2-Methyl-5,6-methyl-enedi-oxy-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(16)H(12)O(5)S, was prepared by oxidation of 2-methyl-5,6-methyl-ene-di-oxy-3-phenyl-sulfanyl-1-benzo-furan with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 83.64 (4)° with the mean plane of the 5,6-(methyl-ene-di-oxy)-benzo-furan fragment. The crystal structure is stabilized by C-H⋯π inter-actions between a benzene H atom of the 5,6-(methyl-ene-di-oxy)-benzo-furan unit and the phenyl ring of the phenyl-sulfonyl substituent. Additionally, the crystal structure exhibits inter- and intra-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 5,6-(methyl­ene­di­oxy)­benzo­furan compounds, see: Choi et al. (2007a ▶,b ▶).

Experimental

Crystal data

C16H12O5S

M = 316.32

Triclinic,

a = 7.4401 (3) Å

b = 8.8505 (4) Å

c = 11.2406 (5) Å

α = 89.801 (1)°

β = 72.565 (1)°

γ = 79.257 (1)°

V = 692.71 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 173 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

6000 measured reflections

2983 independent reflections

2746 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.05

2983 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.38 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/S160053680800980X/bh2167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800980X/bh2167Isup2.hkl

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

C16H12O5S	Z = 2
Mr = 316.32	F000 = 328
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Melting point = 442–443 K
a = 7.4401 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.8505 (4) Å	Cell parameters from 4646 reflections
c = 11.2406 (5) Å	θ = 2.4–28.2º
α = 89.801 (1)º	µ = 0.26 mm−1
β = 72.565 (1)º	T = 173 (2) K
γ = 79.257 (1)º	Block, colourless
V = 692.71 (5) Å3	0.40 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2746 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.9º
φ and ω scans	h = −9→9
Absorption correction: none	k = −11→11
6000 measured reflections	l = −14→13

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.3658P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2983 reflections	Δρmax = 0.32 e Å−3
200 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S	0.36347 (5)	0.72181 (4)	0.70730 (3)	0.02587 (12)
O1	0.16796 (16)	1.11741 (12)	0.58768 (11)	0.0317 (3)
O2	0.46615 (19)	0.74239 (14)	0.16742 (10)	0.0364 (3)
O3	0.3156 (2)	0.98837 (15)	0.14228 (11)	0.0399 (3)
O4	0.52005 (16)	0.61904 (13)	0.62032 (10)	0.0313 (3)
O5	0.38566 (18)	0.77361 (16)	0.82216 (11)	0.0388 (3)
C1	0.2989 (2)	0.88120 (17)	0.62765 (14)	0.0250 (3)
C2	0.3186 (2)	0.88013 (17)	0.49576 (14)	0.0236 (3)
C3	0.4015 (2)	0.76992 (17)	0.39479 (13)	0.0249 (3)
H3	0.4609	0.6676	0.4039	0.030*
C4	0.3893 (2)	0.82284 (18)	0.28230 (14)	0.0266 (3)
C5	0.3014 (2)	0.97239 (19)	0.26672 (15)	0.0290 (3)
C6	0.2216 (2)	1.08254 (18)	0.36244 (16)	0.0311 (3)
H6	0.1631	1.1847	0.3521	0.037*
C7	0.2350 (2)	1.02901 (17)	0.47682 (15)	0.0263 (3)
C8	0.2083 (2)	1.02469 (19)	0.67807 (15)	0.0299 (3)
C9	0.1598 (2)	0.63445 (17)	0.74530 (14)	0.0259 (3)
C10	0.1304 (2)	0.54383 (18)	0.65468 (16)	0.0311 (3)
H10	0.2229	0.5230	0.5745	0.037*
C11	−0.0363 (3)	0.4846 (2)	0.6836 (2)	0.0397 (4)
H11	−0.0595	0.4236	0.6225	0.048*
C12	−0.1687 (3)	0.5136 (2)	0.8009 (2)	0.0443 (5)
H12	−0.2836	0.4739	0.8194	0.053*
C13	−0.1355 (3)	0.6000 (2)	0.89174 (19)	0.0455 (5)
H13	−0.2253	0.6162	0.9731	0.055*
C14	0.0288 (3)	0.6630 (2)	0.86401 (16)	0.0366 (4)
H14	0.0512	0.7245	0.9252	0.044*
C15	0.4011 (3)	0.8388 (2)	0.08173 (17)	0.0467 (5)
H15A	0.3056	0.7952	0.0546	0.056*
H15B	0.5103	0.8463	0.0071	0.056*
C16	0.1447 (3)	1.0983 (2)	0.80603 (17)	0.0421 (4)
H16A	0.0064	1.1036	0.8430	0.063*
H16B	0.1720	1.2027	0.8021	0.063*
H16C	0.2137	1.0374	0.8574	0.063*

