Tri­carbonyl(3-carboxy­propyl)(η5-cyclo­penta­dienyl)­tungsten(II)

Friedrich, H.B.; Howie, R.A.; Onani, M.O.

doi:10.1107/S1600536804025371

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 11| November 2004| Pages m1641-1643

https://doi.org/10.1107/S1600536804025371

Tricarbonyl(3-carboxypropyl)(η⁵-cyclopentadienyl)tungsten(II)

Holger B. Friedrich,^a R. Alan Howie ^b ^* and Martin O. Onani ^c

^aSchool of Pure and Applied Chemistry, Howard College, University of KwaZulu–Natal, Durban 4041, South Africa, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and ^cDepartment of Chemistry, University of Transkei, Private Bag X1, UNITRA, 5117 Umtata, South Africa
^*Correspondence e-mail: r.a.howie@abdn.ac.uk

(Received 4 October 2004; accepted 8 October 2004; online 16 October 2004)

The bond lengths and angles in the title compound, [W(C₅H₅)(C₄H₇O₂)(CO)₃], are as expected for a molecule of this kind. The presence of the carboxylic acid group leads, however, to the creation of hydrogen-bonded dimers consisting of pairs of centrosymmetrically related molecules.

Comment

The determination of the structure of the title compound, (I), was undertaken as part of our ongoing study of the chemistry of heterodinuclear compounds (Friedrich et al., 2004 ). Fig. 1 is a drawing of the molecule and selected bond lengths and angles are given in Table 1. In both cases, the participation of the cyclopentadienyl (Cp) group in the coordination of W is represented, purely for convenience, by the notional bond W—Cg1 where Cg1 is the centroid of the five-membered cyclopentadienyl ring. On this basis, W is effectively five-coordinate in a distorted square-pyramidal environment with apical Cp. This arrangement creates the appearance of a stool with Cp as its seat and the three carbonyl groups and the carboxy ligand as its feet, four in number.

The bond lengths and angles given in Table 1 are unremarkable. The same is true for the W—C_Cp bonds in the range 2.312 (4)–2.376 (4) Å and the C—C bonds and C—C—C angles of Cp in the ranges 1.385 (7)–1.431 (7) Å and 107.3 (5)–108.4 (5)°, respectively. In the drawing of the unit-cell contents (Fig. 2) a notable feature is the presence of the hydrogen-bonded dimer involving a pair of centrosymmetrically related molecules. The hydrogen-bond parameters are given in Table 2. No other intermolecular contacts of any significance, other than van der Waals interactions, are present in the structure. Similar hydrogen-bonded dimers are present in the structures of the analogous compounds [Cp(CO)₃MoCH₂COOH] and [Cp(CO)₂FeCH₂COOH] (Ariyaratne et al., 1969 ). Despite the limited quality of the refinements, these authors suggested that there was evidence to support some form of interaction between the metal (Mo or Fe) and the carboxylic acid group. There is no evidence for such an interaction in (I), which would be less likely in any case because of the length of the alkyl chain. There is perhaps a case for redetermining the earlier structures.

Figure 1
The molecule of (I

). Non-H atoms are shown as 50% probability displacement ellipsoids and H atoms as small circles of arbitrary radii. The dashed bond joins W and the centroid of the Cp ring.

Figure 2
The unit-cell contents of (I

). Non-H atoms are shown as 50% probability displacement ellipsoids and H atoms as small circles of arbitrary radii. All H atoms other than those involved in hydrogen bonding (dashed lines) have been omitted. Selected atoms are labelled. [Symmetry codes: (i) x, ½ − y, ½ + z; (ii) 1 − x, 1 − y, 1 − z; (iii) 1 − x, ½ + y, ½ − z.]

Experimental

Compound (I) was obtained by hydrolysis brought about by the presence of water in a dichloromethane/hexane solution of [Cp(CO)₃W(CH₂)₃C(O)Mo(CO)(PMe₃)(PPh₃)Cp] (Onani, 2002 ). Yellow crystals suitable for analysis were obtained after 5 d of slow diffusion of hexane into a dichloromethane solution of (I) kept at 278 K.

