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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
CCDC reference: 634060
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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]·6H2O | Z = 1 |
Mr = 569.23 | F(000) = 302 |
Triclinic, P1 | Dx = 1.518 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.690 (1) Å | Cell parameters from 720 reflections |
b = 8.833 (2) Å | θ = 3.5–28.3° |
c = 11.044 (2) Å | µ = 0.85 mm−1 |
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 tube | 2332 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 28.3°, θmin = 3.5° |
Absorption correction: ψ scan (North et al., 1968) | h = −8→6 |
Tmin = 0.802, Tmax = 0.905 | k = −11→11 |
4325 measured reflections | l = −14→13 |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H 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 parameters | Δρmax = 0.90 e Å−3 |
4 restraints | Δρmin = −0.52 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.01384 (15) | |
O1 | 0.7460 (3) | −0.0597 (3) | 0.7701 (2) | 0.0310 (5) | |
O2 | 0.7775 (3) | −0.0312 (2) | 0.35660 (16) | 0.0159 (4) | |
O3 | 0.9195 (3) | −0.2622 (2) | 0.45551 (19) | 0.0217 (4) | |
O1W | 0.2253 (3) | 0.2936 (2) | 1.03563 (18) | 0.0238 (4) | |
H11W | 0.2221 (3) | 0.2262 (13) | 1.1002 (13) | 0.036* | |
H12W | 0.336 (2) | 0.2624 (7) | 0.9948 (8) | 0.036* | |
O2W | 0.5864 (3) | 0.2298 (3) | 0.8758 (2) | 0.0294 (5) | |
H21W | 0.6353 (10) | 0.1462 (16) | 0.8381 (8) | 0.044* | |
H22W | 0.6816 (19) | 0.2456 (4) | 0.9086 (7) | 0.044* | |
O3W | 0.8645 (3) | 0.3911 (3) | 0.9166 (2) | 0.0324 (5) | |
H31W | 0.9790 (18) | 0.3483 (7) | 0.9475 (5) | 0.049* | |
H32W | 0.8295 (6) | 0.4836 (14) | 0.9259 (3) | 0.049* | |
N1 | 0.7751 (3) | 0.4655 (2) | 0.3785 (2) | 0.0153 (4) | |
H11N | 0.8356 | 0.5461 | 0.3776 | 0.022 (8)* | |
H12N | 0.8639 | 0.3768 | 0.4032 | 0.022 (8)* | |
N2 | 0.6266 (3) | 0.5414 (3) | 0.6510 (2) | 0.0172 (5) | |
H21N | 0.6911 | 0.4501 | 0.6885 | 0.028 (9)* | |
H22N | 0.7199 | 0.6005 | 0.6266 | 0.032 (9)* | |
N3 | 0.5777 (3) | 0.2517 (3) | 0.5532 (2) | 0.0167 (5) | |
N4 | 0.8010 (4) | −0.1280 (3) | 0.6736 (2) | 0.0273 (6) | |
C1 | 0.7282 (4) | 0.4544 (3) | 0.2541 (2) | 0.0199 (5) | |
H1A | 0.8498 | 0.3940 | 0.2068 | 0.024* | |
H1B | 0.6921 | 0.5585 | 0.2121 | 0.024* | |
C2 | 0.4521 (4) | 0.6246 (3) | 0.7362 (2) | 0.0179 (5) | |
H2A | 0.4094 | 0.7338 | 0.7055 | 0.021* | |
H2B | 0.4955 | 0.6206 | 0.8167 | 0.021* | |
C3 | 0.6599 (4) | 0.1218 (3) | 0.5605 (2) | 0.0146 (5) | |
C4 | 0.7612 (4) | −0.0415 (3) | 0.5692 (2) | 0.0158 (5) | |
C5 | 0.8280 (4) | −0.1249 (3) | 0.4569 (2) | 0.0163 (5) | |
C6 | 0.8372 (4) | −0.1058 (3) | 0.2409 (2) | 0.0195 (5) | |
