3,3'-Diphenyl-1,1'-(butane-1,4-di-yl)dithio-urea.

The asymmetric unit of the title compound, C(18)H(22)N(4)S(2), contains one half-mol-ecule, the complete mol-ecule being generated by crystallographic inversion symmetry. The crystal structure features two inter-molecular N-H⋯S hydrogen-bonding inter-actions, the first generating an infinite chain along the b axis and the second an infinite chain along the a axis, together forming an inter-locking structure.

Related literature

Thio­urea derivatives are conspicuous for their biological activity as they form strong hydrogen-bonding inter­actions and coordinate to metal ions, see: Wittkopp & Schreiner (2003 ▶); Li et al. (2008 ▶). For appliactions of thio­urea, see Abdallah et al. (2006 ▶); Karamé et al. (2003 ▶); Nan et al. (2000 ▶); Breuzard et al. (2000 ▶); Tommasino et al., (2000 ▶); Reinoso García et al. (2004 ▶); Leung et al. (2008 ▶). For synthesis of the title compound, see: Lee et al. (1985 ▶).

Experimental

Crystal data

C18H22N4S2

M = 358.52

Monoclinic,

a = 9.6795 (3) Å

b = 7.8677 (3) Å

c = 12.3213 (4) Å

β = 105.816 (2)°

V = 902.81 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 173 K

0.46 × 0.45 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

9210 measured reflections

2192 independent reflections

1710 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.06

2192 reflections

117 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2006 ▶); data reduction: SAINT-Plus; 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/S1600536811033071/om2458sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033071/om2458Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033071/om2458Isup3.cml

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

C18H22N4S2	F(000) = 380
Mr = 358.52	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3394 reflections
a = 9.6795 (3) Å	θ = 3.1–28.2°
b = 7.8677 (3) Å	µ = 0.30 mm−1
c = 12.3213 (4) Å	T = 173 K
β = 105.816 (2)°	Plate, colourless
V = 902.81 (5) Å3	0.46 × 0.45 × 0.13 mm
Z = 2

Bruker APEXII CCD diffractometer	1710 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 28.0°, θmin = 2.2°
φ and ω scans	h = −12→12
9210 measured reflections	k = −10→10
2192 independent reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.0075P] where P = (Fo2 + 2Fc2)/3
2192 reflections	(Δ/σ)max = 0.005
117 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.23 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	0.23226 (14)	−0.10682 (19)	0.10971 (12)	0.0250 (3)
C2	0.17043 (15)	−0.0394 (2)	0.19000 (13)	0.0314 (4)
H2	0.2223	0.0392	0.2445	0.038*
C3	0.03242 (16)	−0.0880 (2)	0.18976 (14)	0.0383 (4)
H3	−0.0092	−0.0449	0.2457	0.046*
C4	−0.04488 (16)	−0.1990 (2)	0.10837 (15)	0.0393 (4)
H4	−0.1387	−0.2333	0.1092	0.047*
C5	0.01453 (16)	−0.2598 (2)	0.02594 (14)	0.0366 (4)
H5	−0.0397	−0.3326	−0.0315	0.044*
C6	0.15346 (15)	−0.2145 (2)	0.02723 (12)	0.0296 (3)
H6	0.1947	−0.2578	−0.0289	0.036*
C7	0.49385 (14)	−0.05136 (17)	0.19228 (11)	0.0223 (3)
C8	0.60322 (15)	−0.0926 (2)	0.39648 (12)	0.0286 (3)
H8A	0.6645	0.0072	0.3938	0.034*
H8B	0.6631	−0.1961	0.4027	0.034*
C9	0.54395 (17)	−0.0793 (2)	0.49881 (12)	0.0316 (3)
H9A	0.4833	−0.1801	0.5004	0.038*
H9B	0.6253	−0.0821	0.5680	0.038*
N1	0.37258 (12)	−0.05795 (17)	0.10580 (10)	0.0265 (3)
N2	0.48550 (13)	−0.10013 (17)	0.29351 (10)	0.0261 (3)
S1	0.65024 (4)	0.01605 (5)	0.16882 (3)	0.02773 (13)
H1N	0.3820 (18)	−0.045 (2)	0.0393 (15)	0.036 (5)*
H2N	0.4173 (16)	−0.158 (2)	0.2950 (13)	0.028 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0203 (7)	0.0312 (8)	0.0236 (7)	0.0032 (6)	0.0058 (5)	0.0059 (6)
C2	0.0244 (7)	0.0448 (9)	0.0253 (8)	0.0052 (6)	0.0073 (6)	0.0008 (6)
C3	0.0274 (8)	0.0553 (11)	0.0354 (9)	0.0102 (7)	0.0140 (7)	0.0074 (8)
C4	0.0216 (7)	0.0464 (10)	0.0506 (10)	0.0014 (7)	0.0110 (7)	0.0127 (8)
C5	0.0254 (8)	0.0352 (9)	0.0450 (10)	−0.0020 (6)	0.0024 (7)	0.0003 (7)
C6	0.0260 (7)	0.0321 (8)	0.0301 (8)	0.0030 (6)	0.0062 (6)	0.0008 (6)
C7	0.0219 (7)	0.0238 (7)	0.0225 (7)	0.0013 (5)	0.0083 (5)	−0.0036 (5)
C8	0.0223 (7)	0.0392 (8)	0.0230 (7)	0.0017 (6)	0.0041 (6)	−0.0015 (6)
C9	0.0311 (8)	0.0392 (9)	0.0234 (7)	0.0028 (7)	0.0057 (6)	0.0023 (6)
N1	0.0221 (6)	0.0406 (7)	0.0181 (6)	−0.0017 (5)	0.0076 (5)	0.0001 (5)
N2	0.0204 (6)	0.0368 (7)	0.0215 (6)	−0.0068 (5)	0.0064 (5)	0.0008 (5)
S1	0.0215 (2)	0.0385 (2)	0.0256 (2)	−0.00221 (15)	0.01058 (15)	−0.00035 (15)

