{μ-N,N′-Bis[1-(2-pyridyl)ethylidene]benzene-1,2-diamine}di-μ-chlorido-bis[diaquanickel(II)] dichloride ethanol disolvate

Tamboura, F.B.; Gaye, M.; Sall, A.S.; Barry, A.H.; Bah, Y.

doi:10.1107/S1600536808041299

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages m100-m101

doi:10.1107/S1600536808041299

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{μ-N,N′-Bis[1-(2-pyridyl)ethylidene]benzene-1,2-diamine}di-μ-chlorido-bis[diaquanickel(II)] dichloride ethanol disolvate

Farba Bouyagui Tamboura,^a Mohamed Gaye,^a ^* Abdou Salam Sall,^a Aliou Hamady Barry ^b and Youssouph Bah ^c

^aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, ^bDépartement de Chimie, Faculté des Sciences, Université de Nouakchott, Nouakchott, Mauritania, and ^cDépartement de Chimie, Faculté des Sciences, Université de Conakry, Conakry, Guinea
^*Correspondence e-mail: mlgayeastou@yahoo.fr

(Received 13 November 2008; accepted 6 December 2008; online 20 December 2008)

In the title compound, [Ni₂Cl₂(C₂₀H₁₈N₄)(H₂O)₄]Cl₂·2C₂H₆O, the coordination environment of each Ni²⁺ ion is distorted octahedral formed by two N atoms from the Schiff base ligand, two O atoms from water molecules and two chloride anions acting as μ₂ bridges between the metal ions. The coordinated water molecules are linked to the uncoordinated ethanol molecules and chloride anions by O—H⋯O and O—H⋯Cl hydrogen bonds, although the assignment of some of these is tentative. A weak intermolecular O—H⋯N interaction within the ligand is also observed.

Related literature

For related structures, see: Kelly et al. (2005 ); Garoufis et al. (1998 ); Li et al. (2005 ); Deters et al. (2005 ); Sengottuvelan et al. (2008 ).

Experimental

Crystal data

[Ni₂Cl₂(C₂₀H₁₈N₄)(H₂O)₄]Cl₂·2C₂H₆O
M_r = 737.80
Orthorhombic, P 2₁ 2₁ 2₁
a = 13.078 (2) Å
b = 13.575 (2) Å
c = 17.873 (4) Å
V = 3173.06 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.57 mm⁻¹
T = 173 (2) K
0.14 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
13155 measured reflections
8765 independent reflections
6892 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.096
S = 1.04
8765 reflections
385 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.63 e Å⁻³
Absolute structure: Flack (1983 ), 3623 Friedel pairs
Flack parameter: 0.005 (12)

Table 1
Selected bond lengths (Å)

Ni1—N1	2.071 (3)
Ni1—N2	2.073 (3)
Ni1—O1	2.072 (2)
Ni1—O2	2.085 (2)
Ni1—Cl2	2.3985 (8)
Ni1—Cl1	2.4323 (8)
Ni2—N4	2.063 (2)
Ni2—N3	2.077 (3)
Ni2—O3	2.087 (2)
Ni2—O4	2.097 (2)
Ni2—Cl2	2.3778 (8)
Ni2—Cl1	2.4331 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—HW1A⋯O5ⁱ	0.888 (19)	1.98 (3)	2.781 (3)	150 (4)
O1—HW1B⋯Cl3ⁱ	0.934 (18)	2.175 (19)	3.107 (2)	176 (4)
O2—HW2A⋯Cl3ⁱ	0.916 (19)	2.21 (2)	3.104 (3)	165 (4)
O2—HW2B⋯Cl4	0.942 (19)	2.122 (19)	3.064 (3)	179 (4)
O3—HW3A⋯O5ⁱ	0.939 (19)	1.87 (2)	2.787 (3)	163 (4)
O3—HW3B⋯Cl3ⁱⁱ	0.919 (18)	2.215 (19)	3.133 (2)	176 (4)
O4—HW4A⋯O6ⁱⁱ	0.922 (19)	1.79 (2)	2.702 (4)	168 (4)
O4—HW4B⋯Cl3ⁱⁱ	0.921 (19)	2.27 (2)	3.136 (3)	157 (4)
O5—H1A⋯O1ⁱⁱⁱ	0.84	1.96	2.781 (3)	166
O6—H2A⋯O4^iv	0.84	2.18	2.702 (4)	121
O6—H2A⋯N4^iv	0.84	2.66	3.467 (4)	163
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041299/hb2846sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041299/hb2846Isup2.hkl

