1-(4-Bromo-phenyl-sulfon-yl)-2-methyl-naphtho-[2,1-b]furan.

In the title compound, C(19)H(13)BrO(3)S, the 4-bromo-phenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphtho-furan ring. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits slipped π-π inter-actions between the central naphtho-furan benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphtho-furan benzene ring and the furan ring of neighbouring mol-ecules [centroid-centroid distance = 3.655 (2), slippage = 1.136 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2012 ▶).

Experimental

Crystal data

C19H13BrO3S

M = 401.26

Triclinic,

a = 6.9579 (2) Å

b = 10.9709 (4) Å

c = 11.4207 (4) Å

α = 110.510 (2)°

β = 105.886 (2)°

γ = 91.656 (2)°

V = 777.77 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.79 mm−1

T = 173 K

0.29 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.555, T max = 0.746

14423 measured reflections

3876 independent reflections

3201 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.05

3876 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.35 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/S160053681202939X/ff2074sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202939X/ff2074Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202939X/ff2074Isup3.cml

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

C19H13BrO3S	Z = 2
Mr = 401.26	F(000) = 404
Triclinic, P1	Dx = 1.713 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9579 (2) Å	Cell parameters from 6011 reflections
b = 10.9709 (4) Å	θ = 2.2–27.9°
c = 11.4207 (4) Å	µ = 2.79 mm−1
α = 110.510 (2)°	T = 173 K
β = 105.886 (2)°	Block, colourless
γ = 91.656 (2)°	0.29 × 0.13 × 0.10 mm
V = 777.77 (5) Å3

