{4,4′-Di-tert-butyl-6,6′-bis­(di­methoxy­methyl)-2,2′-[propane-1,3-diyl­bis­(nitrilo­methyl­idyne)]­bis­(thio­phenolato)-κ4S,N,N′,S′}nickel(II)

Bjernemose, J.K.; McKenzie, C.J.; Raithby, P.R.; Teat, S.J.

doi:10.1107/S1600536804028879

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 60| Part 12| December 2004| Pages m1841-m1843

https://doi.org/10.1107/S1600536804028879

{4,4′-Di-tert-butyl-6,6′-bis(dimethoxymethyl)-2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]bis(thiophenolato)-κ⁴S,N,N′,S′}nickel(II)

Jens K. Bjernemose,^a Christine J. McKenzie,^a ^* Paul R. Raithby ^b and Simon J. Teat ^c

^aDepartment of Chemistry, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark, ^bDepartment of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, England, and ^cCLRC Daresbury Laboratory, Daresbury, Warrington WA4 4AD, England
^*Correspondence e-mail: chk@chem.sdu.dk

(Received 11 October 2004; accepted 8 November 2004; online 20 November 2004)

The title compound, [Ni(C₃₁H₄₄N₂O₄S₂)], is an N₂S₂ four-coordinated nickel(II) complex. The coordination geometry of the metal, on a twofold rotation axis, is more distorted from square planar than in related compounds.

Comment

The title compound, Ni(pabtp), (I), was isolated from a mixture of the dialdehyde [N,N′-propane-1,3-diyl(6-formyl-4-tert-butyl-2-methyliminatothiophenolato)]nickel(II) (Christensen & McKenzie, 2004 ), Ni(pfbtp) and 1,3-diaminopropane in methanol (see scheme). This reaction was an unsuccessful attempt to prepare a ring-closed Schiff base derivative of Ni(pfbtp) under conditions analogous to those in which we prepared 2 + 2 and 4 + 4 thiophenolate macrocyclic complexes using Ni(pfmtp), (II), which is homologous to Ni(pfbtp) [Cambridge Structural Database, Version 5.25 of November 2003 with three updates (Allen, 2002 ) refcode NULPOZ; Christensen et al., 1997 ].

Comparing (I) and (II), it is immediately evident that no change in the length of the coordinating bonds has occurred, but although the coordination geometry at the Ni atom in (I) may be described as square planar, it is far more distorted towards tetrahedral than in (II). This can be seen from the change in bond angles around the Ni atom, which lies on a twofold rotation axis, but is more strikingly described by looking at the volume of the (irregular) tetrahedron spanned by the four donor atoms (N₂S₂). This is 1.544 Å³ for (I) but only 0.159 Å³ for (II). A space-filling model shows no direct interaction between the two (MeO)₂CH— groups on either side of the Ni atom, thus this distortion from square planar is apparently not due to the bulkier dimethylacetal groups replacing the formyl groups. The distortion is then more likely to be due to packing effects. Inspection of the packing diagrams for (I) and (II) reveals a number of similarities. The molecules in (I) essentially stack along c, alternating their direction in either layer, but, whereas molecules in (II) have the Ni atoms directly above one another, they are more displaced in (I). These stacks then pack in a head-to-tail fashion along b, with the central methylene group nestled between the two S atoms of the next molecule [C—H⋯S = 3.64 Å compared to 3.20 Å in (II)]. These ab layers then have tert-butyl groups on both sides along c in (I) [methyl groups in the case of (II)]. This is probably the origin of the distortion around Ni, for while (II) shows only very modest interaction between the methyl and formyl groups, (I) has a much closer approach of the tert-butyl groups to the dimethoxymethyl group.

Figure 1
View of (I

), with 50% probability displacement ellipsoids shown only for atoms of the asymmetric unit. Unlabelled atoms are related to labelled atoms by -x, y, 1/2-z.

