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

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Poly[[di­aqua­bis­­[μ-2-(4-fluoro­phen­­oxy)acetato-κ2O1:O1′]magnesium] 0.4-hydrate]

aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au

(Received 31 July 2012; accepted 9 August 2012; online 15 August 2012)

In the title compound, {[Mg(C8H6FO3)2(H2O)2]·0.4H2O}n, slightly distorted octa­hedral MgO6 complex units have crystallographic inversion symmetry, the coordination polyhedron comprising two trans-related water mol­ecules and four carboxyl O-atom donors, two of which are bridging. Within the two-dimensional complex polymer which is parallel to (100), coordinating water mol­ecules form inter­molecular O—H⋯O hydrogen bonds with carboxyl­ate and phen­oxy O-atom acceptors, as well as with the partial-occupancy solvent water mol­ecules.

Related literature

For the structures of some magnesium complexes, derived from phen­oxy­acetic acids, see: Smith et al. (1980[Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1980). J. Chem. Soc. Dalton Trans. pp. 2462-2466.], 1981[Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1981). Cryst. Struct. Commun. 10, 1397-1402.], 1982[Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1982). Inorg. Chim. Acta, 62, 241-246.]); Kennard et al. (1986[Kennard, C. H. L., O'Reilly, E. J., Schiller, S., Smith, G. & White, A. H. (1986). Aust. J. Chem. 39, 1823-1832.]). For the structures of other metal complexes with 4-fluoro­phen­oxy­acetate, see: O'Reilly et al. (1984[O'Reilly, E. J., Smith, G. & Kennard, C. H. L. (1984). Inorg. Chim. Acta, 90, 63-71.]); Smith et al. (1993[Smith, G., Lynch, D. E., Mak, T. C. W., Yip, W.-H. & Kennard, C. H. L. (1993). Polyhedron, 12, 203-208.]).

[Scheme 1]

Experimental

Crystal data
  • [Mg(C8H6FO3)2(H2O)2]·0.4H2O

  • Mr = 405.80

  • Monoclinic, P 21 /c

  • a = 17.2526 (9) Å

  • b = 6.8899 (3) Å

  • c = 7.5474 (3) Å

  • β = 95.118 (4)°

  • V = 893.57 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 200 K

  • 0.30 × 0.20 × 0.05 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.964, Tmax = 0.980

  • 5825 measured reflections

  • 1762 independent reflections

  • 1400 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.109

  • S = 1.06

  • 1762 reflections

  • 133 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Selected bond lengths (Å)

Mg1—O1W 2.1032 (14)
Mg1—O21 2.0478 (14)
Mg1—O22i 2.0620 (14)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H11W⋯O1iv 0.91 2.45 3.214 (2) 143
O1W—H12W⋯O22iv 0.92 2.38 3.0352 (19) 128
O1W—H12W⋯O21i 0.92 1.92 2.760 (2) 151
O2W—H21W⋯O1iv 0.95 2.41 3.034 (10) 123
O2W—H22W⋯O22iii 0.85 2.13 2.950 (9) 160
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Magnesium complexes involving monoanionic phenoxyacetate ligands (L) show a variety of coordination modes, all based on an octahedral MgO6 metal stereochemistry, e.g. discrete monomeric [[MgL2(H2O)4] (L = 2-fluorophenoxyacetate) (Kennard et al., 1986); (L = 4-chloro-2-methylphenoxyacetate) (Smith et al., 1981); [MgL(H2O)5] (L = 2,4,5-trichlorophenoxyacetate) (Smith et al., 1982)], or polymeric [[MgL2(H2O)2]n (L = phenoxyacetate or 4-chlorophenoxyacetate) (Smith et al., 1980)].

The title complex, [Mg(H2O)2(C8H6FO3)2]n (0.4H2O)n was obtained from the reaction of 4-fluorophenoxyacetic acid with MgCO3 in aqueous ethanol and the structure is reported herein. In this structure (Fig. 1), the slightly distorted octahedral MgO6 complex units [bond range Mg—O, 2.0478 (14)–2.1032 (14) Å (Table 1)] have crystallographic inversion symmetry, the coordination polyhedron comprising two trans-related water molecules and four carboxyl O-atom donors, two of which are bridging. Within the two-dimensional complex polymer layers which extend across (100), the coordinated water molecules from intermolecular O—H···O hydrogen-bonding interactions (Table 2), with carboxyl and phenoxy O-atom acceptors as well as with the partial water molecules of solvation (S.O.F. = 0.2) (Fig. 2). Except for the presence of the partial water molecules, the structure is similar to the those of the isomorphous Mg complexes with phenoxyacetate and 4-chlorophenoxyacetate (Smith et al., 1980). In the present complex, the 4-fluorophenoxyacetate ligand is essentially planar, with the carboxyl group rotated slightly out of the plane [benzene ring to acetate dihedral angle = 12.26 (12)°].

