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In the title complex, [NiCl(C9H11NO)2(H2O)3]Cl, the NiII ion is six-coordinated by one Cl atom [Ni—Cl = 2.3712 (11) Å], two O atoms from two 4-(dimethyl­amino)benzaldehyde (L) ligands and three water mol­ecules in a distorted octa­hedral geometry [Ni—O = 2.076 (3)–2.094 (3) Å]. The mean planes of the two L ligands make a dihedral angle of 65.8 (1)°. In the crystal structure, inter­molecular O—H...Cl hydrogen bonds link cations and anions into two-dimensional sheets parallel to the ab plane, with the L ligands protruding above and below.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048684/cv2311sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048684/cv2311Isup2.hkl
Contains datablock I

CCDC reference: 667222

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.108
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.06
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Nickel is vital for organism as a trace element. It often acts as a component or secondary factor of enzyme. In the last two decades, biological inorganic chemistry of nickel has became one of the hottest fields and the coordination chemistry of nickel has made a great progress (Jiang et al., 2003). We report here the synthesis and crystal structure of the title compound, a new nickel(II) complex.

The title complex (Fig.1) consists of cations [Ni(C9H11NO)2(H2O)3Cl]+ and non-coordinating chloride anions. The NiII ion is six-coordinated by one Cl atom, two O atoms of 4-dimethylaminobenzaldehyde molecules and three water molecules in a distorted octahedral geometry.

In the crystal, the intermolecular O—H···Cl hydrogen bonds (Table 1) link cations and anions into two-dimensional sheets parallel to ab plane with the up and down protruding ligands.

Related literature top

For general background, see: Jiang et al. (2003).

Experimental top

Nickel chloride hexahydrate (5 mmol, 1189 mg) in absolute ethanol (15 ml) was added dropwise to an absolute ethanol solution (20 ml) of P-dimethylaminobenzaldehyde (10 mmol, 1492 mg). The mixture was heated under reflux with stirring for 4 h. The solution was kept at room temperature for three weeks, after which large green block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Refinement top

All H-atoms were positioned geometrically (C—H 0.93–0.96 Å, O—H 0.85 Å) and refined using a riding model, with Uiso = 1.2–1.5Ueq(parent atom).

Structure description top

Nickel is vital for organism as a trace element. It often acts as a component or secondary factor of enzyme. In the last two decades, biological inorganic chemistry of nickel has became one of the hottest fields and the coordination chemistry of nickel has made a great progress (Jiang et al., 2003). We report here the synthesis and crystal structure of the title compound, a new nickel(II) complex.

The title complex (Fig.1) consists of cations [Ni(C9H11NO)2(H2O)3Cl]+ and non-coordinating chloride anions. The NiII ion is six-coordinated by one Cl atom, two O atoms of 4-dimethylaminobenzaldehyde molecules and three water molecules in a distorted octahedral geometry.

In the crystal, the intermolecular O—H···Cl hydrogen bonds (Table 1) link cations and anions into two-dimensional sheets parallel to ab plane with the up and down protruding ligands.

