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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages m1344-m1345

Tetra­kis(5,7-di­methyl­quinolin-8-olato-κ2N,O)zirconium(IV) di­methyl­form­amide disolvate

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
*Correspondence e-mail: steynm@ufs.ac.za

(Received 20 September 2012; accepted 8 October 2012; online 13 October 2012)

In the title compound, [Zr(C11H10NO)4]·2C3H7NO, the ZrIV ion is coordinated by four bidentate 5,7-dimethylquinolin-8-olate ligands in a slightly distorted square-anti­prismatic coordination environment. The asymmetric unit also contains two N,N′-dimethyl­formamide (DMF) solvent mol­ecules. In the crystal, a weak C—H⋯O hydrogen bond links the complex mol­ecule to a solvent mol­ecule and weak ππ stacking inter­actions [centroid–centroid distance = 3.671 (3) Å] also occur. One of the DMF solvent mol­ecules was refined as disordered over three sets of sites, with refined occupancies in the ratio of 0.391 (9):0.342 (10):0.267 (7).

Related literature

For N,O- and O,O′-bidentate ligand complexes of zirconium and hafnium, see: Calderazzo et al. (1998[Calderazzo, F., Englert, U., Maichle-Mossmer, C., Marchetti, F., Pampaloni, G., Petroni, D., Pinzino, C., Strähle, J. & Tripepi, G. (1998). Inorg. Chim. Acta, 270, 177-188.]); Demakopoulos et al. (1995[Demakopoulos, I., Klouras, N., Raptopoulou, C. P. & Terzis, A. (1995). Z. Anorg. Allg. Chem. 621, 1761-1766.]); Steyn et al. (2008[Steyn, M., Roodt, A. & Steyl, G. (2008). Acta Cryst. E64, m827.], 2011[Steyn, M., Visser, H. G., Roodt, A. & Muller, T. J. (2011). Acta Cryst. E67, m1240-m1241.]); Viljoen et al. (2008[Viljoen, J. A., Muller, A. & Roodt, A. (2008). Acta Cryst. E64, m838-m839.], 2009a[Viljoen, J. A., Visser, H. G., Roodt, A. & Steyn, M. (2009a). Acta Cryst. E65, m1514-m1515.],b[Viljoen, J. A., Visser, H. G., Roodt, A. & Steyn, M. (2009b). Acta Cryst. E65, m1367-m1368.]; 2010a[Viljoen, J. A., Visser, H. G. & Roodt, A. (2010a). Acta Cryst. E66, m603-m604.],b[Viljoen, J. A., Visser, H. G. & Roodt, A. (2010b). Acta Cryst. E66, m1053-m1054.]); Zherikova et al. (2005[Zherikova, K. V., Morozova, N. B., Kurateva, N. V., Baidina, I. A., Stabnikov, P. A. & Igumenov, I. K. (2005). J. Struct. Chem. 46, 1039-1046.], 2006[Zherikova, K. V., Morozova, N. B., Baidina, I. A., Peresypkina, E. V. & Igumenov, I. K. (2006). J. Struct. Chem. 47, 570-574.], 2008[Zherikova, K. V., Baidina, I. A., Morozova, N. B., Kurateva, N. V. & Igumenov, I. K. (2008). J. Struct. Chem. 49, 1098-1103.]). For our ongoing research of structure reactivity relationships in catalysis, separation chemistry and other industrial reaction mechanisms, see: Roodt et al. (2011[Roodt, A., Visser, H. G. & Brink, A. (2011). Crystallogr. Rev. 17, 241-280.]); Schutte et al. (2011[Schutte, M., Kemp, G., Visser, H. G. & Roodt, A. (2011). Inorg. Chem. 50, 12486-12498.]); Brink et al. (2010[Brink, A., Roodt, A., Steyl, G. & Visser, H. G. (2010). Dalton Trans. 39, 5572-5578.]); Ferreira et al. (2007[Ferreira, A. C., Crous, R., Bennie, L., Meij, A. M. M., Blann, K., Bezuidenhoudt, B. C. B., Young, D. A., Green, M. J. & Roodt, A. (2007). Angew. Chem. Int. Ed. 46, 2273-2275.]); Haumann et al. (2004[Haumann, M., Meijboom, R., Moss, J. R. & Roodt, A. (2004). Dalton Trans. pp. 1679-1686.]).

[Scheme 1]

Experimental

Crystal data
  • [Zr(C11H10NO)4]·2C3H7NO

  • Mr = 926.21

  • Orthorhombic, P n a 21

  • a = 15.572 (5) Å

  • b = 18.706 (5) Å

  • c = 15.853 (5) Å

  • V = 4618 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 100 K

  • 0.26 × 0.14 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.928, Tmax = 0.963

  • 61276 measured reflections

  • 11142 independent reflections

  • 8497 reflections with I > 2σ(I)

  • Rint = 0.064

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.099

  • S = 1.02

  • 11142 reflections

  • 671 parameters

  • 299 restraints

  • H-atom parameters constrained

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.39 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 5375 Friedel pairs

  • Flack parameter: −0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14A—H14E⋯O201i 0.96 2.43 3.358 (7) 161
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

This study forms part of our ongoing research of structure reactivity relationships in catalysis, separation chemistry and other industrial reaction mechanisms including radio pharmacy (Roodt et al. 2011; Schutte et al. 2011; Brink et al. 2010; Ferreira et al. 2007; Haumann et al. 2004; Steyn et al. 2008, 2011; Viljoen et al. 2008, 2009a,b, 2010a,b).

