Bis[2-(benzyl-idene-amino)-phen-yl] disulfide.

In the title mol-ecule, C(26)H(20)N(2)S(2), the two benzene rings connected by a disulfide chain form a dihedral angle of 84.9 (1)°, and the two benzene rings in the two benzyl-idene-amino-phenyl fragments form dihedral angles of 34.4 (1) and 32.8 (1)°. The crystal structure exhibits weak inter-molecular C-H⋯S hydrogen bonds, which link the mol-ecules into chains along [101].

Related literature

For general background to Schiff bases and their synthesis, see: Wang et al. (1998 ▶); Bai et al. (2005 ▶). For a related structure, see: He et al. (2011 ▶).

Experimental

Crystal data

C26H20N2S2

M = 424.56

Monoclinic,

a = 10.2421 (11) Å

b = 19.672 (2) Å

c = 11.4739 (13) Å

β = 97.198 (1)°

V = 2293.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.43 × 0.35 × 0.31 mm

Data collection

Bruker SMART APEX CCD area-etector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.901, T max = 0.927

11618 measured reflections

4043 independent reflections

1764 reflections with I > 2σ(I)

R int = 0.125

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.197

S = 1.05

4043 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048239/cv5194sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048239/cv5194Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048239/cv5194Isup3.cml

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

C26H20N2S2	F(000) = 888
Mr = 424.56	Dx = 1.230 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2421 (11) Å	Cell parameters from 2078 reflections
b = 19.672 (2) Å	θ = 2.7–20.1°
c = 11.4739 (13) Å	µ = 0.25 mm−1
β = 97.198 (1)°	T = 298 K
V = 2293.5 (4) Å3	Block, yellow
Z = 4	0.43 × 0.35 × 0.31 mm

Bruker SMART APEX CCD area-etector diffractometer	4043 independent reflections
Radiation source: fine-focus sealed tube	1764 reflections with I > 2σ(I)
graphite	Rint = 0.125
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.901, Tmax = 0.927	k = −20→23
11618 measured reflections	l = −13→11

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.9182P] where P = (Fo2 + 2Fc2)/3
4043 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.3113 (4)	0.0052 (2)	0.2975 (3)	0.0710 (11)
N2	−0.1878 (4)	0.2777 (2)	0.1398 (3)	0.0691 (11)
S1	0.03931 (13)	0.20245 (7)	0.22438 (11)	0.0799 (5)
S2	0.13336 (13)	0.11360 (7)	0.27203 (11)	0.0730 (5)
C1	−0.0581 (4)	0.1836 (2)	0.0887 (4)	0.0634 (13)
C2	−0.0300 (5)	0.1322 (3)	0.0121 (4)	0.0793 (15)
H2	0.0438	0.1049	0.0310	0.095*
C3	−0.1116 (6)	0.1215 (3)	−0.0918 (5)	0.0934 (18)
H3	−0.0924	0.0871	−0.1427	0.112*
C4	−0.2203 (6)	0.1613 (3)	−0.1198 (5)	0.1015 (19)
H4	−0.2759	0.1534	−0.1890	0.122*
C5	−0.2480 (5)	0.2136 (3)	−0.0457 (4)	0.0833 (16)
H5	−0.3215	0.2409	−0.0659	0.100*
C6	−0.1665 (5)	0.2255 (3)	0.0588 (4)	0.0660 (13)
C7	−0.2390 (5)	0.3338 (3)	0.1026 (4)	0.0725 (14)
H7	−0.2612	0.3392	0.0220	0.087*
C8	−0.2650 (5)	0.3901 (3)	0.1794 (5)	0.0715 (14)
C9	−0.3206 (5)	0.4488 (3)	0.1287 (6)	0.0952 (18)
H9	−0.3408	0.4520	0.0476	0.114*
C10	−0.3455 (6)	0.5022 (4)	0.1994 (8)	0.120 (2)
H10	−0.3823	0.5418	0.1654	0.144*
C11	−0.3178 (7)	0.4986 (3)	0.3175 (8)	0.111 (2)
H11	−0.3384	0.5349	0.3639	0.133*
C12	−0.2592 (6)	0.4413 (3)	0.3693 (6)	0.1038 (19)
H12	−0.2372	0.4391	0.4503	0.125*
C13	−0.2333 (6)	0.3868 (3)	0.2991 (5)	0.0928 (17)
H13	−0.1942	0.3478	0.3333	0.111*
C14	0.2829 (5)	0.1152 (2)	0.2100 (4)	0.0651 (13)
C15	0.3270 (6)	0.1690 (3)	0.1459 (5)	0.0845 (16)
H15	0.2761	0.2082	0.1344	0.101*
C16	0.4451 (7)	0.1652 (3)	0.0993 (6)	0.115 (2)
H16	0.4732	0.2015	0.0569	0.138*
C17	0.5212 (6)	0.1068 (4)	0.1163 (7)	0.128 (3)
H17	0.6001	0.1035	0.0843	0.153*
C18	0.4787 (6)	0.0531 (3)	0.1814 (6)	0.108 (2)
H18	0.5296	0.0139	0.1924	0.130*
C19	0.3620 (5)	0.0573 (3)	0.2299 (4)	0.0732 (14)
C20	0.3876 (5)	−0.0331 (3)	0.3620 (5)	0.0722 (14)
H20	0.4779	−0.0266	0.3646	0.087*
C21	0.3406 (6)	−0.0872 (2)	0.4330 (4)	0.0667 (13)
C22	0.2066 (6)	−0.1007 (3)	0.4311 (5)	0.0795 (15)
H22	0.1453	−0.0757	0.3819	0.095*
C23	0.1646 (6)	−0.1507 (3)	0.5016 (6)	0.0992 (18)
H23	0.0752	−0.1598	0.4990	0.119*
C24	0.2532 (9)	−0.1871 (3)	0.5753 (6)	0.104 (2)
H24	0.2237	−0.2198	0.6243	0.125*
C25	0.3835 (9)	−0.1760 (3)	0.5775 (6)	0.111 (2)
H25	0.4436	−0.2019	0.6263	0.134*
C26	0.4280 (6)	−0.1253 (3)	0.5061 (5)	0.0976 (18)
H26	0.5178	−0.1175	0.5083	0.117*

