(E)-3-[2-(4-Chloro-phenyl-sulfon-yl)vin-yl]-6-methyl-4H-chromen-4-one.

In the title compound, C(18)H(13)ClO(4)S, the mean planes of the chloro-phenyl ring and the S-C=C-C chain are oriented at angles of 52.7 (2) and 51.3 (2)°, respectively, with respect to the sulfonyl (O=S=O) plane. The dihedral angle between the mean planes of the chloro-phenyl group and the benzopyran ring is 80.7 (1)°. The crystal structure is stabilized by two inter-molecular C-H⋯O inter-actions, forming centrosymmetrc dimers, which are linked via a second C-H⋯O inter-action into a chain structure.

Related literature

For the biological properties of sulfonones and for related structures, see: Alonso et al. (2002 ▶); Raju et al. (1996 ▶); Chen et al. (1996 ▶); Mukundam (1990 ▶); Krishnaiah et al. (1995 ▶); Sethu Sankar et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶); Sethu Sankar et al. (2002 ▶). For double-bond character, see: Cruickshank (1961 ▶).

Experimental

Crystal data

C18H13ClO4S

M = 360.79

Monoclinic,

a = 14.383 (3) Å

b = 9.656 (2) Å

c = 12.864 (2) Å

β = 112.630 (2)°

V = 1649.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 298 K

0.20 × 0.15 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.920, T max = 0.960

3643 measured reflections

2774 independent reflections

2088 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.245

S = 1.13

2774 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and PARST (Nardelli, 1995 ▶)’.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041300/su2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041300/su2142Isup2.hkl

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

C18H13ClO4S	F(000) = 744
Mr = 360.79	Dx = 1.453 Mg m−3Dm = 1.45 Mg m−3Dm measured by not measured
Monoclinic, P2/c	Melting point: 500.15 K
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.383 (3) Å	Cell parameters from 3859 reflections
b = 9.656 (2) Å	θ = 2–25°
c = 12.864 (2) Å	µ = 0.38 mm−1
β = 112.630 (2)°	T = 298 K
V = 1649.0 (5) Å3	Needle, colorless
Z = 4	0.20 × 0.15 × 0.08 mm

Bruker SMART CCD diffractometer	2774 independent reflections
Radiation source: fine-focus sealed tube	2088 reflections with I > 2σ(I)
graphite	Rint = 0.081
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→16
Tmin = 0.920, Tmax = 0.960	k = −11→1
3643 measured reflections	l = −1→15

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)] = 0.073	H-atom parameters constrained
wR(F2) = 0.245	w = 1/[σ2(Fo2) + (0.1424P)2 + 0.7321P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.008
2774 reflections	Δρmax = 0.45 e Å−3
219 parameters	Δρmin = −0.62 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (3)

