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Bis(di-2-pyridylmethane­diol-κ3N,O,N′)copper(II) bis­­(tetra­fluorido­borate) dihydrate

aDepartment of Chemistry and Biochemistry, Central Connecticut State University, New Britain, CT 06050, USA
*Correspondence e-mail: westcottb@ccsu.edu

(Received 7 April 2009; accepted 5 May 2009; online 14 May 2009)

The title complex, [Cu(C11H10N2O2)2](BF4)2·2H2O, was isolated as a dihydrate from a 1:2 molar mixture of copper(II) tetra­fluoridoborate hexa­hydrate with di-2-pyridyl ketone in aqueous solution. The centrosymmetric complex cation is structurally similar to that found in previously reported salts and exhibits Cu—O bonds deviating by 25 degrees from an octa­hedral geometry by the so-called `off-axis angle' distortion. The BF4 anion exhibits a two site disorder of the fluorine atoms [ratio 0.210 (8):0.790 (8)].

Related literature

For related structures, see: Wang et al. (1986[Wang, S. L., Richardson, J. W., Briggs, S. J. & Jacobson, R. A. (1986). Inorg. Chim. Acta, 111, 67-68.]); Tangoulis et al. (1997[Tangoulis, V., Raptopoulou, C. P., Terzis, A., Paschalidou, S., Perlepes, S. P. & Bakalbassis, E. G. (1997). Inorg. Chem. 36, 3996-4006.]); Yang et al. (1998[Yang, G., Tong, M.-L., Chen, X.-M. & Ng, S. W. (1998). Acta Cryst. C54, 732-734.]); Tong et al. (1998[Tong, M.-L., Yang, G., Chen, X.-M. & Ng, S. W. (1998). Acta Cryst. C54, 217-219.]); Serna et al. (1999[Serna, Z., Barandika, M. G., Cortés, R., Urtiaga, M. K. & Arriortua, M. I. (1999). Polyhedron, 18, 249-255.]); Reinoso et al. (2003[Reinoso, S., Vitoria, P., San Felices, L., Lezama, L. & Gutiérrez-Zorrilla, J. M. (2003). Acta Cryst. E59, m548-m550.]); Li et al. (2005[Li, C.-J., Li, W., Tong, M.-L. & Ng, S. W. (2005). Acta Cryst. E61, m232-m234.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C11H10N2O2)2](BF4)2·2H2O

  • Mr = 677.61

  • Monoclinic, P 21 /c

  • a = 7.8147 (2) Å

  • b = 14.4225 (4) Å

  • c = 12.1840 (3) Å

  • β = 101.160 (3)°

  • V = 1347.26 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.91 mm−1

  • T = 293 K

  • 0.8 × 0.6 × 0.6 mm

Data collection
  • Oxford Diffraction Sapphire CCD diffractometer

  • Absorption correction: multi-scan SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]) Tmin = 0.474, Tmax = 0.579

  • 25175 measured reflections

  • 5349 independent reflections

  • 4145 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.192

  • S = 1.21

  • 5349 reflections

  • 219 parameters

  • 10 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.72 e Å−3

  • Δρmin = −1.03 e Å−3

Table 1
Selected geometric parameters (Å, °)

Cu1—N1i 2.0099 (19)
Cu1—N1 2.0099 (19)
Cu1—N2 2.0146 (19)
Cu1—N2i 2.0147 (19)
Cu1—O1 2.4312 (17)
Cu1—O1i 2.4312 (17)
Symmetry code: (i) -x, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3 0.82 1.87 2.686 (3) 172
Symmetry codes: .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Related literature top

For related structures, see: Wang et al. (1986); Tangoulis et al. (1997); Yang et al. (1998); Tong et al. (1998); Serna et al. (1999); Reinoso et al. (2003); Li et al. (2005).

Experimental top

All chemicals and reagents were purchased from Aldrich and used as received. di-2-pyridyl ketone (2 mmol) and copper(II) tetrafluorborate hexahydrate (1 mmol) were combined in 40 ml of water and stirred for 30 minutes. The resulting violet crystals were isolated after 48 h by slow evaporation of the solution.

