2,9-Bis(5-sulfanylidene-4,5-di­hydro-1,3,4-oxa­diazol-2-yl)-1,10-phenanthroline dimethyl sulfoxide disolvate

Rahman, M.A.; Karim, M.; Arifuzzaman, M.; Siddiquee, T.; Daniels, L.M.

doi:10.1107/S1600536814003304

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o321-o322

doi:10.1107/S1600536814003304

Open

access

2,9-Bis(5-sulfanylidene-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1,10-phenanthroline dimethyl sulfoxide disolvate

Md. A Rahman,^a Mohammad Karim,^a Md. Arifuzzaman,^b Tasneem Siddiquee ^a ^* and Lee M. Daniels ^c

^aDepartment of Chemistry, Boswell Science Complex, Tennessee State University, Nashville, 3500 John A. Merritt Blvd, Nashville, TN 37209, USA, ^bDepartment of Chemistry, Iowa State University, Ames, IA 50011-3111, USA, and ^cAgilent Technologies, 5301 Stevens Creek Blvd, Santa Clara, CA 95051, USA
^*Correspondence e-mail: tsiddiqu@tnstate.edu

(Received 29 January 2014; accepted 13 February 2014; online 22 February 2014)

In the title compound, C₁₆H₈N₆O₂S₂·2C₂H₆OS, the phenanthroline molecule resides on a twofold axis, and the asymmetric unit also contains a slightly disordered [occupancy ratio for S atom of 0.95 (3):0.047 (3)] molecule of dimethyl sulfoxide. The O atoms of the solvent molecule accept hydrogen bonds from the N—H groups of the five-membered 2,3-dihydro-1,3,4-oxadiazole-2-thione ring. This ring is nearly coplanar with the phenanthroline ring, with a dihedral angle between their least-squares planes of 8.86 (6)°. In the crystal, the molecules are linked by C—H⋯O interactions.

CCDC reference: 950902

Related literature

For the biological activity of the oxadiazole unit, see: Chen et al. (2000 ); Sun et al. (2013 ); El-Emam et al. (2004 ). For their anticancer activity, see: Zhang et al. (2011 ); Gudipati et al. (2011 ); Abou-Seri (2010 ). For related structures, see: Saeed et al. (2010 ); Fun et al. (2011 ); El-Emam et al. (2012 , 2013 ).

Experimental

Crystal data

C₁₆H₈N₆O₂S₂·2C₂H₆OS
M_r = 536.66
Monoclinic, C 2/c
a = 14.113 (11) Å
b = 11.161 (8) Å
c = 16.708 (12) Å
β = 112.837 (14)°
V = 2425 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 277 K
0.42 × 0.26 × 0.15 mm

Data collection

Rigaku XtaLAB mini diffractometer
Absorption correction: multi-scan (CrystalClear; Pflugrath, 1999 ) T_min = 0.840, T_max = 0.938
5592 measured reflections
2741 independent reflections
1691 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.171
S = 1.03
2741 reflections
164 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.89 (4)	1.73 (4)	2.617 (4)	172 (4)
C9—H9C⋯O1ⁱ	0.96	2.62	3.399 (7)	138
C10—H10B⋯O2ⁱⁱ	0.96	2.57	3.317 (6)	135
N2—H2⋯S2B	0.89 (4)	2.36 (5)	3.10 (3)	140 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Pflugrath, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; 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, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 950902

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814003304/fj2661sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003304/fj2661Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003304/fj2661Isup3.cml

checkCIF report

Comment top

Compounds containing the oxadiazol moieties are known for their antimicrobial and anticancer activities. The title compound was prepared and characterized with the aim of synthesizing a series of compounds that are potentially active. These compounds were synthesized by a new process.

The title compound crystallized as a dimethyl sulfoxide (DMSO) solvate. The O atoms of the solvent form strong hydrogen bonds with the N—H centers of the diazole moiety.

