3-(4-Chloro-phenyl-sulfon-yl)-2-methyl-naphtho[1,2-b]furan.

The title compound, C(19)H(13)ClO(3)S, was prepared by the oxidation of 3-(4-chloro-phenyl-sulfan-yl)-2-methyl-naphtho[1,2-b]furan with 3-chloro-peroxy-benzoic acid. The 4-chloro-phenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.635 (3) Å], and by C-H⋯π inter-actions between a methyl H atom and the furan ring of an adjacent mol-ecule. In addition, the crystal structure exhibits inter-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 2-methyl­naphtho[1,2-b]furan derivatives, see: Choi et al. (2006 ▶, 2008 ▶).

Experimental

Crystal data

C19H13ClO3S

M = 356.80

Orthorhombic,

a = 8.1155 (3) Å

b = 18.6014 (7) Å

c = 10.8319 (4) Å

V = 1635.18 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 173 (2) K

0.60 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.842, T max = 0.857

9543 measured reflections

2611 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.066

S = 1.06

2611 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 728 Freidel pairs

Flack parameter: −0.01 (5)

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/S1600536808009215/at2553sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009215/at2553Isup2.hkl

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

C19H13ClO3S	Dx = 1.449 Mg m−3
Mr = 356.80	Melting point = 427–428 K
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7325 reflections
a = 8.1155 (3) Å	θ = 2.2–28.2º
b = 18.6014 (7) Å	µ = 0.38 mm−1
c = 10.8319 (4) Å	T = 173 (2) K
V = 1635.18 (11) Å3	Block, colourless
Z = 4	0.60 × 0.40 × 0.40 mm
F000 = 736

Bruker SMART CCD diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.7º
φ and ω scans	h = −10→10
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −23→23
Tmin = 0.842, Tmax = 0.857	l = −6→13
9543 measured reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.2762P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.26 e Å−3
2611 reflections	Δρmin = −0.20 e Å−3
218 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 728 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (5)
Secondary atom site location: difference Fourier map

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
Cl	−0.09521 (6)	−0.07862 (3)	0.70659 (5)	0.04239 (14)
S	0.49747 (5)	0.08522 (2)	0.47158 (5)	0.02560 (10)
O1	0.55982 (14)	0.27683 (6)	0.61467 (14)	0.0294 (3)
O2	0.64177 (14)	0.04043 (6)	0.48194 (16)	0.0336 (3)
O3	0.44235 (16)	0.10742 (7)	0.35113 (14)	0.0344 (3)
C1	0.5352 (2)	0.16153 (8)	0.55974 (18)	0.0247 (3)
C2	0.62790 (19)	0.16344 (9)	0.67380 (18)	0.0256 (4)
C3	0.7034 (2)	0.11205 (9)	0.75222 (19)	0.0292 (4)
H3	0.6974	0.0621	0.7341	0.035*
C4	0.7847 (2)	0.13619 (9)	0.85426 (19)	0.0305 (4)
H4	0.8359	0.1022	0.9073	0.037*
C5	0.7955 (2)	0.21145 (10)	0.88442 (19)	0.0302 (4)
C6	0.8787 (2)	0.23535 (11)	0.9915 (2)	0.0386 (5)
H6	0.9282	0.2014	1.0456	0.046*
C7	0.8882 (3)	0.30743 (12)	1.0175 (2)	0.0449 (5)
H7	0.9442	0.3229	1.0898	0.054*
C8	0.8164 (3)	0.35875 (11)	0.9391 (2)	0.0421 (5)
H8	0.8249	0.4084	0.9585	0.051*
C9	0.7342 (2)	0.33765 (9)	0.8346 (2)	0.0347 (4)
H9	0.6858	0.3725	0.7817	0.042*
C10	0.7220 (2)	0.26328 (9)	0.80628 (19)	0.0280 (4)
C11	0.63904 (19)	0.23541 (8)	0.7025 (2)	0.0261 (3)
C12	0.4971 (2)	0.23071 (9)	0.5286 (2)	0.0280 (4)
C13	0.3328 (2)	0.03991 (8)	0.54446 (17)	0.0244 (3)
C14	0.3626 (2)	−0.01619 (9)	0.6257 (2)	0.0309 (4)
H14	0.4725	−0.0296	0.6455	0.037*
C15	0.2315 (2)	−0.05239 (10)	0.6775 (2)	0.0347 (4)
H15	0.2495	−0.0909	0.7335	0.042*
C16	0.0717 (2)	−0.03142 (10)	0.64619 (18)	0.0287 (4)
C17	0.0409 (2)	0.02495 (10)	0.5670 (2)	0.0297 (4)
H17	−0.0691	0.0385	0.5479	0.036*
C18	0.1726 (2)	0.06139 (9)	0.51591 (18)	0.0268 (4)
H18	0.1543	0.1008	0.4618	0.032*
C19	0.4122 (2)	0.26521 (10)	0.4225 (2)	0.0354 (4)
H19A	0.3484	0.3065	0.4519	0.053*
H19B	0.3379	0.2304	0.3835	0.053*
H19C	0.4941	0.2814	0.3622	0.053*

