1,1'-Diphenyl-3,3'-(p-phenyl-enedicarbon-yl)dithio-urea.

The mol-ecule of the title compound, C(22)H(18)N(4)O(2)S(2), lies across a crystallographic inversion centre. The central benzene ring forms dihedral angles of 29.39 (9) and 79.11 (12)°, respectively, with the thio-urea unit and the terminal phenyl ring. Intra-molecular N-H⋯O hydrogen bonds generate two S(6) ring motifs. In the crystal, mol-ecules are linked into chains along [10] by inter-molecular N-H⋯S hydrogen bonds.

Related literature

For general background and crystal structures of thio­urea derivatives, see: Dong et al. (2006 ▶); Hassan et al. (2008 ▶); Yamin & Hassan (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H18N4O2S2

M = 434.52

Triclinic,

a = 5.769 (2) Å

b = 7.919 (3) Å

c = 11.534 (4) Å

α = 75.961 (10)°

β = 87.000 (8)°

γ = 89.861 (8)°

V = 510.5 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.29 mm−1

T = 273 K

0.23 × 0.11 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.937, T max = 0.986

5484 measured reflections

1809 independent reflections

1503 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.113

S = 1.13

1809 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055834/ci5010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055834/ci5010Isup2.hkl

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

C22H18N4O2S2	Z = 1
Mr = 434.52	F(000) = 226
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.769 (2) Å	Cell parameters from 1272 reflections
b = 7.919 (3) Å	θ = 1.8–25.0°
c = 11.534 (4) Å	µ = 0.29 mm−1
α = 75.961 (10)°	T = 273 K
β = 87.000 (8)°	Plate, yellow
γ = 89.861 (8)°	0.23 × 0.11 × 0.05 mm
V = 510.5 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	1809 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scan	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
Tmin = 0.937, Tmax = 0.986	k = −9→9
5484 measured reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.1485P] where P = (Fo2 + 2Fc2)/3
1809 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.16 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
S1	0.32753 (13)	0.52539 (9)	0.65718 (6)	0.0563 (3)
N1	0.2814 (3)	0.2027 (3)	0.79479 (17)	0.0451 (5)
H1A	0.3202	0.0953	0.8057	0.054*
N2	0.5449 (3)	0.2421 (2)	0.63257 (16)	0.0402 (5)
H2A	0.6037	0.3126	0.5690	0.048*
O1	0.5453 (3)	−0.0411 (2)	0.73721 (17)	0.0647 (6)
C1	0.1594 (5)	0.1854 (3)	1.0006 (2)	0.0506 (7)
H1B	0.2946	0.1251	1.0236	0.061*
C2	−0.0015 (5)	0.2172 (4)	1.0865 (2)	0.0580 (8)
H2B	0.0274	0.1796	1.1672	0.070*
C3	−0.2010 (5)	0.3030 (4)	1.0531 (3)	0.0570 (8)
H3A	−0.3086	0.3232	1.1111	0.068*
C4	−0.2439 (5)	0.3599 (4)	0.9342 (3)	0.0582 (8)
H4A	−0.3807	0.4184	0.9119	0.070*
C5	−0.0854 (4)	0.3310 (3)	0.8470 (2)	0.0504 (7)
H5A	−0.1148	0.3696	0.7664	0.060*
C6	0.1173 (4)	0.2439 (3)	0.8812 (2)	0.0413 (6)
C7	0.3798 (4)	0.3128 (3)	0.6997 (2)	0.0392 (6)
C8	0.6254 (4)	0.0747 (3)	0.6550 (2)	0.0416 (6)
C9	0.8197 (4)	0.0410 (3)	0.5729 (2)	0.0366 (5)
C10	0.9840 (4)	0.1665 (3)	0.5176 (2)	0.0424 (6)
H10A	0.9741	0.2781	0.5300	0.051*
C11	1.1621 (4)	0.1265 (3)	0.4442 (2)	0.0420 (6)
H11A	1.2700	0.2117	0.4063	0.063*

