Literature DB >> 22807758

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

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

Abstract

In the title compound, [Hg(C(17)H(15)N(2)S(2))(2)], the Hg(II) ion lies on a crystallographic twofold rotation axis giving a very distorted tetra-hedral coordination geometry best described as bis-phenoidal, being chelated by two deprotonated N,S Schiff base ligands through the azomethine nitro-gen and the thiol-ate sulfur donors. The dihedral angle between the two chelating ligand moieties is 79.75 (10)°. In the crystal, weak C-H⋯S inter-actions give rise to chains extending along the c axis.

Entities:  

Year:  2012        PMID： 22807758      PMCID： PMC3393190          DOI： 10.1107/S1600536812025901

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


Related literature

For the structures of uncoordinated Schiff bases, see: Tarafder, Crouse et al. (2008 ▶); Tarafder, Islam et al. (2008 ▶). For the corresponding ZnII complex, see: Fun et al. (2008 ▶). 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

[Hg(C17H15N2S2)2] M = 823.49 Orthorhombic, a = 36.3639 (6) Å b = 10.11949 (10) Å c = 8.77097 (10) Å V = 3227.58 (7) Å3 Z = 4 Cu Kα radiation μ = 11.21 mm−1 T = 173 K 0.37 × 0.15 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID CCD-detector diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.194, T max = 0.249 33943 measured reflections 2957 independent reflections 2829 reflections with I 2 > 2σ(I 2) R int = 0.113

