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

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Di­chloridobis(1,10-phenanthroline-5,6-dione-κ2N,N′)mercury(II)

aDepartamento de Química Inorgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68563, 21941-909 Rio de Janeiro, RJ, Brazil, bDepartment of Chemistry, University of Aberdeen, Old Aberdeen, AB15 5NY, Scotland, cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dDepartamento de Quimica, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 10 November 2009; accepted 18 November 2009; online 21 November 2009)

In the title compound, [HgCl2(C12H6N2O2)2], the HgII atom is located on a twofold rotation axis and exists within a distorted octa­hedral geometry defined by a cis-Cl2N4 donor set. Mol­ecules are connected into layers in the ac plane via extensive C—H⋯Cl contacts as each Cl atom forms two such inter­actions. Contacts between the layers are of the type C=O⋯π [O⋯centroid distance = 3.110 (8) Å].

Related literature

For related main-group compounds of 1,10-phenanthroline-5,6-dione, see: de Alencastro et al. (2005[Alencastro, R. B. de, Bomfim, J. A. S., Filgueiras, C. A. L., Howie, R. A. & Wardell, J. L. (2005). Appl. Organomet. Chem. 19, 479-487.]). For the ligand synthesis, see: Yamada et al. (1992[Yamada, M., Tanaka, Y., Yashimoto, Y., Juroda, S. & Shimao, I. (1992). Bull. Chem. Soc. Jpn, 65, 1006-1011.]). For a related structure, see: Ramezanipour et al. (2005[Ramezanipour, F., Aghabozorg, H. & Soleimannejad, J. (2005). Acta Cryst. E61, m1194-m1196.]).

[Scheme 1]

Experimental

Crystal data
  • [HgCl2(C12H6N2O2)2]

  • Mr = 691.87

  • Orthorhombic, F d d 2

  • a = 8.2261 (2) Å

  • b = 42.6761 (11) Å

  • c = 12.6108 (3) Å

  • V = 4427.12 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 7.24 mm−1

  • T = 120 K

  • 0.20 × 0.10 × 0.06 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.204, Tmax = 0.651

  • 10751 measured reflections

  • 2487 independent reflections

  • 2239 reflections with I > 2σ(I)

  • Rint = 0.075

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.094

  • S = 1.05

  • 2487 reflections

  • 159 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 2.27 e Å−3

  • Δρmin = −0.68 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1163 Friedel pairs

  • Flack parameter: −0.012 (13)

Table 1
Selected bond lengths (Å)

Hg—N1 2.439 (7)
Hg—N2 2.512 (6)
Hg—Cl1 2.5270 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯Cl1i 0.95 2.69 3.578 (8) 156
C9—H9⋯Cl1ii 0.95 2.78 3.701 (8) 164
Symmetry codes: (i) x-1, y, z; (ii) [x+{\script{1\over 2}}, y, z-{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

In continuation of the previous studies of coordination compounds of 1,10-phenanthroline-5,6-dione (pdon) ligand (de Alencastro et al., 2005), the title compound, HgCl2(pdon)2, was investigated. The reaction of HgCl2 with pdon (1:1 mol ratio) led to the isolation of a pure 1:1 complex, HgCl2(pdon). However, as the product was unsuitable for X-ray crystallography, a further recrystallization from MeNO2 solution was attempted, which led to the isolation of the title compound, a 1:2 complex. Of interest was that the 1:1 HgI2(pdon) complex, prepared similarly to the chloride analogue, was recovered on recrystallization from MeNO2. Unfortunately this set of crystals also proved unsuitable for X-ray crystallography.

