Bis[O-methyl (4-eth­oxy­phen­yl)dithio­phospho­nato-κ2S,S′]nickel(II)

Sewpersad, S.; Omondi, B.; Van Zyl, W.E.

doi:10.1107/S1600536812046314

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1483

doi:10.1107/S1600536812046314

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Bis[O-methyl (4-ethoxyphenyl)dithiophosphonato-κ²S,S′]nickel(II)

Shirveen Sewpersad,^a Bernard Omondi ^a and Werner E. Van Zyl ^a ^*

^aSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: vanzylw@ukzn.ac.za

(Received 4 November 2012; accepted 9 November 2012; online 14 November 2012)

In the title compound, [Ni(C₉H₁₂O₂PS₂)₂], the Ni^II atom resides on an inversion center and is coordinated by four S atoms [Ni—S = 2.2328 (4) and 2.2455 (3) Å] in a distorted square-planar geometry [S—Ni—S = 88.443 (13) and 91.557 (13)°]. In the crystal, molecules related by translation in [110] are linked into chains via weak C—H⋯O interactions. The crystal packing exhibits short intermolecular S⋯S contacts of 3.3366 (5) Å.

Related literature

For information on dithiophosphonate compounds, see: Van Zyl & Fackler (2000 ); Van Zyl (2010 ); Van Zyl & Woollins (2012 ). For related structures of nickel(II) dithiophosphonate complexes, see: Hartung (1967 ); Liu et al. (2004 ); Gray et al. (2004 ); Aragoni et al. (2007 ); Arca et al. (1997 ); Özcan et al. (2002 ).

Experimental

Crystal data

[Ni(C₉H₁₂O₂PS₂)₂]
M_r = 553.26
Monoclinic, P 2₁ /c
a = 13.5866 (5) Å
b = 6.4212 (2) Å
c = 14.1047 (5) Å
β = 109.389 (2)°
V = 1160.74 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 173 K
0.43 × 0.31 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.593, T_max = 0.737
19824 measured reflections
2850 independent reflections
2609 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.062
S = 1.07
2850 reflections
135 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.57	3.5123 (18)	171
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046314/cv5358sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046314/cv5358Isup2.hkl

checkCIF report

Comment top

The phosphor-1,1-dithiolate class of compounds is the heavier and softer congener of the popular phosphonate derivatives. It contains the S₂P functionality as a common feature and several sub-categories are known which include the dithiophosphato [S₂P(OR)₂]¯, (R = typically alkyl), dithiophosphinato [S₂PR₂]¯ (R = alkyl or aryl), and dithiophosphonato [S₂PR(OR')]¯, (R = typically aryl or ferrocenyl, R' = alkyl) monoanionic ligands. The latter may be described as a hybrid of the former two, and are also much less developed. Amongst all metals involved in the coordination chemistry of dithiophosphonato ligands, however, nickel(II) is by far the best represented (Van Zyl & Woollins, 2012) with the first X-ray structural report of a nickel(II) dithiophosphonate complex reported more than four decades ago (Hartung, 1967). The title complex, (I), was formed from the reaction between NiCl₂.6H₂0 and the ammonium salt of [S₂P(OMe)(4-C₆H₄OEt)] (molar ratio 1:2) in an aqueous/methanolic solution, the NH₄Cl by-product was dissolved and the precipitated product filtered off and washed with water. General and convenient methods to prepare dithiophosphonate salt derivatives have been reported (Van Zyl & Fackler, 2000).

The structure of (I) (Fig. 1) does not differ significantly from related Ni(II) complexes previously reported (Aragoni et al., 2007; Arca et al. (1997); Gray et al. (2004); Liu et al. (2004); Özcan et al., 2002). The Ni atom in (I) resides on an inversion center and is coordinated by four S atoms [Ni—S 2.2328 (4), 2.2455 (3) Å] in a distorted square-planar geometry [S—Ni—S 88.443 (13), 91.557 (13)°]. Molecules related by translation in [110] are linked into chains via weak C—H···O interactions (Table 1). The crystal packing exhibits short intermolecular S···S contacts of 3.3366 (5) Å.

