(E)-[({[(3-Methyl-phen-yl)meth-yl]sulfan-yl}methane-thio-yl)amino](1-phenyl-pentyl-idene)amine.

In the structure of the title compound, C(20)H(24)N(2)S(2), the central CN(2)S(2) atoms are planar (r.m.s. deviation = 0.0205 Å) but both benzene rings are twisted out of this plane forming dihedral angles of 23.03 (6) and 84.75 (4)° (tol-yl); the n-butyl group occupies a position normal to the plane [N-C-C-C torsion angle = -84.33 (16)°]. The conformation of the imine bond [1.2888 (18) Å] is E. The syn arrangement of the thione S and amino H atoms enables the formation of N-H⋯S hydrogen bonds between centrosymmetrically related mol-ecules. These lead to eight-membered {⋯HNC=S}(2) synthons which are further stabilized by proximate C-H⋯S interactions. The resulting dimeric aggregates are connected into a supra-molecular chain along the c axis by C-H⋯π(tol-yl) inter-actions.

Related literature

For background on the coordination chemistry of hydrazine­carbodithio­ates, see: Ravoof et al. (2010 ▶). For related structures, see: Khoo et al. (2005 ▶); How et al. (2007 ▶).

Experimental

Crystal data

C20H24N2S2

M = 356.53

Monoclinic,

a = 11.3345 (1) Å

b = 19.1439 (3) Å

c = 8.6779 (1) Å

β = 95.802 (1)°

V = 1873.34 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.58 mm−1

T = 150 K

0.18 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.820, T max = 0.924

33884 measured reflections

3631 independent reflections

3380 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.03

3631 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016965/hg5033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016965/hg5033Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016965/hg5033Isup3.cml

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

C20H24N2S2	F(000) = 760
Mr = 356.53	Dx = 1.264 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 23382 reflections
a = 11.3345 (1) Å	θ = 3.9–71.2°
b = 19.1439 (3) Å	µ = 2.58 mm−1
c = 8.6779 (1) Å	T = 150 K
β = 95.802 (1)°	Block, pale-yellow
V = 1873.34 (4) Å3	0.18 × 0.14 × 0.06 mm
Z = 4