Bruker SMART APEXII CCD diffractometer	3876 independent reflections
Radiation source: rotating anode	3201 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.036
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.555, Tmax = 0.746	l = −15→15
14423 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F2) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2709P] where P = (Fo2 + 2Fc2)/3
3876 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.35 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	1.25056 (3)	0.78521 (2)	1.20765 (2)	0.04071 (10)
S1	0.33058 (8)	0.71206 (4)	0.86111 (5)	0.02364 (12)
O1	0.2860 (2)	0.71224 (15)	0.51468 (15)	0.0292 (3)
O2	0.2305 (2)	0.60540 (13)	0.87692 (14)	0.0279 (3)
O3	0.2685 (2)	0.83982 (14)	0.90608 (16)	0.0316 (3)
C1	0.3103 (3)	0.67109 (19)	0.6958 (2)	0.0239 (4)
C2	0.2740 (3)	0.54502 (19)	0.5872 (2)	0.0230 (4)
C3	0.2529 (3)	0.40719 (19)	0.5655 (2)	0.0237 (4)
C4	0.2678 (3)	0.3548 (2)	0.6634 (2)	0.0290 (4)
H4	0.2924	0.4128	0.7518	0.035*
C5	0.2476 (4)	0.2215 (2)	0.6336 (2)	0.0337 (5)
H5	0.2587	0.1886	0.7015	0.040*
C6	0.2108 (4)	0.1340 (2)	0.5044 (2)	0.0366 (5)
H6	0.1970	0.0419	0.4844	0.044*
C7	0.1949 (3)	0.1816 (2)	0.4076 (2)	0.0342 (5)
H7	0.1694	0.1215	0.3199	0.041*
C8	0.2153 (3)	0.3179 (2)	0.4338 (2)	0.0270 (4)
C9	0.1972 (3)	0.3626 (2)	0.3291 (2)	0.0321 (5)
H9	0.1690	0.3001	0.2422	0.038*
C10	0.2193 (3)	0.4924 (2)	0.3507 (2)	0.0310 (5)
H10	0.2082	0.5229	0.2812	0.037*
C11	0.2592 (3)	0.5787 (2)	0.4802 (2)	0.0270 (4)
C12	0.3190 (3)	0.7668 (2)	0.6459 (2)	0.0272 (4)
C13	0.3533 (4)	0.9123 (2)	0.6993 (2)	0.0350 (5)
H13A	0.4214	0.9430	0.6481	0.053*
H13B	0.4376	0.9444	0.7911	0.053*
H13C	0.2234	0.9458	0.6940	0.053*
C14	0.5890 (3)	0.72911 (18)	0.94600 (19)	0.0234 (4)
C15	0.6697 (3)	0.62392 (19)	0.9740 (2)	0.0274 (4)
H15	0.5888	0.5408	0.9405	0.033*
C16	0.8677 (3)	0.6410 (2)	1.0507 (2)	0.0284 (4)
H16	0.9231	0.5704	1.0717	0.034*
C17	0.9844 (3)	0.7619 (2)	1.0966 (2)	0.0280 (4)
C18	0.9081 (3)	0.8657 (2)	1.0663 (2)	0.0310 (5)
H18	0.9915	0.9474	1.0965	0.037*
C19	0.7094 (3)	0.84936 (19)	0.9916 (2)	0.0280 (4)
H19	0.6548	0.9205	0.9713	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.03136 (14)	0.04733 (16)	0.03750 (15)	−0.00121 (10)	−0.00038 (10)	0.01757 (12)
S1	0.0257 (2)	0.0192 (2)	0.0267 (3)	0.00392 (18)	0.0099 (2)	0.00780 (19)
O1	0.0271 (8)	0.0331 (8)	0.0317 (8)	0.0034 (6)	0.0083 (7)	0.0178 (7)
O2	0.0308 (8)	0.0245 (7)	0.0309 (8)	0.0017 (6)	0.0122 (7)	0.0113 (6)
O3	0.0346 (8)	0.0241 (7)	0.0386 (9)	0.0103 (6)	0.0165 (7)	0.0102 (6)
C1	0.0223 (10)	0.0236 (9)	0.0261 (10)	0.0041 (8)	0.0067 (8)	0.0100 (8)
C2	0.0161 (9)	0.0265 (9)	0.0263 (10)	0.0037 (7)	0.0062 (8)	0.0101 (8)
C3	0.0161 (9)	0.0245 (9)	0.0269 (10)	0.0035 (7)	0.0041 (8)	0.0072 (8)
C4	0.0297 (11)	0.0254 (10)	0.0304 (11)	0.0052 (8)	0.0068 (9)	0.0100 (9)
C5	0.0369 (12)	0.0254 (10)	0.0367 (13)	0.0050 (9)	0.0075 (10)	0.0119 (10)
C6	0.0354 (12)	0.0223 (10)	0.0458 (14)	0.0048 (9)	0.0109 (11)	0.0064 (10)
C7	0.0295 (11)	0.0288 (11)	0.0328 (12)	0.0015 (9)	0.0077 (10)	−0.0007 (9)
C8	0.0176 (9)	0.0305 (10)	0.0292 (11)	0.0035 (8)	0.0067 (8)	0.0070 (9)
C9	0.0243 (10)	0.0408 (12)	0.0245 (11)	0.0016 (9)	0.0066 (9)	0.0050 (9)
C10	0.0241 (10)	0.0431 (12)	0.0275 (11)	0.0044 (9)	0.0077 (9)	0.0153 (10)
C11	0.0190 (9)	0.0314 (10)	0.0325 (11)	0.0056 (8)	0.0079 (8)	0.0139 (9)
C12	0.0233 (10)	0.0285 (10)	0.0319 (11)	0.0046 (8)	0.0088 (9)	0.0134 (9)
C13	0.0399 (13)	0.0276 (11)	0.0429 (14)	0.0050 (9)	0.0135 (11)	0.0186 (10)
C14	0.0263 (10)	0.0204 (9)	0.0231 (10)	0.0033 (7)	0.0085 (8)	0.0068 (8)
C15	0.0298 (11)	0.0200 (9)	0.0318 (11)	0.0026 (8)	0.0103 (9)	0.0084 (8)
C16	0.0311 (11)	0.0257 (10)	0.0304 (11)	0.0060 (8)	0.0101 (9)	0.0120 (9)
C17	0.0263 (10)	0.0319 (11)	0.0250 (11)	0.0020 (8)	0.0076 (9)	0.0100 (9)
C18	0.0335 (11)	0.0259 (10)	0.0287 (11)	−0.0037 (9)	0.0056 (9)	0.0079 (9)
C19	0.0344 (11)	0.0207 (9)	0.0278 (11)	0.0032 (8)	0.0080 (9)	0.0091 (8)