Related literature top

For information on dithiophosphonate compounds, see: Van Zyl & Fackler (2000); Van Zyl (2010); Van Zyl & Woollins (2012). For related structures of nickel(II) dithiophosphonate complexes, see: Hartung (1967); Liu et al. (2004); Gray et al. (2004); Aragoni et al. (2007); Arca et al. (1997); Özcan et al. (2002).

Experimental top

A colorless methanol (40 ml) solution of NH₄[S₂P(OMe)(4-C₆H₄OEt)] (1.044 g, 4.474 mmol) was prepared. A second green solution of NiCl₂.6H₂0 (540 mg, 2.272 mmol) in deionized water (20 ml) was prepared, and added to the colorless solution with stirring over a period of 5 min. This resulted in a purple precipitate indicating the formation of the title complex. The precipitate was collected by vacuum filtration, washed with water (3 x 10 ml) and allowed to dry under vacuum for a period of 3 hrs, yielding a dry, free-flowing purple powder. Purple crystals suitable for X-ray analysis were grown by the slow diffusion of hexane into a dichloromethane solution of the title complex. Yield: 1.004 g, 41%. M.p. 168°C.

³¹P NMR (CDCl₃): δ (p.p.m.): 104.56. ¹H NMR (CDCl₃): δ (p.p.m.): 7.94 (2H, dd, J(³¹P-¹H) = 12.76 Hz, J(¹H -¹H) = 10.08 Hz, o-ArH), 6.95 (2H, dd, J(³¹P-¹H) = 8.76 Hz, J(¹H-¹H) = 3.08 Hz, m-ArH), 4.07 (2H, quart, J(¹H-¹H) = 6.96 Hz, ArOCH₂), 3.96 (3H, d, J(³¹P-¹H) = 14.8 Hz, POCH₃), 1.41 (3H, t, J(¹H-¹H) = 6.98 Hz, ArOCH₂CH₃). ¹³C NMR (CDCl₃): δ (p.p.m.): 162.64 (p-ArC), 131.78 (m-ArC), 128.68 (Ar—C_ipso), 114.62 (o-ArC), 63.99 (ArOCH₂), 52.73 (OCH₃), 14.85 (ArOCH₂CH₃).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex showing the atomic numbering and 50% probability displacement ellispoids [symmetry code: (i)-x + 2,-y + 2,-z + 2]. H atoms omitted for clarity.

Bis[O-methyl (4-ethoxyphenyl)dithiophosphonato- κ²S,S']nickel(II) top

Crystal data top

[Ni(C₉H₁₂O₂PS₂)₂]	F(000) = 572
M_r = 553.26	D_x = 1.583 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19824 reflections
a = 13.5866 (5) Å	θ = 2.9–28.4°
b = 6.4212 (2) Å	µ = 1.36 mm⁻¹
c = 14.1047 (5) Å	T = 173 K
β = 109.389 (2)°	Block, purple
V = 1160.74 (7) Å³	0.43 × 0.31 × 0.24 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD diffractometer	2850 independent reflections
Radiation source: fine-focus sealed tube	2609 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→17
T_min = 0.593, T_max = 0.737	k = −8→8
19824 measured reflections	l = −18→18

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0281P)² + 0.7956P] where P = (F_o² + 2F_c²)/3
2850 reflections	(Δ/σ)_max = 0.001
135 parameters	Δρ_max = 0.56 e Å⁻³
2 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Ni(C₉H₁₂O₂PS₂)₂]	V = 1160.74 (7) Å³
M_r = 553.26	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5866 (5) Å	µ = 1.36 mm⁻¹
b = 6.4212 (2) Å	T = 173 K
c = 14.1047 (5) Å	0.43 × 0.31 × 0.24 mm
β = 109.389 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2850 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2609 reflections with I > 2σ(I)
T_min = 0.593, T_max = 0.737	R_int = 0.036
19824 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	2 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.07	Δρ_max = 0.56 e Å⁻³
2850 reflections	Δρ_min = −0.44 e Å⁻³
135 parameters