checkCIF report

Comment top

The structure of the title compound, (I), is shown in Fig. 1. In the complex, the ligand coordinates the two metal ions via the two imine N atoms and the two pyridyl nitrogen atoms (one of each type per metal ion). Each metal ion is coordinated by two oxygen atoms from water molecules and two chloride anions (Table 1). Thus, the metal ions are in facial N₂O₂Cl₂ coordination environments and are connected by two chloride anions bridges to yield a binuclear complex. The Ni···Ni distance spanned by the two chloride ion bridges is 3.9615 (16) Å. The Ni—Cl distances in (I) are longer than distances observed in other Ni^II coordination complexes (Li et al., 2005; Deters et al., 2005; Sengottuvelan et al., 2008). Two chloride ions are present in the asymmetric unit to compensate for the doubly positive charge of the complex and hydrogen bonds (Table 2) help to establish the packing.

Related literature top

For related structures, see: Kelly et al. (2005); Garoufis et al. (1998); Li et al. (2005); Deters et al. (2005); Sengottuvelan et al. (2008).

Experimental top

To a mixture of 1 g (9.2 mmol) 1,2-diaminobenzene and 100 ml of ethanol was added dropwise a solution of 2.24 g (18.46 mmol) of 2-acetylpyridine. The resulting mixture was stirred under reflux for 60 min. A solution of 2.19 g (9.2 mmol) of NiCl₂.6H₂O was added. After cooling the solution was filtered and the solvent evaporated to dryness. The resulting yellow solid was recrystallized by diffusion of toluene in the ethanolic solution of the compound and green prisms of (I) were obtained (5.2 g; 75.00°) after one week. IR (cm^-1,KBr): 3372, 1595, 1570. Analysis calculated for C₂₄H₃₈Cl₄N₄O₆Ni₂: C 39.07, H 5.19, N 7.59 °; found: C 39.01, H 5.21, N 7.60 °.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for the nno-hydrogen atoms plotted at the 50% probability level.
	Fig. 2. The packing for (I): the broken lines stand for hydrogen bonds.

{µ-N,N'-Bis[1-(2-pyridyl)ethylidene]benzene-1,2-diamine}di- µ-chlorido-bis[diaquanickel(II)] dichloride ethanol disolvate top

Crystal data top

[Ni₂Cl₂(C₂₀H₁₈N₄)(H₂O)₄]Cl₂·2C₂H₆O	F(000) = 1528
M_r = 737.80	D_x = 1.544 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5114 reflections
a = 13.078 (2) Å	θ = 1.0–30.0°
b = 13.575 (2) Å	µ = 1.57 mm⁻¹
c = 17.873 (4) Å	T = 173 K
V = 3173.06 (10) Å³	Prism, green
Z = 4	0.14 × 0.12 × 0.10 mm

Data collection top

KappaCCD diffractometer	6892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 30.0°, θ_min = 3.2°
π and ω scans	h = −18→18
13155 measured reflections	k = −19→19
8765 independent reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0393P)² + 1.0903P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.006
8765 reflections	Δρ_max = 0.61 e Å⁻³
385 parameters	Δρ_min = −0.63 e Å⁻³
8 restraints	Absolute structure: Flack (1983), 3623 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.005 (12)

Crystal data top

[Ni₂Cl₂(C₂₀H₁₈N₄)(H₂O)₄]Cl₂·2C₂H₆O	V = 3173.06 (10) Å³
M_r = 737.80	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 13.078 (2) Å	µ = 1.57 mm⁻¹
b = 13.575 (2) Å	T = 173 K
c = 17.873 (4) Å	0.14 × 0.12 × 0.10 mm

Data collection top

KappaCCD diffractometer	6892 reflections with I > 2σ(I)
13155 measured reflections	R_int = 0.000
8765 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.61 e Å⁻³
S = 1.04	Δρ_min = −0.63 e Å⁻³
8765 reflections	Absolute structure: Flack (1983), 3623 Friedel pairs
385 parameters	Absolute structure parameter: 0.005 (12)
8 restraints

