PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m541.
Published online 2009 April 22. doi:  10.1107/S1600536809013774
PMCID: PMC2977592

Bis[4-hydr­oxy-N′-(4-meth­oxy-2-oxido­benzyl­idene-κO 2)benzohydrazidato-κ2 O,N′]cadmium(II) dimethyl sulfoxide disolvate

Abstract

The metal atom in the title compound, [Cd(C15H13N2O4)2]·2C2H6OS, is twice O,N,O′-chelated by two symmetry-related Schiff base ligands to define a trans-N2O4 octa­hedral geometry. Each anion occupies meridional sites of the octa­hedron; the metal atom lies on a special position of site symmetry 2. The dimethyl sulfoxide mol­ecule is a hydrogen-bond acceptor to the –NH– unit, and O—H(...)O hydrogen bonds link mol­ecules into a supra­molecular chain.

Related literature

For the monohydrated Schiff base ligand, see: Mohd Lair et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m541-scheme1.jpg

Experimental

Crystal data

  • [Cd(C15H13N2O4)2]·2C2H6OS
  • M r = 839.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m541-efi1.jpg
  • a = 23.891 (2) Å
  • b = 10.439 (1) Å
  • c = 19.874 (1) Å
  • β = 132.137 (4)°
  • V = 3675.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.77 mm−1
  • T = 118 K
  • 0.12 × 0.06 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.507, T max = 0.745 (expected range = 0.665–0.977)
  • 10208 measured reflections
  • 3243 independent reflections
  • 2147 reflections with I > 2σ(I)
  • R int = 0.103

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.153
  • S = 1.02
  • 3243 reflections
  • 211 parameters
  • H-atom parameters constrained
  • Δρmax = 1.31 e Å−3
  • Δρmin = −0.90 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013774/tk2421sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013774/tk2421Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide monohydrate (0.30 g, 1 mmol) and cadmium diacetate (0.14 g, 0.5 mmol) were heated in ethanol (50 ml) for 4 h. The solvent was removed and the product was recrystallized from DMSO to give prismatic crystals.