H6A | 0.7609 | −0.1859 | 0.2406 | 0.023* | |
H6B | 0.9847 | −0.1549 | 0.2312 | 0.023* | |
C7 | 0.7878 (4) | 0.0183 (3) | 0.1379 (3) | 0.0228 (6) | |
H7A | 0.6417 | 0.0666 | 0.1486 | 0.034* | |
H7B | 0.8244 | −0.0283 | 0.0610 | 0.034* | |
H7C | 0.8656 | 0.0961 | 0.1382 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0117 (2) | 0.0127 (3) | 0.0170 (3) | −0.00183 (17) | −0.00160 (17) | −0.00331 (17) |
O1 | 0.0289 (11) | 0.0261 (12) | 0.0373 (13) | −0.0057 (9) | −0.0032 (9) | −0.0028 (9) |
O2 | 0.0152 (9) | 0.0127 (9) | 0.0187 (9) | −0.0014 (7) | −0.0007 (7) | −0.0021 (7) |
O3 | 0.0165 (9) | 0.0151 (10) | 0.0345 (11) | −0.0026 (7) | −0.0090 (8) | −0.0015 (8) |
O1W | 0.0244 (10) | 0.0223 (10) | 0.0241 (11) | −0.0055 (8) | −0.0026 (8) | 0.0000 (8) |
O2W | 0.0271 (11) | 0.0288 (12) | 0.0336 (12) | −0.0037 (9) | −0.0086 (9) | −0.0080 (9) |
O3W | 0.0236 (11) | 0.0324 (12) | 0.0430 (14) | −0.0028 (9) | −0.0098 (10) | −0.0112 (10) |
N1 | 0.0139 (10) | 0.0111 (10) | 0.0210 (11) | −0.0025 (8) | −0.0032 (8) | −0.0016 (8) |
N2 | 0.0156 (10) | 0.0154 (11) | 0.0204 (12) | −0.0017 (8) | −0.0037 (9) | −0.0022 (8) |
N3 | 0.0145 (10) | 0.0181 (12) | 0.0184 (11) | −0.0059 (9) | −0.0011 (8) | −0.0026 (8) |
N4 | 0.0220 (12) | 0.0403 (16) | 0.0235 (13) | −0.0158 (11) | −0.0020 (10) | −0.0014 (11) |
C1 | 0.0199 (13) | 0.0224 (14) | 0.0165 (13) | −0.0053 (11) | 0.0001 (10) | −0.0011 (10) |
C2 | 0.0206 (13) | 0.0165 (13) | 0.0166 (13) | −0.0022 (10) | −0.0031 (10) | −0.0045 (10) |
C3 | 0.0124 (11) | 0.0212 (14) | 0.0120 (12) | −0.0074 (10) | −0.0011 (9) | −0.0018 (9) |
C4 | 0.0139 (12) | 0.0140 (13) | 0.0206 (13) | −0.0058 (9) | −0.0039 (10) | 0.0018 (10) |
C5 | 0.0102 (11) | 0.0154 (13) | 0.0245 (14) | −0.0049 (9) | −0.0042 (10) | 0.0007 (10) |
C6 | 0.0197 (13) | 0.0166 (13) | 0.0214 (14) | −0.0027 (10) | 0.0014 (10) | −0.0071 (10) |
C7 | 0.0257 (14) | 0.0220 (15) | 0.0207 (14) | −0.0065 (11) | 0.0008 (11) | −0.0051 (11) |
Geometric parameters (Å, º) top
Ni1—N1i | 2.084 (2) | N2—C2 | 1.481 (3) |
Ni1—N1 | 2.084 (2) | N2—H21N | 0.9000 |
Ni1—N2i | 2.090 (2) | N2—H22N | 0.9000 |
Ni1—N2 | 2.090 (2) | N3—C3 | 1.142 (3) |
Ni1—N3i | 2.156 (2) | N4—C4 | 1.329 (4) |
Ni1—N3 | 2.156 (2) | C1—C2i | 1.521 (4) |
O1—N4 | 1.250 (3) | C1—H1A | 0.9700 |
O2—C5 | 1.335 (3) | C1—H1B | 0.9700 |
O2—C6 | 1.464 (3) | C2—C1i | 1.521 (4) |
O3—C5 | 1.217 (3) | C2—H2A | 0.9700 |
O1W—H11W | 0.8732 | C2—H2B | 0.9700 |
O1W—H12W | 0.8112 | C3—C4 | 1.433 (4) |
O2W—H21W | 0.8585 | C4—C5 | 1.472 (4) |
O2W—H22W | 0.8268 | C6—C7 | 1.497 (4) |
O3W—H31W | 0.8673 | C6—H6A | 0.9700 |
O3W—H32W | 0.8072 | C6—H6B | 0.9700 |
N1—C1 | 1.475 (3) | C7—H7A | 0.9600 |
N1—H11N | 0.9000 | C7—H7B | 0.9600 |
