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Acta Cryst. (2007). E63, m2947    [ doi:10.1107/S1600536807056036 ]

Bis[2-(ethylamino)ethanol-[kappa]2N,O]bis(saccharinato-[kappa]N)cadmium(II)

V. T. Yilmaz and C. Kazak

Abstract top

In the centrosymmetric title complex, [Cd(C7H4NO3S)2(C4H11NO)2], the CdII ion is coordinated by two saccharinate (sac) anions and two N,O-bidentate 2-(ethylamino)ethanol ligands, displaying a distorted octahedral coordination. Pairs of molecules are doubly bridged by O-H...O hydrogen bonds and these dimers are further linked by weak C-H...[pi](sac) interactions.

Comment top

Although metal complexes of 2-dimethylaminoethanol have received considerable attention (Ahlgrén et al. 1982; Turpeinen & Hamalainen 1985; Turpeinen et al., 1996; Vinogradova et al., 2001), 2-ethylaminoethanol-metal complexes are very rare and we recently reported the first two copper(II) complexes (Yilmaz et al., 2006, 2007). This work is a part of our study on the synthesis and structural characterization of metal complexes of saccharin (Hsac) with other co-ligands (Baran & Yilmaz 2006). We report here the crystal and molecular structure of the title compound, (I).

As illustrated in (Fig. 1), (I) is a mononuclear CdII complex, in which the CdII ion lies on a centre of inversion and exhibits a somewhat distorted octahedral coordination geometry with two neutral bidendate (N, O) eae ligands and two anionic sac ligands (Table 1). The amine hydrogen atoms of 2-ethyaminoethanol form intramolecular N—H···O interactions with sulfonyl O atoms of the saccharinate anion (Table 2). Individual molecules are linked into pairs by double O—H···O hydrogen bonds involving the H atoms of the hydroxyl groups of 2-ethyaminoethanol and the carbonyl O atoms of the saccharinate anion (Fig. 2). The dimeric units are further linked by weak C—H···π-(sac) interactions with an H···π separation of 2.97 Å.

Related literature top

For related structures, see: Ahlgrén et al. (1982); Turpeinen & Hamalainen (1985); Turpeinen et al.(1996); Vinogradova et al. (2001); Yilmaz et al. (2006); Baran & Yilmaz (2006); Yilmaz et al. (2007).

Experimental top

2-Ethylaminoethanol (0.09 g, 1 mmol) was added dropwise to a 20-ml methanol solution containing Cd(OAc)2·2H2O (0.13 g, 0.5 mmol) and saccharin (0.18 g, 1 mmol). The reaction solution was stirred for 30 min at room temperature. Colourless prisms of (I) were obtained after 2 days by slow evoparation of the solution at room temperature.

