4-Bromo-2-[(E)-(2-{2-[(2-{[(E)-5-bromo-2-hy-droxy-benzyl-idene]amino}-phen-yl)sulfan-yl]ethyl-sulfan-yl}phen-yl)imino-meth-yl]phenol.

The asymmetric unit of the title compound, C(28)H(22)Br(2)N(2)O(2)S(2), comprises half of a Schiff base ligand, the whole mol-ecule being generated by a crystallographic inversion center located at the mid-point of the C-C bond of the central methyl-ene segment. Intra-molecular O-H⋯N and O-H⋯S hydrogen bonds make S(6) and S(5) ring motifs, respectively. In the crystal, there are no significant inter-molecular inter-actions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff base ligands see, for example: Kargar et al. (2011 ▶); Kia et al. (2010 ▶).

Experimental

Crystal data

C28H22Br2N2O2S2

M = 642.42

Monoclinic,

a = 13.9124 (18) Å

b = 5.4112 (7) Å

c = 17.409 (2) Å

β = 92.444 (7)°

V = 1309.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.28 mm−1

T = 296 K

0.35 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.393, T max = 0.694

10754 measured reflections

2879 independent reflections

1277 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.106

S = 0.93

2879 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034071/su2486sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034071/su2486Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034071/su2486Isup3.cml

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

C28H22Br2N2O2S2	F(000) = 644
Mr = 642.42	Dx = 1.629 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2098 reflections
a = 13.9124 (18) Å	θ = 2.5–28.8°
b = 5.4112 (7) Å	µ = 3.28 mm−1
c = 17.409 (2) Å	T = 296 K
β = 92.444 (7)°	Needle, light-yellow
V = 1309.4 (3) Å3	0.35 × 0.14 × 0.12 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	2879 independent reflections
Radiation source: fine-focus sealed tube	1277 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
φ and ω scans	θmax = 27.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.393, Tmax = 0.694	k = −6→4
10754 measured reflections	l = −22→22

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0347P)2] where P = (Fo2 + 2Fc2)/3
2879 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.55 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
Br1	0.55873 (4)	1.84843 (11)	0.63714 (3)	0.0707 (3)
S1	0.08346 (11)	0.7463 (2)	0.57293 (8)	0.0622 (4)
O1	0.2265 (3)	1.2258 (6)	0.51696 (19)	0.0684 (11)
H1	0.2092	1.1303	0.5566	0.103*
N1	0.2327 (3)	0.9977 (8)	0.6512 (2)	0.0479 (10)
C1	0.2994 (4)	1.3675 (9)	0.5463 (3)	0.0502 (13)
C2	0.3336 (4)	1.5574 (10)	0.5026 (3)	0.0633 (16)
H2	0.3048	1.5889	0.4544	0.076*
C3	0.4094 (4)	1.7013 (9)	0.5286 (3)	0.0577 (15)
H3	0.4322	1.8277	0.4981	0.069*
C4	0.4522 (3)	1.6562 (9)	0.6015 (3)	0.0492 (13)
C5	0.4185 (3)	1.4704 (9)	0.6453 (3)	0.0483 (13)
H5	0.4480	1.4404	0.6934	0.058*
C6	0.3408 (3)	1.3230 (8)	0.6206 (2)	0.0439 (12)
C7	0.3043 (4)	1.1325 (9)	0.6696 (3)	0.0510 (13)
H7	0.3352	1.1076	0.7174	0.061*
C8	0.1967 (3)	0.8149 (9)	0.7006 (3)	0.0436 (12)
C9	0.2299 (4)	0.7718 (10)	0.7752 (3)	0.0672 (16)
H9	0.2797	0.8671	0.7968	0.081*
C10	0.1892 (4)	0.5876 (10)	0.8175 (3)	0.0692 (17)
H10	0.2109	0.5615	0.8681	0.083*
C11	0.1171 (4)	0.4423 (10)	0.7861 (3)	0.0616 (15)
H11	0.0911	0.3157	0.8148	0.074*
C12	0.0836 (4)	0.4857 (10)	0.7114 (3)	0.0595 (15)
H12	0.0338	0.3893	0.6903	0.071*
C13	0.1228 (3)	0.6697 (9)	0.6678 (3)	0.0447 (12)
C14	0.0071 (4)	0.4938 (9)	0.5431 (2)	0.0567 (14)
H14A	0.0368	0.3379	0.5582	0.068*
H14B	−0.0543	0.5063	0.5671	0.068*