The molecules are essentially planar, although the plane of the oxadiazolic five membered thionyl groups are slightly rotated from the phenanthrolene plane (the two least-squares planes form an angle of 8.86 (5)°). The molecules are arranged in planar sheets, with each pair of thiol S atoms pointing at the two apical hydrogen atoms on the adjacent phenanthroline groups.

Related literature top

For the biological activity of oxadiazols [OK?], see: Chen et al. (2000); Sun et al. (2013); El-Emam et al. (2004). For their anticancer activity, see: Zhang et al. (2011); Gudipati et al. (2011); Abou-Seri (2010). For related structures, see: Saeed et al. (2010); Fun et al. (2011); El-Emam et al. (2012, 2013). [Scheme should show the solvent molecules]

Experimental top

1,10-Phenanthroline-2,9-Di-S-methylhydrazinecarbodithioate (0.100 g, 0.21 mmol) was dissolved in THF (30 mL) with heat until a clear solution was formed. Then a solution of ZnCl₂ (0.015 g, 0.11 mmol) in THF (5 mL) was added drop-wise to the carbodithioate solution. The resulting mixture was refluxed for 2–4 hrs. After completion of the reaction, as indicated by TLC, the reaction mixture was allowed to cool to room temperature. The solvent was evaporated under reduced pressure. The product was washed with ether and dried under vacuum. Recrystallization from DMSO yielded white crystals suitable for diffraction (0.076 g, 95%Y). ¹HNMR (DMSO-d6, p.p.m.): δH 8.8 (d, 2H), 8.4(d, 2H), 8.2 (s, 2H). ¹³CNMR (DMSO-d6, p.p.m.): δC 178, 159, 144, 141, 138, 130, 128, 122. IR ν (cm^-1): 3230 (N—H), 1196 (C—O), 3100–3000(C—H), 1600–1500 (aromatic C=C), 1373 (C=S).

Computing details top

Data collection: CrystalClear (Pflugrath, 1999); cell refinement: CrystalClear (Pflugrath, 1999); data reduction: CrystalClear (Pflugrath, 1999); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure showing 50% probability displacement ellipsoids. DMSO molecules are not shown
	Fig. 2. Hydrogen bonding interaction with a DMSO solvent molecule
	Fig. 3. Packing diagram viewed along the normal to (101). Note the solvent molecules are positioned between two compounds making hydrogen bonding feasible

2,9-Bis(4,5-dihydro-1,3,4-oxadiazol-2-yl)-1,10-phenanthroline dimethyl sulfoxide disolvate top

Crystal data top

C₁₆H₈N₆O₂S₂·2C₂H₆OS	F(000) = 1112
M_r = 536.66	D_x = 1.47 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 2562 reflections
a = 14.113 (11) Å	θ = 3–27.7°
b = 11.161 (8) Å	µ = 0.43 mm⁻¹
c = 16.708 (12) Å	T = 277 K
β = 112.837 (14)°	Prism, white
V = 2425 (3) Å³	0.42 × 0.26 × 0.15 mm
Z = 4

Data collection top

Rigaku XtaLAB mini diffractometer	1691 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
profile data from ω–scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (CrystalClear; Pflugrath, 1999)	h = −18→16
T_min = 0.840, T_max = 0.938	k = −10→14
5592 measured reflections	l = −21→17
2741 independent reflections

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0524P)² + 6.1166P] where P = (F_o² + 2F_c²)/3
2741 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₈N₆O₂S₂·2C₂H₆OS	V = 2425 (3) Å³
M_r = 536.66	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.113 (11) Å	µ = 0.43 mm⁻¹
b = 11.161 (8) Å	T = 277 K
c = 16.708 (12) Å	0.42 × 0.26 × 0.15 mm
β = 112.837 (14)°