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.35695 (3)	0.50399 (3)	0.39085 (2)	0.01943 (9)
Ni2	0.61577 (3)	0.50829 (3)	0.40432 (2)	0.01891 (9)
Cl1	0.48398 (6)	0.39219 (5)	0.44251 (5)	0.02207 (16)
Cl2	0.48535 (6)	0.62991 (5)	0.39662 (5)	0.02335 (17)
Cl3	0.28973 (9)	0.25896 (7)	−0.01232 (6)	0.0461 (3)
Cl4	0.08115 (8)	0.53903 (7)	0.24677 (6)	0.0400 (2)
O1	0.30614 (18)	0.53214 (16)	0.49855 (13)	0.0255 (5)
HW1A	0.351 (3)	0.519 (3)	0.5344 (18)	0.050*
HW1B	0.279 (3)	0.5959 (17)	0.497 (2)	0.050*
O2	0.25390 (18)	0.60814 (18)	0.35001 (14)	0.0256 (6)
HW2A	0.228 (3)	0.645 (3)	0.3889 (18)	0.050*
HW2B	0.200 (2)	0.587 (3)	0.319 (2)	0.050*
O3	0.64419 (18)	0.53720 (16)	0.51712 (13)	0.0245 (5)
HW3A	0.588 (2)	0.535 (3)	0.549 (2)	0.050*
HW3B	0.660 (3)	0.6031 (15)	0.517 (2)	0.050*
O4	0.72880 (18)	0.61205 (17)	0.37763 (14)	0.0253 (5)
HW4A	0.7962 (17)	0.594 (3)	0.370 (2)	0.050*
HW4B	0.743 (3)	0.651 (3)	0.4184 (17)	0.050*
O5	0.03498 (19)	0.43711 (17)	0.09927 (15)	0.0345 (6)
H1A	0.0755	0.4509	0.0644	0.050*
O6	0.0747 (2)	0.0506 (3)	0.1231 (2)	0.0660 (10)
H2A	0.1320	0.0246	0.1155	0.050*
N1	0.2552 (2)	0.3885 (2)	0.37723 (17)	0.0229 (6)
N2	0.38534 (19)	0.46316 (17)	0.28105 (15)	0.0190 (5)
N3	0.60457 (19)	0.46709 (18)	0.29271 (15)	0.0193 (6)
N4	0.71873 (19)	0.39336 (18)	0.39947 (16)	0.0197 (5)
C1	0.1904 (3)	0.3521 (3)	0.4284 (2)	0.0299 (8)
H1	0.1873	0.3825	0.4762	0.036*
C2	0.1276 (3)	0.2716 (3)	0.4140 (2)	0.0355 (9)
H2	0.0824	0.2476	0.4514	0.043*
C3	0.1321 (3)	0.2272 (3)	0.3446 (2)	0.0348 (9)
H3	0.0899	0.1722	0.3334	0.042*
C4	0.1993 (3)	0.2642 (2)	0.2912 (2)	0.0282 (8)
H4	0.2034	0.2350	0.2430	0.034*
C5	0.2603 (2)	0.3446 (2)	0.3093 (2)	0.0227 (7)
C6	0.3333 (2)	0.3895 (2)	0.25517 (19)	0.0246 (7)
C7	0.3406 (3)	0.3484 (3)	0.1785 (2)	0.0370 (9)
H7A	0.2776	0.3631	0.1510	0.056*
H7B	0.3499	0.2768	0.1814	0.056*
H7C	0.3990	0.3779	0.1526	0.056*
C8	0.4461 (2)	0.5215 (2)	0.23195 (18)	0.0206 (7)
C9	0.3971 (3)	0.5831 (2)	0.1807 (2)	0.0271 (8)
H9	0.3250	0.5799	0.1751	0.032*
C10	0.4531 (3)	0.6488 (2)	0.1380 (2)	0.0291 (8)
H10	0.4192	0.6919	0.1043	0.035*
C11	0.5586 (3)	0.6515 (3)	0.1445 (2)	0.0296 (8)
H11	0.5972	0.6962	0.1149	0.036*
C12	0.6079 (3)	0.5888 (2)	0.1942 (2)	0.0274 (8)
H12	0.6804	0.5899	0.1981	0.033*
C13	0.5517 (2)	0.5246 (2)	0.23829 (18)	0.0205 (7)
C14	0.6560 (2)	0.3905 (2)	0.27341 (19)	0.0237 (7)
C15	0.6549 (3)	0.3448 (3)	0.1975 (2)	0.0386 (10)
H15A	0.6486	0.2731	0.2023	0.058*
H15B	0.7187	0.3607	0.1713	0.058*
H15C	0.5968	0.3705	0.1689	0.058*
C16	0.7215 (2)	0.3468 (2)	0.33302 (19)	0.0211 (7)
C17	0.7835 (3)	0.2657 (2)	0.3212 (2)	0.0266 (8)
H17	0.7858	0.2345	0.2736	0.032*