In the title compound, the HgII atom lies on a crystallographic twofold axis and exists within a cis-Cl2N4 donor set defined by two Cl atoms and four N atoms derived from two chelating pdon ligands (Fig. 1). There is a small disparity in the magnitude of the Hg—N bond distances, with Hg—N1 of 2.439 (7) Å being shorter than Hg—N2 of 2.512 (6) Å. Distortions from an ideal octahedral geometry are related in part to the acute chelate angle of 66.9 (2)°. The pdon ligand is essentially planar with a RMS of 0.226 Å for the N and C atoms, with O1 and O2 atoms lying, respectively, -0.079 (12) and 0.071 (13) Å out of the least-squares plane. The dihedral angle formed between the symmetry related 1,10-phenanthroline planes is 87.13 (11)°. The structural features described herein for the title compound resemble those found for HgCl2(1,10-phenanthroline)2 (Ramezanipour et al., 2005).

In the crystal structure, C—H···Cl interactions are found so that each Cl atom is associated with two H atoms to form supramolecular arrays in the ac plane (Table 1 and Fig. 2). The most prominent interactions between the layers are of the type CO···π. The closest of these involves the carbonyl-O1 group and the centroid (Cg) of C4–C7, C11, C12 ring [O1···Cgi = 3.110 (8) Å with the C5–O1···Cgi angle being 133.1 (8)°, symmetry code: (i) -1/4+x, 1/4-y, -1/4+z] (Fig. 3).

Related literature top

For related main-group compounds of 1,10-phenanthroline-5,6-dione, see: de Alencastro et al. (2005). For the ligand synthesis, see: Yamada et al. (1992). For a related structure, see: Ramezanipour et al. (2005).

Experimental top

Solutions of HgCl2 (0.272 mg, 1.0 mmol) in EtOH (5 ml) and of 1,10-phenanthroline-5,6-dione (Yamada et al., 1992) (0.212 mg, 1.0 mmol) in EtOH (20 ml) were mixed and stirred at room temperature for 1 h. The precipitate was collected, washed with small portions of EtOH and petroleum ether and dried (yield 0.330 mg). Analysis, calculated for C12H6Cl2HgN2O2 [HgCl2(pdon)]: C 29.9, H 1.3, N 5.8%; found: C 30.2, H 1.5, N 5.2%.

Recrystallization of HgCl2(pdon) from MeNO2 solution produced crystals of the title compound, HgCl2(pdon)2.