Br1—C17	1.888 (2)	C7—H7	0.9500
S1—O2	1.4340 (14)	C8—C9	1.421 (3)
S1—O3	1.4376 (15)	C9—C10	1.354 (3)
S1—C1	1.744 (2)	C9—H9	0.9500
S1—C14	1.763 (2)	C10—C11	1.393 (3)
O1—C12	1.353 (3)	C10—H10	0.9500
O1—C11	1.370 (2)	C12—C13	1.482 (3)
C1—C12	1.366 (3)	C13—H13A	0.9800
C1—C2	1.457 (3)	C13—H13B	0.9800
C2—C11	1.375 (3)	C13—H13C	0.9800
C2—C3	1.440 (3)	C14—C19	1.389 (3)
C3—C4	1.407 (3)	C14—C15	1.396 (3)
C3—C8	1.424 (3)	C15—C16	1.382 (3)
C4—C5	1.374 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.383 (3)
C5—C6	1.396 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.381 (3)
C6—C7	1.360 (3)	C18—C19	1.380 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.413 (3)	C19—H19	0.9500
O2—S1—O3	118.77 (9)	C9—C10—C11	116.5 (2)
O2—S1—C1	109.36 (9)	C9—C10—H10	121.8
O3—S1—C1	107.02 (9)	C11—C10—H10	121.8
O2—S1—C14	107.25 (9)	O1—C11—C2	111.59 (18)
O3—S1—C14	106.85 (9)	O1—C11—C10	121.95 (19)
C1—S1—C14	107.03 (9)	C2—C11—C10	126.4 (2)
C12—O1—C11	107.05 (16)	O1—C12—C1	110.30 (18)
C12—C1—C2	107.19 (18)	O1—C12—C13	113.74 (18)
C12—C1—S1	120.68 (16)	C1—C12—C13	136.0 (2)
C2—C1—S1	132.06 (15)	C12—C13—H13A	109.5
C11—C2—C3	117.54 (19)	C12—C13—H13B	109.5
C11—C2—C1	103.83 (17)	H13A—C13—H13B	109.5
C3—C2—C1	138.62 (19)	C12—C13—H13C	109.5
C4—C3—C8	118.08 (19)	H13A—C13—H13C	109.5
C4—C3—C2	125.39 (19)	H13B—C13—H13C	109.5
C8—C3—C2	116.52 (19)	C19—C14—C15	120.02 (19)
C5—C4—C3	121.3 (2)	C19—C14—S1	119.99 (16)
C5—C4—H4	119.4	C15—C14—S1	119.88 (15)
C3—C4—H4	119.4	C16—C15—C14	119.82 (18)
C4—C5—C6	120.6 (2)	C16—C15—H15	120.1
C4—C5—H5	119.7	C14—C15—H15	120.1
C6—C5—H5	119.7	C15—C16—C17	119.3 (2)
C7—C6—C5	119.4 (2)	C15—C16—H16	120.4
C7—C6—H6	120.3	C17—C16—H16	120.4
C5—C6—H6	120.3	C18—C17—C16	121.5 (2)
C6—C7—C8	121.9 (2)	C18—C17—Br1	119.98 (16)
C6—C7—H7	119.1	C16—C17—Br1	118.51 (17)
C8—C7—H7	119.1	C19—C18—C17	119.25 (19)
C7—C8—C9	119.7 (2)	C19—C18—H18	120.4
C7—C8—C3	118.7 (2)	C17—C18—H18	120.4
