supplementary materials


Acta Cryst. (2009). E65, m1089    [ doi:10.1107/S1600536809032048 ]

Bis(2-cyclohexyliminomethyl-4,6-disulfanylphenolato)zinc(II)

W. Chen, D. Xu, L. Liu and Q.-F. Zeng

Abstract top

In the title complex, [Zn(C13H16NOS2)2], the ZnII ion is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a distorted trans-ZnN2O2 square-planar geometry for the metal ion.

Comment top

There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2008; Xu et al., 2009). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Zn(II) is four-coordinated in a distort square-planar configuration by two N atoms and two O atoms of the Schiff base ligand (Table 1).

Related literature top

For background to Schiff bases as ligands, see: Shi et al. (2008); Xu et al. (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of 2-hydroxy-3,5-disulfanylbenzaldehyde (372 mg, 2 mmol), cyclohexanamine (198 mg, 2 mmol) and ZnCl2 (1 mmol, 134 mg) in methanol (10 ml) was stirred for 1 h. After keeping the filtrate in air for 7 d, colourless blocks of (I) were formed.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93–0.97 Å, S—H = 1.20Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
Bis(2-cyclohexyliminomethyl-4,6-disulfanylphenolato)zinc(II) top
Crystal data top
[Zn(C13H16NOS2)2]F(000) = 1248
Mr = 598.15Dx = 1.473 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 15.031 (4) Åθ = 9–12°
b = 12.663 (3) ŵ = 1.25 mm1
c = 14.182 (4) ÅT = 296 K
β = 91.735 (15)°Block, colourless
V = 2698.1 (11) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
3839 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
graphiteθmax = 25.0°, θmin = 2.1°
ω/2θ scansh = 1711
Absorption correction: ψ scan
(North et al., 1968)
k = 1514
Tmin = 0.706, Tmax = 0.789l = 1616
14026 measured reflections3 standard reflections every 200 reflections
4746 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0766P)2 + 2.9389P]
where P = (Fo2 + 2Fc2)/3
4746 reflections(Δ/σ)max = 0.013
320 parametersΔρmax = 0.58 e Å3
6 restraintsΔρmin = 0.56 e Å3
Crystal data top
[Zn(C13H16NOS2)2]V = 2698.1 (11) Å3
Mr = 598.15Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.031 (4) ŵ = 1.25 mm1
b = 12.663 (3) ÅT = 296 K
c = 14.182 (4) Å0.30 × 0.20 × 0.20 mm
β = 91.735 (15)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
3839 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.027
Tmin = 0.706, Tmax = 0.789θmax = 25.0°
14026 measured reflections3 standard reflections every 200 reflections
4746 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.141Δρmax = 0.58 e Å3
S = 1.03Δρmin = 0.56 e Å3
4746 reflectionsAbsolute structure: ?
320 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C80.8408 (2)0.3618 (3)0.5588 (2)0.0389 (8)
C100.6332 (2)0.2572 (3)0.8300 (3)0.0393 (8)
H100.61500.30680.78000.047*
C110.6548 (2)0.0326 (3)0.7702 (2)0.0389 (8)
