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

The title compound, C(19)H(13)BrO(3)S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenyl-sulfan-yl)naph-tho[2,1-b]furan with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 80.4 (2)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π-π stacking inter-actions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring mol-ecules; the centroid-centroid distances within the stack are 3.889 (3) and 3.981 (3) Å. In addition, the stacked mol-ecules exhibit C-H⋯π, inter- and intra-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 7-bromo­naphtho[2,1-b]furan compounds, see: Choi et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C19H13BrO3S

M = 401.26

Triclinic,

a = 7.8583 (7) Å

b = 8.0025 (7) Å

c = 13.278 (1) Å

α = 107.429 (1)°

β = 93.678 (1)°

γ = 90.417 (2)°

V = 794.72 (12) Å3

Z = 2

Mo Kα radiation

μ = 2.73 mm−1

T = 173 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.381, T max = 0.571

6371 measured reflections

3084 independent reflections

2874 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.078

S = 1.17

3084 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.35 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/S160053680801177X/jh2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801177X/jh2063Isup2.hkl

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

C19H13BrO3S	Z = 2
Mr = 401.26	F000 = 404
Triclinic, P1	Dx = 1.677 Mg m−3
Hall symbol: -p 1	Melting point = 483–484 K
a = 7.8583 (7) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.0025 (7) Å	Cell parameters from 4679 reflections
c = 13.278 (1) Å	θ = 2.6–28.2º
α = 107.429 (1)º	µ = 2.73 mm−1
β = 93.678 (1)º	T = 173 (2) K
γ = 90.417 (2)º	Block, colorless
V = 794.72 (12) Å3	0.40 × 0.30 × 0.20 mm

Bruker SMART CCD diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 1.6º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	k = −9→9
Tmin = 0.381, Tmax = 0.571	l = −16→16
6371 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.2317P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max = 0.001
3084 reflections	Δρmax = 0.44 e Å−3
218 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.56455 (3)	0.99911 (3)	0.696889 (17)	0.03340 (10)
S	0.82852 (6)	0.36218 (7)	0.16782 (4)	0.02320 (13)
O1	0.91789 (19)	0.0602 (2)	0.34760 (12)	0.0280 (3)
O2	0.9034 (2)	0.5362 (2)	0.20422 (12)	0.0303 (3)
O3	0.8886 (2)	0.2407 (2)	0.07411 (12)	0.0330 (4)
C1	0.8504 (3)	0.2648 (3)	0.26930 (16)	0.0228 (4)
C2	0.8191 (2)	0.3362 (3)	0.38127 (16)	0.0216 (4)
C3	0.7591 (2)	0.4950 (3)	0.45075 (16)	0.0212 (4)
C4	0.7119 (3)	0.6446 (3)	0.42140 (17)	0.0248 (4)
H4	0.7201	0.6435	0.3501	0.030*
C5	0.6545 (3)	0.7918 (3)	0.49309 (17)	0.0265 (4)
H5	0.6230	0.8911	0.4717	0.032*
C6	0.6432 (3)	0.7931 (3)	0.59824 (17)	0.0245 (4)
C7	0.6885 (3)	0.6539 (3)	0.63190 (17)	0.0256 (4)
H7	0.6804	0.6593	0.7039	0.031*
C8	0.7476 (3)	0.5013 (3)	0.55938 (16)	0.0229 (4)
C9	0.7963 (3)	0.3570 (3)	0.59591 (17)	0.0265 (4)
H9	0.7877	0.3654	0.6683	0.032*
C10	0.8549 (3)	0.2078 (3)	0.52932 (17)	0.0269 (5)
H10	0.8883	0.1115	0.5533	0.032*
C11	0.8634 (3)	0.2034 (3)	0.42350 (17)	0.0241 (4)
C12	0.9097 (3)	0.0997 (3)	0.25436 (18)	0.0265 (4)
C13	0.6075 (3)	0.3813 (3)	0.14109 (15)	0.0238 (4)
C14	0.5417 (3)	0.5444 (3)	0.14748 (17)	0.0294 (5)
H14	0.6117	0.6475	0.1741	0.035*
C15	0.3714 (3)	0.5544 (4)	0.11432 (19)	0.0372 (6)
H15	0.3246	0.6649	0.1178	0.045*
C16	0.2704 (3)	0.4035 (4)	0.07638 (19)	0.0404 (6)
H16	0.1546	0.4108	0.0531	0.049*
C17	0.3368 (3)	0.2418 (4)	0.0720 (2)	0.0395 (6)
H17	0.2657	0.1392	0.0473	0.047*
C18	0.5066 (3)	0.2292 (3)	0.10354 (17)	0.0310 (5)
H18	0.5533	0.1183	0.0995	0.037*
C19	0.9685 (3)	−0.0435 (3)	0.1644 (2)	0.0379 (6)
H19A	0.9215	−0.0285	0.0975	0.057*
H19B	0.9292	−0.1568	0.1697	0.057*
H19C	1.0933	−0.0395	0.1665	0.057*

