Bis[2-(ethyl­amino)ethanol-κ²N,O]bis­(saccharinato-κN)cadmium(II)

In the centrosymmetric title complex, [Cd(C₇H₄NO₃S)₂(C₄H₁₁NO)₂], the Cd^II 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...π(sac) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.018 Å
• R factor = 0.049
• wR factor = 0.135
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

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Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         18
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C8     -   C9     ...       1.38 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.53 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O3     ..  O3      ..       2.89 Ang.

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1         (2)       2.14
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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 Cd^II complex, in which the Cd^II 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

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).

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2 U_eq(C, N) or 1.5U_eq(methyl C).

Computing details

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

	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.
	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)

Crystal data

[Cd(C7H4NO3S)2(C4H11NO)2]	F(000) = 668
Mr = 655.05	Dx = 1.645 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 21565 reflections
a = 7.7961 (6) Å	θ = 2.1–27.4°
b = 19.2676 (19) Å	µ = 1.04 mm^−1
c = 8.8162 (7) Å	T = 296 K
β = 93.061 (6)°	Prism, colorless
V = 1322.4 (2) Å^3	0.21 × 0.19 × 0.18 mm
Z = 2

Data collection

STOE IPDS 2 diffractometer	2980 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 6.67 pixels mm^-1	θmax = 27.4°, θmin = 2.1°
rotation method scans	h = −10→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
Tmin = 0.783, Tmax = 0.822	l = −11→11
21045 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.085P)^2] where P = (Fo^2 + 2Fc^2)/3
2980 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 1.42 e Å^−3
3 restraints	Δρmin = −1.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/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	−0.2144	0.2443	−0.4959	0.056*
C5	−0.4724 (16)	0.2318 (7)	−0.4944 (15)	0.056 (3)
H5	−0.4997	0.2634	−0.5717	0.067*
C6	−0.6030 (16)	0.1975 (6)	−0.4271 (14)	0.048 (3)
H6	−0.7164	0.2063	−0.4593	0.058*
C7	−0.5676 (13)	0.1499 (6)	−0.3118 (12)	0.039 (2)
H7	−0.6556	0.1265	−0.2661	0.047*
C8	−0.242 (3)	−0.1147 (11)	−0.139 (2)	0.096 (5)
H8A	−0.1807	−0.1577	−0.1192	0.115*
H8B	−0.3614	−0.1261	−0.1656	0.115*
C9	−0.174 (3)	−0.0818 (12)	−0.261 (2)	0.096 (5)
H9A	−0.2485	−0.0438	−0.2930	0.115*
H9B	−0.1698	−0.1143	−0.3444	0.115*
C10	0.152 (2)	−0.0957 (8)	−0.2728 (17)	0.073 (4)
H10A	0.1965	−0.1225	−0.1863	0.088*
H10B	0.1171	−0.1282	−0.3527	0.088*
C11	0.290 (2)	−0.0513 (11)	−0.327 (2)	0.092 (6)
H11A	0.3867	−0.0796	−0.3498	0.137*
H11B	0.3247	−0.0185	−0.2488	0.137*
H11C	0.2494	−0.0268	−0.4163	0.137*
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	−0.2918	0.075*
O1	0.0239 (10)	0.1062 (5)	−0.3575 (10)	0.051 (2)
O2	0.0178 (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)
Cd1	0.0000	0.0000	0.0000	0.0364 (4)
H4A	−0.337 (10)	−0.066 (8)	0.024 (17)	0.07 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.031 (5)	0.040 (5)	0.044 (6)	−0.001 (4)	0.003 (5)	0.004 (5)
C2	0.032 (5)	0.031 (5)	0.032 (5)	0.000 (4)	0.001 (4)	0.000 (4)
C3	0.036 (5)	0.034 (5)	0.031 (5)	0.002 (4)	0.004 (4)	0.002 (4)
C4	0.054 (7)	0.044 (6)	0.042 (6)	0.000 (5)	0.008 (5)	0.014 (5)
C5	0.061 (9)	0.055 (7)	0.050 (7)	0.008 (6)	−0.006 (6)	0.022 (6)
C6	0.040 (6)	0.053 (7)	0.050 (7)	0.005 (5)	−0.009 (5)	0.004 (5)
C7	0.033 (5)	0.042 (6)	0.043 (6)	−0.005 (4)	0.002 (4)	0.000 (5)
C8	0.089 (9)	0.120 (11)	0.082 (9)	−0.050 (8)	0.021 (7)	−0.040 (8)
C9	0.089 (9)	0.120 (11)	0.082 (9)	−0.050 (8)	0.021 (7)	−0.040 (8)
C10	0.110 (13)	0.061 (9)	0.048 (8)	0.016 (9)	0.005 (8)	−0.011 (6)
C11	0.052 (9)	0.131 (17)	0.093 (13)	0.014 (10)	0.009 (9)	−0.036 (12)
N1	0.027 (4)	0.046 (5)	0.043 (5)	0.002 (4)	0.003 (4)	0.016 (4)
N2	0.062 (7)	0.088 (8)	0.039 (6)	−0.018 (6)	0.003 (5)	−0.014 (5)
O1	0.040 (4)	0.061 (5)	0.052 (5)	0.011 (4)	0.018 (4)	0.007 (4)
O2	0.042 (4)	0.052 (5)	0.067 (6)	−0.011 (4)	0.000 (4)	0.003 (4)
O3	0.035 (4)	0.067 (5)	0.068 (6)	−0.001 (4)	0.012 (4)	0.035 (5)
O4	0.035 (4)	0.057 (5)	0.061 (5)	−0.001 (4)	0.006 (4)	0.003 (4)
S1	0.0281 (12)	0.0427 (13)	0.0417 (14)	0.0019 (11)	0.0068 (10)	0.0069 (11)
Cd1	0.0379 (6)	0.0371 (6)	0.0339 (6)	−0.0007 (5)	−0.0005 (4)	0.0030 (5)

Geometric parameters (Å, º)

C1—O3	1.133 (12)	C9—H9B	0.9700
C1—N1	1.394 (13)	C10—C11	1.48 (3)
C1—C2	1.525 (14)	C10—N2	1.53 (2)
C2—C3	1.383 (14)	C10—H10A	0.9700
C2—C7	1.386 (14)	C10—H10B	0.9700
C3—C4	1.372 (14)	C11—H11A	0.9600
C3—S1	1.763 (10)	C11—H11B	0.9600
C4—C5	1.379 (17)	C11—H11C	0.9600
C4—H4	0.9300	N1—S1	1.625 (9)
C5—C6	1.375 (18)	N2—H2	0.9100
C5—H5	0.9300	O1—S1	1.429 (8)
C6—C7	1.386 (16)	O2—S1	1.427 (9)
C6—H6	0.9300	O4—H4A	0.89 (10)
C7—H7	0.9300	Cd1—N2^i	2.267 (10)
C8—C9	1.37 (3)	Cd1—O4^i	2.317 (8)
C8—O4	1.374 (18)	Cd1—N1^i	2.397 (9)
C8—H8A	0.9700	Cd1—N1	2.397 (9)
C8—H8B	0.9700	Cd1—N2	2.267 (10)
C9—N2	1.41 (2)	Cd1—O4	2.317 (8)
C9—H9A	0.9700
O3—C1—N1	126.0 (11)	C10—C11—H11A	109.5
O3—C1—C2	125.1 (10)	C10—C11—H11B	109.5
N1—C1—C2	108.8 (8)	H11A—C11—H11B	109.5
C3—C2—C7	120.0 (9)	C10—C11—H11C	109.5
C3—C2—C1	113.6 (9)	H11A—C11—H11C	109.5
C7—C2—C1	126.3 (9)	H11B—C11—H11C	109.5
C4—C3—C2	122.4 (10)	C1—N1—S1	113.7 (7)
C4—C3—S1	130.5 (8)	C1—N1—Cd1	118.4 (7)
C2—C3—S1	107.1 (7)	S1—N1—Cd1	125.1 (5)
C3—C4—C5	117.0 (11)	C9—N2—C10	120.7 (13)
C3—C4—H4	121.5	C9—N2—Cd1	109.4 (9)
C5—C4—H4	121.5	C10—N2—Cd1	119.5 (9)
C6—C5—C4	121.8 (11)	C9—N2—H2	100.8
C6—C5—H5	119.1	C10—N2—H2	100.8
C4—C5—H5	119.1	Cd1—N2—H2	100.8
C5—C6—C7	120.8 (11)	C8—O4—Cd1	112.7 (8)
C5—C6—H6	119.6	C8—O4—H4A	112 (10)
C7—C6—H6	119.6	Cd1—O4—H4A	127 (10)
C2—C7—C6	117.9 (10)	O2—S1—O1	115.8 (5)
C2—C7—H7	121.0	O2—S1—N1	111.6 (5)
C6—C7—H7	121.0	O1—S1—N1	110.4 (5)
C9—C8—O4	112.3 (15)	O2—S1—C3	110.2 (5)
C9—C8—H8A	109.1	O1—S1—C3	110.7 (5)
O4—C8—H8A	109.1	N1—S1—C3	96.6 (5)
C9—C8—H8B	109.1	N2^i—Cd1—N2	180.0 (9)
O4—C8—H8B	109.1	N2^i—Cd1—O4^i	72.0 (4)
H8A—C8—H8B	107.9	N2—Cd1—O4^i	108.0 (4)
C8—C9—N2	113.2 (17)	N2^i—Cd1—O4	108.0 (4)
C8—C9—H9A	108.9	N2—Cd1—O4	72.0 (4)
N2—C9—H9A	108.9	O4^i—Cd1—O4	180.0 (4)
C8—C9—H9B	108.9	N2^i—Cd1—N1^i	86.9 (4)
N2—C9—H9B	108.9	N2—Cd1—N1^i	93.1 (4)
H9A—C9—H9B	107.8	O4^i—Cd1—N1^i	94.3 (3)
C11—C10—N2	114.0 (12)	O4—Cd1—N1^i	85.7 (3)
C11—C10—H10A	108.8	N2^i—Cd1—N1	93.1 (4)
N2—C10—H10A	108.8	N2—Cd1—N1	86.9 (4)
C11—C10—H10B	108.8	O4^i—Cd1—N1	85.7 (3)
N2—C10—H10B	108.8	O4—Cd1—N1	94.3 (3)
H10A—C10—H10B	107.6	N1^i—Cd1—N1	180.0 (5)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3^ii	0.89 (10)	1.99 (6)	2.863 (11)	168 (15)
N2—H2···O1	0.91	2.49	3.336 (16)	154

Symmetry code: (ii) −x−1, −y, −z.