C1—C6	1.382 (2)	C7—N2	1.3283 (17)
C1—C2	1.393 (2)	C7—N1	1.3543 (18)
C1—N1	1.4250 (17)	C7—S1	1.7014 (14)
C2—C3	1.389 (2)	C8—N2	1.4572 (18)
C2—H2	0.9500	C8—C9	1.5246 (19)
C3—C4	1.385 (2)	C8—H8A	0.9900
C3—H3	0.9500	C8—H8B	0.9900
C4—C5	1.382 (2)	C9—C9i	1.516 (3)
C4—H4	0.9500	C9—H9A	0.9900
C5—C6	1.387 (2)	C9—H9B	0.9900
C5—H5	0.9500	N1—H1N	0.855 (18)
C6—H6	0.9500	N2—H2N	0.806 (15)
C6—C1—C2	119.85 (13)	N1—C7—S1	119.92 (10)
C6—C1—N1	118.73 (12)	N2—C8—C9	109.98 (11)
C2—C1—N1	121.28 (13)	N2—C8—H8A	109.7
C3—C2—C1	119.53 (15)	C9—C8—H8A	109.7
C3—C2—H2	120.2	N2—C8—H8B	109.7
C1—C2—H2	120.2	C9—C8—H8B	109.7
C4—C3—C2	120.30 (15)	H8A—C8—H8B	108.2
C4—C3—H3	119.9	C9i—C9—C8	114.35 (16)
C2—C3—H3	119.9	C9i—C9—H9A	108.7
C5—C4—C3	119.97 (14)	C8—C9—H9A	108.7
C5—C4—H4	120.0	C9i—C9—H9B	108.7
C3—C4—H4	120.0	C8—C9—H9B	108.7
C4—C5—C6	119.93 (15)	H9A—C9—H9B	107.6
C4—C5—H5	120.0	C7—N1—C1	127.84 (12)
C6—C5—H5	120.0	C7—N1—H1N	117.0 (12)
C1—C6—C5	120.33 (14)	C1—N1—H1N	114.6 (12)
C1—C6—H6	119.8	C7—N2—C8	124.94 (12)
C5—C6—H6	119.8	C7—N2—H2N	116.4 (11)
N2—C7—N1	117.79 (12)	C8—N2—H2N	117.0 (11)
N2—C7—S1	122.29 (11)
C6—C1—C2—C3	3.2 (2)	N2—C8—C9—C9i	−62.1 (2)
N1—C1—C2—C3	178.86 (14)	N2—C7—N1—C1	2.1 (2)
C1—C2—C3—C4	−1.8 (2)	S1—C7—N1—C1	−178.44 (12)
C2—C3—C4—C5	−1.0 (3)	C6—C1—N1—C7	−135.44 (15)
C3—C4—C5—C6	2.3 (3)	C2—C1—N1—C7	48.9 (2)
C2—C1—C6—C5	−1.9 (2)	N1—C7—N2—C8	−176.58 (13)
N1—C1—C6—C5	−177.63 (14)	S1—C7—N2—C8	4.0 (2)
C4—C5—C6—C1	−0.9 (2)	C9—C8—N2—C7	154.26 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ii	0.855 (18)	2.508 (18)	3.3465 (13)	167.1 (15)
N2—H2N···S1iii	0.806 (15)	2.713 (16)	3.3755 (14)	140.7 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.855 (18)	2.508 (18)	3.3465 (13)	167.1 (15)
N2—H2N⋯S1ii	0.806 (15)	2.713 (16)	3.3755 (14)	140.7 (13)

Symmetry codes: (i) ; (ii) .