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In the crystal structure of the title compound, [Ni(C10H12N3O2S)2]·H2O, the NiII atom is located on an inversion center and is chelated by two hydroxy­ethoxy­benzaldehyde thio­semicarbazonate anions in a square-planar geometry. The five-membered chelate ring assumes an envelope conformation, with the Ni atom lying at the flap position. The uncoordinated water mol­ecule is disordered over another inversion center and is hydrogen bonded to the NiII complex.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008348/xu2008sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008348/xu2008Isup2.hkl
Contains datablock I

CCDC reference: 605218

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 93%
  • R factor = 0.053
  • wR factor = 0.142
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O3
Author Response: As the lattice water is located on an inversion center, H atoms of the water molecule were not resasonably located.

Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.28 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H26 N6 Ni1 O5 S2 Atom count from the _atom_site data: C20 H24 N6 Ni1 O5 S2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 1 From the CIF: _chemical_formula_sum C20 H26 N6 Ni O5 S2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 20.00 20.00 0.00 H 26.00 24.00 2.00 N 6.00 6.00 0.00 Ni 1.00 1.00 0.00 O 5.00 5.00 0.00 S 2.00 2.00 0.00
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(3-ethoxy-4-hydroxybenzaldehyde thiosemicarbazonato-κ2S,N)nickel(II) monohydrate top
Crystal data top
[Ni(C10H12N3O2S)2]·H2OZ = 1
Mr = 553.30F(000) = 288
Triclinic, P1Dx = 1.585 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.794 (3) ÅCell parameters from 728 reflections
b = 10.222 (4) Åθ = 2.5–21.7°
c = 10.227 (5) ŵ = 1.06 mm1
α = 75.100 (7)°T = 294 K
β = 87.398 (6)°Prism, red
γ = 81.956 (6)°0.27 × 0.13 × 0.04 mm
V = 579.6 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2015 independent reflections
Radiation source: fine-focus sealed tube1593 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 66
Tmin = 0.763, Tmax = 0.957k = 129
2904 measured reflectionsl = 1112
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.082P)2 + 0.1304P]
where P = (Fo2 + 2Fc2)/3
2015 reflections(Δ/σ)max = 0.002
158 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.42 e Å3
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
Ni10.00001.00000.00000.0307 (3)
S10.01427 (18)1.14248 (11)0.12612 (12)0.0415 (3)
O11.1889 (6)0.4528 (3)0.3081 (3)0.0552 (9)
H1C1.24710.49870.36600.066*
O21.0857 (5)0.6868 (3)0.3832 (3)0.0436 (8)
O30.50000.50000.50000.0858 (18)
N10.3615 (7)1.1694 (4)0.2502 (4)0.0565 (12)
H1A0.27401.24380.25840.068*
H1B0.50751.14680.28490.068*
N20.3949 (6)0.9844 (3)0.1666 (4)0.0380 (9)
N30.2803 (5)0.9129 (3)0.0951 (3)0.0332 (8)
C10.9943 (7)0.5400 (4)0.2596 (5)0.0423 (11)
C20.8559 (8)0.5058 (4)0.1719 (5)0.0505 (13)
H20.89660.42500.14550.061*
C30.6577 (8)0.5906 (4)0.1232 (5)0.0478 (12)
H30.56320.56520.06530.057*
C40.5941 (7)0.7129 (4)0.1577 (4)0.0350 (10)
C50.3798 (7)0.7927 (4)0.0965 (4)0.0382 (10)
H50.29940.74720.04910.046*