	U11	U22	U33	U12	U13	U23
Cl	0.0366 (2)	0.0513 (3)	0.0393 (3)	−0.01236 (19)	0.0047 (2)	0.0104 (2)
S	0.02092 (18)	0.02869 (18)	0.0272 (2)	−0.00070 (14)	0.00189 (17)	−0.0036 (2)
O1	0.0279 (6)	0.0247 (5)	0.0357 (7)	−0.0001 (5)	0.0022 (6)	0.0033 (6)
O2	0.0221 (5)	0.0340 (6)	0.0447 (9)	0.0030 (5)	0.0019 (6)	−0.0096 (7)
O3	0.0317 (6)	0.0431 (7)	0.0285 (7)	−0.0038 (6)	0.0033 (6)	0.0006 (6)
C1	0.0212 (7)	0.0245 (7)	0.0284 (9)	−0.0012 (6)	0.0030 (7)	−0.0019 (7)
C2	0.0209 (7)	0.0273 (7)	0.0286 (10)	−0.0015 (6)	0.0043 (7)	−0.0023 (7)
C3	0.0298 (8)	0.0244 (8)	0.0335 (10)	0.0010 (6)	0.0024 (8)	0.0002 (7)
C4	0.0305 (8)	0.0300 (8)	0.0310 (10)	0.0027 (7)	0.0008 (8)	0.0011 (8)
C5	0.0246 (8)	0.0346 (9)	0.0314 (10)	−0.0023 (6)	0.0044 (8)	−0.0044 (8)
C6	0.0346 (9)	0.0471 (11)	0.0339 (12)	−0.0016 (8)	0.0003 (9)	−0.0045 (9)
C7	0.0432 (11)	0.0516 (11)	0.0401 (13)	−0.0097 (9)	−0.0022 (10)	−0.0154 (11)
C8	0.0436 (11)	0.0349 (9)	0.0478 (14)	−0.0115 (8)	0.0076 (10)	−0.0133 (9)
C9	0.0347 (9)	0.0287 (8)	0.0406 (11)	−0.0054 (7)	0.0085 (9)	−0.0035 (8)
C10	0.0243 (7)	0.0272 (8)	0.0326 (10)	−0.0025 (6)	0.0054 (8)	−0.0048 (7)
C11	0.0219 (7)	0.0250 (7)	0.0315 (9)	−0.0004 (6)	0.0052 (8)	0.0016 (8)
C12	0.0208 (7)	0.0301 (8)	0.0330 (10)	−0.0023 (6)	0.0029 (7)	0.0009 (8)
C13	0.0227 (7)	0.0257 (7)	0.0247 (9)	−0.0012 (6)	0.0003 (7)	−0.0036 (7)
C14	0.0272 (8)	0.0316 (8)	0.0338 (10)	0.0005 (7)	−0.0081 (8)	0.0026 (8)
C15	0.0373 (9)	0.0339 (9)	0.0330 (11)	−0.0025 (7)	−0.0074 (8)	0.0083 (8)
C16	0.0281 (8)	0.0336 (8)	0.0244 (10)	−0.0071 (7)	0.0010 (8)	−0.0012 (7)
C17	0.0235 (8)	0.0358 (9)	0.0299 (10)	0.0016 (6)	0.0007 (8)	−0.0011 (8)
C18	0.0268 (8)	0.0277 (7)	0.0261 (9)	0.0036 (6)	−0.0008 (7)	0.0001 (7)
C19	0.0321 (9)	0.0337 (9)	0.0403 (12)	0.0032 (7)	−0.0025 (9)	0.0059 (8)