The asymmetric unit of the title compound, [Zr(C10H11NO)4].2C3H7NO, with C10H11NO (diMeOx) = 5,7-Dimethyl-8-quinolinol, consists of a ZrIV ion coordinated to four bidentate ligands (diMeOx), as well as two N,N'-dimethylformamide (DMF) solvent molecules. In the complex molecule (Fig. 1) the ZrIV ion lies at the centre of an approximate square antiprismatic coordination polyhedron of the N,O-coordination ligand atoms, with a small distortion towards dodecahedral geometry. The Zr—N and Zr—O bond distances range from 2.094 (2) to 2.117 (2) Å and 2.398 (2) to 2.438 (2) Å, respectively. The N—Zr—O bite angles range from 69.70 (8)° to 70.55 (8)°.

In the crystal, a weak C—H···O hydrogen bond connects the complex molecule to a solvent molecule (Table 1). In addition, weak ππ interactions exist between the pyridine rings of the diMeOx ligand and symmetry related molecules (1 - x, 1 - y, 1/2 + z) , with interplanar and centroid-to-centroid distances of 3.433 (4) Å and 3.671 (3) Å, respectively (Figure 2).

Related literature top

For N,O- and O,O'-bidentate ligand complexes of zirconium and hafnium, see: Calderazzo et al. (1998); Demakopoulos et al. (1995); Steyn et al. (2008, 2011); Viljoen et al. (2008, 2009a,b; 2010a,b); Zherikova et al. (2005, 2006, 2008). For our ongoing research of structure reactivity relationships in catalysis, separation chemistry and other industrial reaction mechanisms, see: Roodt et al. (2011); Schutte et al. (2011); Brink et al. (2010); Ferreira et al. (2007); Haumann et al. (2004). Scheme - show DMF in full

Experimental top

Chemicals were purchased from Sigma-Aldrich and used as received. ZrCl4 (101.3 mg, 0.435 mmol) and 5,7-Dimethyl-8-quinolinol (diMeOxH) (228.2 mg, 1.317 mmol) was separately dissolved in DMF (2.5 ml ea) and heated to 60°C. The diMeOxH solution as added drop-wise to the zirconium solution and stirred at 333 K for 30 minutes. The reaction solution was removed from heating, covered and left to stand. Red cuboid crystals, suitable for single X-Ray diffraction, formed after 10 days. (Yield: 203 mg, 79%).

