3,3'-Dibenzoyl-1,1'-(butane-1,4-diyl)-dithio-urea.

In the centrosymmetric title compound, C(20)H(22)N(4)O(2)S(2), the carbonyl group forms an intra-molecular hydrogen bond with the NH group attached to the butanediyl linker, resulting in a six-membered ring. There are also inter-molecular C-H⋯S inter-actions in the crystal structure, and π-π inter-actions between phenyl groups [2.425 (3) Å].

Related literature

For related literature, see: Breuzard et al. (2000 ▶); Burrows et al. (1997 ▶); Dong et al. (2006 ▶); Foss et al. (2004 ▶); Huang et al., 2006 ▶; Nan et al. (2000 ▶); Teoh et al. (1999 ▶); Valdés-Martínez et al. (2004 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C20H22N4O2S2

M = 414.54

Monoclinic,

a = 6.0405 (11) Å

b = 23.358 (2) Å

c = 7.2877 (13) Å

β = 104.018 (2)°

V = 997.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 298 (2) K

0.22 × 0.16 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.939, T max = 0.980

4845 measured reflections

1735 independent reflections

1044 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.106

S = 1.02

1735 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Version 5.1; Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004340/hg2377sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004340/hg2377Isup2.hkl

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

C20H22N4O2S2	F000 = 436
Mr = 414.54	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Melting point = 469–471 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 6.0405 (11) Å	Cell parameters from 1545 reflections
b = 23.358 (2) Å	θ = 2.9–27.5º
c = 7.2877 (13) Å	µ = 0.29 mm−1
β = 104.018 (2)º	T = 298 (2) K
V = 997.6 (3) Å3	Block, colourless
Z = 2	0.22 × 0.16 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	1735 independent reflections
Radiation source: fine-focus sealed tube	1044 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.058
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.939, Tmax = 0.980	k = −27→21
4845 measured reflections	l = −8→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.093P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1735 reflections	Δρmax = 0.23 e Å−3
127 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.6333 (4)	0.33193 (10)	0.2464 (3)	0.0436 (7)
H1	0.4996	0.3174	0.2342	0.052*
N2	0.8393 (4)	0.41571 (9)	0.2530 (3)	0.0378 (6)
H2	0.9588	0.3944	0.2747	0.045*
O1	1.0080 (4)	0.30751 (8)	0.3060 (3)	0.0556 (7)
S1	0.39076 (13)	0.42652 (4)	0.19513 (14)	0.0579 (3)
C1	0.6387 (5)	0.39150 (12)	0.2345 (4)	0.0367 (7)
C2	0.8669 (5)	0.47772 (12)	0.2383 (4)	0.0403 (8)
H2A	0.7351	0.4931	0.1482	0.048*
H2B	1.0004	0.4853	0.1902	0.048*
C3	0.8930 (4)	0.50817 (12)	0.4263 (4)	0.0415 (8)
H3A	0.8946	0.5491	0.4051	0.050*
H3B	0.7612	0.4996	0.4755	0.050*
C4	0.8082 (5)	0.29268 (13)	0.2746 (4)	0.0395 (8)
C5	0.7380 (5)	0.23119 (12)	0.2626 (4)	0.0383 (8)
C6	0.5157 (6)	0.21226 (13)	0.1896 (5)	0.0530 (9)
H6	0.3997	0.2387	0.1462	0.064*
C7	0.4663 (6)	0.15458 (15)	0.1811 (5)	0.0617 (10)
H7	0.3171	0.1425	0.1316	0.074*
C8	0.6341 (6)	0.11496 (14)	0.2445 (5)	0.0557 (10)
H8	0.5993	0.0761	0.2394	0.067*
C9	0.8531 (6)	0.13299 (14)	0.3154 (5)	0.0555 (9)
H9	0.9681	0.1062	0.3581	0.067*
C10	0.9057 (5)	0.19086 (13)	0.3241 (4)	0.0462 (9)
H10	1.0558	0.2026	0.3720	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.0352 (14)	0.0346 (15)	0.060 (2)	−0.0048 (12)	0.0101 (13)	−0.0022 (13)
N2	0.0309 (14)	0.0340 (14)	0.0476 (17)	0.0051 (11)	0.0077 (12)	−0.0024 (12)
O1	0.0374 (13)	0.0408 (13)	0.0810 (18)	−0.0008 (10)	−0.0005 (12)	0.0001 (12)
S1	0.0363 (5)	0.0507 (5)	0.0883 (8)	0.0062 (4)	0.0181 (5)	0.0070 (5)
C1	0.0325 (17)	0.0413 (18)	0.036 (2)	0.0030 (14)	0.0078 (14)	0.0004 (15)
C2	0.0375 (17)	0.0373 (18)	0.047 (2)	0.0039 (14)	0.0125 (15)	0.0036 (16)
C3	0.0386 (17)	0.0299 (17)	0.055 (2)	0.0042 (13)	0.0102 (16)	0.0017 (16)
C4	0.043 (2)	0.0399 (19)	0.033 (2)	0.0048 (15)	0.0035 (16)	−0.0001 (15)
C5	0.0455 (19)	0.0358 (18)	0.034 (2)	0.0012 (15)	0.0108 (16)	−0.0009 (15)
C6	0.047 (2)	0.042 (2)	0.065 (3)	0.0019 (16)	0.0047 (18)	0.0009 (19)
C7	0.056 (2)	0.049 (2)	0.075 (3)	−0.0142 (18)	0.007 (2)	−0.005 (2)
C8	0.074 (3)	0.039 (2)	0.057 (3)	−0.0035 (19)	0.021 (2)	0.0001 (18)
C9	0.071 (3)	0.043 (2)	0.054 (3)	0.0150 (19)	0.018 (2)	0.0049 (18)
C10	0.044 (2)	0.044 (2)	0.048 (2)	0.0045 (16)	0.0070 (17)	−0.0015 (17)

