Diaqua­bis(biuretato-κ2O,O′)nickel(II) dichloride

Lawson, J.; Harrison, W.T.A.

doi:10.1107/S1600536805004393

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 3| March 2005| Pages m525-m527

https://doi.org/10.1107/S1600536805004393

Diaquabis(biuretato-κ²O,O′)nickel(II) dichloride

Jeffrey Lawson ^a and William T. A. Harrison ^a ^*

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 3 February 2005; accepted 8 February 2005; online 12 February 2005)

The title compound, [Ni(C₂H₅N₃O₂)₂(H₂O)₂]Cl₂, contains Ni²⁺ cations octahedrally coordinated by two bidentate biuret molecules in an O,O′-bidentate coordination mode and two water molecules, the latter in a trans configuration. Two chloride anions provide charge compensation. Numerous N—H⋯O (mean H⋯O = 2.17 Å, mean N—H⋯O = 164° and mean N⋯O = 2.991 Å), N—H⋯Cl (mean H⋯Cl = 2.46 Å, mean N—H⋯Cl = 162° and mean N⋯Cl = 3.278 Å) and O—H⋯Cl (mean H⋯Cl = 2.19 Å, mean O—H⋯Cl = 159° and mean O⋯Cl = 3.068 Å) hydrogen bonds help to stabilize the crystal packing.

Comment

Biuret, H₂N—CO—NH—CO—NH₂ (or C₂H₅N₃O₂), has long been recognized as a ligand in coordination chemistry (Wiedemann, 1848 ). In low-pH or neutral conditions, biuret commonly shows O,O′-bidentate coordination to metal cations [e.g. with zinc (Nardelli et al., 1963 ), copper (Freeman & Smith, 1966 ) or samarium (Haddad, 1987 )]. When biuret is deprotonated in basic conditions, N,N′-bidentate coordination can arise [e.g. with copper (Pajunen & Pajunen, 1982 )].

In the present paper, we report the synthesis and structure of a nickel(II) complex of biuret, viz. [Ni(C₂H₅N₃O₂)₂(H₂O)₂]Cl₂, (I) (Fig. 1). Compound (I) contains Ni²⁺ cations coordinated by two distinct biuret molecules, in O,O′-bidentate mode (thus forming six-membered chelate rings), and two trans water molecules. The structure is completed by two uncoordinated chloride ions, which provide charge balance and participate in an extensive hydrogen-bond network (see below). The resulting NiO₆ moiety of the [Ni(C₂H₅N₃O₂)₂(H₂O)₂]²⁺ grouping (Table 1) is close to being an undistorted octahedron [Ni—O = 2.014 (2)–2.083 (2) Å, mean Ni—O = 2.041 (3) Å; cis and trans O—Ni—O = 87.47 (9)–93.51 (8)° and 176.14 (9)–178.94 (8)°, respectively], indicating that the nickel(II) cation is a good `fit' for the biuret O,O′ bite angle. The two biuret molecules in (I) can be broken down into two H₂N—CO—NH fragments, fused via the central HN group [i.e. via atoms N2 and N5 in (I)]. For the non-H atoms, the four H₂N—CO—NH fragments are all essentially planar (for C1/O1/N1/N2, r.m.s. deviation from the least-squares plane = 0.0021 Å; for C2/O2/N2/N3, 0.0017 Å; for C3/O3/N4/N5, 0.0023 Å; for C4/O4/N5/N6, 0.0032 Å). The dihedral angle between the C1- and C2-containing fragments is 4.8 (3)°, with a corresponding value of 3.19 (3)° for the C3 and C4 fragments. This configuration can be compared with a twist angle between the fused H₂N—CO—NH fragments of 6.35° in [Cu(C₂H₅N₃O₂)₂]Cl₂ (Freeman & Smith, 1966). The dihedral angle between mean planes of the two biuret ligand molecules in (I) is 1.90 (13)°.