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
S11	0.79047 (7)	0.45722 (10)	0.55267 (8)	0.0653 (4)
Cl1	0.43852 (10)	0.82582 (16)	0.56710 (14)	0.1059 (6)
O2	1.0746 (2)	0.7324 (3)	0.6813 (2)	0.0788 (9)
C4'	1.1219 (3)	0.8837 (4)	0.5657 (3)	0.0574 (8)
C4	1.0592 (3)	0.7751 (4)	0.5861 (3)	0.0616 (9)
C3	0.9782 (3)	0.7252 (4)	0.4844 (3)	0.0583 (9)
O4	0.7593 (2)	0.4008 (3)	0.4412 (3)	0.0777 (8)
C6	1.2619 (3)	1.0455 (4)	0.6351 (4)	0.0722 (11)
C12	0.6889 (3)	0.5579 (4)	0.5576 (3)	0.0613 (9)
O1	1.0265 (2)	0.8753 (3)	0.3664 (2)	0.0728 (8)
C9	0.9046 (3)	0.6224 (4)	0.4845 (3)	0.0636 (9)
H9	0.8661	0.5830	0.4152	0.076*
C2	0.9698 (3)	0.7770 (4)	0.3830 (3)	0.0684 (10)
H2	0.9195	0.7399	0.3194	0.082*
C10	0.8861 (3)	0.5783 (4)	0.5725 (3)	0.0629 (9)
H10	0.9238	0.6118	0.6442	0.075*
C8'	1.1045 (3)	0.9293 (4)	0.4586 (3)	0.0627 (9)
C8	1.1617 (3)	1.0315 (5)	0.4360 (4)	0.0741 (11)
H8	1.1467	1.0619	0.3627	0.089*
C13	0.6932 (3)	0.6080 (5)	0.6603 (3)	0.0722 (11)
H13	0.7475	0.5861	0.7263	0.087*
C16	0.5307 (3)	0.6686 (5)	0.4631 (4)	0.0756 (11)
H16	0.4755	0.6884	0.3975	0.091*
O3	0.8228 (3)	0.3653 (3)	0.6485 (3)	0.0856 (9)
C5	1.2020 (3)	0.9448 (4)	0.6535 (3)	0.0660 (10)
H5	1.2156	0.9164	0.7270	0.079*
C7	1.2404 (3)	1.0864 (5)	0.5239 (4)	0.0768 (12)
H7	1.2809	1.1527	0.5096	0.092*
C15	0.5361 (3)	0.7201 (5)	0.5646 (4)	0.0753 (11)
C17	0.6081 (3)	0.5870 (4)	0.4594 (3)	0.0670 (10)
H17	0.6057	0.5520	0.3911	0.080*
C14	0.6162 (3)	0.6907 (5)	0.6636 (4)	0.0801 (12)
H14	0.6182	0.7262	0.7317	0.096*
C18	1.3464 (4)	1.1129 (7)	0.7322 (5)	0.1089 (18)
H18A	1.3531	1.0681	0.8014	0.163*
H18B	1.3313	1.2092	0.7361	0.163*
H18C	1.4083	1.1042	0.7208	0.163*

	U11	U22	U33	U12	U13	U23
S11	0.0613 (7)	0.0646 (7)	0.0748 (7)	0.0011 (4)	0.0317 (5)	0.0050 (4)
Cl1	0.0822 (9)	0.1144 (11)	0.1406 (12)	0.0215 (7)	0.0644 (8)	0.0071 (8)
O2	0.0699 (17)	0.113 (2)	0.0547 (14)	−0.0154 (16)	0.0252 (12)	0.0102 (14)
C4'	0.0538 (19)	0.069 (2)	0.0583 (19)	0.0042 (16)	0.0315 (16)	−0.0014 (15)
C4	0.0542 (19)	0.082 (3)	0.0558 (19)	0.0068 (17)	0.0296 (15)	0.0023 (16)
C3	0.057 (2)	0.067 (2)	0.0578 (18)	0.0020 (16)	0.0298 (16)	−0.0019 (15)
O4	0.0782 (19)	0.0796 (19)	0.0824 (19)	−0.0013 (15)	0.0389 (15)	−0.0088 (14)
C6	0.058 (2)	0.079 (3)	0.084 (3)	−0.0046 (18)	0.032 (2)	−0.009 (2)
C12	0.056 (2)	0.065 (2)	0.070 (2)	−0.0070 (16)	0.0308 (17)	0.0014 (16)
O1	0.0742 (18)	0.095 (2)	0.0545 (14)	−0.0101 (15)	0.0307 (13)	0.0027 (12)
C9	0.061 (2)	0.069 (2)	0.066 (2)	0.0088 (17)	0.0309 (17)	−0.0005 (17)
C2	0.069 (2)	0.085 (3)	0.0552 (19)	−0.004 (2)	0.0284 (17)	−0.0076 (18)
C10	0.055 (2)	0.067 (2)	0.071 (2)	0.0021 (17)	0.0300 (17)	0.0010 (17)
C8'	0.060 (2)	0.076 (2)	0.063 (2)	0.0023 (18)	0.0347 (18)	−0.0033 (17)
C8	0.075 (3)	0.086 (3)	0.074 (3)	0.000 (2)	0.043 (2)	0.009 (2)
C13	0.060 (2)	0.093 (3)	0.064 (2)	−0.005 (2)	0.0241 (18)	−0.0007 (19)
C16	0.057 (2)	0.092 (3)	0.076 (2)	−0.001 (2)	0.0240 (19)	0.011 (2)
O3	0.084 (2)	0.081 (2)	0.094 (2)	0.0081 (16)	0.0366 (16)	0.0270 (16)
C5	0.058 (2)	0.081 (3)	0.064 (2)	0.0021 (18)	0.0292 (17)	0.0012 (17)
C7	0.072 (3)	0.076 (3)	0.099 (3)	−0.004 (2)	0.051 (2)	−0.002 (2)
C15	0.062 (2)	0.078 (3)	0.101 (3)	−0.003 (2)	0.048 (2)	0.005 (2)
C17	0.061 (2)	0.079 (3)	0.063 (2)	−0.0004 (19)	0.0264 (18)	0.0054 (17)
C14	0.072 (3)	0.098 (3)	0.081 (3)	−0.005 (2)	0.041 (2)	−0.013 (2)
C18	0.084 (3)	0.123 (5)	0.118 (4)	−0.038 (3)	0.037 (3)	−0.019 (3)

