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The title compound, [Zr(Cl)2(C21H25N2)(C9H7)]·0.5C7H8, [bis­(2,6-dimethyl­phen­yl)nacnac](inden­yl)ZrCl2, where nacnac is the pentane-2,4-diiminate ligand, has pseudo-tetra­hedral coordination geometry about the Zr center. The coordination mode of the nacnac ligand is inter­mediate between η2- and η5-coordination, with both N atoms and two C atoms clearly coordinated to the Zr center. The coordination is best described as an in-plane η1-imine and η3-enaminato coordination of the nacnac ligand. A toluene solvent mol­ecule is present and is disordered about a twofold crystallographic axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043966/gg2042sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043966/gg2042Isup2.hkl
Contains datablock I

CCDC reference: 663602

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.032
  • wR factor = 0.086
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.70 Ratio PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 42
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound was synthesized by ligand metathesis starting from [bis(2,6-dimethylphenyl)nacnac]ZrCl3(THF) ("nacnac" = pentane-2,4-diiminato) and indenyl lithium. Layering of a toluene solution with hexane yielded crystals in sufficient quality for X-ray analysis.

Coordination of the nacnac ligand to group 4 metals differs strongly depending on the compound composition, the nature of the nacnac ligand and the metal center. An in-plane η2-coordination is often observed in octahedral coordinated compounds (Kakaliou et al., 1999; Qian et al.; 1999; Jin & Novak, 2000; Franceschini et al., 2003; Hamaki et al., 2006). With sterically less encumbered nacnac ligands, such as N,N'-diphenyl nacnac, and in particular in the presence of a second, η5-coordinated ligand such as cyclopentadienyl or indenyl, a cyclopentadienyl-like η5-coordination has been observed (Rahim et al., 1998; Vollmerhaus et al., 2000). One example of such is (Ind)(N,N'-diphenyl-nacnac)ZrCl2, which differs from the title compound (I) only by the lack of the 2,6-methyl substituents on the N-bonded phenyl rings (Rahim et al., 1998).

In contrast to these, the nacnac ligand adopts in (I), an intermediate, distorted coordination mode. The coordination of N1 and the carbon atoms C2 and C3 can be described as an η3-coordinated enamide, as evidenced by Zr—C distances of 2.617 (2) and 2.616 (2) Å, respectively, and an angle (C1,C2,Zr) of 140.7 (2)°. The Zr—C4 distance of 2.825 (2) Å, however, is significantly elongated in comparison to C2 and C3 and the methyl substituent at C4 is orientated away from the metal center with a bond angle (C5,C4,Zr) of 169.5 (2)°, indicating that the N lone pair, but not the CN-bond is coordinated to the Zr center. (While we cannot completely exclude a π-coordination of C4 to the metal, the elongated Zr—C4 distance makes this improbable.) The coordination of the nacnac ligand can be thus broken down into two parts, an η3-enaminato coordination of C2, C3 and N1 and an η1-imine coordination of C4 and N2.

The planar coordination of the enaminato-moiety and the in-plane coordination of the imine-moiety results in a folding of the ligand backbone, which reduces its electron delocalization. The least-square planes through N1, C1–C3 and N2, C3–C5 display an angle of 41°. Bond distances observed in the ligand backbone agree with a slight separation of the π-system into an enaminato- and an imine-moiety. The proposed imine bond N2C4 is shorter than the so-assigned enamine bond N1C2 (1.303 (3) and 1.352 (3) Å, respectively). The C2—C3 distance of 1.394 (3) Å is comparable to the N—C distances, while the C3—C4 distance is significantly elongated to 1.454 (3) Å and can be assigned a higher single-bond character.

The coordination of the nacnac ligand observed here differs from the earlier described η2 or η5-coordination (see above) and from those observed, for example, in scandium complexes, where a placement of the Sc center outside of the ligand plane was ascribed to steric reasons without any significant coordination of the carbon atoms to the metal center (Lee et al., 1999). A comparable coordination, however, was observed for the nacnac ligand in the five-coordinated complexes reported by Basuli et al. (2004) (CSD-codes: FAPBUU, FAPCAP, FAPCEF & FABCIJ). Their coordination was described simply as "sandwich-like". Not surprisingly, the analogous compound in which indenyl is replaced by cyclopentadienyl is nearly isostructural (Verguet et al., 2007).

The indenyl ligand displays only a very slight deviation from ideal η5-coordination (ΔM–C = 0.11 Å and Ω = 4°˛ Faller et al., 1985).

Related literature top

For a related mixed (indenyl)(nacnac)ZrCl2 compound, see Rahim et al. (1998). For the analogous cyclopentadienyl compound, see Verguet et al. (2007). For comparable coordination of the nacnac ligand in five-coordinated complexes, see Basuli et al. (2004) [Cambridge Structural Database (Allen, 2002) refcodes FAPBUU, FAPCAP, FAPCEF and FABCIJ]. For Zr complexes containing η2-coordinated nacnac, see: Kakaliou et al. (1999); Qian et al. (1999); Jin & Novak (2000); Franceschini et al. (2003); Hamaki et al. (2006). For Zr complexes containing η5-like coordinated nacnac, see: Rahim et al. (1998); Vollmerhaus et al. (2000). For related literature, see: Faller et al. (1985); Fortuné et al. (2007); Lee et al. (1999).

