7-Bromo-2-(4-methyl-phen-yl)-1-(methyl-sulfin-yl)naphtho-[2,1-b]furan.

In the title compound, C20H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.030 (2) Å] of the naphtho-furan ring system and the 4-methyl-phenyl ring is 38.49 (9)°. In the crystal, mol-ecules are linked by C-H⋯π and C-Br⋯π [3.871 (2) Å] inter-actions into stacks along the b-axis direction. These stacks are further linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C20H15BrO2S

M = 399.29

Monoclinic,

a = 6.2198 (11) Å

b = 23.234 (4) Å

c = 11.344 (2) Å

β = 94.733 (12)°

V = 1633.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.65 mm−1

T = 173 K

0.27 × 0.19 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.472, T max = 0.746

16182 measured reflections

4083 independent reflections

3135 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.04

4083 reflections

219 parameters

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −0.63 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016978/hg5324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016978/hg5324Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016978/hg5324Isup3.cml

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

C20H15BrO2S	F(000) = 808
Mr = 399.29	Dx = 1.623 Mg m−3
Monoclinic, P21/c	Melting point = 485–486 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.2198 (11) Å	Cell parameters from 3620 reflections
b = 23.234 (4) Å	θ = 2.5–27.0°
c = 11.344 (2) Å	µ = 2.65 mm−1
β = 94.733 (12)°	T = 173 K
V = 1633.7 (5) Å3	Block, colourless
Z = 4	0.27 × 0.19 × 0.11 mm

Bruker SMART APEXII CCD diffractometer	4083 independent reflections
Radiation source: rotating anode	3135 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.070
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.8°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −30→30
Tmin = 0.472, Tmax = 0.746	l = −15→15
16182 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.6314P] where P = (Fo2 + 2Fc2)/3
4083 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 1.16 e Å−3
0 restraints	Δρmin = −0.63 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
Br1	0.08040 (5)	0.625454 (16)	1.02806 (3)	0.03661 (13)
S1	0.99799 (11)	0.71743 (3)	0.64298 (6)	0.02279 (16)
O1	1.0693 (3)	0.54998 (8)	0.62255 (17)	0.0226 (4)
O2	0.9682 (3)	0.74231 (8)	0.76168 (19)	0.0299 (5)
C1	0.9742 (4)	0.64212 (12)	0.6514 (2)	0.0198 (5)
C2	0.8386 (4)	0.60547 (11)	0.7188 (2)	0.0198 (5)
C3	0.6611 (4)	0.61296 (12)	0.7902 (2)	0.0216 (6)
C4	0.5747 (4)	0.66676 (12)	0.8204 (2)	0.0235 (6)
H4	0.6369	0.7011	0.7932	0.028*
C5	0.4029 (5)	0.67024 (13)	0.8883 (3)	0.0267 (6)
H5	0.3461	0.7067	0.9075	0.032*
C6	0.3116 (4)	0.61977 (13)	0.9291 (3)	0.0259 (6)
C7	0.3880 (4)	0.56710 (13)	0.9027 (2)	0.0264 (6)
H7	0.3220	0.5335	0.9310	0.032*
C8	0.5663 (4)	0.56194 (12)	0.8330 (2)	0.0236 (6)
C9	0.6476 (4)	0.50695 (12)	0.8070 (2)	0.0253 (6)
H9	0.5821	0.4738	0.8374	0.030*
C10	0.8171 (4)	0.50023 (12)	0.7395 (2)	0.0253 (6)
H10	0.8715	0.4632	0.7222	0.030*
C11	0.9068 (4)	0.55038 (12)	0.6971 (2)	0.0213 (5)
C12	1.1077 (4)	0.60658 (12)	0.5948 (2)	0.0207 (5)
C13	1.2659 (4)	0.61466 (11)	0.5080 (2)	0.0206 (5)
C14	1.4444 (4)	0.57774 (12)	0.5083 (2)	0.0214 (5)
H14	1.4675	0.5495	0.5685	0.026*
C15	1.5871 (4)	0.58234 (12)	0.4214 (3)	0.0231 (6)
H15	1.7088	0.5575	0.4235	0.028*
C16	1.5555 (5)	0.62264 (12)	0.3308 (3)	0.0239 (6)
C17	1.3798 (4)	0.65974 (12)	0.3322 (2)	0.0252 (6)
H17	1.3581	0.6883	0.2725	0.030*
C18	1.2359 (4)	0.65572 (12)	0.4190 (2)	0.0239 (6)
H18	1.1162	0.6812	0.4176	0.029*
C19	1.7039 (5)	0.62599 (13)	0.2328 (3)	0.0309 (7)
H19A	1.8006	0.6591	0.2460	0.046*
H19B	1.6183	0.6305	0.1569	0.046*
H19C	1.7894	0.5906	0.2316	0.046*
C20	0.7540 (5)	0.73215 (13)	0.5513 (3)	0.0318 (7)
H20A	0.6305	0.7158	0.5881	0.048*
H20B	0.7635	0.7148	0.4732	0.048*
H20C	0.7350	0.7739	0.5428	0.048*