Refinement top

For structure solution, direct methods were used to locate the initial structural model that consisted of all non-hydrogen atoms. All ligand-based H atoms were added during the refinement stage at idealized positions. Water-based H atoms were found during subsequent cycles from difference maps and their bond lengths to oxygen were free to refine. All H atoms were refined isotropically and all non-hydrogen atoms were refined anisotropically.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXLTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP representation of the title complex. Thermal ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.
Bis(di-2-pyridylmethanediol-κ3N,O,N')copper(II) bis(tetrafluoroidborate) dihydrate top
Crystal data top
[Cu(C11H10N2O2)2](BF4)2·2H2OF(000) = 686
Mr = 677.61Dx = 1.670 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5349 reflections
a = 7.8147 (2) Åθ = 3.8–32.0°
b = 14.4225 (4) ŵ = 0.91 mm1
c = 12.1840 (3) ÅT = 293 K
β = 101.160 (3)°Parallelpiped, violet
V = 1347.26 (6) Å30.8 × 0.6 × 0.6 mm
Z = 2
Data collection top
Oxford Diffraction Sapphire CCD
diffractometer
5349 independent reflections
Radiation source: fine-focus sealed tube4145 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 34.7°, θmin = 3.9°
Absorption correction: multi-scan
SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006)
h = 1211
Tmin = 0.474, Tmax = 0.579k = 2222
25175 measured reflectionsl = 1819
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.21 w = 1/[σ^2^(Fo^2^) + (0.0959P)^2^ + 1.P]
where P = (Fo^2^ + 2Fc^2^)/3
5349 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.72 e Å3
10 restraintsΔρmin = 1.03 e Å3
Crystal data top
[Cu(C11H10N2O2)2](BF4)2·2H2OV = 1347.26 (6) Å3
Mr = 677.61Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.8147 (2) ŵ = 0.91 mm1
b = 14.4225 (4) ÅT = 293 K
c = 12.1840 (3) Å0.8 × 0.6 × 0.6 mm
β = 101.160 (3)°
Data collection top
Oxford Diffraction Sapphire CCD
diffractometer
5349 independent reflections
Absorption correction: multi-scan
SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006)
4145 reflections with I > 2σ(I)
Tmin = 0.474, Tmax = 0.579Rint = 0.036
25175 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05510 restraints
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.21Δρmax = 0.72 e Å3
5349 reflectionsΔρmin = 1.03 e Å3
219 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. Hydrogen atoms were included in calculated positions for the ring carbons on the dpk ligand (0.93Å for sp2 carbons) and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom for sp2 carbons. Oxygen hydrogens were found in difference maps.