Experimental top

All operations were carried out under N2 atmosphere. Solvents have been dried by standard methods and de-oxygenized.

30 ml of toluene were added to a mixture of 0.5 g (0.87 mmol) (nacnac)ZrCl3(THF) (Fortuné et al., 2007) and 0.115 g indenyl lithium (0.96 mmol). After two days of stirring at room temperature, the obtained suspension is filtered and the precipitate washed with 8 ml of toluene. The volume of the combined filtrates was reduced to ca 10 ml and layered with 10 ml of hexane. After two weeks the product was isolated by decantation of the solvent as yellow microcrystals, 0.213 g (42%).

NMR 1H (300 MHz, C6D6), δ p.p.m.: 7.13–7.30 (m), 6.70 (br s, 1H), 6.46 (br s, 2H), 5.67 (s, 1H), 2.63 (s, 6H), 2.07 (s, 6H), 1.97 (s, 6H).

Refinement top

The H atoms were generated geometrically (C—H 0.93 to 0.98, N—H 0.86 and O—H 0.82 Å) and were included in the refinement in the riding model approximation, their temperature factors were set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others.

Structure description top

The title compound was synthesized by ligand metathesis starting from [bis(2,6-dimethylphenyl)nacnac]ZrCl3(THF) ("nacnac" = pentane-2,4-diiminato) and indenyl lithium. Layering of a toluene solution with hexane yielded crystals in sufficient quality for X-ray analysis.

Coordination of the nacnac ligand to group 4 metals differs strongly depending on the compound composition, the nature of the nacnac ligand and the metal center. An in-plane η2-coordination is often observed in octahedral coordinated compounds (Kakaliou et al., 1999; Qian et al.; 1999; Jin & Novak, 2000; Franceschini et al., 2003; Hamaki et al., 2006). With sterically less encumbered nacnac ligands, such as N,N'-diphenyl nacnac, and in particular in the presence of a second, η5-coordinated ligand such as cyclopentadienyl or indenyl, a cyclopentadienyl-like η5-coordination has been observed (Rahim et al., 1998; Vollmerhaus et al., 2000). One example of such is (Ind)(N,N'-diphenyl-nacnac)ZrCl2, which differs from the title compound (I) only by the lack of the 2,6-methyl substituents on the N-bonded phenyl rings (Rahim et al., 1998).

In contrast to these, the nacnac ligand adopts in (I), an intermediate, distorted coordination mode. The coordination of N1 and the carbon atoms C2 and C3 can be described as an η3-coordinated enamide, as evidenced by Zr—C distances of 2.617 (2) and 2.616 (2) Å, respectively, and an angle (C1,C2,Zr) of 140.7 (2)°. The Zr—C4 distance of 2.825 (2) Å, however, is significantly elongated in comparison to C2 and C3 and the methyl substituent at C4 is orientated away from the metal center with a bond angle (C5,C4,Zr) of 169.5 (2)°, indicating that the N lone pair, but not the CN-bond is coordinated to the Zr center. (While we cannot completely exclude a π-coordination of C4 to the metal, the elongated Zr—C4 distance makes this improbable.) The coordination of the nacnac ligand can be thus broken down into two parts, an η3-enaminato coordination of C2, C3 and N1 and an η1-imine coordination of C4 and N2.

The planar coordination of the enaminato-moiety and the in-plane coordination of the imine-moiety results in a folding of the ligand backbone, which reduces its electron delocalization. The least-square planes through N1, C1–C3 and N2, C3–C5 display an angle of 41°. Bond distances observed in the ligand backbone agree with a slight separation of the π-system into an enaminato- and an imine-moiety. The proposed imine bond N2C4 is shorter than the so-assigned enamine bond N1C2 (1.303 (3) and 1.352 (3) Å, respectively). The C2—C3 distance of 1.394 (3) Å is comparable to the N—C distances, while the C3—C4 distance is significantly elongated to 1.454 (3) Å and can be assigned a higher single-bond character.

The coordination of the nacnac ligand observed here differs from the earlier described η2 or η5-coordination (see above) and from those observed, for example, in scandium complexes, where a placement of the Sc center outside of the ligand plane was ascribed to steric reasons without any significant coordination of the carbon atoms to the metal center (Lee et al., 1999). A comparable coordination, however, was observed for the nacnac ligand in the five-coordinated complexes reported by Basuli et al. (2004) (CSD-codes: FAPBUU, FAPCAP, FAPCEF & FABCIJ). Their coordination was described simply as "sandwich-like". Not surprisingly, the analogous compound in which indenyl is replaced by cyclopentadienyl is nearly isostructural (Verguet et al., 2007).

The indenyl ligand displays only a very slight deviation from ideal η5-coordination (ΔM–C = 0.11 Å and Ω = 4°˛ Faller et al., 1985).