Refinement top

H atoms were placed inidealized positions (C—H = 0.93–0.96Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2–1.5Ueq(C). The highest residual electron density was located 0.95 Å from O102. One of the DMF solvent molecules was refined as disordered over three sets of sites with refined occupancies in a ratio of 0.391 (9):0.342 (10):0.267 (7).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structre of the Zr complex of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms and the solvent molecules are omitted for clarity.
[Figure 2] Fig. 2. Part of the crystal structure with weak ππ interactions shown as dashed lines.
Tetrakis(5,7-dimethylquinolin-8-olato-κ2N,O)zirconium(IV) dimethylformamide disolvate top
Crystal data top
[Zr(C11H10NO)4]·2C3H7NOF(000) = 1936
Mr = 926.21Dx = 1.332 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 9914 reflections
a = 15.572 (5) Åθ = 2.6–24.6°
b = 18.706 (5) ŵ = 0.29 mm1
c = 15.853 (5) ÅT = 100 K
V = 4618 (2) Å3Cuboid, red
Z = 40.26 × 0.14 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
11142 independent reflections
Radiation source: sealed tube8497 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ϕ and ω scansθmax = 28°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 2020
Tmin = 0.928, Tmax = 0.963k = 2224
61276 measured reflectionsl = 2020
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.3005P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
11142 reflectionsΔρmax = 0.42 e Å3
671 parametersΔρmin = 0.39 e Å3
299 restraintsAbsolute structure: Flack (1983), 5375 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
Crystal data top
[Zr(C11H10NO)4]·2C3H7NOV = 4618 (2) Å3
Mr = 926.21Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 15.572 (5) ŵ = 0.29 mm1
b = 18.706 (5) ÅT = 100 K
c = 15.853 (5) Å0.26 × 0.14 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
11142 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
8497 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.963Rint = 0.064
61276 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.099Δρmax = 0.42 e Å3
S = 1.02Δρmin = 0.39 e Å3
11142 reflectionsAbsolute structure: Flack (1983), 5375 Friedel pairs
671 parametersAbsolute structure parameter: 0.01 (3)
299 restraints
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
Zr010.966490 (14)0.144904 (13)0.35471 (2)0.02304 (7)
N1020.96042 (15)0.03648 (14)0.43981 (17)0.0262 (6)
O1010.89103 (13)0.17184 (11)0.46024 (13)0.0297 (5)
O1041.02836 (11)0.19244 (11)0.24980 (13)0.0271 (5)
N1040.87759 (15)0.23775 (13)0.29748 (17)0.0262 (6)
O1030.85773 (12)0.09319 (11)0.30675 (14)0.0279 (5)
N1011.01720 (16)0.25663 (13)0.41574 (17)0.0294 (6)
N1031.01035 (15)0.04558 (13)0.26899 (16)0.0251 (6)
O1021.08748 (12)0.12297 (11)0.40715 (14)0.0271 (5)
C1161.1890 (2)0.04673 (17)0.4780 (2)0.0326 (7)
C1280.79960 (18)0.25709 (16)0.3227 (2)0.0295 (7)
H1280.77610.23490.36980.035*
C1100.8931 (2)0.00201 (18)0.4599 (2)0.0339 (8)
H1100.83920.01350.44270.041*
C1220.95422 (19)0.05997 (17)0.1978 (2)0.0260 (7)
C1070.8621 (2)0.23826 (18)0.5857 (2)0.0352 (8)
C1250.79013 (19)0.00990 (18)0.2458 (2)0.0363 (8)
C1211.03962 (19)0.07799 (19)0.1757 (2)0.0320 (8)
H1211.05040.11930.14480.038*
C1181.03964 (18)0.01552 (17)0.46759 (19)0.0247 (6)
C1110.8992 (2)0.0659 (2)0.5063 (2)0.0423 (9)
H1110.85020.09220.5190.051*
C1090.97617 (19)0.27293 (17)0.4900 (2)0.0291 (7)
C1201.1060 (2)0.03520 (18)0.1995 (2)0.0352 (8)
H1201.16210.04640.18410.042*
C1141.1373 (2)0.06654 (18)0.5408 (2)0.0332 (8)
C1171.10771 (19)0.06285 (17)0.4490 (2)0.0278 (7)
C1290.75120 (19)0.30983 (17)0.2808 (2)0.0348 (8)
H1290.69650.32160.29970.042*
C1191.0886 (2)0.02635 (18)0.2479 (2)0.0307 (7)
H1191.13440.05450.26570.037*
C1341.03493 (19)0.27832 (19)0.1369 (2)0.0355 (8)
C1270.94307 (19)0.00394 (16)0.2438 (2)0.0251 (7)