Related literature top

For the structures of some magnesium complexes with phenoxyacetic acids, see: Smith et al. (1980, 1981, 1982); Kennard et al. (1986). For the structures of other metal complexes with 4-fluorophenoxyacetate, see: O'Reilly et al. (1984); Smith et al. (1993).

Experimental top

The title compound was synthesized by the addition of excess MgCO3 to 15 ml of a hot aqueous ethanolic solution (10:1) of 4-fluorophenoxyacetic acid (0.1 g). After completion of the reaction, the excess MgCO3 was removed by filtration and the solution was allowed evaporate to incipient dryness at room temperature, giving thin colourless plates of the title compound from which a specimen was cleaved for the X-ray analysis.

Refinement top

Hydrogen atoms on the coordinated water molecule were located by difference methods and both positional and isotropic displacement parameters were initially refined but these were then allowed to ride, with Uiso(H) = 1.5Ueq(C). Other H-atoms were included in the refinement at calculated positions [C—H(aromatic) = 0.93 Å, 0.98 Å (methylene)] or O—H = 0.84–0.94 Å, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O), also using a riding-model approximation. The site occupancy factor for the partial water molecule of solvation was determined as 0.196 (4) and was subsequently fixed as 0.20.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, including the partial water molecules of solvation (O2W), with displacement ellipsoids drawn at the 50% probability level. For symmetry codes, see Table 1.
[Figure 2] Fig. 2. The hydrogen-bonding interactions, shown as dashed lines, in the title compound viewed along c. The partial water molecule of solvation and non-associative H-atoms have been omitted. For symmetry codes, see Tables 1 and 2.
Poly[[diaquabis[µ-2-(4-fluorophenoxy)acetato- κ2O1:O1']magnesium] 0.4-hydrate] top
Crystal data top
[Mg(C8H6FO3)2(H2O)2]·0.4H2OF(000) = 420
Mr = 405.80Dx = 1.508 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1476 reflections
a = 17.2526 (9) Åθ = 3.2–28.9°
b = 6.8899 (3) ŵ = 0.17 mm1
c = 7.5474 (3) ÅT = 200 K
β = 95.118 (4)°Plate, colourless
V = 893.57 (7) Å30.30 × 0.20 × 0.05 mm
Z = 2
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
1762 independent reflections
Radiation source: Enhance (Mo) X-ray source1400 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.2°
ω scansh = 2121
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 88
Tmin = 0.964, Tmax = 0.980l = 99
5825 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0424P)2 + 0.393P]
where P = (Fo2 + 2Fc2)/3
1762 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Mg(C8H6FO3)2(H2O)2]·0.4H2OV = 893.57 (7) Å3
Mr = 405.80Z = 2
Monoclinic, P21/cMo Kα radiation
a = 17.2526 (9) ŵ = 0.17 mm1
b = 6.8899 (3) ÅT = 200 K
c = 7.5474 (3) Å0.30 × 0.20 × 0.05 mm
β = 95.118 (4)°
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
1762 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
1400 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.980Rint = 0.040
