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The centrosymmetric neutral mononuclear title complex, [Ni(C5H5N2O3)2(C2H8N2)2]·6H2O, has the Ni centre in a distorted octa­hedral environment, defined by six N atoms belonging to two chelating ethyl­enediamine mol­ecules and two cyano N atoms derived from cyanoxime ligands. The O atom of the deprotonated oxime group forms hydrogen bonds with two solvent water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048331/tk2098sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048331/tk2098Isup2.hkl
Contains datablock I

CCDC reference: 634060

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.114
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C4 .. 6.38 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H21N ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: KM-4-CCD Software (Kuma, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[ethyl 2-cyano-2-(oxidoimino)acetate]bis(ethylenediamine)nickel(II) hexahydrate top
Crystal data top
[Ni(C5H5N2O3)2(C2H8N2)2]·6H2OZ = 1
Mr = 569.23F(000) = 302
Triclinic, P1Dx = 1.518 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.690 (1) ÅCell parameters from 720 reflections
b = 8.833 (2) Åθ = 3.5–28.3°
c = 11.044 (2) ŵ = 0.85 mm1
α = 83.11 (3)°T = 100 K
β = 81.19 (3)°Prism, blue
γ = 75.69 (3)°0.25 × 0.20 × 0.12 mm
V = 622.6 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2742 independent reflections
Radiation source: fine-focus sealed tube2332 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 28.3°, θmin = 3.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 86
Tmin = 0.802, Tmax = 0.905k = 1111
4325 measured reflectionsl = 1413
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.058P)2 + 0.4591P]
where P = (Fo2 + 2Fc2)/3
2742 reflections(Δ/σ)max < 0.001
171 parametersΔρmax = 0.90 e Å3
4 restraintsΔρmin = 0.52 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
Ni10.50000.50000.50000.01384 (15)
O10.7460 (3)0.0597 (3)0.7701 (2)0.0310 (5)
O20.7775 (3)0.0312 (2)0.35660 (16)0.0159 (4)
O30.9195 (3)0.2622 (2)0.45551 (19)0.0217 (4)
O1W0.2253 (3)0.2936 (2)1.03563 (18)0.0238 (4)
H11W0.2221 (3)0.2262 (13)1.1002 (13)0.036*
H12W0.336 (2)0.2624 (7)0.9948 (8)0.036*
O2W0.5864 (3)0.2298 (3)0.8758 (2)0.0294 (5)
H21W0.6353 (10)0.1462 (16)0.8381 (8)0.044*
H22W0.6816 (19)0.2456 (4)0.9086 (7)0.044*
O3W0.8645 (3)0.3911 (3)0.9166 (2)0.0324 (5)
H31W0.9790 (18)0.3483 (7)0.9475 (5)0.049*
