1,1'-(Ethane-1,2-di-yl)bis-(3-phenyl-thio-urea).

The complete molecule of the title compound, C(16)H(18)N(4)S(2), is generated by crystallographic inversion symmetry. The dihedral angle between the phenyl ring and the thio-urea group is 52.9 (4)°. The crystal structure displays inter-molecular N-H⋯S hydrogen bonding, which generates sheets in the ab plane.

Related literature

Bisthio­urea and urea derivatives with alkane bridges can adopt two general shapes, bent (Pansuriya et al., 2011a ▶) or straight alkyl chains (Pansuriya et al., 2011b ▶; Koevoets et al., 2005 ▶). For the synthesis see: Lee et al. (1985 ▶).

Experimental

Crystal data

C16H18N4S2

M = 330.46

Orthorhombic,

a = 10.5823 (4) Å

b = 9.1053 (3) Å

c = 16.4163 (6) Å

V = 1581.79 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 173 K

0.53 × 0.26 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

22438 measured reflections

1902 independent reflections

1523 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.135

S = 1.13

1902 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039936/pk2349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039936/pk2349Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039936/pk2349Isup3.cml

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

C16H18N4S2	Dx = 1.388 Mg m−3
Mr = 330.46	Melting point: 462 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8682 reflections
a = 10.5823 (4) Å	θ = 2.5–28.3°
b = 9.1053 (3) Å	µ = 0.34 mm−1
c = 16.4163 (6) Å	T = 173 K
V = 1581.79 (10) Å3	Plate, colourless
Z = 4	0.53 × 0.26 × 0.12 mm
F(000) = 696

Bruker APEXII CCD diffractometer	1523 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
graphite	θmax = 28.0°, θmin = 2.5°
φ and ω scans	h = −13→13
22438 measured reflections	k = −12→12
1902 independent reflections	l = −21→21

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0373P)2 + 3.3624P] where P = (Fo2 + 2Fc2)/3
1902 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.38 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	0.4907 (2)	0.4345 (3)	0.35565 (15)	0.0229 (5)
C2	0.4488 (3)	0.3631 (3)	0.28604 (17)	0.0281 (6)
H2	0.4897	0.2763	0.2678	0.034*
C3	0.3463 (3)	0.4196 (3)	0.24308 (18)	0.0329 (6)
H3	0.3161	0.3700	0.1961	0.039*
C4	0.2885 (3)	0.5468 (3)	0.26835 (18)	0.0339 (6)
H4	0.2185	0.5848	0.2389	0.041*
C5	0.3321 (3)	0.6195 (3)	0.33647 (18)	0.0321 (6)
H5	0.2932	0.7086	0.3530	0.039*
C6	0.4330 (3)	0.5630 (3)	0.38118 (17)	0.0280 (6)
H6	0.4619	0.6121	0.4287	0.034*
C7	0.6127 (2)	0.2403 (3)	0.42665 (15)	0.0226 (5)
C8	0.5090 (3)	0.0019 (3)	0.45415 (16)	0.0263 (5)
H8A	0.5891	−0.0479	0.4398	0.032*
H8B	0.4389	−0.0520	0.4276	0.032*
N1	0.5975 (2)	0.3795 (2)	0.39925 (14)	0.0246 (5)
H1N	0.6591	0.4418	0.4092	0.030*
N2	0.5118 (2)	0.1523 (2)	0.42399 (14)	0.0258 (5)
H2N	0.4421	0.1877	0.4025	0.031*
S1	0.75428 (6)	0.18711 (7)	0.46353 (4)	0.0273 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0182 (11)	0.0206 (12)	0.0298 (12)	−0.0016 (9)	−0.0006 (10)	0.0067 (10)
C2	0.0263 (13)	0.0241 (13)	0.0338 (13)	0.0016 (11)	0.0008 (11)	0.0000 (11)
C3	0.0346 (15)	0.0306 (14)	0.0335 (14)	−0.0042 (12)	−0.0079 (12)	0.0026 (12)
C4	0.0268 (14)	0.0340 (15)	0.0407 (15)	−0.0005 (12)	−0.0072 (12)	0.0107 (12)
C5	0.0238 (13)	0.0281 (14)	0.0445 (16)	0.0071 (11)	0.0010 (12)	0.0039 (12)
C6	0.0265 (13)	0.0266 (13)	0.0309 (13)	0.0009 (11)	−0.0005 (10)	−0.0005 (11)
C7	0.0170 (11)	0.0230 (12)	0.0279 (12)	0.0013 (9)	0.0023 (10)	0.0006 (10)
C8	0.0229 (12)	0.0184 (11)	0.0376 (14)	−0.0016 (9)	−0.0004 (11)	0.0030 (10)
N1	0.0164 (10)	0.0196 (10)	0.0378 (12)	−0.0019 (8)	−0.0033 (9)	0.0024 (9)
N2	0.0152 (10)	0.0219 (11)	0.0403 (12)	−0.0003 (8)	−0.0024 (9)	0.0084 (9)
S1	0.0150 (3)	0.0218 (3)	0.0450 (4)	0.0017 (2)	−0.0026 (3)	0.0001 (3)

