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

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ISSN: 2056-9890

[Hexane-2,5-dione bis­­(thio­semi­carba­zon­ato)]nickel(II)

aDepartment of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium, bDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, cDepartment of Chemistry, University of Antwerp, Antwerp, Belgium, dDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and eDeutsches Elektronen-Synchrotron (DESY), Division Structural Dynamics of (Bio)chemical Systems, Notkestrasse 85, 22607 Hamburg, Germany
*Correspondence e-mail: organik10@hotmail.com

(Received 5 May 2013; accepted 9 May 2013; online 15 May 2013)

In the title compound, [Ni(C8H14N6S2)], the NiII ion is coordinated by N2S2 donor atoms of the tetradentate thio­semicarbazone ligand, and has a slightly distorted square-planar geometry. In the crystal, inversion-related mol­ecules are linked via pairs of N—H⋯N and N—H⋯S hydrogen bonds, forming R22(8) ring motifs. Mol­ecules are further linked by slightly weaker N—H⋯N, N—H⋯S and C—H⋯S hydrogen bonds, forming two-dimensional networks which lie parallel to the bc plane.

Related literature

For standard values of bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Cowley et al. (2004[Cowley, A. R., Dilworth, J. R., Donnelly, P. S., Gee, A. D. & Heslop, J. M. (2004). Dalton Trans. pp. 2404-2412.]); Lobana et al. (2011[Lobana, T. S., Kumari, P., Sharma, R., Castineiras, A., Butcher, R. J., Akitsu, T. & Aritake, Y. (2011). Dalton Trans. pp. 3219-3228.]). The anti­tumor and anti­bacterial activity of thio­semicarbazones and thio­semicarbazides has been attributed to their ability to chelate trace metals, see: Kirschner et al. (1966[Kirschner, S., Weu, Y. K., Francis, D. & Bergman, J. G. (1966). J. Med. Chem. 9, 369-375.]). For the preparation of hexan-2,5-dionebis(thio­semicarbazone), see: Nandi et al. (1984[Nandi, A. K., Chaudhuri, S. & Mazumdar, S. K. (1984). Inorg. Chim. Acta, 92, 235-240.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C8H14N6S2)]

  • Mr = 317.08

  • Triclinic, [P \overline 1]

  • a = 7.8928 (3) Å

  • b = 8.0378 (3) Å

  • c = 11.0889 (4) Å

  • α = 69.720 (1)°

  • β = 75.214 (1)°

  • γ = 85.693 (1)°

  • V = 637.96 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.84 mm−1

  • T = 296 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.711, Tmax = 0.711

  • 7275 measured reflections

  • 3078 independent reflections

  • 2833 reflections with I > 2σ(I)

  • Rint = 0.011

Refinement
  • R[F2 > 2σ(F2)] = 0.021

  • wR(F2) = 0.059

  • S = 0.99

  • 3078 reflections

  • 156 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H2N3⋯N2i 0.90 2.16 3.054 (2) 173
N3—H1N3⋯S1ii 0.90 2.58 3.4699 (17) 171
N6—H1N6⋯N2iii 0.90 2.28 3.1248 (19) 156
N6—H2N6⋯S2iv 0.92 2.67 3.5552 (16) 162
C3—H3B⋯S2v 0.96 2.87 3.7513 (17) 152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+2; (iv) -x+1, -y+2, -z+2; (v) x, y-1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2005[Bruker (2005). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The antitumor and antibacterial of thiosemicarbazones and thiosemicarbazides have been attributed to their ability to chelate trace metals (Kirschner et al. 1966). Thiosemicarbazonato complexes are usually synthesized by the conventional approach of simply mixing alcoholic solutions of thiosemicarbazones and stoichiometric amounts of transition metal salt.

The asymmetric unit of the title compound, Fig. 1, comprises a thiosemicarbazone nickel(II) complex in which the NiII ion is coordinated by N2S2 donor atoms with a slightly distorted square-planar geometry. The angle between the mean planes S1–Ni1–N1 and S2–Ni1–N4 is 7.90 (4)°. The mean deviation of atom Ni1 from the mean plane N1–S1–S2–N4 is 0.0861 (5) Å. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those reported for related structures (Cowley et al. (2004); Lobana et al. (2011).

Pairs of intermolecular N—H···N and N—H···S hydrogen bonds make R22(8) ring motifs (Bernstein et al., 1995) [Table 1].

In the crystal, molecules are linked by N—H···N, N—H···S, and C—H···S interactions forming two-dimensional networks which lie parallel to the bc plane (Table 1 and Fig. 2).