C1350.9944 (2)0.24636 (17)0.2046 (2)0.0270 (7)
C1310.8681 (2)0.32476 (19)0.1829 (2)0.0343 (7)
C1120.9788 (2)0.0889 (2)0.5328 (2)0.0389 (9)
H1120.98370.13130.5630.047*
C1151.2008 (2)0.01833 (18)0.5218 (2)0.0381 (8)
H1151.25620.02940.53910.046*
C1011.0838 (2)0.29617 (16)0.3917 (2)0.0341 (8)
H1011.11070.28590.34070.041*
C1131.0527 (2)0.04862 (17)0.5143 (2)0.0296 (7)
C1021.1149 (2)0.35297 (18)0.4411 (3)0.0429 (9)
H1021.16210.37940.42310.051*
C1041.0026 (2)0.32912 (19)0.5431 (3)0.0400 (9)
C1360.91150 (19)0.27068 (17)0.2282 (2)0.0294 (7)
C14B1.1235 (2)0.2566 (2)0.1106 (2)0.0412 (9)
H14A1.1650.28180.14410.062*
H14B1.13180.2680.05210.062*
H14C1.13040.20610.11870.062*
C1330.9898 (3)0.3325 (2)0.0928 (3)0.0465 (10)
H1331.01690.35340.04670.056*
C1260.86090 (18)0.03010 (16)0.2668 (2)0.0272 (7)
C12A1.1540 (2)0.13471 (18)0.5890 (2)0.0427 (9)
H12A1.21460.14020.59780.064*
H12B1.13270.17470.55720.064*
H12C1.12520.13270.64250.064*
C1240.8028 (2)0.07534 (18)0.2024 (2)0.0428 (9)
H1240.75450.10240.18970.051*
C1080.9078 (2)0.22615 (17)0.5113 (2)0.0302 (7)
C1031.0751 (2)0.36913 (19)0.5161 (3)0.0460 (10)
H1031.09570.40640.54920.055*
C13A0.8899 (2)0.17105 (18)0.1312 (3)0.0425 (9)
H13A0.83420.19140.12160.064*
H13B0.9240.20350.1640.064*
H13C0.91760.16250.0780.064*
C1060.8905 (2)0.2956 (2)0.6375 (2)0.0469 (10)
H1060.86120.3030.68780.056*
C11B0.7879 (2)0.1918 (2)0.6073 (2)0.0416 (9)
H11A0.73880.2060.57470.062*
H11B0.7750.19660.66630.062*
H11C0.80180.1430.5950.062*
C1050.9568 (3)0.3407 (2)0.6200 (3)0.0506 (12)
C13B0.7013 (2)0.0169 (2)0.2666 (3)0.0574 (12)
H13D0.68540.0010.3220.086*
H13E0.66110.00140.22610.086*
H13F0.70080.06820.26490.086*
C12B1.2621 (2)0.09893 (19)0.4674 (3)0.0428 (9)
H12D1.28820.0920.41310.064*
H12E1.3040.0910.51080.064*
H12F1.24060.14690.47140.064*
C14A0.8651 (3)0.4165 (3)0.0639 (3)0.0684 (14)
H14D0.90450.43560.02310.103*
H14E0.8480.45360.10220.103*
H14F0.81540.3980.03560.103*
C1300.7850 (2)0.34339 (18)0.2126 (2)0.0377 (8)
H1300.75360.37870.18520.045*
C1230.8805 (2)0.10150 (17)0.1781 (2)0.0328 (8)
C1320.9089 (3)0.3563 (2)0.1132 (3)0.0496 (10)
C11A0.9852 (3)0.3981 (3)0.6804 (3)0.0790 (17)
H11D0.9760.44420.65530.119*
H11E1.04510.39220.69290.119*
H11F0.95250.39460.73160.119*
N2010.5982 (2)0.0128 (2)0.8446 (3)0.0738 (11)
C2020.5442 (3)0.0454 (3)0.8137 (3)0.0685 (13)
H20A0.55620.05370.75510.103*
H20B0.48480.03260.82020.103*
H20C0.55590.0880.84530.103*
C2030.5743 (5)0.0405 (5)0.9247 (5)0.144 (3)
H20D0.60920.08130.93770.216*
H20E0.58240.00450.96710.216*
H20F0.5150.05450.92350.216*
C2010.6631 (3)0.0338 (3)0.7986 (5)0.0925 (18)
H2010.6960.06950.82370.111*
O2010.6878 (2)0.0165 (2)0.7320 (3)0.0958 (13)
N310.372 (2)0.2574 (12)0.8644 (9)0.142 (6)0.342 (10)
C31A0.464 (2)0.2579 (16)0.8591 (10)0.141 (8)0.342 (10)
H31A0.4850.20970.85640.211*0.342 (10)
H31B0.48750.28110.9080.211*0.342 (10)
H31C0.48150.28330.80930.211*0.342 (10)
C31B0.331 (2)0.3202 (14)0.8686 (13)0.158 (9)0.342 (10)
H31D0.37210.35850.86490.237*0.342 (10)
H31E0.30090.32340.92120.237*0.342 (10)
H31F0.29110.32370.82280.237*0.342 (10)
C31C0.3383 (19)0.1890 (12)0.8670 (13)0.151 (6)0.342 (10)
H31J0.28080.17670.8740.181*0.342 (10)
O310.4022 (14)0.1459 (8)0.8578 (11)0.169 (7)0.342 (10)
N320.5527 (18)0.2747 (12)0.8555 (18)0.163 (8)0.267 (7)
C32B0.476 (2)0.3148 (16)0.848 (3)0.171 (10)0.267 (7)
H32A0.4890.36270.83070.257*0.267 (7)
H32B0.44640.31570.90110.257*0.267 (7)
H32C0.43920.29290.80620.257*0.267 (7)
C32C0.546 (2)0.2060 (11)0.8783 (12)0.169 (10)0.267 (7)
H32D0.48690.19310.88260.253*0.267 (7)
H32E0.57380.19920.9320.253*0.267 (7)
H32F0.57380.17650.83680.253*0.267 (7)
C32A0.6322 (19)0.3019 (16)0.841 (2)0.198 (11)0.267 (7)
H32J0.63790.34970.82570.238*0.267 (7)
O320.6989 (19)0.2633 (15)0.8475 (15)0.237 (12)0.267 (7)
N330.3685 (14)0.2750 (9)0.8788 (12)0.127 (5)0.391 (9)