Refinement top

H atoms were geometrically placed with C—H = 0.95 Å, and refined as riding with Uiso(H) = 1.2Ueq(C). The maximum and minimum residual electron density peaks of 2.27 and 0.68 e Å-3 were located 0.91 and 0.82 Å from Hg atom, respectively.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) -x, -y, z.]
[Figure 2] Fig. 2. Supramolecular array in the ac plane mediated by C—H···Cl contacts (orange dashed lines). [Colour codes: Hg orange; Cl cyan; O red; N blue; C grey; H green.]
[Figure 3] Fig. 3. Unit-cell contents viewed in projection down the a axis. The C—H···Cl contacts are shown as orange dashed lines. [Colour codes: Hg orange; Cl cyan; O red; N blue; C grey; H green.]
Dichloridobis(1,10-phenanthroline-5,6-dione-κ2N,N')mercury(II) top
Crystal data top
[HgCl2(C12H6N2O2)2]F(000) = 2640
Mr = 691.87Dx = 2.076 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 18660 reflections
a = 8.2261 (2) Åθ = 2.9–27.5°
b = 42.6761 (11) ŵ = 7.24 mm1
c = 12.6108 (3) ÅT = 120 K
V = 4427.12 (19) Å3Block, yellow
Z = 80.20 × 0.10 × 0.06 mm
Data collection top
Nonius KappaCCD
diffractometer
2487 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2239 reflections with I > 2σ(I)
10 cm confocal mirrors monochromatorRint = 0.075
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ and ω scansh = 108
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 5555
Tmin = 0.204, Tmax = 0.651l = 1616
10751 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0564P)2 + 3.1352P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2487 reflectionsΔρmax = 2.27 e Å3
159 parametersΔρmin = 0.68 e Å3
1 restraintAbsolute structure: Flack (1983), 1163 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.012 (13)
Crystal data top
[HgCl2(C12H6N2O2)2]V = 4427.12 (19) Å3
Mr = 691.87Z = 8
Orthorhombic, Fdd2Mo Kα radiation
a = 8.2261 (2) ŵ = 7.24 mm1
b = 42.6761 (11) ÅT = 120 K
c = 12.6108 (3) Å0.20 × 0.10 × 0.06 mm
Data collection top
Nonius KappaCCD
diffractometer
2487 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2239 reflections with I > 2σ(I)
Tmin = 0.204, Tmax = 0.651Rint = 0.075
10751 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.094Δρmax = 2.27 e Å3
S = 1.05Δρmin = 0.68 e Å3
2487 reflectionsAbsolute structure: Flack (1983), 1163 Friedel pairs
159 parametersAbsolute structure parameter: 0.012 (13)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Hg0.00000.00000.48512 (8)0.04052 (12)
Cl10.1811 (2)0.03035 (5)0.61020 (15)0.0486 (4)
O10.3649 (8)0.12440 (15)0.2228 (6)0.072 (2)
O20.0592 (10)0.12581 (18)0.1361 (7)0.081 (2)
N10.2157 (8)0.03565 (16)0.4299 (5)0.0406 (14)
N20.0815 (7)0.03486 (14)0.3337 (4)0.0399 (13)
C10.3618 (9)0.03505 (19)0.4754 (6)0.0472 (16)
H10.38400.01910.52580.057*
C20.4837 (9)0.0567 (2)0.4528 (7)0.050 (2)
H20.58690.05540.48640.060*
C30.4507 (11)0.07993 (18)0.3806 (6)0.0459 (17)
H30.53000.09550.36530.055*