The Ni atom in (I) is slightly displaced from the least-squares plane of the approximate square of biuret O atoms (O1–O4) coordinating to it, by 0.0086 (13) Å. The biuret O₄ square itself is slightly folded, with deviations from the O1–O4 mean plane of −0.0121 (12), 0.0119 (12), 0.0121 (12) and −0.0119 (12) Å for atoms O1, O2, O3 and O4, respectively. In the copper analogue (Freeman & Smith, 1966), the CuO₄ square is constrained by space-group symmetry to be perfectly flat. Overall, the [Ni(C₂H₅N₃O₂)₂]²⁺ grouping in (I) is close to planar [r.m.s. deviation from the mean plane = 0.030 Å; maximum deviation = 0.076 (3) Å for N2], whereas the [Cu(C₂H₅N₃O₂)₂]²⁺ grouping in [Cu(C₂H₅N₃O₂)₂]Cl₂ is distinctly puckered (Freeman & Smith, 1966) about the O⋯O′ axes (bite lines) of the biuret molecules. As well as electrostatic and van der Waals forces, numerous hydrogen bonds (Table 2) help to define the crystal packing in (I). These include N—H⋯O bonds (mean H⋯O = 2.17 Å, mean N—H⋯O = 164° and mean N⋯O = 2.991 Å) to O acceptors from both the biuret and the water ligands, N—H⋯Cl interactions (mean H⋯Cl = 2.46 Å, mean N—H⋯Cl = 162° and mean N⋯Cl = 3.278 Å) and O—H⋯Cl interactions (mean H⋯Cl = 2.19 Å, mean O—H⋯Cl = 159° and mean O⋯Cl = 3.068 Å).

Perhaps the most interesting hydrogen bonds are N3—H4⋯O3ⁱⁱⁱ and N4—H6⋯O2^iv (see Fig. 2 and Table 2 for symmetry information), which link the [Ni(C₂H₅N₃O₂)₂(H₂O)₂]²⁺ groupings into a chain propagating along [100]. The supramolecular (Bernstein et al., 1995 ) motif is an R₂²(8) ring. The remaining H bonds serve to crosslink the [100] chains into a three-dimensional network (Fig. 3) via the chloride ions. Overall, Cl1 and Cl2 accept five hydrogen bonds each.

Figure 1
Asymmetric unit of (I)

, showing 50% probability displacement ellipsoids. H atoms are drawn as small spheres of arbitrary radii and the hydrogen bond is indicated by dashed lines.

Figure 2
Detail of (I)

, showing how the N3—H4⋯O3ⁱⁱⁱ and N4—H6⋯O2^iv hydrogen bonds (dashed lines; see Table 2

for symmetry codes) link the [Ni(C₂H₅N₃O₂)₂(H₂O)₂]²⁺ groupings into an infinite chain propagating along [100].

Figure 3
Projection on to (100) of (I)

, showing the hydrogen-bond cross-linking (dashed lines) between the chains shown in Fig. 2

Experimental

Aqueous solutions of NiCl₂ and biuret (both 0.1 M) were mixed in a 1:1 ratio at room temperature, resulting in a green solution. Small block-like green crystals of (I) grew over the course of a few days as the water slowly evaporated and were harvested by vacuum filtration and washing with acetone.

Crystal data

[Ni(C₂H₅N₃O₂)₂(H₂O)₂]Cl₂
M_r = 371.82
Monoclinic, P 2₁ /c
a = 7.3872 (4) Å
b = 27.5675 (16) Å
c = 7.6687 (4) Å
β = 117.344 (1)°
V = 1387.21 (13) Å³
Z = 4
D_x = 1.780 Mg m⁻³
Mo Kα radiation
Cell parameters from 3015 reflections
θ = 3.0–29.5°
μ = 1.82 mm⁻¹
T = 293 (2) K
Block, green
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
ω scans
Absorption correction: multi-scan(SADABS; Bruker, 1999 )T_min = 0.773, T_max = 0.839
14042 measured reflections
4037 independent reflections
2416 reflections with I > 2σ(I)
R_int = 0.053
θ_max = 30.0°
h = −10 → 8
k = −38 → 38
l = −9 → 10

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.101
S = 0.96
4037 reflections
172 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0438P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O3	2.014 (2)
Ni1—O2	2.018 (2)
Ni1—O4	2.024 (2)
Ni1—O1	2.024 (2)
Ni1—O6	2.080 (2)
Ni1—O5	2.083 (2)

O1—C1—N2—C2	−5.1 (6)
O2—C2—N2—C1	6.7 (6)
O4—C4—N5—C3	4.3 (6)
O3—C3—N5—C4	−3.3 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2ⁱ	0.86	2.49	3.340 (3)	173
N1—H2⋯O5ⁱⁱ	0.86	2.33	3.089 (4)	147
N2—H3⋯Cl2ⁱⁱ	0.86	2.45	3.266 (3)	158
N3—H4⋯O3ⁱⁱⁱ	0.86	2.10	2.943 (4)	168
N3—H5⋯Cl2ⁱⁱ	0.86	2.43	3.239 (3)	158
N4—H6⋯O2^iv	0.86	2.06	2.910 (4)	168
N4—H7⋯Cl1^v	0.86	2.45	3.252 (3)	155
N5—H8⋯Cl1^v	0.86	2.51	3.310 (3)	156
N6—H9⋯Cl1^vi	0.86	2.41	3.259 (3)	169
N6—H10⋯O6^vii	0.86	2.17	3.023 (3)	173
O5—H11⋯Cl2	0.94	2.16	3.068 (2)	161
O5—H12⋯Cl1ⁱⁱⁱ	0.91	2.21	3.115 (2)	171
O6—H13⋯Cl2^viii	0.98	2.18	3.060 (2)	149
O6—H14⋯Cl1^viii	0.88	2.20	3.027 (2)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1; (iii) x+1, y, z; (iv) x-1, y, z; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (viii) x, y, z-1.