Figure 2
The packing of (a) Ni(pabtp), (I

), (b) Ni(pfmtp), (II

). View down b with tert-butyl (a) or methyl (b) groups shown as space-filling on the left and dimethoxymethyl (a) or formyl (b) groups on the right.

Experimental

Crystals of (I) were isolated from a 1:1 mixture of Ni(pfbtp) (Christensen & McKenzie, 2004) and 1,3-diaminopropane in methanol after several days standing in a closed vessel.

Crystal data

[Ni(C₃₁H₄₄N₂O₄S₂)]
M_r = 631.51
Monoclinic, C2/c
a = 28.352 (4) Å
b = 9.1532 (11) Å
c = 12.1556 (15) Å
β = 102.178 (2)°
V = 3083.5 (7) Å³
Z = 4
D_x = 1.36 Mg m⁻³
Synchrotron radiation
λ = 0.6881 Å
Cell parameters from 6249 reflections
θ = 2.8–29.2°
μ = 0.80 mm⁻¹
T = 150 (2) K
Needle, orange-red
0.22 × 0.02 × 0.01 mm

Data collection

Bruker SMART 1K CCD diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.843, T_max = 0.992
9981 measured reflections
9981 independent reflections
8220 reflections with I > 2σ(I)
θ_max = 27.5°
h = −37 → 38
k = −12 → 12
l = −16 → 16

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.228
S = 1.04
9981 reflections
188 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.169P)² + 0.2945P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 1.77 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—N1	1.907 (2)
Ni1—S1	2.1742 (8)

N1—Ni1—N1ⁱ	90.49 (14)
N1—Ni1—S1ⁱ	163.52 (7)
N1—Ni1—S1	95.30 (7)
S1ⁱ—Ni1—S1	83.41 (4)
Symmetry code: (i) $[-x,y,{\script{1\over 2}}-z]$ .

The crystals turned out to be twinned. ROTAX (Parsons & Gould, 2001 ) identifies the twinning as 180° rotation about the a axis. The twin scale is [101, 0 $[\overline 1]$ 0, 00 $[\overline 1]$ ]. The batch scale factor refines to 0.2786 (18). The non-merohedral twinning prevents merging of equivalent reflections before refinement. The maximum and minimum electron-density peaks are located 0.88 and 0.76 Å, respectively, from atom Ni1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: X-Seed (Barbour, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804028879/wk6035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804028879/wk6035Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

{4,4'-Di-tert-butyl-6,6'-bis(dimethoxymethyl)-2,2'-[propane-1,3- diylbis(nitrilomethylidyne)]bis(thiophenolato)-κ⁴S,N,N',S'}nickel(II) top

Crystal data top

[Ni(C₃₁H₄₄N₂O₄S₂)]	F(000) = 1344
M_r = 631.51	D_x = 1.36 Mg m⁻³
Monoclinic, C2/c	Synchrotron radiation, λ = 0.6881 Å
Hall symbol: -C 2yc	Cell parameters from 6249 reflections
a = 28.352 (4) Å	θ = 2.8–29.2°
b = 9.1532 (11) Å	µ = 0.80 mm⁻¹
c = 12.1556 (15) Å	T = 150 K
β = 102.178 (2)°	Needle, orange-red
V = 3083.5 (7) Å³	0.22 × 0.02 × 0.01 mm
Z = 4

Data collection top

Bruker SMART 1K CCD diffractometer	9981 independent reflections
Radiation source: Synchrotron, SRS station 9.8	8220 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0
0.20 ° ω rotation, 3 s a frame scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −37→38
T_min = 0.843, T_max = 0.992	k = −12→12
9981 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.228	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.169P)² + 0.2945P] where P = (F_o² + 2F_c²)/3
9981 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 1.77 e Å⁻³
0 restraints	Δρ_min = −1.23 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.