C18	0.8422 (3)	0.2308 (2)	0.3800 (2)	0.0314 (8)
H18	0.8847	0.1748	0.3734	0.038*
C19	0.8382 (3)	0.2780 (3)	0.4480 (2)	0.0324 (8)
H19	0.8780	0.2550	0.4889	0.039*
C20	0.7753 (3)	0.3597 (2)	0.4559 (2)	0.0267 (8)
H20	0.7725	0.3924	0.5028	0.032*
C21	−0.0361 (4)	0.3042 (3)	0.1739 (3)	0.0508 (12)
H21A	−0.0340	0.2328	0.1817	0.076*
H21B	−0.1056	0.3241	0.1603	0.076*
H21C	−0.0158	0.3378	0.2201	0.076*
C22	0.0361 (3)	0.3317 (3)	0.1123 (2)	0.0417 (10)
H22A	0.1062	0.3107	0.1258	0.050*
H22B	0.0163	0.2969	0.0658	0.050*
C23	0.0117 (4)	0.0366 (4)	0.0593 (3)	0.0704 (15)
H23A	−0.0561	0.0662	0.0694	0.084*
H23B	0.0015	−0.0350	0.0518	0.084*
C24	0.0527 (4)	0.0792 (4)	−0.0104 (3)	0.0676 (15)
H24A	0.0395	0.1503	−0.0111	0.101*
H24B	0.0193	0.0482	−0.0534	0.101*
H24C	0.1266	0.0675	−0.0129	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02046 (19)	0.01869 (19)	0.0192 (2)	−0.00053 (16)	0.00040 (15)	−0.00077 (17)
Ni2	0.02056 (19)	0.01757 (18)	0.0186 (2)	0.00017 (16)	−0.00013 (15)	−0.00029 (17)
Cl1	0.0228 (4)	0.0177 (3)	0.0257 (4)	−0.0007 (3)	0.0004 (3)	0.0026 (3)
Cl2	0.0246 (4)	0.0183 (3)	0.0272 (4)	0.0005 (3)	−0.0005 (4)	−0.0005 (3)
Cl3	0.0681 (7)	0.0345 (5)	0.0358 (6)	0.0194 (5)	0.0085 (5)	0.0105 (4)
Cl4	0.0453 (6)	0.0444 (5)	0.0303 (5)	−0.0074 (4)	−0.0043 (4)	−0.0064 (4)
O1	0.0302 (13)	0.0273 (12)	0.0188 (13)	0.0035 (10)	−0.0009 (10)	−0.0024 (10)
O2	0.0262 (14)	0.0255 (12)	0.0252 (15)	0.0027 (10)	−0.0005 (11)	−0.0031 (10)
O3	0.0289 (13)	0.0241 (11)	0.0206 (13)	−0.0015 (10)	0.0005 (10)	−0.0034 (9)
O4	0.0261 (12)	0.0250 (12)	0.0250 (14)	−0.0031 (10)	0.0020 (11)	0.0021 (10)
O5	0.0393 (15)	0.0381 (13)	0.0259 (14)	−0.0034 (11)	0.0030 (12)	0.0069 (11)
O6	0.0325 (16)	0.109 (3)	0.056 (2)	−0.0077 (17)	−0.0038 (16)	0.001 (2)
N1	0.0230 (15)	0.0211 (13)	0.0246 (16)	0.0015 (11)	−0.0007 (12)	0.0003 (12)
N2	0.0198 (13)	0.0165 (12)	0.0208 (14)	0.0000 (10)	0.0017 (11)	0.0008 (10)
N3	0.0207 (13)	0.0199 (13)	0.0172 (14)	−0.0013 (10)	0.0008 (11)	−0.0003 (10)
N4	0.0204 (13)	0.0178 (12)	0.0209 (15)	0.0001 (10)	0.0009 (12)	0.0026 (11)
C1	0.0251 (18)	0.0332 (18)	0.032 (2)	−0.0022 (15)	0.0035 (16)	0.0010 (16)
C2	0.026 (2)	0.0381 (19)	0.042 (2)	−0.0064 (16)	0.0056 (17)	0.0087 (17)
C3	0.031 (2)	0.0239 (17)	0.049 (3)	−0.0091 (16)	−0.0048 (19)	0.0004 (16)
C4	0.0275 (18)	0.0246 (17)	0.032 (2)	−0.0016 (15)	−0.0048 (16)	−0.0004 (15)
C5	0.0212 (17)	0.0207 (16)	0.0264 (19)	0.0012 (13)	0.0000 (14)	0.0026 (14)
C6	0.0275 (18)	0.0236 (16)	0.0226 (18)	0.0038 (14)	−0.0018 (14)	−0.0021 (14)
C7	0.047 (2)	0.037 (2)	0.027 (2)	−0.0130 (18)	0.0027 (18)	−0.0100 (16)