N1—C4	1.376 (3)	C3—H3B	0.9700
N1—C1	1.395 (3)	C4—C5	1.494 (4)
N1—H1	0.8600	C5—C10	1.376 (4)
N2—C1	1.314 (3)	C5—C6	1.391 (4)
N2—C2	1.465 (3)	C6—C7	1.378 (4)
N2—H2	0.8600	C6—H6	0.9300
O1—C4	1.223 (3)	C7—C8	1.368 (4)
S1—C1	1.669 (3)	C7—H7	0.9300
C2—C3	1.518 (4)	C8—C9	1.365 (4)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.387 (4)
C3—C3i	1.516 (5)	C9—H9	0.9300
C3—H3A	0.9700	C10—H10	0.9300
C4—N1—C1	130.2 (2)	O1—C4—N1	121.8 (3)
C4—N1—H1	114.9	O1—C4—C5	122.4 (3)
C1—N1—H1	114.9	N1—C4—C5	115.8 (3)
C1—N2—C2	122.4 (2)	C10—C5—C6	118.2 (3)
C1—N2—H2	118.8	C10—C5—C4	117.6 (3)
C2—N2—H2	118.8	C6—C5—C4	124.2 (3)
N2—C1—N1	117.2 (2)	C7—C6—C5	120.4 (3)
N2—C1—S1	125.0 (2)	C7—C6—H6	119.8
N1—C1—S1	117.8 (2)	C5—C6—H6	119.8
N2—C2—C3	112.7 (2)	C8—C7—C6	120.8 (3)
N2—C2—H2A	109.1	C8—C7—H7	119.6
C3—C2—H2A	109.1	C6—C7—H7	119.6
N2—C2—H2B	109.1	C9—C8—C7	119.3 (3)
C3—C2—H2B	109.1	C9—C8—H8	120.3
H2A—C2—H2B	107.8	C7—C8—H8	120.3
C3i—C3—C2	114.0 (3)	C8—C9—C10	120.6 (3)
C3i—C3—H3A	108.8	C8—C9—H9	119.7
C2—C3—H3A	108.8	C10—C9—H9	119.7
C3i—C3—H3B	108.8	C5—C10—C9	120.7 (3)
C2—C3—H3B	108.8	C5—C10—H10	119.7
H3A—C3—H3B	107.7	C9—C10—H10	119.7
C2—N2—C1—N1	178.3 (2)	O1—C4—C5—C6	−166.1 (3)
C2—N2—C1—S1	−0.9 (4)	N1—C4—C5—C6	13.4 (4)
C4—N1—C1—N2	−0.3 (4)	C10—C5—C6—C7	0.5 (5)
C4—N1—C1—S1	179.0 (2)	C4—C5—C6—C7	179.0 (3)
C1—N2—C2—C3	88.5 (3)	C5—C6—C7—C8	0.2 (5)
N2—C2—C3—C3i	64.4 (4)	C6—C7—C8—C9	−0.6 (5)
C1—N1—C4—O1	4.7 (5)	C7—C8—C9—C10	0.3 (5)
C1—N1—C4—C5	−174.8 (3)	C6—C5—C10—C9	−0.8 (5)
O1—C4—C5—C10	12.4 (4)	C4—C5—C10—C9	−179.4 (3)
N1—C4—C5—C10	−168.1 (3)	C8—C9—C10—C5	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.06	2.717 (3)	133
C2—H2A···S1	0.97	2.68	3.060 (3)	103
C2—H2B···S1ii	0.97	2.72	3.468 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.06	2.717 (3)	133
C2—H2A⋯S1	0.97	2.68	3.060 (3)	103
C2—H2B⋯S1i	0.97	2.72	3.468 (3)	134

Symmetry code: (i) .