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
C1	0.70393 (11)	0.8288 (2)	0.85131 (10)	0.0149 (3)
C2	0.68704 (11)	0.6590 (2)	0.90614 (11)	0.0175 (3)
H2	0.7398	0.5564	0.9306	0.021*
C3	0.59371 (12)	0.6398 (2)	0.92488 (12)	0.0196 (3)
H3	0.5823	0.5237	0.9617	0.024*
C4	0.51619 (11)	0.7913 (2)	0.88969 (11)	0.0167 (3)
C5	0.53108 (12)	0.9588 (3)	0.83320 (12)	0.0202 (3)
H5	0.4777	1.0598	0.8075	0.024*
C6	0.62531 (12)	0.9759 (3)	0.81507 (12)	0.0211 (3)
H6	0.6362	1.0905	0.7771	0.025*
C7	0.34352 (11)	0.9068 (2)	0.87693 (12)	0.0199 (3)
H7A	0.3191	0.9120	0.8026	0.024*
H7B	0.3662	1.0480	0.9033	0.024*
C8	0.25769 (12)	0.8303 (3)	0.91356 (13)	0.0258 (3)
H8A	0.2401	0.6862	0.8915	0.039*
H8B	0.1959	0.9186	0.8859	0.039*
H8C	0.2812	0.8364	0.9871	0.039*
C9	0.88481 (12)	0.8281 (3)	0.67579 (12)	0.0243 (3)
H9A	0.9184	0.9650	0.6891	0.036*
H9B	0.8562	0.8052	0.6031	0.036*
H9C	0.9363	0.7197	0.7065	0.036*
O1	0.42818 (8)	0.76065 (18)	0.91366 (8)	0.0210 (2)
O2	0.80067 (8)	0.81965 (17)	0.71841 (7)	0.0172 (2)
P1	0.82716 (3)	0.87053 (6)	0.83456 (3)	0.01290 (9)
S1	0.88018 (3)	1.16115 (5)	0.87163 (3)	0.01505 (9)
S2	0.94269 (3)	0.69659 (5)	0.92450 (3)	0.01547 (9)
Ni1	1.0000	1.0000	1.0000	0.01236 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0126 (6)	0.0163 (7)	0.0142 (6)	−0.0026 (5)	0.0024 (5)	−0.0008 (5)
C2	0.0168 (7)	0.0162 (7)	0.0186 (7)	0.0021 (5)	0.0050 (5)	0.0025 (6)
C3	0.0200 (7)	0.0181 (7)	0.0218 (7)	0.0007 (6)	0.0085 (6)	0.0061 (6)
C4	0.0156 (6)	0.0187 (7)	0.0157 (6)	−0.0013 (6)	0.0050 (5)	−0.0007 (6)
C5	0.0152 (7)	0.0194 (7)	0.0246 (7)	0.0024 (6)	0.0050 (6)	0.0065 (6)
C6	0.0177 (7)	0.0201 (7)	0.0252 (7)	0.0005 (6)	0.0067 (6)	0.0088 (6)
C7	0.0171 (7)	0.0192 (7)	0.0239 (7)	0.0027 (6)	0.0074 (6)	−0.0006 (6)
C8	0.0209 (7)	0.0271 (9)	0.0324 (9)	0.0015 (6)	0.0127 (7)	−0.0004 (7)
C9	0.0219 (7)	0.0328 (9)	0.0212 (7)	0.0004 (7)	0.0113 (6)	−0.0025 (7)
O1	0.0176 (5)	0.0231 (6)	0.0251 (5)	0.0041 (4)	0.0107 (4)	0.0069 (5)
O2	0.0164 (5)	0.0212 (5)	0.0133 (5)	−0.0019 (4)	0.0038 (4)	−0.0016 (4)
P1	0.01195 (16)	0.01266 (17)	0.01283 (16)	−0.00089 (13)	0.00241 (13)	0.00025 (13)
S1	0.01442 (16)	0.01179 (16)	0.01655 (16)	−0.00085 (12)	0.00194 (13)	0.00125 (13)
S2	0.01453 (16)	0.01163 (17)	0.01733 (16)	0.00058 (12)	0.00138 (13)	−0.00038 (13)
Ni1	0.01162 (12)	0.01061 (13)	0.01350 (12)	−0.00046 (9)	0.00235 (9)	0.00017 (9)