C8	0.0257 (16)	0.0181 (15)	0.0180 (16)	−0.0008 (12)	0.0016 (13)	0.0004 (12)
C9	0.0247 (18)	0.0272 (17)	0.029 (2)	0.0040 (14)	−0.0031 (15)	0.0005 (14)
C10	0.038 (2)	0.0267 (17)	0.0228 (19)	0.0036 (15)	−0.0013 (16)	0.0075 (14)
C11	0.038 (2)	0.0268 (17)	0.024 (2)	−0.0041 (15)	0.0027 (16)	0.0071 (14)
C12	0.0257 (18)	0.0294 (17)	0.0270 (19)	−0.0030 (14)	0.0017 (15)	0.0016 (14)
C13	0.0257 (16)	0.0183 (15)	0.0176 (16)	−0.0007 (12)	0.0001 (13)	−0.0016 (12)
C14	0.0236 (17)	0.0240 (16)	0.0235 (18)	−0.0021 (14)	0.0036 (14)	−0.0023 (13)
C15	0.046 (2)	0.044 (2)	0.025 (2)	0.0153 (19)	−0.0069 (18)	−0.0112 (17)
C16	0.0203 (16)	0.0211 (15)	0.0220 (18)	−0.0013 (13)	0.0003 (14)	0.0006 (13)
C17	0.0283 (19)	0.0249 (17)	0.026 (2)	0.0004 (14)	0.0017 (15)	−0.0005 (14)
C18	0.0305 (19)	0.0247 (16)	0.039 (2)	0.0076 (14)	0.0005 (17)	0.0000 (16)
C19	0.0262 (19)	0.0327 (19)	0.038 (2)	0.0077 (15)	−0.0058 (17)	0.0054 (16)
C20	0.0284 (18)	0.0288 (17)	0.0230 (19)	0.0004 (14)	−0.0031 (15)	0.0018 (14)
C21	0.053 (3)	0.049 (2)	0.050 (3)	−0.010 (2)	−0.002 (2)	0.015 (2)
C22	0.044 (2)	0.038 (2)	0.044 (3)	0.0019 (17)	0.000 (2)	0.0052 (18)
C23	0.042 (3)	0.099 (4)	0.070 (4)	−0.009 (3)	−0.003 (3)	−0.013 (3)
C24	0.065 (3)	0.096 (4)	0.042 (3)	−0.011 (3)	0.007 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Ni1—N1	2.071 (3)	C5—C6	1.490 (5)
Ni1—N2	2.073 (3)	C6—C7	1.482 (5)
Ni1—O1	2.072 (2)	C7—H7A	0.9800
Ni1—O2	2.085 (2)	C7—H7B	0.9800
Ni1—Cl2	2.3985 (8)	C7—H7C	0.9800
Ni1—Cl1	2.4323 (8)	C8—C13	1.386 (4)
Ni2—N4	2.063 (2)	C8—C9	1.396 (4)
Ni2—N3	2.077 (3)	C9—C10	1.384 (5)
Ni2—O3	2.087 (2)	C9—H9	0.9500
Ni2—O4	2.097 (2)	C10—C11	1.385 (5)
Ni2—Cl2	2.3778 (8)	C10—H10	0.9500
Ni2—Cl1	2.4331 (8)	C11—C12	1.390 (5)
O1—HW1A	0.888 (19)	C11—H11	0.9500
O1—HW1B	0.934 (18)	C12—C13	1.386 (4)
O2—HW2A	0.916 (19)	C12—H12	0.9500
O2—HW2B	0.942 (19)	C14—C16	1.490 (5)
O3—HW3A	0.939 (19)	C14—C15	1.493 (5)
O3—HW3B	0.919 (18)	C15—H15A	0.9800
O4—HW4A	0.922 (19)	C15—H15B	0.9800
O4—HW4B	0.921 (19)	C15—H15C	0.9800
O5—C22	1.450 (4)	C16—C17	1.384 (5)
O5—H1A	0.8400	C17—C18	1.385 (5)
O6—C23	1.418 (6)	C17—H17	0.9500
O6—H2A	0.8400	C18—C19	1.374 (5)
N1—C1	1.340 (4)	C18—H18	0.9500
N1—C5	1.354 (5)	C19—C20	1.389 (5)
N2—C6	1.295 (4)	C19—H19	0.9500
N2—C8	1.424 (4)	C20—H20	0.9500
N3—C14	1.285 (4)	C21—C22	1.498 (6)
N3—C13	1.426 (4)	C21—H21A	0.9800
N4—C20	1.332 (4)	C21—H21B	0.9800
N4—C16	1.346 (4)	C21—H21C	0.9800
C1—C2	1.391 (5)	C22—H22A	0.9900
C1—H1	0.9500	C22—H22B	0.9900
C2—C3	1.381 (6)	C23—C24	1.475 (7)
C2—H2	0.9500	C23—H23A	0.9900
C3—C4	1.390 (5)	C23—H23B	0.9900
C3—H3	0.9500	C24—H24A	0.9800
C4—C5	1.390 (5)	C24—H24B	0.9800
C4—H4	0.9500	C24—H24C	0.9800

