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Acta Cryst. (2009). E65, m541    [ doi:10.1107/S1600536809013774 ]

Bis[4-hydroxy-N'-(4-methoxy-2-oxidobenzylidene-[kappa]O2)benzohydrazidato-[kappa]2O,N']cadmium(II) dimethyl sulfoxide disolvate

N. Mohd Lair, H. Mohd Ali and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
Bis[4-hydroxy-N'-(4-methoxy-2-oxidobenzylidene- κO2)benzohydrazidato-κ2O,N']cadmium(II) dimethyl sulfoxide disolvate top
Crystal data top
[Cd(C15H13N2O4)2]·2C2H6OSF(000) = 1720
Mr = 839.20Dx = 1.517 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		3243 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 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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02 w = 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 Å−3
0 restraintsΔρmin = −0.90 e Å−3
Crystal data top
[Cd(C15H13N2O4)2]·2C2H6OSV = 3675.3 (4) Å3
Mr = 839.20Z = 4
Monoclinic, C2/cMo Kα radiation
a = 23.891 (2) ŵ = 0.77 mm−1
b = 10.439 (1) ÅT = 118 K
c = 19.874 (1) Å0.12 × 0.06 × 0.03 mm
β = 132.137 (4)°
Data collection top
Bruker SMART APEX
diffractometer		3243 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2147 reflections with I > 2σ(I)
Tmin = 0.507, Tmax = 0.745Rint = 0.103
10208 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.153Δρmax = 1.31 e Å−3
S = 1.02Δρmin = −0.90 e Å−3
3243 reflectionsAbsolute structure: ?
211 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.841.792.603 (6)163
N2—H2···O50.881.932.766 (6)159
Symmetry codes: (i) x, −y+1, z+1/2.
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Lair, N. M., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o189.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.