2-(4-iodo-phen-yl)naphtho-[2,1-b]furan.

In the title compound, C(20)H(15)IO(2)S, the 4-iodo-phenyl ring makes a dihedral angle of 44.21 (7)° with the plane of the naphtho-furan fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶). For the structures of related 2-aryl-1-(methyl­sulfin­yl)naphtho­[2,1-b]furan derivatives, see: Choi et al. (2006 ▶, 2010 ▶).

Experimental

Crystal data

C20H15IO2S

M = 446.28

Monoclinic,

a = 9.1240 (5) Å

b = 12.4302 (6) Å

c = 15.8520 (8) Å

β = 105.899 (2)°

V = 1729.05 (15) Å3

Z = 4

Mo Kα radiation

μ = 1.98 mm−1

T = 174 K

0.27 × 0.23 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.619, T max = 0.825

14865 measured reflections

3937 independent reflections

3511 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.084

S = 1.09

3937 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −1.28 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 datablocks I. DOI: 10.1107/S1600536810029144/ds2042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029144/ds2042Isup2.hkl

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

C20H15IO2S	F(000) = 880
Mr = 446.28	Dx = 1.714 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1240 (5) Å	Cell parameters from 3937 reflections
b = 12.4302 (6) Å	θ = 2.1–27.5°
c = 15.8520 (8) Å	µ = 1.98 mm−1
β = 105.899 (2)°	T = 174 K
V = 1729.05 (15) Å3	Block, colourless
Z = 4	0.27 × 0.23 × 0.10 mm

Bruker SMART APEXII CCD diffractometer	3937 independent reflections
Radiation source: rotating anode	3511 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −16→13
Tmin = 0.619, Tmax = 0.825	l = −20→19
14865 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F2) = 0.084	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.6527P] where P = (Fo2 + 2Fc2)/3
3937 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −1.28 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
I	0.00380 (2)	0.277333 (14)	0.601089 (11)	0.03776 (9)
S	0.45899 (6)	0.76556 (4)	0.55355 (4)	0.02160 (13)
O1	0.70925 (17)	0.52550 (13)	0.67638 (10)	0.0239 (3)
O2	0.48599 (18)	0.87424 (14)	0.59467 (10)	0.0285 (4)
C1	0.6068 (2)	0.67815 (18)	0.60936 (13)	0.0205 (4)
C2	0.7714 (2)	0.69096 (19)	0.63592 (13)	0.0213 (4)
C3	0.8780 (3)	0.77275 (18)	0.62844 (15)	0.0238 (5)
C4	0.8389 (3)	0.8777 (2)	0.59683 (15)	0.0275 (5)
H4	0.7348	0.8988	0.5798	0.033*
C5	0.9491 (3)	0.9498 (2)	0.59032 (17)	0.0364 (6)
H5	0.9206	1.0196	0.5674	0.044*
C6	1.1048 (3)	0.9209 (3)	0.61747 (18)	0.0406 (7)
H6	1.1807	0.9712	0.6128	0.049*
C7	1.1455 (3)	0.8211 (3)	0.65028 (16)	0.0359 (6)
H7	1.2505	0.8026	0.6688	0.043*
C8	1.0358 (3)	0.7438 (2)	0.65766 (15)	0.0289 (5)
C9	1.0814 (3)	0.6397 (2)	0.69298 (15)	0.0311 (5)
H9	1.1868	0.6221	0.7095	0.037*
C10	0.9800 (3)	0.5649 (2)	0.70387 (15)	0.0292 (5)
H10	1.0113	0.4967	0.7297	0.035*
C11	0.8256 (2)	0.59444 (19)	0.67454 (14)	0.0230 (4)
C12	0.5766 (2)	0.57813 (18)	0.63581 (13)	0.0206 (4)
C13	0.4390 (2)	0.51475 (17)	0.62874 (13)	0.0203 (4)
C14	0.4302 (3)	0.44819 (18)	0.69846 (14)	0.0242 (5)
H14	0.5106	0.4485	0.7512	0.029*
C15	0.3056 (3)	0.38198 (19)	0.69132 (15)	0.0259 (5)
H15	0.3000	0.3372	0.7389	0.031*
C16	0.1890 (3)	0.38172 (18)	0.61392 (14)	0.0234 (4)
C17	0.1941 (2)	0.44740 (18)	0.54422 (14)	0.0234 (4)
H17	0.1127	0.4469	0.4918	0.028*
C18	0.3187 (2)	0.51365 (18)	0.55162 (14)	0.0225 (4)
H18	0.3227	0.5589	0.5040	0.027*
C19	0.5111 (3)	0.77015 (18)	0.45098 (15)	0.0274 (5)
H19A	0.6212	0.7860	0.4630	0.033*
H19B	0.4914	0.6992	0.4216	0.033*
C20	0.4199 (4)	0.8559 (2)	0.39126 (19)	0.0442 (7)
H20A	0.3111	0.8389	0.3779	0.066*
H20B	0.4506	0.8585	0.3367	0.066*
H20C	0.4391	0.9260	0.4206	0.066*