N1—Ni1—O1	92.45 (11)	N2—C6—C5	114.9 (3)
N1—Ni1—N2	78.55 (11)	C7—C6—C5	119.2 (3)
O1—Ni1—N2	170.54 (10)	C6—C7—H7A	109.5
N1—Ni1—O2	93.27 (10)	C6—C7—H7B	109.5
O1—Ni1—O2	89.59 (9)	H7A—C7—H7B	109.5
N2—Ni1—O2	88.03 (10)	C6—C7—H7C	109.5
N1—Ni1—Cl2	174.04 (8)	H7A—C7—H7C	109.5
O1—Ni1—Cl2	93.04 (7)	H7B—C7—H7C	109.5
N2—Ni1—Cl2	96.08 (7)	C13—C8—C9	119.5 (3)
O2—Ni1—Cl2	89.10 (7)	C13—C8—N2	121.5 (3)
N1—Ni1—Cl1	90.64 (8)	C9—C8—N2	118.8 (3)
O1—Ni1—Cl1	88.94 (7)	C10—C9—C8	120.4 (3)
N2—Ni1—Cl1	94.02 (7)	C10—C9—H9	119.8
O2—Ni1—Cl1	175.89 (7)	C8—C9—H9	119.8
Cl2—Ni1—Cl1	87.14 (3)	C9—C10—C11	119.8 (3)
N4—Ni2—N3	78.58 (11)	C9—C10—H10	120.1
N4—Ni2—O3	93.82 (10)	C11—C10—H10	120.1
N3—Ni2—O3	172.26 (10)	C10—C11—C12	120.0 (3)
N4—Ni2—O4	92.20 (9)	C10—C11—H11	120.0
N3—Ni2—O4	90.69 (10)	C12—C11—H11	120.0
O3—Ni2—O4	88.16 (9)	C13—C12—C11	120.2 (3)
N4—Ni2—Cl2	172.31 (8)	C13—C12—H12	119.9
N3—Ni2—Cl2	94.64 (7)	C11—C12—H12	119.9
O3—Ni2—Cl2	93.04 (7)	C12—C13—C8	120.1 (3)
O4—Ni2—Cl2	91.50 (7)	C12—C13—N3	118.3 (3)
N4—Ni2—Cl1	89.10 (7)	C8—C13—N3	121.5 (3)
N3—Ni2—Cl1	92.58 (7)	N3—C14—C16	115.5 (3)
O3—Ni2—Cl1	88.68 (7)	N3—C14—C15	125.1 (3)
O4—Ni2—Cl1	176.66 (8)	C16—C14—C15	119.3 (3)
Cl2—Ni2—Cl1	87.59 (3)	C14—C15—H15A	109.5
Ni1—Cl1—Ni2	88.46 (3)	C14—C15—H15B	109.5
Ni2—Cl2—Ni1	90.56 (3)	H15A—C15—H15B	109.5
Ni1—O1—HW1A	115 (3)	C14—C15—H15C	109.5
Ni1—O1—HW1B	106 (3)	H15A—C15—H15C	109.5
HW1A—O1—HW1B	116 (4)	H15B—C15—H15C	109.5
Ni1—O2—HW2A	110 (3)	N4—C16—C17	121.6 (3)
Ni1—O2—HW2B	119 (2)	N4—C16—C14	115.4 (3)
HW2A—O2—HW2B	110 (4)	C17—C16—C14	123.0 (3)
Ni2—O3—HW3A	117 (3)	C16—C17—C18	118.7 (3)
Ni2—O3—HW3B	102 (3)	C16—C17—H17	120.7
HW3A—O3—HW3B	103 (3)	C18—C17—H17	120.7
Ni2—O4—HW4A	122 (3)	C19—C18—C17	119.5 (3)
Ni2—O4—HW4B	110 (3)	C19—C18—H18	120.3