H32W0.8295 (6)0.4836 (14)0.9259 (3)0.049*
N10.7751 (3)0.4655 (2)0.3785 (2)0.0153 (4)
H11N0.83560.54610.37760.022 (8)*
H12N0.86390.37680.40320.022 (8)*
N20.6266 (3)0.5414 (3)0.6510 (2)0.0172 (5)
H21N0.69110.45010.68850.028 (9)*
H22N0.71990.60050.62660.032 (9)*
N30.5777 (3)0.2517 (3)0.5532 (2)0.0167 (5)
N40.8010 (4)0.1280 (3)0.6736 (2)0.0273 (6)
C10.7282 (4)0.4544 (3)0.2541 (2)0.0199 (5)
H1A0.84980.39400.20680.024*
H1B0.69210.55850.21210.024*
C20.4521 (4)0.6246 (3)0.7362 (2)0.0179 (5)
H2A0.40940.73380.70550.021*
H2B0.49550.62060.81670.021*
C30.6599 (4)0.1218 (3)0.5605 (2)0.0146 (5)
C40.7612 (4)0.0415 (3)0.5692 (2)0.0158 (5)
C50.8280 (4)0.1249 (3)0.4569 (2)0.0163 (5)
C60.8372 (4)0.1058 (3)0.2409 (2)0.0195 (5)
H6A0.76090.18590.24060.023*
H6B0.98470.15490.23120.023*
C70.7878 (4)0.0183 (3)0.1379 (3)0.0228 (6)
H7A0.64170.06660.14860.034*
H7B0.82440.02830.06100.034*
H7C0.86560.09610.13820.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0117 (2)0.0127 (3)0.0170 (3)0.00183 (17)0.00160 (17)0.00331 (17)
O10.0289 (11)0.0261 (12)0.0373 (13)0.0057 (9)0.0032 (9)0.0028 (9)
O20.0152 (9)0.0127 (9)0.0187 (9)0.0014 (7)0.0007 (7)0.0021 (7)
O30.0165 (9)0.0151 (10)0.0345 (11)0.0026 (7)0.0090 (8)0.0015 (8)
O1W0.0244 (10)0.0223 (10)0.0241 (11)0.0055 (8)0.0026 (8)0.0000 (8)
O2W0.0271 (11)0.0288 (12)0.0336 (12)0.0037 (9)0.0086 (9)0.0080 (9)
O3W0.0236 (11)0.0324 (12)0.0430 (14)0.0028 (9)0.0098 (10)0.0112 (10)
N10.0139 (10)0.0111 (10)0.0210 (11)0.0025 (8)0.0032 (8)0.0016 (8)
N20.0156 (10)0.0154 (11)0.0204 (12)0.0017 (8)0.0037 (9)0.0022 (8)
N30.0145 (10)0.0181 (12)0.0184 (11)0.0059 (9)0.0011 (8)0.0026 (8)
N40.0220 (12)0.0403 (16)0.0235 (13)0.0158 (11)0.0020 (10)0.0014 (11)
C10.0199 (13)0.0224 (14)0.0165 (13)0.0053 (11)0.0001 (10)0.0011 (10)
C20.0206 (13)0.0165 (13)0.0166 (13)0.0022 (10)0.0031 (10)0.0045 (10)
C30.0124 (11)0.0212 (14)0.0120 (12)0.0074 (10)0.0011 (9)0.0018 (9)
C40.0139 (12)0.0140 (13)0.0206 (13)0.0058 (9)0.0039 (10)0.0018 (10)
C50.0102 (11)0.0154 (13)0.0245 (14)0.0049 (9)0.0042 (10)0.0007 (10)
C60.0197 (13)0.0166 (13)0.0214 (14)0.0027 (10)0.0014 (10)0.0071 (10)
C70.0257 (14)0.0220 (15)0.0207 (14)0.0065 (11)0.0008 (11)0.0051 (11)
Geometric parameters (Å, º) top
Ni1—N1i2.084 (2)N2—C21.481 (3)
Ni1—N12.084 (2)N2—H21N0.9000
Ni1—N2i2.090 (2)N2—H22N0.9000
Ni1—N22.090 (2)N3—C31.142 (3)
Ni1—N3i2.156 (2)N4—C41.329 (4)
Ni1—N32.156 (2)C1—C2i1.521 (4)
O1—N41.250 (3)C1—H1A0.9700