	U11	U22	U33	U12	U13	U23
I	0.04151 (13)	0.03477 (14)	0.03818 (12)	−0.01862 (7)	0.01291 (8)	−0.00299 (6)
S	0.0202 (3)	0.0193 (3)	0.0249 (3)	0.0019 (2)	0.0054 (2)	−0.0001 (2)
O1	0.0217 (7)	0.0252 (8)	0.0241 (8)	0.0026 (6)	0.0052 (6)	0.0041 (6)
O2	0.0315 (9)	0.0215 (9)	0.0344 (9)	0.0020 (7)	0.0120 (7)	−0.0055 (6)
C1	0.0198 (10)	0.0248 (11)	0.0174 (9)	0.0003 (9)	0.0061 (7)	−0.0011 (8)
C2	0.0201 (10)	0.0270 (11)	0.0173 (10)	0.0010 (9)	0.0059 (7)	−0.0020 (8)
C3	0.0231 (11)	0.0301 (13)	0.0204 (10)	−0.0055 (9)	0.0097 (8)	−0.0048 (9)
C4	0.0302 (11)	0.0277 (12)	0.0269 (11)	−0.0060 (10)	0.0118 (9)	−0.0060 (9)
C5	0.0441 (15)	0.0345 (15)	0.0338 (13)	−0.0145 (12)	0.0158 (11)	−0.0081 (11)
C6	0.0355 (14)	0.0529 (18)	0.0376 (14)	−0.0217 (13)	0.0169 (11)	−0.0139 (13)
C7	0.0257 (12)	0.0539 (18)	0.0304 (13)	−0.0126 (12)	0.0114 (9)	−0.0121 (12)
C8	0.0221 (10)	0.0446 (14)	0.0212 (11)	−0.0045 (10)	0.0077 (8)	−0.0077 (10)
C9	0.0195 (10)	0.0498 (16)	0.0232 (11)	0.0065 (11)	0.0045 (8)	−0.0061 (11)
C10	0.0234 (11)	0.0410 (14)	0.0221 (11)	0.0094 (10)	0.0044 (8)	−0.0018 (10)
C11	0.0206 (10)	0.0285 (12)	0.0201 (10)	0.0004 (9)	0.0060 (7)	−0.0013 (8)
C12	0.0205 (10)	0.0217 (11)	0.0193 (10)	0.0020 (8)	0.0048 (7)	−0.0007 (8)
C13	0.0235 (10)	0.0186 (10)	0.0203 (10)	0.0004 (8)	0.0085 (8)	−0.0001 (8)
C14	0.0264 (11)	0.0254 (12)	0.0198 (10)	0.0012 (9)	0.0045 (8)	0.0012 (8)
C15	0.0330 (12)	0.0230 (12)	0.0232 (11)	−0.0001 (9)	0.0105 (9)	0.0035 (9)
C16	0.0264 (11)	0.0195 (11)	0.0265 (11)	−0.0031 (9)	0.0110 (8)	−0.0029 (9)
C17	0.0237 (10)	0.0262 (11)	0.0205 (10)	0.0012 (9)	0.0065 (8)	−0.0024 (9)
C18	0.0261 (10)	0.0236 (11)	0.0191 (10)	0.0006 (9)	0.0083 (8)	0.0029 (8)
C19	0.0360 (13)	0.0250 (13)	0.0207 (11)	0.0006 (10)	0.0067 (9)	0.0010 (9)
C20	0.0500 (17)	0.0410 (16)	0.0373 (15)	0.0042 (14)	0.0045 (12)	0.0157 (12)

