(E)-[({[(3-Methyl­phen­yl)meth­yl]sulfan­yl}methane­thio­yl)amino](1-phenyl­pentyl­idene)amine

Paulus, G.; Crouse, K.A.; Mohamed Tahir, M.I.; Tiekink, E.R.T.

doi:10.1107/S1600536811016965

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1370-o1371

doi:10.1107/S1600536811016965

Open

access

(E)-[({[(3-Methylphenyl)methyl]sulfanyl}methanethioyl)amino](1-phenylpentylidene)amine

Georgiana Paulus,^a Karen A. Crouse,^a ‡ Mohamed Ibrahim Mohamed Tahir ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 4 May 2011; accepted 5 May 2011; online 11 May 2011)

In the structure of the title compound, C₂₀H₂₄N₂S₂, the central CN₂S₂ 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)° (tolyl); 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 molecules. 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 supramolecular chain along the c axis by C—H⋯π(tolyl) interactions.

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_r = 356.53
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) 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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.03
3631 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x, -y+1, -z+1; (ii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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 ).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811016965/hg5033Isup3.cml

checkCIF report

Comment top

In continuing interest in the coordination chemistry of hydrazinecarbodithioate derivatives (Ravoof et al., 2010), structural studies on the precursor molecules have been undertaken (Khoo et al. 2005; How et al. 2007). In this connection, the title compound, (I), the product of the condensation reaction between 3-methylbenzyldithiocarbazate and valerophenone, was investigated.

The central CN₂S₂ atoms in the molecular structure of (I), Fig. 1, are planar with a r.m.s. = 0.0205 Å. The adjacent residues are twisted out of this plane as seen in the values of the C1—N1—N2—C2 and C1—S2—C13—C14 torsion angles of 167.00 (12) and -163.64 (10) °, respectively. Further, the dihedral angles formed between the C3···C6 and C14···C19 benzene rings with the central plane are 23.03 (6) and 84.75 (4) °, respectively, indicating approximate co-planar and a perpendicular dispositions, respectively. Thus, the benzene rings are almost normal to each other, forming a dihedral angle between their respective least-squares planes of 80.13 (5) °. Finally, the n-butyl group, having an extended conformation, occupies a position approximately normal to the central plane with N2—C2—C9—C10 torsion angle being -84.33 (16) °. The conformation about the N2═C2 bond [1.2888 (18) Å] is E. The thione-S1 and amino-H atoms are syn, a disposition that allows for the formation of N—H···S hydrogen bonds between centrosymmetrically related molecules, Table 1. These lead to eight-membered {···HNC═S}₂ synthons which are further stabilized by proximate C—H···S interactions, Table 1. The dimeric aggregates are connected into linear supramolecular chains along the c axis via C—H···π(C14···C19) contacts, Table 1 and Fig. 2. The chains pack into layers in the ac plane and their organic residues inter-digitate along the b axis, Fig. 3.

Related literature top

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 top

The precursor molecule 3-methylbenzyldithiocarbazate was prepared as previously described (Ravoof et al., 2010). This (2.12 g, 0.01 mol) was dissolved in acetonitrile (35 ml) and valerophenone (1.62 g, 0.01 mol) was added. The temperature of the reaction mixture was maintained between 333–338 K with stirring over 30 min. as a yellow product formed. The product was filtered off, recrystallized and dried in vacuo over silica gel (yield 70%; M.pt. 366 K). Anal. Found (Calc.): C, 66.25 (67.37), H, 6.50 (6.78), N, 7.81 (7.86), S, 18.17 (17.99) %. Light-yellow crystals were grown from its acetonitrile solution through slow evaporation.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top

	Fig. 1. The molecular structure of of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain in (I) mediated by N—H···S hydrogen bonding and C—H···π interactions, shown as orange and purple dashed lines, respectively.
	Fig. 3. A view in projection down the a axis of the unit-cell contents for (I) showing inter-digitation of organic residues along the b axis. The N—H···S hydrogen bonding and C—H···π interactions are shown as orange and purple dashed lines, respectively.

(E)-[({[(3-Methylphenyl)methyl]sulfanyl}methanethioyl)amino](1- phenylpentylidene)amine top

Crystal data top

C₂₀H₂₄N₂S₂	F(000) = 760
M_r = 356.53	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0606P)² + 0.5891P] where P = (F_o² + 2F_c²)/3
3631 reflections	(Δ/σ)_max = 0.002
222 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₂₄N₂S₂	V = 1873.34 (4) Å³
M_r = 356.53	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.3345 (1) Å	µ = 2.58 mm⁻¹
b = 19.1439 (3) Å	T = 150 K
c = 8.6779 (1) Å	0.18 × 0.14 × 0.06 mm
β = 95.802 (1)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	3631 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3380 reflections with I > 2σ(I)
T_min = 0.820, T_max = 0.924	R_int = 0.023
33884 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
3631 reflections	Δρ_min = −0.18 e Å⁻³
222 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₂S₂
M_r	356.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	11.3345 (1), 19.1439 (3), 8.6779 (1)
β (°)	95.802 (1)
V (Å³)	1873.34 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.58
Crystal size (mm)	0.18 × 0.14 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.820, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	33884, 3631, 3380
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.03
No. of reflections	3631
No. of parameters	222
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.872 (14)	2.643 (14)	3.4926 (12)	165.1 (14)
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) −x, −y+1, −z+1; (ii) −x, −y+1, −z.

Footnotes

‡Additional correspondence author, e-mail: kacrouse@gmail.com.

Acknowledgements

Support for the project came from Universiti Putra Malaysia under their Research University Grant Scheme (grant No. 9174000) and from the Malaysian Ministry of Science, Technology and Innovation (grant No. 09-02-04-0752-EA001).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023–o3024. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441–o2443. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkins, D. J. (2010). Transition Met. Chem. 35, 871–876. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1370-o1371

doi:10.1107/S1600536811016965

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-[({[(3-Methyl­phen­yl)meth­yl]sulfan­yl}methane­thio­yl)amino](1-phenyl­pentyl­­idene)amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-[({[(3-Methylphenyl)methyl]sulfanyl}methanethioyl)amino](1-phenylpentylidene)amine