1-Benzoyl-3-[4-(3-benzoyl-thio-ureido)phen-yl]thio-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 mol-ecule adopts a syn-anti configuration with respect to the positions of the carbonyl groups and terminal phenyl rings relative to the thione S atom across the C-N bond. There are two intra-molecular N-H⋯O and C-H⋯S hydrogen bonds within each molecule, resulting in the formation of four six-membered S(6) rings. The central and terminal rings make a dihedral angle of 13.55 (15)°. In the crystal, mol-ecules are linked by inter-molecular C-H⋯S hydrogen bonds, forming R(2) (2)(14) rings and resulting in zigzag chains.

Related literature

For related compounds and structural parameters, see: Hung et al. (2010 ▶), Thiam et al. (2008 ▶); Arslan et al. (2004 ▶); Yamin et al., (2003 ▶). For bond-length data, see: Allen et al. (197) ▶. For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H18N4O2S2

M = 434.52

Monoclinic,

a = 11.513 (4) Å

b = 4.5279 (16) Å

c = 20.209 (7) Å

β = 101.146 (7)°

V = 1033.6 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.50 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.950, T max = 0.964

6173 measured reflections

2142 independent reflections

1529 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.171

S = 1.14

2142 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.23 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004599X/dn2618sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004599X/dn2618Isup2.hkl

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

C22H18N4O2S2	F(000) = 452
Mr = 434.52	Dx = 1.396 Mg m−3
Monoclinic, P21/n	Melting point: 511 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.513 (4) Å	Cell parameters from 1244 reflections
b = 4.5279 (16) Å	θ = 1.9–26.5°
c = 20.209 (7) Å	µ = 0.28 mm−1
β = 101.146 (7)°	T = 298 K
V = 1033.6 (6) Å3	Needle, yellow
Z = 2	0.50 × 0.15 × 0.13 mm

Bruker SMART APEX CCD area-detector diffractometer	2142 independent reflections
Radiation source: fine-focus sealed tube	1529 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scan	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→14
Tmin = 0.950, Tmax = 0.964	k = −5→5
6173 measured reflections	l = −25→23

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0839P)2 + 0.1163P] where P = (Fo2 + 2Fc2)/3
2142 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.34 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
S1	0.16597 (7)	0.6404 (2)	1.04023 (4)	0.0663 (4)
O1	0.25185 (19)	0.2798 (6)	0.84661 (10)	0.0637 (7)
N1	0.14062 (19)	0.3425 (5)	0.92651 (10)	0.0425 (6)
H1A	0.0767	0.2852	0.9388	0.051*
N2	0.30760 (19)	0.6294 (5)	0.94925 (11)	0.0432 (6)
H2A	0.3149	0.5546	0.9112	0.052*
C1	0.0805 (3)	−0.0367 (8)	0.76267 (15)	0.0643 (10)
H1	0.1454	0.0344	0.7464	0.077*
C2	−0.0026 (4)	−0.2077 (10)	0.72171 (17)	0.0836 (13)
H2	0.0062	−0.2506	0.6779	0.100*
C3	−0.0988 (3)	−0.3159 (8)	0.74552 (18)	0.0709 (11)
H3	−0.1557	−0.4286	0.7176	0.085*
C4	−0.1102 (3)	−0.2566 (8)	0.81058 (16)	0.0563 (8)
H4	−0.1742	−0.3323	0.8270	0.068*
C5	−0.0271 (3)	−0.0849 (7)	0.85172 (14)	0.0465 (7)
H5	−0.0352	−0.0467	0.8958	0.056*
C6	0.0684 (2)	0.0310 (6)	0.82792 (13)	0.0422 (7)
C7	0.1604 (2)	0.2252 (7)	0.86697 (13)	0.0425 (7)
C8	0.2103 (2)	0.5429 (6)	0.97010 (13)	0.0407 (7)
C9	0.4014 (2)	0.8203 (6)	0.97749 (12)	0.0386 (7)
C10	0.4932 (2)	0.8417 (7)	0.94239 (13)	0.0478 (8)
H10	0.4887	0.7333	0.9029	0.057*
C11	0.4091 (2)	0.9828 (7)	1.03623 (13)	0.0472 (8)
H11	0.3490	0.9734	1.0610	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.0557 (5)	0.0955 (8)	0.0554 (5)	−0.0286 (5)	0.0299 (4)	−0.0292 (5)
O1	0.0538 (13)	0.0916 (19)	0.0525 (12)	−0.0245 (12)	0.0274 (10)	−0.0201 (12)
N1	0.0372 (12)	0.0525 (16)	0.0409 (12)	−0.0114 (11)	0.0155 (10)	−0.0048 (11)
N2	0.0427 (13)	0.0514 (15)	0.0378 (12)	−0.0114 (11)	0.0136 (10)	−0.0052 (10)
C1	0.068 (2)	0.081 (3)	0.0476 (18)	−0.0252 (19)	0.0218 (15)	−0.0127 (17)
C2	0.104 (3)	0.103 (3)	0.0458 (19)	−0.041 (3)	0.0214 (19)	−0.025 (2)
C3	0.071 (2)	0.074 (3)	0.064 (2)	−0.024 (2)	0.0035 (18)	−0.0142 (19)
C4	0.0462 (18)	0.060 (2)	0.064 (2)	−0.0110 (15)	0.0133 (15)	−0.0022 (17)
C5	0.0475 (16)	0.0525 (19)	0.0415 (14)	−0.0021 (14)	0.0131 (12)	−0.0058 (13)
C6	0.0457 (16)	0.0428 (17)	0.0390 (14)	−0.0002 (13)	0.0103 (12)	−0.0013 (13)
C7	0.0452 (16)	0.0465 (18)	0.0373 (15)	−0.0027 (13)	0.0120 (12)	0.0019 (12)
C8	0.0399 (15)	0.0432 (17)	0.0401 (14)	−0.0026 (13)	0.0103 (11)	0.0044 (12)
C9	0.0399 (15)	0.0430 (17)	0.0333 (13)	−0.0032 (12)	0.0078 (11)	0.0037 (12)
C10	0.0487 (17)	0.058 (2)	0.0397 (15)	−0.0101 (14)	0.0149 (13)	−0.0109 (14)
C11	0.0425 (16)	0.060 (2)	0.0433 (15)	−0.0087 (14)	0.0188 (12)	−0.0040 (14)