I—C16	2.096 (2)	C9—C10	1.356 (4)
S—O2	1.4908 (18)	C9—H9	0.9500
S—C1	1.769 (2)	C10—C11	1.406 (3)
S—C19	1.816 (3)	C10—H10	0.9500
O1—C11	1.371 (3)	C12—C13	1.460 (3)
O1—C12	1.371 (2)	C13—C14	1.401 (3)
C1—C12	1.364 (3)	C13—C18	1.402 (3)
C1—C2	1.453 (3)	C14—C15	1.382 (3)
C2—C11	1.376 (3)	C14—H14	0.9500
C2—C3	1.434 (3)	C15—C16	1.386 (3)
C3—C4	1.407 (3)	C15—H15	0.9500
C3—C8	1.432 (3)	C16—C17	1.385 (3)
C4—C5	1.372 (4)	C17—C18	1.382 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.413 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.515 (3)
C6—C7	1.358 (4)	C19—H19A	0.9900
C6—H6	0.9500	C19—H19B	0.9900
C7—C8	1.414 (4)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.426 (4)	C20—H20C	0.9800
O2—S—C1	109.02 (10)	O1—C11—C10	122.8 (2)
O2—S—C19	108.10 (10)	C2—C11—C10	125.5 (2)
C1—S—C19	96.68 (11)	C1—C12—O1	110.63 (18)
C11—O1—C12	106.32 (17)	C1—C12—C13	135.2 (2)
C12—C1—C2	106.90 (19)	O1—C12—C13	114.11 (18)
C12—C1—S	121.54 (16)	C14—C13—C18	118.8 (2)
C2—C1—S	131.56 (17)	C14—C13—C12	119.50 (18)
C11—C2—C3	119.1 (2)	C18—C13—C12	121.60 (19)
C11—C2—C1	104.5 (2)	C15—C14—C13	120.7 (2)
C3—C2—C1	136.4 (2)	C15—C14—H14	119.6
C4—C3—C8	118.8 (2)	C13—C14—H14	119.6
C4—C3—C2	125.1 (2)	C14—C15—C16	119.2 (2)
C8—C3—C2	116.1 (2)	C14—C15—H15	120.4
C5—C4—C3	120.8 (2)	C16—C15—H15	120.4
C5—C4—H4	119.6	C17—C16—C15	121.3 (2)
C3—C4—H4	119.6	C17—C16—I	119.33 (16)
C4—C5—C6	120.5 (3)	C15—C16—I	119.35 (17)
C4—C5—H5	119.7	C18—C17—C16	119.3 (2)
C6—C5—H5	119.7	C18—C17—H17	120.3
C7—C6—C5	119.7 (2)	C16—C17—H17	120.3
C7—C6—H6	120.2	C17—C18—C13	120.6 (2)
C5—C6—H6	120.2	C17—C18—H18	119.7
C6—C7—C8	121.8 (3)	C13—C18—H18	119.7
C6—C7—H7	119.1	C20—C19—S	110.37 (19)
C8—C7—H7	119.1	C20—C19—H19A	109.6
C7—C8—C9	120.8 (2)	S—C19—H19A	109.6
C7—C8—C3	118.3 (3)	C20—C19—H19B	109.6
C9—C8—C3	120.9 (2)	S—C19—H19B	109.6
C10—C9—C8	122.4 (2)	H19A—C19—H19B	108.1
C10—C9—H9	118.8	C19—C20—H20A	109.5