C40.3014 (10)0.08061 (18)0.3300 (6)0.0435 (16)
C50.2664 (10)0.1051 (2)0.2493 (14)0.057 (3)
C60.0923 (11)0.1052 (2)0.1979 (8)0.059 (2)
C70.0217 (9)0.0800 (2)0.2297 (7)0.0450 (17)
C80.1742 (11)0.0790 (2)0.1830 (6)0.0482 (18)
H80.20710.09450.13350.058*
C90.2777 (9)0.0545 (2)0.2110 (6)0.0453 (18)
H90.38180.05260.17920.054*
C100.2257 (10)0.03325 (19)0.2861 (7)0.0437 (17)
H100.29650.01660.30470.052*
C110.0196 (9)0.05763 (18)0.3047 (6)0.0409 (16)
C120.1850 (9)0.05809 (16)0.3578 (7)0.0413 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg0.03662 (19)0.04817 (18)0.03677 (16)0.00021 (19)0.0000.000
Cl10.0400 (9)0.0635 (11)0.0424 (9)0.0042 (8)0.0003 (8)0.0077 (8)
O10.062 (4)0.064 (4)0.091 (5)0.015 (3)0.005 (4)0.029 (4)
O20.055 (4)0.082 (5)0.106 (6)0.016 (4)0.016 (4)0.049 (4)
N10.042 (3)0.046 (3)0.034 (3)0.003 (3)0.004 (2)0.003 (3)
N20.035 (3)0.049 (3)0.036 (3)0.003 (3)0.000 (2)0.001 (2)
C10.039 (4)0.064 (4)0.039 (3)0.007 (3)0.002 (3)0.005 (4)
C20.033 (4)0.069 (5)0.047 (4)0.006 (3)0.001 (3)0.010 (3)
C30.044 (4)0.047 (4)0.047 (4)0.006 (3)0.004 (3)0.011 (3)
C40.032 (3)0.053 (4)0.045 (4)0.001 (3)0.006 (3)0.004 (3)
C50.048 (5)0.055 (4)0.067 (10)0.002 (4)0.011 (5)0.012 (5)
C60.052 (5)0.059 (5)0.067 (5)0.000 (4)0.008 (4)0.012 (4)
C70.044 (4)0.048 (4)0.043 (4)0.003 (3)0.004 (3)0.001 (3)
C80.050 (5)0.052 (4)0.043 (4)0.004 (3)0.001 (3)0.007 (3)
C90.037 (4)0.062 (5)0.038 (4)0.011 (3)0.001 (3)0.007 (3)
C100.047 (5)0.042 (4)0.042 (4)0.005 (3)0.007 (3)0.001 (3)
C110.043 (4)0.042 (4)0.038 (3)0.000 (3)0.002 (3)0.009 (3)
C120.039 (4)0.040 (3)0.045 (3)0.000 (3)0.009 (3)0.002 (3)
Geometric parameters (Å, º) top
Hg—N12.439 (7)C3—H30.9500
Hg—N22.512 (6)C4—C121.401 (11)
Hg—Cl12.5270 (19)C4—C51.487 (15)
O1—C51.203 (11)C5—C61.572 (14)
O2—C61.206 (11)C6—C71.483 (12)
N1—C11.332 (10)C7—C111.386 (12)
N1—C121.344 (10)C7—C81.387 (12)
N2—C111.330 (10)C8—C91.392 (12)
N2—C101.331 (10)C8—H80.9500
C1—C21.393 (12)C9—C101.380 (11)
C1—H10.9500C9—H90.9500
C2—C31.374 (13)C10—H100.9500
C2—H20.9500C11—C121.516 (11)
C3—C41.384 (11)
N1—Hg—N1i146.8 (3)C4—C3—H3120.1
N1—Hg—N2i87.6 (2)C3—C4—C12118.4 (8)
N1i—Hg—N2i66.9 (2)C3—C4—C5120.1 (7)
N1—Hg—N266.9 (2)C12—C4—C5121.4 (7)
N1i—Hg—N287.6 (2)O1—C5—C4122.8 (9)
N2i—Hg—N281.0 (3)O1—C5—C6119.8 (11)
N1—Hg—Cl1106.71 (16)C4—C5—C6117.4 (8)
N1i—Hg—Cl193.95 (16)O2—C6—C7124.1 (9)
N2i—Hg—Cl1159.31 (13)O2—C6—C5118.3 (9)
N2—Hg—Cl190.78 (14)C7—C6—C5117.5 (8)
N1—Hg—Cl1i93.95 (16)C11—C7—C8119.4 (8)
N1i—Hg—Cl1i106.71 (16)C11—C7—C6122.0 (7)
N2i—Hg—Cl1i90.78 (14)C8—C7—C6118.6 (8)
N2—Hg—Cl1i159.31 (13)C7—C8—C9117.9 (8)
Cl1—Hg—Cl1i102.75 (10)C7—C8—H8121.0
C1—N1—C12118.3 (7)C9—C8—H8121.0
C1—N1—Hg121.4 (5)C10—C9—C8118.6 (7)
C12—N1—Hg120.0 (5)C10—C9—H9120.7
C11—N2—C10118.1 (7)C8—C9—H9120.7
C11—N2—Hg118.3 (5)N2—C10—C9123.5 (7)
C10—N2—Hg123.4 (5)N2—C10—H10118.3
N1—C1—C2123.3 (8)C9—C10—H10118.3
N1—C1—H1118.4N2—C11—C7122.5 (7)
C2—C1—H1118.4N2—C11—C12116.7 (7)