For a related mixed (indenyl)(nacnac)ZrCl2 compound, see Rahim et al. (1998). For the analogous cyclopentadienyl compound, see Verguet et al. (2007). For comparable coordination of the nacnac ligand in five-coordinated complexes, see Basuli et al. (2004) [Cambridge Structural Database (Allen, 2002) refcodes FAPBUU, FAPCAP, FAPCEF and FABCIJ]. For Zr complexes containing η2-coordinated nacnac, see: Kakaliou et al. (1999); Qian et al. (1999); Jin & Novak (2000); Franceschini et al. (2003); Hamaki et al. (2006). For Zr complexes containing η5-like coordinated nacnac, see: Rahim et al. (1998); Vollmerhaus et al. (2000). For related literature, see: Faller et al. (1985); Fortuné et al. (2007); Lee et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound (I). Displacement ellipsoids are shown at 50% probability levels. Hydrogen atoms and the solvent molecule are omitted for clarity.
Dichlorido-[N,N'-bis(2,6-dimethylphenyl)pentane-2,4- diiminato](indenyl)zirconium(IV) toluene hemisolvate top
Crystal data top
[Zr(Cl)2(C21H25N2)(C9H7)]·0.5C7H8F(000) = 2600
Mr = 628.77Dx = 1.395 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2ycCell parameters from 16709 reflections
a = 25.6719 (7) Åθ = 4.1–71.5°
b = 12.2509 (3) ŵ = 4.83 mm1
c = 22.6278 (6) ÅT = 150 K
β = 122.701 (1)°Hexagonal prism, yellow
V = 5988.6 (3) Å30.27 × 0.21 × 0.18 mm
Z = 8
Data collection top
Bruker SMART 6000
diffractometer
5814 independent reflections
Radiation source: Rotating Anode5182 reflections with I > 2σ(I)
Montel 200 optics monochromatorRint = 0.036
Detector resolution: 5.5 pixels mm-1θmax = 71.8°, θmin = 4.1°
ω scansh = 3131
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)
k = 1514
Tmin = 0.322, Tmax = 0.419l = 2727
36248 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.00 w 1 /[σ2(Fo2) + (0.0655P)2]
where P = (Fo2 + 2Fc2)/3
5814 reflections(Δ/σ)max = 0.003
380 parametersΔρmax = 0.48 e Å3
42 restraintsΔρmin = 0.99 e Å3
Crystal data top
[Zr(Cl)2(C21H25N2)(C9H7)]·0.5C7H8V = 5988.6 (3) Å3
Mr = 628.77Z = 8
Monoclinic, C2/cCu Kα radiation
a = 25.6719 (7) ŵ = 4.83 mm1
b = 12.2509 (3) ÅT = 150 K
c = 22.6278 (6) Å0.27 × 0.21 × 0.18 mm
β = 122.701 (1)°
Data collection top
Bruker SMART 6000
diffractometer
5814 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)
5182 reflections with I > 2σ(I)
Tmin = 0.322, Tmax = 0.419Rint = 0.036
36248 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03242 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.00Δρmax = 0.48 e Å3
5814 reflectionsΔρmin = 0.99 e Å3
380 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. Half a molecule of toluene cocrystallized with the compound. The toluene was found disordered around a C2 axis. The disorder was resolved and the molecule refined isotropically with half occupancy and strong SIMU restraints.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zr0.143188 (7)0.483751 (13)0.008416 (9)0.01843 (7)