C33A0.4579 (15)0.2793 (11)0.8624 (16)0.112 (6)0.391 (9)
H33A0.48570.23720.88360.167*0.391 (9)
H33B0.48110.32070.88990.167*0.391 (9)
H33C0.46720.28290.80270.167*0.391 (9)
C33C0.3514 (15)0.2052 (7)0.9044 (9)0.122 (6)0.391 (9)
H33D0.40440.18120.91660.183*0.391 (9)
H33E0.32170.18030.86030.183*0.391 (9)
H33F0.31630.20610.95420.183*0.391 (9)
C33B0.3106 (17)0.3250 (11)0.8571 (17)0.130 (6)0.391 (9)
H33J0.32850.36430.82580.156*0.391 (9)
O330.2314 (12)0.3201 (7)0.8785 (8)0.142 (6)0.391 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zr010.01669 (11)0.02212 (12)0.03031 (13)0.00031 (10)0.00125 (16)0.00248 (17)
N1020.0214 (13)0.0287 (15)0.0285 (15)0.0003 (11)0.0024 (11)0.0051 (12)
O1010.0275 (11)0.0256 (11)0.0360 (13)0.0039 (9)0.0014 (9)0.0050 (10)
O1040.0177 (10)0.0272 (11)0.0365 (12)0.0001 (8)0.0009 (9)0.0015 (10)
N1040.0174 (11)0.0264 (13)0.0347 (15)0.0011 (10)0.0020 (10)0.0047 (12)
O1030.0164 (9)0.0280 (11)0.0393 (12)0.0005 (8)0.0008 (9)0.0068 (10)
N1010.0253 (13)0.0243 (13)0.0387 (16)0.0033 (10)0.0082 (11)0.0033 (12)
N1030.0167 (12)0.0252 (14)0.0335 (15)0.0006 (10)0.0018 (11)0.0004 (12)
O1020.0196 (10)0.0249 (11)0.0370 (12)0.0015 (8)0.0035 (9)0.0004 (10)
C1160.0258 (16)0.0304 (18)0.0415 (19)0.0009 (13)0.0038 (14)0.0018 (15)
C1280.0205 (14)0.0276 (16)0.0403 (17)0.0005 (12)0.0012 (12)0.0038 (13)
C1100.0227 (16)0.042 (2)0.0371 (19)0.0007 (14)0.0033 (14)0.0016 (16)
C1220.0219 (15)0.0226 (16)0.0334 (17)0.0000 (12)0.0004 (13)0.0030 (14)
C1070.0315 (17)0.041 (2)0.0326 (18)0.0204 (15)0.0063 (14)0.0057 (16)
C1250.0208 (15)0.0357 (19)0.052 (2)0.0039 (13)0.0038 (14)0.0126 (17)
C1210.0267 (17)0.032 (2)0.037 (2)0.0015 (14)0.0043 (14)0.0106 (16)
C1180.0213 (15)0.0269 (16)0.0258 (16)0.0031 (12)0.0046 (13)0.0007 (13)
C1110.0301 (18)0.044 (2)0.053 (2)0.0066 (16)0.0078 (17)0.0118 (19)
C1090.0299 (17)0.0240 (17)0.0334 (18)0.0102 (13)0.0109 (14)0.0072 (14)
C1200.0206 (15)0.040 (2)0.045 (2)0.0000 (14)0.0039 (14)0.0122 (17)
C1140.0279 (16)0.0340 (19)0.0377 (19)0.0061 (14)0.0001 (14)0.0048 (16)
C1170.0276 (15)0.0256 (17)0.0300 (16)0.0041 (13)0.0012 (13)0.0007 (14)
C1290.0192 (15)0.0328 (18)0.053 (2)0.0029 (13)0.0028 (15)0.0011 (17)
C1190.0221 (15)0.0333 (19)0.0368 (19)0.0022 (13)0.0018 (14)0.0028 (15)
C1340.0251 (16)0.044 (2)0.0375 (18)0.0005 (15)0.0014 (14)0.0034 (16)
C1270.0203 (14)0.0277 (17)0.0274 (17)0.0025 (13)0.0007 (12)0.0033 (14)
C1350.0213 (14)0.0269 (18)0.0328 (17)0.0000 (13)0.0055 (13)0.0013 (14)
C1310.0293 (16)0.0392 (19)0.0346 (19)0.0025 (14)0.0048 (14)0.0047 (16)
C1120.0347 (19)0.034 (2)0.048 (2)0.0044 (15)0.0082 (16)0.0074 (17)
C1150.0284 (16)0.038 (2)0.048 (2)0.0093 (15)0.0040 (15)0.0039 (17)
C1010.0267 (16)0.0250 (16)0.050 (2)0.0008 (13)0.0088 (14)0.0022 (15)
C1130.0319 (17)0.0268 (18)0.0302 (18)0.0027 (14)0.0051 (14)0.0002 (15)
C1020.0318 (17)0.0267 (18)0.070 (3)0.0012 (14)0.0184 (18)0.0057 (18)
C1040.0320 (17)0.0313 (18)0.057 (2)0.0131 (16)0.0177 (17)0.0137 (18)
C1360.0231 (15)0.0304 (18)0.0346 (18)0.0037 (13)0.0023 (13)0.0026 (15)
C14B0.0279 (16)0.052 (2)0.043 (2)0.0004 (15)0.0011 (15)0.0115 (18)
C1330.041 (2)0.060 (3)0.039 (2)0.008 (2)0.0059 (19)0.019 (2)
C1260.0219 (14)0.0234 (16)0.0363 (18)0.0006 (12)0.0017 (13)0.0039 (14)
C12A0.0377 (19)0.039 (2)0.052 (2)0.0090 (16)0.0012 (17)0.0084 (18)
C1240.0273 (17)0.038 (2)0.063 (2)0.0136 (15)0.0015 (16)0.0142 (19)
C1080.0289 (16)0.0291 (17)0.0324 (17)0.0119 (13)0.0084 (14)0.0044 (15)
C1030.0329 (19)0.034 (2)0.071 (3)0.0071 (15)0.0234 (19)0.0204 (19)
C13A0.0358 (19)0.0308 (18)0.061 (2)0.0058 (15)0.0002 (17)0.0134 (18)
C1060.041 (2)0.062 (3)0.037 (2)0.029 (2)0.0102 (16)0.0189 (19)
C11B0.0334 (18)0.056 (2)0.0352 (19)0.0199 (17)0.0002 (15)0.0069 (18)
C1050.044 (2)0.054 (3)0.054 (3)0.0193 (19)0.020 (2)0.031 (2)
C13B0.0236 (17)0.056 (2)0.093 (3)0.0054 (16)0.0032 (19)0.030 (2)