Related literature top

For standard values of bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Cowley et al. (2004); Lobana et al. (2011) The antitumor and antibacterial activity of thiosemicarbazones and thiosemicarbazides has been attributed to their ability to chelate trace metals, see: Kirschner et al. (1966). For the preparation of hexan-2,5-dionebis(thiosemicarbazone), see: Nandi et al. (1984).

Experimental top

Hexan-2,5-dionebis(thiosemicarbazone) was prepared by a method similar to that described by (Nandi et al. 1984). Hexan-2,5-dionebis(thiosemicarbazone) (1 mmol, 0.260 g) and nickel(II) acetate (0.66 g, 2.66 mmol) were placed in the main arm of a branched tube. Methanol was carefully added to fill the arms. The tube was sealed and immersed in an oil bath at 333 K while the branched arm was kept at ambient temperature. After 5 days, dark-red crystals (M.p. = 468 K) were isolated in the cooler arm and filtered off, washed with acetone and ether and dried in air (0.192 g; Yield 74%).

Refinement top

The N-bound H atoms were located in a difference Fourier map and constrained to refine on their parent atoms with Uiso(H) = 1.2Ueq(N). The C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.93, 0.96 and 0.97 Å for CH, CH3 and CH2 H-atoms, respectively, with Uiso(H) = k × Ueq(C), where k = 1.5 for CH3 H-atoms, and = 1.2 for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the b-axis of the crystal packing of the title compound, showing the two-dimensional networks lying parallel to the bc plane. Only the H atoms involved in hydrogen bonding are shown.
[Hexane-2,5-dione bis(thiosemicarbazonato)]nickel(II) top
Crystal data top
[Ni(C8H14N6S2)]Z = 2
Mr = 317.08F(000) = 328
Triclinic, P1Dx = 1.651 Mg m3
Hall symbol: -P 1Melting point < 468 K
a = 7.8928 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.0378 (3) ÅCell parameters from 4799 reflections
c = 11.0889 (4) Åθ = 2.7–28.3°
α = 69.720 (1)°µ = 1.84 mm1
β = 75.214 (1)°T = 296 K
γ = 85.693 (1)°Prism, dark-red
V = 637.96 (4) Å30.20 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer
3078 independent reflections
Radiation source: fine-focus sealed tube2833 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
ϕ and ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1010
Tmin = 0.711, Tmax = 0.711k = 1010
7275 measured reflectionsl = 1414
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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0381P)2 + 0.1248P]
where P = (Fo2 + 2Fc2)/3
3078 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
[Ni(C8H14N6S2)]γ = 85.693 (1)°
Mr = 317.08V = 637.96 (4) Å3
Triclinic, P1Z = 2
a = 7.8928 (3) ÅMo Kα radiation
b = 8.0378 (3) ŵ = 1.84 mm1
c = 11.0889 (4) ÅT = 296 K
α = 69.720 (1)°0.20 × 0.20 × 0.20 mm
β = 75.214 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
3078 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2833 reflections with I > 2σ(I)
Tmin = 0.711, Tmax = 0.711Rint = 0.011
7275 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0210 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 0.99Δρmax = 0.28 e Å3
