Bis{2-amino-2-oxo-N-[(1E)-1-(pyridin-2-yl-κN)ethyl­idene]acetohydrazidato-κ2N′,O1}nickel(II)

Kane, C.H.; Thiam, I.E.; Tamboura, F.B.; Gaye, M.; Retailleau, P.

doi:10.1107/S1600536812014109

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m553

doi:10.1107/S1600536812014109

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Bis{2-amino-2-oxo-N-[(1E)-1-(pyridin-2-yl-κN)ethylidene]acetohydrazidato-κ²N′,O¹}nickel(II)

Cheikh Hamidou Kane,^a Ibrahima Elhadj Thiam,^a Farba Bouyagui Tamboura,^a Mohamed Gaye ^a ^* and Pascal Retailleau ^b

^aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bCentre de Recherche de Gif sur Yvette, Institut de Chimie des Substances Naturelles, UPR2301-CNRS, 1 Avenue la Terrasse, 91198 Gif sur Yvette cédex, France
^*Correspondence e-mail: mlgayeastou@yahoo.fr

(Received 29 March 2012; accepted 31 March 2012; online 6 April 2012)

In the title compound, [Ni(C₉H₉N₄O₂)₂], the Ni^II ion is situated on a twofold rotation axis and is coordinated by two O and four N atoms from two tridentate {2-amino-2-oxo-N-[(1E)-1-(pyridin-2-yl-κN)ethylidene]acetohydrazidate ligands in a distorted octahedral geometry. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link the molecules into columns in [001]. The porous crystal packing is further stabilized via π–π interactions between the pyridine rings of neighbouring molecules [centroid–centroid distance = 3.746 (3) Å] with voids of 270 Å³.

Related literature

For the structures of related nickel complexes, see: Dieng et al. (2004 ); Tamboura et al. (2009 ); Mikuriya et al. (1996 ).

Experimental

Crystal data

[Ni(C₉H₉N₄O₂)₂]
M_r = 469.11
Monoclinic, C 2/c
a = 16.703 (3) Å
b = 17.878 (4) Å
c = 8.929 (2) Å
β = 114.915 (5)°
V = 2418.2 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.84 mm⁻¹
T = 293 K
0.21 × 0.14 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.778, T_max = 0.897
6288 measured reflections
1781 independent reflections
1285 reflections with I > 2σ(I)
R_int = 0.046
θ_max = 23.5°

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.137
S = 1.04
1777 reflections
142 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2ⁱ	0.86	2.22	2.976 (5)	147
N4—H4B⋯N3ⁱⁱ	0.86	2.25	3.074 (5)	160
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999 ); cell refinement: DENZO and COLLECT; data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014109/cv5274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014109/cv5274Isup2.hkl

checkCIF report

Comment top

In the title compound (Fig. 1), the Ni^II ion is situated on a twofold rotational and adopts a distorted octahedral geometry. The coordination of the hydrazones to Ni center results in the formation of two five-membered chelating rings. In the two rings, the Ni–N_pyridyl bond lengths of 2.094 (3) Å are larger than those for Ni–N_iminol bonds [1.980 (3) Å]. The Ni–O1 involving the hydrazonic oxygen have the metal-ligand distance of 2.074 (3) Å. The Ni—N and Ni—O bond distances are similar to those observed in other mononuclear Ni^II complexes with similar tridentate ligands (Dieng et al., 2004; Tamboura et al., 2009). The following bond C6–N2 is not altered in the complex and remains with double bond character. The bond C8–N3 which was simple in character becomes a double bond after deprotonation of the N–H function. The N_imino–Ni–O1 and N_pyridyl–Ni–N_imino angles are 78.25 (13)° and 92.04 (13)° respectively. The deviation from 90° of the bond angles involving the chelation observed is presumably due to the formation of five-membered ring (Mikuriya et al., 1996).

In the crystal structure, the intermolecular hydrogen-bonding network involving the acetamide groups and also the N3 atom (Table 1), propagates parallel to the crystallographic c axis (Fig.2). This contributes to display a double inverted X molecular pattern in the ab plane stabilized by π – π stacking interactions between adjacent pyridine rings with the centroid-centroid distance of 3.746 (3) Å.

Related literature top

For the structures of related nickel complexes, see: Dieng et al. (2004); Tamboura et al. (2009); Mikuriya et al. (1996).