S11—O4	1.435 (3)	C9—H9	0.9300
S11—O3	1.443 (3)	C2—H2	0.9300
S11—C10	1.747 (4)	C10—H10	0.9300
S11—C12	1.776 (4)	C8'—C8	1.386 (6)
Cl1—C15	1.746 (4)	C8—C7	1.362 (6)
O2—C4	1.229 (4)	C8—H8	0.9300
C4'—C8'	1.375 (5)	C13—C14	1.380 (6)
C4'—C5	1.396 (5)	C13—H13	0.9300
C4'—C4	1.471 (5)	C16—C15	1.371 (6)
C4—C3	1.459 (5)	C16—C17	1.379 (6)
C3—C2	1.358 (5)	C16—H16	0.9300
C3—C9	1.451 (5)	C5—H5	0.9300
C6—C5	1.378 (5)	C7—H7	0.9300
C6—C7	1.400 (6)	C15—C14	1.378 (7)
C6—C18	1.514 (7)	C17—H17	0.9300
C12—C17	1.377 (5)	C14—H14	0.9300
C12—C13	1.386 (5)	C18—H18A	0.9600
O1—C2	1.322 (5)	C18—H18B	0.9600
O1—C8'	1.383 (5)	C18—H18C	0.9600
C9—C10	1.329 (5)
O4—S11—O3	119.6 (2)	C4'—C8'—C8	122.9 (4)
O4—S11—C10	109.03 (18)	O1—C8'—C8	116.1 (3)
O3—S11—C10	108.1 (2)	C7—C8—C8'	118.4 (4)
O4—S11—C12	107.37 (18)	C7—C8—H8	120.8
O3—S11—C12	107.75 (18)	C8'—C8—H8	120.8
C10—S11—C12	103.90 (18)	C14—C13—C12	119.3 (4)
C8'—C4'—C5	116.8 (3)	C14—C13—H13	120.3
C8'—C4'—C4	121.2 (3)	C12—C13—H13	120.3
C5—C4'—C4	121.9 (3)	C15—C16—C17	119.3 (4)
O2—C4—C3	124.0 (4)	C15—C16—H16	120.3
O2—C4—C4'	121.9 (3)	C17—C16—H16	120.3
C3—C4—C4'	114.1 (3)	C6—C5—C4'	122.3 (4)
C2—C3—C9	117.2 (3)	C6—C5—H5	118.8
C2—C3—C4	119.0 (3)	C4'—C5—H5	118.8
C9—C3—C4	123.8 (3)	C8—C7—C6	121.6 (4)
C5—C6—C7	117.9 (4)	C8—C7—H7	119.2
C5—C6—C18	121.2 (4)	C6—C7—H7	119.2
C7—C6—C18	120.9 (4)	C16—C15—C14	121.8 (4)
C17—C12—C13	121.0 (4)	C16—C15—Cl1	118.6 (4)
C17—C12—S11	119.6 (3)	C14—C15—Cl1	119.7 (4)
C13—C12—S11	119.3 (3)	C12—C17—C16	119.5 (4)
C2—O1—C8'	118.6 (3)	C12—C17—H17	120.3
C10—C9—C3	127.2 (4)	C16—C17—H17	120.3
C10—C9—H9	116.4	C15—C14—C13	119.0 (4)
C3—C9—H9	116.4	C15—C14—H14	120.5