	U11	U22	U33	U12	U13	U23
S	0.0256 (2)	0.0340 (2)	0.01994 (19)	−0.00685 (15)	−0.00916 (14)	0.00132 (14)
O1	0.0297 (6)	0.0249 (5)	0.0371 (6)	−0.0040 (4)	−0.0060 (5)	−0.0037 (5)
O2	0.0539 (8)	0.0377 (6)	0.0213 (5)	−0.0141 (6)	−0.0137 (5)	0.0014 (5)
O3	0.0539 (8)	0.0439 (7)	0.0329 (6)	−0.0191 (6)	−0.0238 (6)	0.0157 (5)
O4	0.0265 (6)	0.0366 (6)	0.0286 (6)	−0.0008 (5)	−0.0082 (4)	0.0029 (5)
O5	0.0428 (7)	0.0556 (8)	0.0249 (6)	−0.0163 (6)	−0.0164 (5)	0.0010 (5)
C1	0.0237 (7)	0.0285 (7)	0.0236 (7)	−0.0070 (6)	−0.0071 (5)	−0.0009 (6)
C2	0.0223 (7)	0.0257 (7)	0.0243 (7)	−0.0070 (5)	−0.0080 (5)	0.0024 (5)
C3	0.0284 (7)	0.0238 (7)	0.0236 (7)	−0.0054 (6)	−0.0091 (6)	0.0014 (6)
C4	0.0299 (7)	0.0295 (8)	0.0236 (7)	−0.0124 (6)	−0.0090 (6)	0.0024 (6)
C5	0.0296 (8)	0.0355 (8)	0.0291 (8)	−0.0148 (6)	−0.0145 (6)	0.0115 (6)
C6	0.0284 (8)	0.0262 (7)	0.0418 (9)	−0.0072 (6)	−0.0142 (7)	0.0107 (7)
C7	0.0226 (7)	0.0244 (7)	0.0319 (8)	−0.0065 (5)	−0.0069 (6)	−0.0002 (6)
C8	0.0252 (7)	0.0329 (8)	0.0304 (8)	−0.0093 (6)	−0.0044 (6)	−0.0045 (6)
C9	0.0254 (7)	0.0273 (7)	0.0257 (7)	−0.0053 (6)	−0.0089 (6)	0.0048 (6)
C10	0.0328 (8)	0.0276 (8)	0.0336 (8)	−0.0028 (6)	−0.0131 (7)	0.0014 (6)
C11	0.0406 (9)	0.0276 (8)	0.0580 (11)	−0.0083 (7)	−0.0244 (9)	0.0041 (8)
C12	0.0325 (9)	0.0333 (9)	0.0694 (13)	−0.0113 (7)	−0.0160 (9)	0.0172 (9)
C13	0.0332 (9)	0.0470 (11)	0.0467 (11)	−0.0073 (8)	0.0017 (8)	0.0132 (8)
C14	0.0366 (9)	0.0406 (9)	0.0290 (8)	−0.0078 (7)	−0.0045 (7)	0.0023 (7)
C15	0.0520 (11)	0.0598 (12)	0.0258 (9)	−0.0075 (9)	−0.0105 (8)	0.0105 (8)
C16	0.0381 (9)	0.0464 (10)	0.0364 (9)	−0.0107 (8)	−0.0017 (7)	−0.0164 (8)

