Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030826/ci2399sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030826/ci2399Isup2.hkl |
CCDC reference: 654834
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.039
- wR factor = 0.087
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 2.07 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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 literature, see: Cai et al. (2006); Cao (2007); Chakraborty et al. (2007); Das et al. (2007); Ghosh et al. (2007); Keypour et al. (2007); Li & Wang (2007a,b); Li & You (2007); Rahaman et al. (2006); Shashidhar et al. (2007); Wang & Li (2007); You et al. (2006).
3-Bromo-5-chlorosalicylaldehyde (0.2 mmol, 47.0 mg) and N,N-dimethyl-1,2-diaminoethane (0.2 mmol, 17.6 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred at room temperature for 30 min, giving a clear yellow solution. To this solution was added an aqueous solution (2 ml) of Cd(NO3)2·4H2O (0.1 mmol, 30.8 mg) with stirring. The resulting mixture was stirred for a further 30 min at room temperature, giving a clear colourless solution. After allowing the solution to stand in air for a week, colourless block-shaped crystals were formed.
Atom H2 was located from a difference Fourier map and its positional parameters were refined, with thw O—H distance restrained to 0.85 (1) Å. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Cadmium complexes derived from Schiff bases have been widely studied for their structures and applications (Shashidhar et al., 2007; Keypour et al., 2007; Cao, 2007; Das et al., 2007; Chakraborty et al., 2007). Recently, we have reported a few transition metal complexes derived from Schiff bases (Li & Wang, 2007a,b; Li & You, 2007; Wang & Li, 2007). As a further investigation of the work on the structural characterization of such complexes, the title cadmium(II) complex, (I), is reported here.
The asymmetric unit of (I) contains one-half of the mononuclear cadmium(II) complex, with the other half related by a crystallographic twofold axis passing through the metal atom; the lattice water molecule also lies on the twofold axis (Fig. 1). The CdII atom is six-coordinated in an anti-trigonal bipyramidal geometry by two phenolate O, two imine N and two amine N atoms from two Schiff base ligands. The Cd—O and Cd—N bond lengths (Table 1) are comparable to the corresponding values observed in other Schiff base cadmium(II) complexes (Ghosh et al., 2007; Rahaman et al., 2006; You et al., 2006; Cai et al., 2006).
The water molecule is linked to the CdII complex molecule through O—H···O hydrogen bonds (Table 2).
For related literature, see: Cai et al. (2006); Cao (2007); Chakraborty et al. (2007); Das et al. (2007); Ghosh et al. (2007); Keypour et al. (2007); Li & Wang (2007a,b); Li & You (2007); Rahaman et al. (2006); Shashidhar et al. (2007); Wang & Li (2007); You et al. (2006).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. unlabelled atoms are related to labelled atoms by the symmetry operation (-x, y, 1/2 - z). |
[Cd(C11H13BrClN2O)2]·H2O | F(000) = 1456 |