	U11	U22	U33	U12	U13	U23
Br	0.04740 (16)	0.02425 (14)	0.02669 (14)	0.00861 (10)	0.00501 (10)	0.00413 (9)
S	0.0219 (2)	0.0270 (3)	0.0203 (2)	0.00089 (19)	0.00223 (19)	0.0063 (2)
O1	0.0319 (8)	0.0226 (8)	0.0282 (8)	0.0070 (6)	−0.0002 (6)	0.0061 (6)
O2	0.0302 (8)	0.0308 (8)	0.0310 (8)	−0.0054 (6)	0.0006 (6)	0.0116 (7)
O3	0.0325 (8)	0.0402 (10)	0.0247 (8)	0.0068 (7)	0.0088 (6)	0.0058 (7)
C1	0.0225 (10)	0.0231 (10)	0.0213 (10)	0.0004 (8)	−0.0009 (8)	0.0052 (8)
C2	0.0205 (9)	0.0222 (10)	0.0218 (10)	−0.0009 (8)	−0.0013 (8)	0.0065 (8)
C3	0.0191 (9)	0.0224 (10)	0.0218 (10)	−0.0016 (7)	−0.0017 (7)	0.0067 (8)
C4	0.0300 (11)	0.0240 (10)	0.0215 (10)	0.0013 (8)	0.0002 (8)	0.0086 (8)
C5	0.0331 (11)	0.0215 (10)	0.0254 (11)	0.0017 (8)	−0.0008 (9)	0.0083 (8)
C6	0.0278 (10)	0.0207 (10)	0.0227 (10)	0.0015 (8)	0.0013 (8)	0.0031 (8)
C7	0.0297 (11)	0.0265 (11)	0.0208 (10)	−0.0003 (9)	0.0024 (8)	0.0070 (8)
C8	0.0231 (10)	0.0233 (10)	0.0225 (10)	−0.0010 (8)	−0.0007 (8)	0.0075 (8)
C9	0.0291 (11)	0.0290 (11)	0.0239 (10)	0.0002 (9)	0.0005 (8)	0.0119 (9)
C10	0.0285 (11)	0.0255 (11)	0.0298 (11)	0.0030 (8)	−0.0018 (9)	0.0140 (9)
C11	0.0231 (10)	0.0202 (10)	0.0269 (11)	0.0016 (8)	−0.0017 (8)	0.0047 (8)
C12	0.0239 (10)	0.0276 (11)	0.0262 (10)	0.0025 (8)	−0.0014 (8)	0.0059 (9)
C13	0.0236 (10)	0.0322 (12)	0.0162 (9)	0.0012 (8)	0.0026 (8)	0.0080 (8)
C14	0.0333 (11)	0.0326 (12)	0.0209 (10)	0.0051 (9)	0.0016 (9)	0.0060 (9)
C15	0.0355 (12)	0.0495 (15)	0.0257 (11)	0.0166 (11)	0.0050 (9)	0.0091 (11)
C16	0.0230 (11)	0.0736 (19)	0.0263 (12)	0.0053 (11)	0.0022 (9)	0.0172 (12)
C17	0.0310 (12)	0.0577 (17)	0.0314 (12)	−0.0138 (11)	−0.0041 (10)	0.0174 (12)
C18	0.0332 (12)	0.0355 (13)	0.0261 (11)	−0.0044 (10)	−0.0010 (9)	0.0128 (10)
C19	0.0454 (14)	0.0306 (13)	0.0327 (13)	0.0122 (10)	0.0012 (11)	0.0022 (10)