S—O5	1.4369 (12)	C6—H6	0.9500
S—O4	1.4384 (12)	C8—C16	1.484 (2)
S—C1	1.7374 (16)	C9—C14	1.388 (2)
S—C9	1.7674 (15)	C9—C10	1.390 (2)
O1—C8	1.371 (2)	C10—C11	1.385 (2)
O1—C7	1.3794 (18)	C10—H10	0.9500
O2—C4	1.3833 (18)	C11—C12	1.380 (3)
O2—C15	1.418 (2)	C11—H11	0.9500
O3—C5	1.3797 (19)	C12—C13	1.384 (3)
O3—C15	1.433 (2)	C12—H12	0.9500
C1—C8	1.358 (2)	C13—C14	1.388 (3)
C1—C2	1.445 (2)	C13—H13	0.9500
C2—C7	1.393 (2)	C14—H14	0.9500
C2—C3	1.409 (2)	C15—H15A	0.9900
C3—C4	1.369 (2)	C15—H15B	0.9900
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.398 (2)	C16—H16B	0.9800
C5—C6	1.367 (2)	C16—H16C	0.9800
C6—C7	1.394 (2)
O5—S—O4	119.53 (7)	O1—C8—C16	115.53 (15)
O5—S—C1	108.96 (8)	C14—C9—C10	121.50 (15)
O4—S—C1	107.55 (7)	C14—C9—S	118.94 (13)
O5—S—C9	107.76 (7)	C10—C9—S	119.51 (12)
O4—S—C9	108.26 (7)	C11—C10—C9	118.71 (16)
C1—S—C9	103.65 (7)	C11—C10—H10	120.6
C8—O1—C7	107.02 (12)	C9—C10—H10	120.6
C4—O2—C15	105.85 (13)	C12—C11—C10	120.33 (17)
C5—O3—C15	105.87 (13)	C12—C11—H11	119.8
C8—C1—C2	107.71 (14)	C10—C11—H11	119.8
C8—C1—S	126.84 (12)	C11—C12—C13	120.56 (17)
C2—C1—S	125.26 (11)	C11—C12—H12	119.7
C7—C2—C3	120.48 (14)	C13—C12—H12	119.7
C7—C2—C1	104.66 (13)	C12—C13—C14	120.04 (18)
C3—C2—C1	134.85 (14)	C12—C13—H13	120.0
C4—C3—C2	114.24 (14)	C14—C13—H13	120.0
C4—C3—H3	122.9	C9—C14—C13	118.81 (17)
C2—C3—H3	122.9	C9—C14—H14	120.6
C3—C4—O2	126.58 (14)	C13—C14—H14	120.6
C3—C4—C5	123.90 (14)	O2—C15—O3	108.47 (14)
O2—C4—C5	109.48 (13)	O2—C15—H15A	110.0
C6—C5—O3	127.47 (15)	O3—C15—H15A	110.0
C6—C5—C4	123.31 (14)	O2—C15—H15B	110.0
O3—C5—C4	109.19 (14)	O3—C15—H15B	110.0
C5—C6—C7	112.80 (14)	H15A—C15—H15B	108.4
C5—C6—H6	123.6	C8—C16—H16A	109.5
C7—C6—H6	123.6	C8—C16—H16B	109.5
O1—C7—C2	110.33 (13)	H16A—C16—H16B	109.5
O1—C7—C6	124.42 (14)	C8—C16—H16C	109.5
C2—C7—C6	125.25 (15)	H16A—C16—H16C	109.5
C1—C8—O1	110.29 (14)	H16B—C16—H16C	109.5
C1—C8—C16	134.18 (17)
O5—S—C1—C8	−25.07 (16)	C1—C2—C7—O1	0.06 (16)
O4—S—C1—C8	−156.01 (14)	C3—C2—C7—C6	1.1 (2)
C9—S—C1—C8	89.47 (15)	C1—C2—C7—C6	179.64 (14)
O5—S—C1—C2	160.50 (12)	C5—C6—C7—O1	179.15 (13)
O4—S—C1—C2	29.55 (15)	C5—C6—C7—C2	−0.4 (2)
C9—S—C1—C2	−84.96 (14)	C2—C1—C8—O1	−0.16 (17)
C8—C1—C2—C7	0.06 (16)	S—C1—C8—O1	−175.39 (11)
S—C1—C2—C7	175.39 (11)	C2—C1—C8—C16	179.14 (17)
C8—C1—C2—C3	178.25 (16)	S—C1—C8—C16	3.9 (3)
S—C1—C2—C3	−6.4 (3)	C7—O1—C8—C1	0.19 (17)
C7—C2—C3—C4	−0.6 (2)	C7—O1—C8—C16	−179.25 (13)
C1—C2—C3—C4	−178.60 (15)	O5—S—C9—C14	17.03 (15)
C2—C3—C4—O2	176.68 (14)	O4—S—C9—C14	147.62 (13)
C2—C3—C4—C5	−0.5 (2)	C1—S—C9—C14	−98.37 (14)
C15—O2—C4—C3	174.65 (16)	O5—S—C9—C10	−165.42 (12)
C15—O2—C4—C5	−7.83 (18)	O4—S—C9—C10	−34.83 (14)
C15—O3—C5—C6	−177.05 (17)	C1—S—C9—C10	79.18 (13)
C15—O3—C5—C4	4.93 (18)	C14—C9—C10—C11	1.7 (2)
C3—C4—C5—C6	1.3 (2)	S—C9—C10—C11	−175.83 (12)
O2—C4—C5—C6	−176.29 (14)	C9—C10—C11—C12	−0.9 (2)
C3—C4—C5—O3	179.42 (14)	C10—C11—C12—C13	−1.1 (3)
O2—C4—C5—O3	1.82 (17)	C11—C12—C13—C14	2.3 (3)
O3—C5—C6—C7	−178.56 (14)	C10—C9—C14—C13	−0.5 (3)
C4—C5—C6—C7	−0.8 (2)	S—C9—C14—C13	177.04 (14)
C8—O1—C7—C2	−0.15 (16)	C12—C13—C14—C9	−1.5 (3)
C8—O1—C7—C6	−179.74 (14)	C4—O2—C15—O3	10.86 (19)
C3—C2—C7—O1	−178.45 (12)	C5—O3—C15—O2	−9.81 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgi	0.95	2.83	3.722 (3)	152
C3—H3···O4ii	0.95	2.53	3.379 (2)	150
C12—H12···O2iii	0.95	2.53	3.398 (2)	153
C16—H16C···O5	0.98	2.42	3.127 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgi	0.95	2.83	3.722 (3)	152
C3—H3⋯O4ii	0.95	2.53	3.379 (2)	150
C12—H12⋯O2iii	0.95	2.53	3.398 (2)	153
C16—H16C⋯O5	0.98	2.42	3.127 (3)	129

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