3-(1,3-Dithio-lan-2-yl-idene)-1-(4-meth-oxy-phen-yl)pyridine-2,4(1H,3H)-dione.

In the title compound, C(15)H(13)NO(3)S(2), the dithiol-ane ring adopts a twisted conformation. The mol-ecule exhibits a V-shaped conformation, with a dihedral angle of 79.05 (7)° between the benzene ring and the pyridine ring. In the crystal, C-H⋯O inter-actions are observed.

Related literature

For the synthesis, see: Li et al. (2008 ▶). For background to N-substituted pyridine compounds and their potential use in medicinal chemistry, see: Kim et al. (2008 ▶); Zhu et al. (2006 ▶)

Experimental

Crystal data

C15H13NO3S2

M = 319.40

Monoclinic,

a = 5.322 (2) Å

b = 27.521 (11) Å

c = 10.065 (4) Å

β = 100.831 (5)°

V = 1448.0 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.35 × 0.29 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.892, T max = 0.912

12346 measured reflections

2905 independent reflections

1973 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.08

2905 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033009/ff2024sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033009/ff2024Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033009/ff2024Isup3.cml

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

C15H13NO3S2	Z = 4
Mr = 319.40	F(000) = 664
Monoclinic, P21/n	Dx = 1.453 Mg m−3
Hall symbol: -p 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.322 (2) Å	θ = 2.7–27.1°
b = 27.521 (11) Å	µ = 0.38 mm−1
c = 10.065 (4) Å	T = 293 K
β = 100.831 (5)°	Block, yellow
V = 1448.0 (10) Å3	0.35 × 0.29 × 0.28 mm

Bruker APEXII CCD diffractometer	2905 independent reflections
Radiation source: fine-focus sealed tube	1973 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω scans	θmax = 26.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→6
Tmin = 0.892, Tmax = 0.912	k = −34→33
12346 measured reflections	l = −12→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0581P)2] where P = (Fo2 + 2Fc2)/3
2905 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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
S2	0.24453 (13)	0.13081 (2)	1.20138 (7)	0.0510 (2)
S1	0.45027 (15)	0.05404 (2)	1.05151 (8)	0.0620 (3)
N1	0.6394 (4)	0.23410 (7)	0.9727 (2)	0.0462 (5)
O2	0.3943 (3)	0.21607 (6)	1.12752 (18)	0.0595 (5)
O1	0.7470 (4)	0.09067 (7)	0.89857 (19)	0.0670 (5)
O3	0.5220 (4)	0.43233 (7)	1.0589 (2)	0.0736 (6)
C13	0.4297 (4)	0.11562 (9)	1.0831 (2)	0.0418 (6)
C11	0.5545 (4)	0.14965 (8)	1.0179 (2)	0.0419 (6)
C4	0.6118 (5)	0.28548 (8)	0.9964 (2)	0.0452 (6)
C12	0.5218 (4)	0.20108 (8)	1.0456 (2)	0.0436 (6)
C5	0.3930 (5)	0.30960 (10)	0.9369 (3)	0.0586 (7)
H5	0.2618	0.2929	0.8811	0.070*
C6	0.3694 (5)	0.35832 (10)	0.9602 (3)	0.0629 (8)
H6	0.2219	0.3747	0.9197	0.075*
C3	0.8034 (5)	0.31005 (9)	1.0787 (2)	0.0516 (6)
H3	0.9504	0.2936	1.1193	0.062*
C7	0.5642 (5)	0.38348 (9)	1.0438 (3)	0.0528 (6)
C10	0.7144 (5)	0.13424 (10)	0.9219 (2)	0.0484 (6)
C8	0.7884 (5)	0.21885 (10)	0.8818 (2)	0.0522 (7)
H8	0.8649	0.2423	0.8362	0.063*
C9	0.8276 (5)	0.17249 (10)	0.8563 (3)	0.0525 (6)
H9	0.9309	0.1646	0.7944	0.063*
C2	0.7809 (5)	0.35902 (9)	1.1022 (3)	0.0566 (7)
H2	0.9130	0.3755	1.1578	0.068*
C14	0.2073 (6)	0.03558 (11)	1.1426 (4)	0.0849 (10)
H14A	0.0436	0.0341	1.0811	0.102*
H14B	0.2466	0.0034	1.1800	0.102*
C15	0.1914 (7)	0.06899 (10)	1.2493 (4)	0.0856 (11)
H15A	0.3178	0.0604	1.3284	0.103*
H15B	0.0236	0.0665	1.2733	0.103*
C1	0.7075 (8)	0.45886 (12)	1.1489 (4)	0.1129 (14)
H1A	0.6552	0.4922	1.1501	0.169*
H1B	0.8688	0.4570	1.1197	0.169*
H1C	0.7246	0.4454	1.2382	0.169*