Experimental top

2-Amino-2-oxo-N^'-(1-(pyridin-2-yl)ethylidene)acetohydrazide (0.206 g, 1 mmol) was dissolved in 10 ml of ethanol and the LiOH (0.042 g, 2 mmol) was added with thorough shaking. To the resulting solution, Ni(CH₃COO)₂.4H₂O (0.2489 g, 1 mmol) was added. Immediate change of the colour was observed. The mixture was stirred at room temperature during 2 h. The solution was filtered off and concentrated to tenth. Crystals that separated from the brown solution were filtered off and recrystallized in ethanol. On standing for three weeks, suitable X-rays crystals were obtained. Yield: 73.5%. Anal. Calc. for [C₁₈H₁₈N₈O₄Ni] (%): C, 46.09; H, 3.87; N, 23.89. Found: C, 46.06; H, 3.85; N, 23.87. Selected IR data (cm^-1, KBr pellet): 3214, 1728, 1645, 1585, 1459, 768.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. An ORTEP view of the title compound, showing the atom-numbering scheme [symmetry code: (a) -x + 1, y, -z + 1/2]. Displacement ellipsoids are plotted at the 30% probability level.
	Fig. 2. A portion of the crystal packing viewed down the a axis and showing hydrogen bonds as cyan lines.

Bis{2-amino-2-oxo-N-[(1E)-1-(pyridin-2- yl-κN)ethylidene]acetohydrazidato-κ²N',O¹}nickel(II) top

Crystal data top

[Ni(C₉H₉N₄O₂)₂]	F(000) = 968
M_r = 469.11	D_x = 1.289 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 1780 reflections
a = 16.703 (3) Å	θ = 0.4–23.5°
b = 17.878 (4) Å	µ = 0.84 mm⁻¹
c = 8.929 (2) Å	T = 293 K
β = 114.915 (5)°	Block, brown
V = 2418.2 (9) Å³	0.21 × 0.14 × 0.13 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1781 independent reflections
Radiation source: fine-focus sealed tube, Nonius Kappa CCD	1285 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 9 pixels mm^-1	θ_max = 23.5°, θ_min = 2.3°
phi and ω scans	h = −18→18
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −18→20
T_min = 0.778, T_max = 0.897	l = −9→9
6288 measured reflections

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F²) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0757P)²] where P = (F_o² + 2F_c²)/3
1777 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni(C₉H₉N₄O₂)₂]	V = 2418.2 (9) Å³
M_r = 469.11	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 16.703 (3) Å	µ = 0.84 mm⁻¹
b = 17.878 (4) Å	T = 293 K
c = 8.929 (2) Å	0.21 × 0.14 × 0.13 mm
β = 114.915 (5)°

Data collection top

Nonius KappaCCD diffractometer	1781 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	1285 reflections with I > 2σ(I)
T_min = 0.778, T_max = 0.897	R_int = 0.046
6288 measured reflections	θ_max = 23.5°

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
1777 reflections	Δρ_min = −0.30 e Å⁻³
142 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. Five low-resolution reflections were omitted due to beamstop shading (OMIT instruction in SHELX97-L).

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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.30602 (4)	0.2500	0.0392 (3)
O1	0.41866 (19)	0.38561 (16)	0.2833 (3)	0.0451 (8)
O2	0.3304 (2)	0.4879 (2)	0.3757 (4)	0.0722 (11)
N1	0.5999 (2)	0.22513 (19)	0.3236 (4)	0.0438 (9)
N2	0.5383 (2)	0.30400 (18)	0.4922 (4)	0.0368 (8)
N3	0.4949 (2)	0.35081 (19)	0.5577 (4)	0.0406 (9)
N4	0.3876 (3)	0.4413 (2)	0.6353 (4)	0.0572 (11)
H4A	0.3576	0.4710	0.6676	0.069*
H4B	0.4232	0.4094	0.7031	0.069*
C1	0.6314 (3)	0.1867 (3)	0.2321 (6)	0.0567 (13)
H1	0.6064	0.1948	0.1187	0.068*
C2	0.6990 (4)	0.1356 (3)	0.2970 (7)	0.0708 (16)
H2	0.7189	0.1097	0.2290	0.085*
C3	0.7360 (4)	0.1241 (3)	0.4635 (7)	0.0733 (17)
H3	0.7822	0.0902	0.5109	0.088*
C4	0.7050 (3)	0.1624 (3)	0.5594 (6)	0.0631 (14)
H4	0.7302	0.1550	0.6731	0.076*
C5	0.6359 (3)	0.2127 (2)	0.4885 (5)	0.0475 (12)
C6	0.5976 (3)	0.2576 (2)	0.5825 (5)	0.0453 (11)
C7	0.6273 (4)	0.2469 (3)	0.7638 (5)	0.0713 (17)
H7A	0.5935	0.2786	0.8020	0.107*
H7B	0.6887	0.2595	0.8202	0.107*
H7C	0.6189	0.1956	0.7856	0.107*
C8	0.4349 (3)	0.3894 (2)	0.4339 (5)	0.0369 (10)
C9	0.3792 (3)	0.4445 (3)	0.4806 (5)	0.0482 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0409 (5)	0.0462 (5)	0.0311 (5)	0.000	0.0158 (4)	0.000
O1	0.0491 (19)	0.0503 (18)	0.0330 (16)	0.0100 (15)	0.0144 (14)	0.0013 (14)
O2	0.091 (3)	0.080 (3)	0.052 (2)	0.042 (2)	0.036 (2)	0.0173 (19)
N1	0.044 (2)	0.047 (2)	0.040 (2)	0.0055 (18)	0.0176 (18)	−0.0014 (18)
N2	0.037 (2)	0.0394 (19)	0.0332 (19)	0.0013 (18)	0.0144 (16)	0.0023 (17)
N3	0.049 (2)	0.045 (2)	0.0321 (19)	0.0077 (18)	0.0208 (18)	0.0014 (17)
N4	0.064 (3)	0.069 (3)	0.042 (2)	0.023 (2)	0.026 (2)	0.002 (2)
C1	0.058 (3)	0.065 (3)	0.052 (3)	0.008 (3)	0.028 (3)	−0.009 (3)
C2	0.069 (4)	0.075 (4)	0.065 (4)	0.019 (3)	0.025 (3)	−0.019 (3)
C3	0.062 (4)	0.072 (4)	0.072 (4)	0.032 (3)	0.016 (3)	−0.009 (3)
C4	0.058 (3)	0.067 (3)	0.051 (3)	0.020 (3)	0.010 (3)	−0.001 (3)
C5	0.045 (3)	0.051 (3)	0.043 (3)	0.004 (2)	0.015 (2)	−0.001 (2)
C6	0.043 (3)	0.053 (3)	0.036 (2)	0.004 (2)	0.013 (2)	0.004 (2)
C7	0.082 (4)	0.091 (4)	0.036 (3)	0.034 (3)	0.020 (3)	0.012 (3)
C8	0.041 (3)	0.039 (2)	0.031 (2)	−0.001 (2)	0.016 (2)	−0.001 (2)
C9	0.050 (3)	0.057 (3)	0.038 (3)	0.008 (2)	0.018 (2)	0.002 (2)

