2,2′-[(Disulfanediyl)bis{5-[(1E)-(2-hy­droxy­benzyl­idene)amino]-1,3-thia­zole-4,2-di­yl}]diphenol: synthesis, crystal structure and calculation of molecular hyperpolarizability

The title Schiff base compound {systematic name: 2-[5-[(E)-(2-hy­droxy­benzyl­idene)amino]-4-(2-{5-[(E)-(2-hy­droxy­benzyl­idene)amino]-2-(2-hy­droxy­phen­yl)-1,3-thia­zol-4-yl}disulfan­yl)-1,3-thia­zol-2-yl]phenol}, C₃₂H₂₂N₄O₄S₄, incorporating a disulfanediyl (di­thio) linkage, was obtained from the condensation reaction between two equivalents of salicyl­aldehyde and one equivalent of di­thio­oxamide in di­methyl­formamide, and was characterized by elemental analysis, IR spectroscopic analysis and single-crystal X-ray diffraction. A one-dimensional chain is formed along the b axis via double inter­molecular C—H...S hydrogen bonds. The HOMO (highest occupied mol­ecular orbital) and LUMO (lowest unoccupied mol­ecular orbital) energies and some related mol­ecular parameters were calculated at the B3LYP/6-311G(d,p) level of theory. The molecular hyperpolarizability was also calculated.

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: XPW (Siemens, 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).

2-[5-[(E)-(2-Hydroxybenzylidene)amino]-4-(2-{5-[(E)-(2-hydroxybenzylidene)amino]-2-(2-hydroxyphenyl)-1,3-thiazol-4-yl}disulfanyl)-1,3-thiazol-2-yl]phenol