	U11	U22	U33	U12	U13	U23
N1	0.088 (3)	0.058 (3)	0.067 (3)	−0.001 (2)	0.009 (2)	0.006 (2)
N2	0.087 (3)	0.063 (3)	0.056 (2)	0.008 (2)	0.001 (2)	0.007 (2)
S1	0.0979 (10)	0.0781 (10)	0.0572 (8)	0.0153 (7)	−0.0157 (7)	−0.0105 (7)
S2	0.0825 (9)	0.0791 (9)	0.0549 (7)	0.0065 (7)	−0.0016 (6)	0.0091 (7)
C1	0.074 (3)	0.065 (3)	0.048 (3)	0.000 (3)	−0.005 (2)	0.005 (3)
C2	0.097 (4)	0.081 (4)	0.058 (3)	0.014 (3)	0.000 (3)	−0.006 (3)
C3	0.128 (5)	0.089 (4)	0.057 (3)	0.015 (4)	−0.011 (3)	−0.017 (3)
C4	0.128 (5)	0.105 (5)	0.061 (3)	0.013 (4)	−0.028 (3)	−0.016 (4)
C5	0.096 (4)	0.086 (4)	0.061 (3)	0.013 (3)	−0.017 (3)	0.005 (3)
C6	0.081 (3)	0.069 (3)	0.046 (3)	0.001 (3)	0.001 (2)	0.000 (3)
C7	0.083 (3)	0.076 (4)	0.057 (3)	0.001 (3)	0.005 (3)	0.011 (3)
C8	0.083 (3)	0.061 (3)	0.071 (4)	0.005 (3)	0.013 (3)	0.008 (3)
C9	0.109 (4)	0.078 (4)	0.096 (4)	0.022 (3)	0.006 (4)	0.009 (4)
C10	0.133 (6)	0.087 (5)	0.139 (7)	0.033 (4)	0.020 (5)	0.005 (5)
C11	0.131 (5)	0.073 (5)	0.137 (7)	0.008 (4)	0.052 (5)	−0.013 (5)
C12	0.153 (6)	0.079 (4)	0.082 (4)	−0.015 (4)	0.026 (4)	−0.002 (4)
C13	0.140 (5)	0.059 (4)	0.083 (4)	0.007 (3)	0.028 (4)	0.009 (3)
C14	0.071 (3)	0.062 (3)	0.060 (3)	0.000 (3)	−0.002 (2)	0.004 (3)
C15	0.091 (4)	0.072 (4)	0.089 (4)	0.004 (3)	0.004 (3)	0.022 (3)
C16	0.109 (5)	0.103 (5)	0.136 (6)	0.004 (4)	0.027 (5)	0.057 (5)
C17	0.104 (5)	0.135 (6)	0.155 (7)	0.014 (5)	0.053 (5)	0.059 (6)
C18	0.104 (5)	0.093 (5)	0.132 (6)	0.020 (4)	0.038 (4)	0.038 (4)
C19	0.071 (3)	0.075 (4)	0.072 (3)	0.000 (3)	0.003 (3)	0.008 (3)
C20	0.080 (3)	0.063 (3)	0.074 (3)	0.006 (3)	0.011 (3)	0.001 (3)
C21	0.090 (4)	0.053 (3)	0.057 (3)	0.008 (3)	0.008 (3)	−0.003 (3)
C22	0.099 (4)	0.058 (3)	0.082 (4)	0.003 (3)	0.013 (3)	0.006 (3)
C23	0.118 (5)	0.076 (4)	0.104 (5)	−0.013 (4)	0.019 (4)	0.005 (4)
C24	0.171 (7)	0.054 (4)	0.089 (5)	0.002 (4)	0.021 (5)	0.008 (3)
C25	0.157 (7)	0.075 (4)	0.101 (5)	0.042 (5)	0.008 (5)	0.020 (4)
C26	0.115 (5)	0.082 (4)	0.095 (4)	0.024 (4)	0.011 (4)	0.019 (4)

