Literature DB >> 22807795

Bis[benzyl 3-(3-phenyl-prop-2-enyl-idene)dithio-carbazato-κ(2)N(3),S]cadmium.

M S Reza, M A A A A Islam, M T H Tarafder, M C Sheikh, E Zangrando.   

Abstract

In the title complex, [Cd(C(17)H(15)N(2)S(2))(2)], the Cd(II) ion is located on a twofold rotation axis and exhibits a coordination number of four within a very distorted coordination environment that is best described as bis-phenoidal. The two deprotonated Schiff base ligands chelate the Cd(II) ion through the azomethine N and the thiol-ate S atom. The dihedral angle between the two chelating ligands is 84.01 (9)°. Weak inter-molecular C-H⋯S inter-actions lead to the formation of chains along the c axis.

Entities:  

Year:  2012        PMID： 22807795      PMCID： PMC3393227          DOI： 10.1107/S1600536812028127

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the structure of uncoordinated Schiff bases, see: Tarafder, Crouse et al. (2008 ▶); Tarafder, Islam et al. (2008 ▶). For the isotypic Zn and Hg analogues, see: Fun et al. (2008 ▶); Islam et al. (2012 ▶). For the coordination behaviour of metal ions (Co, Ni, Cu, Zn, Cd and Hg) with the cinnamaldehyde Schiff base of S-methyl­dithio­carbazate, see: Liu et al. (2009 ▶); Abram et al. (2006 ▶). For the bioactivity of transition metal complexes of similar Schiff base ligands, see: Chew et al. (2004 ▶); How et al. (2008 ▶); Maia et al. (2010 ▶).