Br—C6	1.908 (2)	C8—C9	1.425 (3)
S—O2	1.4378 (16)	C9—C10	1.359 (3)
S—O3	1.4400 (16)	C9—H9	0.9500
S—C1	1.748 (2)	C10—C11	1.401 (3)
S—C13	1.767 (2)	C10—H10	0.9500
O1—C12	1.364 (3)	C12—C19	1.487 (3)
O1—C11	1.372 (3)	C13—C14	1.388 (3)
C1—C12	1.366 (3)	C13—C18	1.390 (3)
C1—C2	1.462 (3)	C14—C15	1.392 (3)
C2—C11	1.379 (3)	C14—H14	0.9500
C2—C3	1.432 (3)	C15—C16	1.383 (4)
C3—C4	1.410 (3)	C15—H15	0.9500
C3—C8	1.437 (3)	C16—C17	1.385 (4)
C4—C5	1.375 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.386 (3)
C5—C6	1.402 (3)	C17—H17	0.9500
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.360 (3)	C19—H19A	0.9800
C7—C8	1.413 (3)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800
O2—S—O3	118.45 (10)	C9—C10—C11	116.5 (2)
O2—S—C1	109.45 (10)	C9—C10—H10	121.8
O3—S—C1	107.55 (10)	C11—C10—H10	121.8
O2—S—C13	107.64 (10)	O1—C11—C2	111.29 (18)
O3—S—C13	106.29 (10)	O1—C11—C10	122.57 (19)
C1—S—C13	106.88 (10)	C2—C11—C10	126.1 (2)
C12—O1—C11	107.28 (17)	O1—C12—C1	110.04 (19)
C12—C1—C2	107.30 (19)	O1—C12—C19	113.40 (19)
C12—C1—S	122.87 (17)	C1—C12—C19	136.5 (2)
C2—C1—S	129.79 (16)	C14—C13—C18	121.4 (2)
C11—C2—C3	118.02 (18)	C14—C13—S	119.76 (17)
C11—C2—C1	104.08 (18)	C18—C13—S	118.51 (17)
C3—C2—C1	137.90 (19)	C13—C14—C15	119.0 (2)
C4—C3—C2	125.47 (19)	C13—C14—H14	120.5
C4—C3—C8	117.87 (19)	C15—C14—H14	120.5
C2—C3—C8	116.67 (19)	C16—C15—C14	120.0 (2)
C5—C4—C3	121.8 (2)	C16—C15—H15	120.0
C5—C4—H4	119.1	C14—C15—H15	120.0
C3—C4—H4	119.1	C15—C16—C17	120.5 (2)
C4—C5—C6	118.9 (2)	C15—C16—H16	119.7
C4—C5—H5	120.5	C17—C16—H16	119.7
C6—C5—H5	120.5	C16—C17—C18	120.3 (2)
C7—C6—C5	122.2 (2)	C16—C17—H17	119.9
C7—C6—Br	119.45 (16)	C18—C17—H17	119.9
C5—C6—Br	118.36 (16)	C17—C18—C13	118.9 (2)
C6—C7—C8	119.7 (2)	C17—C18—H18	120.6
C6—C7—H7	120.1	C13—C18—H18	120.6
C8—C7—H7	120.1	C12—C19—H19A	109.5
C7—C8—C9	119.17 (19)	C12—C19—H19B	109.5
C7—C8—C3	119.49 (19)	H19A—C19—H19B	109.5