Cl10.03687 (2)0.47259 (4)0.09714 (3)0.02579 (12)
Cl20.12545 (3)0.68593 (4)0.00659 (3)0.03025 (13)
N10.19716 (8)0.51001 (13)0.12184 (9)0.0207 (4)
N20.11907 (8)0.32659 (13)0.04335 (9)0.0204 (3)
C10.14769 (10)0.64130 (18)0.16091 (12)0.0303 (5)
H1A0.17930.63290.21100.045*
H1B0.10710.65110.15460.045*
H1C0.15730.70530.14250.045*
C20.14666 (10)0.54086 (17)0.12195 (11)0.0213 (4)
C30.09133 (10)0.48371 (16)0.08108 (12)0.0226 (4)
H30.05180.52510.06170.027*
C40.08729 (9)0.36697 (17)0.06765 (11)0.0221 (4)
C50.04803 (11)0.30251 (18)0.08539 (14)0.0323 (5)
H5A0.04960.22510.07560.048*
H5B0.00520.32840.05700.048*
H5C0.06360.31180.13530.048*
C60.25771 (10)0.52759 (17)0.18412 (12)0.0242 (4)
C70.27341 (11)0.46406 (18)0.24365 (12)0.0277 (5)
C80.33397 (12)0.4680 (2)0.30195 (13)0.0358 (6)
H80.34550.42290.34140.043*
C90.37739 (12)0.5363 (2)0.30332 (14)0.0419 (6)
H90.41870.53670.34300.050*
C100.36058 (10)0.6040 (2)0.24692 (13)0.0391 (6)
H100.39020.65330.24930.047*
C110.30077 (10)0.60146 (19)0.18634 (12)0.0290 (5)
C120.22623 (11)0.3966 (2)0.24793 (12)0.0324 (5)
H12A0.24730.33780.28220.049*
H12B0.19660.36510.20170.049*
H12C0.20420.44320.26260.049*
C130.28577 (11)0.6822 (2)0.12911 (14)0.0358 (5)
H13A0.29970.75510.14960.054*
H13B0.24100.68330.09500.054*
H13C0.30690.66080.10550.054*
C140.12040 (10)0.21030 (16)0.03269 (11)0.0232 (4)
C150.17576 (10)0.15317 (17)0.07763 (11)0.0238 (4)
C160.17834 (12)0.04197 (19)0.06504 (13)0.0295 (5)
H160.21570.00280.09420.035*
C170.12726 (14)0.01187 (19)0.01081 (15)0.0387 (6)
H170.12980.08710.00260.046*
C180.07303 (12)0.0442 (2)0.03091 (14)0.0380 (6)
H180.03780.00630.06690.046*
C190.06834 (11)0.15637 (18)0.02168 (13)0.0307 (5)
C200.23056 (10)0.20341 (18)0.14176 (12)0.0283 (5)
H20A0.22900.18600.18310.042*
H20B0.22960.28280.13590.042*
H20C0.26880.17420.14810.042*
C210.00696 (12)0.2117 (2)0.07102 (15)0.0465 (7)
H21A0.01190.29090.06410.070*
H21B0.02380.18580.06130.070*
H21C0.00690.19420.11970.070*
C220.24844 (10)0.45664 (19)0.03229 (12)0.0273 (5)
H220.28280.47090.07840.033*
C230.21781 (10)0.35619 (17)0.00798 (12)0.0252 (4)
H230.22610.29220.03540.030*
C240.17205 (10)0.36687 (18)0.06511 (11)0.0244 (4)
C250.13063 (11)0.29092 (19)0.11733 (13)0.0309 (5)
H250.12870.21740.10540.037*
C260.09397 (12)0.3268 (2)0.18478 (14)0.0383 (6)
H260.06670.27670.22020.046*
C270.09525 (12)0.4366 (2)0.20382 (13)0.0381 (6)
H270.06890.45820.25150.046*
C280.13362 (12)0.5117 (2)0.15509 (13)0.0316 (5)
H280.13370.58530.16820.038*
C290.17358 (11)0.47757 (17)0.08417 (12)0.0250 (5)
C300.21977 (10)0.53284 (16)0.02299 (12)0.0265 (5)
H300.22970.60820.01980.032*
C310.50653 (10)0.57281 (16)0.26223 (12)0.0489 (14)0.50
C320.47229 (10)0.61465 (16)0.19443 (12)0.051 (2)0.50
H320.45400.56580.15570.062*0.50
C330.4645 (5)0.7226 (9)0.1824 (5)0.056 (3)0.50
H330.43870.74870.13570.067*0.50
C340.4928 (5)0.7944 (6)0.2360 (4)0.047 (2)0.50