5825 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.06Δρmax = 0.25 e Å3
1762 reflectionsΔρmin = 0.29 e Å3
133 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
xyzUiso*/UeqOcc. (<1)
Mg10.000000.500000.500000.0187 (3)
F40.49577 (8)0.0237 (3)0.7819 (2)0.0567 (6)
O10.20100 (10)0.0103 (3)0.4489 (2)0.0481 (6)
O1W0.09125 (8)0.6177 (2)0.36712 (19)0.0255 (5)
O210.01967 (8)0.2303 (2)0.39916 (19)0.0255 (4)
O220.07774 (8)0.02846 (19)0.22234 (18)0.0220 (4)
C10.27377 (13)0.0045 (4)0.5408 (3)0.0358 (8)
C20.32768 (15)0.1323 (4)0.4814 (4)0.0519 (10)
C30.40282 (15)0.1370 (4)0.5616 (4)0.0487 (9)
C40.42218 (13)0.0158 (4)0.7001 (3)0.0393 (8)
C50.37063 (15)0.1118 (4)0.7620 (3)0.0408 (9)
C60.29510 (14)0.1183 (4)0.6810 (3)0.0378 (8)
C110.14596 (12)0.1286 (3)0.4960 (3)0.0264 (7)
C210.07588 (12)0.1271 (3)0.3609 (3)0.0194 (6)
O2W0.2262 (5)0.5768 (14)0.5816 (12)0.048 (3)0.200
H20.313300.215400.387000.0620*
H30.439400.221600.521400.0580*
H50.385800.193300.857000.0490*
H60.259200.204900.721000.0450*
H11A0.169400.256600.500700.0320*
H11B0.129900.098600.612900.0320*
H11W0.132900.678300.424700.0380*
H12W0.066000.689800.277800.0380*
H21W0.227900.705400.628500.0710*0.200
H22W0.189900.525400.634500.0710*0.200
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mg10.0232 (5)0.0158 (5)0.0167 (5)0.0015 (4)0.0003 (4)0.0012 (4)
F40.0271 (7)0.0734 (12)0.0671 (11)0.0020 (8)0.0101 (7)0.0008 (9)
O10.0388 (10)0.0607 (12)0.0412 (11)0.0274 (9)0.0169 (8)0.0299 (9)
O1W0.0261 (8)0.0252 (8)0.0249 (8)0.0015 (7)0.0008 (6)0.0034 (6)
O210.0299 (8)0.0197 (7)0.0261 (8)0.0051 (7)0.0011 (6)0.0065 (6)
O220.0274 (8)0.0198 (7)0.0186 (7)0.0013 (6)0.0003 (6)0.0028 (6)
C10.0310 (12)0.0464 (15)0.0286 (13)0.0124 (12)0.0048 (10)0.0082 (11)
C20.0461 (16)0.0655 (19)0.0416 (16)0.0250 (15)0.0107 (13)0.0223 (14)
C30.0373 (15)0.0621 (18)0.0457 (16)0.0206 (14)0.0021 (12)0.0062 (14)
C40.0249 (12)0.0519 (16)0.0401 (15)0.0001 (12)0.0021 (11)0.0062 (13)
C50.0354 (14)0.0475 (16)0.0383 (15)0.0048 (12)0.0037 (11)0.0096 (12)
C60.0334 (13)0.0466 (15)0.0327 (13)0.0060 (12)0.0012 (11)0.0109 (12)
C110.0293 (12)0.0258 (11)0.0237 (11)0.0069 (10)0.0005 (9)0.0071 (9)
C210.0254 (11)0.0130 (9)0.0198 (10)0.0022 (9)0.0022 (8)0.0013 (8)
O2W0.045 (5)0.054 (6)0.043 (5)0.017 (5)0.001 (4)0.009 (4)
Geometric parameters (Å, º) top
Mg1—O1W2.1032 (14)O2W—H21W0.9500
Mg1—O212.0478 (14)C1—C21.384 (4)
Mg1—O22i2.0620 (14)C1—C61.379 (3)
Mg1—O1Wii2.1032 (14)C2—C31.381 (4)
Mg1—O21ii2.0478 (14)C3—C41.356 (4)
Mg1—O22iii2.0620 (14)C4—C51.363 (4)
F4—C41.362 (3)C5—C61.390 (3)
O1—C11.380 (3)C11—C211.511 (3)
O1—C111.416 (3)C2—H20.9300
O21—C211.257 (3)C3—H30.9300
O22—C211.250 (3)C5—H50.9300
O1W—H11W0.9100C6—H60.9300
O1W—H12W0.9200C11—H11B0.9700
O2W—H22W0.8500C11—H11A0.9700
O1W—Mg1—O2190.96 (5)C1—C2—C3120.3 (3)
O1W—Mg1—O22i92.03 (5)C2—C3—C4118.7 (2)
O1W—Mg1—O1Wii180.00F4—C4—C3118.7 (2)
O1W—Mg1—O21ii89.04 (5)F4—C4—C5118.7 (2)
O1W—Mg1—O22iii87.97 (5)C3—C4—C5122.6 (2)
O21—Mg1—O22i84.33 (5)C4—C5—C6119.0 (2)
O1Wii—Mg1—O2189.04 (5)C1—C6—C5119.6 (2)