C60.7382 (7)0.7487 (4)0.2449 (4)0.0357 (10)
H60.70170.83150.26790.043*
C70.9340 (7)0.6617 (4)0.2970 (4)0.0347 (10)
C81.0290 (8)0.8076 (4)0.4286 (5)0.0457 (11)
H8A0.88440.80440.48020.055*
H8B1.00990.88700.35190.055*
C91.2240 (9)0.8159 (5)0.5151 (5)0.0602 (14)
H9A1.23990.73750.59120.090*
H9B1.19130.89740.54660.090*
H9C1.36630.81820.46320.090*
C100.2682 (7)1.0926 (4)0.1823 (4)0.0395 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0301 (4)0.0304 (4)0.0334 (5)0.0018 (3)0.0087 (3)0.0131 (3)
S10.0378 (6)0.0415 (7)0.0498 (7)0.0093 (5)0.0166 (5)0.0249 (5)
O10.0512 (19)0.0416 (18)0.077 (2)0.0150 (15)0.0241 (17)0.0292 (17)
O20.0410 (17)0.0397 (17)0.0530 (19)0.0115 (13)0.0238 (15)0.0221 (15)
O30.071 (4)0.082 (4)0.104 (5)0.010 (3)0.025 (3)0.030 (4)
N10.049 (2)0.050 (2)0.080 (3)0.0127 (19)0.036 (2)0.037 (2)
N20.0353 (19)0.038 (2)0.044 (2)0.0012 (16)0.0154 (16)0.0180 (17)
N30.0308 (17)0.0348 (19)0.0361 (19)0.0025 (15)0.0129 (15)0.0143 (15)
C10.040 (2)0.033 (2)0.054 (3)0.0098 (19)0.011 (2)0.015 (2)
C20.053 (3)0.035 (2)0.070 (3)0.008 (2)0.024 (3)0.028 (2)
C30.050 (3)0.041 (3)0.059 (3)0.000 (2)0.023 (2)0.024 (2)
C40.035 (2)0.027 (2)0.042 (2)0.0042 (17)0.0069 (19)0.0121 (19)
C50.043 (2)0.038 (2)0.038 (2)0.0033 (19)0.0087 (19)0.0160 (19)
C60.039 (2)0.030 (2)0.040 (2)0.0033 (18)0.0097 (19)0.0159 (19)
C70.036 (2)0.034 (2)0.036 (2)0.0014 (18)0.0066 (19)0.0117 (19)
C80.052 (3)0.041 (3)0.047 (3)0.005 (2)0.013 (2)0.019 (2)
C90.063 (3)0.066 (3)0.060 (3)0.001 (3)0.023 (3)0.031 (3)
C100.040 (2)0.037 (2)0.044 (3)0.0031 (19)0.015 (2)0.016 (2)
Geometric parameters (Å, º) top
Ni1—S1i2.1712 (12)C1—C71.388 (5)
Ni1—S12.1712 (12)C2—C31.367 (6)
Ni1—N31.916 (3)C2—H20.9300
Ni1—N3i1.916 (3)C3—C41.383 (5)
S1—C101.723 (4)C3—H30.9300
O1—C11.361 (5)C4—C61.396 (5)
O1—H1C0.9432C4—C51.457 (5)
O2—C71.366 (5)C5—H50.9300
O2—C81.420 (5)C6—C71.375 (5)
N1—C101.350 (5)C6—H60.9300
N1—H1A0.8741C8—C91.491 (6)
N1—H1B0.9082C8—H8A0.9700
N2—C101.282 (5)C8—H8B0.9700
N2—N31.402 (4)C9—H9A0.9600
N3—C51.279 (5)C9—H9B0.9600
C1—C21.369 (6)C9—H9C0.9600
N3—Ni1—N3i180.000 (1)C3—C4—C5115.3 (4)
N3—Ni1—S1i94.47 (10)C6—C4—C5126.6 (3)
N3i—Ni1—S1i85.53 (10)N3—C5—C4132.7 (4)
N3—Ni1—S185.53 (10)N3—C5—H5113.7
N3i—Ni1—S194.47 (10)C4—C5—H5113.7
S1i—Ni1—S1180.00 (4)C7—C6—C4120.1 (4)
C10—S1—Ni195.26 (14)C7—C6—H6119.9
C1—O1—H1C101.2C4—C6—H6119.9
C7—O2—C8117.4 (3)O2—C7—C6124.7 (4)
C10—N1—H1A116.2O2—C7—C1114.9 (3)
C10—N1—H1B122.8C6—C7—C1120.4 (4)
H1A—N1—H1B121.0O2—C8—C9107.5 (3)
C10—N2—N3112.4 (3)O2—C8—H8A110.2
C5—N3—N2115.4 (3)C9—C8—H8A110.2
C5—N3—Ni1125.1 (3)O2—C8—H8B110.2
N2—N3—Ni1119.5 (2)C9—C8—H8B110.2
O1—C1—C2118.7 (4)H8A—C8—H8B108.5
O1—C1—C7121.6 (4)C8—C9—H9A109.5
C2—C1—C7119.6 (4)C8—C9—H9B109.5
C1—C2—C3120.0 (4)H9A—C9—H9B109.5
C1—C2—H2120.0C8—C9—H9C109.5
C3—C2—H2120.0H9A—C9—H9C109.5
C2—C3—C4121.7 (4)H9B—C9—H9C109.5
C2—C3—H3119.2N2—C10—N1117.4 (4)
C4—C3—H3119.2N2—C10—S1123.9 (3)
C3—C4—C6118.2 (4)N1—C10—S1118.7 (3)
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1ii0.872.303.124 (5)156
O1—H1C···O20.942.062.678 (5)121
O1—H1C···O3iii0.942.052.896 (4)148
Symmetry codes: (ii) x1, y+1, z; (iii) x+1, y, z.
 

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