3078 reflectionsΔρmin = 0.21 e Å3
156 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/Ueq
Ni10.74078 (2)0.65209 (2)0.792634 (16)0.02818 (7)
S10.67960 (5)0.84581 (4)0.61696 (4)0.03729 (9)
S20.69288 (5)0.85168 (4)0.88575 (4)0.03624 (9)
N10.77048 (15)0.49799 (14)0.69038 (11)0.0297 (2)
N20.65361 (17)0.51991 (15)0.60798 (12)0.0336 (2)
N30.5029 (2)0.73756 (19)0.48368 (16)0.0567 (4)
H1N30.46580.85030.46020.068*
H2N30.46470.65610.45750.068*
N40.75863 (15)0.48253 (15)0.96705 (12)0.0314 (2)
N50.66994 (18)0.53312 (16)1.07736 (12)0.0381 (3)
N60.57514 (19)0.76724 (18)1.14636 (13)0.0432 (3)
H1N60.53530.68761.22740.052*
H2N60.52980.88011.12460.052*
C10.6069 (2)0.68543 (18)0.56807 (14)0.0350 (3)
C20.64152 (18)0.70094 (18)1.04654 (14)0.0321 (3)
C30.8992 (2)0.2587 (2)0.60870 (16)0.0427 (3)
H3A0.86890.32270.52640.064*
H3B0.81970.15990.65810.064*
H3C1.01670.21630.59100.064*
C40.88697 (18)0.37854 (18)0.68727 (14)0.0321 (3)
C51.01427 (19)0.3582 (2)0.77028 (16)0.0389 (3)
H5A1.04450.47420.76800.047*
H5B1.12070.30550.73370.047*
C60.9390 (2)0.24249 (19)0.91302 (16)0.0376 (3)
H6A0.87530.14490.91150.045*
H6B1.03660.19170.95140.045*
C70.82010 (18)0.32434 (18)1.00507 (15)0.0336 (3)
C80.7864 (2)0.2088 (2)1.14834 (17)0.0457 (4)
H8A0.66550.21641.19130.069*
H8B0.85930.24801.19090.069*
H8C0.81310.08811.15430.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03387 (10)0.02086 (9)0.03506 (10)0.00579 (6)0.01551 (7)0.01199 (7)
S10.0556 (2)0.02174 (16)0.04102 (19)0.00748 (14)0.02323 (16)0.01184 (14)
S20.0531 (2)0.02249 (16)0.03655 (18)0.00501 (14)0.01499 (15)0.01232 (13)
N10.0350 (6)0.0238 (5)0.0344 (6)0.0044 (4)0.0139 (4)0.0118 (4)
N20.0452 (6)0.0261 (5)0.0369 (6)0.0078 (5)0.0209 (5)0.0136 (5)
N30.0945 (12)0.0322 (7)0.0674 (9)0.0223 (7)0.0587 (9)0.0231 (7)
N40.0343 (6)0.0259 (5)0.0382 (6)0.0036 (4)0.0154 (5)0.0119 (5)
N50.0465 (7)0.0305 (6)0.0376 (6)0.0068 (5)0.0131 (5)0.0111 (5)
N60.0557 (8)0.0364 (7)0.0375 (7)0.0089 (6)0.0092 (6)0.0156 (5)
C10.0487 (8)0.0267 (6)0.0352 (7)0.0080 (6)0.0181 (6)0.0132 (5)
C20.0335 (6)0.0296 (6)0.0371 (7)0.0023 (5)0.0138 (5)0.0129 (5)
C30.0498 (9)0.0348 (7)0.0471 (8)0.0102 (6)0.0098 (7)0.0219 (7)
C40.0337 (6)0.0249 (6)0.0372 (7)0.0026 (5)0.0084 (5)0.0106 (5)
C50.0307 (6)0.0355 (7)0.0549 (9)0.0079 (5)0.0151 (6)0.0190 (7)
C60.0402 (7)0.0279 (7)0.0519 (8)0.0116 (6)0.0239 (6)0.0158 (6)
C70.0341 (6)0.0259 (6)0.0448 (7)0.0034 (5)0.0200 (6)0.0105 (6)
C80.0503 (9)0.0325 (7)0.0487 (9)0.0077 (6)0.0185 (7)0.0038 (6)
Geometric parameters (Å, º) top
Ni1—N11.9155 (11)N6—H2N60.9237
Ni1—N41.9751 (12)C3—C41.490 (2)
Ni1—S22.1542 (4)C3—H3A0.9600
Ni1—S12.1718 (4)C3—H3B0.9600
S1—C11.7434 (14)C3—H3C0.9600
S2—C21.7374 (15)C4—C51.4922 (19)
N1—C41.2816 (18)C5—C61.518 (2)
N1—N21.4181 (15)C5—H5A0.9700
N2—C11.3051 (17)C5—H5B0.9700
N3—C11.3392 (19)C6—C71.496 (2)
N3—H1N30.9003C6—H6A0.9700
N3—H2N30.9003C6—H6B0.9700
N4—C71.2923 (17)C7—C81.502 (2)
N4—N51.4202 (17)C8—H8A0.9600
N5—C21.2887 (18)C8—H8B0.9600
N6—C21.3619 (18)C8—H8C0.9600
N6—H1N60.8959
N1—Ni1—N4101.11 (5)C4—C3—H3B109.5
N1—Ni1—S2171.94 (3)H3A—C3—H3B109.5
N4—Ni1—S286.61 (3)C4—C3—H3C109.5
N1—Ni1—S183.28 (3)H3A—C3—H3C109.5
