N-(2-Thienylmethyl-ene)-2-(2-{[2-(2-thienylmethyl-eneamino)phen-yl]sulfan-yl}ethyl-sulfan-yl)aniline.

The asymmetric unit of the title compound, C(24)H(20)N(2)S(4), contains one half-mol-ecule: a crystallographic centre of inversion is located at the mid-point of the two central C atoms. The thio-phene ring is oriented at a dihedral angle of 60.64 (3)° with respect to the benzene ring. In the crystal structure, π-π contacts between thio-phene rings [centroid-centroid distance = 3.581 (1) Å] may stabilize the structure. A weak C-H⋯π inter-action is also present.

Related literature

For related structures, see: Dharaa et al. (2005 ▶); Gok & Demirbas (1989 ▶); Kakanejadifard et al. (2007 ▶); Kakanejadifard & Amani (2008 ▶); Morshedi et al. (2009 ▶); Rajsekhar et al. (2002 ▶, 2004 ▶); Taylor et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H20N2S4

M = 464.66

Monoclinic,

a = 11.179 (5) Å

b = 7.730 (4) Å

c = 12.608 (6) Å

β = 91.899 (12)°

V = 1088.9 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.45 mm−1

T = 100 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.895, T max = 0.930

12880 measured reflections

2899 independent reflections

2569 reflections with I > 2/s(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.00

2899 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024404/hk2716sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024404/hk2716Isup2.hkl

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

C24H20N2S4	F(000) = 484
Mr = 464.66	Dx = 1.417 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 887 reflections
a = 11.179 (5) Å	θ = 3–30°
b = 7.730 (4) Å	µ = 0.45 mm−1
c = 12.608 (6) Å	T = 100 K
β = 91.899 (12)°	Prism, yellow
V = 1088.9 (9) Å3	0.30 × 0.20 × 0.15 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	2899 independent reflections
Radiation source: fine-focus sealed tube	2569 reflections with I > 2/s(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→15
Tmin = 0.895, Tmax = 0.930	k = −10→10
12880 measured reflections	l = −17→17

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.43P] where P = (Fo2 + 2Fc2)/3
2899 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.26 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	0.63766 (3)	−0.06436 (4)	0.88963 (2)	0.01981 (9)
S2	0.96427 (3)	0.15452 (4)	0.67870 (2)	0.01990 (9)
N1	0.79244 (9)	−0.14058 (14)	0.72259 (8)	0.0188 (2)
C1	0.51924 (11)	−0.09011 (16)	0.98300 (10)	0.0199 (2)
H1A	0.4507	−0.1525	0.9492	0.024*
H1B	0.5485	−0.1574	1.0454	0.024*
C2	0.64682 (11)	−0.27273 (16)	0.83345 (10)	0.0178 (2)
C3	0.58160 (11)	−0.41715 (17)	0.86395 (10)	0.0212 (3)
H3A	0.5258	−0.4071	0.9188	0.025*
C4	0.59782 (12)	−0.57566 (17)	0.81445 (11)	0.0232 (3)
H4A	0.5528	−0.6732	0.8357	0.028*
C5	0.67894 (12)	−0.59283 (18)	0.73454 (11)	0.0238 (3)
H5A	0.6912	−0.7024	0.7025	0.029*
C6	0.74233 (12)	−0.44926 (17)	0.70128 (10)	0.0216 (3)
H6A	0.7970	−0.4605	0.6456	0.026*
C7	0.72613 (10)	−0.28888 (16)	0.74913 (9)	0.0180 (2)
C8	0.79459 (11)	−0.09360 (17)	0.62510 (10)	0.0196 (2)
H8A	0.7488	−0.1565	0.5733	0.024*
C9	0.86458 (11)	0.05200 (17)	0.59218 (10)	0.0188 (2)
C10	0.86686 (12)	0.12347 (18)	0.49235 (10)	0.0213 (3)
H10A	0.8185	0.0843	0.4338	0.026*
C11	0.94924 (12)	0.26160 (18)	0.48653 (10)	0.0234 (3)
H11A	0.9619	0.3261	0.4237	0.028*
C12	1.00852 (12)	0.29220 (17)	0.58100 (10)	0.0223 (3)
H12B	1.0675	0.3797	0.5914	0.027*