C9—C8—C3	121.7 (2)	C18—C19—C14	120.12 (19)
C10—C9—C8	121.3 (2)	C18—C19—H19	119.9
C10—C9—H9	119.3	C14—C19—H19	119.9
C8—C9—H9	119.3
O2—S1—C1—C12	154.18 (16)	C12—O1—C11—C10	179.18 (19)
O3—S1—C1—C12	24.32 (19)	C3—C2—C11—O1	−178.77 (16)
C14—S1—C1—C12	−89.95 (18)	C1—C2—C11—O1	0.9 (2)
O2—S1—C1—C2	−22.4 (2)	C3—C2—C11—C10	2.2 (3)
O3—S1—C1—C2	−152.26 (19)	C1—C2—C11—C10	−178.2 (2)
C14—S1—C1—C2	93.5 (2)	C9—C10—C11—O1	179.53 (18)
C12—C1—C2—C11	−1.5 (2)	C9—C10—C11—C2	−1.5 (3)
S1—C1—C2—C11	175.45 (16)	C11—O1—C12—C1	−1.1 (2)
C12—C1—C2—C3	178.0 (2)	C11—O1—C12—C13	179.40 (17)
S1—C1—C2—C3	−5.0 (4)	C2—C1—C12—O1	1.6 (2)
C11—C2—C3—C4	178.58 (19)	S1—C1—C12—O1	−175.75 (14)
C1—C2—C3—C4	−0.9 (4)	C2—C1—C12—C13	−179.0 (2)
C11—C2—C3—C8	−0.9 (3)	S1—C1—C12—C13	3.7 (4)
C1—C2—C3—C8	179.6 (2)	O2—S1—C14—C19	−155.16 (16)
C8—C3—C4—C5	0.2 (3)	O3—S1—C14—C19	−26.80 (19)
C2—C3—C4—C5	−179.3 (2)	C1—S1—C14—C19	87.57 (18)
C3—C4—C5—C6	−0.2 (4)	O2—S1—C14—C15	21.08 (19)
C4—C5—C6—C7	0.0 (4)	O3—S1—C14—C15	149.44 (16)
C5—C6—C7—C8	0.2 (3)	C1—S1—C14—C15	−96.18 (17)
C6—C7—C8—C9	−179.9 (2)	C19—C14—C15—C16	2.1 (3)
C6—C7—C8—C3	−0.2 (3)	S1—C14—C15—C16	−174.17 (15)
C4—C3—C8—C7	0.0 (3)	C14—C15—C16—C17	−1.2 (3)
C2—C3—C8—C7	179.52 (18)	C15—C16—C17—C18	−0.7 (3)
C4—C3—C8—C9	179.72 (19)	C15—C16—C17—Br1	177.18 (15)
C2—C3—C8—C9	−0.7 (3)	C16—C17—C18—C19	1.8 (3)
C7—C8—C9—C10	−178.8 (2)	Br1—C17—C18—C19	−176.05 (16)
C3—C8—C9—C10	1.4 (3)	C17—C18—C19—C14	−1.0 (3)
C8—C9—C10—C11	−0.4 (3)	C15—C14—C19—C18	−1.0 (3)
C12—O1—C11—C2	0.1 (2)	S1—C14—C19—C18	175.27 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2i	0.95	2.49	3.197 (2)	131
C19—H19···O3ii	0.95	2.47	3.177 (2)	132
C9—H9···Cg1iii	0.95	2.96	3.782 (2)	120

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 4-bromo­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2i	0.95	2.49	3.197 (2)	131
C19—H19⋯O3ii	0.95	2.47	3.177 (2)	132
C9—H9⋯Cg1iii	0.95	2.96	3.782 (2)	120

Symmetry codes: (i) ; (ii) ; (iii) .