O1—C2—C3	126.0 (4)	C13—C14—H14	120.5
O1—C2—H2	117.0	C6—C18—H18A	109.5
C3—C2—H2	117.0	C6—C18—H18B	109.5
C9—C10—S11	119.6 (3)	H18A—C18—H18B	109.5
C9—C10—H10	120.2	C6—C18—H18C	109.5
S11—C10—H10	120.2	H18A—C18—H18C	109.5
C4'—C8'—O1	121.0 (3)	H18B—C18—H18C	109.5
C8'—C4'—C4—O2	179.2 (4)	C4—C4'—C8'—O1	0.7 (5)
C5—C4'—C4—O2	−0.3 (6)	C5—C4'—C8'—C8	−0.6 (6)
C8'—C4'—C4—C3	−1.3 (5)	C4—C4'—C8'—C8	179.8 (4)
C5—C4'—C4—C3	179.2 (3)	C2—O1—C8'—C4'	−1.1 (5)
O2—C4—C3—C2	−178.2 (4)	C2—O1—C8'—C8	179.7 (3)
C4'—C4—C3—C2	2.3 (5)	C4'—C8'—C8—C7	1.9 (6)
O2—C4—C3—C9	2.0 (6)	O1—C8'—C8—C7	−178.9 (4)
C4'—C4—C3—C9	−177.5 (3)	C17—C12—C13—C14	−1.3 (6)
O4—S11—C12—C17	−10.5 (4)	S11—C12—C13—C14	177.5 (3)
O3—S11—C12—C17	−140.6 (3)	C7—C6—C5—C4'	−0.2 (6)
C10—S11—C12—C17	104.9 (3)	C18—C6—C5—C4'	178.2 (4)
O4—S11—C12—C13	170.7 (3)	C8'—C4'—C5—C6	−0.3 (6)
O3—S11—C12—C13	40.6 (4)	C4—C4'—C5—C6	179.3 (3)
C10—S11—C12—C13	−73.9 (3)	C8'—C8—C7—C6	−2.3 (7)
C2—C3—C9—C10	−165.8 (4)	C5—C6—C7—C8	1.5 (6)
C4—C3—C9—C10	14.0 (6)	C18—C6—C7—C8	−176.8 (5)
C8'—O1—C2—C3	2.4 (6)	C17—C16—C15—C14	−1.1 (7)
C9—C3—C2—O1	176.7 (4)	C17—C16—C15—Cl1	178.8 (3)
C4—C3—C2—O1	−3.0 (6)	C13—C12—C17—C16	0.7 (6)
C3—C9—C10—S11	177.8 (3)	S11—C12—C17—C16	−178.1 (3)
O4—S11—C10—C9	12.3 (4)	C15—C16—C17—C12	0.5 (6)
O3—S11—C10—C9	143.8 (3)	C16—C15—C14—C13	0.4 (7)
C12—S11—C10—C9	−101.9 (3)	Cl1—C15—C14—C13	−179.4 (3)
C5—C4'—C8'—O1	−179.7 (3)	C12—C13—C14—C15	0.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.93	2.33	3.248 (5)	167
C10—H10···O2ii	0.93	2.52	3.344 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.33	3.248 (5)	167
C10—H10⋯O2ii	0.93	2.52	3.344 (5)	148

Symmetry codes: (i) ; (ii) .