Refinement

Owing to the small number of observed reflections, the aromatic rings were refined as rigid hexagons with sides of 1.39 Å in order to reduce the number of refined parameters. Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98, N–H 0.88, O–H 0.84 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C,N,O). The final difference Fourier map had a large peak/deep hole in the vicinity of the Cd atom.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of Cd(C15H13N2O4)2.2DMSO at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Cd(C15H13N2O4)2]·2C2H6OSF(000) = 1720
Mr = 839.20Dx = 1.517 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 638 reflections
a = 23.891 (2) Åθ = 2.2–18.8°
b = 10.439 (1) ŵ = 0.77 mm1
c = 19.874 (1) ÅT = 118 K
β = 132.137 (4)°Prism, yellow
V = 3675.3 (4) Å30.12 × 0.06 × 0.03 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3243 independent reflections
Radiation source: fine-focus sealed tube2147 reflections with I > 2σ(I)
graphiteRint = 0.103
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −28→28
Tmin = 0.507, Tmax = 0.745k = −12→12
10208 measured reflectionsl = −23→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0692P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3
3243 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 1.31 e Å3
0 restraintsΔρmin = −0.90 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cd10.50000.32500 (7)0.75000.0253 (2)
S10.18289 (10)0.48574 (18)0.67220 (12)0.0335 (5)
O10.4272 (2)0.1893 (4)0.6323 (3)0.0276 (10)
O20.2426 (3)−0.1133 (5)0.4273 (3)0.0373 (12)
O30.5137 (2)0.4972 (4)0.8391 (3)0.0264 (10)
O40.4911 (2)0.8669 (4)1.0697 (3)0.0304 (11)
H40.46240.85071.07910.046*
N10.3944 (3)0.3437 (5)0.7273 (3)0.0227 (12)
N20.3971 (3)0.4373 (5)0.7788 (4)0.0262 (13)
H20.35890.44930.77550.031*
O50.2603 (2)0.4283 (5)0.7353 (4)0.0432 (13)
C10.35890 (17)0.1366 (4)0.5922 (3)0.0261 (16)
C20.3336 (2)0.0367 (4)0.5313 (3)0.0291 (16)
H2A0.36430.00600.52040.035*
C30.2633 (2)−0.0181 (4)0.4865 (3)0.0295 (16)
C40.21840 (18)0.0268 (4)0.5025 (3)0.0339 (17)
H4A0.1704−0.01070.47190.041*
C50.2437 (2)0.1267 (4)0.5634 (3)0.0326 (17)
H50.21300.15740.57430.039*
C60.3140 (2)0.1815 (4)0.6082 (3)0.0286 (15)
C70.1732 (4)−0.1797 (8)0.3856 (5)0.0438 (19)
H7A0.1662−0.24880.34710.066*
H7B0.1309−0.11960.34840.066*
H7C0.1754−0.21590.43280.066*
C80.3314 (4)0.2851 (6)0.6694 (5)0.0269 (16)
H80.29150.31190.66580.032*
C90.4604 (4)0.5100 (6)0.8344 (4)0.0269 (15)
C100.4616 (2)0.6071 (4)0.8911 (2)0.0236 (15)
C110.5075 (2)0.7141 (4)0.9198 (3)0.0289 (16)
H110.53300.72760.89900.035*
C120.5159 (2)0.8012 (3)0.9790 (3)0.0314 (17)
H120.54720.87430.99860.038*
C130.4785 (2)0.7813 (4)1.0094 (3)0.0282 (16)
C140.4326 (2)0.6744 (4)0.9807 (3)0.0241 (14)
H140.40710.66091.00150.029*
C150.4242 (2)0.5873 (3)0.9215 (3)0.0244 (15)
H150.39290.51420.90190.029*
C160.1442 (4)0.4487 (8)0.7214 (5)0.0372 (18)
H16A0.13350.35670.71540.056*
H16B0.09740.49700.69020.056*
H16C0.18050.47200.78580.056*
C170.1980 (4)0.6515 (7)0.6951 (5)0.0424 (19)
H17A0.21750.68820.66900.064*
H17B0.23460.66530.76090.064*
H17C0.15020.69320.66820.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0238 (4)0.0338 (4)0.0243 (4)0.0000.0186 (3)0.000
S10.0368 (10)0.0355 (11)0.0337 (11)−0.0019 (8)0.0259 (9)−0.0040 (9)
O10.025 (2)0.037 (3)0.027 (3)0.000 (2)0.019 (2)0.000 (2)
O20.041 (3)0.041 (3)0.032 (3)−0.010 (2)0.026 (3)−0.012 (2)
O30.025 (2)0.035 (3)0.029 (3)−0.001 (2)0.022 (2)−0.003 (2)
O40.034 (3)0.038 (3)0.032 (3)−0.007 (2)0.028 (2)−0.010 (2)
N10.024 (3)0.026 (3)0.020 (3)−0.001 (2)0.016 (2)0.000 (2)
N20.030 (3)0.033 (3)0.025 (3)0.000 (3)0.022 (3)−0.005 (3)
O50.035 (3)0.042 (3)0.061 (4)0.004 (2)0.036 (3)0.002 (3)
C10.025 (3)0.031 (4)0.020 (4)0.006 (3)0.014 (3)0.007 (3)
C20.034 (4)0.033 (4)0.027 (4)0.007 (3)0.024 (3)0.002 (3)
C30.037 (4)0.025 (4)0.032 (4)−0.003 (3)0.025 (4)0.000 (3)
C40.024 (3)0.045 (5)0.021 (4)−0.012 (3)0.010 (3)−0.006 (3)
C50.030 (4)0.044 (5)0.026 (4)0.005 (3)0.019 (3)0.003 (3)
C60.027 (3)0.035 (4)0.026 (4)0.007 (3)0.018 (3)0.010 (4)
C70.047 (4)0.044 (5)0.035 (4)−0.004 (4)0.025 (4)−0.002 (4)
C80.027 (4)0.024 (4)0.035 (4)0.003 (3)0.024 (3)0.005 (3)
C90.027 (4)0.027 (4)0.022 (4)0.007 (3)0.015 (3)0.006 (3)
C100.021 (3)0.029 (4)0.020 (4)−0.002 (3)0.014 (3)0.000 (3)
C110.035 (4)0.034 (4)0.029 (4)−0.001 (3)0.026 (3)−0.002 (3)
C120.033 (4)0.036 (5)0.035 (4)−0.006 (3)0.027 (3)0.001 (3)
C130.035 (4)0.033 (4)0.022 (4)0.005 (3)0.021 (3)0.002 (3)
C140.025 (3)0.029 (4)0.021 (3)0.004 (3)0.017 (3)0.003 (3)
C150.026 (3)0.026 (4)0.020 (4)−0.002 (3)0.015 (3)0.001 (3)
C160.031 (4)0.051 (5)0.037 (5)−0.004 (3)0.025 (4)−0.006 (4)
C170.050 (4)0.039 (5)0.047 (5)0.004 (4)0.035 (4)−0.001 (4)