Oxford Diffraction Xcaliber Eos Gemini diffractometer	3631 independent reflections
Radiation source: fine-focus sealed tube	3380 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 16.1952 pixels mm-1	θmax = 71.4°, θmin = 3.9°
ω/2θ scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −22→23
Tmin = 0.820, Tmax = 0.924	l = −10→10
33884 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.5891P] where P = (Fo2 + 2Fc2)/3
3631 reflections	(Δ/σ)max = 0.002
222 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.02007 (3)	0.442478 (17)	0.29961 (4)	0.02821 (11)
S2	0.18648 (3)	0.521432 (17)	0.10978 (4)	0.02677 (11)
N1	0.08701 (10)	0.57396 (6)	0.33862 (13)	0.0265 (3)
H1N	0.0476 (14)	0.5734 (9)	0.4199 (15)	0.032*
N2	0.15725 (10)	0.62898 (6)	0.29997 (13)	0.0257 (2)
C1	0.09447 (11)	0.51415 (7)	0.25919 (15)	0.0233 (3)
C2	0.13749 (12)	0.69067 (7)	0.35107 (15)	0.0239 (3)
C3	0.21717 (12)	0.74591 (7)	0.29942 (15)	0.0245 (3)
C4	0.19755 (13)	0.81656 (8)	0.32641 (17)	0.0298 (3)
H4	0.1342	0.8301	0.3837	0.036*
C5	0.26964 (14)	0.86719 (8)	0.27053 (19)	0.0357 (3)
H5	0.2548	0.9152	0.2888	0.043*
C6	0.36287 (14)	0.84832 (9)	0.18845 (19)	0.0368 (3)
H6	0.4120	0.8832	0.1503	0.044*
C7	0.38448 (13)	0.77831 (9)	0.16191 (19)	0.0362 (3)
H7	0.4489	0.7651	0.1062	0.043*
C8	0.31210 (13)	0.72760 (8)	0.21670 (17)	0.0306 (3)
H8	0.3272	0.6797	0.1978	0.037*
C9	0.03642 (12)	0.70935 (7)	0.44343 (15)	0.0253 (3)
H9A	0.0578	0.7511	0.5075	0.030*
H9B	0.0215	0.6703	0.5137	0.030*
C10	−0.07651 (12)	0.72428 (7)	0.33483 (15)	0.0265 (3)
H10A	−0.0635	0.7664	0.2724	0.032*
H10B	−0.0918	0.6845	0.2627	0.032*
C11	−0.18508 (13)	0.73576 (8)	0.42165 (17)	0.0308 (3)
H11A	−0.1981	0.6936	0.4839	0.037*
H11B	−0.1696	0.7754	0.4941	0.037*
C12	−0.29719 (13)	0.75075 (9)	0.3150 (2)	0.0372 (3)
H12A	−0.2865	0.7937	0.2567	0.056*
H12B	−0.3642	0.7565	0.3770	0.056*
H12C	−0.3131	0.7117	0.2428	0.056*
C13	0.17797 (13)	0.43434 (7)	0.02445 (18)	0.0296 (3)
H13A	0.1842	0.3982	0.1064	0.035*
H13B	0.1018	0.4281	−0.0407	0.035*
C14	0.28092 (12)	0.42893 (7)	−0.07279 (16)	0.0260 (3)
C15	0.26557 (12)	0.44105 (7)	−0.23135 (17)	0.0269 (3)
H15	0.1886	0.4515	−0.2797	0.032*
C16	0.36119 (13)	0.43818 (7)	−0.32117 (17)	0.0285 (3)