H340.48880.87060.22660.057*0.50
C350.5272 (4)0.7581 (6)0.3039 (5)0.0307 (17)0.50
H350.54520.80910.34150.037*0.50
C360.5356 (3)0.6497 (6)0.3179 (4)0.0341 (14)0.50
H360.56110.62510.36500.041*0.50
C370.5191 (5)0.4517 (6)0.2769 (5)0.091 (3)0.50
H37A0.48730.41910.28270.137*0.50
H37B0.55990.44110.32000.137*0.50
H37C0.51830.41650.23750.137*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zr0.01806 (11)0.01647 (11)0.02401 (11)0.00228 (6)0.01350 (8)0.00109 (6)
Cl10.0198 (2)0.0313 (3)0.0267 (3)0.00414 (19)0.0128 (2)0.00094 (19)
Cl20.0332 (3)0.0180 (2)0.0404 (3)0.0040 (2)0.0205 (2)0.0020 (2)
N10.0185 (8)0.0204 (8)0.0241 (9)0.0002 (7)0.0121 (7)0.0022 (7)
N20.0178 (8)0.0164 (8)0.0266 (9)0.0010 (6)0.0117 (7)0.0013 (6)
C10.0284 (11)0.0281 (11)0.0362 (12)0.0015 (9)0.0187 (10)0.0098 (9)
C20.0225 (10)0.0197 (9)0.0253 (10)0.0032 (8)0.0154 (8)0.0010 (8)
C30.0224 (11)0.0197 (10)0.0308 (11)0.0019 (8)0.0177 (9)0.0018 (8)
C40.0167 (9)0.0206 (10)0.0284 (10)0.0019 (8)0.0119 (8)0.0004 (8)
C50.0314 (12)0.0254 (11)0.0514 (15)0.0005 (9)0.0299 (11)0.0002 (10)
C60.0204 (10)0.0254 (11)0.0282 (11)0.0012 (8)0.0140 (9)0.0066 (8)
C70.0267 (11)0.0291 (11)0.0277 (11)0.0054 (9)0.0149 (10)0.0051 (9)
C80.0308 (13)0.0418 (14)0.0290 (12)0.0090 (11)0.0122 (10)0.0049 (10)
C90.0233 (12)0.0507 (16)0.0379 (14)0.0031 (11)0.0076 (10)0.0112 (12)
C100.0233 (12)0.0450 (15)0.0452 (15)0.0065 (11)0.0160 (11)0.0149 (12)
C110.0235 (10)0.0310 (11)0.0349 (12)0.0034 (9)0.0175 (10)0.0096 (9)
C120.0355 (12)0.0351 (12)0.0294 (11)0.0058 (10)0.0194 (10)0.0028 (10)
C130.0324 (12)0.0359 (13)0.0433 (14)0.0128 (10)0.0232 (11)0.0089 (11)
C140.0247 (10)0.0171 (9)0.0308 (11)0.0010 (8)0.0169 (9)0.0021 (8)
C150.0269 (10)0.0222 (10)0.0294 (11)0.0043 (9)0.0199 (9)0.0031 (8)
C160.0388 (13)0.0233 (10)0.0379 (13)0.0081 (10)0.0282 (11)0.0047 (9)
C170.0564 (17)0.0199 (11)0.0538 (17)0.0012 (11)0.0389 (15)0.0034 (10)
C180.0416 (14)0.0249 (11)0.0466 (15)0.0080 (11)0.0233 (12)0.0125 (11)
C190.0279 (11)0.0230 (11)0.0376 (12)0.0006 (9)0.0153 (10)0.0042 (9)
C200.0261 (11)0.0308 (11)0.0292 (11)0.0075 (9)0.0156 (9)0.0037 (9)
C210.0266 (12)0.0334 (13)0.0524 (16)0.0044 (11)0.0036 (11)0.0094 (12)
C220.0208 (10)0.0353 (12)0.0315 (11)0.0038 (9)0.0177 (9)0.0025 (9)
C230.0259 (10)0.0252 (10)0.0329 (11)0.0072 (9)0.0215 (9)0.0000 (9)
C240.0241 (10)0.0262 (11)0.0313 (11)0.0037 (9)0.0204 (9)0.0020 (9)
C250.0313 (11)0.0290 (11)0.0419 (13)0.0001 (10)0.0259 (11)0.0074 (10)
C260.0308 (12)0.0481 (15)0.0394 (14)0.0040 (11)0.0212 (11)0.0168 (11)
C270.0342 (13)0.0554 (16)0.0285 (12)0.0078 (12)0.0194 (11)0.0007 (11)
C280.0327 (13)0.0357 (12)0.0351 (13)0.0073 (10)0.0240 (11)0.0058 (10)
C290.0250 (11)0.0274 (11)0.0319 (12)0.0039 (8)0.0214 (10)0.0000 (8)
C300.0260 (11)0.0267 (11)0.0350 (12)0.0004 (9)0.0219 (10)0.0026 (9)
C310.071 (3)0.033 (2)0.067 (4)0.014 (3)0.053 (3)0.012 (3)