C120.7190 (2)0.0464 (3)0.6999 (3)0.0399 (8)
C130.6325 (2)0.0695 (3)0.8077 (3)0.0407 (8)
H130.59070.07040.85480.049*
C140.7450 (3)0.5405 (3)0.5026 (3)0.0465 (9)
H140.71340.60070.48450.056*
C150.7538 (2)0.3763 (3)0.5942 (2)0.0390 (8)
C160.6116 (3)0.1202 (3)0.8080 (3)0.0457 (9)
H160.56970.11030.85420.055*
C170.5281 (3)0.3530 (4)0.9314 (3)0.0577 (11)
H17A0.51010.39750.87860.069*
H17B0.47780.34590.97220.069*
C180.6302 (3)0.2196 (3)0.7780 (3)0.0480 (9)
C190.8761 (3)0.4349 (3)0.4953 (3)0.0472 (9)
H190.93250.42390.47170.057*
C200.7118 (3)0.3063 (3)0.8838 (3)0.0481 (9)
H20A0.76070.31610.84160.058*
H20B0.73170.25910.93400.058*
C210.7095 (2)0.4694 (3)0.5638 (3)0.0424 (8)
C220.5545 (2)0.2448 (3)0.8952 (3)0.0464 (9)
H22A0.50460.21280.86090.056*
H22B0.57100.19920.94780.056*
C230.6903 (3)0.2364 (3)0.7077 (3)0.0520 (10)
H230.70200.30440.68660.062*
C240.8283 (3)0.5214 (3)0.4682 (3)0.0501 (10)
C250.8969 (2)0.2760 (3)0.5893 (3)0.0460 (9)
H250.95460.27600.56750.055*
C260.7325 (3)0.1511 (3)0.6696 (3)0.0497 (9)
C290.6047 (3)0.4040 (4)0.9854 (3)0.0651 (12)
H29A0.61910.36261.04140.078*
H29B0.58720.47401.00560.078*
C310.9466 (3)0.1246 (3)0.6765 (4)0.0587 (11)
H310.91640.06170.69990.070*
C320.6862 (3)0.4125 (3)0.9258 (3)0.0644 (12)
H32A0.73560.43930.96430.077*
H32B0.67450.46260.87510.077*
C330.9997 (4)0.1702 (4)0.7576 (4)0.0823 (16)
H33A0.96010.18950.80750.099*
H33B1.02980.23370.73720.099*
C341.1256 (3)0.0495 (5)0.7212 (4)0.0892 (17)
H34A1.16370.00580.74710.107*
H34B1.16340.10600.69940.107*
C351.0070 (4)0.0888 (6)0.6008 (4)0.107 (2)
H35A1.03920.14890.57670.129*
H35B0.97200.05830.54910.129*
C361.0692 (4)0.0900 (5)0.7957 (4)0.102 (2)
H36A1.10640.12370.84400.122*
H36B1.03870.03150.82470.122*
C371.0730 (5)0.0069 (6)0.6402 (5)0.124 (3)
H37A1.04070.05520.66000.149*
H37B1.11280.01430.59110.149*
N10.66375 (19)0.1590 (2)0.7834 (2)0.0378 (6)
N20.87612 (19)0.1999 (2)0.6432 (2)0.0453 (7)
O10.71582 (17)0.31273 (19)0.65115 (19)0.0460 (6)
O20.76509 (17)0.02931 (19)0.66432 (19)0.0481 (6)
S10.57697 (10)0.32763 (9)0.82770 (9)0.0706 (4)
H10.60380.33930.90760.106*
S20.80792 (11)0.17094 (9)0.58054 (12)0.0845 (5)
H20.76810.18530.50700.127*
S30.87207 (8)0.61165 (11)0.38901 (9)0.0714 (4)
H30.88130.56940.31420.107*
S40.60444 (7)0.49280 (9)0.60717 (10)0.0643 (3)
H40.58420.42150.65800.096*
Zn10.75466 (3)0.17547 (3)0.68717 (3)0.04322 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C80.0371 (19)0.0402 (19)0.0397 (18)0.0044 (15)0.0040 (14)0.0043 (15)
C100.0411 (19)0.0360 (18)0.0413 (18)0.0088 (15)0.0077 (15)0.0006 (15)
C110.0378 (18)0.0349 (18)0.0438 (19)0.0001 (14)0.0010 (15)0.0021 (15)
C120.0380 (18)0.0345 (18)0.047 (2)0.0001 (14)0.0005 (15)0.0001 (15)
C130.0380 (19)0.042 (2)0.0429 (19)0.0027 (15)0.0079 (15)0.0031 (15)
C140.050 (2)0.042 (2)0.048 (2)0.0052 (16)0.0065 (17)0.0066 (17)