Refinement top

The O-bound H atom was located in a difference map and freely refined. The other H atoms were refined with a riding model (C—H = 0.93–0.97 Å, N—H = 0.91 Å) with Uiso(H) = 1.2 Ueq(C, N) or 1.5Ueq(methyl C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP 3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 19993).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms). Symmetry code: (i) −x, −y, −z. The intermolecular N—H···O bonds are indicated by dashed lines.
[Figure 2] Fig. 2. The packing of the molecules in (I) along the b axis. Dashed lines represent hydrogen bonds.
Bis[2-(ethylamino)ethanol-κ2N,O]bis(saccharinato-κN)cadmium(II) top
Crystal data top
[Cd(C7H4NO3S)2(C4H11NO)2]F000 = 668
Mr = 655.05Dx = 1.645 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 21565 reflections
a = 7.7961 (6) Åθ = 2.1–27.4º
b = 19.2676 (19) ŵ = 1.04 mm−1
c = 8.8162 (7) ÅT = 296 (2) K
β = 93.061 (6)ºPrism, colorless
V = 1322.4 (2) Å30.21 × 0.19 × 0.18 mm
Z = 2
Data collection top
STOE IPDS 2
diffractometer		2980 independent reflections
Radiation source: fine-focus sealed tube2013 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.076
Detector resolution: 6.67 pixels mm-1θmax = 27.4º
T = 296(2) Kθmin = 2.1º
rotation method scansh = −10→9
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −24→24
Tmin = 0.783, Tmax = 0.822l = −11→11
21045 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.085P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
2980 reflectionsΔρmax = 1.42 e Å−3
167 parametersΔρmin = −1.17 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cd(C7H4NO3S)2(C4H11NO)2]V = 1322.4 (2) Å3
Mr = 655.05Z = 2
Monoclinic, P21/cMo Kα
a = 7.7961 (6) ŵ = 1.04 mm−1
b = 19.2676 (19) ÅT = 296 (2) K
c = 8.8162 (7) Å0.21 × 0.19 × 0.18 mm
β = 93.061 (6)º
Data collection top
STOE IPDS 2
diffractometer		2980 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2013 reflections with I > 2σ(I)
Tmin = 0.783, Tmax = 0.822Rint = 0.076
21045 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0493 restraints
wR(F2) = 0.135H atoms treated by a mixture of
independent and constrained refinement
S = 0.96Δρmax = 1.42 e Å−3
2980 reflectionsΔρmin = −1.17 e Å−3
167 parameters
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
C1−0.3311 (13)0.0910 (6)−0.1374 (13)0.038 (2)
C2−0.3971 (12)0.1381 (5)−0.2668 (11)0.032 (2)
C3−0.2683 (13)0.1732 (5)−0.3368 (11)0.034 (2)
C4−0.3022 (16)0.2207 (6)−0.4505 (13)0.047 (3)
H4−0.21440.2443−0.49590.056*
C5−0.4724 (16)0.2318 (7)−0.4944 (15)0.056 (3)
H5−0.49970.2634−0.57170.067*
C6−0.6030 (16)0.1975 (6)−0.4271 (14)0.048 (3)
H6−0.71640.2063−0.45930.058*
C7−0.5676 (13)0.1499 (6)−0.3118 (12)0.039 (2)
H7−0.65560.1265−0.26610.047*
C8−0.242 (3)−0.1147 (11)−0.139 (2)0.096 (5)
H8A−0.1807−0.1577−0.11920.115*
H8B−0.3614−0.1261−0.16560.115*
C9−0.174 (3)−0.0818 (12)−0.261 (2)0.096 (5)
H9A−0.2485−0.0438−0.29300.115*
H9B−0.1698−0.1143−0.34440.115*
C100.152 (2)−0.0957 (8)−0.2728 (17)0.073 (4)
H10A0.1965−0.1225−0.18630.088*
H10B0.1171−0.1282−0.35270.088*
C110.290 (2)−0.0513 (11)−0.327 (2)0.092 (6)
H11A0.3867−0.0796−0.34980.137*
H11B0.3247−0.0185−0.24880.137*
H11C0.2494−0.0268−0.41630.137*
N1−0.1521 (11)0.0927 (5)−0.1290 (10)0.039 (2)
N2−0.0067 (15)−0.0556 (7)−0.2268 (12)0.063 (3)
H2−0.0052−0.0189−0.29180.075*
O10.0239 (10)0.1062 (5)−0.3575 (10)0.051 (2)
O20.0178 (10)0.2013 (4)−0.1787 (11)0.054 (2)
O3−0.4149 (10)0.0592 (5)−0.0628 (11)0.056 (2)
O4−0.2338 (10)−0.0744 (5)−0.0105 (10)0.051 (2)
S1−0.0711 (3)0.14465 (14)−0.2516 (3)0.0373 (6)
Cd10.00000.00000.00000.0364 (4)