C8—C9—H9	118.8	C19—C20—H20B	109.5
C9—C10—C11	115.8 (2)	H20A—C20—H20B	109.5
C9—C10—H10	122.1	C19—C20—H20C	109.5
C11—C10—H10	122.1	H20A—C20—H20C	109.5
O1—C11—C2	111.62 (18)	H20B—C20—H20C	109.5
O2—S—C1—C12	132.48 (18)	C3—C2—C11—O1	−179.95 (19)
C19—S—C1—C12	−115.73 (19)	C1—C2—C11—O1	−1.9 (2)
O2—S—C1—C2	−47.7 (2)	C3—C2—C11—C10	−3.9 (3)
C19—S—C1—C2	64.1 (2)	C1—C2—C11—C10	174.1 (2)
C12—C1—C2—C11	1.5 (2)	C9—C10—C11—O1	176.2 (2)
S—C1—C2—C11	−178.31 (17)	C9—C10—C11—C2	0.6 (3)
C12—C1—C2—C3	179.1 (2)	C2—C1—C12—O1	−0.7 (2)
S—C1—C2—C3	−0.8 (4)	S—C1—C12—O1	179.19 (14)
C11—C2—C3—C4	−174.8 (2)	C2—C1—C12—C13	−178.5 (2)
C1—C2—C3—C4	7.9 (4)	S—C1—C12—C13	1.3 (4)
C11—C2—C3—C8	3.8 (3)	C11—O1—C12—C1	−0.5 (2)
C1—C2—C3—C8	−173.5 (2)	C11—O1—C12—C13	177.89 (17)
C8—C3—C4—C5	2.9 (3)	C1—C12—C13—C14	−143.3 (3)
C2—C3—C4—C5	−178.6 (2)	O1—C12—C13—C14	38.9 (3)
C3—C4—C5—C6	−1.7 (4)	C1—C12—C13—C18	40.6 (4)
C4—C5—C6—C7	0.0 (4)	O1—C12—C13—C18	−137.2 (2)
C5—C6—C7—C8	0.5 (4)	C18—C13—C14—C15	0.4 (3)
C6—C7—C8—C9	−179.5 (2)	C12—C13—C14—C15	−175.7 (2)
C6—C7—C8—C3	0.7 (4)	C13—C14—C15—C16	0.2 (4)
C4—C3—C8—C7	−2.4 (3)	C14—C15—C16—C17	−0.9 (4)
C2—C3—C8—C7	178.9 (2)	C14—C15—C16—I	177.76 (17)
C4—C3—C8—C9	177.9 (2)	C15—C16—C17—C18	0.7 (3)
C2—C3—C8—C9	−0.8 (3)	I—C16—C17—C18	−177.86 (17)
C7—C8—C9—C10	177.7 (2)	C16—C17—C18—C13	0.0 (3)
C3—C8—C9—C10	−2.6 (4)	C14—C13—C18—C17	−0.6 (3)
C8—C9—C10—C11	2.7 (3)	C12—C13—C18—C17	175.5 (2)
C12—O1—C11—C2	1.5 (2)	O2—S—C19—C20	−57.7 (2)
C12—O1—C11—C10	−174.6 (2)	C1—S—C19—C20	−170.25 (19)

Cg is the centroid of the C13–C18 4-iodophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···O2i	0.98	2.60	3.454 (4)	145
C19—H19B···Cgii	0.99	2.77	3.501 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 4-iodo­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20C⋯O2i	0.98	2.60	3.454 (4)	145
C19—H19B⋯Cgii	0.99	2.77	3.501 (3)	131

Symmetry codes: (i) ; (ii) .