Geometric parameters (Å, º) top

Ni1—N2ⁱ	1.980 (3)	N4—H4B	0.8600
Ni1—N2	1.980 (3)	C1—C2	1.376 (6)
Ni1—O1ⁱ	2.074 (3)	C1—H1	0.9300
Ni1—O1	2.074 (3)	C2—C3	1.364 (7)
Ni1—N1ⁱ	2.094 (3)	C2—H2	0.9300
Ni1—N1	2.094 (3)	C3—C4	1.359 (7)
O1—C8	1.257 (5)	C3—H3	0.9300
O2—C9	1.225 (5)	C4—C5	1.388 (6)
N1—C1	1.333 (6)	C4—H4	0.9300
N1—C5	1.354 (5)	C5—C6	1.487 (6)
N2—C6	1.283 (5)	C6—C7	1.492 (6)
N2—N3	1.387 (5)	C7—H7A	0.9600
N3—C8	1.330 (5)	C7—H7B	0.9600
N4—C9	1.329 (5)	C7—H7C	0.9600
N4—H4A	0.8600	C8—C9	1.528 (6)

N2ⁱ—Ni1—N2	177.92 (19)	C2—C1—H1	118.3
N2ⁱ—Ni1—O1ⁱ	77.63 (12)	C3—C2—C1	118.3 (5)
N2—Ni1—O1ⁱ	103.84 (12)	C3—C2—H2	120.8
N2ⁱ—Ni1—O1	103.84 (12)	C1—C2—H2	120.8
N2—Ni1—O1	77.63 (12)	C4—C3—C2	119.5 (5)
O1ⁱ—Ni1—O1	93.34 (17)	C4—C3—H3	120.3
N2ⁱ—Ni1—N1ⁱ	78.26 (13)	C2—C3—H3	120.3
N2—Ni1—N1ⁱ	100.27 (13)	C3—C4—C5	120.3 (5)
O1ⁱ—Ni1—N1ⁱ	155.88 (12)	C3—C4—H4	119.9
O1—Ni1—N1ⁱ	92.02 (13)	C5—C4—H4	119.9
N2ⁱ—Ni1—N1	100.27 (13)	N1—C5—C4	120.4 (4)
N2—Ni1—N1	78.26 (13)	N1—C5—C6	115.2 (4)
O1ⁱ—Ni1—N1	92.02 (13)	C4—C5—C6	124.4 (4)
O1—Ni1—N1	155.88 (12)	N2—C6—C5	113.3 (4)
N1ⁱ—Ni1—N1	92.6 (2)	N2—C6—C7	125.5 (4)
C8—O1—Ni1	109.4 (2)	C5—C6—C7	121.2 (4)
C1—N1—C5	118.2 (4)	C6—C7—H7A	109.5
C1—N1—Ni1	129.2 (3)	C6—C7—H7B	109.5
C5—N1—Ni1	112.6 (3)	H7A—C7—H7B	109.5
C6—N2—N3	121.8 (3)	C6—C7—H7C	109.5
C6—N2—Ni1	120.5 (3)	H7A—C7—H7C	109.5
N3—N2—Ni1	117.6 (2)	H7B—C7—H7C	109.5
C8—N3—N2	107.9 (3)	O1—C8—N3	127.4 (4)
C9—N4—H4A	120.0	O1—C8—C9	116.4 (4)
C9—N4—H4B	120.0	N3—C8—C9	116.2 (3)
H4A—N4—H4B	120.0	O2—C9—N4	124.6 (4)
N1—C1—C2	123.4 (5)	O2—C9—C8	119.0 (4)
N1—C1—H1	118.3	N4—C9—C8	116.4 (4)