	U11	U22	U33	U12	U13	U23
S1	0.0734 (5)	0.0418 (4)	0.0480 (4)	0.0108 (3)	0.0225 (3)	−0.0049 (3)
N1	0.0520 (13)	0.0393 (11)	0.0402 (12)	0.0059 (9)	0.0153 (10)	−0.0063 (9)
N2	0.0425 (11)	0.0406 (11)	0.0337 (11)	0.0043 (9)	0.0123 (9)	−0.0046 (9)
O1	0.0729 (13)	0.0485 (11)	0.0597 (12)	0.0131 (9)	0.0335 (10)	0.0042 (10)
C1	0.0528 (16)	0.0529 (16)	0.0418 (15)	0.0031 (13)	0.0062 (12)	−0.0049 (12)
C2	0.0677 (19)	0.0633 (19)	0.0397 (15)	−0.0032 (15)	0.0129 (13)	−0.0097 (13)
C3	0.0584 (18)	0.0592 (18)	0.0540 (18)	−0.0055 (14)	0.0247 (14)	−0.0205 (14)
C4	0.0433 (16)	0.0655 (19)	0.067 (2)	0.0032 (13)	0.0102 (14)	−0.0221 (15)
C5	0.0451 (15)	0.0641 (18)	0.0419 (15)	0.0022 (13)	0.0032 (12)	−0.0137 (13)
C6	0.0410 (14)	0.0391 (14)	0.0430 (14)	−0.0015 (11)	0.0105 (11)	−0.0110 (11)
C7	0.0384 (13)	0.0445 (14)	0.0346 (13)	0.0039 (11)	0.0027 (10)	−0.0106 (11)
C8	0.0419 (14)	0.0419 (14)	0.0386 (14)	0.0050 (11)	0.0056 (11)	−0.0070 (12)
C9	0.0368 (13)	0.0406 (13)	0.0318 (12)	0.0052 (10)	−0.0009 (10)	−0.0079 (10)
C10	0.0437 (14)	0.0376 (14)	0.0462 (15)	0.0032 (11)	0.0040 (11)	−0.0124 (11)
C11	0.0391 (13)	0.0401 (14)	0.0439 (14)	−0.0001 (10)	0.0086 (11)	−0.0068 (11)

S1—C7	1.667 (2)	C3—C4	1.372 (4)
N1—C7	1.327 (3)	C3—H3A	0.93
N1—C6	1.433 (3)	C4—C5	1.383 (3)
N1—H1A	0.86	C4—H4A	0.93
N2—C8	1.373 (3)	C5—C6	1.383 (3)
N2—C7	1.396 (3)	C5—H5A	0.93
N2—H2A	0.86	C8—C9	1.495 (3)
O1—C8	1.220 (3)	C9—C10	1.388 (3)
C1—C6	1.376 (4)	C9—C11i	1.390 (3)
C1—C2	1.389 (4)	C10—C11	1.382 (3)
C1—H1B	0.93	C10—H10A	0.93
C2—C3	1.361 (4)	C11—C9i	1.390 (3)
C2—H2B	0.93	C11—H11A	0.93
C7—N1—C6	126.8 (2)	C4—C5—H5A	120.4
C7—N1—H1A	116.6	C1—C6—C5	120.3 (2)
C6—N1—H1A	116.6	C1—C6—N1	118.3 (2)
C8—N2—C7	128.3 (2)	C5—C6—N1	121.3 (2)
C8—N2—H2A	115.8	N1—C7—N2	115.9 (2)
C7—N2—H2A	115.8	N1—C7—S1	125.62 (18)
C6—C1—C2	119.5 (3)	N2—C7—S1	118.42 (17)
C6—C1—H1B	120.2	O1—C8—N2	122.6 (2)
C2—C1—H1B	120.2	O1—C8—C9	121.2 (2)
C3—C2—C1	120.4 (3)	N2—C8—C9	116.2 (2)
C3—C2—H2B	119.8	C10—C9—C11i	119.5 (2)
C1—C2—H2B	119.8	C10—C9—C8	123.1 (2)
C2—C3—C4	120.1 (2)	C11i—C9—C8	117.4 (2)
C2—C3—H3A	119.9	C11—C10—C9	120.3 (2)
C4—C3—H3A	119.9	C11—C10—H10A	119.8
C3—C4—C5	120.6 (3)	C9—C10—H10A	119.8
C3—C4—H4A	119.7	C10—C11—C9i	120.1 (2)
C5—C4—H4A	119.7	C10—C11—H11A	119.9
C6—C5—C4	119.2 (3)	C9i—C11—H11A	119.9
C6—C5—H5A	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.94	2.644 (3)	138
N2—H2A···S1ii	0.86	2.62	3.446 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.94	2.644 (3)	138
N2—H2A⋯S1i	0.86	2.62	3.446 (3)	160

Symmetry code: (i) .