The water H atoms were found in difference maps and were refined as riding on their carrier atoms in their as-found relative positions. The N-bound H atoms were placed in calculated positions assuming sp² hybridization for the N atoms and refined as riding on their carrier atoms. The constraint U_iso(H) = 1.2U_eq(carrier atom) was applied in all cases.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805004393/sj6047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805004393/sj6047Isup2.hkl

Computing details top

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

Diaquabis(biuretato-κ²O,O')nickel(II) dichloride top

Crystal data top

[Ni(C₂H₅N₃O₂)₂(H₂O)₂]Cl₂	F(000) = 760
M_r = 371.82	D_x = 1.780 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3015 reflections
a = 7.3872 (4) Å	θ = 3.0–29.5°
b = 27.5675 (16) Å	µ = 1.82 mm⁻¹
c = 7.6687 (4) Å	T = 293 K
β = 117.344 (1)°	Block, green
V = 1387.21 (13) Å³	0.15 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	4037 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 30.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→8
T_min = 0.773, T_max = 0.839	k = −38→38
14042 measured reflections	l = −9→10

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0438P)²] where P = (F_o² + 2F_c²)/3
4037 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.35 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	U_iso*/U_eq
Ni1	0.80268 (6)	0.125527 (13)	0.32664 (6)	0.03046 (12)
C1	0.8121 (5)	0.02016 (11)	0.2587 (5)	0.0363 (8)
C2	1.1095 (5)	0.06564 (11)	0.2773 (5)	0.0406 (8)
N1	0.7399 (4)	−0.02492 (10)	0.2330 (5)	0.0531 (9)
H1	0.6234	−0.0305	0.2287	0.064*
H2	0.8099	−0.0484	0.2208	0.064*
N2	1.0015 (4)	0.02374 (10)	0.2650 (4)	0.0419 (7)
H3	1.0587	−0.0031	0.2607	0.050*
N3	1.2783 (5)	0.05885 (11)	0.2623 (6)	0.0654 (11)
H4	1.3544	0.0832	0.2697	0.078*
H5	1.3123	0.0301	0.2451	0.078*
O1	0.7160 (3)	0.05514 (7)	0.2769 (4)	0.0407 (6)
O2	1.0539 (3)	0.10651 (8)	0.3023 (4)	0.0434 (6)
C3	0.4936 (5)	0.18368 (11)	0.3785 (5)	0.0365 (7)
C4	0.7877 (5)	0.23070 (11)	0.3984 (5)	0.0345 (7)
N4	0.3254 (5)	0.18961 (11)	0.3945 (5)	0.0589 (9)
H6	0.2503	0.1650	0.3861	0.071*