Geometric parameters (Å, º) top

C1—C6	1.390 (2)	C8—H8A	0.9800
C1—C2	1.399 (2)	C8—H8B	0.9800
C1—P1	1.7871 (14)	C8—H8C	0.9800
C2—C3	1.384 (2)	C9—O2	1.4585 (17)
C2—H2	0.9500	C9—H9A	0.9800
C3—C4	1.398 (2)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—O1	1.3606 (17)	O2—P1	1.5902 (10)
C4—C5	1.393 (2)	P1—S2	1.9996 (5)
C5—C6	1.391 (2)	P1—S1	2.0061 (5)
C5—H5	0.9500	P1—Ni1	2.8306 (4)
C6—H6	0.9500	S1—Ni1	2.2455 (3)
C7—O1	1.4408 (18)	S2—Ni1	2.2328 (4)
C7—C8	1.506 (2)	Ni1—S2ⁱ	2.2328 (4)
C7—H7A	0.9900	Ni1—S1ⁱ	2.2455 (3)
C7—H7B	0.9900	Ni1—P1ⁱ	2.8306 (4)

C6—C1—C2	119.07 (13)	O2—C9—H9C	109.5
C6—C1—P1	119.25 (11)	H9A—C9—H9C	109.5
C2—C1—P1	121.52 (11)	H9B—C9—H9C	109.5
C3—C2—C1	120.23 (14)	C4—O1—C7	118.63 (12)
C3—C2—H2	119.9	C9—O2—P1	118.47 (9)
C1—C2—H2	119.9	O2—P1—C1	101.76 (6)
C2—C3—C4	120.03 (14)	O2—P1—S2	113.60 (4)
C2—C3—H3	120.0	C1—P1—S2	113.88 (5)
C4—C3—H3	120.0	O2—P1—S1	113.49 (4)
O1—C4—C5	124.08 (14)	C1—P1—S1	112.10 (5)
O1—C4—C3	115.59 (13)	S2—P1—S1	102.47 (2)
C5—C4—C3	120.33 (13)	O2—P1—Ni1	138.74 (4)
C6—C5—C4	118.91 (14)	C1—P1—Ni1	119.49 (5)
C6—C5—H5	120.5	S2—P1—Ni1	51.639 (13)
C4—C5—H5	120.5	S1—P1—Ni1	51.985 (12)
C1—C6—C5	121.39 (14)	P1—S1—Ni1	83.279 (16)
C1—C6—H6	119.3	P1—S2—Ni1	83.755 (17)
C5—C6—H6	119.3	S2ⁱ—Ni1—S2	180.0
O1—C7—C8	106.33 (13)	S2ⁱ—Ni1—S1	91.557 (13)
O1—C7—H7A	110.5	S2—Ni1—S1	88.443 (13)
C8—C7—H7A	110.5	S2ⁱ—Ni1—S1ⁱ	88.443 (13)
O1—C7—H7B	110.5	S2—Ni1—S1ⁱ	91.557 (13)
C8—C7—H7B	110.5	S1—Ni1—S1ⁱ	180.0
H7A—C7—H7B	108.7	S2ⁱ—Ni1—P1ⁱ	44.606 (11)
C7—C8—H8A	109.5	S2—Ni1—P1ⁱ	135.394 (11)
C7—C8—H8B	109.5	S1—Ni1—P1ⁱ	135.263 (12)
H8A—C8—H8B	109.5	S1ⁱ—Ni1—P1ⁱ	44.737 (12)
C7—C8—H8C	109.5	S2ⁱ—Ni1—P1	135.394 (11)
H8A—C8—H8C	109.5	S2—Ni1—P1	44.606 (11)
H8B—C8—H8C	109.5	S1—Ni1—P1	44.737 (12)
O2—C9—H9A	109.5	S1ⁱ—Ni1—P1	135.263 (12)
O2—C9—H9B	109.5	P1ⁱ—Ni1—P1	180.0
H9A—C9—H9B	109.5