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)
Cu10.00000.00000.50000.02185 (12)
C10.2975 (3)0.04790 (18)0.3891 (2)0.0289 (5)
H10.25140.00350.33630.035*
C20.4472 (4)0.0936 (2)0.3777 (2)0.0335 (5)
H2A0.50010.08100.31720.040*
C30.5190 (4)0.1586 (2)0.4571 (2)0.0348 (5)
H30.62170.18940.45170.042*
C40.4334 (3)0.17694 (18)0.5455 (2)0.0310 (5)
H40.47800.22030.60010.037*
C50.2824 (3)0.12975 (15)0.55022 (18)0.0243 (4)
C60.1798 (3)0.14291 (15)0.64412 (18)0.0240 (4)
C70.1983 (3)0.05478 (15)0.71483 (18)0.0228 (4)
C80.2869 (4)0.05111 (17)0.8236 (2)0.0294 (5)
H80.34110.10360.85870.035*
C90.2936 (4)0.03360 (19)0.8802 (2)0.0322 (5)
H90.35110.03830.95430.039*
C100.2138 (4)0.11005 (17)0.8244 (2)0.0289 (4)
H100.21760.16710.86040.035*
C110.1283 (3)0.10113 (16)0.71447 (19)0.0250 (4)
H110.07460.15290.67720.030*
N10.2158 (3)0.06543 (13)0.47416 (15)0.0230 (3)
N20.1204 (3)0.02000 (13)0.65999 (15)0.0214 (3)
O10.0028 (2)0.15157 (12)0.58765 (14)0.0252 (3)
O20.2355 (3)0.21705 (12)0.71285 (15)0.0310 (4)
H20.22140.26510.67630.047*
H500.064 (5)0.153 (3)0.633 (3)0.034 (9)*
H510.181 (7)0.416 (4)0.599 (4)0.058 (13)*
H520.133 (6)0.354 (3)0.529 (4)0.044 (11)*
O30.2110 (4)0.36785 (16)0.5814 (2)0.0419 (5)
B10.8127 (4)0.13674 (19)0.8480 (2)0.0302 (5)0.790 (8)
F10.7868 (2)0.16783 (13)0.73741 (13)0.0381 (4)0.790 (8)
F20.8638 (9)0.0451 (3)0.8536 (8)0.0471 (13)0.790 (8)
F30.9557 (7)0.1892 (2)0.9056 (3)0.0674 (14)0.790 (8)
F40.6729 (5)0.1531 (3)0.8951 (3)0.0661 (12)0.790 (8)
B1B0.8127 (4)0.13674 (19)0.8480 (2)0.0302 (5)0.210 (8)
F1B0.7868 (2)0.16783 (13)0.73741 (13)0.0381 (4)0.210 (8)
F2B0.894 (4)0.0519 (14)0.854 (3)0.0471 (13)0.210 (8)
F3B0.866 (3)0.1927 (9)0.9307 (11)0.0674 (14)0.210 (8)
F4B0.6394 (16)0.1147 (11)0.8558 (12)0.0661 (12)0.210 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0261 (2)0.02088 (19)0.01787 (18)0.00313 (13)0.00248 (13)0.00088 (12)
C10.0302 (11)0.0331 (12)0.0238 (10)0.0027 (9)0.0066 (8)0.0000 (8)
C20.0302 (12)0.0398 (14)0.0323 (12)0.0002 (10)0.0109 (9)0.0049 (10)
C30.0271 (12)0.0358 (13)0.0423 (14)0.0049 (9)0.0088 (10)0.0050 (11)
C40.0308 (12)0.0257 (10)0.0350 (12)0.0068 (9)0.0024 (9)0.0008 (9)
C50.0271 (10)0.0209 (9)0.0234 (9)0.0013 (7)0.0016 (7)0.0019 (7)
C60.0313 (11)0.0184 (8)0.0210 (9)0.0036 (7)0.0016 (7)0.0010 (7)
C70.0248 (10)0.0206 (9)0.0223 (9)0.0026 (7)0.0030 (7)0.0012 (7)
C80.0352 (12)0.0263 (10)0.0246 (10)0.0040 (9)0.0006 (8)0.0005 (8)
C90.0397 (13)0.0323 (12)0.0222 (10)0.0016 (10)0.0004 (9)0.0025 (9)
C100.0351 (12)0.0249 (10)0.0259 (10)0.0006 (9)0.0037 (9)0.0046 (8)
C110.0259 (10)0.0206 (9)0.0285 (10)0.0024 (7)0.0053 (8)0.0008 (7)
N10.0239 (8)0.0236 (8)0.0213 (8)0.0030 (6)0.0036 (6)0.0005 (6)
N20.0241 (8)0.0198 (7)0.0201 (7)0.0016 (6)0.0035 (6)0.0003 (6)
O10.0270 (8)0.0252 (7)0.0227 (7)0.0009 (6)0.0026 (6)0.0011 (6)
O20.0455 (11)0.0198 (7)0.0257 (8)0.0050 (7)0.0019 (7)0.0033 (6)
O30.0584 (14)0.0259 (9)0.0390 (11)0.0041 (9)0.0035 (10)0.0029 (8)
B10.0412 (15)0.0245 (11)0.0250 (11)0.0042 (10)0.0064 (10)0.0002 (9)
F10.0457 (10)0.0417 (9)0.0268 (7)0.0064 (7)0.0072 (6)0.0068 (6)
F20.069 (3)0.0238 (11)0.0477 (10)0.0088 (16)0.010 (2)0.0005 (10)
F30.094 (3)0.0412 (13)0.0503 (17)0.0201 (19)0.0284 (19)0.0030 (12)
F40.084 (2)0.072 (3)0.054 (2)0.0369 (19)0.0436 (18)0.0173 (17)
B1B0.0412 (15)0.0245 (11)0.0250 (11)0.0042 (10)0.0064 (10)0.0002 (9)
F1B0.0457 (10)0.0417 (9)0.0268 (7)0.0064 (7)0.0072 (6)0.0068 (6)
F2B0.069 (3)0.0238 (11)0.0477 (10)0.0088 (16)0.010 (2)0.0005 (10)
F3B0.094 (3)0.0412 (13)0.0503 (17)0.0201 (19)0.0284 (19)0.0030 (12)
F4B0.084 (2)0.072 (3)0.054 (2)0.0369 (19)0.0436 (18)0.0173 (17)
Geometric parameters (Å, º) top
Cu1—N1i2.0099 (19)C6—C71.527 (3)
Cu1—N12.0099 (19)C7—N21.350 (3)
Cu1—N22.0146 (19)C7—C81.372 (3)
Cu1—N2i2.0147 (19)C8—C91.399 (4)
Cu1—O12.4312 (17)C8—H80.9300
Cu1—O1i2.4312 (17)C9—C101.379 (4)
C1—N11.343 (3)C9—H90.9300
C1—C21.373 (4)C10—C111.382 (3)
C1—H10.9300C10—H100.9300
C2—C31.385 (4)C11—N21.341 (3)
C2—H2A0.9300C11—H110.9300
C3—C41.399 (4)O1—H500.83 (4)
C3—H30.9300O2—H20.8200
C4—C51.373 (3)O3—H510.78 (5)
C4—H40.9300O3—H520.82 (5)
C5—N11.343 (3)B1—F41.350 (4)
C5—C61.531 (3)B1—F21.378 (5)
C6—O21.376 (3)B1—F11.397 (3)
C6—O11.427 (3)B1—F31.417 (5)
N1i—Cu1—N1179.999 (1)O1—C6—C5104.48 (17)
N1i—Cu1—N291.74 (8)C7—C6—C5108.21 (18)
N1—Cu1—N288.27 (8)N2—C7—C8122.8 (2)
N1i—Cu1—N2i88.26 (8)N2—C7—C6113.67 (19)
N1—Cu1—N2i91.73 (8)C8—C7—C6123.5 (2)
N2—Cu1—N2i180.0C7—C8—C9118.3 (2)
N1i—Cu1—O1106.84 (7)C7—C8—H8120.9
N1—Cu1—O173.16 (7)C9—C8—H8120.9
N2—Cu1—O174.99 (7)C10—C9—C8119.0 (2)
N2i—Cu1—O1105.01 (7)C10—C9—H9120.5
N1i—Cu1—O1i73.16 (7)C8—C9—H9120.5
N1—Cu1—O1i106.84 (7)C11—C10—C9119.4 (2)
N2—Cu1—O1i105.01 (7)C11—C10—H10120.3
N2i—Cu1—O1i74.99 (7)C9—C10—H10120.3
O1—Cu1—O1i180.00 (8)N2—C11—C10121.9 (2)
N1—C1—C2122.0 (2)N2—C11—H11119.1
N1—C1—H1119.0C10—C11—H11119.1
C2—C1—H1119.0C5—N1—C1118.9 (2)
C1—C2—C3119.5 (2)C5—N1—Cu1116.18 (15)
C1—C2—H2A120.2C1—N1—Cu1124.86 (16)
C3—C2—H2A120.2C11—N2—C7118.63 (19)
C2—C3—C4118.4 (2)C11—N2—Cu1124.89 (15)
C2—C3—H3120.8C7—N2—Cu1116.48 (15)
C4—C3—H3120.8C6—O1—Cu193.35 (12)
C5—C4—C3118.8 (2)C6—O1—H50111 (3)
C5—C4—H4120.6Cu1—O1—H50111 (3)
C3—C4—H4120.6C6—O2—H2109.5
N1—C5—C4122.3 (2)H51—O3—H52103 (5)
N1—C5—C6114.34 (19)F4—B1—F2113.4 (4)
C4—C5—C6123.3 (2)F4—B1—F1112.1 (3)
O2—C6—O1112.86 (19)F2—B1—F1110.0 (4)
O2—C6—C7108.62 (18)F4—B1—F3108.8 (3)
O1—C6—C7108.78 (18)F2—B1—F3107.1 (4)
O2—C6—C5113.67 (19)F1—B1—F3105.0 (3)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.821.872.686 (3)172