C320.051 (4)0.073 (6)0.038 (3)0.025 (4)0.030 (3)0.027 (4)
C330.041 (4)0.084 (7)0.031 (4)0.001 (6)0.012 (3)0.011 (5)
C340.035 (5)0.055 (3)0.044 (7)0.012 (4)0.016 (5)0.028 (3)
C350.034 (4)0.022 (3)0.038 (5)0.003 (2)0.020 (4)0.006 (2)
C360.039 (3)0.023 (3)0.036 (3)0.008 (2)0.017 (2)0.004 (2)
C370.122 (7)0.043 (3)0.130 (7)0.008 (4)0.081 (6)0.007 (4)
Geometric parameters (Å, º) top
Zr—N12.1836 (18)C15—C201.503 (3)
Zr—N22.2900 (17)C16—C171.386 (4)
Zr—C222.475 (2)C16—H160.9500
Zr—Cl12.4758 (5)C17—C181.372 (4)
Zr—C232.4763 (19)C17—H170.9500
Zr—C302.498 (2)C18—C191.404 (3)
Zr—Cl22.5081 (5)C18—H180.9500
Zr—C242.588 (2)C19—C211.513 (3)
Zr—C292.602 (2)C20—H20A0.9800
Zr—C32.616 (2)C20—H20B0.9800
Zr—C22.617 (2)C20—H20C0.9800
Zr—C42.825 (2)C21—H21A0.9800
N1—C21.352 (3)C21—H21B0.9800
N1—C61.443 (3)C21—H21C0.9800
N2—C41.303 (3)C22—C231.403 (3)
N2—C141.448 (2)C22—C301.408 (3)
C1—C21.506 (3)C22—H220.9500
C1—H1A0.9800C23—C241.426 (3)
C1—H1B0.9800C23—H230.9500
C1—H1C0.9800C24—C251.427 (3)
C2—C31.394 (3)C24—C291.430 (3)
C3—C41.454 (3)C25—C261.362 (4)
C3—H31.0000C25—H250.9500
C4—C51.496 (3)C26—C271.418 (4)
C5—H5A0.9800C26—H260.9500
C5—H5B0.9800C27—C281.364 (4)
C5—H5C0.9800C27—H270.9500
C6—C111.408 (3)C28—C291.422 (3)
C6—C71.413 (3)C28—H280.9500
C7—C81.394 (3)C29—C301.417 (3)
C7—C121.512 (3)C30—H300.9500
C8—C91.381 (4)C31—C321.3900
C8—H80.9500C31—C361.419 (7)
C9—C101.381 (4)C31—C371.517 (7)
C9—H90.9500C32—C331.343 (12)
C10—C111.401 (3)C32—H320.9500
C10—H100.9500C33—C341.350 (11)
C11—C131.505 (3)C33—H330.9500
C12—H12A0.9800C34—C351.368 (11)
C12—H12B0.9800C34—H340.9500
C12—H12C0.9800C35—C361.355 (9)
C13—H13A0.9800C35—H350.9500
C13—H13B0.9800C36—H360.9500
C13—H13C0.9800C37—H37A0.9800
C14—C191.400 (3)C37—H37B0.9800
C14—C151.408 (3)C37—H37C0.9800
C15—C161.401 (3)
N1—Zr—N280.58 (6)C8—C9—C10119.8 (2)
N1—Zr—C2280.71 (7)C8—C9—H9120.1
N2—Zr—C22106.18 (7)C10—C9—H9120.1
N1—Zr—Cl1144.17 (5)C9—C10—C11121.4 (2)
N2—Zr—Cl185.63 (4)C9—C10—H10119.3
C22—Zr—Cl1135.05 (5)C11—C10—H10119.3
N1—Zr—C2395.55 (7)C10—C11—C6118.2 (2)
N2—Zr—C2379.91 (7)C10—C11—C13117.6 (2)
C22—Zr—C2332.92 (7)C6—C11—C13124.1 (2)
Cl1—Zr—C23114.41 (5)C7—C12—H12A109.5
N1—Zr—C30101.64 (7)C7—C12—H12B109.5
N2—Zr—C30134.56 (6)H12A—C12—H12B109.5
C22—Zr—C3032.89 (7)C7—C12—H12C109.5
Cl1—Zr—C30111.45 (5)H12A—C12—H12C109.5
C23—Zr—C3054.65 (7)H12B—C12—H12C109.5
N1—Zr—Cl288.12 (5)C11—C13—H13A109.5
N2—Zr—Cl2144.48 (4)C11—C13—H13B109.5
C22—Zr—Cl2105.01 (6)H13A—C13—H13B109.5
Cl1—Zr—Cl284.204 (18)C11—C13—H13C109.5
C23—Zr—Cl2134.99 (5)H13A—C13—H13C109.5
C30—Zr—Cl280.62 (5)H13B—C13—H13C109.5
N1—Zr—C24128.09 (7)C19—C14—C15120.80 (19)
N2—Zr—C2488.94 (6)C19—C14—N2120.89 (19)
C22—Zr—C2453.71 (7)C15—C14—N2118.30 (19)
Cl1—Zr—C2484.18 (5)C16—C15—C14118.5 (2)
C23—Zr—C2432.61 (7)C16—C15—C20118.2 (2)
C30—Zr—C2453.68 (7)C14—C15—C20123.16 (19)
Cl2—Zr—C24123.60 (5)C17—C16—C15121.1 (2)
N1—Zr—C29132.44 (7)C17—C16—H16119.4
N2—Zr—C29120.54 (6)C15—C16—H16119.4