The crystals turn out to be twinned. ROTAX (Parsons & Gould, 2001) identifies the twinning as 180° rotation about {1 0 0} (a¯). The corresponding twin law is [1 0 1] [0 - 1 0] [0 0 - 1] The batch scale factor refines to 0.27859

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.07866 (9)	0.1434 (3)	0.1114 (2)	0.0182 (5)
C2	0.11604 (9)	0.2375 (3)	0.0921 (3)	0.0201 (5)
C3	0.15119 (10)	0.1872 (3)	0.0375 (2)	0.0208 (5)
H3	0.1764	0.2519	0.0289	0.025*
C4	0.15123 (10)	0.0449 (3)	−0.0057 (3)	0.0195 (5)
C5	0.11417 (10)	−0.0464 (3)	0.0113 (3)	0.0200 (5)
H5	0.1125	−0.1428	−0.0182	0.024*
C6	0.07905 (10)	−0.0017 (3)	0.0706 (3)	0.0190 (6)
C7	0.04429 (9)	−0.1128 (3)	0.0840 (2)	0.0208 (6)
H7	0.0434	−0.1973	0.0382	0.025*
C8	−0.01691 (10)	−0.2415 (3)	0.1459 (3)	0.0229 (6)
H8A	−0.0158	−0.2989	0.0774	0.028*
H8B	−0.0507	−0.2103	0.1418	0.028*
C9	0	−0.3360 (4)	0.25	0.0267 (8)
H9A	−0.0268	−0.3996	0.2614	0.032*	0.5
H9B	0.0268	−0.3996	0.2386	0.032*	0.5
C10	0.19091 (11)	−0.0047 (3)	−0.0660 (3)	0.0212 (6)
C11	0.23991 (11)	0.0099 (3)	0.0154 (3)	0.0309 (7)
H11A	0.2448	0.1116	0.0404	0.046*
H11B	0.2656	−0.0191	−0.0229	0.046*
H11C	0.2407	−0.0535	0.0807	0.046*
C12	0.19012 (12)	0.0918 (4)	−0.1696 (3)	0.0329 (7)
H12A	0.1592	0.0799	−0.2228	0.049*
H12B	0.2164	0.0628	−0.2059	0.049*
H12C	0.1943	0.1942	−0.1463	0.049*
C13	0.18436 (12)	−0.1650 (3)	−0.1058 (3)	0.0321 (7)
H13A	0.1883	−0.2296	−0.0402	0.048*
H13B	0.2086	−0.1892	−0.1496	0.048*
H13C	0.152	−0.1779	−0.1528	0.048*
C14	0.11796 (9)	0.3942 (3)	0.1360 (3)	0.0235 (6)
H14	0.1095	0.3925	0.2118	0.028*
C15	0.17227 (12)	0.5804 (3)	0.2073 (3)	0.0339 (8)
H15A	0.1503	0.6532	0.1651	0.051*
H15B	0.2057	0.6133	0.2146	0.051*
H15C	0.1652	0.5682	0.2824	0.051*
C16	0.09516 (15)	0.5158 (3)	−0.0422 (4)	0.0361 (8)
H16A	0.1253	0.5713	−0.033	0.054*
H16B	0.0688	0.5723	−0.088	0.054*
H16C	0.0986	0.4228	−0.0796	0.054*
N1	0.01452 (8)	−0.1109 (2)	0.1508 (2)	0.0204 (5)
O1	0.16587 (7)	0.4450 (2)	0.1494 (2)	0.0290 (5)
O2	0.08471 (8)	0.4884 (2)	0.0652 (2)	0.0311 (6)
Ni1	0	0.03581 (5)	0.25	0.01859 (15)
S1	0.03409 (3)	0.21315 (7)	0.17667 (7)	0.02433 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0216 (12)	0.0109 (12)	0.0249 (14)	−0.0007 (9)	0.0108 (11)	−0.0012 (10)
C2	0.0242 (12)	0.0106 (12)	0.0270 (14)	−0.0027 (9)	0.0091 (11)	−0.0017 (10)
C3	0.0242 (13)	0.0124 (12)	0.0284 (15)	−0.0023 (9)	0.0112 (11)	0.0006 (10)
C4	0.0212 (12)	0.0131 (12)	0.0256 (15)	−0.0007 (9)	0.0079 (11)	0.0003 (10)
C5	0.0242 (13)	0.0100 (12)	0.0277 (15)	−0.0013 (9)	0.0097 (11)	−0.0009 (10)
C6	0.0190 (12)	0.0095 (12)	0.0304 (16)	−0.0023 (9)	0.0092 (11)	−0.0011 (10)
C7	0.0243 (12)	0.0131 (12)	0.0254 (15)	−0.0036 (10)	0.0059 (11)	−0.0036 (10)
C8	0.0266 (13)	0.0161 (13)	0.0278 (16)	−0.0069 (10)	0.0095 (12)	−0.0022 (11)
C9	0.038 (2)	0.0121 (18)	0.034 (2)	0	0.016 (2)	0
C10	0.0259 (13)	0.0098 (12)	0.0321 (17)	0.0013 (9)	0.0154 (13)	0.0008 (10)
C11	0.0229 (14)	0.0263 (16)	0.045 (2)	0.0031 (11)	0.0095 (15)	−0.0008 (13)
C12	0.0465 (17)	0.0230 (15)	0.0354 (19)	0.0070 (13)	0.0227 (15)	0.0074 (13)
C13	0.0380 (16)	0.0121 (14)	0.053 (2)	0.0002 (11)	0.0242 (15)	−0.0052 (12)
C14	0.0273 (13)	0.0126 (13)	0.0337 (17)	−0.0037 (10)	0.0131 (12)	−0.0053 (11)
C15	0.0441 (18)	0.0184 (15)	0.042 (2)	−0.0098 (12)	0.0160 (15)	−0.0142 (13)
C16	0.052 (2)	0.0176 (15)	0.036 (2)	−0.0112 (13)	0.0022 (17)	0.0011 (13)
N1	0.0237 (11)	0.0108 (10)	0.0268 (13)	−0.0035 (8)	0.0053 (9)	−0.0007 (9)
O1	0.0297 (11)	0.0162 (10)	0.0444 (14)	−0.0080 (8)	0.0153 (10)	−0.0127 (9)
O2	0.0354 (12)	0.0130 (10)	0.0465 (17)	0.0013 (8)	0.0121 (11)	−0.0008 (9)
Ni1	0.0206 (2)	0.0115 (2)	0.0264 (3)	0	0.0112 (2)	0
S1	0.0298 (3)	0.0120 (3)	0.0370 (4)	−0.0027 (2)	0.0204 (3)	−0.0034 (3)