Mr = 739.60 | Dx = 1.826 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 2827 reflections |
a = 12.4517 (18) Å | θ = 2.5–24.3° |
b = 9.2937 (14) Å | µ = 4.01 mm−1 |
c = 23.254 (4) Å | T = 298 K |
V = 2691.1 (7) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.30 × 0.27 mm |
Bruker SMART CCD area-detector diffractometer | 3076 independent reflections |
Radiation source: fine-focus sealed tube | 2184 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.293, Tmax = 0.331 | k = −11→11 |
21549 measured reflections | l = −30→29 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0149P)2 + 3.7768P] where P = (Fo2 + 2Fc2)/3 |
3076 reflections | (Δ/σ)max = 0.001 |
160 parameters | Δρmax = 0.62 e Å−3 |
1 restraint | Δρmin = −0.58 e Å−3 |
[Cd(C11H13BrClN2O)2]·H2O | V = 2691.1 (7) Å3 |
Mr = 739.60 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 12.4517 (18) Å | µ = 4.01 mm−1 |
b = 9.2937 (14) Å | T = 298 K |
c = 23.254 (4) Å | 0.32 × 0.30 × 0.27 mm |
Bruker SMART CCD area-detector diffractometer | 3076 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2184 reflections with I > 2σ(I) |
Tmin = 0.293, Tmax = 0.331 | Rint = 0.067 |
21549 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.62 e Å−3 |
3076 reflections | Δρmin = −0.58 e Å−3 |
160 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 | ||
Cd1 | 0.0000 | 0.16643 (4) | 0.2500 | 0.03424 (12) | |
Br1 | −0.05873 (5) | −0.18375 (6) | 0.41005 (2) | 0.07325 (19) | |
Cl1 | 0.31949 (15) | −0.02044 (18) | 0.51342 (6) | 0.1009 (6) | |
O1 | 0.0340 (2) | −0.0093 (3) | 0.31307 (11) | 0.0424 (7) | |
O2 | 0.0000 | 0.7240 (5) | 0.2500 | 0.0646 (12) | |
N1 | 0.1798 (3) | 0.2104 (4) | 0.26903 (15) | 0.0417 (8) | |
N2 | 0.0692 (3) | 0.3193 (4) | 0.17098 (15) | 0.0447 (8) | |
C1 | 0.1937 (3) | 0.0785 (4) | 0.35954 (17) | 0.0406 (9) | |
C2 | 0.0964 (3) | −0.0023 (4) | 0.35705 (17) | 0.0394 (9) | |
C3 | 0.0726 (4) | −0.0801 (4) | 0.40812 (18) | 0.0477 (11) | |
C4 | 0.1371 (5) | −0.0844 (5) | 0.45538 (18) | 0.0585 (13) | |
H4 | 0.1171 | −0.1367 | 0.4878 | 0.070* | |
C5 | 0.2326 (4) | −0.0096 (6) | 0.45414 (19) | 0.0593 (13) | |
C6 | 0.2605 (4) | 0.0715 (5) | 0.40785 (19) | 0.0545 (12) | |
H6 | 0.3246 | 0.1228 | 0.4083 | 0.065* | |
C7 | 0.2305 (3) | 0.1734 (4) | 0.31383 (18) | 0.0455 (10) | |
H7 | 0.2992 | 0.2112 | 0.3180 | 0.055* | |
C8 | 0.2352 (4) | 0.3090 (5) | 0.2292 (2) | 0.0542 (12) | |
H8A | 0.2760 | 0.2535 | 0.2014 | 0.065* | |
H8B | 0.2852 | 0.3687 | 0.2505 | 0.065* | |
C9 | 0.1559 (4) | 0.4034 (5) | 0.1981 (2) | 0.0549 (12) | |
H9A | 0.1249 | 0.4711 | 0.2251 | 0.066* | |
H9B | 0.1933 | 0.4581 | 0.1688 | 0.066* | |
C10 | 0.1122 (4) | 0.2283 (6) | 0.1254 (2) | 0.0680 (15) | |
H10A | 0.0541 | 0.1872 | 0.1038 | 0.102* | |
H10B | 0.1546 | 0.1526 | 0.1420 | 0.102* | |
H10C | 0.1564 | 0.2851 | 0.1003 | 0.102* | |
C11 | −0.0104 (4) | 0.4182 (6) | 0.1473 (2) | 0.0741 (16) | |
H11A | 0.0225 | 0.4771 | 0.1183 | 0.111* | |
H11B | −0.0379 | 0.4784 | 0.1775 | 0.111* | |
H11C | −0.0683 | 0.3643 | 0.1306 | 0.111* | |
H2 | 0.002 (5) | 0.783 (4) | 0.2779 (15) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0320 (2) | 0.0349 (2) | 0.0359 (2) | 0.000 | −0.00174 (18) | 0.000 |