	U11	U22	U33	U12	U13	U23
Br1	0.0767 (5)	0.0794 (5)	0.0547 (4)	−0.0273 (3)	−0.0120 (3)	0.0093 (3)
S1	0.0652 (11)	0.0659 (11)	0.0537 (9)	−0.0180 (7)	−0.0170 (7)	−0.0023 (7)
O1	0.059 (3)	0.091 (3)	0.053 (2)	−0.020 (2)	−0.0163 (19)	0.0036 (18)
N1	0.042 (3)	0.054 (3)	0.047 (2)	−0.011 (2)	−0.006 (2)	−0.007 (2)
C1	0.049 (3)	0.059 (4)	0.042 (3)	0.000 (3)	−0.008 (2)	−0.008 (3)
C2	0.060 (4)	0.085 (5)	0.043 (3)	0.002 (3)	−0.014 (3)	0.016 (3)
C3	0.060 (4)	0.070 (4)	0.042 (3)	−0.008 (3)	−0.008 (3)	0.010 (3)
C4	0.048 (3)	0.057 (4)	0.042 (3)	−0.009 (3)	0.001 (2)	−0.003 (3)
C5	0.046 (4)	0.060 (4)	0.038 (3)	−0.007 (3)	−0.009 (2)	0.003 (3)
C6	0.042 (3)	0.052 (4)	0.037 (3)	0.001 (3)	−0.001 (2)	0.003 (3)
C7	0.056 (4)	0.057 (4)	0.039 (3)	−0.007 (3)	−0.006 (3)	0.003 (3)
C8	0.039 (3)	0.047 (4)	0.045 (3)	−0.008 (3)	0.001 (2)	−0.001 (3)
C9	0.064 (4)	0.084 (5)	0.052 (4)	−0.023 (3)	−0.009 (3)	0.007 (3)
C10	0.068 (5)	0.083 (5)	0.056 (4)	−0.011 (3)	−0.002 (3)	0.013 (3)
C11	0.060 (4)	0.061 (4)	0.064 (4)	−0.008 (3)	0.004 (3)	0.013 (3)
C12	0.048 (4)	0.067 (4)	0.062 (4)	−0.014 (3)	−0.007 (3)	0.001 (3)
C13	0.036 (3)	0.047 (3)	0.051 (3)	0.003 (3)	−0.002 (2)	0.000 (3)
C14	0.048 (3)	0.060 (4)	0.062 (3)	−0.009 (3)	−0.003 (3)	−0.005 (3)

Br1—C4	1.894 (5)	C6—C7	1.444 (6)
S1—C13	1.766 (5)	C7—H7	0.9300
S1—C14	1.793 (5)	C8—C9	1.379 (6)
O1—C1	1.354 (5)	C8—C13	1.397 (6)
O1—H1	0.9026	C9—C10	1.376 (6)
N1—C7	1.265 (5)	C9—H9	0.9300
N1—C8	1.416 (5)	C10—C11	1.369 (7)
C1—C2	1.377 (6)	C10—H10	0.9300
C1—C6	1.413 (6)	C11—C12	1.383 (6)
C2—C3	1.373 (6)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.379 (6)
C3—C4	1.399 (6)	C12—H12	0.9300
C3—H3	0.9300	C14—C14i	1.508 (8)
C4—C5	1.358 (6)	C14—H14A	0.9700
C5—C6	1.396 (6)	C14—H14B	0.9700
C5—H5	0.9300
C13—S1—C14	104.3 (2)	C9—C8—C13	120.1 (5)
C1—O1—H1	104.8	C9—C8—N1	125.2 (5)
C7—N1—C8	123.0 (4)	C13—C8—N1	114.7 (4)
O1—C1—C2	119.0 (4)	C10—C9—C8	119.8 (5)
O1—C1—C6	121.3 (5)	C10—C9—H9	120.1
C2—C1—C6	119.7 (5)	C8—C9—H9	120.1
C3—C2—C1	121.3 (5)	C11—C10—C9	120.9 (5)
C3—C2—H2	119.3	C11—C10—H10	119.5
C1—C2—H2	119.3	C9—C10—H10	119.5
C2—C3—C4	119.4 (5)	C10—C11—C12	119.3 (5)
C2—C3—H3	120.3	C10—C11—H11	120.3
C4—C3—H3	120.3	C12—C11—H11	120.3
C5—C4—C3	119.7 (5)	C13—C12—C11	121.0 (5)
C5—C4—Br1	120.4 (4)	C13—C12—H12	119.5
C3—C4—Br1	119.9 (4)	C11—C12—H12	119.5
C4—C5—C6	122.0 (4)	C12—C13—C8	118.8 (4)
C4—C5—H5	119.0	C12—C13—S1	124.8 (4)
C6—C5—H5	119.0	C8—C13—S1	116.3 (4)
C5—C6—C1	117.7 (4)	C14i—C14—S1	107.8 (4)
C5—C6—C7	120.8 (4)	C14i—C14—H14A	110.2
C1—C6—C7	121.5 (4)	S1—C14—H14A	110.2
N1—C7—C6	123.7 (5)	C14i—C14—H14B	110.2
N1—C7—H7	118.1	S1—C14—H14B	110.2
C6—C7—H7	118.1	H14A—C14—H14B	108.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90	1.81	2.641 (5)	151
O1—H1···S1	0.90	2.74	3.436 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90	1.81	2.641 (5)	151
O1—H1⋯S1	0.90	2.74	3.436 (4)	135