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.097 S = 1.20 2957 reflections 195 parameters H-atom parameters constrained Δρmax = 1.76 e Å−3 Δρmin = −2.04 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) General, I. DOI: 10.1107/S1600536812025901/zs2213sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025901/zs2213Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Hg(C17H15N2S2)2]Dx = 1.695 Mg m−3
Mr = 823.49Melting point = 472–473 K
Orthorhombic, PbcnCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2n 2abCell parameters from 33993 reflections
a = 36.3639 (6) Åθ = 3.7–68.3°
b = 10.11949 (10) ŵ = 11.21 mm−1
c = 8.77097 (10) ÅT = 173 K
V = 3227.58 (7) Å3Prism, yellow
Z = 40.37 × 0.15 × 0.13 mm
F(000) = 1624.00
Rigaku R-AXIS RAPID CCD-detector diffractometer2829 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.113
ω scansθmax = 68.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −43→41
Tmin = 0.194, Tmax = 0.249k = −11→12
33943 measured reflectionsl = −10→10
2957 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.20w = 1/[σ2(Fo2) + (0.0485P)2 + 2.6351P] where P = (Fo2 + 2Fc2)/3
2957 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 1.76 e Å−3
0 restraintsΔρmin = −2.04 e Å−3
Primary atom site location: structure-invariant direct methods
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
Hg0.50000.469781 (18)0.75000.02693 (12)
S160.62936 (2)0.39052 (10)0.66996 (11)0.0407 (3)
S180.56373 (3)0.50749 (11)0.78335 (13)0.0324 (2)
N190.56567 (6)0.2929 (3)0.5827 (3)0.0238 (6)
N200.52759 (6)0.2998 (3)0.5798 (3)0.0230 (5)
C20.71088 (9)0.2399 (4)0.5613 (5)0.0378 (8)
C30.74786 (9)0.2696 (4)0.5437 (6)0.0460 (10)
C40.75868 (9)0.3722 (4)0.4538 (5)0.0389 (9)
C50.73268 (11)0.4492 (5)0.3839 (5)0.0474 (10)
C60.69574 (10)0.4202 (4)0.4017 (5)0.0421 (9)
C70.68432 (8)0.3154 (3)0.4901 (4)0.0264 (7)
C80.41564 (8)0.1159 (3)0.3608 (4)0.0236 (6)
C90.39145 (8)0.2117 (3)0.4171 (4)0.0285 (7)
C100.35438 (9)0.2050 (4)0.3860 (4)0.0335 (8)
C110.34047 (10)0.1024 (4)0.2978 (5)0.0351 (8)
C120.36386 (15)0.0076 (7)0.2403 (4)0.0370 (11)
C130.40136 (14)0.0130 (5)0.2717 (5)0.0330 (10)
C140.64395 (9)0.2869 (4)0.5117 (4)0.0315 (7)
C150.45518 (8)0.1197 (3)0.3903 (4)0.0265 (7)
C170.58149 (8)0.3828 (3)0.6662 (4)0.0244 (7)
C210.47292 (9)0.2093 (3)0.4763 (4)0.0264 (7)
C220.51223 (10)0.2110 (3)0.4954 (4)0.0256 (7)
H20.70380.16700.62290.0453*
H30.76580.21790.59490.0552*
H40.78410.39030.43960.0467*
H50.74000.52250.32330.0568*
H60.67790.47350.35200.0505*
H90.40070.28220.47740.0342*
H100.33830.27070.42490.0402*
H110.31490.09760.27730.0421*
H120.3544−0.06170.17880.0444*
H130.4173−0.05330.23270.0396*
H14A0.64000.19240.53580.0378*
H14B0.63000.30900.41820.0378*
H150.46970.05260.34440.0318*
H210.45880.27480.52710.0317*
H220.52700.14650.44570.0307*
U11U22U33U12U13U23
Hg0.02006 (18)0.02382 (18)0.03692 (18)0.00000.00999 (6)0.0000
S160.0147 (4)0.0603 (6)0.0470 (5)−0.0065 (4)−0.0006 (4)−0.0233 (5)
S180.0250 (5)0.0302 (4)0.0418 (5)−0.0094 (4)0.0089 (5)−0.0114 (4)
N190.0120 (12)0.0279 (13)0.0317 (13)0.0007 (10)0.0001 (10)−0.0032 (11)
N200.0127 (12)0.0237 (12)0.0325 (13)−0.0007 (10)0.0023 (10)−0.0015 (11)
C20.0201 (17)0.0394 (19)0.054 (3)−0.0006 (14)−0.0029 (16)0.0114 (16)
C30.019 (2)0.052 (3)0.067 (3)0.0085 (16)−0.0066 (16)0.0087 (19)
C40.0150 (17)0.056 (3)0.046 (2)−0.0057 (15)0.0020 (14)−0.0027 (17)
C50.031 (3)0.054 (3)0.057 (3)−0.0087 (18)0.0024 (18)0.018 (2)
C60.0227 (18)0.049 (3)0.055 (3)0.0022 (16)−0.0089 (16)0.0142 (18)
C70.0141 (15)0.0306 (15)0.0345 (16)−0.0000 (12)−0.0018 (12)−0.0061 (14)
C80.0174 (15)0.0259 (15)0.0274 (15)−0.0047 (12)0.0002 (12)0.0032 (12)
C90.0211 (16)0.0286 (16)0.0359 (17)−0.0043 (13)0.0007 (13)0.0000 (13)
C100.0176 (16)0.0381 (18)0.0449 (19)−0.0011 (13)0.0028 (14)0.0050 (15)
C110.0217 (18)0.047 (2)0.0365 (18)−0.0069 (15)−0.0034 (16)0.0086 (17)
C120.027 (3)0.040 (3)0.045 (3)−0.012 (3)−0.0067 (14)−0.0019 (14)
C130.025 (3)0.033 (3)0.041 (2)−0.0034 (18)−0.0018 (16)−0.0022 (15)
C140.0144 (16)0.0412 (17)0.0388 (18)−0.0012 (13)−0.0021 (13)−0.0102 (16)
C150.0185 (15)0.0268 (15)0.0341 (16)−0.0007 (12)0.0022 (13)−0.0007 (13)
C170.0148 (15)0.0286 (16)0.0296 (15)−0.0026 (12)0.0041 (12)−0.0005 (12)
C210.0159 (17)0.0281 (15)0.0352 (16)−0.0004 (12)0.0000 (13)−0.0021 (13)