Geometric parameters (Å, °)

Cd1—O12.246 (4)C4—H4A0.9500
Cd1—O1i2.246 (4)C5—C61.3900
Cd1—N1i2.254 (5)C5—H50.9500
Cd1—N12.254 (5)C6—C81.464 (7)
Cd1—O32.386 (4)C7—H7A0.9800
Cd1—O3i2.386 (4)C7—H7B0.9800
S1—O51.497 (5)C7—H7C0.9800
S1—C171.764 (7)C8—H80.9500
S1—C161.782 (6)C9—C101.500 (7)
O1—C11.362 (5)C10—C111.3900
O2—C31.355 (5)C10—C151.3900
O2—C71.439 (8)C11—C121.3900
O3—C91.221 (7)C11—H110.9500
O4—C131.356 (5)C12—C131.3900
O4—H40.8400C12—H120.9500
N1—C81.280 (8)C13—C141.3900
N1—N21.385 (7)C14—C151.3900
N2—C91.356 (8)C14—H140.9500
N2—H20.8800C15—H150.9500
C1—C21.3900C16—H16A0.9800
C1—C61.3900C16—H16B0.9800
C2—C31.3900C16—H16C0.9800
C2—H2A0.9500C17—H17A0.9800
C3—C41.3900C17—H17B0.9800
C4—C51.3900C17—H17C0.9800
O1—Cd1—O1i101.8 (2)C5—C6—C8112.7 (3)
O1—Cd1—N1i104.12 (16)C1—C6—C8127.3 (3)
O1i—Cd1—N1i82.26 (16)O2—C7—H7A109.5
O1—Cd1—N182.26 (16)O2—C7—H7B109.5
O1i—Cd1—N1104.12 (16)H7A—C7—H7B109.5
N1i—Cd1—N1170.1 (3)O2—C7—H7C109.5
O1—Cd1—O3150.75 (14)H7A—C7—H7C109.5
O1i—Cd1—O394.45 (15)H7B—C7—H7C109.5
N1i—Cd1—O3102.05 (16)N1—C8—C6127.4 (5)
N1—Cd1—O370.17 (16)N1—C8—H8116.3
O1—Cd1—O3i94.45 (15)C6—C8—H8116.3
O1i—Cd1—O3i150.75 (14)O3—C9—N2122.3 (6)
N1i—Cd1—O3i70.17 (16)O3—C9—C10121.5 (6)
N1—Cd1—O3i102.05 (16)N2—C9—C10116.1 (5)
O3—Cd1—O3i82.3 (2)C11—C10—C15120.0
O5—S1—C17104.7 (3)C11—C10—C9117.7 (3)
O5—S1—C16104.9 (3)C15—C10—C9122.0 (4)
C17—S1—C1699.3 (4)C12—C11—C10120.0
C1—O1—Cd1130.6 (3)C12—C11—H11120.0
C3—O2—C7117.6 (5)C10—C11—H11120.0
C9—O3—Cd1114.2 (4)C11—C12—C13120.0
C13—O4—H4109.5C11—C12—H12120.0
C8—N1—N2116.5 (5)C13—C12—H12120.0
C8—N1—Cd1128.4 (4)O4—C13—C14122.6 (3)
N2—N1—Cd1114.9 (3)O4—C13—C12117.3 (3)
C9—N2—N1118.2 (5)C14—C13—C12120.0
C9—N2—H2120.9C13—C14—C15120.0
N1—N2—H2120.9C13—C14—H14120.0
O1—C1—C2117.6 (3)C15—C14—H14120.0
O1—C1—C6122.4 (3)C14—C15—C10120.0
C2—C1—C6120.0C14—C15—H15120.0
C1—C2—C3120.0C10—C15—H15120.0