For general background, see: Jiang et al. (2003).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Triaquachloridobis[4-(dimethylamino)benzaldehyde-κO]nickel(II) chloride top
Crystal data top
[NiCl(C9H11NO)2(H2O)3]ClF(000) = 1008
Mr = 482.03Dx = 1.454 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3371 reflections
a = 11.632 (3) Åθ = 2.1–27.5°
b = 7.5534 (19) ŵ = 1.15 mm1
c = 25.704 (6) ÅT = 298 K
β = 102.87 (3)°Block, green
V = 2201.6 (9) Å30.38 × 0.19 × 0.16 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
3861 independent reflections
Radiation source: fine-focus sealed tube2471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1013
Tmin = 0.668, Tmax = 0.837k = 88
9852 measured reflectionsl = 3030
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.095P)2 + 4.2002P]
where P = (Fo2 + 2Fc2)/3
3861 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
[NiCl(C9H11NO)2(H2O)3]ClV = 2201.6 (9) Å3
Mr = 482.03Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.632 (3) ŵ = 1.15 mm1
b = 7.5534 (19) ÅT = 298 K
c = 25.704 (6) Å0.38 × 0.19 × 0.16 mm
β = 102.87 (3)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
3861 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2471 reflections with I > 2σ(I)
Tmin = 0.668, Tmax = 0.837Rint = 0.097
9852 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 0.96Δρmax = 0.53 e Å3
3861 reflectionsΔρmin = 0.44 e Å3
253 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
Ni10.31610 (4)0.73333 (6)0.514421 (19)0.02885 (16)
Cl10.52350 (7)0.76902 (13)0.54060 (4)0.0355 (3)
Cl20.09692 (8)0.27614 (14)0.47263 (4)0.0420 (3)
N10.3676 (3)0.8312 (5)0.19083 (13)0.0357 (9)
N20.3835 (3)0.6733 (5)0.84909 (13)0.0414 (9)
O10.3131 (2)0.7215 (4)0.43276 (10)0.0409 (7)
O20.3021 (2)0.7448 (3)0.59345 (10)0.0356 (7)
O30.2972 (2)1.0016 (3)0.51083 (10)0.0415 (8)
H190.35101.05770.50020.062*
H200.23261.04830.49460.062*
O40.3347 (2)0.4651 (3)0.52158 (10)0.0350 (7)
H210.38300.42080.50480.053*
H220.27180.40680.50970.053*
O50.1378 (2)0.6939 (4)0.49070 (10)0.0405 (7)
H230.11520.58960.48110.061*
H240.08570.74270.50440.061*
C10.3864 (3)0.7913 (5)0.41131 (16)0.0369 (10)
H10.45230.84160.43360.044*
C20.3790 (3)0.8017 (5)0.35487 (15)0.0318 (10)
C30.4687 (3)0.8831 (5)0.33590 (16)0.0364 (10)
H3A0.53280.93020.36010.044*
C40.4649 (3)0.8958 (5)0.28259 (16)0.0347 (10)
H4A0.52590.95360.27150.042*
C50.3717 (3)0.8239 (5)0.24395 (16)0.0307 (9)
C60.2794 (3)0.7441 (5)0.26374 (16)0.0375 (11)
H60.21390.69930.23980.045*
C70.2852 (3)0.7321 (5)0.31661 (16)0.0368 (10)
H70.22440.67520.32810.044*
C80.4634 (3)0.9121 (6)0.17189 (16)0.0485 (12)
H8A0.46441.03710.17870.073*
H8B0.45240.89210.13420.073*
H8C0.53680.86080.19010.073*
C90.2689 (4)0.7645 (6)0.15098 (15)0.0533 (13)
H9A0.25790.64100.15730.080*
H9B0.28470.77950.11610.080*
H9C0.19890.82870.15310.080*
C100.3730 (3)0.6683 (5)0.62962 (15)0.0350 (10)
H100.43130.60080.61950.042*
C110.3740 (3)0.6735 (5)0.68512 (15)0.0294 (9)
C120.2921 (3)0.7697 (5)0.70616 (15)0.0331 (10)