H4A−0.337 (10)−0.066 (8)0.024 (17)0.07 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.031 (5)0.040 (5)0.044 (6)−0.001 (4)0.003 (5)0.004 (5)
C20.032 (5)0.031 (5)0.032 (5)0.000 (4)0.001 (4)0.000 (4)
C30.036 (5)0.034 (5)0.031 (5)0.002 (4)0.004 (4)0.002 (4)
C40.054 (7)0.044 (6)0.042 (6)0.000 (5)0.008 (5)0.014 (5)
C50.061 (9)0.055 (7)0.050 (7)0.008 (6)−0.006 (6)0.022 (6)
C60.040 (6)0.053 (7)0.050 (7)0.005 (5)−0.009 (5)0.004 (5)
C70.033 (5)0.042 (6)0.043 (6)−0.005 (4)0.002 (4)0.000 (5)
C80.089 (9)0.120 (11)0.082 (9)−0.050 (8)0.021 (7)−0.040 (8)
C90.089 (9)0.120 (11)0.082 (9)−0.050 (8)0.021 (7)−0.040 (8)
C100.110 (13)0.061 (9)0.048 (8)0.016 (9)0.005 (8)−0.011 (6)
C110.052 (9)0.131 (17)0.093 (13)0.014 (10)0.009 (9)−0.036 (12)
N10.027 (4)0.046 (5)0.043 (5)0.002 (4)0.003 (4)0.016 (4)
N20.062 (7)0.088 (8)0.039 (6)−0.018 (6)0.003 (5)−0.014 (5)
O10.040 (4)0.061 (5)0.052 (5)0.011 (4)0.018 (4)0.007 (4)
O20.042 (4)0.052 (5)0.067 (6)−0.011 (4)0.000 (4)0.003 (4)
O30.035 (4)0.067 (5)0.068 (6)−0.001 (4)0.012 (4)0.035 (5)
O40.035 (4)0.057 (5)0.061 (5)−0.001 (4)0.006 (4)0.003 (4)
S10.0281 (12)0.0427 (13)0.0417 (14)0.0019 (11)0.0068 (10)0.0069 (11)
Cd10.0379 (6)0.0371 (6)0.0339 (6)−0.0007 (5)−0.0005 (4)0.0030 (5)
Geometric parameters (Å, °) top
C1—O31.133 (12)C9—H9B0.9700
C1—N11.394 (13)C10—C111.48 (3)
C1—C21.525 (14)C10—N21.53 (2)
C2—C31.383 (14)C10—H10A0.9700
C2—C71.386 (14)C10—H10B0.9700
C3—C41.372 (14)C11—H11A0.9600
C3—S11.763 (10)C11—H11B0.9600
C4—C51.379 (17)C11—H11C0.9600
C4—H40.9300N1—S11.625 (9)
C5—C61.375 (18)N2—H20.9100
C5—H50.9300O1—S11.429 (8)
C6—C71.386 (16)O2—S11.427 (9)
C6—H60.9300O4—H4A0.89 (10)
C7—H70.9300Cd1—N2i2.267 (10)
C8—C91.37 (3)Cd1—O4i2.317 (8)
C8—O41.374 (18)Cd1—N1i2.397 (9)
C8—H8A0.9700Cd1—N12.397 (9)
C8—H8B0.9700Cd1—N22.267 (10)
C9—N21.41 (2)Cd1—O42.317 (8)
C9—H9A0.9700
O3—C1—N1126.0 (11)C10—C11—H11A109.5
O3—C1—C2125.1 (10)C10—C11—H11B109.5
N1—C1—C2108.8 (8)H11A—C11—H11B109.5
C3—C2—C7120.0 (9)C10—C11—H11C109.5
C3—C2—C1113.6 (9)H11A—C11—H11C109.5
C7—C2—C1126.3 (9)H11B—C11—H11C109.5
C4—C3—C2122.4 (10)C1—N1—S1113.7 (7)
C4—C3—S1130.5 (8)C1—N1—Cd1118.4 (7)
C2—C3—S1107.1 (7)S1—N1—Cd1125.1 (5)
C3—C4—C5117.0 (11)C9—N2—C10120.7 (13)
C3—C4—H4121.5C9—N2—Cd1109.4 (9)
C5—C4—H4121.5C10—N2—Cd1119.5 (9)
C6—C5—C4121.8 (11)C9—N2—H2100.8
C6—C5—H5119.1C10—N2—H2100.8
C4—C5—H5119.1Cd1—N2—H2100.8
C5—C6—C7120.8 (11)C8—O4—Cd1112.7 (8)
C5—C6—H6119.6C8—O4—H4A112 (10)
C7—C6—H6119.6Cd1—O4—H4A127 (10)
C2—C7—C6117.9 (10)O2—S1—O1115.8 (5)
C2—C7—H7121.0O2—S1—N1111.6 (5)
C6—C7—H7121.0O1—S1—N1110.4 (5)
C9—C8—O4112.3 (15)O2—S1—C3110.2 (5)
C9—C8—H8A109.1O1—S1—C3110.7 (5)
O4—C8—H8A109.1N1—S1—C396.6 (5)
C9—C8—H8B109.1N2i—Cd1—N2180.0 (9)
O4—C8—H8B109.1N2i—Cd1—O4i72.0 (4)
H8A—C8—H8B107.9N2—Cd1—O4i108.0 (4)
C8—C9—N2113.2 (17)N2i—Cd1—O4108.0 (4)
C8—C9—H9A108.9N2—Cd1—O472.0 (4)
N2—C9—H9A108.9O4i—Cd1—O4180.0 (4)
C8—C9—H9B108.9N2i—Cd1—N1i86.9 (4)
N2—C9—H9B108.9N2—Cd1—N1i93.1 (4)
H9A—C9—H9B107.8O4i—Cd1—N1i94.3 (3)
C11—C10—N2114.0 (12)O4—Cd1—N1i85.7 (3)
C11—C10—H10A108.8N2i—Cd1—N193.1 (4)
N2—C10—H10A108.8N2—Cd1—N186.9 (4)
C11—C10—H10B108.8O4i—Cd1—N185.7 (3)
N2—C10—H10B108.8O4—Cd1—N194.3 (3)
H10A—C10—H10B107.6N1i—Cd1—N1180.0 (5)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O3ii0.89 (10)1.99 (6)2.863 (11)168 (15)
N2—H2···O10.912.493.336 (16)154
Symmetry codes: (ii) −x−1, −y, −z.
Table 1
Selected geometric parameters (Å) top
Cd1—N12.397 (9)Cd1—O42.317 (8)
Cd1—N22.267 (10)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O3i0.89 (10)1.99 (6)2.863 (11)168 (15)
N2—H2···O10.912.493.336 (16)154
Symmetry codes: (i) −x−1, −y, −z.
references
References top

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