Crystal data

[W(C₅H₅)(C₄H₇O₂)(CO)₃]
M_r = 420.07
Monoclinic, P2₁/c
a = 14.265 (2) Å
b = 8.1540 (11) Å
c = 11.229 (2) Å
β = 102.800 (15)°
V = 1273.7 (3) Å³
Z = 4
D_x = 2.191 Mg m⁻³
Mo Kα radiation
Cell parameters from 25 reflections
θ = 11.8–12.2°
μ = 9.08 mm⁻¹
T = 295 (2) K
Rhomb, yellow
0.40 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
ω–2θ scans
Absorption correction: refined from ΔF (DIFABS; Walker & Stuart, 1983 ) T_min = 0.011, T_max = 0.066
5154 measured reflections
2241 independent reflections
2053 reflections with I > 2σ(I)
R_int = 0.035
θ_max = 25.0°
h = −16 → 16
k = −1 → 9
l = −13 → 13
3 standard reflections frequency: 120 min intensity decay: 7%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.072
S = 1.08
2241 reflections
164 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0482P)² + 0.7777P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 1.00 e Å⁻³
Δρ_min = −1.17 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

W1—Cg1	2.012 (2)
W1—C1	1.975 (5)
W1—C2	1.986 (5)
W1—C3	1.974 (5)
W1—C4	2.319 (4)
O1—C1	1.147 (6)
O2—C2	1.143 (6)
O3—C3	1.135 (5)
O4—C7	1.305 (5)
O5—C7	1.211 (5)
C4—C5	1.509 (6)
C5—C6	1.535 (5)
C6—C7	1.494 (6)

Cg1—W1—C1	129.02 (15)
Cg1—W1—C2	118.89 (18)
Cg1—W1—C3	123.62 (16)
Cg1—W1—C4	110.12 (13)
C1—W1—C2	75.58 (19)
C1—W1—C3	106.84 (18)
C1—W1—C4	75.15 (16)
C2—W1—C3	78.1 (2)
C2—W1—C4	130.95 (19)
C3—W1—C4	73.91 (17)

C1—W1—C4—C5	50.8 (3)
C2—W1—C4—C5	106.0 (4)
C3—W1—C4—C5	163.7 (4)
W1—C4—C5—C6	167.4 (3)
C4—C5—C6—O4	−67.5 (6)
C4—C5—C6—O5	−82.2 (3)
Note: Cg1 is the centroid of the cyclopentadienyl ring.

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5ⁱ	0.82	1.84	2.653 (5)	169
Symmetry code: (i) 1-x,1-y,1-z.

Presented here is a rerefinement, after suitable transformation of the unit-cell parameters and the atomic coordinates and reindexing of the intensity data, of a structure previously solved and fully refined in the space group P $[\overline 1]$ . The need for the rerefinement was clearly indicated by a checkCIF level A alert and the form it should take was revealed by recourse to the ADDSYM routine of PLATON (Spek, 2003 ). Close examination of a drawing of the content of the original, supposedly triclinic, unit cell fully confirmed the ADDSYM findings. Further support for the rerefinement reported here is the improvement in R [I > 2σ(I)] from 0.031 for the triclinic model to the value of 0.026 for the present refinement (with the number of refined parameters now half that of the triclinic refinement). In the final stages of the present refinement, H atoms were placed in calculated positions, with X—H = 0.82, 0.93 and 0.97 Å for hydroxyl, cyclopentadienyl and methylene H atoms, respectively, and refined using a riding model, with U_iso(H) = 1.5U_eq(O) or 1.2U_eq(C), as appropriate for the nature of X. The position of the hydroxyl group in terms of its rotation about the C—O bond was also refined. The highest residual electron-density peak is 0.99 Å from atom W1.The deepest residual electron-density hole lies 0.69 Å from atom W1.

Data collection: CAD-4/PC (Enraf–Nonius, 1994 ); cell refinement: CAD-4/PC; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97 and PLATON (Spek, 2003).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804025371/lh6288sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804025371/lh6288Isup2.hkl

Computing details top

Data collection: CAD-4-PC (Enraf-Nonius, 1994); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 and PLATON (Spek, 2003).