C17	0.47312 (13)	0.42296 (8)	−0.24810 (17)	0.0310 (3)
H17	0.5392	0.4209	−0.3072	0.037*
C18	0.48925 (13)	0.41079 (8)	−0.08963 (18)	0.0333 (3)
H18	0.5661	0.4004	−0.0411	0.040*
C19	0.39395 (13)	0.41375 (8)	−0.00206 (17)	0.0309 (3)
H19	0.4055	0.4054	0.1063	0.037*
C20	0.34264 (15)	0.45187 (10)	−0.49302 (19)	0.0431 (4)
H20A	0.3238	0.5013	−0.5112	0.065*
H20B	0.2770	0.4231	−0.5395	0.065*
H20C	0.4151	0.4401	−0.5401	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0308 (2)	0.02422 (19)	0.03141 (19)	−0.00527 (12)	0.01214 (14)	−0.00176 (13)
S2	0.03181 (19)	0.02038 (18)	0.03037 (19)	−0.00134 (12)	0.01409 (14)	−0.00156 (12)
N1	0.0300 (6)	0.0232 (6)	0.0281 (6)	−0.0013 (4)	0.0118 (5)	−0.0015 (4)
N2	0.0273 (6)	0.0215 (6)	0.0290 (6)	−0.0007 (4)	0.0066 (4)	−0.0008 (4)
C1	0.0221 (6)	0.0231 (6)	0.0252 (6)	0.0019 (5)	0.0049 (5)	0.0017 (5)
C2	0.0262 (6)	0.0242 (7)	0.0211 (6)	0.0035 (5)	0.0008 (5)	0.0000 (5)
C3	0.0254 (6)	0.0239 (7)	0.0233 (6)	0.0009 (5)	−0.0019 (5)	−0.0007 (5)
C4	0.0299 (7)	0.0257 (7)	0.0334 (7)	0.0020 (5)	0.0019 (6)	−0.0028 (6)
C5	0.0381 (8)	0.0242 (7)	0.0438 (8)	−0.0020 (6)	−0.0003 (7)	−0.0010 (6)
C6	0.0346 (8)	0.0354 (8)	0.0400 (8)	−0.0110 (6)	0.0016 (6)	0.0045 (6)
C7	0.0295 (7)	0.0403 (9)	0.0399 (8)	−0.0018 (6)	0.0088 (6)	0.0002 (7)
C8	0.0296 (7)	0.0273 (7)	0.0353 (7)	0.0017 (6)	0.0052 (6)	−0.0011 (6)
C9	0.0304 (7)	0.0224 (6)	0.0237 (6)	0.0014 (5)	0.0052 (5)	−0.0014 (5)
C10	0.0275 (7)	0.0265 (7)	0.0260 (6)	−0.0003 (5)	0.0050 (5)	−0.0018 (5)
C11	0.0312 (7)	0.0293 (7)	0.0332 (7)	0.0011 (6)	0.0092 (6)	−0.0005 (6)
C12	0.0287 (7)	0.0371 (8)	0.0466 (9)	0.0038 (6)	0.0077 (6)	−0.0051 (7)
C13	0.0322 (7)	0.0217 (7)	0.0370 (7)	−0.0021 (5)	0.0137 (6)	−0.0064 (6)
C14	0.0288 (7)	0.0184 (6)	0.0323 (7)	−0.0002 (5)	0.0107 (5)	−0.0039 (5)
C15	0.0249 (7)	0.0216 (7)	0.0346 (7)	0.0012 (5)	0.0050 (5)	0.0001 (5)
C16	0.0298 (7)	0.0259 (7)	0.0306 (7)	−0.0002 (5)	0.0069 (6)	0.0012 (5)
C17	0.0266 (7)	0.0327 (7)	0.0353 (7)	0.0032 (6)	0.0116 (6)	0.0011 (6)
C18	0.0256 (7)	0.0369 (8)	0.0374 (8)	0.0052 (6)	0.0035 (6)	0.0026 (6)
C19	0.0340 (7)	0.0311 (8)	0.0282 (7)	0.0014 (6)	0.0065 (6)	0.0000 (6)
C20	0.0372 (9)	0.0600 (11)	0.0326 (8)	−0.0027 (8)	0.0063 (7)	0.0077 (7)