C22—Zr—C2953.48 (7)C18—C17—C16119.6 (2)
Cl1—Zr—C2982.85 (5)C18—C17—H17120.2
C23—Zr—C2953.80 (7)C16—C17—H17120.2
C30—Zr—C2932.18 (7)C17—C18—C19121.6 (2)
Cl2—Zr—C2991.79 (5)C17—C18—H18119.2
C24—Zr—C2931.99 (6)C19—C18—H18119.2
N1—Zr—C358.43 (7)C14—C19—C18118.3 (2)
N2—Zr—C357.21 (6)C14—C19—C21123.8 (2)
C22—Zr—C3136.82 (7)C18—C19—C21117.9 (2)
Cl1—Zr—C386.34 (5)C15—C20—H20A109.5
C23—Zr—C3131.29 (7)C15—C20—H20B109.5
C30—Zr—C3157.65 (7)H20A—C20—H20B109.5
Cl2—Zr—C388.19 (4)C15—C20—H20C109.5
C24—Zr—C3145.45 (6)H20A—C20—H20C109.5
C29—Zr—C3169.13 (7)H20B—C20—H20C109.5
N1—Zr—C231.06 (6)C19—C21—H21A109.5
N2—Zr—C276.00 (6)C19—C21—H21B109.5
C22—Zr—C2111.56 (7)H21A—C21—H21B109.5
Cl1—Zr—C2113.38 (5)C19—C21—H21C109.5
C23—Zr—C2123.81 (7)H21A—C21—H21C109.5
C30—Zr—C2126.88 (7)H21B—C21—H21C109.5
Cl2—Zr—C277.08 (5)C23—C22—C30108.7 (2)
C24—Zr—C2155.38 (7)C23—C22—Zr73.59 (12)
C29—Zr—C2158.77 (7)C30—C22—Zr74.47 (12)
C3—Zr—C230.90 (6)C23—C22—H22125.7
N1—Zr—C471.30 (6)C30—C22—H22125.7
N2—Zr—C427.01 (6)Zr—C22—H22118.2
C22—Zr—C4127.08 (7)C22—C23—C24108.1 (2)
Cl1—Zr—C481.48 (4)C22—C23—Zr73.49 (12)
C23—Zr—C4105.94 (7)C24—C23—Zr78.02 (12)
C30—Zr—C4159.45 (6)C22—C23—H23126.0
Cl2—Zr—C4117.57 (4)C24—C23—H23126.0
C24—Zr—C4114.83 (7)Zr—C23—H23114.8
C29—Zr—C4144.83 (6)C23—C24—C25132.8 (2)
C3—Zr—C430.70 (6)C23—C24—C29107.3 (2)
C2—Zr—C454.99 (6)C25—C24—C29119.9 (2)
C2—N1—C6119.00 (18)C23—C24—Zr69.37 (11)
C2—N1—Zr92.48 (13)C25—C24—Zr123.30 (14)
C6—N1—Zr146.58 (14)C29—C24—Zr74.52 (12)
C4—N2—C14121.34 (17)C26—C25—C24118.2 (2)
C4—N2—Zr100.03 (13)C26—C25—H25120.9
C14—N2—Zr137.26 (13)C24—C25—H25120.9
C2—C1—H1A109.5C25—C26—C27122.1 (2)
C2—C1—H1B109.5C25—C26—H26119.0
H1A—C1—H1B109.5C27—C26—H26119.0
C2—C1—H1C109.5C28—C27—C26121.3 (2)
H1A—C1—H1C109.5C28—C27—H27119.3
H1B—C1—H1C109.5C26—C27—H27119.3
N1—C2—C3119.52 (18)C27—C28—C29118.7 (2)
N1—C2—C1121.07 (19)C27—C28—H28120.7
C3—C2—C1119.23 (18)C29—C28—H28120.7
N1—C2—Zr56.46 (11)C30—C29—C28132.4 (2)
C3—C2—Zr74.47 (12)C30—C29—C24107.7 (2)
C1—C2—Zr140.69 (15)C28—C29—C24119.9 (2)
C2—C3—C4124.38 (19)C30—C29—Zr69.89 (12)
C2—C3—Zr74.62 (12)C28—C29—Zr123.55 (15)
C4—C3—Zr82.64 (12)C24—C29—Zr73.49 (12)
C2—C3—H3117.8C22—C30—C29108.12 (18)
C4—C3—H3117.8C22—C30—Zr72.64 (12)
Zr—C3—H3117.8C29—C30—Zr77.93 (12)
N2—C4—C3118.12 (19)C22—C30—H30125.9
N2—C4—C5125.40 (19)C29—C30—H30125.9
C3—C4—C5116.45 (18)Zr—C30—H30115.6
N2—C4—Zr52.96 (11)C32—C31—C36116.8 (3)
C3—C4—Zr66.66 (12)C32—C31—C37122.4 (4)
C5—C4—Zr169.51 (15)C36—C31—C37120.5 (5)
C4—C5—H5A109.5C33—C32—C31121.5 (4)
C4—C5—H5B109.5C33—C32—H32119.3
H5A—C5—H5B109.5C31—C32—H32119.3
C4—C5—H5C109.5C32—C33—C34120.8 (8)
H5A—C5—H5C109.5C32—C33—H33119.6
H5B—C5—H5C109.5C34—C33—H33119.6
C11—C6—C7120.4 (2)C33—C34—C35120.3 (6)
C11—C6—N1122.8 (2)C33—C34—H34119.9
C7—C6—N1116.81 (19)C35—C34—H34119.9
C8—C7—C6118.8 (2)C36—C35—C34120.4 (9)
C8—C7—C12118.7 (2)C36—C35—H35119.8