Experimental

Crystal data

[Cd(C17H15N2S2)2] M = 735.26 Orthorhombic, a = 36.2497 (7) Å b = 9.9940 (2) Å c = 8.9392 (2) Å V = 3238.49 (12) Å3 Z = 4 Cu Kα radiation μ = 8.05 mm−1 T = 173 K 0.3 × 0.3 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.325, T max = 0.448 10761 measured reflections 2964 independent reflections 2439 reflections with I > 2σ(I) R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.115 S = 1.02 2964 reflections 195 parameters H-atom parameters constrained Δρmax = 1.36 e Å−3 Δρmin = −0.52 e Å−3 Data collection: RAPID-AUTO (Rigaku, 1995 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028127/wm2651sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028127/wm2651Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cd(C17H15N2S2)2]F(000) = 1496
Mr = 735.26Dx = 1.508 Mg m−3
Orthorhombic, PbcnCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2n 2abCell parameters from 29242 reflections
a = 36.2497 (7) Åθ = 3.7–68.2°
b = 9.9940 (2) ŵ = 8.05 mm−1
c = 8.9392 (2) ÅT = 173 K
V = 3238.49 (12) Å3Prism, yellow
Z = 40.3 × 0.3 × 0.1 mm
Rigaku R-AXIS RAPID diffractometer2964 independent reflections
Radiation source: fine-focus sealed tube2439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
Detector resolution: 10.000 pixels mm-1θmax = 68.3°, θmin = 4.6°
ω scansh = −42→43
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)k = −11→12
Tmin = 0.325, Tmax = 0.448l = −10→10
10761 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0606P)2] where P = (Fo2 + 2Fc2)/3
2964 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 1.36 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
Cd0.50000.44301 (4)0.75000.04150 (16)
N10.52779 (6)0.2994 (3)0.9175 (3)0.0358 (6)
N20.56616 (6)0.2968 (3)0.9179 (3)0.0367 (6)
S10.56402 (2)0.50756 (11)0.71527 (10)0.0483 (3)
S20.62987 (2)0.39583 (11)0.83639 (11)0.0540 (3)
C10.51250 (9)0.2128 (3)1.0048 (3)0.0398 (7)
H10.52760.15111.05780.048*
C20.47320 (8)0.2078 (3)1.0235 (3)0.0395 (7)
H20.45870.27150.97100.047*
C30.45573 (8)0.1191 (4)1.1103 (4)0.0415 (8)
H30.47050.05261.15700.050*
C40.41607 (8)0.1147 (3)1.1403 (3)0.0381 (7)
C50.39164 (8)0.2100 (4)1.0849 (4)0.0436 (8)
H50.40070.28081.02440.052*
C60.35458 (8)0.2033 (4)1.1162 (4)0.0476 (9)
H60.33830.26951.07790.057*
C70.34086 (9)0.1000 (4)1.2038 (4)0.0511 (9)
H70.31520.09491.22430.061*
C80.36437 (11)0.0055 (5)1.2607 (4)0.0516 (10)
H80.3550−0.06431.32200.062*
C90.40186 (10)0.0116 (5)1.2288 (4)0.0455 (8)
H90.4180−0.05501.26750.055*
C100.58178 (8)0.3856 (3)0.8347 (3)0.0391 (7)
C110.64403 (8)0.2893 (4)0.9912 (4)0.0455 (8)
H11A0.63000.31181.08290.055*
H11B0.63990.19390.96680.055*
C120.68464 (8)0.3169 (3)1.0126 (3)0.0413 (8)
C130.69639 (9)0.4203 (4)1.1010 (5)0.0577 (10)
H130.67870.47471.15060.069*
C140.73377 (10)0.4472 (4)1.1193 (5)0.0619 (12)
H140.74150.51881.18180.074*
C150.75932 (9)0.3706 (4)1.0474 (4)0.0538 (10)
H150.78490.38841.05980.065*
C160.74806 (8)0.2689 (4)0.9579 (5)0.0593 (10)
H160.76590.21670.90650.071*
C170.71095 (8)0.2401 (4)0.9404 (4)0.0517 (9)
H170.70350.16750.87870.062*
U11U22U33U12U13U23
Cd0.0334 (2)0.0470 (3)0.0440 (2)0.000−0.01208 (12)0.000
N10.0262 (12)0.0447 (16)0.0365 (13)0.0008 (11)−0.0011 (10)0.0027 (12)
N20.0255 (12)0.0478 (17)0.0368 (13)0.0013 (11)0.0000 (10)0.0006 (12)
S10.0401 (5)0.0524 (6)0.0525 (5)−0.0107 (4)−0.0125 (4)0.0125 (4)
S20.0278 (4)0.0780 (7)0.0562 (5)−0.0073 (4)0.0006 (3)0.0214 (5)
C10.0286 (14)0.050 (2)0.0411 (16)0.0016 (14)−0.0024 (13)0.0023 (15)
C20.0269 (14)0.051 (2)0.0408 (16)0.0021 (14)−0.0023 (12)0.0052 (15)
C30.0308 (16)0.052 (2)0.0422 (17)0.0037 (14)−0.0054 (13)0.0017 (15)
C40.0285 (15)0.049 (2)0.0368 (16)−0.0030 (13)−0.0014 (12)−0.0023 (14)
C50.0337 (16)0.049 (2)0.0481 (18)−0.0035 (14)0.0000 (14)0.0018 (16)