S1—C8	1.656 (3)	C3—C4	1.373 (5)
O1—C7	1.227 (3)	C3—H3	0.9300
N1—C7	1.374 (3)	C4—C5	1.380 (4)
N1—C8	1.403 (3)	C4—H4	0.9300
N1—H1A	0.8600	C5—C6	1.386 (4)
N2—C8	1.330 (3)	C5—H5	0.9300
N2—C9	1.415 (3)	C6—C7	1.481 (4)
N2—H2A	0.8600	C9—C11	1.385 (4)
C1—C2	1.376 (5)	C9—C10	1.385 (4)
C1—C6	1.386 (4)	C10—C11i	1.376 (4)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.381 (5)	C11—C10i	1.376 (4)
C2—H2	0.9300	C11—H11	0.9300
C7—N1—C8	128.9 (2)	C6—C5—H5	119.7
C7—N1—H1A	115.5	C5—C6—C1	118.6 (3)
C8—N1—H1A	115.5	C5—C6—C7	125.0 (2)
C8—N2—C9	132.6 (2)	C1—C6—C7	116.5 (3)
C8—N2—H2A	113.7	O1—C7—N1	120.9 (3)
C9—N2—H2A	113.7	O1—C7—C6	120.8 (2)
C2—C1—C6	120.8 (3)	N1—C7—C6	118.3 (2)
C2—C1—H1	119.6	N2—C8—N1	113.9 (2)
C6—C1—H1	119.6	N2—C8—S1	127.6 (2)
C1—C2—C3	120.1 (3)	N1—C8—S1	118.45 (19)
C1—C2—H2	120.0	C11—C9—C10	118.2 (2)
C3—C2—H2	120.0	C11—C9—N2	126.0 (2)
C4—C3—C2	119.7 (3)	C10—C9—N2	115.8 (2)
C4—C3—H3	120.1	C11i—C10—C9	122.5 (3)
C2—C3—H3	120.1	C11i—C10—H10	118.8
C3—C4—C5	120.2 (3)	C9—C10—H10	118.8
C3—C4—H4	119.9	C10i—C11—C9	119.3 (2)
C5—C4—H4	119.9	C10i—C11—H11	120.4
C4—C5—C6	120.6 (3)	C9—C11—H11	120.4
C4—C5—H5	119.7
C6—C1—C2—C3	−0.4 (7)	C5—C6—C7—N1	−11.9 (4)
C1—C2—C3—C4	−1.2 (7)	C1—C6—C7—N1	168.0 (3)
C2—C3—C4—C5	1.2 (6)	C9—N2—C8—N1	−178.7 (3)
C3—C4—C5—C6	0.4 (5)	C9—N2—C8—S1	0.3 (5)
C4—C5—C6—C1	−1.9 (5)	C7—N1—C8—N2	0.7 (4)
C4—C5—C6—C7	177.9 (3)	C7—N1—C8—S1	−178.4 (2)
C2—C1—C6—C5	2.0 (5)	C8—N2—C9—C11	−3.8 (5)
C2—C1—C6—C7	−177.9 (3)	C8—N2—C9—C10	175.8 (3)
C8—N1—C7—O1	3.9 (5)	C11—C9—C10—C11i	0.0 (5)
C8—N1—C7—C6	−176.1 (3)	N2—C9—C10—C11i	−179.6 (3)
C5—C6—C7—O1	168.1 (3)	C10—C9—C11—C10i	0.0 (5)
C1—C6—C7—O1	−12.0 (5)	N2—C9—C11—C10i	179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.85	2.590 (3)	144
C11—H11···S1	0.93	2.56	3.215 (3)	128
C5—H5···S1ii	0.93	2.84	3.567 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.85	2.590 (3)	144
C11—H11⋯S1	0.93	2.56	3.215 (3)	128
C5—H5⋯S1i	0.93	2.84	3.567 (3)	136

Symmetry code: (i) .