H7	0.2904	0.2181	0.4135	0.071*
N5	0.6018 (4)	0.22604 (9)	0.3972 (4)	0.0414 (7)
H8	0.5465	0.2524	0.4095	0.050*
N6	0.8615 (5)	0.27574 (9)	0.4285 (5)	0.0494 (8)
H9	0.9761	0.2816	0.4292	0.059*
H10	0.7944	0.2989	0.4473	0.059*
O3	0.5507 (3)	0.14320 (7)	0.3511 (3)	0.0367 (5)
O4	0.8813 (3)	0.19646 (7)	0.3708 (3)	0.0367 (5)
O5	0.9625 (3)	0.11171 (8)	0.6268 (3)	0.0414 (6)
H11	0.8746	0.1024	0.6790	0.050*
H12	1.0370	0.1374	0.6995	0.050*
O6	0.6618 (3)	0.14025 (7)	0.0272 (3)	0.0385 (5)
H13	0.6310	0.1096	−0.0452	0.046*
H14	0.5429	0.1508	0.0129	0.046*
Cl1	0.25969 (13)	0.19350 (3)	0.87623 (14)	0.0473 (2)
Cl2	0.70170 (15)	0.05765 (3)	0.78053 (15)	0.0485 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0271 (2)	0.02096 (17)	0.0516 (3)	−0.00128 (16)	0.02523 (18)	−0.00374 (17)
C1	0.0340 (18)	0.0300 (15)	0.046 (2)	−0.0049 (13)	0.0197 (17)	−0.0057 (13)
C2	0.0303 (17)	0.0339 (17)	0.059 (2)	−0.0039 (14)	0.0220 (17)	−0.0066 (15)
N1	0.0429 (18)	0.0282 (14)	0.101 (3)	−0.0037 (12)	0.0440 (19)	−0.0091 (15)
N2	0.0354 (16)	0.0285 (14)	0.070 (2)	0.0013 (11)	0.0310 (16)	−0.0050 (13)
N3	0.0457 (18)	0.0348 (16)	0.140 (3)	−0.0083 (14)	0.063 (2)	−0.0249 (18)
O1	0.0345 (12)	0.0243 (11)	0.0723 (16)	−0.0021 (9)	0.0322 (12)	−0.0070 (10)
O2	0.0354 (12)	0.0303 (11)	0.0780 (18)	−0.0031 (10)	0.0377 (13)	−0.0103 (11)
C3	0.0331 (18)	0.0339 (16)	0.049 (2)	−0.0029 (14)	0.0242 (16)	−0.0034 (14)
C4	0.0314 (17)	0.0336 (16)	0.0414 (19)	−0.0041 (13)	0.0191 (16)	−0.0028 (14)
N4	0.0500 (19)	0.0343 (16)	0.120 (3)	−0.0020 (14)	0.062 (2)	−0.0050 (17)
N5	0.0369 (16)	0.0295 (14)	0.069 (2)	−0.0034 (12)	0.0344 (16)	−0.0088 (13)
N6	0.0484 (18)	0.0267 (14)	0.092 (3)	−0.0073 (13)	0.0484 (19)	−0.0138 (14)
O3	0.0318 (12)	0.0256 (10)	0.0634 (16)	−0.0018 (9)	0.0309 (12)	−0.0046 (10)
O4	0.0349 (12)	0.0255 (10)	0.0611 (15)	−0.0037 (9)	0.0320 (12)	−0.0080 (10)
O5	0.0379 (13)	0.0349 (12)	0.0555 (15)	−0.0046 (10)	0.0251 (12)	−0.0016 (10)
O6	0.0378 (13)	0.0303 (11)	0.0530 (14)	0.0005 (9)	0.0257 (12)	−0.0044 (10)
Cl1	0.0364 (4)	0.0373 (4)	0.0693 (6)	0.0004 (4)	0.0253 (5)	−0.0030 (4)
Cl2	0.0576 (6)	0.0355 (4)	0.0704 (6)	−0.0030 (4)	0.0449 (5)	−0.0062 (4)