N4—Ni1—S1170.95 (4)H3B—C3—H3C109.5
S2—Ni1—S188.755 (14)N1—C4—C5117.00 (12)
C1—S1—Ni193.57 (5)N1—C4—C3123.93 (13)
C2—S2—Ni194.83 (5)C5—C4—C3119.06 (13)
C4—N1—N2116.52 (11)C4—C5—C6111.47 (12)
C4—N1—Ni1126.65 (10)C4—C5—H5A109.3
N2—N1—Ni1116.82 (8)C6—C5—H5A109.3
C1—N2—N1109.69 (11)C4—C5—H5B109.3
C1—N3—H1N3119.4C6—C5—H5B109.3
C1—N3—H2N3118.7H5A—C5—H5B108.0
H1N3—N3—H2N3121.7C7—C6—C5118.83 (12)
C7—N4—N5111.17 (12)C7—C6—H6A107.6
C7—N4—Ni1133.49 (10)C5—C6—H6A107.6
N5—N4—Ni1114.93 (8)C7—C6—H6B107.6
C2—N5—N4113.32 (12)C5—C6—H6B107.6
C2—N6—H1N6116.4H6A—C6—H6B107.0
C2—N6—H2N6117.9N4—C7—C8122.59 (14)
H1N6—N6—H2N6120.2N4—C7—C6123.82 (13)
N2—C1—N3119.68 (13)C8—C7—C6113.50 (12)
N2—C1—S1122.47 (11)C7—C8—H8A109.5
N3—C1—S1117.82 (11)C7—C8—H8B109.5
N5—C2—N6118.33 (13)H8A—C8—H8B109.5
N5—C2—S2124.34 (11)C7—C8—H8C109.5
N6—C2—S2117.25 (11)H8A—C8—H8C109.5
C4—C3—H3A109.5H8B—C8—H8C109.5
N1—Ni1—S1—C126.73 (7)Ni1—S1—C1—N3159.93 (14)
S2—Ni1—S1—C1152.05 (6)N4—N5—C2—N6172.75 (12)
N4—Ni1—S2—C217.03 (6)N4—N5—C2—S23.74 (18)
S1—Ni1—S2—C2155.19 (5)Ni1—S2—C2—N512.62 (13)
N4—Ni1—N1—C446.03 (13)Ni1—S2—C2—N6170.86 (11)
S1—Ni1—N1—C4141.98 (12)N2—N1—C4—C5178.11 (12)
N4—Ni1—N1—N2135.05 (9)Ni1—N1—C4—C50.80 (19)
S1—Ni1—N1—N236.94 (9)N2—N1—C4—C33.2 (2)
C4—N1—N2—C1148.40 (13)Ni1—N1—C4—C3177.87 (11)
Ni1—N1—N2—C130.63 (15)N1—C4—C5—C683.18 (16)
N1—Ni1—N4—C718.12 (14)C3—C4—C5—C695.57 (16)
S2—Ni1—N4—C7164.20 (13)C4—C5—C6—C782.08 (16)
N1—Ni1—N4—N5153.75 (9)N5—N4—C7—C84.41 (19)
S2—Ni1—N4—N523.93 (9)Ni1—N4—C7—C8167.68 (11)
C7—N4—N5—C2165.09 (13)N5—N4—C7—C6171.94 (13)
Ni1—N4—N5—C221.23 (15)Ni1—N4—C7—C616.0 (2)
N1—N2—C1—N3176.82 (15)C5—C6—C7—N49.3 (2)
N1—N2—C1—S11.41 (18)C5—C6—C7—C8167.36 (13)
Ni1—S1—C1—N221.81 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H2N3···N2i0.902.163.054 (2)173
N3—H1N3···S1ii0.902.583.4699 (17)171
N6—H1N6···N2iii0.902.283.1248 (19)156
N6—H2N6···S2iv0.922.673.5552 (16)162
C3—H3B···S2v0.962.873.7513 (17)152
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+2; (iv) x+1, y+2, z+2; (v) x, y1, z.

Experimental details

Crystal data
Chemical formula[Ni(C8H14N6S2)]
Mr317.08
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.8928 (3), 8.0378 (3), 11.0889 (4)
α, β, γ (°)69.720 (1), 75.214 (1), 85.693 (1)
V3)637.96 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.84
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.711, 0.711
No. of measured, independent and
observed [I > 2σ(I)] reflections
7275, 3078, 2833
Rint0.011
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.059, 0.99
No. of reflections3078
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.21

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H2N3···N2i0.902.163.054 (2)173
N3—H1N3···S1ii0.902.583.4699 (17)171
N6—H1N6···N2iii0.902.283.1248 (19)156
N6—H2N6···S2iv0.922.673.5552 (16)162
C3—H3B···S2v0.962.873.7513 (17)152
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+2; (iv) x+1, y+2, z+2; (v) x, y1, z.
 

Acknowledgements

The authors thank the Chemistry Department of BSU for providing the X-ray diffraction facility.

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