Tricarbonyl(3-carboxypropyl)(η⁵-cyclopentadienyl)tungsten(II) top

Crystal data top

[W(C₅H₅)(C₄H₇O₂)(CO)₃]	F(000) = 792
M_r = 420.07	D_x = 2.191 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ybc	Cell parameters from 25 reflections
a = 14.265 (2) Å	θ = 11.8–12.2°
b = 8.1540 (11) Å	µ = 9.08 mm⁻¹
c = 11.229 (2) Å	T = 295 K
β = 102.800 (15)°	Rhomb, yellow
V = 1273.7 (3) Å³	0.40 × 0.30 × 0.30 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.0°, θ_min = 2.9°
ω–2θ scans	h = −16→16
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	k = −1→9
T_min = 0.011, T_max = 0.066	l = −13→13
5154 measured reflections	3 standard reflections every 120 min
2241 independent reflections	intensity decay: 7%

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0482P)² + 0.7777P] where P = (F_o² + 2F_c²)/3
2241 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −1.17 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. Distance (1 entry) and angles (4 entries) involving Cg1 (the centroid of the cyclopentadienyl ring) have been entered by hand into the relevant sections of the cif for ease of reference.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.4564 (0.0323) x + 4.7000 (0.0174) y + 7.4911 (0.0205) z = 8.9230 (0.0227)

* -0.0042 (0.0029) C8 * 0.0026 (0.0030) C9 * 0.0001 (0.0031) C10 * -0.0027 (0.0032) C11 * 0.0043 (0.0030) C12 - 2.0105 (0.0021) W1 - 3.2724 (0.0062) C1 - 2.9105 (0.0073) C2 - 3.0909 (0.0066) C3

Rms deviation of fitted atoms = 0.0032

2.8996 (0.0447) x + 4.0968 (0.0144) y + 8.6965 (0.0214) z = 4.3963 (0.0356)

Angle to previous plane (with approximate e.s.d.) = 9.01 (0.38)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C3 1.1472 (0.0028) W1 3.1471 (0.0060) C8 3.3253 (0.0063) C9 3.2498 (0.0064) C10 3.0270 (0.0066) C11 2.9704 (0.0066) C12 - 0.6372 (0.0067) O1 - 0.6798 (0.0093) O2 - 0.6125 (0.0071) O3

Rms deviation of fitted atoms = 0.0000

3.1651 (0.0224) x + 4.0974 (0.0075) y + 8.5980 (0.0115) z = 3.9634 (0.0183)

Angle to previous plane (with approximate e.s.d.) = 1.10 (0.31)

* 0.0000 (0.0000) O1 * 0.0000 (0.0000) O2 * 0.0000 (0.0000) O3

Rms deviation of fitted atoms = 0.0000

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.

H atoms placed in calculated positions with X—H 0.82, 0.93 and 0.97 A for hydroxyl, cyclopentadienyl and methylene H, respectively, and refined with a riding model with U_iso(H) = 1.5Ueq(O) or 1.2Ueq(C) as appropriate for the nature of X. The position of the hydroxyl group in terms of its rotation about the C—O bond was also refined.

