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In the title compound, [Cd(C11H13BrClN2O)2]·H2O, both the mononuclear cadmium(II) complex and the solvent water mol­ecule lie on a crystallographic twofold rotation axis, which passes through the metal centre and the O atom of the water mol­ecule. The CdII atom is six-coordinated in a severely distorted octahedral geometry by two phenolate O, two imine N and two amine N atoms from two Schiff base ligands. The water mol­ecule is linked to the CdII complex mol­ecule through O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030826/ci2399sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030826/ci2399Isup2.hkl
Contains datablock I

CCDC reference: 654834

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] 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).
Bis{2-bromo-4-chloro-6-[(2-dimethylaminoethylimino)methyl]phenolato}cadmium(II) monohydrate top
Crystal data top
[Cd(C11H13BrClN2O)2]·H2OF(000) = 1456
Mr = 739.60Dx = 1.826 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 2827 reflections
a = 12.4517 (18) Åθ = 2.5–24.3°
b = 9.2937 (14) ŵ = 4.01 mm1
c = 23.254 (4) ÅT = 298 K
V = 2691.1 (7) Å3Block, colourless
Z = 40.32 × 0.30 × 0.27 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3076 independent reflections
Radiation source: fine-focus sealed tube2184 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.293, Tmax = 0.331k = 1111
21549 measured reflectionsl = 3029
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H 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 parametersΔρmax = 0.62 e Å3
1 restraintΔρmin = 0.58 e Å3
Crystal data top
[Cd(C11H13BrClN2O)2]·H2OV = 2691.1 (7) Å3
Mr = 739.60Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 12.4517 (18) ŵ = 4.01 mm1
b = 9.2937 (14) ÅT = 298 K
c = 23.254 (4) Å0.32 × 0.30 × 0.27 mm
Data collection top
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 = 0.331Rint = 0.067
21549 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.62 e Å3
3076 reflectionsΔρmin = 0.58 e Å3
160 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
Cd10.00000.16643 (4)0.25000.03424 (12)
Br10.05873 (5)0.18375 (6)0.41005 (2)0.07325 (19)
Cl10.31949 (15)0.02044 (18)0.51342 (6)0.1009 (6)
O10.0340 (2)0.0093 (3)0.31307 (11)0.0424 (7)
O20.00000.7240 (5)0.25000.0646 (12)
N10.1798 (3)0.2104 (4)0.26903 (15)0.0417 (8)
N20.0692 (3)0.3193 (4)0.17098 (15)0.0447 (8)
C10.1937 (3)0.0785 (4)0.35954 (17)0.0406 (9)
C20.0964 (3)0.0023 (4)0.35705 (17)0.0394 (9)
C30.0726 (4)0.0801 (4)0.40812 (18)0.0477 (11)
C40.1371 (5)0.0844 (5)0.45538 (18)0.0585 (13)
H40.11710.13670.48780.070*
C50.2326 (4)0.0096 (6)0.45414 (19)0.0593 (13)
C60.2605 (4)0.0715 (5)0.40785 (19)0.0545 (12)
H60.32460.12280.40830.065*
C70.2305 (3)0.1734 (4)0.31383 (18)0.0455 (10)
H70.29920.21120.31800.055*
C80.2352 (4)0.3090 (5)0.2292 (2)0.0542 (12)
H8A0.27600.25350.20140.065*
H8B0.28520.36870.25050.065*
C90.1559 (4)0.4034 (5)0.1981 (2)0.0549 (12)
H9A0.12490.47110.22510.066*
H9B0.19330.45810.16880.066*
C100.1122 (4)0.2283 (6)0.1254 (2)0.0680 (15)
H10A0.05410.18720.10380.102*
H10B0.15460.15260.14200.102*
H10C0.15640.28510.10030.102*
C110.0104 (4)0.4182 (6)0.1473 (2)0.0741 (16)
H11A0.02250.47710.11830.111*
H11B0.03790.47840.17750.111*
H11C0.06830.36430.13060.111*
H20.002 (5)0.783 (4)0.2779 (15)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0320 (2)0.0349 (2)0.0359 (2)0.0000.00174 (18)0.000
Br10.0855 (4)0.0647 (3)0.0695 (4)0.0195 (3)0.0068 (3)0.0153 (3)
Cl10.1271 (14)0.1097 (13)0.0658 (9)0.0133 (11)0.0591 (9)0.0031 (8)
O10.0469 (16)0.0394 (15)0.0407 (16)0.0071 (13)0.0115 (13)0.0045 (12)
O20.065 (3)0.052 (3)0.077 (4)0.0000.003 (3)0.000