N2ⁱ—Ni1—O1—C8	177.3 (3)	Ni1—N1—C1—C2	178.8 (4)
N2—Ni1—O1—C8	−1.2 (3)	N1—C1—C2—C3	−0.4 (8)
O1ⁱ—Ni1—O1—C8	−104.6 (3)	C1—C2—C3—C4	0.5 (9)
N1ⁱ—Ni1—O1—C8	98.9 (3)	C2—C3—C4—C5	0.4 (9)
N1—Ni1—O1—C8	−2.1 (5)	C1—N1—C5—C4	1.5 (7)
N2ⁱ—Ni1—N1—C1	3.4 (4)	Ni1—N1—C5—C4	−178.0 (4)
N2—Ni1—N1—C1	−178.1 (4)	C1—N1—C5—C6	179.9 (4)
O1ⁱ—Ni1—N1—C1	−74.4 (4)	Ni1—N1—C5—C6	0.4 (5)
O1—Ni1—N1—C1	−177.2 (3)	C3—C4—C5—N1	−1.4 (8)
N1ⁱ—Ni1—N1—C1	81.9 (4)	C3—C4—C5—C6	−179.6 (5)
N2ⁱ—Ni1—N1—C5	−177.3 (3)	N3—N2—C6—C5	179.9 (3)
N2—Ni1—N1—C5	1.2 (3)	Ni1—N2—C6—C5	4.1 (5)
O1ⁱ—Ni1—N1—C5	104.9 (3)	N3—N2—C6—C7	0.5 (7)
O1—Ni1—N1—C5	2.1 (5)	Ni1—N2—C6—C7	−175.3 (4)
N1ⁱ—Ni1—N1—C5	−98.7 (3)	N1—C5—C6—N2	−2.8 (6)
O1ⁱ—Ni1—N2—C6	−92.3 (3)	C4—C5—C6—N2	175.5 (4)
O1—Ni1—N2—C6	177.3 (3)	N1—C5—C6—C7	176.7 (4)
N1ⁱ—Ni1—N2—C6	87.5 (3)	C4—C5—C6—C7	−5.0 (7)
N1—Ni1—N2—C6	−3.1 (3)	Ni1—O1—C8—N3	1.1 (5)
O1ⁱ—Ni1—N2—N3	91.7 (3)	Ni1—O1—C8—C9	−178.8 (3)
O1—Ni1—N2—N3	1.3 (3)	N2—N3—C8—O1	−0.1 (6)
N1ⁱ—Ni1—N2—N3	−88.5 (3)	N2—N3—C8—C9	179.8 (3)
N1—Ni1—N2—N3	−179.1 (3)	O1—C8—C9—O2	−8.8 (6)
C6—N2—N3—C8	−177.0 (4)	N3—C8—C9—O2	171.4 (4)
Ni1—N2—N3—C8	−1.1 (4)	O1—C8—C9—N4	171.0 (4)
C5—N1—C1—C2	−0.6 (7)	N3—C8—C9—N4	−8.9 (6)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱⁱ	0.86	2.22	2.976 (5)	147
N4—H4B···N3ⁱⁱⁱ	0.86	2.25	3.074 (5)	160

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₉N₄O₂)₂]
M_r	469.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	16.703 (3), 17.878 (4), 8.929 (2)
β (°)	114.915 (5)
V (Å³)	2418.2 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.21 × 0.14 × 0.13

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.778, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	6288, 1781, 1285
R_int	0.046
θ_max (°)	23.5
(sin θ/λ)_max (Å⁻¹)	0.561

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.137, 1.04
No. of reflections	1777
No. of parameters	142
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.30

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱ	0.86	2.22	2.976 (5)	147.2
N4—H4B···N3ⁱⁱ	0.86	2.25	3.074 (5)	159.9

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, y, −z+3/2.

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