Geometric parameters (Å, º) top

Ni1—O3	2.014 (2)	N3—H5	0.8600
Ni1—O2	2.018 (2)	C3—O3	1.245 (4)
Ni1—O4	2.024 (2)	C3—N4	1.314 (4)
Ni1—O1	2.024 (2)	C3—N5	1.385 (4)
Ni1—O6	2.080 (2)	C4—O4	1.244 (4)
Ni1—O5	2.083 (2)	C4—N6	1.333 (4)
C1—O1	1.243 (4)	C4—N5	1.375 (4)
C1—N1	1.331 (4)	N4—H6	0.8600
C1—N2	1.382 (4)	N4—H7	0.8600
C2—O2	1.244 (4)	N5—H8	0.8600
C2—N3	1.317 (4)	N6—H9	0.8600
C2—N2	1.382 (4)	N6—H10	0.8600
N1—H1	0.8600	O5—H11	0.9419
N1—H2	0.8600	O5—H12	0.9121
N2—H3	0.8600	O6—H13	0.9778
N3—H4	0.8600	O6—H14	0.8833

O3—Ni1—O2	178.94 (8)	C2—N3—H5	120.0
O3—Ni1—O4	87.54 (8)	H4—N3—H5	120.0
O2—Ni1—O4	93.51 (8)	C1—O1—Ni1	128.1 (2)
O3—Ni1—O1	91.35 (9)	C2—O2—Ni1	129.2 (2)
O2—Ni1—O1	87.61 (9)	O3—C3—N4	122.4 (3)
O4—Ni1—O1	178.38 (9)	O3—C3—N5	123.3 (3)
O3—Ni1—O6	92.32 (9)	N4—C3—N5	114.3 (3)
O2—Ni1—O6	87.91 (10)	O4—C4—N6	121.4 (3)
O4—Ni1—O6	87.47 (9)	O4—C4—N5	124.0 (3)
O1—Ni1—O6	91.41 (9)	N6—C4—N5	114.6 (3)
O3—Ni1—O5	91.17 (9)	C3—N4—H6	120.0
O2—Ni1—O5	88.63 (10)	C3—N4—H7	120.0
O4—Ni1—O5	91.04 (9)	H6—N4—H7	120.0
O1—Ni1—O5	90.15 (9)	C4—N5—C3	127.3 (3)
O6—Ni1—O5	176.14 (9)	C4—N5—H8	116.3
O1—C1—N1	122.1 (3)	C3—N5—H8	116.3
O1—C1—N2	124.2 (3)	C4—N6—H9	120.0
N1—C1—N2	113.7 (3)	C4—N6—H10	120.0
O2—C2—N3	122.4 (3)	H9—N6—H10	120.0
O2—C2—N2	123.1 (3)	C3—O3—Ni1	129.2 (2)
N3—C2—N2	114.5 (3)	C4—O4—Ni1	128.5 (2)
C1—N1—H1	120.0	Ni1—O5—H11	111.6
C1—N1—H2	120.0	Ni1—O5—H12	114.2
H1—N1—H2	120.0	H11—O5—H12	107.0
C1—N2—C2	127.3 (3)	Ni1—O6—H13	109.0
C1—N2—H3	116.4	Ni1—O6—H14	99.6
C2—N2—H3	116.4	H13—O6—H14	104.8
C2—N3—H4	120.0

O1—C1—N2—C2	−5.1 (6)	O4—C4—N5—C3	4.3 (6)
N1—C1—N2—C2	175.6 (3)	N6—C4—N5—C3	−176.8 (3)
O2—C2—N2—C1	6.7 (6)	O3—C3—N5—C4	−3.3 (6)
N3—C2—N2—C1	−173.9 (3)	N4—C3—N5—C4	176.0 (3)
N1—C1—O1—Ni1	177.6 (3)	N4—C3—O3—Ni1	−178.9 (3)
N2—C1—O1—Ni1	−1.7 (5)	N5—C3—O3—Ni1	0.3 (5)
O3—Ni1—O1—C1	−175.2 (3)	O4—Ni1—O3—C3	1.1 (3)
O2—Ni1—O1—C1	4.6 (3)	O1—Ni1—O3—C3	−177.7 (3)
O6—Ni1—O1—C1	92.5 (3)	O6—Ni1—O3—C3	−86.3 (3)
O5—Ni1—O1—C1	−84.0 (3)	O5—Ni1—O3—C3	92.1 (3)
N3—C2—O2—Ni1	179.4 (3)	N6—C4—O4—Ni1	178.9 (2)
N2—C2—O2—Ni1	−1.3 (5)	N5—C4—O4—Ni1	−2.2 (5)
O4—Ni1—O2—C2	178.0 (3)	O3—Ni1—O4—C4	−0.1 (3)
O1—Ni1—O2—C2	−3.2 (3)	O2—Ni1—O4—C4	−179.9 (3)
O6—Ni1—O2—C2	−94.7 (3)	O6—Ni1—O4—C4	92.3 (3)
O5—Ni1—O2—C2	87.0 (3)	O5—Ni1—O4—C4	−91.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.86	2.49	3.340 (3)	173
N1—H2···O5ⁱⁱ	0.86	2.33	3.089 (4)	147
N2—H3···Cl2ⁱⁱ	0.86	2.45	3.266 (3)	158
N3—H4···O3ⁱⁱⁱ	0.86	2.10	2.943 (4)	168
N3—H5···Cl2ⁱⁱ	0.86	2.43	3.239 (3)	158
N4—H6···O2^iv	0.86	2.06	2.910 (4)	168
N4—H7···Cl1^v	0.86	2.45	3.252 (3)	155
N5—H8···Cl1^v	0.86	2.51	3.310 (3)	156
N6—H9···Cl1^vi	0.86	2.41	3.259 (3)	169
N6—H10···O6^vii	0.86	2.17	3.023 (3)	173
O5—H11···Cl2	0.94	2.16	3.068 (2)	161
O5—H12···Cl1ⁱⁱⁱ	0.91	2.21	3.115 (2)	171
O6—H13···Cl2^viii	0.98	2.18	3.060 (2)	149
O6—H14···Cl1^viii	0.88	2.20	3.027 (2)	155

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) x+1, y, z; (iv) x−1, y, z; (v) x, −y+1/2, z−1/2; (vi) x+1, −y+1/2, z−1/2; (vii) x, −y+1/2, z+1/2; (viii) x, y, z−1.

References

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Volume 61| Part 3| March 2005| Pages m525-m527

https://doi.org/10.1107/S1600536805004393

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