O21—Mg1—O21ii180.00O1—C11—C21109.90 (17)
O21—Mg1—O22iii95.67 (5)O21—C21—C11115.38 (19)
O1Wii—Mg1—O22i87.97 (5)O22—C21—C11119.32 (18)
O21ii—Mg1—O22i95.67 (5)O21—C21—O22125.3 (2)
O22i—Mg1—O22iii180.00C3—C2—H2120.00
O1Wii—Mg1—O21ii90.96 (5)C1—C2—H2120.00
O1Wii—Mg1—O22iii92.03 (5)C2—C3—H3121.00
O21ii—Mg1—O22iii84.33 (5)C4—C3—H3121.00
C1—O1—C11117.06 (19)C4—C5—H5120.00
Mg1—O21—C21139.08 (14)C6—C5—H5121.00
Mg1iv—O22—C21132.00 (13)C5—C6—H6120.00
Mg1—O1W—H12W103.00C1—C6—H6120.00
H11W—O1W—H12W114.00O1—C11—H11A110.00
Mg1—O1W—H11W123.00O1—C11—H11B110.00
H21W—O2W—H22W102.00C21—C11—H11B110.00
O1—C1—C6124.9 (2)H11A—C11—H11B108.00
C2—C1—C6119.9 (2)C21—C11—H11A110.00
O1—C1—C2115.2 (2)
O1W—Mg1—O21—C2136.0 (2)C6—C1—C2—C30.2 (4)
O22i—Mg1—O21—C21127.9 (2)O1—C1—C6—C5179.4 (2)
O1Wii—Mg1—O21—C21144.0 (2)C2—C1—C6—C50.3 (4)
O22iii—Mg1—O21—C2152.1 (2)C1—C2—C3—C40.7 (4)
C11—O1—C1—C2175.1 (2)C2—C3—C4—F4178.5 (2)
C11—O1—C1—C64.0 (3)C2—C3—C4—C50.7 (4)
C1—O1—C11—C21169.15 (19)F4—C4—C5—C6179.0 (2)
Mg1—O21—C21—O22136.10 (18)C3—C4—C5—C60.2 (4)
Mg1—O21—C21—C1143.1 (3)C4—C5—C6—C10.3 (4)
Mg1iv—O22—C21—O214.0 (3)O1—C11—C21—O21172.84 (18)
Mg1iv—O22—C21—C11175.24 (13)O1—C11—C21—O227.9 (3)
O1—C1—C2—C3179.0 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1; (iii) x, y+1/2, z+1/2; (iv) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O1v0.912.453.214 (2)143
O1W—H12W···O22v0.922.383.0352 (19)128
O1W—H12W···O21i0.921.922.760 (2)151
O2W—H21W···O1v0.952.413.034 (10)123
O2W—H22W···O22iii0.852.132.950 (9)160
Symmetry codes: (i) x, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Mg(C8H6FO3)2(H2O)2]·0.4H2O
Mr405.80
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)17.2526 (9), 6.8899 (3), 7.5474 (3)
β (°) 95.118 (4)
V3)893.57 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.30 × 0.20 × 0.05
Data collection
DiffractometerOxford Diffraction Gemini-S CCD-detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.964, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
5825, 1762, 1400
Rint0.040
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.109, 1.06
No. of reflections1762
No. of parameters133
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.29

Computer programs: CrysAlis PRO (Agilent, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Selected bond lengths (Å) top
Mg1—O1W2.1032 (14)Mg1—O1Wii2.1032 (14)
Mg1—O212.0478 (14)Mg1—O21ii2.0478 (14)
Mg1—O22i2.0620 (14)Mg1—O22iii2.0620 (14)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1; (iii) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O1iv0.912.453.214 (2)143
O1W—H12W···O22iv0.922.383.0352 (19)128
O1W—H12W···O21i0.921.922.760 (2)151
O2W—H21W···O1iv0.952.413.034 (10)123
O2W—H22W···O22iii0.852.132.950 (9)160
Symmetry codes: (i) x, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+1, z.
 

Acknowledgements

The author acknowledges financial support from the Australian Research Council, the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

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