Data collection top

Rigaku XtaLAB mini diffractometer	2741 independent reflections
Absorption correction: multi-scan (CrystalClear; Pflugrath, 1999)	1691 reflections with I > 2σ(I)
T_min = 0.840, T_max = 0.938	R_int = 0.039
5592 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
2741 reflections	Δρ_min = −0.59 e Å⁻³
164 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
S2	0.26830 (13)	1.33767 (13)	0.77108 (7)	0.0922 (6)	0.953 (3)
S2B	0.265 (2)	1.355 (3)	0.695 (2)	0.092*	0.047 (3)
O2	0.1971 (2)	1.2428 (2)	0.72136 (16)	0.0647 (8)
C9	0.3844 (4)	1.3093 (7)	0.7638 (4)	0.140 (3)
H9A	0.4190	1.2459	0.8031	0.211*
H9B	0.4260	1.3803	0.7787	0.211*
H9C	0.3730	1.2858	0.7055	0.211*
C10	0.2382 (6)	1.4660 (5)	0.7056 (4)	0.130 (2)
H10A	0.2309	1.4449	0.6478	0.195*
H10B	0.2922	1.5238	0.7291	0.195*
H10C	0.1748	1.4994	0.7041	0.195*
S1	0.10833 (14)	1.36039 (10)	0.46674 (8)	0.1039 (6)
O1	0.0925 (2)	1.1303 (2)	0.42720 (15)	0.0574 (7)
N2	0.1421 (3)	1.1611 (3)	0.56291 (19)	0.0557 (8)
N1	0.1384 (2)	1.0401 (2)	0.55250 (17)	0.0506 (7)
N3	0.0448 (2)	0.9170 (2)	0.33922 (16)	0.0397 (6)
C1	0.1091 (3)	1.0258 (3)	0.4711 (2)	0.0444 (8)
C6	0.0494 (3)	0.7019 (3)	0.3399 (2)	0.0520 (9)
C4	0.1181 (3)	0.8082 (3)	0.4726 (2)	0.0548 (9)
H4	0.1506	0.8106	0.5328	0.066*
C7	0.0238 (4)	0.5931 (3)	0.2927 (2)	0.0690 (12)
H7	0.0409	0.5206	0.3223	0.083*
C5	0.0973 (3)	0.7028 (3)	0.4299 (2)	0.0614 (11)
H5	0.1148	0.6311	0.4606	0.074*
C2	0.1163 (3)	1.2176 (3)	0.4891 (2)	0.0598 (10)
C8	0.0250 (3)	0.8122 (3)	0.2969 (2)	0.0425 (7)
C3	0.0899 (3)	0.9131 (3)	0.4245 (2)	0.0439 (8)
H2	0.164 (3)	1.195 (3)	0.616 (3)	0.062 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.1324 (13)	0.1011 (10)	0.0456 (6)	−0.0709 (9)	0.0373 (7)	−0.0308 (6)
O2	0.0782 (19)	0.0651 (16)	0.0492 (14)	−0.0269 (14)	0.0228 (13)	−0.0169 (12)
C9	0.090 (4)	0.188 (7)	0.113 (5)	−0.065 (5)	0.007 (4)	0.027 (5)
C10	0.185 (7)	0.066 (3)	0.157 (6)	−0.052 (4)	0.085 (5)	−0.023 (4)
S1	0.1906 (17)	0.0392 (6)	0.0635 (7)	−0.0070 (7)	0.0292 (9)	0.0048 (5)
O1	0.0884 (19)	0.0388 (13)	0.0382 (13)	−0.0047 (12)	0.0170 (13)	0.0007 (10)
N2	0.081 (2)	0.0418 (16)	0.0369 (16)	−0.0088 (15)	0.0144 (15)	−0.0045 (13)
N1	0.069 (2)	0.0379 (14)	0.0381 (15)	−0.0046 (14)	0.0135 (14)	0.0010 (11)
N3	0.0452 (16)	0.0351 (14)	0.0379 (14)	0.0002 (11)	0.0151 (12)	0.0014 (10)
C1	0.052 (2)	0.0377 (17)	0.0382 (18)	−0.0035 (15)	0.0123 (15)	0.0050 (13)
C6	0.069 (2)	0.0350 (17)	0.0465 (19)	0.0037 (16)	0.0168 (17)	0.0037 (14)
C4	0.069 (3)	0.050 (2)	0.0354 (18)	0.0045 (18)	0.0087 (17)	0.0039 (15)
C7	0.109 (4)	0.0306 (17)	0.058 (2)	0.004 (2)	0.022 (2)	0.0056 (15)
C5	0.088 (3)	0.0379 (19)	0.047 (2)	0.0087 (19)	0.014 (2)	0.0112 (15)
C2	0.085 (3)	0.044 (2)	0.044 (2)	−0.0051 (19)	0.0176 (19)	−0.0021 (15)
C8	0.051 (2)	0.0338 (16)	0.0416 (17)	0.0002 (14)	0.0163 (15)	0.0008 (13)
C3	0.053 (2)	0.0374 (17)	0.0399 (17)	−0.0011 (15)	0.0162 (16)	0.0014 (13)