HW4A—O4—HW4B	94 (3)	C17—C18—H18	120.3
C22—O5—H1A	109.5	C18—C19—C20	119.0 (3)
C23—O6—H2A	109.5	C18—C19—H19	120.5
C1—N1—C5	118.8 (3)	C20—C19—H19	120.5
C1—N1—Ni1	127.2 (2)	N4—C20—C19	121.7 (3)
C5—N1—Ni1	114.0 (2)	N4—C20—H20	119.1
C6—N2—C8	120.2 (3)	C19—C20—H20	119.1
C6—N2—Ni1	116.8 (2)	C22—C21—H21A	109.5
C8—N2—Ni1	122.33 (19)	C22—C21—H21B	109.5
C14—N3—C13	120.9 (3)	H21A—C21—H21B	109.5
C14—N3—Ni2	116.0 (2)	C22—C21—H21C	109.5
C13—N3—Ni2	122.83 (19)	H21A—C21—H21C	109.5
C20—N4—C16	119.5 (3)	H21B—C21—H21C	109.5
C20—N4—Ni2	126.2 (2)	O5—C22—C21	111.0 (3)
C16—N4—Ni2	114.2 (2)	O5—C22—H22A	109.4
N1—C1—C2	122.5 (3)	C21—C22—H22A	109.4
N1—C1—H1	118.8	O5—C22—H22B	109.4
C2—C1—H1	118.8	C21—C22—H22B	109.4
C3—C2—C1	118.9 (3)	H22A—C22—H22B	108.0
C3—C2—H2	120.6	O6—C23—C24	114.5 (4)
C1—C2—H2	120.6	O6—C23—H23A	108.6
C2—C3—C4	119.1 (3)	C24—C23—H23A	108.6
C2—C3—H3	120.5	O6—C23—H23B	108.6
C4—C3—H3	120.5	C24—C23—H23B	108.6
C5—C4—C3	119.1 (3)	H23A—C23—H23B	107.6
C5—C4—H4	120.5	C23—C24—H24A	109.5
C3—C4—H4	120.5	C23—C24—H24B	109.5
N1—C5—C4	121.7 (3)	H24A—C24—H24B	109.5
N1—C5—C6	115.8 (3)	C23—C24—H24C	109.5
C4—C5—C6	122.5 (3)	H24A—C24—H24C	109.5
N2—C6—C7	126.0 (3)	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—HW1A···O5ⁱ	0.89 (2)	1.98 (3)	2.781 (3)	150 (4)
O1—HW1B···Cl3ⁱ	0.93 (2)	2.18 (2)	3.107 (2)	176 (4)
O2—HW2A···Cl3ⁱ	0.92 (2)	2.21 (2)	3.104 (3)	165 (4)
O2—HW2B···Cl4	0.94 (2)	2.12 (2)	3.064 (3)	179 (4)
O3—HW3A···O5ⁱ	0.94 (2)	1.87 (2)	2.787 (3)	163 (4)
O3—HW3B···Cl3ⁱⁱ	0.92 (2)	2.22 (2)	3.133 (2)	176 (4)
O4—HW4A···O6ⁱⁱ	0.92 (2)	1.79 (2)	2.702 (4)	168 (4)
O4—HW4B···Cl3ⁱⁱ	0.92 (2)	2.27 (2)	3.136 (3)	157 (4)
O5—H1A···O1ⁱⁱⁱ	0.84	1.96	2.781 (3)	166
O6—H2A···O4^iv	0.84	2.18	2.702 (4)	121
O6—H2A···N4^iv	0.84	2.66	3.467 (4)	163