N10.0326 (18)0.045 (2)0.048 (2)0.0032 (15)0.0034 (15)0.0044 (15)
N20.046 (2)0.043 (2)0.046 (2)0.0001 (17)0.0015 (16)0.0080 (16)
C10.043 (2)0.037 (2)0.042 (2)0.0086 (19)0.0100 (19)0.0043 (18)
C20.043 (2)0.032 (2)0.043 (2)0.0052 (18)0.0038 (18)0.0039 (18)
C30.063 (3)0.035 (2)0.045 (2)0.002 (2)0.001 (2)0.0033 (19)
C40.091 (4)0.052 (3)0.032 (2)0.011 (3)0.006 (2)0.005 (2)
C50.079 (4)0.056 (3)0.042 (3)0.018 (3)0.024 (2)0.007 (2)
C60.055 (3)0.049 (3)0.059 (3)0.011 (2)0.019 (2)0.009 (2)
C70.033 (2)0.044 (2)0.059 (3)0.0027 (19)0.005 (2)0.010 (2)
C80.042 (3)0.061 (3)0.059 (3)0.010 (2)0.003 (2)0.009 (2)
C90.057 (3)0.047 (3)0.061 (3)0.009 (2)0.007 (2)0.007 (2)
C100.089 (4)0.066 (3)0.049 (3)0.017 (3)0.014 (3)0.001 (2)
C110.059 (3)0.078 (4)0.085 (4)0.007 (3)0.002 (3)0.043 (3)
Geometric parameters (Å, º) top
Cd1—O1i2.236 (3)C2—C31.421 (6)
Cd1—O12.236 (3)C3—C41.361 (6)
Cd1—N12.319 (3)C4—C51.378 (7)
Cd1—N1i2.319 (3)C4—H40.93
Cd1—N2i2.477 (3)C5—C61.359 (7)
Cd1—N22.477 (3)C6—H60.93
Br1—C31.899 (5)C7—H70.93
Cl1—C51.756 (4)C8—C91.505 (6)
O1—C21.286 (4)C8—H8A0.97
O2—H20.85 (4)C8—H8B0.97
N1—C71.266 (5)C9—H9A0.97
N1—C81.475 (5)C9—H9B0.97
N2—C101.459 (6)C10—H10A0.96
N2—C111.459 (6)C10—H10B0.96
N2—C91.475 (5)C10—H10C0.96
C1—C61.400 (5)C11—H11A0.96
C1—C21.426 (6)C11—H11B0.96
C1—C71.455 (6)C11—H11C0.96
O1i—Cd1—O186.12 (14)C3—C4—H4120.8
O1i—Cd1—N1115.90 (11)C5—C4—H4120.8
O1—Cd1—N179.68 (10)C6—C5—C4121.2 (4)
O1i—Cd1—N1i79.68 (10)C6—C5—Cl1119.7 (4)
O1—Cd1—N1i115.90 (11)C4—C5—Cl1119.1 (4)
N1—Cd1—N1i159.69 (16)C5—C6—C1120.6 (5)
O1i—Cd1—N2i147.12 (11)C5—C6—H6119.7
O1—Cd1—N2i89.90 (11)C1—C6—H6119.7
N1—Cd1—N2i95.34 (12)N1—C7—C1127.5 (4)
N1i—Cd1—N2i72.83 (11)N1—C7—H7116.3
O1i—Cd1—N289.90 (11)C1—C7—H7116.3
O1—Cd1—N2147.12 (11)N1—C8—C9110.9 (4)
N1—Cd1—N272.83 (11)N1—C8—H8A109.5
N1i—Cd1—N295.34 (12)C9—C8—H8A109.5
N2i—Cd1—N2110.01 (16)N1—C8—H8B109.5
C2—O1—Cd1126.8 (2)C9—C8—H8B109.5
C7—N1—C8116.9 (4)H8A—C8—H8B108.0
C7—N1—Cd1126.2 (3)N2—C9—C8112.1 (4)
C8—N1—Cd1116.2 (3)N2—C9—H9A109.2
C10—N2—C11109.9 (4)C8—C9—H9A109.2
C10—N2—C9110.4 (4)N2—C9—H9B109.2
C11—N2—C9108.9 (4)C8—C9—H9B109.2
C10—N2—Cd1109.6 (3)H9A—C9—H9B107.9
C11—N2—Cd1113.9 (3)N2—C10—H10A109.5
C9—N2—Cd1104.0 (2)N2—C10—H10B109.5
C6—C1—C2120.9 (4)H10A—C10—H10B109.5
C6—C1—C7115.3 (4)N2—C10—H10C109.5
C2—C1—C7123.9 (4)H10A—C10—H10C109.5
O1—C2—C3120.8 (4)H10B—C10—H10C109.5
O1—C2—C1124.9 (4)N2—C11—H11A109.5
C3—C2—C1114.3 (4)N2—C11—H11B109.5
C4—C3—C2124.5 (4)H11A—C11—H11B109.5
C4—C3—Br1118.3 (4)N2—C11—H11C109.5
C2—C3—Br1117.2 (3)H11A—C11—H11C109.5
C3—C4—C5118.5 (4)H11B—C11—H11C109.5
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1ii0.85 (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
Mr739.60
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)298
a, b, c (Å)12.4517 (18), 9.2937 (14), 23.254 (4)
V3)2691.1 (7)
Z4
Radiation typeMo Kα
µ (mm1)4.01
Crystal size (mm)0.32 × 0.30 × 0.27
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.293, 0.331
No. of measured, independent and
observed [I > 2σ(I)] reflections
21549, 3076, 2184
Rint0.067
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.087, 1.02
No. of reflections3076
No. of parameters160
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.62, 0.58

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected geometric parameters (Å, º) top
Cd1—O12.236 (3)Cd1—N22.477 (3)
Cd1—N12.319 (3)
O1i—Cd1—O186.12 (14)N1—Cd1—N2i95.34 (12)
O1—Cd1—N179.68 (10)O1—Cd1—N2147.12 (11)
O1—Cd1—N1i115.90 (11)N1—Cd1—N272.83 (11)
N1—Cd1—N1i159.69 (16)N2i—Cd1—N2110.01 (16)
O1—Cd1—N2i89.90 (11)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1ii0.85 (4)2.14 (3)2.911 (5)152 (5)
Symmetry code: (ii) x, y+1, z.
 

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