	U11	U22	U33	U12	U13	U23
S2	0.0644 (4)	0.0431 (4)	0.0516 (4)	−0.0063 (3)	0.0267 (3)	−0.0052 (3)
S1	0.0783 (5)	0.0396 (4)	0.0762 (5)	0.0019 (3)	0.0355 (4)	−0.0043 (3)
N1	0.0534 (12)	0.0425 (12)	0.0455 (12)	−0.0073 (9)	0.0167 (10)	−0.0016 (9)
O2	0.0830 (13)	0.0423 (10)	0.0643 (12)	−0.0049 (9)	0.0424 (11)	−0.0071 (8)
O1	0.0835 (14)	0.0528 (12)	0.0735 (13)	0.0071 (10)	0.0375 (11)	−0.0083 (10)
O3	0.0977 (16)	0.0497 (12)	0.0752 (14)	0.0139 (11)	0.0208 (12)	0.0030 (10)
C13	0.0456 (14)	0.0412 (13)	0.0390 (13)	0.0025 (10)	0.0093 (10)	−0.0032 (10)
C11	0.0436 (13)	0.0427 (13)	0.0409 (14)	0.0002 (11)	0.0112 (11)	−0.0011 (11)
C4	0.0471 (14)	0.0448 (15)	0.0462 (14)	−0.0043 (11)	0.0152 (11)	0.0055 (11)
C12	0.0495 (14)	0.0439 (14)	0.0389 (13)	−0.0055 (11)	0.0126 (11)	−0.0008 (11)
C5	0.0442 (15)	0.0590 (18)	0.0696 (18)	−0.0090 (13)	0.0031 (13)	0.0087 (14)
C6	0.0475 (16)	0.0624 (18)	0.079 (2)	0.0068 (14)	0.0109 (14)	0.0181 (16)
C3	0.0512 (15)	0.0476 (16)	0.0530 (16)	0.0020 (12)	0.0020 (12)	0.0010 (12)
C7	0.0675 (18)	0.0476 (15)	0.0478 (15)	0.0033 (14)	0.0220 (13)	0.0053 (12)
C10	0.0489 (15)	0.0541 (17)	0.0440 (15)	0.0022 (12)	0.0136 (11)	−0.0026 (12)
C8	0.0502 (15)	0.0654 (18)	0.0446 (15)	−0.0103 (13)	0.0179 (12)	0.0012 (13)
C9	0.0538 (15)	0.0616 (17)	0.0471 (15)	−0.0036 (13)	0.0224 (12)	−0.0070 (13)
C2	0.0629 (17)	0.0517 (17)	0.0518 (16)	−0.0027 (13)	0.0017 (13)	−0.0031 (13)
C14	0.111 (3)	0.0483 (17)	0.110 (3)	−0.0121 (17)	0.058 (2)	−0.0059 (18)
C15	0.126 (3)	0.0514 (18)	0.096 (2)	−0.0232 (18)	0.065 (2)	−0.0066 (17)
C1	0.166 (4)	0.060 (2)	0.101 (3)	0.015 (2)	−0.005 (3)	−0.026 (2)