C150.043 (2)0.0346 (18)0.0392 (18)0.0041 (15)0.0018 (15)0.0030 (15)
C160.044 (2)0.045 (2)0.049 (2)0.0040 (16)0.0066 (16)0.0029 (17)
C170.053 (2)0.062 (3)0.059 (3)0.018 (2)0.014 (2)0.006 (2)
C180.053 (2)0.038 (2)0.053 (2)0.0064 (17)0.0002 (18)0.0067 (17)
C190.043 (2)0.052 (2)0.046 (2)0.0131 (17)0.0055 (16)0.0000 (17)
C200.045 (2)0.043 (2)0.056 (2)0.0041 (16)0.0034 (17)0.0026 (18)
C210.044 (2)0.0377 (19)0.046 (2)0.0011 (15)0.0013 (16)0.0031 (16)
C220.040 (2)0.050 (2)0.050 (2)0.0032 (16)0.0093 (16)0.0022 (17)
C230.059 (2)0.032 (2)0.064 (3)0.0017 (17)0.001 (2)0.0028 (18)
C240.054 (2)0.052 (2)0.043 (2)0.0160 (18)0.0063 (17)0.0120 (18)
C250.0343 (19)0.043 (2)0.061 (2)0.0053 (16)0.0097 (16)0.0027 (18)
C260.048 (2)0.043 (2)0.058 (2)0.0019 (17)0.0101 (18)0.0048 (18)
C290.071 (3)0.063 (3)0.061 (3)0.012 (2)0.008 (2)0.021 (2)
C310.034 (2)0.041 (2)0.101 (3)0.0021 (16)0.004 (2)0.009 (2)
C320.073 (3)0.051 (3)0.070 (3)0.001 (2)0.006 (2)0.017 (2)
C330.106 (4)0.085 (4)0.055 (3)0.034 (3)0.006 (3)0.004 (3)
C340.057 (3)0.110 (5)0.100 (4)0.027 (3)0.007 (3)0.025 (4)
C350.106 (4)0.138 (5)0.077 (3)0.078 (4)0.021 (3)0.032 (3)
C360.123 (5)0.110 (5)0.070 (4)0.041 (4)0.025 (3)0.015 (3)
C370.107 (5)0.155 (7)0.108 (5)0.093 (5)0.032 (4)0.044 (5)
N10.0361 (15)0.0359 (16)0.0417 (16)0.0047 (12)0.0059 (12)0.0004 (13)
N20.0348 (16)0.0352 (16)0.066 (2)0.0015 (12)0.0069 (14)0.0013 (15)
O10.0450 (14)0.0365 (13)0.0574 (16)0.0053 (11)0.0188 (12)0.0088 (12)
O20.0472 (14)0.0342 (13)0.0639 (16)0.0003 (11)0.0191 (12)0.0018 (12)
S10.0982 (10)0.0420 (6)0.0725 (8)0.0164 (6)0.0176 (7)0.0121 (5)
S20.1057 (11)0.0464 (7)0.1048 (11)0.0007 (6)0.0616 (9)0.0149 (6)
S30.0696 (8)0.0765 (8)0.0678 (7)0.0230 (6)0.0010 (6)0.0353 (6)
S40.0503 (6)0.0478 (6)0.0960 (9)0.0140 (5)0.0214 (6)0.0098 (6)
Zn10.0413 (3)0.0359 (3)0.0531 (3)0.00146 (17)0.01108 (19)0.00153 (18)
Geometric parameters (Å, °) top
C8—C191.408 (5)C23—H230.9300
C8—C151.426 (5)C24—S31.745 (4)
C8—C251.434 (5)C25—N21.275 (5)
C10—N11.488 (4)C25—H250.9300
C10—C201.520 (5)C26—S21.741 (4)
C10—C221.532 (5)C29—C321.513 (6)
C10—H100.9800C29—H29A0.9700
C11—C161.400 (5)C29—H29B0.9700
C11—C121.419 (5)C31—N21.491 (5)
C11—C131.441 (5)C31—C331.496 (7)
C12—O21.295 (4)C31—C351.497 (7)
C12—C261.410 (5)C31—H310.9800
C13—N11.278 (4)C32—H32A0.9700
C13—H130.9300C32—H32B0.9700
C14—C211.370 (5)C33—C361.542 (7)
C14—C241.379 (6)C33—H33A0.9700
C14—H140.9300C33—H33B0.9700
C15—O11.286 (4)C34—C361.467 (8)
C15—C211.415 (5)C34—C371.476 (9)
C16—C181.361 (5)C34—H34A0.9700
C16—H160.9300C34—H34B0.9700
C17—C291.509 (6)C35—C371.530 (7)
C17—C221.519 (5)C35—H35A0.9700
C17—H17A0.9700C35—H35B0.9700
C17—H17B0.9700C36—H36A0.9700
C18—C231.382 (6)C36—H36B0.9700
C18—S11.745 (4)C37—H37A0.9700
C19—C241.359 (6)C37—H37B0.9700
C19—H190.9300Zn1—N11.971 (3)
C20—C321.525 (5)Zn1—N21.971 (3)
C20—H20A0.9700Zn1—O11.899 (2)
C20—H20B0.9700Zn1—O21.886 (2)
C21—S41.737 (4)S1—H11.2000