	U11	U22	U33	U12	U13	U23
S1	0.01936 (16)	0.01889 (16)	0.02154 (16)	−0.00077 (11)	0.00610 (11)	−0.00011 (11)
S2	0.02172 (16)	0.02322 (17)	0.01469 (15)	−0.00207 (11)	−0.00047 (11)	−0.00144 (11)
N1	0.0163 (5)	0.0226 (5)	0.0174 (5)	−0.0002 (4)	0.0025 (4)	−0.0003 (4)
C1	0.0180 (6)	0.0221 (6)	0.0199 (6)	0.0015 (5)	0.0049 (4)	0.0027 (5)
C2	0.0168 (5)	0.0188 (6)	0.0178 (5)	0.0017 (4)	−0.0008 (4)	0.0010 (4)
C3	0.0190 (6)	0.0226 (6)	0.0221 (6)	−0.0004 (5)	0.0013 (5)	0.0045 (5)
C4	0.0226 (6)	0.0196 (6)	0.0270 (6)	−0.0027 (5)	−0.0036 (5)	0.0044 (5)
C5	0.0239 (6)	0.0210 (6)	0.0261 (6)	0.0016 (5)	−0.0053 (5)	−0.0026 (5)
C6	0.0196 (6)	0.0251 (6)	0.0200 (6)	0.0021 (5)	−0.0005 (5)	−0.0024 (5)
C7	0.0160 (5)	0.0210 (6)	0.0170 (5)	−0.0001 (4)	−0.0013 (4)	0.0014 (4)
C8	0.0173 (5)	0.0240 (6)	0.0176 (6)	0.0002 (5)	0.0007 (4)	−0.0011 (5)
C9	0.0173 (5)	0.0229 (6)	0.0163 (5)	0.0004 (4)	0.0001 (4)	−0.0020 (5)
C10	0.0220 (6)	0.0259 (6)	0.0159 (6)	0.0006 (5)	−0.0010 (4)	0.0000 (5)
C11	0.0277 (6)	0.0230 (6)	0.0198 (6)	0.0008 (5)	0.0034 (5)	0.0037 (5)
C12	0.0247 (6)	0.0193 (6)	0.0232 (6)	−0.0022 (5)	0.0032 (5)	0.0002 (5)

S1—C2	1.7639 (15)	C4—H4A	0.9500
S1—C1	1.8114 (14)	C5—C6	1.389 (2)
S2—C12	1.7132 (15)	C5—H5A	0.9500
S2—C9	1.7261 (14)	C6—C7	1.3932 (19)
N1—C8	1.2827 (17)	C6—H6A	0.9500
N1—C7	1.4114 (17)	C8—C9	1.4396 (18)
C1—C1i	1.524 (3)	C8—H8A	0.9500
C1—H1A	0.9900	C9—C10	1.3757 (18)
C1—H1B	0.9900	C10—C11	1.414 (2)
C2—C3	1.3944 (18)	C10—H10A	0.9500
C2—C7	1.4122 (17)	C11—C12	1.3644 (19)
C3—C4	1.3897 (19)	C11—H11A	0.9500
C3—H3A	0.9500	C12—H12B	0.9500
C4—C5	1.384 (2)
C2—S1—C1	102.36 (6)	C5—C6—C7	120.35 (12)
C12—S2—C9	91.53 (7)	C5—C6—H6A	119.8
C8—N1—C7	118.94 (11)	C7—C6—H6A	119.8
C1i—C1—S1	107.55 (11)	C6—C7—N1	122.90 (11)
C1i—C1—H1A	110.2	C6—C7—C2	119.91 (12)
S1—C1—H1A	110.2	N1—C7—C2	117.03 (11)
C1i—C1—H1B	110.2	N1—C8—C9	121.68 (12)
S1—C1—H1B	110.2	N1—C8—H8A	119.2
H1A—C1—H1B	108.5	C9—C8—H8A	119.2
C3—C2—C7	118.94 (12)	C10—C9—C8	127.19 (12)
C3—C2—S1	125.63 (10)	C10—C9—S2	111.26 (10)
C7—C2—S1	115.42 (9)	C8—C9—S2	121.50 (10)
C4—C3—C2	120.32 (12)	C9—C10—C11	112.50 (12)
C4—C3—H3A	119.8	C9—C10—H10A	123.7
C2—C3—H3A	119.8	C11—C10—H10A	123.7
C5—C4—C3	120.66 (12)	C12—C11—C10	112.59 (12)
C5—C4—H4A	119.7	C12—C11—H11A	123.7
C3—C4—H4A	119.7	C10—C11—H11A	123.7
C4—C5—C6	119.75 (13)	C11—C12—S2	112.12 (10)
C4—C5—H5A	120.1	C11—C12—H12B	123.9
C6—C5—H5A	120.1	S2—C12—H12B	123.9
C2—S1—C1—C1i	−166.07 (12)	S1—C2—C7—C6	178.23 (9)
C1—S1—C2—C3	−4.13 (13)	C3—C2—C7—N1	−178.52 (11)
C1—S1—C2—C7	174.52 (9)	S1—C2—C7—N1	2.73 (14)
C7—C2—C3—C4	2.25 (19)	C7—N1—C8—C9	−177.31 (11)
S1—C2—C3—C4	−179.14 (10)	N1—C8—C9—C10	−174.31 (13)
C2—C3—C4—C5	0.2 (2)	N1—C8—C9—S2	8.43 (18)
C3—C4—C5—C6	−1.9 (2)	C12—S2—C9—C10	−0.04 (10)
C4—C5—C6—C7	1.1 (2)	C12—S2—C9—C8	177.62 (11)
C5—C6—C7—N1	176.60 (12)	C8—C9—C10—C11	−177.69 (12)
C5—C6—C7—C2	1.38 (19)	S2—C9—C10—C11	−0.20 (15)
C8—N1—C7—C6	53.92 (17)	C9—C10—C11—C12	0.42 (17)
C8—N1—C7—C2	−130.73 (13)	C10—C11—C12—S2	−0.44 (15)
C3—C2—C7—C6	−3.02 (18)	C9—S2—C12—C11	0.28 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg1ii	0.95	2.80	3.740 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg1i	0.95	2.80	3.740 (3)	171

Symmetry code: (i) . Cg1 is centroid of the ring C2–C7 ring.