N1—C20	1.258 (6)	C12—C13	1.386 (7)
N1—C19	1.423 (6)	C12—H12	0.9300
N2—C7	1.272 (5)	C13—H13	0.9300
N2—C6	1.420 (6)	C14—C15	1.395 (7)
S1—C1	1.779 (4)	C14—C19	1.400 (6)
S1—S2	2.0371 (18)	C15—C16	1.385 (7)
S2—C14	1.768 (5)	C15—H15	0.9300
C1—C6	1.391 (6)	C16—C17	1.389 (8)
C1—C2	1.394 (6)	C16—H16	0.9300
C2—C3	1.383 (7)	C17—C18	1.394 (8)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.367 (7)	C18—C19	1.383 (7)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.386 (7)	C20—C21	1.458 (7)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.393 (6)	C21—C26	1.371 (7)
C5—H5	0.9300	C21—C22	1.395 (7)
C7—C8	1.461 (7)	C22—C23	1.377 (7)
C7—H7	0.9300	C22—H22	0.9300
C8—C13	1.372 (7)	C23—C24	1.363 (8)
C8—C9	1.383 (7)	C23—H23	0.9300
C9—C10	1.370 (8)	C24—C25	1.349 (8)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.351 (9)	C25—C26	1.402 (8)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.377 (8)	C26—H26	0.9300
C11—H11	0.9300
C20—N1—C19	120.7 (5)	C8—C13—H13	119.8
C7—N2—C6	119.9 (4)	C12—C13—H13	119.8
C1—S1—S2	104.50 (17)	C15—C14—C19	119.0 (5)
C14—S2—S1	106.31 (17)	C15—C14—S2	125.4 (4)
C6—C1—C2	119.7 (4)	C19—C14—S2	115.6 (4)
C6—C1—S1	115.8 (4)	C16—C15—C14	121.2 (5)
C2—C1—S1	124.5 (4)	C16—C15—H15	119.4
C3—C2—C1	120.3 (5)	C14—C15—H15	119.4
C3—C2—H2	119.9	C15—C16—C17	119.6 (6)
C1—C2—H2	119.9	C15—C16—H16	120.2
C4—C3—C2	120.1 (5)	C17—C16—H16	120.2
C4—C3—H3	119.9	C16—C17—C18	119.6 (6)
C2—C3—H3	119.9	C16—C17—H17	120.2
C3—C4—C5	120.3 (5)	C18—C17—H17	120.2
C3—C4—H4	119.8	C19—C18—C17	120.9 (6)
C5—C4—H4	119.8	C19—C18—H18	119.5
C4—C5—C6	120.4 (5)	C17—C18—H18	119.5
C4—C5—H5	119.8	C18—C19—C14	119.7 (5)
C6—C5—H5	119.8	C18—C19—N1	124.7 (5)
C1—C6—C5	119.1 (5)	C14—C19—N1	115.6 (5)
C1—C6—N2	116.8 (4)	N1—C20—C21	122.8 (5)
C5—C6—N2	124.1 (5)	N1—C20—H20	118.6
N2—C7—C8	123.6 (5)	C21—C20—H20	118.6
N2—C7—H7	118.2	C26—C21—C22	118.1 (5)
C8—C7—H7	118.2	C26—C21—C20	120.3 (5)
C13—C8—C9	119.6 (5)	C22—C21—C20	121.6 (5)
C13—C8—C7	122.0 (5)	C23—C22—C21	120.4 (5)
C9—C8—C7	118.4 (5)	C23—C22—H22	119.8
C10—C9—C8	119.2 (6)	C21—C22—H22	119.8
C10—C9—H9	120.4	C24—C23—C22	120.5 (6)
C8—C9—H9	120.4	C24—C23—H23	119.8
C11—C10—C9	121.6 (7)	C22—C23—H23	119.8
C11—C10—H10	119.2	C25—C24—C23	120.4 (6)
C9—C10—H10	119.2	C25—C24—H24	119.8
C10—C11—C12	120.0 (6)	C23—C24—H24	119.8
C10—C11—H11	120.0	C24—C25—C26	119.8 (6)
C12—C11—H11	120.0	C24—C25—H25	120.1
C11—C12—C13	119.2 (6)	C26—C25—H25	120.1
C11—C12—H12	120.4	C21—C26—C25	120.7 (6)
C13—C12—H12	120.4	C21—C26—H26	119.6
C8—C13—C12	120.4 (5)	C25—C26—H26	119.6

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S1i	0.93	2.86	3.604 (5)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯S1i	0.93	2.86	3.604 (5)	137

Symmetry code: (i) .