O2—C51.335 (3)C1—H1B0.9700
O2—C61.464 (3)C2—C1i1.521 (4)
O3—C51.217 (3)C2—H2A0.9700
O1W—H11W0.8732C2—H2B0.9700
O1W—H12W0.8112C3—C41.433 (4)
O2W—H21W0.8585C4—C51.472 (4)
O2W—H22W0.8268C6—C71.497 (4)
O3W—H31W0.8673C6—H6A0.9700
O3W—H32W0.8072C6—H6B0.9700
N1—C11.475 (3)C7—H7A0.9600
N1—H11N0.9000C7—H7B0.9600
N1—H12N0.9000C7—H7C0.9600
N1i—Ni1—N1180.000 (1)O1—N4—C4116.6 (3)
N1i—Ni1—N2i96.75 (9)N1—C1—C2i109.4 (2)
N1—Ni1—N2i83.25 (9)N1—C1—H1A109.8
N1i—Ni1—N283.25 (9)C2i—C1—H1A109.8
N1—Ni1—N296.75 (9)N1—C1—H1B109.8
N2i—Ni1—N2180.0C2i—C1—H1B109.8
N1i—Ni1—N3i87.58 (9)H1A—C1—H1B108.2
N1i—Ni1—N392.42 (9)N2—C2—C1i108.5 (2)
N1—Ni1—N387.58 (9)N2—C2—H2A110.0
N1—Ni1—N3i92.42 (9)C1i—C2—H2A110.0
N2i—Ni1—N3i89.98 (9)N2—C2—H2B110.0
N2—Ni1—N3i90.02 (9)C1i—C2—H2B110.0
N2i—Ni1—N390.02 (9)H2A—C2—H2B108.4
N2—Ni1—N389.98 (9)N3—C3—C4179.4 (3)
N3i—Ni1—N3180.0N4—C4—C3124.8 (2)
C5—O2—C6115.2 (2)N4—C4—C5115.5 (2)
H11W—O1W—H12W105.5C3—C4—C5119.8 (2)
H21W—O2W—H22W107.3O3—C5—O2124.1 (2)
H31W—O3W—H32W110.8O3—C5—C4124.1 (2)
C1—N1—Ni1109.35 (15)O2—C5—C4111.8 (2)
C1—N1—H11N109.8O2—C6—C7108.0 (2)
Ni1—N1—H11N109.8O2—C6—H6A110.1
C1—N1—H12N109.8C7—C6—H6A110.1
Ni1—N1—H12N109.8O2—C6—H6B110.1
H11N—N1—H12N108.3C7—C6—H6B110.1
C2—N2—Ni1107.10 (15)H6A—C6—H6B108.4
C2—N2—H21N110.3C6—C7—H7A109.5
Ni1—N2—H21N110.3C6—C7—H7B109.5
C2—N2—H22N110.3H7A—C7—H7B109.5
Ni1—N2—H22N110.3C6—C7—H7C109.5
H21N—N2—H22N108.5H7A—C7—H7C109.5
C3—N3—Ni1163.3 (2)H7B—C7—H7C109.5
N2i—Ni1—N1—C17.82 (16)Ni1—N1—C1—C2i33.9 (2)
N2—Ni1—N1—C1172.18 (16)Ni1—N2—C2—C1i43.8 (2)
N3i—Ni1—N1—C181.87 (17)O1—N4—C4—C30.4 (4)
N3—Ni1—N1—C198.13 (17)O1—N4—C4—C5179.9 (2)
N1i—Ni1—N2—C220.02 (16)C6—O2—C5—O31.0 (3)
N1—Ni1—N2—C2159.98 (16)C6—O2—C5—C4179.5 (2)
N3i—Ni1—N2—C267.54 (17)N4—C4—C5—O32.2 (4)
N3—Ni1—N2—C2112.46 (17)C3—C4—C5—O3178.1 (2)
N1i—Ni1—N3—C3179.6 (7)N4—C4—C5—O2178.3 (2)
N1—Ni1—N3—C30.4 (7)C3—C4—C5—O21.4 (3)
N2i—Ni1—N3—C382.8 (7)C5—O2—C6—C7174.7 (2)
N2—Ni1—N3—C397.2 (7)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O1ii0.871.922.788 (3)171
O1W—H12W···O2W0.811.952.744 (3)167
O2W—H21W···O10.861.982.833 (3)173
O2W—H22W···O3W0.832.002.724 (3)146
O3W—H31W···O1Wiii0.871.972.823 (3)167
O3W—H32W···O1Wiv0.812.002.797 (3)171
N1—H11N···O3v0.902.213.055 (3)155
N1—H12N···O3vi0.902.273.050 (3)145
N2—H22N···O3v0.902.513.316 (3)149
Symmetry codes: (ii) x+1, y, z+2; (iii) x+1, y, z; (iv) x+1, y+1, z+2; (v) x, y+1, z; (vi) x+2, y, z+1.
 

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