Cl—C16	1.7416 (17)	C7—H7	0.9500
S—O3	1.4397 (16)	C8—C9	1.371 (3)
S—O2	1.4416 (12)	C8—H8	0.9500
S—C1	1.7379 (17)	C9—C10	1.421 (2)
S—C13	1.7663 (17)	C9—H9	0.9500
O1—C12	1.365 (2)	C10—C11	1.409 (3)
O1—C11	1.383 (2)	C12—C19	1.485 (3)
C1—C12	1.366 (2)	C13—C14	1.386 (3)
C1—C2	1.447 (3)	C13—C18	1.394 (2)
C2—C11	1.377 (2)	C14—C15	1.379 (3)
C2—C3	1.418 (3)	C14—H14	0.9500
C3—C4	1.363 (3)	C15—C16	1.396 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.440 (2)	C16—C17	1.378 (3)
C4—H4	0.9500	C17—C18	1.382 (3)
C5—C6	1.414 (3)	C17—H17	0.9500
C5—C10	1.415 (3)	C18—H18	0.9500
C6—C7	1.372 (3)	C19—H19A	0.9800
C6—H6	0.9500	C19—H19B	0.9800
C7—C8	1.404 (3)	C19—H19C	0.9800
O3—S—O2	119.25 (10)	C11—C10—C5	115.35 (15)
O3—S—C1	108.57 (8)	C11—C10—C9	124.35 (18)
O2—S—C1	106.63 (8)	C5—C10—C9	120.30 (18)
O3—S—C13	107.87 (8)	C2—C11—O1	110.85 (17)
O2—S—C13	107.70 (8)	C2—C11—C10	124.68 (17)
C1—S—C13	106.11 (8)	O1—C11—C10	124.47 (14)
C12—O1—C11	107.04 (13)	O1—C12—C1	109.81 (17)
C12—C1—C2	107.78 (16)	O1—C12—C19	115.45 (14)
C12—C1—S	126.43 (15)	C1—C12—C19	134.68 (18)
C2—C1—S	125.51 (13)	C14—C13—C18	121.29 (16)
C11—C2—C3	119.46 (17)	C14—C13—S	120.70 (13)
C11—C2—C1	104.52 (15)	C18—C13—S	117.99 (13)
C3—C2—C1	136.01 (16)	C15—C14—C13	119.40 (16)
C4—C3—C2	118.21 (16)	C15—C14—H14	120.3
C4—C3—H3	120.9	C13—C14—H14	120.3
C2—C3—H3	120.9	C14—C15—C16	118.81 (17)
C3—C4—C5	122.26 (18)	C14—C15—H15	120.6
C3—C4—H4	118.9	C16—C15—H15	120.6
C5—C4—H4	118.9	C17—C16—C15	122.18 (16)
C6—C5—C10	118.56 (17)	C17—C16—Cl	118.45 (14)
C6—C5—C4	121.40 (19)	C15—C16—Cl	119.36 (15)
C10—C5—C4	120.04 (18)	C16—C17—C18	118.83 (16)
C7—C6—C5	120.1 (2)	C16—C17—H17	120.6
C7—C6—H6	119.9	C18—C17—H17	120.6
C5—C6—H6	119.9	C17—C18—C13	119.47 (16)
C6—C7—C8	121.1 (2)	C17—C18—H18	120.3
C6—C7—H7	119.4	C13—C18—H18	120.3
C8—C7—H7	119.4	C12—C19—H19A	109.5
C9—C8—C7	120.42 (18)	C12—C19—H19B	109.5
C9—C8—H8	119.8	H19A—C19—H19B	109.5