Geometric parameters (Å, º) top

C1—C6	1.418 (3)	C11—H11A	0.98
C1—C2	1.423 (4)	C11—H11B	0.98
C1—S1	1.749 (3)	C11—H11C	0.98
C2—C3	1.388 (4)	C12—H12A	0.98
C2—C14	1.527 (4)	C12—H12B	0.98
C3—C4	1.404 (4)	C12—H12C	0.98
C3—H3	0.95	C13—H13A	0.98
C4—C5	1.392 (4)	C13—H13B	0.98
C4—C10	1.535 (4)	C13—H13C	0.98
C5—C6	1.407 (4)	C14—O1	1.413 (3)
C5—H5	0.95	C14—O2	1.425 (4)
C6—C7	1.450 (4)	C14—H14	1
C7—N1	1.288 (4)	C15—O1	1.418 (3)
C7—H7	0.95	C15—H15A	0.98
C8—N1	1.485 (3)	C15—H15B	0.98
C8—C9	1.525 (4)	C15—H15C	0.98
C8—H8A	0.99	C16—O2	1.420 (5)
C8—H8B	0.99	C16—H16A	0.98
C9—C8ⁱ	1.525 (4)	C16—H16B	0.98
C9—H9A	0.99	C16—H16C	0.98
C9—H9B	0.99	Ni1—N1	1.907 (2)
C10—C11	1.532 (5)	Ni1—N1ⁱ	1.907 (2)
C10—C12	1.534 (4)	Ni1—S1ⁱ	2.1742 (8)
C10—C13	1.543 (4)	Ni1—S1	2.1742 (8)