C1—C6	1.385 (4)	C6—H6	0.9500
C1—C2	1.387 (4)	C7—N2	1.336 (3)
C1—N1	1.428 (3)	C7—N1	1.354 (3)
C2—C3	1.393 (4)	C7—S1	1.687 (2)
C2—H2	0.9500	C8—N2	1.456 (3)
C3—C4	1.373 (4)	C8—C8i	1.518 (5)
C3—H3	0.9500	C8—H8A	0.9900
C4—C5	1.379 (4)	C8—H8B	0.9900
C4—H4	0.9500	N1—H1N	0.8800
C5—C6	1.394 (4)	N2—H2N	0.8800
C5—H5	0.9500
C6—C1—C2	120.3 (2)	C5—C6—H6	120.3
C6—C1—N1	119.6 (2)	N2—C7—N1	117.1 (2)
C2—C1—N1	120.1 (2)	N2—C7—S1	123.3 (2)
C1—C2—C3	119.5 (3)	N1—C7—S1	119.59 (19)
C1—C2—H2	120.2	N2—C8—C8i	111.2 (3)
C3—C2—H2	120.2	N2—C8—H8A	109.4
C4—C3—C2	120.4 (3)	C8i—C8—H8A	109.4
C4—C3—H3	119.8	N2—C8—H8B	109.4
C2—C3—H3	119.8	C8i—C8—H8B	109.4
C3—C4—C5	120.0 (3)	H8A—C8—H8B	108.0
C3—C4—H4	120.0	C7—N1—C1	126.1 (2)
C5—C4—H4	120.0	C7—N1—H1N	117.0
C4—C5—C6	120.4 (3)	C1—N1—H1N	117.0
C4—C5—H5	119.8	C7—N2—C8	124.7 (2)
C6—C5—H5	119.8	C7—N2—H2N	117.6
C1—C6—C5	119.4 (3)	C8—N2—H2N	117.6
C1—C6—H6	120.3
C6—C1—C2—C3	−1.5 (4)	N2—C7—N1—C1	−11.0 (4)
N1—C1—C2—C3	−178.6 (2)	S1—C7—N1—C1	170.1 (2)
C1—C2—C3—C4	1.3 (4)	C6—C1—N1—C7	130.0 (3)
C2—C3—C4—C5	0.1 (4)	C2—C1—N1—C7	−52.9 (4)
C3—C4—C5—C6	−1.4 (4)	N1—C7—N2—C8	−177.1 (2)
C2—C1—C6—C5	0.3 (4)	S1—C7—N2—C8	1.8 (4)
N1—C1—C6—C5	177.4 (2)	C8i—C8—N2—C7	80.6 (4)
C4—C5—C6—C1	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ii	0.88	2.57	3.379 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.88	2.57	3.379 (2)	153

Symmetry code: (i) .