C220.0190 (17)0.0246 (14)0.0332 (17)0.0009 (12)0.0019 (14)−0.0017 (14)
Hg—S182.3668 (11)C10—C111.390 (6)
Hg—S18i2.3668 (11)C11—C121.378 (7)
Hg—N202.489 (3)C12—C131.392 (8)
Hg—N20i2.489 (3)C15—C211.344 (5)
S16—C141.819 (4)C21—C221.439 (5)
S16—C171.743 (3)C2—H20.950
S18—C171.751 (4)C3—H30.950
N19—N201.387 (3)C4—H40.950
N19—C171.302 (4)C5—H50.950
N20—C221.291 (4)C6—H60.950
C2—C31.387 (5)C9—H90.950
C2—C71.381 (5)C10—H100.950
C3—C41.362 (6)C11—H110.950
C4—C51.370 (6)C12—H120.950
C5—C61.384 (6)C13—H130.950
C6—C71.378 (5)C14—H14A0.990
C7—C141.508 (5)C14—H14B0.990
C8—C91.399 (5)C15—H150.950
C8—C131.402 (6)C21—H210.950
C8—C151.461 (5)C22—H220.950
C9—C101.377 (5)
S18—Hg—S18i161.44 (4)C15—C21—C22123.4 (3)
S18—Hg—N2077.93 (6)N20—C22—C21120.3 (3)
S18—Hg—N20i115.59 (6)C3—C2—H2119.735
S18i—Hg—N20115.59 (6)C7—C2—H2119.740
S18i—Hg—N20i77.93 (6)C2—C3—H3119.689
N20—Hg—N20i92.57 (8)C4—C3—H3119.649
C14—S16—C17104.53 (15)C3—C4—H4120.216
Hg—S18—C1799.93 (11)C5—C4—H4120.214
N20—N19—C17114.6 (3)C4—C5—H5120.049
Hg—N20—N19115.23 (17)C6—C5—H5120.064
Hg—N20—C22130.6 (2)C5—C6—H6119.331
N19—N20—C22114.1 (3)C7—C6—H6119.352
C3—C2—C7120.5 (4)C8—C9—H9119.641
C2—C3—C4120.7 (4)C10—C9—H9119.620
C3—C4—C5119.6 (4)C9—C10—H10119.893
C4—C5—C6119.9 (4)C11—C10—H10119.869
C5—C6—C7121.3 (4)C10—C11—H11120.030
C2—C7—C6118.0 (3)C12—C11—H11120.023
C2—C7—C14121.2 (3)C11—C12—H12119.828
C6—C7—C14120.7 (3)C13—C12—H12119.847
C9—C8—C13118.6 (4)C8—C13—H13119.940
C9—C8—C15122.5 (3)C12—C13—H13119.916
C13—C8—C15118.9 (4)S16—C14—H14A110.606
C8—C9—C10120.7 (3)S16—C14—H14B110.610
C9—C10—C11120.2 (4)C7—C14—H14A110.602
C10—C11—C12119.9 (4)C7—C14—H14B110.598
C11—C12—C13120.3 (5)H14A—C14—H14B108.752
C8—C13—C12120.1 (5)C8—C15—H15116.950
S16—C14—C7105.7 (3)C21—C15—H15116.938
C8—C15—C21126.1 (3)C15—C21—H21118.300
S16—C17—S18108.96 (17)C22—C21—H21118.323
S16—C17—N19118.9 (3)N20—C22—H22119.829
S18—C17—N19132.1 (3)C21—C22—H22119.850
S18—Hg—N20—N193.69 (13)Hg—N20—C22—C217.3 (4)
S18—Hg—N20—C22178.9 (2)N19—N20—C22—C21−177.4 (3)
N20—Hg—S18—C17−1.67 (7)C3—C2—C7—C60.0 (6)
S18—Hg—N20i—N19i170.22 (12)C3—C2—C7—C14−178.2 (4)
S18—Hg—N20i—C22i−14.5 (3)C7—C2—C3—C4−1.2 (7)
N20i—Hg—S18—C1785.38 (8)C2—C3—C4—C52.0 (7)
S18i—Hg—N20—N19170.22 (12)C3—C4—C5—C6−1.8 (6)
S18i—Hg—N20—C22−14.5 (3)C4—C5—C6—C70.6 (6)
N20—Hg—S18i—C17i85.38 (8)C5—C6—C7—C20.2 (6)
S18i—Hg—N20i—N19i3.69 (13)C5—C6—C7—C14178.4 (4)
S18i—Hg—N20i—C22i178.9 (2)C2—C7—C14—S1692.6 (4)
N20i—Hg—S18i—C17i−1.67 (7)C6—C7—C14—S16−85.5 (4)
N20—Hg—N20i—N19i−111.94 (15)C9—C8—C13—C120.2 (5)
N20—Hg—N20i—C22i63.3 (2)C13—C8—C9—C100.2 (5)
N20i—Hg—N20—N19−111.94 (15)C9—C8—C15—C212.4 (5)
N20i—Hg—N20—C2263.3 (2)C15—C8—C9—C10179.6 (3)
C14—S16—C17—S18−166.34 (16)C13—C8—C15—C21−178.1 (3)
C14—S16—C17—N1913.3 (3)C15—C8—C13—C12−179.3 (3)
C17—S16—C14—C7167.73 (17)C8—C9—C10—C11−0.0 (5)
Hg—S18—C17—S16179.53 (13)C9—C10—C11—C12−0.5 (6)
Hg—S18—C17—N19−0.0 (3)C10—C11—C12—C130.9 (6)
N20—N19—C17—S16−176.2 (2)C11—C12—C13—C8−0.8 (7)
N20—N19—C17—S183.3 (5)C8—C15—C21—C22−177.1 (3)
C17—N19—N20—Hg−4.6 (3)C15—C21—C22—N20−180.0 (3)
C17—N19—N20—C22179.4 (3)
D—H···AD—HH···AD···AD—H···A
C6—H6···S16ii0.952.753.692 (4)172
Table 1

Selected bond lengths (Å)

Hg—S182.3668 (11)
Hg—N202.489 (3)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C6—H6⋯S16i 0.952.753.692 (4)172

Symmetry code: (i) .

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2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Bis[benzyl N'-(3-phenyl-prop-2-enyl-idene)hydrazinecarbodithio-ato-κN',S]zinc(II).

Authors:  Hoong-Kun Fun; Suchada Chantrapromma; M T H Tarafder; M Toihidul Islam; C M Zakaria; M A A A A Islam
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-05

4.  Benzyl 3-[(E,E)-3-phenyl-prop-2-enyl-idene]dithio-carbazate.

Authors:  M T H Tarafder; K A Crouse; M Toihidul Islam; Suchada Chantrapromma; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-10

5.  Bis[benzyl N'-(3-phenyl-prop-2-enyl-idene)hydrazinecarbodithio-ato-κN',S]copper(II).

Authors:  M T H Tarafder; M Toihidul Islam; M A A A A Islam; Suchada Chantrapromma; Hoong-Kun Fun
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1.  Bis[benzyl 3-(3-phenyl-prop-2-enyl-idene)dithio-carbazato-κ(2)N(3),S]cadmium.

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