N1—H12N | 0.9000 | C7—H7C | 0.9600 |
| | | |
N1i—Ni1—N1 | 180.000 (1) | O1—N4—C4 | 116.6 (3) |
N1i—Ni1—N2i | 96.75 (9) | N1—C1—C2i | 109.4 (2) |
N1—Ni1—N2i | 83.25 (9) | N1—C1—H1A | 109.8 |
N1i—Ni1—N2 | 83.25 (9) | C2i—C1—H1A | 109.8 |
N1—Ni1—N2 | 96.75 (9) | N1—C1—H1B | 109.8 |
N2i—Ni1—N2 | 180.0 | C2i—C1—H1B | 109.8 |
N1i—Ni1—N3i | 87.58 (9) | H1A—C1—H1B | 108.2 |
N1i—Ni1—N3 | 92.42 (9) | N2—C2—C1i | 108.5 (2) |
N1—Ni1—N3 | 87.58 (9) | N2—C2—H2A | 110.0 |
N1—Ni1—N3i | 92.42 (9) | C1i—C2—H2A | 110.0 |
N2i—Ni1—N3i | 89.98 (9) | N2—C2—H2B | 110.0 |
N2—Ni1—N3i | 90.02 (9) | C1i—C2—H2B | 110.0 |
N2i—Ni1—N3 | 90.02 (9) | H2A—C2—H2B | 108.4 |
N2—Ni1—N3 | 89.98 (9) | N3—C3—C4 | 179.4 (3) |
N3i—Ni1—N3 | 180.0 | N4—C4—C3 | 124.8 (2) |
C5—O2—C6 | 115.2 (2) | N4—C4—C5 | 115.5 (2) |
H11W—O1W—H12W | 105.5 | C3—C4—C5 | 119.8 (2) |
H21W—O2W—H22W | 107.3 | O3—C5—O2 | 124.1 (2) |
H31W—O3W—H32W | 110.8 | O3—C5—C4 | 124.1 (2) |
C1—N1—Ni1 | 109.35 (15) | O2—C5—C4 | 111.8 (2) |
C1—N1—H11N | 109.8 | O2—C6—C7 | 108.0 (2) |
Ni1—N1—H11N | 109.8 | O2—C6—H6A | 110.1 |
C1—N1—H12N | 109.8 | C7—C6—H6A | 110.1 |
Ni1—N1—H12N | 109.8 | O2—C6—H6B | 110.1 |
H11N—N1—H12N | 108.3 | C7—C6—H6B | 110.1 |
C2—N2—Ni1 | 107.10 (15) | H6A—C6—H6B | 108.4 |
C2—N2—H21N | 110.3 | C6—C7—H7A | 109.5 |
Ni1—N2—H21N | 110.3 | C6—C7—H7B | 109.5 |
C2—N2—H22N | 110.3 | H7A—C7—H7B | 109.5 |
Ni1—N2—H22N | 110.3 | C6—C7—H7C | 109.5 |
H21N—N2—H22N | 108.5 | H7A—C7—H7C | 109.5 |
C3—N3—Ni1 | 163.3 (2) | H7B—C7—H7C | 109.5 |
| | | |
N2i—Ni1—N1—C1 | 7.82 (16) | Ni1—N1—C1—C2i | −33.9 (2) |
N2—Ni1—N1—C1 | −172.18 (16) | Ni1—N2—C2—C1i | 43.8 (2) |
N3i—Ni1—N1—C1 | −81.87 (17) | O1—N4—C4—C3 | −0.4 (4) |
N3—Ni1—N1—C1 | 98.13 (17) | O1—N4—C4—C5 | 179.9 (2) |
N1i—Ni1—N2—C2 | −20.02 (16) | C6—O2—C5—O3 | 1.0 (3) |
N1—Ni1—N2—C2 | 159.98 (16) | C6—O2—C5—C4 | −179.5 (2) |
N3i—Ni1—N2—C2 | 67.54 (17) | N4—C4—C5—O3 | −2.2 (4) |
N3—Ni1—N2—C2 | −112.46 (17) | C3—C4—C5—O3 | 178.1 (2) |
N1i—Ni1—N3—C3 | 179.6 (7) | N4—C4—C5—O2 | 178.3 (2) |
N1—Ni1—N3—C3 | −0.4 (7) | C3—C4—C5—O2 | −1.4 (3) |
N2i—Ni1—N3—C3 | 82.8 (7) | C5—O2—C6—C7 | −174.7 (2) |
N2—Ni1—N3—C3 | −97.2 (7) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H11W···O1ii | 0.87 | 1.92 | 2.788 (3) | 171 |
O1W—H12W···O2W | 0.81 | 1.95 | 2.744 (3) | 167 |
O2W—H21W···O1 | 0.86 | 1.98 | 2.833 (3) | 173 |
O2W—H22W···O3W | 0.83 | 2.00 | 2.724 (3) | 146 |
O3W—H31W···O1Wiii | 0.87 | 1.97 | 2.823 (3) | 167 |
O3W—H32W···O1Wiv | 0.81 | 2.00 | 2.797 (3) | 171 |
N1—H11N···O3v | 0.90 | 2.21 | 3.055 (3) | 155 |
N1—H12N···O3vi | 0.90 | 2.27 | 3.050 (3) | 145 |
N2—H22N···O3v | 0.90 | 2.51 | 3.316 (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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