C6—C1—C2	116.6 (2)	H11B—C11—H11C	109.5
C6—C1—S1	124.08 (19)	C10—C12—H12A	109.5
C2—C1—S1	119.2 (2)	C10—C12—H12B	109.5
C3—C2—C1	120.9 (2)	H12A—C12—H12B	109.5
C3—C2—C14	120.2 (2)	C10—C12—H12C	109.5
C1—C2—C14	118.9 (2)	H12A—C12—H12C	109.5
C2—C3—C4	122.9 (2)	H12B—C12—H12C	109.5
C2—C3—H3	118.5	C10—C13—H13A	109.5
C4—C3—H3	118.5	C10—C13—H13B	109.5
C5—C4—C3	116.2 (3)	H13A—C13—H13B	109.5
C5—C4—C10	123.0 (2)	C10—C13—H13C	109.5
C3—C4—C10	120.8 (2)	H13A—C13—H13C	109.5
C4—C5—C6	122.6 (2)	H13B—C13—H13C	109.5
C4—C5—H5	118.7	O1—C14—O2	111.6 (2)
C6—C5—H5	118.7	O1—C14—C2	108.2 (2)
C5—C6—C1	120.7 (2)	O2—C14—C2	112.8 (2)
C5—C6—C7	115.1 (2)	O1—C14—H14	108.1
C1—C6—C7	124.2 (2)	O2—C14—H14	108.1
N1—C7—C6	127.8 (3)	C2—C14—H14	108.1
N1—C7—H7	116.1	O1—C15—H15A	109.5
C6—C7—H7	116.1	O1—C15—H15B	109.5
N1—C8—C9	110.0 (2)	H15A—C15—H15B	109.5
N1—C8—H8A	109.7	O1—C15—H15C	109.5
C9—C8—H8A	109.7	H15A—C15—H15C	109.5
N1—C8—H8B	109.7	H15B—C15—H15C	109.5
C9—C8—H8B	109.7	O2—C16—H16A	109.5
H8A—C8—H8B	108.2	O2—C16—H16B	109.5
C8ⁱ—C9—C8	110.8 (3)	H16A—C16—H16B	109.5
C8ⁱ—C9—H9A	109.5	O2—C16—H16C	109.5
C8—C9—H9A	109.5	H16A—C16—H16C	109.5
C8ⁱ—C9—H9B	109.5	H16B—C16—H16C	109.5
C8—C9—H9B	109.5	C7—N1—C8	115.5 (2)
H9A—C9—H9B	108.1	C7—N1—Ni1	131.74 (19)
C11—C10—C12	109.5 (3)	C8—N1—Ni1	112.60 (18)
C11—C10—C4	108.8 (3)	C14—O1—C15	111.4 (2)
C12—C10—C4	109.6 (2)	C16—O2—C14	115.0 (3)
C11—C10—C13	108.5 (2)	N1—Ni1—N1ⁱ	90.49 (14)
C12—C10—C13	108.1 (3)	N1—Ni1—S1ⁱ	163.52 (7)
C4—C10—C13	112.3 (2)	N1ⁱ—Ni1—S1ⁱ	95.30 (7)
C10—C11—H11A	109.5	N1—Ni1—S1	95.30 (7)
C10—C11—H11B	109.5	N1ⁱ—Ni1—S1	163.52 (7)
H11A—C11—H11B	109.5	S1ⁱ—Ni1—S1	83.41 (4)
C10—C11—H11C	109.5	C1—S1—Ni1	109.86 (9)
H11A—C11—H11C	109.5