S2—C13	1.733 (2)	C6—C7	1.391 (4)
S2—C15	1.805 (3)	C6—H6	0.9300
S1—C13	1.732 (3)	C3—C2	1.377 (3)
S1—C14	1.793 (3)	C3—H3	0.9300
N1—C8	1.384 (3)	C7—C2	1.369 (3)
N1—C12	1.389 (3)	C10—C9	1.434 (3)
N1—C4	1.446 (3)	C8—C9	1.326 (3)
O2—C12	1.233 (3)	C8—H8	0.9300
O1—C10	1.240 (3)	C9—H9	0.9300
O3—C7	1.376 (3)	C2—H2	0.9300
O3—C1	1.412 (4)	C14—C15	1.429 (4)
C13—C11	1.383 (3)	C14—H14A	0.9700
C11—C12	1.459 (3)	C14—H14B	0.9700
C11—C10	1.466 (3)	C15—H15A	0.9700
C4—C3	1.366 (3)	C15—H15B	0.9700
C4—C5	1.376 (3)	C1—H1A	0.9600
C5—C6	1.371 (4)	C1—H1B	0.9600
C5—H5	0.9300	C1—H1C	0.9600
C13—S2—C15	95.41 (12)	O1—C10—C9	122.5 (2)
C13—S1—C14	96.14 (12)	O1—C10—C11	121.6 (2)
C8—N1—C12	121.5 (2)	C9—C10—C11	116.0 (2)
C8—N1—C4	119.61 (19)	C9—C8—N1	123.4 (2)
C12—N1—C4	118.88 (19)	C9—C8—H8	118.3
C7—O3—C1	117.8 (2)	N1—C8—H8	118.3
C11—C13—S1	121.55 (18)	C8—C9—C10	121.5 (2)
C11—C13—S2	123.24 (18)	C8—C9—H9	119.3
S1—C13—S2	115.21 (13)	C10—C9—H9	119.3
C13—C11—C12	118.8 (2)	C7—C2—C3	120.0 (2)
C13—C11—C10	120.5 (2)	C7—C2—H2	120.0
C12—C11—C10	120.8 (2)	C3—C2—H2	120.0
C3—C4—C5	120.0 (2)	C15—C14—S1	110.6 (2)
C3—C4—N1	119.8 (2)	C15—C14—H14A	109.5
C5—C4—N1	120.3 (2)	S1—C14—H14A	109.5
O2—C12—N1	119.6 (2)	C15—C14—H14B	109.5
O2—C12—C11	123.5 (2)	S1—C14—H14B	109.5
N1—C12—C11	116.9 (2)	H14A—C14—H14B	108.1
C6—C5—C4	119.6 (2)	C14—C15—S2	111.8 (2)
C6—C5—H5	120.2	C14—C15—H15A	109.3
C4—C5—H5	120.2	S2—C15—H15A	109.3
C5—C6—C7	120.6 (2)	C14—C15—H15B	109.3
C5—C6—H6	119.7	S2—C15—H15B	109.3
C7—C6—H6	119.7	H15A—C15—H15B	107.9
C4—C3—C2	120.6 (2)	O3—C1—H1A	109.5
C4—C3—H3	119.7	O3—C1—H1B	109.5
C2—C3—H3	119.7	H1A—C1—H1B	109.5
C2—C7—O3	125.1 (3)	O3—C1—H1C	109.5
C2—C7—C6	119.2 (2)	H1A—C1—H1C	109.5
O3—C7—C6	115.8 (2)	H1B—C1—H1C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.42	3.259 (3)	150
C14—H14a···O1ii	0.97	2.685	3.475 (4)	139
C14—H14b···O1iii	0.97	2.709	3.513 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.42	3.259 (3)	150

Symmetry code: (i) .