C60.0289 (16)0.056 (2)0.058 (2)−0.0016 (15)−0.0051 (14)−0.0033 (18)
C70.0328 (18)0.068 (3)0.053 (2)−0.0074 (17)0.0038 (16)−0.013 (2)
C80.044 (2)0.058 (3)0.054 (2)−0.013 (2)0.0063 (14)0.0020 (17)
C90.0410 (19)0.047 (2)0.0486 (19)0.0003 (17)−0.0010 (14)0.0020 (16)
C100.0301 (15)0.049 (2)0.0382 (16)−0.0005 (14)−0.0046 (12)0.0002 (15)
C110.0256 (15)0.060 (2)0.0504 (19)0.0024 (14)0.0032 (13)0.0102 (17)
C120.0256 (15)0.055 (2)0.0438 (17)0.0007 (13)0.0037 (12)0.0050 (16)
C130.0376 (19)0.071 (3)0.065 (3)0.0062 (17)0.0113 (17)−0.014 (2)
C140.046 (2)0.075 (3)0.065 (3)−0.0093 (19)−0.0016 (18)−0.017 (2)
C150.0273 (16)0.077 (3)0.057 (2)−0.0049 (17)−0.0021 (15)0.004 (2)
C160.0286 (18)0.068 (3)0.081 (3)0.0077 (17)0.0040 (16)−0.010 (2)
C170.0330 (17)0.054 (2)0.068 (2)0.0011 (15)0.0028 (16)−0.0126 (19)
Cd—N1i2.306 (2)C6—H60.9500
Cd—N12.306 (2)C7—C81.370 (6)
Cd—S12.4285 (9)C7—H70.9500
Cd—S1i2.4285 (9)C8—C91.390 (5)
N1—C11.291 (4)C8—H80.9500
N1—N21.391 (3)C9—H90.9500
N2—C101.288 (4)C11—C121.510 (4)
S1—C101.744 (3)C11—H11A0.9900
S2—C101.746 (3)C11—H11B0.9900
S2—C111.819 (3)C12—C131.368 (5)
C1—C21.435 (4)C12—C171.384 (4)
C1—H10.9500C13—C141.391 (4)
C2—C31.337 (4)C13—H130.9500
C2—H20.9500C14—C151.362 (5)
C3—C41.463 (4)C14—H140.9500
C3—H30.9500C15—C161.356 (5)
C4—C51.392 (4)C15—H150.9500
C4—C91.398 (5)C16—C171.385 (4)
C5—C61.374 (4)C16—H160.9500
C5—H50.9500C17—H170.9500
C6—C71.388 (5)
N1i—Cd—N1103.00 (12)C7—C8—C9120.2 (4)
N1i—Cd—S1119.99 (6)C7—C8—H8119.9
N1—Cd—S180.27 (6)C9—C8—H8119.9
N1i—Cd—S1i80.27 (6)C8—C9—C4120.6 (4)
N1—Cd—S1i119.99 (6)C8—C9—H9119.7
S1—Cd—S1i149.19 (5)C4—C9—H9119.7
C1—N1—N2114.6 (2)N2—C10—S1132.2 (2)
C1—N1—Cd128.5 (2)N2—C10—S2118.3 (2)
N2—N1—Cd116.73 (17)S1—C10—S2109.45 (17)
C10—N2—N1115.2 (2)C12—C11—S2105.4 (2)
C10—S1—Cd95.10 (11)C12—C11—H11A110.7
C10—S2—C11104.71 (14)S2—C11—H11A110.7
N1—C1—C2121.3 (3)C12—C11—H11B110.7
N1—C1—H1119.3S2—C11—H11B110.7
C2—C1—H1119.3H11A—C11—H11B108.8
C3—C2—C1124.1 (3)C13—C12—C17118.2 (3)
C3—C2—H2117.9C13—C12—C11121.0 (3)
C1—C2—H2117.9C17—C12—C11120.8 (3)
C2—C3—C4126.3 (3)C12—C13—C14121.1 (3)
C2—C3—H3116.9C12—C13—H13119.4
C4—C3—H3116.9C14—C13—H13119.4
C5—C4—C9118.1 (3)C15—C14—C13119.9 (4)
C5—C4—C3122.7 (3)C15—C14—H14120.1
C9—C4—C3119.2 (3)C13—C14—H14120.1
C6—C5—C4121.1 (3)C16—C15—C14119.6 (3)
C6—C5—H5119.5C16—C15—H15120.2
C4—C5—H5119.5C14—C15—H15120.2
C5—C6—C7120.1 (3)C15—C16—C17121.0 (3)
C5—C6—H6119.9C15—C16—H16119.5
C7—C6—H6119.9C17—C16—H16119.5
C8—C7—C6119.9 (3)C12—C17—C16120.1 (3)
C8—C7—H7120.0C12—C17—H17119.9
C6—C7—H7120.0C16—C17—H17119.9
N1i—Cd—N1—C1−62.5 (2)C6—C7—C8—C9−1.1 (6)
S1—Cd—N1—C1178.8 (3)C7—C8—C9—C40.8 (6)
S1i—Cd—N1—C123.7 (3)C5—C4—C9—C8−0.3 (5)
N1i—Cd—N1—N2111.98 (19)C3—C4—C9—C8179.3 (3)
S1—Cd—N1—N2−6.76 (17)N1—N2—C10—S1−2.2 (4)
S1i—Cd—N1—N2−161.87 (15)N1—N2—C10—S2176.47 (19)
C1—N1—N2—C10−177.9 (3)Cd—S1—C10—N2−3.1 (3)
Cd—N1—N2—C106.8 (3)Cd—S1—C10—S2178.22 (14)
N1i—Cd—S1—C10−95.26 (13)C11—S2—C10—N2−10.3 (3)
N1—Cd—S1—C104.21 (13)C11—S2—C10—S1168.62 (18)
S1i—Cd—S1—C10138.83 (11)C10—S2—C11—C12−169.8 (2)
N2—N1—C1—C2176.4 (2)S2—C11—C12—C1386.4 (3)
Cd—N1—C1—C2−9.0 (4)S2—C11—C12—C17−92.0 (3)
N1—C1—C2—C3178.8 (3)C17—C12—C13—C14−0.6 (6)
C1—C2—C3—C4176.1 (3)C11—C12—C13—C14−179.1 (3)
C2—C3—C4—C5−3.2 (5)C12—C13—C14—C150.7 (6)
C2—C3—C4—C9177.2 (3)C13—C14—C15—C160.2 (6)
C9—C4—C5—C60.1 (5)C14—C15—C16—C17−1.1 (6)
C3—C4—C5—C6−179.5 (3)C13—C12—C17—C16−0.2 (5)
C4—C5—C6—C7−0.3 (5)C11—C12—C17—C16178.2 (3)
C5—C6—C7—C80.8 (5)C15—C16—C17—C121.1 (6)
D—H···AD—HH···AD···AD—H···A
C13—H13···S2ii0.952.753.690 (4)170
Cd—N12.306 (2)
Cd—S12.4285 (9)
N1i—Cd—N1103.00 (12)
N1i—Cd—S1119.99 (6)
N1—Cd—S180.27 (6)
S1—Cd—S1i 149.19 (5)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C13—H13⋯S2ii 0.952.753.690 (4)170

Symmetry code: (ii) .

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