C6—C1—C2—C3	−0.9 (4)	C3—C4—C10—C13	179.5 (3)
S1—C1—C2—C3	−178.0 (2)	C3—C2—C14—O1	−21.8 (4)
C6—C1—C2—C14	−178.9 (3)	C1—C2—C14—O1	156.3 (3)
S1—C1—C2—C14	3.9 (4)	C3—C2—C14—O2	102.1 (3)
C1—C2—C3—C4	2.6 (5)	C1—C2—C14—O2	−79.8 (3)
C14—C2—C3—C4	−179.4 (3)	C6—C7—N1—C8	180.0 (3)
C2—C3—C4—C5	−1.4 (4)	C6—C7—N1—Ni1	4.6 (5)
C2—C3—C4—C10	179.7 (3)	C9—C8—N1—C7	106.0 (3)
C3—C4—C5—C6	−1.4 (4)	C9—C8—N1—Ni1	−77.7 (2)
C10—C4—C5—C6	177.4 (3)	O2—C14—O1—C15	65.2 (3)
C4—C5—C6—C1	3.1 (5)	C2—C14—O1—C15	−170.2 (3)
C4—C5—C6—C7	−177.7 (3)	O1—C14—O2—C16	54.4 (3)
C2—C1—C6—C5	−1.8 (4)	C2—C14—O2—C16	−67.6 (3)
S1—C1—C6—C5	175.1 (2)	C7—N1—Ni1—N1ⁱ	−149.1 (3)
C2—C1—C6—C7	179.0 (3)	C8—N1—Ni1—N1ⁱ	35.38 (15)
S1—C1—C6—C7	−4.0 (4)	C7—N1—Ni1—S1ⁱ	100.1 (3)
C5—C6—C7—N1	166.0 (3)	C8—N1—Ni1—S1ⁱ	−75.4 (3)
C1—C6—C7—N1	−14.8 (5)	C7—N1—Ni1—S1	15.4 (3)
N1—C8—C9—C8ⁱ	37.87 (15)	C8—N1—Ni1—S1	−160.07 (17)
C5—C4—C10—C11	−119.5 (3)	C6—C1—S1—Ni1	24.5 (3)
C3—C4—C10—C11	59.3 (3)	C2—C1—S1—Ni1	−158.6 (2)
C5—C4—C10—C12	120.8 (3)	N1—Ni1—S1—C1	−24.99 (12)
C3—C4—C10—C12	−60.4 (4)	N1ⁱ—Ni1—S1—C1	85.1 (3)
C5—C4—C10—C13	0.6 (4)	S1ⁱ—Ni1—S1—C1	171.52 (11)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

We are grateful to the CCLRC Daresbury Laboratory for the award of beamtime to carry out the diffraction experiment.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Beurskens, P. T., Beurskens, G., de Gelder, R., García-Granda, S., Gould, R. O., Israel, R. & Smits, J. M. M. (1999). The DIRDIF99 Program System. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Google Scholar
Bruker (2000). SMART (Version 5.054), SAINT (Version 6.02a), SADABS (Version 2.03), XPREP and SHELXTL/NT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Christensen, A. & McKenzie, C. J. (2004). Unpublished results. Google Scholar
Christensen, A., Jensen, S., McKee, V., McKenzie, C. J. & Munch, M. (1997). Inorg. Chem. 36, 6080–6085. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Parsons, S. & Gould, R. O. (2001). ROTAX. University of Edinburgh, Scotland. [Additions by Richard Cooper (Oxford) and Louis Farrugia (Glasgow), Version 26th November, 2001.] Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar

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Volume 60| Part 12| December 2004| Pages m1841-m1843

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