C3—C2—C1118.2 (7)C7—C11—C12120.8 (7)
C3—C2—H2120.9N1—C12—C4122.0 (8)
C1—C2—H2120.9N1—C12—C11117.3 (7)
C2—C3—C4119.8 (7)C4—C12—C11120.7 (7)
C2—C3—H3120.1
N1i—Hg—N1—C1135.2 (6)C4—C5—C6—C72.9 (16)
N2i—Hg—N1—C196.6 (6)O2—C6—C7—C11177.0 (10)
N2—Hg—N1—C1177.8 (6)C5—C6—C7—C112.3 (14)
Cl1—Hg—N1—C198.6 (6)O2—C6—C7—C82.6 (15)
Cl1i—Hg—N1—C15.9 (6)C5—C6—C7—C8178.0 (9)
N1i—Hg—N1—C1250.0 (5)C11—C7—C8—C92.5 (12)
N2i—Hg—N1—C1288.6 (6)C6—C7—C8—C9177.8 (8)
N2—Hg—N1—C127.4 (5)C7—C8—C9—C102.2 (12)
Cl1—Hg—N1—C1276.2 (6)C11—N2—C10—C92.3 (12)
Cl1i—Hg—N1—C12179.2 (5)Hg—N2—C10—C9172.5 (6)
N1—Hg—N2—C117.4 (5)C8—C9—C10—N20.2 (12)
N1i—Hg—N2—C11165.7 (5)C10—N2—C11—C71.9 (11)
N2i—Hg—N2—C1198.7 (5)Hg—N2—C11—C7173.2 (6)
Cl1—Hg—N2—C11100.4 (5)C10—N2—C11—C12177.9 (7)
Cl1i—Hg—N2—C1130.9 (8)Hg—N2—C11—C127.0 (8)
N1—Hg—N2—C10177.7 (6)C8—C7—C11—N20.5 (12)
N1i—Hg—N2—C1019.5 (6)C6—C7—C11—N2179.8 (8)
N2i—Hg—N2—C1086.5 (6)C8—C7—C11—C12179.7 (7)
Cl1—Hg—N2—C1074.4 (6)C6—C7—C11—C120.0 (12)
Cl1i—Hg—N2—C10154.2 (5)C1—N1—C12—C40.1 (11)
C12—N1—C1—C20.6 (12)Hg—N1—C12—C4174.9 (5)
Hg—N1—C1—C2174.3 (6)C1—N1—C12—C11178.1 (6)
N1—C1—C2—C30.5 (12)Hg—N1—C12—C116.9 (9)
C1—C2—C3—C42.2 (12)C3—C4—C12—N11.6 (11)
C2—C3—C4—C122.7 (11)C5—C4—C12—N1179.4 (9)
C2—C3—C4—C5178.2 (9)C3—C4—C12—C11179.8 (7)
C3—C4—C5—O12.1 (18)C5—C4—C12—C111.2 (13)
C12—C4—C5—O1178.8 (11)N2—C11—C12—N10.3 (10)
C3—C4—C5—C6177.9 (9)C7—C11—C12—N1179.9 (7)
C12—C4—C5—C61.1 (16)N2—C11—C12—C4178.0 (7)
O1—C5—C6—O23.5 (19)C7—C11—C12—C41.9 (11)
C4—C5—C6—O2176.5 (10)O1—C5—C6—O23.5 (19)
O1—C5—C6—C7177.1 (11)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1ii0.952.693.578 (8)156
C9—H9···Cl1iii0.952.783.701 (8)164
Symmetry codes: (ii) x1, y, z; (iii) x+1/2, y, z1/2.

Experimental details

Crystal data
Chemical formula[HgCl2(C12H6N2O2)2]
Mr691.87
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)120
a, b, c (Å)8.2261 (2), 42.6761 (11), 12.6108 (3)
V3)4427.12 (19)
Z8
Radiation typeMo Kα
µ (mm1)7.24
Crystal size (mm)0.20 × 0.10 × 0.06
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.204, 0.651
No. of measured, independent and
observed [I > 2σ(I)] reflections
10751, 2487, 2239
Rint0.075
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.094, 1.05
No. of reflections2487
No. of parameters159
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.27, 0.68
Absolute structureFlack (1983), 1163 Friedel pairs
Absolute structure parameter0.012 (13)

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
Hg—N12.439 (7)Hg—Cl12.5270 (19)
Hg—N22.512 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.952.693.578 (8)156
C9—H9···Cl1ii0.952.783.701 (8)164
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y, z1/2.
 

Footnotes

Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there are gratefully acknowledged. JLW acknowledges support from FAPEMIG (Brazil).

References

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