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

	x	y	z	U_iso*/U_eq
W1	0.800314 (12)	0.48662 (2)	0.141360 (15)	0.03491 (11)
O1	0.8107 (2)	0.1070 (5)	0.1116 (3)	0.0607 (9)
O2	0.9002 (3)	0.4342 (6)	−0.0773 (4)	0.0759 (11)
O3	0.6469 (3)	0.6263 (5)	−0.0757 (3)	0.0655 (9)
O4	0.4419 (2)	0.3506 (5)	0.3892 (3)	0.0621 (9)
H4	0.4325	0.4221	0.4365	0.093*
O5	0.5900 (3)	0.4493 (5)	0.4377 (3)	0.0567 (8)
C1	0.8043 (3)	0.2463 (6)	0.1213 (4)	0.0394 (9)
C2	0.8645 (4)	0.4546 (7)	0.0031 (5)	0.0523 (12)
C3	0.7026 (3)	0.5712 (6)	0.0022 (4)	0.0465 (10)
C4	0.6532 (3)	0.3944 (5)	0.1705 (4)	0.0408 (9)
H4A	0.6202	0.4871	0.1966	0.049*
H4B	0.6154	0.3596	0.0918	0.049*
C5	0.6527 (3)	0.2565 (5)	0.2599 (4)	0.0439 (10)
H5A	0.7003	0.2791	0.3343	0.053*
H5B	0.6710	0.1555	0.2254	0.053*
C6	0.5543 (3)	0.2328 (5)	0.2916 (4)	0.0471 (10)
H6A	0.5050	0.2374	0.2167	0.057*
H6B	0.5522	0.1243	0.3263	0.057*
C7	0.5312 (3)	0.3564 (5)	0.3790 (4)	0.0425 (9)
C8	0.8027 (4)	0.7247 (6)	0.2584 (4)	0.0564 (12)
H8	0.7539	0.8020	0.2378	0.068*
C9	0.8052 (3)	0.5954 (6)	0.3390 (4)	0.0512 (11)
H9	0.7585	0.5715	0.3825	0.061*
C10	0.8902 (5)	0.5065 (5)	0.3438 (6)	0.0542 (15)
H10	0.9095	0.4135	0.3907	0.065*
C11	0.9411 (3)	0.5829 (7)	0.2652 (5)	0.0563 (12)
H11	0.9998	0.5488	0.2510	0.068*
C12	0.8885 (4)	0.7185 (6)	0.2124 (5)	0.0584 (12)
H12	0.9059	0.7914	0.1574	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
W1	0.03475 (17)	0.03509 (14)	0.03487 (16)	0.00048 (5)	0.00766 (11)	−0.00016 (5)
O1	0.063 (2)	0.047 (2)	0.072 (2)	0.0105 (16)	0.0141 (17)	−0.0033 (17)
O2	0.078 (3)	0.096 (3)	0.066 (2)	−0.004 (3)	0.044 (2)	−0.008 (2)
O3	0.064 (2)	0.071 (2)	0.055 (2)	0.0085 (19)	−0.0007 (17)	0.0166 (18)
O4	0.0410 (18)	0.081 (3)	0.068 (2)	−0.0133 (17)	0.0219 (16)	−0.0192 (19)
O5	0.0394 (19)	0.072 (2)	0.060 (2)	−0.0114 (18)	0.0157 (17)	−0.016 (2)
C1	0.031 (2)	0.040 (3)	0.046 (2)	0.0026 (16)	0.0054 (17)	−0.0030 (17)
C2	0.052 (3)	0.054 (3)	0.053 (3)	−0.003 (2)	0.017 (3)	−0.001 (2)
C3	0.053 (3)	0.043 (2)	0.045 (2)	0.000 (2)	0.014 (2)	0.001 (2)
C4	0.035 (2)	0.049 (2)	0.038 (2)	−0.0004 (18)	0.0072 (17)	0.0001 (18)
C5	0.042 (2)	0.041 (2)	0.050 (2)	0.0016 (18)	0.014 (2)	0.0023 (19)
C6	0.045 (2)	0.043 (2)	0.053 (2)	−0.0043 (19)	0.012 (2)	0.0041 (19)
C7	0.038 (2)	0.048 (2)	0.042 (2)	−0.0002 (19)	0.0117 (18)	0.0103 (19)
C8	0.063 (3)	0.041 (2)	0.061 (3)	0.001 (2)	0.004 (2)	−0.012 (2)
C9	0.054 (3)	0.057 (3)	0.043 (2)	−0.007 (2)	0.011 (2)	−0.014 (2)
C10	0.059 (4)	0.057 (3)	0.042 (3)	−0.001 (2)	0.001 (3)	−0.0020 (18)
C11	0.039 (2)	0.070 (3)	0.056 (3)	−0.010 (2)	0.000 (2)	−0.008 (3)
C12	0.062 (3)	0.046 (3)	0.064 (3)	−0.022 (2)	0.006 (2)	−0.004 (2)

Geometric parameters (Å, º) top

W1—Cg1	2.012 (2)	C4—H4B	0.9700
W1—C1	1.975 (5)	C5—C6	1.535 (5)
W1—C2	1.986 (5)	C5—H5A	0.9700
W1—C3	1.974 (5)	C5—H5B	0.9700
W1—C11	2.312 (4)	C6—C7	1.494 (6)
W1—C12	2.313 (4)	C6—H6A	0.9700
W1—C4	2.319 (4)	C6—H6B	0.9700
W1—C8	2.340 (4)	C8—C9	1.385 (7)
W1—C10	2.355 (6)	C8—C12	1.431 (7)
W1—C9	2.376 (4)	C8—H8	0.9300
O1—C1	1.147 (6)	C9—C10	1.403 (8)
O2—C2	1.143 (6)	C9—H9	0.9300
O3—C3	1.135 (5)	C10—C11	1.406 (8)
O4—C7	1.305 (5)	C10—H10	0.9300
O4—H4	0.8200	C11—C12	1.392 (7)
O5—C7	1.211 (5)	C11—H11	0.9300
C4—C5	1.509 (6)	C12—H12	0.9300
C4—H4A	0.9700