Geometric parameters (Å, º) top

S2—O2	1.474 (3)	N1—C1	1.269 (4)
S2—C9	1.719 (7)	N3—C3	1.317 (4)
S2—C10	1.751 (6)	N3—C8	1.338 (4)
C9—H9A	0.9600	C1—C3	1.449 (4)
C9—H9B	0.9600	C6—C5	1.389 (5)
C9—H9C	0.9600	C6—C8	1.400 (4)
C10—H10A	0.9600	C6—C7	1.416 (5)
C10—H10B	0.9600	C4—C5	1.348 (5)
C10—H10C	0.9600	C4—C3	1.387 (5)
S1—C2	1.631 (4)	C4—H4	0.9300
O1—C1	1.348 (4)	C7—C7ⁱ	1.321 (8)
O1—C2	1.365 (4)	C7—H7	0.9300
N2—C2	1.305 (5)	C5—H5	0.9300
N2—N1	1.360 (4)	C8—C8ⁱ	1.448 (6)
N2—H2	0.89 (4)

O2—S2—C9	106.7 (3)	O1—C1—C3	120.2 (3)
O2—S2—C10	106.7 (3)	C5—C6—C8	118.0 (3)
C9—S2—C10	96.5 (3)	C5—C6—C7	121.4 (3)
S2—C9—H9A	109.5	C8—C6—C7	120.6 (3)
S2—C9—H9B	109.5	C5—C4—C3	118.4 (3)
H9A—C9—H9B	109.5	C5—C4—H4	120.8
S2—C9—H9C	109.5	C3—C4—H4	120.8
H9A—C9—H9C	109.5	C7ⁱ—C7—C6	121.0 (2)
H9B—C9—H9C	109.5	C7ⁱ—C7—H7	119.5
S2—C10—H10A	109.5	C6—C7—H7	119.5
S2—C10—H10B	109.5	C4—C5—C6	119.6 (3)
H10A—C10—H10B	109.5	C4—C5—H5	120.2
S2—C10—H10C	109.5	C6—C5—H5	120.2
H10A—C10—H10C	109.5	N2—C2—O1	105.5 (3)
H10B—C10—H10C	109.5	N2—C2—S1	131.2 (3)
C1—O1—C2	105.4 (3)	O1—C2—S1	123.3 (3)
C2—N2—N1	112.1 (3)	N3—C8—C6	122.5 (3)
C2—N2—H2	126 (2)	N3—C8—C8ⁱ	119.07 (17)
N1—N2—H2	122 (2)	C6—C8—C8ⁱ	118.39 (19)
C1—N1—N2	104.0 (3)	N3—C3—C4	124.3 (3)
C3—N3—C8	117.2 (3)	N3—C3—C1	117.6 (3)
N1—C1—O1	112.9 (3)	C4—C3—C1	118.1 (3)
N1—C1—C3	126.8 (3)