Br1 | 0.0855 (4) | 0.0647 (3) | 0.0695 (4) | −0.0195 (3) | 0.0068 (3) | 0.0153 (3) |
Cl1 | 0.1271 (14) | 0.1097 (13) | 0.0658 (9) | 0.0133 (11) | −0.0591 (9) | 0.0031 (8) |
O1 | 0.0469 (16) | 0.0394 (15) | 0.0407 (16) | −0.0071 (13) | −0.0115 (13) | 0.0045 (12) |
O2 | 0.065 (3) | 0.052 (3) | 0.077 (4) | 0.000 | −0.003 (3) | 0.000 |
N1 | 0.0326 (18) | 0.045 (2) | 0.048 (2) | −0.0032 (15) | 0.0034 (15) | 0.0044 (15) |
N2 | 0.046 (2) | 0.043 (2) | 0.046 (2) | −0.0001 (17) | 0.0015 (16) | 0.0080 (16) |
C1 | 0.043 (2) | 0.037 (2) | 0.042 (2) | 0.0086 (19) | −0.0100 (19) | −0.0043 (18) |
C2 | 0.043 (2) | 0.032 (2) | 0.043 (2) | 0.0052 (18) | −0.0038 (18) | −0.0039 (18) |
C3 | 0.063 (3) | 0.035 (2) | 0.045 (2) | 0.002 (2) | −0.001 (2) | 0.0033 (19) |
C4 | 0.091 (4) | 0.052 (3) | 0.032 (2) | 0.011 (3) | −0.006 (2) | 0.005 (2) |
C5 | 0.079 (4) | 0.056 (3) | 0.042 (3) | 0.018 (3) | −0.024 (2) | −0.007 (2) |
C6 | 0.055 (3) | 0.049 (3) | 0.059 (3) | 0.011 (2) | −0.019 (2) | −0.009 (2) |
C7 | 0.033 (2) | 0.044 (2) | 0.059 (3) | −0.0027 (19) | −0.005 (2) | −0.010 (2) |
C8 | 0.042 (3) | 0.061 (3) | 0.059 (3) | −0.010 (2) | 0.003 (2) | 0.009 (2) |
C9 | 0.057 (3) | 0.047 (3) | 0.061 (3) | −0.009 (2) | 0.007 (2) | 0.007 (2) |
C10 | 0.089 (4) | 0.066 (3) | 0.049 (3) | −0.017 (3) | 0.014 (3) | 0.001 (2) |
C11 | 0.059 (3) | 0.078 (4) | 0.085 (4) | 0.007 (3) | 0.002 (3) | 0.043 (3) |
Cd1—O1i | 2.236 (3) | C2—C3 | 1.421 (6) |
Cd1—O1 | 2.236 (3) | C3—C4 | 1.361 (6) |
Cd1—N1 | 2.319 (3) | C4—C5 | 1.378 (7) |
Cd1—N1i | 2.319 (3) | C4—H4 | 0.93 |
Cd1—N2i | 2.477 (3) | C5—C6 | 1.359 (7) |
Cd1—N2 | 2.477 (3) | C6—H6 | 0.93 |
Br1—C3 | 1.899 (5) | C7—H7 | 0.93 |
Cl1—C5 | 1.756 (4) | C8—C9 | 1.505 (6) |
O1—C2 | 1.286 (4) | C8—H8A | 0.97 |
O2—H2 | 0.85 (4) | C8—H8B | 0.97 |
N1—C7 | 1.266 (5) | C9—H9A | 0.97 |
N1—C8 | 1.475 (5) | C9—H9B | 0.97 |
N2—C10 | 1.459 (6) | C10—H10A | 0.96 |
N2—C11 | 1.459 (6) | C10—H10B | 0.96 |
N2—C9 | 1.475 (5) | C10—H10C | 0.96 |
C1—C6 | 1.400 (5) | C11—H11A | 0.96 |
C1—C2 | 1.426 (6) | C11—H11B | 0.96 |
C1—C7 | 1.455 (6) | C11—H11C | 0.96 |
O1i—Cd1—O1 | 86.12 (14) | C3—C4—H4 | 120.8 |
O1i—Cd1—N1 | 115.90 (11) | C5—C4—H4 | 120.8 |
O1—Cd1—N1 | 79.68 (10) | C6—C5—C4 | 121.2 (4) |
O1i—Cd1—N1i | 79.68 (10) | C6—C5—Cl1 | 119.7 (4) |
O1—Cd1—N1i | 115.90 (11) | C4—C5—Cl1 | 119.1 (4) |
N1—Cd1—N1i | 159.69 (16) | C5—C6—C1 | 120.6 (5) |
O1i—Cd1—N2i | 147.12 (11) | C5—C6—H6 | 119.7 |
O1—Cd1—N2i | 89.90 (11) | C1—C6—H6 | 119.7 |
N1—Cd1—N2i | 95.34 (12) | N1—C7—C1 | 127.5 (4) |
N1i—Cd1—N2i | 72.83 (11) | N1—C7—H7 | 116.3 |
O1i—Cd1—N2 | 89.90 (11) | C1—C7—H7 | 116.3 |
O1—Cd1—N2 | 147.12 (11) | N1—C8—C9 | 110.9 (4) |
N1—Cd1—N2 | 72.83 (11) | N1—C8—H8A | 109.5 |
N1i—Cd1—N2 | 95.34 (12) | C9—C8—H8A | 109.5 |
N2i—Cd1—N2 | 110.01 (16) | N1—C8—H8B | 109.5 |
C2—O1—Cd1 | 126.8 (2) | C9—C8—H8B | 109.5 |
C7—N1—C8 | 116.9 (4) | H8A—C8—H8B | 108.0 |
C7—N1—Cd1 | 126.2 (3) | N2—C9—C8 | 112.1 (4) |
C8—N1—Cd1 | 116.2 (3) | N2—C9—H9A | 109.2 |
C10—N2—C11 | 109.9 (4) | C8—C9—H9A | 109.2 |
C10—N2—C9 | 110.4 (4) | N2—C9—H9B | 109.2 |
C11—N2—C9 | 108.9 (4) | C8—C9—H9B | 109.2 |