Experimental details

Crystal data
Chemical formula[Cu(C11H10N2O2)2](BF4)2·2H2O
Mr677.61
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.8147 (2), 14.4225 (4), 12.1840 (3)
β (°) 101.160 (3)
V3)1347.26 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.91
Crystal size (mm)0.8 × 0.6 × 0.6
Data collection
DiffractometerOxford Diffraction Sapphire CCD
diffractometer
Absorption correctionMulti-scan
SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006)
Tmin, Tmax0.474, 0.579
No. of measured, independent and
observed [I > 2σ(I)] reflections
25175, 5349, 4145
Rint0.036
(sin θ/λ)max1)0.801
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.192, 1.21
No. of reflections5349
No. of parameters219
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.72, 1.03

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXLTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Cu1—N1i2.0099 (19)Cu1—N2i2.0147 (19)
Cu1—N12.0099 (19)Cu1—O12.4312 (17)
Cu1—N22.0146 (19)Cu1—O1i2.4312 (17)
N1i—Cu1—N1179.999 (1)N2—Cu1—O174.99 (7)
N1i—Cu1—N291.74 (8)N2i—Cu1—O1105.01 (7)
N1—Cu1—N288.27 (8)N1i—Cu1—O1i73.16 (7)
N1i—Cu1—N2i88.26 (8)N1—Cu1—O1i106.84 (7)
N1—Cu1—N2i91.73 (8)N2—Cu1—O1i105.01 (7)
N2—Cu1—N2i180.0N2i—Cu1—O1i74.99 (7)
N1i—Cu1—O1106.84 (7)O1—Cu1—O1i180.00 (8)
N1—Cu1—O173.16 (7)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.821.872.686 (3)172.0
 

Acknowledgements

The diffractometer was purchased with funding from the National Science Foundation (NSF # 0420322). Additional funding is from a CSUAAUP research grant.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationLi, C.-J., Li, W., Tong, M.-L. & Ng, S. W. (2005). Acta Cryst. E61, m232–m234.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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