	U11	U22	U33	U12	U13	U23
Br1	0.03055 (19)	0.0514 (2)	0.02954 (18)	0.00701 (13)	0.01237 (13)	0.00111 (14)
S1	0.0252 (3)	0.0159 (3)	0.0275 (4)	−0.0011 (2)	0.0034 (3)	−0.0017 (3)
O1	0.0257 (9)	0.0171 (10)	0.0262 (10)	0.0019 (7)	0.0083 (8)	0.0005 (8)
O2	0.0372 (11)	0.0225 (11)	0.0302 (11)	0.0008 (9)	0.0029 (9)	−0.0079 (9)
C1	0.0216 (13)	0.0176 (13)	0.0203 (12)	−0.0008 (10)	0.0021 (10)	−0.0009 (10)
C2	0.0215 (13)	0.0179 (13)	0.0202 (13)	−0.0009 (10)	0.0032 (10)	−0.0013 (10)
C3	0.0237 (13)	0.0229 (14)	0.0183 (12)	0.0007 (10)	0.0032 (10)	−0.0037 (11)
C4	0.0249 (14)	0.0213 (14)	0.0245 (14)	−0.0017 (11)	0.0025 (11)	−0.0016 (11)
C5	0.0262 (14)	0.0259 (16)	0.0282 (15)	0.0042 (11)	0.0027 (11)	−0.0040 (12)
C6	0.0215 (13)	0.0361 (17)	0.0204 (13)	0.0013 (11)	0.0035 (11)	−0.0035 (12)
C7	0.0256 (14)	0.0316 (16)	0.0226 (14)	−0.0043 (12)	0.0060 (11)	0.0021 (12)
C8	0.0284 (14)	0.0237 (15)	0.0189 (13)	0.0015 (11)	0.0027 (10)	−0.0032 (11)
C9	0.0316 (15)	0.0193 (14)	0.0257 (14)	−0.0062 (11)	0.0072 (11)	0.0017 (11)
C10	0.0323 (15)	0.0174 (14)	0.0267 (14)	0.0019 (11)	0.0048 (12)	0.0010 (11)
C11	0.0215 (12)	0.0215 (14)	0.0209 (13)	0.0026 (10)	0.0022 (10)	−0.0002 (11)
C12	0.0224 (13)	0.0199 (14)	0.0197 (13)	−0.0007 (10)	0.0009 (10)	−0.0003 (10)
C13	0.0222 (13)	0.0181 (13)	0.0220 (13)	−0.0016 (10)	0.0039 (10)	−0.0022 (10)
C14	0.0242 (13)	0.0172 (13)	0.0232 (13)	0.0003 (10)	0.0034 (10)	0.0005 (11)
C15	0.0210 (13)	0.0195 (14)	0.0293 (14)	0.0005 (10)	0.0041 (11)	−0.0020 (11)
C16	0.0265 (14)	0.0202 (14)	0.0254 (14)	−0.0060 (11)	0.0050 (11)	−0.0006 (11)
C17	0.0316 (15)	0.0204 (14)	0.0238 (14)	−0.0003 (11)	0.0028 (11)	0.0038 (11)
C18	0.0264 (14)	0.0198 (14)	0.0256 (14)	0.0027 (11)	0.0036 (11)	0.0009 (11)
C19	0.0328 (16)	0.0291 (17)	0.0320 (16)	−0.0043 (12)	0.0103 (13)	0.0023 (13)
C20	0.0398 (17)	0.0244 (16)	0.0302 (16)	0.0060 (13)	−0.0032 (13)	0.0007 (13)

