Bis[ethyl 2-cyano-2-(oxidoimino)acetate]bis­(ethyl­ene­diamine)nickel(II) hexa­hydrate

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.

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

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Computing details

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

Crystal data

[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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 0.4591P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Ni1—N1^i	2.084 (2)	N2—C2	1.481 (3)
Ni1—N1	2.084 (2)	N2—H21N	0.9000
Ni1—N2^i	2.090 (2)	N2—H22N	0.9000
Ni1—N2	2.090 (2)	N3—C3	1.142 (3)
Ni1—N3^i	2.156 (2)	N4—C4	1.329 (4)
Ni1—N3	2.156 (2)	C1—C2^i	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—C1^i	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
N1^i—Ni1—N1	180.000 (1)	O1—N4—C4	116.6 (3)
N1^i—Ni1—N2^i	96.75 (9)	N1—C1—C2^i	109.4 (2)
N1—Ni1—N2^i	83.25 (9)	N1—C1—H1A	109.8
N1^i—Ni1—N2	83.25 (9)	C2^i—C1—H1A	109.8
N1—Ni1—N2	96.75 (9)	N1—C1—H1B	109.8
N2^i—Ni1—N2	180.0	C2^i—C1—H1B	109.8
N1^i—Ni1—N3^i	87.58 (9)	H1A—C1—H1B	108.2
N1^i—Ni1—N3	92.42 (9)	N2—C2—C1^i	108.5 (2)
N1—Ni1—N3	87.58 (9)	N2—C2—H2A	110.0
N1—Ni1—N3^i	92.42 (9)	C1^i—C2—H2A	110.0
N2^i—Ni1—N3^i	89.98 (9)	N2—C2—H2B	110.0
N2—Ni1—N3^i	90.02 (9)	C1^i—C2—H2B	110.0
N2^i—Ni1—N3	90.02 (9)	H2A—C2—H2B	108.4
N2—Ni1—N3	89.98 (9)	N3—C3—C4	179.4 (3)
N3^i—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
N2^i—Ni1—N1—C1	7.82 (16)	Ni1—N1—C1—C2^i	−33.9 (2)
N2—Ni1—N1—C1	−172.18 (16)	Ni1—N2—C2—C1^i	43.8 (2)
N3^i—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)
N1^i—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)
N3^i—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)
N1^i—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)
N2^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O1^ii	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···O1W^iii	0.87	1.97	2.823 (3)	167
O3W—H32W···O1W^iv	0.81	2.00	2.797 (3)	171
N1—H11N···O3^v	0.90	2.21	3.055 (3)	155
N1—H12N···O3^vi	0.90	2.27	3.050 (3)	145
N2—H22N···O3^v	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.