C12B0.0256 (16)0.043 (2)0.060 (2)0.0029 (15)0.0115 (16)0.0133 (19)
C14A0.056 (3)0.089 (4)0.061 (3)0.032 (2)0.006 (2)0.033 (3)
C1300.0277 (16)0.040 (2)0.045 (2)0.0102 (14)0.0068 (15)0.0014 (17)
C1230.0296 (16)0.0275 (18)0.041 (2)0.0038 (14)0.0031 (14)0.0047 (15)
C1320.041 (2)0.062 (3)0.046 (2)0.0135 (19)0.0007 (18)0.017 (2)
C11A0.056 (3)0.092 (4)0.089 (4)0.020 (3)0.021 (3)0.064 (3)
N2010.0424 (18)0.081 (2)0.098 (3)0.0171 (18)0.001 (2)0.007 (3)
C2020.041 (2)0.080 (3)0.084 (3)0.003 (2)0.001 (2)0.010 (3)
C2030.094 (5)0.185 (8)0.154 (7)0.070 (5)0.007 (5)0.073 (6)
C2010.049 (3)0.090 (4)0.138 (5)0.010 (3)0.004 (3)0.013 (4)
O2010.0446 (19)0.112 (3)0.131 (4)0.0012 (19)0.018 (2)0.028 (3)
N310.285 (12)0.108 (10)0.034 (7)0.057 (10)0.031 (9)0.024 (9)
C31A0.296 (17)0.070 (15)0.055 (11)0.019 (14)0.002 (15)0.018 (12)
C31B0.310 (19)0.106 (14)0.058 (13)0.036 (16)0.054 (15)0.004 (12)
C31C0.301 (14)0.100 (11)0.052 (10)0.057 (11)0.030 (12)0.010 (11)
O310.293 (19)0.149 (12)0.064 (7)0.061 (12)0.002 (15)0.001 (10)
N320.31 (2)0.136 (15)0.047 (9)0.014 (16)0.053 (16)0.010 (12)
C32B0.34 (2)0.13 (2)0.045 (13)0.03 (2)0.010 (19)0.013 (18)
C32C0.38 (3)0.095 (15)0.032 (11)0.051 (19)0.061 (15)0.000 (10)
C32A0.35 (2)0.17 (2)0.071 (15)0.027 (19)0.043 (19)0.029 (15)
O320.39 (3)0.26 (3)0.061 (11)0.14 (2)0.011 (18)0.060 (16)
N330.261 (11)0.078 (8)0.043 (7)0.057 (9)0.005 (8)0.020 (7)
C33A0.243 (15)0.049 (12)0.043 (10)0.032 (11)0.019 (12)0.018 (9)
C33C0.307 (17)0.030 (7)0.029 (7)0.007 (9)0.020 (10)0.005 (6)
C33B0.267 (14)0.083 (9)0.040 (7)0.059 (11)0.025 (11)0.009 (9)
O330.236 (15)0.097 (8)0.094 (10)0.040 (11)0.001 (10)0.003 (7)
Geometric parameters (Å, º) top
Zr01—O1032.093 (2)C12A—H12A0.96
Zr01—O1022.100 (2)C12A—H12B0.96
Zr01—O1012.106 (2)C12A—H12C0.96
Zr01—O1042.118 (2)C124—C1231.360 (4)
Zr01—N1042.399 (2)C124—H1240.93
Zr01—N1032.401 (3)C103—H1030.93
Zr01—N1012.435 (3)C13A—C1231.505 (5)
Zr01—N1022.438 (3)C13A—H13A0.96
N102—C1101.310 (4)C13A—H13B0.96
N102—C1181.367 (4)C13A—H13C0.96
O101—C1081.325 (4)C106—C1051.361 (6)
O104—C1351.345 (4)C106—H1060.93
N104—C1281.329 (4)C11B—H11A0.96
N104—C1361.365 (4)C11B—H11B0.96
O103—C1261.340 (4)C11B—H11C0.96
N101—C1011.330 (4)C105—C11A1.506 (6)
N101—C1091.374 (4)C13B—H13D0.96
N103—C1191.314 (4)C13B—H13E0.96
N103—C1271.365 (4)C13B—H13F0.96
O102—C1171.343 (4)C12B—H12D0.96
C116—C1171.380 (4)C12B—H12E0.96
C116—C1151.413 (5)C12B—H12F0.96
C116—C12B1.510 (4)C14A—C1321.531 (5)
C128—C1291.408 (4)C14A—H14D0.96
C128—H1280.93C14A—H14E0.96
C110—C1111.407 (5)C14A—H14F0.96
C110—H1100.93C130—H1300.93
C122—C1271.412 (4)C11A—H11D0.96
C122—C1211.416 (4)C11A—H11E0.96
C122—C1231.421 (4)C11A—H11F0.96
C107—C1081.395 (5)N201—C2011.307 (7)
C107—C1061.422 (5)N201—C2031.422 (8)
C107—C11B1.486 (5)N201—C2021.461 (6)
C125—C1261.373 (4)C202—H20A0.96
C125—C1241.418 (5)C202—H20B0.96
C125—C13B1.508 (4)C202—H20C0.96
C121—C1201.361 (4)C203—H20D0.96
C121—H1210.93C203—H20E0.96
C118—C1171.412 (4)C203—H20F0.96
C118—C1131.424 (5)C201—O2011.169 (7)
C111—C1121.377 (5)C201—H2010.93
C111—H1110.93N31—C31B1.341 (17)
C109—C1041.408 (5)N31—C31C1.387 (17)
C109—C1081.419 (5)N31—C31A1.430 (16)
C120—C1191.410 (5)C31A—H31A0.96
C120—H1200.93C31A—H31B0.96
C114—C1151.372 (4)C31A—H31C0.96
C114—C1131.424 (4)C31B—H31D0.96
C114—C12A1.509 (5)C31B—H31E0.96
C129—C1301.356 (5)C31B—H31F0.96
C129—H1290.93C31C—O311.29 (2)
C119—H1190.93C31C—H31J0.93
C134—C1351.381 (5)N32—C32C1.338 (17)
C134—C1331.417 (5)N32—C32A1.359 (18)
C134—C14B1.497 (4)N32—C32B1.422 (18)
C127—C1261.417 (4)C32B—H32A0.96
C135—C1361.419 (4)C32B—H32B0.96
C131—C1321.405 (5)C32B—H32C0.96
C131—C1361.413 (4)C32C—H32D0.96
C131—C1301.421 (4)C32C—H32E0.96
C112—C1131.406 (5)C32C—H32F0.96
C112—H1120.93C32A—O321.27 (2)
C115—H1150.93C32A—H32J0.93
C101—C1021.406 (5)N33—C33B1.343 (16)