Br1—C6	1.900 (3)	C9—H9	0.9500
S1—O2	1.491 (2)	C10—C11	1.395 (4)
S1—C1	1.759 (3)	C10—H10	0.9500
S1—C20	1.801 (3)	C12—C13	1.460 (4)
O1—C11	1.370 (3)	C13—C18	1.390 (4)
O1—C12	1.378 (3)	C13—C14	1.403 (4)
C1—C12	1.368 (4)	C14—C15	1.384 (4)
C1—C2	1.459 (4)	C14—H14	0.9500
C2—C11	1.377 (4)	C15—C16	1.392 (4)
C2—C3	1.433 (4)	C15—H15	0.9500
C3—C4	1.414 (4)	C16—C17	1.393 (4)
C3—C8	1.427 (4)	C16—C19	1.504 (4)
C4—C5	1.370 (4)	C17—C18	1.388 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.399 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—H19A	0.9800
C6—C7	1.355 (4)	C19—H19B	0.9800
C7—C8	1.419 (4)	C19—H19C	0.9800
C7—H7	0.9500	C20—H20A	0.9800
C8—C9	1.414 (4)	C20—H20B	0.9800
C9—C10	1.362 (4)	C20—H20C	0.9800
O2—S1—C1	108.63 (13)	O1—C11—C10	122.9 (2)
O2—S1—C20	106.64 (14)	C2—C11—C10	125.3 (3)
C1—S1—C20	98.61 (14)	C1—C12—O1	110.2 (2)
C11—O1—C12	106.6 (2)	C1—C12—C13	135.0 (3)
C12—C1—C2	107.1 (2)	O1—C12—C13	114.6 (2)
C12—C1—S1	121.2 (2)	C18—C13—C14	118.7 (3)
C2—C1—S1	131.6 (2)	C18—C13—C12	121.3 (3)
C11—C2—C3	118.5 (2)	C14—C13—C12	119.8 (2)
C11—C2—C1	104.4 (2)	C15—C14—C13	120.3 (3)
C3—C2—C1	137.0 (3)	C15—C14—H14	119.9
C4—C3—C8	118.4 (2)	C13—C14—H14	119.9
C4—C3—C2	124.8 (3)	C14—C15—C16	121.2 (3)
C8—C3—C2	116.8 (2)	C14—C15—H15	119.4
C5—C4—C3	121.2 (3)	C16—C15—H15	119.4
C5—C4—H4	119.4	C15—C16—C17	118.1 (3)
C3—C4—H4	119.4	C15—C16—C19	121.5 (3)
C4—C5—C6	119.6 (3)	C17—C16—C19	120.4 (3)
C4—C5—H5	120.2	C18—C17—C16	121.3 (3)
C6—C5—H5	120.2	C18—C17—H17	119.4
C7—C6—C5	121.6 (3)	C16—C17—H17	119.4
C7—C6—Br1	119.3 (2)	C17—C18—C13	120.4 (3)
C5—C6—Br1	119.0 (2)	C17—C18—H18	119.8
C6—C7—C8	120.3 (3)	C13—C18—H18	119.8
C6—C7—H7	119.9	C16—C19—H19A	109.5
C8—C7—H7	119.9	C16—C19—H19B	109.5
C9—C8—C7	120.1 (3)	H19A—C19—H19B	109.5
C9—C8—C3	121.0 (2)	C16—C19—H19C	109.5
C7—C8—C3	118.9 (3)	H19A—C19—H19C	109.5