C9—C8—C3	121.34 (19)	C12—C19—H19C	109.5
C10—C9—C8	121.4 (2)	H19A—C19—H19C	109.5
C10—C9—H9	119.3	H19B—C19—H19C	109.5
C8—C9—H9	119.3
O2—S—C1—C12	−131.89 (18)	C8—C9—C10—C11	−0.4 (3)
O3—S—C1—C12	−2.0 (2)	C12—O1—C11—C2	0.2 (2)
C13—S—C1—C12	111.81 (19)	C12—O1—C11—C10	179.8 (2)
O2—S—C1—C2	45.6 (2)	C3—C2—C11—O1	179.89 (17)
O3—S—C1—C2	175.49 (18)	C1—C2—C11—O1	0.0 (2)
C13—S—C1—C2	−70.7 (2)	C3—C2—C11—C10	0.3 (3)
C12—C1—C2—C11	−0.1 (2)	C1—C2—C11—C10	−179.6 (2)
S—C1—C2—C11	−177.90 (16)	C9—C10—C11—O1	−179.10 (19)
C12—C1—C2—C3	180.0 (2)	C9—C10—C11—C2	0.4 (3)
S—C1—C2—C3	2.2 (4)	C11—O1—C12—C1	−0.3 (2)
C11—C2—C3—C4	178.60 (19)	C11—O1—C12—C19	178.94 (19)
C1—C2—C3—C4	−1.5 (4)	C2—C1—C12—O1	0.2 (2)
C11—C2—C3—C8	−1.0 (3)	S—C1—C12—O1	178.21 (14)
C1—C2—C3—C8	178.9 (2)	C2—C1—C12—C19	−178.7 (3)
C2—C3—C4—C5	179.6 (2)	S—C1—C12—C19	−0.7 (4)
C8—C3—C4—C5	−0.8 (3)	O2—S—C13—C14	5.9 (2)
C3—C4—C5—C6	0.2 (3)	O3—S—C13—C14	−121.94 (17)
C4—C5—C6—C7	0.5 (3)	C1—S—C13—C14	123.41 (17)
C4—C5—C6—Br	179.61 (16)	O2—S—C13—C18	179.40 (16)
C5—C6—C7—C8	−0.6 (3)	O3—S—C13—C18	51.54 (19)
Br—C6—C7—C8	−179.70 (15)	C1—S—C13—C18	−63.10 (19)
C6—C7—C8—C9	179.35 (19)	C18—C13—C14—C15	−0.7 (3)
C6—C7—C8—C3	0.0 (3)	S—C13—C14—C15	172.57 (17)
C4—C3—C8—C7	0.7 (3)	C13—C14—C15—C16	0.4 (3)
C2—C3—C8—C7	−179.67 (18)	C14—C15—C16—C17	0.7 (4)
C4—C3—C8—C9	−178.63 (19)	C15—C16—C17—C18	−1.4 (4)
C2—C3—C8—C9	1.0 (3)	C16—C17—C18—C13	1.1 (4)
C7—C8—C9—C10	−179.6 (2)	C14—C13—C18—C17	0.0 (3)
C3—C8—C9—C10	−0.3 (3)	S—C13—C18—C17	−173.39 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1i	0.95	2.85	3.764 (3)	161
C4—H4···O2	0.95	2.44	3.226 (3)	140
C16—H16···O3ii	0.95	2.56	3.257 (3)	130
C19—H19A···O3	0.98	2.28	2.926 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1i	0.95	2.85	3.764 (3)	161
C4—H4⋯O2	0.95	2.44	3.226 (3)	140
C16—H16⋯O3ii	0.95	2.56	3.257 (3)	130
C19—H19A⋯O3	0.98	2.28	2.926 (3)	122

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