C6—C1—C2—C3	−0.8 (2)	C1—P1—S2—Ni1	−109.65 (5)
P1—C1—C2—C3	174.69 (12)	S1—P1—S2—Ni1	11.639 (18)
C1—C2—C3—C4	−0.5 (2)	P1—S2—Ni1—S2ⁱ	67 (100)
C2—C3—C4—O1	−178.75 (14)	P1—S2—Ni1—S1	−10.140 (16)
C2—C3—C4—C5	1.9 (2)	P1—S2—Ni1—S1ⁱ	169.860 (16)
O1—C4—C5—C6	178.78 (14)	P1—S2—Ni1—P1ⁱ	180.0
C3—C4—C5—C6	−1.9 (2)	P1—S1—Ni1—S2ⁱ	−169.884 (16)
C2—C1—C6—C5	0.7 (2)	P1—S1—Ni1—S2	10.116 (16)
P1—C1—C6—C5	−174.82 (13)	P1—S1—Ni1—S1ⁱ	−11 (100)
C4—C5—C6—C1	0.6 (2)	P1—S1—Ni1—P1ⁱ	180.0
C5—C4—O1—C7	1.5 (2)	O2—P1—Ni1—S2ⁱ	97.35 (7)
C3—C4—O1—C7	−177.89 (13)	C1—P1—Ni1—S2ⁱ	−81.64 (6)
C8—C7—O1—C4	178.93 (13)	S2—P1—Ni1—S2ⁱ	180.000 (1)
C9—O2—P1—C1	−177.47 (12)	S1—P1—Ni1—S2ⁱ	14.48 (2)
C9—O2—P1—S2	−54.64 (12)	O2—P1—Ni1—S2	−82.65 (7)
C9—O2—P1—S1	61.90 (12)	C1—P1—Ni1—S2	98.36 (6)
C9—O2—P1—Ni1	3.43 (15)	S1—P1—Ni1—S2	−165.52 (2)
C6—C1—P1—O2	−74.92 (13)	O2—P1—Ni1—S1	82.87 (7)
C2—C1—P1—O2	109.62 (12)	C1—P1—Ni1—S1	−96.12 (6)
C6—C1—P1—S2	162.44 (11)	S2—P1—Ni1—S1	165.52 (2)
C2—C1—P1—S2	−13.02 (14)	O2—P1—Ni1—S1ⁱ	−97.13 (7)
C6—C1—P1—S1	46.67 (13)	C1—P1—Ni1—S1ⁱ	83.88 (6)
C2—C1—P1—S1	−128.78 (11)	S2—P1—Ni1—S1ⁱ	−14.48 (2)
C6—C1—P1—Ni1	104.40 (12)	S1—P1—Ni1—S1ⁱ	180.0
C2—C1—P1—Ni1	−71.06 (13)	O2—P1—Ni1—P1ⁱ	−20 (100)
O2—P1—S1—Ni1	−134.48 (4)	C1—P1—Ni1—P1ⁱ	161 (100)
C1—P1—S1—Ni1	110.92 (5)	S2—P1—Ni1—P1ⁱ	63 (100)
S2—P1—S1—Ni1	−11.583 (18)	S1—P1—Ni1—P1ⁱ	−102 (100)
O2—P1—S2—Ni1	134.46 (5)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱⁱ	0.95	2.57	3.5123 (18)	171

Symmetry code: (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₁₂O₂PS₂)₂]
M_r	553.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.5866 (5), 6.4212 (2), 14.1047 (5)
β (°)	109.389 (2)
V (Å³)	1160.74 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.43 × 0.31 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.593, 0.737
No. of measured, independent and observed [I > 2σ(I)] reflections	19824, 2850, 2609
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.062, 1.07
No. of reflections	2850
No. of parameters	135
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.44

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.57	3.5123 (18)	171

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

The authors thank the National Research Foundation (NRF) and UKZN for financial support.

References

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