C22—H22A0.9700S2—H21.2000
C22—H22B0.9700S3—H31.2000
C23—C261.371 (6)S4—H41.2000
C19—C8—C15120.5 (3)C17—C29—C32111.4 (4)
C19—C8—C25117.5 (3)C17—C29—H29A109.4
C15—C8—C25121.9 (3)C32—C29—H29A109.4
N1—C10—C20108.7 (3)C17—C29—H29B109.4
N1—C10—C22115.9 (3)C32—C29—H29B109.4
C20—C10—C22110.0 (3)H29A—C29—H29B108.0
N1—C10—H10107.3N2—C31—C33110.7 (4)
C20—C10—H10107.3N2—C31—C35114.0 (4)
C22—C10—H10107.3C33—C31—C35110.3 (4)
C16—C11—C12120.3 (3)N2—C31—H31107.2
C16—C11—C13117.0 (3)C33—C31—H31107.2
C12—C11—C13122.7 (3)C35—C31—H31107.2
O2—C12—C26119.6 (3)C29—C32—C20111.9 (4)
O2—C12—C11124.5 (3)C29—C32—H32A109.2
C26—C12—C11115.9 (3)C20—C32—H32A109.2
N1—C13—C11127.1 (3)C29—C32—H32B109.2
N1—C13—H13116.4C20—C32—H32B109.2
C11—C13—H13116.4H32A—C32—H32B107.9
C21—C14—C24118.9 (4)C31—C33—C36110.8 (4)
C21—C14—H14120.5C31—C33—H33A109.5
C24—C14—H14120.5C36—C33—H33A109.5
O1—C15—C21119.9 (3)C31—C33—H33B109.5
O1—C15—C8124.7 (3)C36—C33—H33B109.5
C21—C15—C8115.4 (3)H33A—C33—H33B108.1
C18—C16—C11120.7 (3)C36—C34—C37112.4 (5)
C18—C16—H16119.7C36—C34—H34A109.1
C11—C16—H16119.7C37—C34—H34A109.1
C29—C17—C22110.8 (3)C36—C34—H34B109.1
C29—C17—H17A109.5C37—C34—H34B109.1
C22—C17—H17A109.5H34A—C34—H34B107.9
C29—C17—H17B109.5C31—C35—C37110.1 (5)
C22—C17—H17B109.5C31—C35—H35A109.6
H17A—C17—H17B108.1C37—C35—H35A109.6
C16—C18—C23120.9 (4)C31—C35—H35B109.6
C16—C18—S1119.9 (3)C37—C35—H35B109.6
C23—C18—S1119.2 (3)H35A—C35—H35B108.2
C24—C19—C8120.3 (4)C34—C36—C33112.2 (4)
C24—C19—H19119.9C34—C36—H36A109.2
C8—C19—H19119.9C33—C36—H36A109.2
C10—C20—C32110.8 (3)C34—C36—H36B109.2
C10—C20—H20A109.5C33—C36—H36B109.2
C32—C20—H20A109.5H36A—C36—H36B107.9
C10—C20—H20B109.5C34—C37—C35111.2 (5)
C32—C20—H20B109.5C34—C37—H37A109.4
H20A—C20—H20B108.1C35—C37—H37A109.4
C14—C21—C15123.5 (3)C34—C37—H37B109.4
C14—C21—S4119.2 (3)C35—C37—H37B109.4
C15—C21—S4117.3 (3)H37A—C37—H37B108.0
C17—C22—C10109.0 (3)C13—N1—C10120.0 (3)
C17—C22—H22A109.9C13—N1—Zn1123.3 (2)
C10—C22—H22A109.9C10—N1—Zn1116.7 (2)
C17—C22—H22B109.9C25—N2—C31119.3 (3)
C10—C22—H22B109.9C25—N2—Zn1123.6 (3)
H22A—C22—H22B108.3C31—N2—Zn1117.1 (2)
C26—C23—C18118.9 (4)C15—O1—Zn1127.1 (2)
C26—C23—H23120.5C12—O2—Zn1127.7 (2)
C18—C23—H23120.5C18—S1—H1109.5
C19—C24—C14121.3 (4)C26—S2—H2109.5
C19—C24—S3120.2 (3)C24—S3—H3109.5
C14—C24—S3118.5 (3)C21—S4—H4109.5
N2—C25—C8127.0 (3)O2—Zn1—O1151.46 (13)
N2—C25—H25116.5O2—Zn1—N194.46 (11)
C8—C25—H25116.5O1—Zn1—N193.98 (11)
C23—C26—C12123.2 (4)O2—Zn1—N290.96 (12)
C23—C26—S2119.4 (3)O1—Zn1—N292.96 (12)
C12—C26—S2117.4 (3)N1—Zn1—N2154.63 (14)
Table 1
Selected geometric parameters (Å, °)
top
Zn1—N11.971 (3)Zn1—O11.899 (2)
Zn1—N21.971 (3)Zn1—O21.886 (2)
O2—Zn1—O1151.46 (13)O2—Zn1—N290.96 (12)
O2—Zn1—N194.46 (11)O1—Zn1—N292.96 (12)
O1—Zn1—N193.98 (11)N1—Zn1—N2154.63 (14)
references
References top

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