3-[(4-Oxo-4H-thio-chromen-3-yl)meth-yl]-4H-thio-chromen-4-one.

The title mol-ecule, C19H12S2O2, lies on a twofold rotation axis. The thio-chromonone unit is essentially planar, with a maximum deviation of 0.0491 (14) Å. The dihedral angle between the thio-chromenone ring systems is 64.48 (4)°. In the crystal, there are weak π-π stacking inter-actions, with a centroid-centroid distance of 3.7147 (9) Å.

Related literature

For backgound to bis-chromonones, see: Santhosh & Balasubramanian (1991 ▶); Panja et al. (2009 ▶). For related structures, see: Ambartsumyan et al. (2012 ▶); Nyburg et al. (1986 ▶); Li et al. (2010 ▶).

Experimental

Crystal data

C19H12O2S2

M = 336.41

Monoclinic,

a = 11.9480 (5) Å

b = 11.8649 (5) Å

c = 11.1416 (5) Å

β = 108.918 (2)°

V = 1494.14 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.38 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.875, T max = 0.931

5040 measured reflections

1631 independent reflections

1410 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.118

S = 0.88

1631 reflections

109 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.22 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: PLATON (Spek, 2009 ▶) and Jmol (Hanson, 2010 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001906/lh5551sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001906/lh5551Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001906/lh5551Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001906/lh5551Isup4.cml

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

Enhanced figure: interactive version of Fig. 2

C19H12O2S2	F(000) = 696
Mr = 336.41	Dx = 1.495 Mg m−3
Monoclinic, C2/c	Melting point = 489–493 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.9480 (5) Å	Cell parameters from 2970 reflections
b = 11.8649 (5) Å	θ = 2.5–28.2°
c = 11.1416 (5) Å	µ = 0.36 mm−1
β = 108.918 (2)°	T = 298 K
V = 1494.14 (11) Å3	Block, yellow
Z = 4	0.38 × 0.28 × 0.20 mm

Bruker SMART CCD diffractometer	1631 independent reflections
Radiation source: fine-focus sealed tube	1410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
Tmin = 0.875, Tmax = 0.931	k = −15→15
5040 measured reflections	l = −8→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ2(Fo2) + (0.1P)2 + 0.4829P] where P = (Fo2 + 2Fc2)/3
1631 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 e Å−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
C1	0.68093 (16)	0.04971 (13)	−0.09101 (16)	0.0468 (4)
H1	0.6321	0.0231	−0.1689	0.056*
C2	0.79824 (17)	0.02577 (14)	−0.05263 (17)	0.0510 (4)
H2	0.8291	−0.0174	−0.1041	0.061*
C3	0.87278 (15)	0.06556 (14)	0.06363 (17)	0.0481 (4)
H3	0.9535	0.0509	0.0887	0.058*
C4	0.82636 (14)	0.12635 (14)	0.14060 (15)	0.0408 (4)
H4	0.8763	0.1517	0.2186	0.049*
C5	0.70544 (14)	0.15121 (11)	0.10466 (13)	0.0324 (3)
C6	0.66133 (13)	0.21467 (12)	0.19414 (13)	0.0340 (3)
C7	0.53715 (13)	0.24814 (11)	0.15575 (13)	0.0331 (3)
C8	0.45826 (13)	0.22113 (13)	0.04278 (13)	0.0364 (4)
H8	0.3814	0.2467	0.0278	0.044*
C9	0.63250 (13)	0.11413 (12)	−0.01442 (13)	0.0345 (3)
C10	0.5000	0.31787 (18)	0.2500	0.0384 (5)
H18	0.4303 (16)	0.3692 (14)	0.2050 (18)	0.043 (5)*
O1	0.72943 (11)	0.23896 (11)	0.29985 (11)	0.0513 (3)
S1	0.48288 (3)	0.14521 (3)	−0.07650 (3)	0.04148 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0538 (12)	0.0488 (8)	0.0385 (8)	−0.0005 (7)	0.0159 (7)	−0.0020 (6)
C2	0.0548 (12)	0.0519 (9)	0.0530 (9)	0.0107 (8)	0.0265 (8)	0.0016 (7)
C3	0.0365 (10)	0.0540 (9)	0.0568 (10)	0.0096 (7)	0.0190 (8)	0.0131 (8)
C4	0.0316 (10)	0.0500 (8)	0.0374 (8)	0.0021 (6)	0.0066 (7)	0.0101 (6)
C5	0.0314 (9)	0.0372 (7)	0.0278 (7)	−0.0021 (5)	0.0083 (6)	0.0080 (5)
C6	0.0290 (8)	0.0439 (7)	0.0273 (6)	−0.0050 (6)	0.0068 (6)	0.0054 (5)
C7	0.0316 (9)	0.0382 (7)	0.0299 (6)	−0.0017 (6)	0.0103 (6)	0.0062 (5)
C8	0.0269 (9)	0.0492 (8)	0.0319 (7)	0.0002 (6)	0.0079 (6)	0.0060 (5)
C9	0.0340 (9)	0.0386 (7)	0.0297 (7)	−0.0019 (6)	0.0089 (6)	0.0054 (5)
C10	0.0396 (14)	0.0384 (10)	0.0384 (10)	0.000	0.0140 (9)	0.000
O1	0.0351 (7)	0.0820 (8)	0.0311 (6)	−0.0044 (5)	0.0027 (5)	−0.0081 (5)
S1	0.0317 (4)	0.0602 (3)	0.0272 (2)	−0.00364 (15)	0.00220 (19)	−0.00228 (14)