C7—C8—H8	119.8	C12—C19—H19C	109.5
C8—C9—C10	119.4 (2)	H19A—C19—H19C	109.5
C8—C9—H9	120.3	H19B—C19—H19C	109.5
C10—C9—H9	120.3
O3—S—C1—C12	8.85 (18)	C1—C2—C11—C10	−178.97 (16)
O2—S—C1—C12	138.51 (16)	C12—O1—C11—C2	−0.01 (19)
C13—S—C1—C12	−106.87 (16)	C12—O1—C11—C10	179.12 (15)
O3—S—C1—C2	−164.41 (14)	C5—C10—C11—C2	−0.7 (2)
O2—S—C1—C2	−34.74 (17)	C9—C10—C11—C2	179.39 (17)
C13—S—C1—C2	79.88 (16)	C5—C10—C11—O1	−179.69 (16)
C12—C1—C2—C11	−0.25 (19)	C9—C10—C11—O1	0.4 (3)
S—C1—C2—C11	174.06 (13)	C11—O1—C12—C1	−0.16 (19)
C12—C1—C2—C3	−179.16 (19)	C11—O1—C12—C19	−177.64 (15)
S—C1—C2—C3	−4.9 (3)	C2—C1—C12—O1	0.26 (19)
C11—C2—C3—C4	0.1 (2)	S—C1—C12—O1	−173.98 (12)
C1—C2—C3—C4	178.91 (18)	C2—C1—C12—C19	177.06 (19)
C2—C3—C4—C5	0.2 (3)	S—C1—C12—C19	2.8 (3)
C3—C4—C5—C6	179.21 (18)	O3—S—C13—C14	147.32 (16)
C3—C4—C5—C10	−0.7 (3)	O2—S—C13—C14	17.39 (18)
C10—C5—C6—C7	−0.5 (3)	C1—S—C13—C14	−96.49 (16)
C4—C5—C6—C7	179.54 (19)	O3—S—C13—C18	−31.49 (16)
C5—C6—C7—C8	−0.1 (3)	O2—S—C13—C18	−161.42 (14)
C6—C7—C8—C9	0.4 (3)	C1—S—C13—C18	84.70 (16)
C7—C8—C9—C10	0.0 (3)	C18—C13—C14—C15	1.3 (3)
C6—C5—C10—C11	−179.00 (16)	S—C13—C14—C15	−177.48 (16)
C4—C5—C10—C11	0.9 (2)	C13—C14—C15—C16	0.1 (3)
C6—C5—C10—C9	0.9 (3)	C14—C15—C16—C17	−1.1 (3)
C4—C5—C10—C9	−179.14 (17)	C14—C15—C16—Cl	177.77 (16)
C8—C9—C10—C11	179.23 (17)	C15—C16—C17—C18	0.7 (3)
C8—C9—C10—C5	−0.7 (3)	Cl—C16—C17—C18	−178.19 (15)
C3—C2—C11—O1	179.29 (14)	C16—C17—C18—C13	0.7 (3)
C1—C2—C11—O1	0.16 (19)	C14—C13—C18—C17	−1.7 (3)
C3—C2—C11—C10	0.2 (3)	S—C13—C18—C17	177.10 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···Cg3i	0.98	2.89	3.488 (3)	120
C8—H8···O2ii	0.95	2.48	3.428 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the O1/C12/C1/C2/C11 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯Cg3i	0.98	2.89	3.488 (3)	120
C8—H8⋯O2ii	0.95	2.48	3.428 (2)	173

Symmetry codes: (i) ; (ii) .