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

Experimental details

Crystal data
Chemical formula	[Ni₂Cl₂(C₂₀H₁₈N₄)(H₂O)₄]Cl₂·2C₂H₆O
M_r	737.80
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	13.078 (2), 13.575 (2), 17.873 (4)
V (Å³)	3173.06 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13155, 8765, 6892
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.096, 1.04
No. of reflections	8765
No. of parameters	385
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.63
Absolute structure	Flack (1983), 3623 Friedel pairs
Absolute structure parameter	0.005 (12)

Computer programs: COLLECT (Nonius, 1998), DENZO (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Selected bond lengths (Å) top

Ni1—N1	2.071 (3)	Ni2—N4	2.063 (2)
Ni1—N2	2.073 (3)	Ni2—N3	2.077 (3)
Ni1—O1	2.072 (2)	Ni2—O3	2.087 (2)
Ni1—O2	2.085 (2)	Ni2—O4	2.097 (2)
Ni1—Cl2	2.3985 (8)	Ni2—Cl2	2.3778 (8)
Ni1—Cl1	2.4323 (8)	Ni2—Cl1	2.4331 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—HW1A···O5ⁱ	0.888 (19)	1.98 (3)	2.781 (3)	150 (4)
O1—HW1B···Cl3ⁱ	0.934 (18)	2.175 (19)	3.107 (2)	176 (4)
O2—HW2A···Cl3ⁱ	0.916 (19)	2.21 (2)	3.104 (3)	165 (4)
O2—HW2B···Cl4	0.942 (19)	2.122 (19)	3.064 (3)	179 (4)
O3—HW3A···O5ⁱ	0.939 (19)	1.87 (2)	2.787 (3)	163 (4)
O3—HW3B···Cl3ⁱⁱ	0.919 (18)	2.215 (19)	3.133 (2)	176 (4)
O4—HW4A···O6ⁱⁱ	0.922 (19)	1.79 (2)	2.702 (4)	168 (4)
O4—HW4B···Cl3ⁱⁱ	0.921 (19)	2.27 (2)	3.136 (3)	157 (4)
O5—H1A···O1ⁱⁱⁱ	0.84	1.96	2.781 (3)	166
O6—H2A···O4^iv	0.84	2.18	2.702 (4)	121
O6—H2A···N4^iv	0.84	2.66	3.467 (4)	163

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

Acknowledgements

The authors thank the Agence Universitaire de la Francophonie for financial support (AUF-PSCI No. 6314PS804).

References

Deters, E. A., Goldcamp, M. J., Krause Bauer, J. A. & Baldwin, M. J. (2005). Inorg. Chem. 44, 5222–5228. Web of Science CSD CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Garoufis, A., Kasselouri, S., Raptopoulou, C. P. & Terzis, A. (1998). Polyhedron, 17, 1–7. Google Scholar
Kelly, T. L., Milway, V. A., Grove, H., Niel, V., Abedin, T. S. M., Thompson, L. K., Zhao, L., Harvey, R. G., Miller, D. O., Leech, M., Goeta, A. E. & Howard, J. A. K. (2005). Polyhedron, 24, 807–821. Web of Science CSD CrossRef CAS Google Scholar
Li, Q. X., Luo, Q. H., Li, Y. Z., Duan, C. Y. & Tu, O. Y. (2005). Inorg. Chim. Acta, 358, 504–512. Web of Science CSD CrossRef CAS Google Scholar
Nonius (1998). COLLECT and DENZO. Nonius BV, Delft, The Netherlands. Google Scholar
Sengottuvelan, N., Kang, S. K. & Kim, Y.-I. (2008). Bull. Korean Chem. Soc. 29, 1784–1786. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Pages m100-m101

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{μ-N,N′-Bis[1-(2-pyridyl)ethyl­idene]benzene-1,2-di­amine}di-μ-chlorido-bis­[di­aquanickel(II)] dichloride ethanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{μ-N,N′-Bis[1-(2-pyridyl)ethylidene]benzene-1,2-diamine}di-μ-chlorido-bis[diaquanickel(II)] dichloride ethanol disolvate