C1—C2	1.356 (3)	C5—C6	1.476 (2)
C1—C9	1.403 (2)	C6—O1	1.2291 (18)
C1—H1	0.9300	C6—C7	1.460 (2)
C2—C3	1.395 (3)	C7—C8	1.344 (2)
C2—H2	0.9300	C7—C10	1.5120 (18)
C3—C4	1.368 (2)	C8—S1	1.7082 (15)
C3—H3	0.9300	C8—H8	0.9300
C4—C5	1.400 (2)	C9—S1	1.7344 (15)
C4—H4	0.9300	C10—C7i	1.5120 (18)
C5—C9	1.401 (2)	C10—H18	1.022 (18)
C2—C1—C9	120.69 (16)	O1—C6—C5	119.75 (14)
C2—C1—H1	119.7	C7—C6—C5	119.50 (12)
C9—C1—H1	119.7	C8—C7—C6	123.18 (13)
C1—C2—C3	120.35 (16)	C8—C7—C10	120.42 (12)
C1—C2—H2	119.8	C6—C7—C10	116.40 (11)
C3—C2—H2	119.8	C7—C8—S1	127.52 (12)
C4—C3—C2	119.60 (15)	C7—C8—H8	116.2
C4—C3—H3	120.2	S1—C8—H8	116.2
C2—C3—H3	120.2	C5—C9—C1	119.64 (15)
C3—C4—C5	121.49 (15)	C5—C9—S1	123.71 (12)
C3—C4—H4	119.3	C1—C9—S1	116.64 (12)
C5—C4—H4	119.3	C7—C10—C7i	113.66 (17)
C4—C5—C9	118.16 (14)	C7—C10—H18	111.2 (10)
C4—C5—C6	118.40 (13)	C7i—C10—H18	106.9 (10)
C9—C5—C6	123.43 (14)	C8—S1—C9	102.54 (7)
O1—C6—C7	120.75 (14)
C9—C1—C2—C3	−0.4 (3)	C6—C7—C8—S1	0.0 (2)
C1—C2—C3—C4	1.8 (3)	C10—C7—C8—S1	179.14 (11)
C2—C3—C4—C5	−0.9 (2)	C4—C5—C9—C1	2.8 (2)
C3—C4—C5—C9	−1.4 (2)	C6—C5—C9—C1	−176.99 (12)
C3—C4—C5—C6	178.43 (13)	C4—C5—C9—S1	−176.06 (10)
C4—C5—C6—O1	−3.8 (2)	C6—C5—C9—S1	4.2 (2)
C9—C5—C6—O1	175.94 (13)	C2—C1—C9—C5	−2.0 (2)
C4—C5—C6—C7	175.98 (12)	C2—C1—C9—S1	176.96 (13)
C9—C5—C6—C7	−4.2 (2)	C8—C7—C10—C7i	93.05 (13)
O1—C6—C7—C8	−178.10 (14)	C6—C7—C10—C7i	−87.80 (11)
C5—C6—C7—C8	2.1 (2)	C7—C8—S1—C9	−0.25 (16)
O1—C6—C7—C10	2.8 (2)	C5—C9—S1—C8	−1.80 (14)
C5—C6—C7—C10	−177.05 (12)	C1—C9—S1—C8	179.31 (11)