C1—C2—H2A120.0S1—C16—H16A109.5
C3—C2—H2A120.0S1—C16—H16B109.5
O2—C3—C2116.1 (3)H16A—C16—H16B109.5
O2—C3—C4123.9 (3)S1—C16—H16C109.5
C2—C3—C4120.0H16A—C16—H16C109.5
C5—C4—C3120.0H16B—C16—H16C109.5
C5—C4—H4A120.0S1—C17—H17A109.5
C3—C4—H4A120.0S1—C17—H17B109.5
C4—C5—C6120.0H17A—C17—H17B109.5
C4—C5—H5120.0S1—C17—H17C109.5
C6—C5—H5120.0H17A—C17—H17C109.5
C5—C6—C1120.0H17B—C17—H17C109.5
O1i—Cd1—O1—C190.7 (4)C3—C4—C5—C60.0
N1i—Cd1—O1—C1175.5 (4)C4—C5—C6—C10.0
N1—Cd1—O1—C1−12.2 (4)C4—C5—C6—C8180.0 (4)
O3—Cd1—O1—C1−31.7 (6)O1—C1—C6—C5178.1 (4)
O3i—Cd1—O1—C1−113.8 (4)C2—C1—C6—C50.0
O1—Cd1—O3—C924.1 (6)O1—C1—C6—C8−1.8 (6)
O1i—Cd1—O3—C9−99.9 (4)C2—C1—C6—C8−179.9 (5)
N1i—Cd1—O3—C9177.1 (4)N2—N1—C8—C6−178.8 (5)
N1—Cd1—O3—C93.5 (4)Cd1—N1—C8—C66.1 (9)
O3i—Cd1—O3—C9109.4 (5)C5—C6—C8—N1171.3 (6)
O1—Cd1—N1—C82.3 (5)C1—C6—C8—N1−8.8 (9)
O1i—Cd1—N1—C8−97.9 (5)Cd1—O3—C9—N2−3.9 (8)
O3—Cd1—N1—C8172.4 (6)Cd1—O3—C9—C10175.5 (4)
O3i—Cd1—N1—C895.3 (5)N1—N2—C9—O31.4 (9)
O1—Cd1—N1—N2−172.8 (4)N1—N2—C9—C10−178.1 (5)
O1i—Cd1—N1—N286.9 (4)O3—C9—C10—C1125.7 (7)
O3—Cd1—N1—N2−2.8 (4)N2—C9—C10—C11−154.8 (4)
O3i—Cd1—N1—N2−79.9 (4)O3—C9—C10—C15−148.5 (5)
C8—N1—N2—C9−173.7 (6)N2—C9—C10—C1531.0 (7)
Cd1—N1—N2—C92.1 (7)C15—C10—C11—C120.0
Cd1—O1—C1—C2−168.0 (3)C9—C10—C11—C12−174.3 (4)
Cd1—O1—C1—C613.8 (6)C10—C11—C12—C130.0
O1—C1—C2—C3−178.2 (4)C11—C12—C13—O4177.6 (4)
C6—C1—C2—C30.0C11—C12—C13—C140.0
C7—O2—C3—C2174.7 (5)O4—C13—C14—C15−177.4 (4)
C7—O2—C3—C4−6.5 (7)C12—C13—C14—C150.0
C1—C2—C3—O2178.9 (5)C13—C14—C15—C100.0
C1—C2—C3—C40.0C11—C10—C15—C140.0
O2—C3—C4—C5−178.8 (5)C9—C10—C15—C14174.1 (4)
C2—C3—C4—C50.0

Symmetry codes: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···O1ii0.841.792.603 (6)163
N2—H2···O50.881.932.766 (6)159

Symmetry codes: (ii) x, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2421).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography