Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056036/hb2635sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056036/hb2635Isup2.hkl |
CCDC reference: 672616
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.018 Å
- R factor = 0.049
- wR factor = 0.135
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
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
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).
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.
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).
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).
[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) Å3 | 0.21 × 0.19 × 0.18 mm |
Z = 2 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.085P)2] where P = (Fo2 + 2Fc2)/3 |
2980 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 1.42 e Å−3 |
3 restraints | Δρmin = −1.17 e Å−3 |
[Cd(C7H4NO3S)2(C4H11NO)2] | V = 1322.4 (2) Å3 |
Mr = 655.05 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.7961 (6) Å | µ = 1.04 mm−1 |
b = 19.2676 (19) Å | T = 296 K |
c = 8.8162 (7) Å | 0.21 × 0.19 × 0.18 mm |
β = 93.061 (6)° |
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 = 0.822 | Rint = 0.076 |
21045 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 1.42 e Å−3 |
2980 reflections | Δρmin = −1.17 e Å−3 |
167 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—N2i | 2.267 (10) |
C8—C9 | 1.37 (3) | Cd1—O4i | 2.317 (8) |
C8—O4 | 1.374 (18) | Cd1—N1i | 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 | N2i—Cd1—N2 | 180.0 (9) |
O4—C8—H8B | 109.1 | N2i—Cd1—O4i | 72.0 (4) |
H8A—C8—H8B | 107.9 | N2—Cd1—O4i | 108.0 (4) |
C8—C9—N2 | 113.2 (17) | N2i—Cd1—O4 | 108.0 (4) |
C8—C9—H9A | 108.9 | N2—Cd1—O4 | 72.0 (4) |
N2—C9—H9A | 108.9 | O4i—Cd1—O4 | 180.0 (4) |
C8—C9—H9B | 108.9 | N2i—Cd1—N1i | 86.9 (4) |
N2—C9—H9B | 108.9 | N2—Cd1—N1i | 93.1 (4) |
H9A—C9—H9B | 107.8 | O4i—Cd1—N1i | 94.3 (3) |
C11—C10—N2 | 114.0 (12) | O4—Cd1—N1i | 85.7 (3) |
C11—C10—H10A | 108.8 | N2i—Cd1—N1 | 93.1 (4) |
N2—C10—H10A | 108.8 | N2—Cd1—N1 | 86.9 (4) |
C11—C10—H10B | 108.8 | O4i—Cd1—N1 | 85.7 (3) |
N2—C10—H10B | 108.8 | O4—Cd1—N1 | 94.3 (3) |
H10A—C10—H10B | 107.6 | N1i—Cd1—N1 | 180.0 (5) |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O3ii | 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. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C7H4NO3S)2(C4H11NO)2] |
Mr | 655.05 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.7961 (6), 19.2676 (19), 8.8162 (7) |
β (°) | 93.061 (6) |
V (Å3) | 1322.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.04 |
Crystal size (mm) | 0.21 × 0.19 × 0.18 |
Data collection | |
Diffractometer | STOE IPDS 2 diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.783, 0.822 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21045, 2980, 2013 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.646 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.135, 0.96 |
No. of reflections | 2980 |
No. of parameters | 167 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.42, −1.17 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP 3 (Farrugia, 1997), WinGX (Farrugia, 19993).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O3i | 0.89 (10) | 1.99 (6) | 2.863 (11) | 168 (15) |
N2—H2···O1 | 0.91 | 2.49 | 3.336 (16) | 154 |
Symmetry code: (i) −x−1, −y, −z. |
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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.