Crystal data

C32H22N4O4S4	F(000) = 676
Mr = 654.77	Dx = 1.463 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1813 (7) Å	Cell parameters from 7100 reflections
b = 7.2661 (4) Å	θ = 2.6–26.0°
c = 15.6283 (8) Å	µ = 0.37 mm^−1
β = 96.933 (3)°	T = 298 K
V = 1485.88 (14) Å^3	Irregular, brown
Z = 2	0.23 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	2127 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.052
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.0°, θmin = 2.6°
Tmin = 0.647, Tmax = 0.745	h = −16→16
46264 measured reflections	k = −8→8
2918 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0712P)^2 + 0.3626P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
2918 reflections	Δρmax = 0.37 e Å^−3
207 parameters	Δρmin = −0.23 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.51227 (4)	0.27182 (8)	0.40014 (4)	0.0504 (2)
S2	0.45256 (5)	−0.26435 (9)	0.29971 (5)	0.0680 (3)
O1	0.20486 (15)	−0.0275 (3)	0.18068 (13)	0.0707 (5)
C1	0.60088 (16)	0.1073 (3)	0.44137 (14)	0.0476 (5)
C2	0.68782 (17)	0.1542 (3)	0.50469 (14)	0.0486 (5)
C3	0.71056 (19)	0.3356 (4)	0.52755 (15)	0.0581 (6)
H3	0.670628	0.429445	0.500667	0.070*
C4	0.7905 (2)	0.3802 (4)	0.58887 (17)	0.0695 (7)
H4	0.804961	0.502434	0.603168	0.083*
C5	0.8494 (2)	0.2387 (5)	0.62913 (18)	0.0724 (8)
H5	0.902945	0.266913	0.671441	0.087*
C6	0.82965 (19)	0.0594 (4)	0.60741 (16)	0.0664 (7)
H6	0.869725	−0.033344	0.635078	0.080*
C7	0.75044 (18)	0.0143 (4)	0.54450 (15)	0.0554 (6)
O2	0.73547 (15)	−0.1661 (3)	0.52538 (14)	0.0717 (6)
N1	0.58145 (14)	−0.0592 (3)	0.41213 (12)	0.0527 (5)
C8	0.49473 (18)	−0.0641 (3)	0.35449 (15)	0.0509 (6)
C9	0.44575 (16)	0.1005 (3)	0.33905 (14)	0.0469 (5)
N2	0.35841 (14)	0.1230 (3)	0.28175 (12)	0.0494 (5)
C10	0.31827 (17)	0.2798 (3)	0.26292 (15)	0.0509 (6)
H10	0.349447	0.384448	0.288246	0.061*
C11	0.22652 (17)	0.3003 (3)	0.20390 (15)	0.0506 (6)
C12	0.17275 (18)	0.1465 (4)	0.16608 (15)	0.0551 (6)
C13	0.0829 (2)	0.1748 (5)	0.11118 (17)	0.0744 (8)
H13	0.046400	0.074815	0.086368	0.089*
C14	0.0483 (2)	0.3503 (6)	0.09371 (19)	0.0872 (10)
H14	−0.012374	0.367658	0.057622	0.105*
C15	0.1012 (2)	0.5014 (5)	0.1283 (2)	0.0884 (10)
H15	0.077111	0.619459	0.114700	0.106*
C16	0.1895 (2)	0.4769 (4)	0.18286 (17)	0.0687 (7)
H16	0.225294	0.578972	0.206231	0.082*
H1	0.266 (2)	−0.023 (4)	0.2164 (19)	0.096 (11)*
H2	0.688 (3)	−0.178 (5)	0.481 (2)	0.112 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0485 (3)	0.0457 (4)	0.0547 (4)	0.0055 (3)	−0.0040 (3)	0.0009 (3)
S2	0.0691 (5)	0.0375 (4)	0.0913 (5)	−0.0119 (3)	−0.0152 (4)	0.0110 (3)
O1	0.0663 (12)	0.0606 (13)	0.0809 (13)	−0.0114 (9)	−0.0092 (10)	0.0013 (10)
C1	0.0459 (12)	0.0463 (13)	0.0500 (12)	0.0029 (10)	0.0030 (10)	0.0083 (10)
C2	0.0422 (12)	0.0549 (14)	0.0480 (12)	0.0016 (10)	0.0021 (10)	0.0051 (11)
C3	0.0534 (14)	0.0624 (16)	0.0571 (14)	0.0005 (12)	0.0015 (11)	0.0016 (12)
C4	0.0641 (17)	0.076 (2)	0.0673 (16)	−0.0113 (15)	0.0021 (14)	−0.0085 (15)
C5	0.0548 (16)	0.102 (3)	0.0584 (16)	−0.0099 (16)	−0.0037 (12)	−0.0016 (16)
C6	0.0478 (14)	0.089 (2)	0.0604 (15)	0.0054 (14)	−0.0022 (12)	0.0152 (15)
C7	0.0465 (13)	0.0662 (17)	0.0529 (13)	0.0019 (12)	0.0032 (11)	0.0107 (12)
O2	0.0712 (13)	0.0596 (13)	0.0789 (13)	0.0112 (10)	−0.0131 (11)	0.0110 (10)
N1	0.0509 (11)	0.0460 (12)	0.0583 (11)	−0.0002 (9)	−0.0052 (9)	0.0132 (9)
C8	0.0522 (13)	0.0406 (13)	0.0577 (14)	−0.0050 (10)	−0.0024 (11)	0.0105 (10)
C9	0.0433 (12)	0.0463 (13)	0.0502 (13)	−0.0014 (10)	0.0022 (10)	0.0083 (10)
N2	0.0445 (10)	0.0500 (12)	0.0522 (11)	−0.0007 (9)	0.0006 (8)	0.0051 (9)
C10	0.0479 (13)	0.0477 (14)	0.0549 (13)	0.0016 (10)	−0.0021 (10)	−0.0019 (11)
C11	0.0452 (13)	0.0565 (15)	0.0488 (12)	0.0065 (11)	0.0004 (10)	−0.0039 (11)
C12	0.0447 (13)	0.0657 (17)	0.0545 (13)	0.0013 (12)	0.0040 (11)	0.0015 (12)
C13	0.0485 (15)	0.106 (2)	0.0659 (16)	−0.0086 (16)	−0.0055 (13)	−0.0053 (17)
C14	0.0565 (17)	0.126 (3)	0.0732 (19)	0.0256 (19)	−0.0144 (14)	0.004 (2)
C15	0.082 (2)	0.091 (2)	0.087 (2)	0.0381 (19)	−0.0138 (17)	0.0023 (18)
C16	0.0686 (17)	0.0658 (18)	0.0677 (16)	0.0206 (14)	−0.0088 (13)	−0.0037 (14)