C2—N2—N1—C1	−0.5 (5)	C3—N3—C8—C6	0.7 (5)
N2—N1—C1—O1	−0.5 (4)	C3—N3—C8—C8ⁱ	179.7 (4)
N2—N1—C1—C3	−178.3 (3)	C5—C6—C8—N3	−0.9 (6)
C2—O1—C1—N1	1.3 (4)	C7—C6—C8—N3	177.8 (4)
C2—O1—C1—C3	179.2 (3)	C5—C6—C8—C8ⁱ	−180.0 (4)
C5—C6—C7—C7ⁱ	178.4 (6)	C7—C6—C8—C8ⁱ	−1.3 (6)
C8—C6—C7—C7ⁱ	−0.2 (8)	C8—N3—C3—C4	0.2 (5)
C3—C4—C5—C6	0.5 (6)	C8—N3—C3—C1	−178.3 (3)
C8—C6—C5—C4	0.3 (6)	C5—C4—C3—N3	−0.8 (6)
C7—C6—C5—C4	−178.4 (4)	C5—C4—C3—C1	177.7 (4)
N1—N2—C2—O1	1.2 (5)	N1—C1—C3—N3	169.7 (4)
N1—N2—C2—S1	179.8 (4)	O1—C1—C3—N3	−7.9 (5)
C1—O1—C2—N2	−1.5 (4)	N1—C1—C3—C4	−9.0 (6)
C1—O1—C2—S1	179.8 (3)	O1—C1—C3—C4	173.4 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.89 (4)	1.73 (4)	2.617 (4)	172 (4)
C9—H9C···O1ⁱⁱ	0.96	2.62	3.399 (7)	138
C10—H10B···O2ⁱⁱⁱ	0.96	2.57	3.317 (6)	135
N2—H2···S2B	0.89 (4)	2.36 (5)	3.10 (3)	140 (3)

Symmetry codes: (ii) −x+1/2, −y+5/2, −z+1; (iii) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.89 (4)	1.73 (4)	2.617 (4)	172 (4)
C9—H9C···O1ⁱ	0.96	2.62	3.399 (7)	138.4
C10—H10B···O2ⁱⁱ	0.96	2.57	3.317 (6)	135.3
N2—H2···S2B	0.89 (4)	2.36 (5)	3.10 (3)	140 (3)

Symmetry codes: (i) −x+1/2, −y+5/2, −z+1; (ii) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

MK and TS acknowledge the US Department of Education for the purchase of a diffractometer.

References

Abou-Seri, S. M. (2010). Eur. J. Med. Chem. 45, 4113–4121. Web of Science CrossRef CAS PubMed Google Scholar
Chen, H., Li, Z. & Han, Y. (2000). J. Agric. Food Chem. 48, 5312–5316. Web of Science CrossRef PubMed CAS Google Scholar
El-Emam, A. A., Al-Deeb, O. A. & Al-Omar, M. (2004). Bioorg. Med. Chem. 12, 5107–5113. Web of Science PubMed CAS Google Scholar
El-Emam, A. A., Al-Omar, M. A., Al-Obaid, A.-R. M., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o684. CSD CrossRef IUCr Journals Google Scholar
El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gudipati, R., Anreddy, R. N. R. & Man, S. (2011). Saudi Pharm. J. 19, 153–158. Web of Science CrossRef CAS PubMed Google Scholar
Pflugrath, J. W. (1999). Acta Cryst. D55, 1718–1725. Web of Science CrossRef CAS IUCr Journals Google Scholar
Saeed, A., Akram, M., Rauf, A. & Bolte, M. (2010). Acta Cryst. E66, o1911. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, J., Zhu, H., Yang, Z. M. & Zhu, H. L. (2013). Eur. J. Med. Chem. 60, 23–28. Web of Science CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X.-M., Qiu, M., Sun, J., Zhang, Y.-B., Yang, Y.-S., Wang, X.-L., Tang, J.-F. & Zhu, H.-L. (2011). Bioorg. Med. Chem. 19, 6518–6524. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o321-o322

doi:10.1107/S1600536814003304

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

2,9-Bis(5-sulfanyl­idene-4,5-di­hydro-1,3,4-oxa­diazol-2-yl)-1,10-phenanthroline di­methyl sulfoxide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,9-Bis(5-sulfanylidene-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1,10-phenanthroline dimethyl sulfoxide disolvate