C10—C9—C8	121.8 (3)	H19B—C19—H19C	109.5
C10—C9—H9	119.1	S1—C20—H20A	109.5
C8—C9—H9	119.1	S1—C20—H20B	109.5
C9—C10—C11	116.6 (3)	H20A—C20—H20B	109.5
C9—C10—H10	121.7	S1—C20—H20C	109.5
C11—C10—H10	121.7	H20A—C20—H20C	109.5
O1—C11—C2	111.7 (2)	H20B—C20—H20C	109.5
O2—S1—C1—C12	−139.7 (2)	C12—O1—C11—C2	−0.1 (3)
C20—S1—C1—C12	109.4 (2)	C12—O1—C11—C10	176.8 (2)
O2—S1—C1—C2	35.1 (3)	C3—C2—C11—O1	176.7 (2)
C20—S1—C1—C2	−75.8 (3)	C1—C2—C11—O1	−0.5 (3)
C12—C1—C2—C11	0.8 (3)	C3—C2—C11—C10	−0.1 (4)
S1—C1—C2—C11	−174.6 (2)	C1—C2—C11—C10	−177.2 (3)
C12—C1—C2—C3	−175.5 (3)	C9—C10—C11—O1	−176.0 (2)
S1—C1—C2—C3	9.1 (5)	C9—C10—C11—C2	0.5 (4)
C11—C2—C3—C4	179.6 (3)	C2—C1—C12—O1	−0.9 (3)
C1—C2—C3—C4	−4.5 (5)	S1—C1—C12—O1	175.08 (18)
C11—C2—C3—C8	−0.6 (4)	C2—C1—C12—C13	174.0 (3)
C1—C2—C3—C8	175.3 (3)	S1—C1—C12—C13	−10.0 (5)
C8—C3—C4—C5	−0.5 (4)	C11—O1—C12—C1	0.6 (3)
C2—C3—C4—C5	179.3 (3)	C11—O1—C12—C13	−175.4 (2)
C3—C4—C5—C6	0.3 (4)	C1—C12—C13—C18	−35.4 (5)
C4—C5—C6—C7	−0.4 (5)	O1—C12—C13—C18	139.3 (3)
C4—C5—C6—Br1	177.7 (2)	C1—C12—C13—C14	149.3 (3)
C5—C6—C7—C8	0.6 (4)	O1—C12—C13—C14	−36.0 (3)
Br1—C6—C7—C8	−177.4 (2)	C18—C13—C14—C15	−0.1 (4)
C6—C7—C8—C9	179.1 (3)	C12—C13—C14—C15	175.4 (3)
C6—C7—C8—C3	−0.8 (4)	C13—C14—C15—C16	−1.2 (4)
C4—C3—C8—C9	−179.2 (2)	C14—C15—C16—C17	2.2 (4)
C2—C3—C8—C9	1.0 (4)	C14—C15—C16—C19	−177.0 (3)
C4—C3—C8—C7	0.8 (4)	C15—C16—C17—C18	−2.0 (4)
C2—C3—C8—C7	−179.1 (2)	C19—C16—C17—C18	177.2 (3)
C7—C8—C9—C10	179.4 (3)	C16—C17—C18—C13	0.8 (4)
C3—C8—C9—C10	−0.7 (4)	C14—C13—C18—C17	0.3 (4)
C8—C9—C10—C11	−0.1 (4)	C12—C13—C18—C17	−175.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O2i	0.98	2.52	3.476 (4)	166
C14—H14···Cg1ii	0.95	2.68	3.342 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O2i	0.98	2.52	3.476 (4)	166
C14—H14⋯Cg1ii	0.95	2.68	3.342 (4)	127

Symmetry codes: (i) ; (ii) .