C10—N2—Cd1 | 109.6 (3) | H9A—C9—H9B | 107.9 |
C11—N2—Cd1 | 113.9 (3) | N2—C10—H10A | 109.5 |
C9—N2—Cd1 | 104.0 (2) | N2—C10—H10B | 109.5 |
C6—C1—C2 | 120.9 (4) | H10A—C10—H10B | 109.5 |
C6—C1—C7 | 115.3 (4) | N2—C10—H10C | 109.5 |
C2—C1—C7 | 123.9 (4) | H10A—C10—H10C | 109.5 |
O1—C2—C3 | 120.8 (4) | H10B—C10—H10C | 109.5 |
O1—C2—C1 | 124.9 (4) | N2—C11—H11A | 109.5 |
C3—C2—C1 | 114.3 (4) | N2—C11—H11B | 109.5 |
C4—C3—C2 | 124.5 (4) | H11A—C11—H11B | 109.5 |
C4—C3—Br1 | 118.3 (4) | N2—C11—H11C | 109.5 |
C2—C3—Br1 | 117.2 (3) | H11A—C11—H11C | 109.5 |
C3—C4—C5 | 118.5 (4) | H11B—C11—H11C | 109.5 |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1ii | 0.85 (4) | 2.14 (3) | 2.911 (5) | 152 (5) |
Symmetry code: (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C11H13BrClN2O)2]·H2O |
Mr | 739.60 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 298 |
a, b, c (Å) | 12.4517 (18), 9.2937 (14), 23.254 (4) |
V (Å3) | 2691.1 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.01 |
Crystal size (mm) | 0.32 × 0.30 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.293, 0.331 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21549, 3076, 2184 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.087, 1.02 |
No. of reflections | 3076 |
No. of parameters | 160 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.62, −0.58 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
Cd1—O1 | 2.236 (3) | Cd1—N2 | 2.477 (3) |
Cd1—N1 | 2.319 (3) | ||
O1i—Cd1—O1 | 86.12 (14) | N1—Cd1—N2i | 95.34 (12) |
O1—Cd1—N1 | 79.68 (10) | O1—Cd1—N2 | 147.12 (11) |
O1—Cd1—N1i | 115.90 (11) | N1—Cd1—N2 | 72.83 (11) |
N1—Cd1—N1i | 159.69 (16) | N2i—Cd1—N2 | 110.01 (16) |
O1—Cd1—N2i | 89.90 (11) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1ii | 0.85 (4) | 2.14 (3) | 2.911 (5) | 152 (5) |
Symmetry code: (ii) x, y+1, z. |
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Cadmium complexes derived from Schiff bases have been widely studied for their structures and applications (Shashidhar et al., 2007; Keypour et al., 2007; Cao, 2007; Das et al., 2007; Chakraborty et al., 2007). Recently, we have reported a few transition metal complexes derived from Schiff bases (Li & Wang, 2007a,b; Li & You, 2007; Wang & Li, 2007). As a further investigation of the work on the structural characterization of such complexes, the title cadmium(II) complex, (I), is reported here.
The asymmetric unit of (I) contains one-half of the mononuclear cadmium(II) complex, with the other half related by a crystallographic twofold axis passing through the metal atom; the lattice water molecule also lies on the twofold axis (Fig. 1). The CdII atom is six-coordinated in an anti-trigonal bipyramidal geometry by two phenolate O, two imine N and two amine N atoms from two Schiff base ligands. The Cd—O and Cd—N bond lengths (Table 1) are comparable to the corresponding values observed in other Schiff base cadmium(II) complexes (Ghosh et al., 2007; Rahaman et al., 2006; You et al., 2006; Cai et al., 2006).
The water molecule is linked to the CdII complex molecule through O—H···O hydrogen bonds (Table 2).