Cg1—W1—C1	129.02 (15)	W1—C4—H4B	107.7
Cg1—W1—C2	118.89 (18)	H4A—C4—H4B	107.1
Cg1—W1—C3	123.62 (16)	C4—C5—C6	112.8 (3)
Cg1—W1—C4	110.12 (13)	C4—C5—H5A	109.0
C1—W1—C2	75.58 (19)	C6—C5—H5A	109.0
C1—W1—C3	106.84 (18)	C4—C5—H5B	109.0
C1—W1—C4	75.15 (16)	C6—C5—H5B	109.0
C2—W1—C3	78.1 (2)	H5A—C5—H5B	107.8
C2—W1—C4	130.95 (19)	C7—C6—C5	114.5 (4)
C3—W1—C4	73.91 (17)	C7—C6—H6A	108.6
C3—W1—C11	136.4 (2)	C5—C6—H6A	108.6
C1—W1—C11	111.26 (19)	C7—C6—H6B	108.6
C2—W1—C11	91.5 (2)	C5—C6—H6B	108.6
C3—W1—C12	102.8 (2)	H6A—C6—H6B	107.6
C1—W1—C12	145.43 (17)	O5—C7—O4	123.2 (4)
C2—W1—C12	93.8 (2)	O5—C7—C6	123.5 (4)
C11—W1—C12	35.04 (19)	O4—C7—C6	113.3 (4)
C11—W1—C4	135.87 (17)	C9—C8—C12	108.0 (5)
C12—W1—C4	131.05 (18)	C9—C8—W1	74.4 (3)
C3—W1—C8	94.28 (18)	C12—C8—W1	71.1 (3)
C1—W1—C8	152.86 (17)	C9—C8—H8	126.0
C2—W1—C8	126.6 (2)	C12—C8—H8	126.0
C11—W1—C8	58.51 (19)	W1—C8—H8	120.4
C12—W1—C8	35.81 (18)	C8—C9—C10	108.3 (5)
C4—W1—C8	95.24 (17)	C8—C9—W1	71.5 (3)
C3—W1—C10	151.43 (19)	C10—C9—W1	71.9 (3)
C1—W1—C10	98.92 (16)	C8—C9—H9	125.8
C2—W1—C10	121.1 (2)	C10—C9—H9	125.8
C11—W1—C10	35.1 (2)	W1—C9—H9	122.4
C12—W1—C10	58.17 (18)	C9—C10—C11	108.0 (5)
C4—W1—C10	101.69 (19)	C9—C10—W1	73.6 (3)
C8—W1—C10	57.57 (17)	C11—C10—W1	70.8 (3)
C3—W1—C9	118.59 (18)	C9—C10—H10	126.0
C1—W1—C9	118.74 (17)	C11—C10—H10	126.0
C2—W1—C9	148.82 (19)	W1—C10—H10	121.3
C11—W1—C9	57.98 (17)	C12—C11—C10	108.4 (5)
C12—W1—C9	58.12 (18)	C12—C11—W1	72.5 (3)
C4—W1—C9	80.20 (16)	C10—C11—W1	74.1 (3)
C8—W1—C9	34.14 (17)	C12—C11—H11	125.8
C10—W1—C9	34.51 (19)	C10—C11—H11	125.8
C7—O4—H4	109.5	W1—C11—H11	119.4
O1—C1—W1	177.1 (4)	C11—C12—C8	107.3 (5)
O2—C2—W1	178.8 (5)	C11—C12—W1	72.5 (3)
O3—C3—W1	177.1 (4)	C8—C12—W1	73.1 (3)
C5—C4—W1	118.3 (3)	C11—C12—H12	126.4
C5—C4—H4A	107.7	C8—C12—H12	126.4
W1—C4—H4A	107.7	W1—C12—H12	119.9
C5—C4—H4B	107.7

C1—W1—C4—C5	50.8 (3)	W1—C4—C5—C6	167.4 (3)
C2—W1—C4—C5	106.0 (4)	C4—C5—C6—O4	−67.5 (6)
C3—W1—C4—C5	163.7 (4)	C4—C5—C6—O5	−82.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱ	0.82	1.84	2.653 (5)	169

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank O. Munro for collecting the intensity data. We further thank the DAAD (Germany), NRF (South Africa) and the University of KwaZulu–Natal for support.

References

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Volume 60| Part 11| November 2004| Pages m1641-1643

https://doi.org/10.1107/S1600536804025371

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