3-(1,3-Dithio­lan-2-yl­idene)-1-(4-meth­oxy­phen­yl)pyridine-2,4(1H,3H)-dione

Ma, Y.-C.; Song, J.-L.

doi:10.1107/S1600536811033009

organic compounds

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Volume 67| Part 9| September 2011| Page o2433

doi:10.1107/S1600536811033009

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3-(1,3-Dithiolan-2-ylidene)-1-(4-methoxyphenyl)pyridine-2,4(1H,3H)-dione

Yan-Chun Ma ^a ^* and Jin-Long Song ^b

^aEducational Institute of Jilin Province, Changchun 130022, People's Republic of China, and ^bJinlin Province Product Quality Supervision Test Institute, Changchun 130022, People's Republic of China
^*Correspondence e-mail: yanchunma999@163.com

(Received 11 August 2011; accepted 15 August 2011; online 27 August 2011)

In the title compound, C₁₅H₁₃NO₃S₂, the dithiolane ring adopts a twisted conformation. The molecule 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 interactions 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_r = 319.40
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 1.08
2905 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033009/ff2024sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811033009/ff2024Isup3.cml

checkCIF report

Comment top

Among the richness of heterocyclic compounds, N-substituted pyridone compounds (Zhu et al., 2006) have attracted an intense interest due to their potential for medicinal chemistry (Kim et al., 2008). Recently, a large number of N-substituted pyridone compounds have been prepared (Li et al., 2008). As a contribution to this field, the structure of the title crystal is presented here. The molecular structure of the title compound, together with the atom-numbering scheme, is illustrated in Fig.1. Selected bond lengths and angles are given in Table 1. The molecule exhibits a V-shaped conformation in the crystal with a dihedral angle of 79.05 (7)° between the benzene ring and the pyridine ring. The dithiolane ring has a twisted conformation.

Related literature top

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 top

The title compound was synthesized according to the literature (Li et al., 2008). It was dissolved in ethyl acetate at room temperature and hexane was added. The solution was kept at room temperature in a sealed flask for a few days to give single crystals suitable for single-crystal X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

3-(1,3-Dithiolan-2-ylidene)-1-(4-methoxyphenyl)pyridine- 2,4(1H,3H)-dione top

Crystal data top

C₁₅H₁₃NO₃S₂	Z = 4
M_r = 319.40	F(000) = 664
Monoclinic, P2₁/n	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2905 independent reflections
Radiation source: fine-focus sealed tube	1973 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 26.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→6
T_min = 0.892, T_max = 0.912	k = −34→33
12346 measured reflections	l = −12→12

Refinement top

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(F_o²) + (0.0581P)²] where P = (F_o² + 2F_c²)/3
2905 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₃NO₃S₂	V = 1448.0 (10) Å³
M_r = 319.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.322 (2) Å	µ = 0.38 mm⁻¹
b = 27.521 (11) Å	T = 293 K
c = 10.065 (4) Å	0.35 × 0.29 × 0.28 mm
β = 100.831 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2905 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1973 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.912	R_int = 0.053
12346 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.08	Δρ_max = 0.43 e Å⁻³
2905 reflections	Δρ_min = −0.30 e Å⁻³
190 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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	2.69	3.475 (4)	139
C14—H14b···O1ⁱⁱⁱ	0.97	2.71	3.513 (4)	141

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1, y, z; (iii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₃S₂
M_r	319.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.322 (2), 27.521 (11), 10.065 (4)
β (°)	100.831 (5)
V (Å³)	1448.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.35 × 0.29 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.892, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	12346, 2905, 1973
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.121, 1.08
No. of reflections	2905
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.30

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.93	2.422	3.259 (3)	150

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Educational Institute of Jilin Province for supporting this work.

References

Bruker (2002). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kim, K. S., Zhang, L., Schmidt, R., Cai, Z. W., Wei, D., Williams, D. K., Lombardo, L. J., Trainor, G. L., Xie, D., Zhang, Y., An, Y., Sack, J. S., Tokarski, J. S., Darienzo, C., Kamath, A., Marathe, P., Zhang, Y., Lippy, J., Jeyaseelan, R. S., Wautlet, B., Henley, B., Gullo-Brown, J., Manne, V., Hunt, J. T., Fargnoli, J. & Borzilleri, R. M. (2008). J. Med. Chem. 51, 5330–5341. CrossRef CAS Google Scholar
Li, Y.-H., Li, W.-L., Zhang, R., Zhou, Y. & Dong, D.-W. (2008). Synthesis, 21, 3411–3414. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, T., Yan, Z., Chucholowski, A., Webb, T. R. & Li, R.-S. (2006). J. Comb. Chem. 8, 401–409. CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(1,3-Di­thio­lan-2-yl­­idene)-1-(4-meth­­oxy­phen­yl)pyridine-2,4(1H,3H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(1,3-Dithiolan-2-ylidene)-1-(4-methoxyphenyl)pyridine-2,4(1H,3H)-dione