H120.23400.83440.68320.040*
C130.2954 (3)0.7707 (5)0.75929 (15)0.0367 (10)
H130.23950.83640.77180.044*
C140.3813 (3)0.6748 (5)0.79631 (16)0.0311 (10)
C150.4646 (3)0.5804 (5)0.77481 (16)0.0361 (11)
H150.52400.51720.79750.043*
C160.4592 (3)0.5804 (5)0.72124 (16)0.0347 (10)
H160.51490.51540.70840.042*
C170.4703 (4)0.5718 (7)0.88665 (16)0.0621 (15)
H17A0.46110.44820.87790.093*
H17B0.45930.59050.92210.093*
H17C0.54810.60940.88470.093*
C180.3019 (4)0.7759 (7)0.87143 (18)0.0772 (18)
H18A0.31980.89950.86950.116*
H18B0.30870.74270.90800.116*
H18C0.22300.75390.85170.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0264 (3)0.0323 (3)0.0302 (3)0.0008 (2)0.01120 (19)0.0021 (3)
Cl10.0274 (5)0.0439 (6)0.0374 (6)0.0022 (4)0.0115 (4)0.0000 (5)
Cl20.0311 (5)0.0508 (7)0.0459 (6)0.0013 (5)0.0125 (4)0.0062 (6)
N10.0366 (18)0.042 (2)0.027 (2)0.0032 (16)0.0047 (15)0.0023 (18)
N20.053 (2)0.047 (2)0.024 (2)0.0080 (18)0.0071 (16)0.0006 (19)
O10.0411 (15)0.0500 (19)0.0353 (17)0.0068 (14)0.0161 (13)0.0011 (16)
O20.0388 (15)0.0413 (18)0.0298 (15)0.0024 (13)0.0142 (12)0.0023 (15)
O30.0348 (15)0.0335 (16)0.059 (2)0.0025 (12)0.0169 (14)0.0110 (15)
O40.0301 (13)0.0331 (16)0.0445 (18)0.0011 (12)0.0138 (12)0.0081 (14)
O50.0260 (13)0.0481 (18)0.0500 (18)0.0022 (13)0.0143 (12)0.0012 (16)
C10.037 (2)0.036 (3)0.038 (3)0.0002 (19)0.0095 (18)0.005 (2)
C20.033 (2)0.035 (2)0.029 (2)0.0019 (18)0.0107 (17)0.001 (2)
C30.034 (2)0.044 (3)0.030 (3)0.0075 (19)0.0048 (18)0.006 (2)
C40.030 (2)0.041 (3)0.035 (3)0.0075 (18)0.0122 (18)0.001 (2)
C50.029 (2)0.030 (2)0.034 (3)0.0000 (17)0.0077 (17)0.002 (2)
C60.032 (2)0.044 (3)0.035 (3)0.0097 (19)0.0033 (17)0.000 (2)
C70.032 (2)0.039 (3)0.041 (3)0.0062 (18)0.0112 (17)0.004 (2)
C80.052 (3)0.063 (3)0.034 (3)0.010 (2)0.018 (2)0.001 (3)
C90.051 (3)0.074 (4)0.032 (3)0.010 (2)0.003 (2)0.005 (3)
C100.035 (2)0.037 (3)0.036 (3)0.0008 (19)0.0148 (19)0.002 (2)
C110.029 (2)0.032 (2)0.028 (2)0.0009 (17)0.0066 (17)0.003 (2)
C120.0303 (19)0.039 (3)0.029 (2)0.0022 (18)0.0040 (16)0.005 (2)
C130.032 (2)0.042 (3)0.037 (3)0.0103 (19)0.0115 (17)0.005 (2)
C140.034 (2)0.027 (2)0.031 (3)0.0046 (18)0.0052 (18)0.000 (2)
C150.033 (2)0.038 (3)0.034 (3)0.0075 (19)0.0024 (18)0.001 (2)
C160.031 (2)0.035 (2)0.040 (3)0.0023 (18)0.0136 (18)0.000 (2)
C170.077 (3)0.072 (4)0.032 (3)0.018 (3)0.000 (2)0.006 (3)
C180.089 (4)0.111 (5)0.036 (3)0.032 (4)0.023 (3)0.000 (3)
Geometric parameters (Å, º) top
Ni1—O32.038 (3)C5—C61.420 (5)
Ni1—O42.042 (3)C6—C71.349 (5)
Ni1—O52.049 (2)C6—H60.9300
Ni1—O22.075 (3)C7—H70.9300
Ni1—O12.094 (3)C8—H8A0.9600
Ni1—Cl12.3712 (11)C8—H8B0.9600
N1—C51.357 (5)C8—H8C0.9600
N1—C81.447 (5)C9—H9A0.9600
N1—C91.448 (4)C9—H9B0.9600
N2—C141.351 (5)C9—H9C0.9600
N2—C181.439 (5)C10—C111.425 (5)
N2—C171.451 (5)C10—H100.9300
O1—C11.232 (4)C11—C161.389 (5)
O2—C101.240 (4)C11—C121.399 (5)
O3—H190.8500C12—C131.357 (5)
O3—H200.8500C12—H120.9300
O4—H210.8500C13—C141.416 (5)
O4—H220.8501C13—H130.9300
O5—H230.8500C14—C151.411 (5)
O5—H240.8499C15—C161.364 (5)