C101—H1010.93N33—C33C1.392 (15)
C102—C1031.375 (6)N33—C33A1.418 (15)
C102—H1020.93C33A—H33A0.96
C104—C1031.421 (6)C33A—H33B0.96
C104—C1051.428 (6)C33A—H33C0.96
C14B—H14A0.96C33C—H33D0.96
C14B—H14B0.96C33C—H33E0.96
C14B—H14C0.96C33C—H33F0.96
C133—C1321.374 (5)C33B—O331.28 (2)
C133—H1330.93C33B—H33J0.93
O103—Zr01—O102141.21 (8)H12A—C12A—H12B109.5
O103—Zr01—O10187.00 (8)C114—C12A—H12C109.5
O102—Zr01—O101103.47 (9)H12A—C12A—H12C109.5
O103—Zr01—O104106.07 (8)H12B—C12A—H12C109.5
O102—Zr01—O10489.13 (8)C123—C124—C125124.9 (3)
O101—Zr01—O104141.02 (8)C123—C124—H124117.5
O103—Zr01—N10474.36 (8)C125—C124—H124117.5
O102—Zr01—N104143.99 (8)O101—C108—C107122.7 (3)
O101—Zr01—N10478.77 (9)O101—C108—C109118.3 (3)
O104—Zr01—N10470.22 (8)C107—C108—C109118.9 (3)
O103—Zr01—N10370.55 (8)C102—C103—C104120.3 (3)
O102—Zr01—N10379.49 (8)C102—C103—H103119.9
O101—Zr01—N103142.52 (8)C104—C103—H103119.9
O104—Zr01—N10375.58 (8)C123—C13A—H13A109.5
N104—Zr01—N103120.68 (9)C123—C13A—H13B109.5
O103—Zr01—N101143.46 (8)H13A—C13A—H13B109.5
O102—Zr01—N10173.70 (8)C123—C13A—H13C109.5
O101—Zr01—N10170.11 (9)H13A—C13A—H13C109.5
O104—Zr01—N10178.70 (9)H13B—C13A—H13C109.5
N104—Zr01—N10173.50 (8)C105—C106—C107125.9 (4)
N103—Zr01—N101142.84 (8)C105—C106—H106117.1
O103—Zr01—N10277.60 (8)C107—C106—H106117.1
O102—Zr01—N10269.70 (8)C107—C11B—H11A109.5
O101—Zr01—N10274.80 (8)C107—C11B—H11B109.5
O104—Zr01—N102143.28 (8)H11A—C11B—H11B109.5
N104—Zr01—N102142.11 (8)C107—C11B—H11C109.5
N103—Zr01—N10271.36 (8)H11A—C11B—H11C109.5
N101—Zr01—N102120.46 (9)H11B—C11B—H11C109.5
C110—N102—C118119.1 (3)C106—C105—C104117.3 (4)
C110—N102—Zr01128.5 (2)C106—C105—C11A122.3 (4)
C118—N102—Zr01112.45 (19)C104—C105—C11A120.3 (4)
C108—O101—Zr01124.0 (2)C125—C13B—H13D109.5
C135—O104—Zr01123.64 (18)C125—C13B—H13E109.5
C128—N104—C136118.2 (3)H13D—C13B—H13E109.5
C128—N104—Zr01127.7 (2)C125—C13B—H13F109.5
C136—N104—Zr01114.05 (18)H13D—C13B—H13F109.5
C126—O103—Zr01123.28 (17)H13E—C13B—H13F109.5
C101—N101—C109119.0 (3)C116—C12B—H12D109.5
C101—N101—Zr01128.1 (2)C116—C12B—H12E109.5
C109—N101—Zr01112.3 (2)H12D—C12B—H12E109.5
C119—N103—C127118.8 (3)C116—C12B—H12F109.5
C119—N103—Zr01128.3 (2)H12D—C12B—H12F109.5
C127—N103—Zr01112.86 (19)H12E—C12B—H12F109.5
C117—O102—Zr01124.72 (18)C132—C14A—H14D109.5
C117—C116—C115118.1 (3)C132—C14A—H14E109.5
C117—C116—C12B120.9 (3)H14D—C14A—H14E109.5
C115—C116—C12B120.9 (3)C132—C14A—H14F109.5
N104—C128—C129122.6 (3)H14D—C14A—H14F109.5
N104—C128—H128118.7H14E—C14A—H14F109.5
C129—C128—H128118.7C129—C130—C131120.3 (3)
N102—C110—C111122.7 (3)C129—C130—H130119.9
N102—C110—H110118.7C131—C130—H130119.9
C111—C110—H110118.7C124—C123—C122117.3 (3)
C127—C122—C121116.4 (3)C124—C123—C13A122.5 (3)
C127—C122—C123118.5 (3)C122—C123—C13A120.1 (3)
C121—C122—C123125.1 (3)C133—C132—C131117.6 (3)
C108—C107—C106116.8 (3)C133—C132—C14A121.8 (4)
C108—C107—C11B119.8 (3)C131—C132—C14A120.6 (3)
C106—C107—C11B123.4 (3)C105—C11A—H11D109.5
C126—C125—C124118.4 (3)C105—C11A—H11E109.5
C126—C125—C13B120.1 (3)H11D—C11A—H11E109.5
C124—C125—C13B121.4 (3)C105—C11A—H11F109.5
C120—C121—C122120.3 (3)H11D—C11A—H11F109.5
C120—C121—H121119.8H11E—C11A—H11F109.5
C122—C121—H121119.8C201—N201—C203126.3 (6)
N102—C118—C117115.5 (3)C201—N201—C202118.9 (5)
N102—C118—C113122.5 (3)C203—N201—C202114.9 (5)
C117—C118—C113122.0 (3)N201—C202—H20A109.5
C112—C111—C110119.0 (3)N201—C202—H20B109.5
C112—C111—H111120.5H20A—C202—H20B109.5
C110—C111—H111120.5N201—C202—H20C109.5
N101—C109—C104122.8 (3)H20A—C202—H20C109.5
N101—C109—C108114.6 (3)H20B—C202—H20C109.5
C104—C109—C108122.5 (3)N201—C203—H20D109.5
C121—C120—C119119.0 (3)N201—C203—H20E109.5
C121—C120—H120120.5H20D—C203—H20E109.5
C119—C120—H120120.5N201—C203—H20F109.5
C115—C114—C113116.5 (3)H20D—C203—H20F109.5
C115—C114—C12A122.9 (3)H20E—C203—H20F109.5
