2,9-Bis(5-sulfanylidene-4,5-di-hydro-1,3,4-oxa-diazol-2-yl)-1,10-phenanthroline dimethyl sulfoxide disolvate.

In the title compound, C16H8N6O2S2·2C2H6OS, the phenanthroline mol-ecule 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)] mol-ecule of dimethyl sulfoxide. The O atoms of the solvent mol-ecule accept hydrogen bonds from the N-H groups of the five-membered 2,3-di-hydro-1,3,4-oxa-diazole-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 mol-ecules are linked by C-H⋯O inter-actions.

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 = 536.66

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.171

S = 1.03

2741 reflections

164 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.59 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003304/fj2661sup1.cif

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

Click here for additional data file.

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

CCDC reference: 950902

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H8N6O2S2·2C2H6OS	F(000) = 1112
Mr = 536.66	Dx = 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

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

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(Fo2) + (0.0524P)2 + 6.1166P] where P = (Fo2 + 2Fc2)/3
2741 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)*

	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)

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)

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)

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) ; (ii) .