S1—C1	1.6663 (13)	C10—H10B	0.9900
S2—C1	1.7497 (13)	C11—C12	1.522 (2)
S2—C13	1.8229 (14)	C11—H11A	0.9900
N1—C1	1.3434 (18)	C11—H11B	0.9900
N1—N2	1.3820 (16)	C12—H12A	0.9800
N1—H1N	0.872 (9)	C12—H12B	0.9800
N2—C2	1.2888 (18)	C12—H12C	0.9800
C2—C3	1.4889 (19)	C13—C14	1.5111 (18)
C2—C9	1.5061 (18)	C13—H13A	0.9900
C3—C4	1.394 (2)	C13—H13B	0.9900
C3—C8	1.397 (2)	C14—C15	1.389 (2)
C4—C5	1.387 (2)	C14—C19	1.394 (2)
C4—H4	0.9500	C15—C16	1.399 (2)
C5—C6	1.381 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.391 (2)
C6—C7	1.386 (2)	C16—C20	1.508 (2)
C6—H6	0.9500	C17—C18	1.388 (2)
C7—C8	1.386 (2)	C17—H17	0.9500
C7—H7	0.9500	C18—C19	1.383 (2)
C8—H8	0.9500	C18—H18	0.9500
C9—C10	1.5377 (19)	C19—H19	0.9500
C9—H9A	0.9900	C20—H20A	0.9800
C9—H9B	0.9900	C20—H20B	0.9800
C10—C11	1.5224 (19)	C20—H20C	0.9800
C10—H10A	0.9900
C1—S2—C13	102.54 (6)	C12—C11—H11A	108.9
C1—N1—N2	117.22 (11)	C10—C11—H11A	108.9
C1—N1—H1N	118.0 (12)	C12—C11—H11B	108.9
N2—N1—H1N	124.0 (12)	C10—C11—H11B	108.9
C2—N2—N1	119.37 (11)	H11A—C11—H11B	107.8
N1—C1—S1	122.30 (10)	C11—C12—H12A	109.5
N1—C1—S2	112.67 (10)	C11—C12—H12B	109.5
S1—C1—S2	125.01 (8)	H12A—C12—H12B	109.5
N2—C2—C3	114.55 (12)	C11—C12—H12C	109.5
N2—C2—C9	124.65 (12)	H12A—C12—H12C	109.5
C3—C2—C9	120.57 (11)	H12B—C12—H12C	109.5
C4—C3—C8	118.29 (13)	C14—C13—S2	106.10 (9)
C4—C3—C2	121.77 (12)	C14—C13—H13A	110.5
C8—C3—C2	119.90 (12)	S2—C13—H13A	110.5
C5—C4—C3	120.64 (14)	C14—C13—H13B	110.5
C5—C4—H4	119.7	S2—C13—H13B	110.5
C3—C4—H4	119.7	H13A—C13—H13B	108.7
C6—C5—C4	120.42 (14)	C15—C14—C19	119.24 (13)
C6—C5—H5	119.8	C15—C14—C13	121.02 (13)
C4—C5—H5	119.8	C19—C14—C13	119.71 (13)
C5—C6—C7	119.73 (14)	C14—C15—C16	121.27 (13)
C5—C6—H6	120.1	C14—C15—H15	119.4
C7—C6—H6	120.1	C16—C15—H15	119.4
C8—C7—C6	119.99 (14)	C17—C16—C15	118.48 (13)
C8—C7—H7	120.0	C17—C16—C20	121.12 (13)
C6—C7—H7	120.0	C15—C16—C20	120.40 (14)
C7—C8—C3	120.92 (14)	C18—C17—C16	120.63 (13)
C7—C8—H8	119.5	C18—C17—H17	119.7
C3—C8—H8	119.5	C16—C17—H17	119.7
C2—C9—C10	110.42 (11)	C19—C18—C17	120.35 (14)
C2—C9—H9A	109.6	C19—C18—H18	119.8
C10—C9—H9A	109.6	C17—C18—H18	119.8
C2—C9—H9B	109.6	C18—C19—C14	120.03 (13)
C10—C9—H9B	109.6	C18—C19—H19	120.0
H9A—C9—H9B	108.1	C14—C19—H19	120.0
C11—C10—C9	112.83 (11)	C16—C20—H20A	109.5
C11—C10—H10A	109.0	C16—C20—H20B	109.5
C9—C10—H10A	109.0	H20A—C20—H20B	109.5
C11—C10—H10B	109.0	C16—C20—H20C	109.5
C9—C10—H10B	109.0	H20A—C20—H20C	109.5
H10A—C10—H10B	107.8	H20B—C20—H20C	109.5
C12—C11—C10	113.17 (12)
C1—N1—N2—C2	167.00 (12)	C2—C3—C8—C7	177.31 (13)
N2—N1—C1—S1	176.84 (10)	N2—C2—C9—C10	−84.33 (16)
N2—N1—C1—S2	−4.54 (15)	C3—C2—C9—C10	89.91 (14)
C13—S2—C1—N1	−179.56 (10)	C2—C9—C10—C11	173.76 (11)
C13—S2—C1—S1	−0.98 (11)	C9—C10—C11—C12	179.86 (12)
N1—N2—C2—C3	−178.88 (11)	C1—S2—C13—C14	−163.64 (10)
N1—N2—C2—C9	−4.3 (2)	S2—C13—C14—C15	−97.18 (14)
N2—C2—C3—C4	171.08 (12)	S2—C13—C14—C19	80.75 (14)
C9—C2—C3—C4	−3.72 (19)	C19—C14—C15—C16	0.1 (2)
N2—C2—C3—C8	−6.59 (18)	C13—C14—C15—C16	178.05 (12)
C9—C2—C3—C8	178.62 (12)	C14—C15—C16—C17	−0.1 (2)
C8—C3—C4—C5	0.9 (2)	C14—C15—C16—C20	−179.68 (14)
C2—C3—C4—C5	−176.83 (13)	C15—C16—C17—C18	0.1 (2)
C3—C4—C5—C6	−0.6 (2)	C20—C16—C17—C18	179.67 (15)
C4—C5—C6—C7	0.0 (2)	C16—C17—C18—C19	−0.1 (2)
C5—C6—C7—C8	0.5 (2)	C17—C18—C19—C14	0.1 (2)
C6—C7—C8—C3	−0.2 (2)	C15—C14—C19—C18	−0.1 (2)
C4—C3—C8—C7	−0.4 (2)	C13—C14—C19—C18	−178.05 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.87 (1)	2.64 (1)	3.4926 (12)	165.(1)
C9—H9B···S1i	0.99	2.77	3.7576 (14)	178
C12—H12C···Cg1ii	0.98	2.81	3.7162 (14)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.87 (1)	2.64 (1)	3.4926 (12)	165 (1)
C9—H9B⋯S1i	0.99	2.77	3.7576 (14)	178
C12—H12C⋯Cg1ii	0.98	2.81	3.7162 (14)	155

Symmetry codes: (i) ; (ii) .