C113—C114—C12A120.5 (3)O201—C201—N201132.4 (7)
O102—C117—C116124.3 (3)O201—C201—H201113.8
O102—C117—C118116.9 (3)N201—C201—H201113.8
C116—C117—C118118.8 (3)C31B—N31—C31C129 (2)
C130—C129—C128119.5 (3)C31B—N31—C31A118.4 (19)
C130—C129—H129120.2C31C—N31—C31A113.1 (16)
C128—C129—H129120.2N31—C31A—H31A109.5
N103—C119—C120122.7 (3)N31—C31A—H31B109.5
N103—C119—H119118.6H31A—C31A—H31B109.5
C120—C119—H119118.6N31—C31A—H31C109.5
C135—C134—C133117.8 (3)H31A—C31A—H31C109.5
C135—C134—C14B121.3 (3)H31B—C31A—H31C109.5
C133—C134—C14B120.9 (3)N31—C31B—H31D109.5
N103—C127—C122122.7 (3)N31—C31B—H31E109.5
N103—C127—C126114.9 (3)H31D—C31B—H31E109.5
C122—C127—C126122.4 (3)N31—C31B—H31F109.5
O104—C135—C134124.0 (3)H31D—C31B—H31F109.5
O104—C135—C136117.2 (3)H31E—C31B—H31F109.5
C134—C135—C136118.8 (3)O31—C31C—N31106.0 (18)
C132—C131—C136119.0 (3)O31—C31C—H31J127
C132—C131—C130124.7 (3)N31—C31C—H31J127
C136—C131—C130116.3 (3)C32C—N32—C32A118.3 (18)
C111—C112—C113120.4 (4)C32C—N32—C32B117.8 (19)
C111—C112—H112119.8C32A—N32—C32B123.9 (19)
C113—C112—H112119.8N32—C32B—H32A109.5
C114—C115—C116125.5 (3)N32—C32B—H32B109.5
C114—C115—H115117.2H32A—C32B—H32B109.5
C116—C115—H115117.2N32—C32B—H32C109.5
N101—C101—C102122.0 (3)H32A—C32B—H32C109.5
N101—C101—H101119H32B—C32B—H32C109.5
C102—C101—H101119N32—C32C—H32D109.5
C112—C113—C114124.7 (3)N32—C32C—H32E109.5
C112—C113—C118116.3 (3)H32D—C32C—H32E109.5
C114—C113—C118118.9 (3)N32—C32C—H32F109.5
C103—C102—C101119.5 (3)H32D—C32C—H32F109.5
C103—C102—H102120.3H32E—C32C—H32F109.5
C101—C102—H102120.3O32—C32A—N32121 (3)
C109—C104—C103116.4 (3)O32—C32A—H32J119.4
C109—C104—C105118.5 (4)N32—C32A—H32J119.4
C103—C104—C105125.1 (3)C33B—N33—C33C126.8 (17)
N104—C136—C131123.2 (3)C33B—N33—C33A124.9 (17)
N104—C136—C135114.8 (3)C33C—N33—C33A107.1 (14)
C131—C136—C135122.0 (3)N33—C33A—H33A109.5
C134—C14B—H14A109.5N33—C33A—H33B109.5
C134—C14B—H14B109.5H33A—C33A—H33B109.5
H14A—C14B—H14B109.5N33—C33A—H33C109.5
C134—C14B—H14C109.5H33A—C33A—H33C109.5
H14A—C14B—H14C109.5H33B—C33A—H33C109.5
H14B—C14B—H14C109.5N33—C33C—H33D109.5
C132—C133—C134124.8 (4)N33—C33C—H33E109.5
C132—C133—H133117.6H33D—C33C—H33E109.5
C134—C133—H133117.6N33—C33C—H33F109.5
O103—C126—C125124.4 (3)H33D—C33C—H33F109.5
O103—C126—C127117.3 (2)H33E—C33C—H33F109.5
C125—C126—C127118.3 (3)O33—C33B—N33122 (2)
C114—C12A—H12A109.5O33—C33B—H33J119.1
C114—C12A—H12B109.5N33—C33B—H33J119.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14A—H14E···O201i0.962.433.358 (7)161
Symmetry code: (i) x+3/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formula[Zr(C11H10NO)4]·2C3H7NO
Mr926.21
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)100
a, b, c (Å)15.572 (5), 18.706 (5), 15.853 (5)
V3)4618 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.26 × 0.14 × 0.13
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.928, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
61276, 11142, 8497
Rint0.064
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.099, 1.02
No. of reflections11142
No. of parameters671
No. of restraints299
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.42, 0.39
Absolute structureFlack (1983), 5375 Friedel pairs
Absolute structure parameter0.01 (3)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14A—H14E···O201i0.962.433.358 (7)161.3
Symmetry code: (i) x+3/2, y+1/2, z1/2.
 

Acknowledgements

Financial assistance from the Advanced Metals Initiative (AMI) and the Department of Science and Technology (DST) of South Africa, as well as the New Metals Development Network (NMDN) and the South African Nuclear Energy Corporation Limited (Necsa), is gratefully acknowledged.

References

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Volume 68| Part 11| November 2012| Pages m1344-m1345
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