Geometric parameters (Å, º)

N2—C10	1.275 (3)	C4—H4	0.9300
C1—N1	1.307 (3)	C5—C6	1.364 (4)
C8—C9	1.366 (3)	C5—H5	0.9300
C10—C11	1.437 (3)	C6—C7	1.384 (3)
S1—C1	1.740 (2)	C6—H6	0.9300
S2—S2^i	2.1089 (16)	C7—O2	1.354 (3)
C9—N2	1.380 (3)	O2—H2	0.88 (4)
N1—C8	1.368 (3)	C10—H10	0.9300
C1—C2	1.461 (3)	C11—C16	1.398 (4)
S1—C9	1.740 (2)	C11—C12	1.414 (3)
S2—C8	1.745 (2)	C12—C13	1.391 (3)
O1—C12	1.344 (3)	C13—C14	1.371 (5)
O1—H1	0.92 (3)	C13—H13	0.9300
C2—C3	1.389 (4)	C14—C15	1.376 (5)
C2—C7	1.406 (3)	C14—H14	0.9300
C3—C4	1.375 (3)	C15—C16	1.369 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.392 (4)	C16—H16	0.9300
N2—C10—C11	122.3 (2)	O2—C7—C6	117.6 (2)
C9—C8—S2	121.82 (18)	O2—C7—C2	122.7 (2)
N2—C9—S1	126.64 (17)	C6—C7—C2	119.7 (3)
N1—C1—S1	114.32 (17)	C7—O2—H2	110 (3)
N1—C1—C2	123.9 (2)	C9—C8—N1	115.7 (2)
C8—S2—S2^i	100.33 (8)	C8—C9—N2	123.9 (2)
C10—N2—C9	123.1 (2)	C8—C9—S1	109.45 (17)
N1—C8—S2	122.42 (18)	N2—C10—H10	118.9
C9—S1—C1	89.02 (11)	C11—C10—H10	118.9
C1—N1—C8	111.53 (19)	C16—C11—C12	118.9 (2)
C2—C1—S1	121.81 (18)	C16—C11—C10	119.3 (2)
C12—O1—H1	108 (2)	C12—C11—C10	121.8 (2)
C3—C2—C7	118.4 (2)	O1—C12—C13	118.1 (3)
C3—C2—C1	121.5 (2)	O1—C12—C11	122.7 (2)
C7—C2—C1	120.1 (2)	C13—C12—C11	119.2 (3)
C4—C3—C2	121.8 (3)	C14—C13—C12	119.9 (3)
C4—C3—H3	119.1	C14—C13—H13	120.1
C2—C3—H3	119.1	C12—C13—H13	120.1
C3—C4—C5	118.7 (3)	C13—C14—C15	121.6 (3)
C3—C4—H4	120.7	C13—C14—H14	119.2
C5—C4—H4	120.7	C15—C14—H14	119.2
C6—C5—C4	120.9 (3)	C16—C15—C14	119.5 (3)
C6—C5—H5	119.5	C16—C15—H15	120.2
C4—C5—H5	119.5	C14—C15—H15	120.2
C5—C6—C7	120.5 (3)	C15—C16—C11	120.8 (3)
C5—C6—H6	119.7	C15—C16—H16	119.6
C7—C6—H6	119.7	C11—C16—H16	119.6
S2^i—S2—C8—C9	95.8 (2)	S2^i—S2—C8—N1	−80.7 (2)
C1—C2—C7—O2	1.6 (3)	C8—N1—C1—C2	179.2 (2)
C8—N1—C1—S1	0.4 (2)	C10—N2—C9—C8	−174.2 (2)
C9—N2—C10—C11	−179.2 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.92 (3)	1.83 (3)	2.649 (3)	146 (3)
O2—H2···N1	0.88 (4)	1.87 (4)	2.644 (3)	145 (4)
C10—H10···S2^ii	0.93	2.89	3.767 (3)	158

Symmetry code: (ii) x, y+1, z.