C1—C21.436 (5)C15—H150.9300
C1—H10.9300C16—H160.9300
C2—C31.390 (5)C17—H17A0.9600
C2—C71.398 (5)C17—H17B0.9600
C3—C41.365 (5)C17—H17C0.9600
C3—H3A0.9300C18—H18A0.9600
C4—C51.406 (5)C18—H18B0.9600
C4—H4A0.9300C18—H18C0.9600
O3—Ni1—O4177.40 (10)C5—C6—H6119.4
O3—Ni1—O592.24 (10)C6—C7—C2122.7 (4)
O4—Ni1—O587.84 (10)C6—C7—H7118.7
O3—Ni1—O288.37 (11)C2—C7—H7118.7
O4—Ni1—O289.02 (10)N1—C8—H8A109.5
O5—Ni1—O290.15 (10)N1—C8—H8B109.5
O3—Ni1—O191.12 (11)H8A—C8—H8B109.5
O4—Ni1—O191.48 (10)N1—C8—H8C109.5
O5—Ni1—O184.59 (10)H8A—C8—H8C109.5
O2—Ni1—O1174.70 (10)H8B—C8—H8C109.5
O3—Ni1—Cl189.57 (7)N1—C9—H9A109.5
O4—Ni1—Cl190.39 (7)N1—C9—H9B109.5
O5—Ni1—Cl1177.98 (8)H9A—C9—H9B109.5
O2—Ni1—Cl190.79 (8)N1—C9—H9C109.5
O1—Ni1—Cl194.48 (8)H9A—C9—H9C109.5
C5—N1—C8119.9 (3)H9B—C9—H9C109.5
C5—N1—C9122.8 (3)O2—C10—C11126.4 (4)
C8—N1—C9117.2 (3)O2—C10—H10116.8
C14—N2—C18122.0 (3)C11—C10—H10116.8
C14—N2—C17121.8 (4)C16—C11—C12116.8 (3)
C18—N2—C17116.2 (4)C16—C11—C10120.0 (4)
C1—O1—Ni1124.9 (3)C12—C11—C10123.2 (3)
C10—O2—Ni1122.1 (2)C13—C12—C11121.5 (3)
Ni1—O3—H19115.5C13—C12—H12119.3
Ni1—O3—H20120.7C11—C12—H12119.3
H19—O3—H20105.6C12—C13—C14122.1 (4)
Ni1—O4—H21114.4C12—C13—H13119.0
Ni1—O4—H22114.6C14—C13—H13119.0
H21—O4—H22103.1N2—C14—C15121.9 (4)
Ni1—O5—H23116.6N2—C14—C13122.1 (4)
Ni1—O5—H24125.6C15—C14—C13116.0 (4)
H23—O5—H24108.6C16—C15—C14120.9 (4)
O1—C1—C2125.7 (4)C16—C15—H15119.5
O1—C1—H1117.2C14—C15—H15119.5
C2—C1—H1117.2C15—C16—C11122.7 (4)
C3—C2—C7116.6 (4)C15—C16—H16118.7
C3—C2—C1119.8 (4)C11—C16—H16118.7
C7—C2—C1123.5 (3)N2—C17—H17A109.5
C4—C3—C2121.7 (4)N2—C17—H17B109.5
C4—C3—H3A119.2H17A—C17—H17B109.5
C2—C3—H3A119.2N2—C17—H17C109.5
C3—C4—C5122.0 (4)H17A—C17—H17C109.5
C3—C4—H4A119.0H17B—C17—H17C109.5
C5—C4—H4A119.0N2—C18—H18A109.5
N1—C5—C4122.9 (3)N2—C18—H18B109.5
N1—C5—C6121.2 (3)H18A—C18—H18B109.5
C4—C5—C6115.9 (4)N2—C18—H18C109.5
C7—C6—C5121.1 (3)H18A—C18—H18C109.5
C7—C6—H6119.4H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H19···Cl1i0.852.373.214 (3)171
O3—H20···Cl2ii0.852.323.110 (3)155
O4—H21···Cl1iii0.852.273.095 (3)163
O5—H24···Cl2iv0.852.333.088 (3)149
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[NiCl(C9H11NO)2(H2O)3]Cl
Mr482.03
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)11.632 (3), 7.5534 (19), 25.704 (6)
β (°) 102.87 (3)
V3)2201.6 (9)
Z4
Radiation typeMo Kα
µ (mm1)1.15
Crystal size (mm)0.38 × 0.19 × 0.16
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.668, 0.837
No. of measured, independent and
observed [I > 2σ(I)] reflections
9852, 3861, 2471
Rint0.097
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.109, 0.96
No. of reflections3861
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.44

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H19···Cl1i0.852.373.214 (3)170.9
O3—H20···Cl2ii0.852.323.110 (3)155.1
O4—H21···Cl1iii0.852.273.095 (3)162.8
O5—H24···Cl2iv0.852.333.088 (3)148.5
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1.
 

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