C6—C7—C12122.4 (2)C34—C35—H35119.8
C9—C8—C7121.1 (3)C35—C36—C31120.2 (7)
C9—C8—H8119.5C35—C36—H36119.9
C7—C8—H8119.5C31—C36—H36119.9
N2—Zr—N1—C278.47 (12)C15—C16—C17—C180.6 (4)
C22—Zr—N1—C2173.26 (13)C16—C17—C18—C192.2 (4)
Cl1—Zr—N1—C29.68 (16)C15—C14—C19—C181.0 (4)
C23—Zr—N1—C2157.25 (12)N2—C14—C19—C18177.9 (2)
C30—Zr—N1—C2147.74 (12)C15—C14—C19—C21178.7 (2)
Cl2—Zr—N1—C267.72 (12)N2—C14—C19—C212.5 (4)
C24—Zr—N1—C2159.62 (11)C17—C18—C19—C141.4 (4)
C29—Zr—N1—C2158.42 (11)C17—C18—C19—C21179.0 (3)
C3—Zr—N1—C221.32 (11)N1—Zr—C22—C23115.65 (14)
C4—Zr—N1—C252.28 (12)N2—Zr—C22—C2338.37 (14)
N2—Zr—N1—C6120.3 (2)Cl1—Zr—C22—C2361.91 (16)
C22—Zr—N1—C612.1 (2)C30—Zr—C22—C23115.34 (19)
Cl1—Zr—N1—C6170.9 (2)Cl2—Zr—C22—C23158.84 (12)
C23—Zr—N1—C641.6 (2)C24—Zr—C22—C2337.92 (12)
C30—Zr—N1—C613.5 (3)C29—Zr—C22—C2377.95 (14)
Cl2—Zr—N1—C693.5 (2)C3—Zr—C22—C2397.39 (15)
C24—Zr—N1—C639.2 (3)C2—Zr—C22—C23119.38 (13)
C29—Zr—N1—C62.8 (3)C4—Zr—C22—C2357.72 (15)
C3—Zr—N1—C6177.5 (3)N1—Zr—C22—C30129.00 (14)
C2—Zr—N1—C6161.2 (3)N2—Zr—C22—C30153.71 (12)
C4—Zr—N1—C6146.5 (3)Cl1—Zr—C22—C3053.43 (16)
N1—Zr—N2—C467.03 (13)C23—Zr—C22—C30115.34 (19)
C22—Zr—N2—C4144.41 (13)Cl2—Zr—C22—C3043.50 (13)
Cl1—Zr—N2—C479.78 (12)C24—Zr—C22—C3077.43 (14)
C23—Zr—N2—C4164.45 (14)C29—Zr—C22—C3037.39 (12)
C30—Zr—N2—C4164.14 (12)C3—Zr—C22—C30147.27 (12)
Cl2—Zr—N2—C46.12 (17)C2—Zr—C22—C30125.27 (13)
C24—Zr—N2—C4164.03 (13)C4—Zr—C22—C30173.06 (11)
C29—Zr—N2—C4158.83 (12)C30—C22—C23—C244.3 (2)
C3—Zr—N2—C48.67 (12)Zr—C22—C23—C2471.07 (14)
C2—Zr—N2—C435.63 (13)C30—C22—C23—Zr66.79 (14)
N1—Zr—N2—C14127.1 (2)N1—Zr—C23—C2263.35 (14)
C22—Zr—N2—C1449.7 (2)N2—Zr—C23—C22142.73 (14)
Cl1—Zr—N2—C1486.1 (2)Cl1—Zr—C23—C22136.81 (12)
C23—Zr—N2—C1429.7 (2)C30—Zr—C23—C2236.99 (13)
C30—Zr—N2—C1430.0 (2)Cl2—Zr—C23—C2229.53 (16)
Cl2—Zr—N2—C14159.74 (16)C24—Zr—C23—C22113.19 (19)
C24—Zr—N2—C141.8 (2)C29—Zr—C23—C2276.92 (14)
C29—Zr—N2—C147.0 (2)C3—Zr—C23—C22115.41 (14)
C3—Zr—N2—C14174.5 (2)C2—Zr—C23—C2277.25 (15)
C2—Zr—N2—C14158.5 (2)C4—Zr—C23—C22135.46 (13)
C4—Zr—N2—C14165.9 (3)N1—Zr—C23—C24176.54 (13)
C6—N1—C2—C3149.8 (2)N2—Zr—C23—C24104.08 (13)
Zr—N1—C2—C341.9 (2)C22—Zr—C23—C24113.19 (19)
C6—N1—C2—C135.1 (3)Cl1—Zr—C23—C2423.62 (14)
Zr—N1—C2—C1133.18 (18)C30—Zr—C23—C2476.19 (14)
C6—N1—C2—Zr168.3 (2)Cl2—Zr—C23—C2483.65 (14)
N2—Zr—C2—N194.99 (12)C29—Zr—C23—C2436.26 (12)
C22—Zr—C2—N17.15 (14)C3—Zr—C23—C24131.40 (12)
Cl1—Zr—C2—N1173.85 (10)C2—Zr—C23—C24169.56 (12)
C23—Zr—C2—N127.60 (15)C4—Zr—C23—C24111.35 (13)
C30—Zr—C2—N140.81 (15)C22—C23—C24—C25175.2 (2)
Cl2—Zr—C2—N1108.40 (12)Zr—C23—C24—C25116.8 (2)
C24—Zr—C2—N141.1 (2)C22—C23—C24—C292.6 (2)
C29—Zr—C2—N148.6 (2)Zr—C23—C24—C2965.43 (14)
C3—Zr—C2—N1142.91 (19)C22—C23—C24—Zr67.99 (14)
C4—Zr—C2—N1113.84 (13)N1—Zr—C24—C234.38 (16)
N1—Zr—C2—C3142.91 (19)N2—Zr—C24—C2372.77 (13)
N2—Zr—C2—C347.92 (12)C22—Zr—C24—C2338.30 (13)
C22—Zr—C2—C3150.06 (12)Cl1—Zr—C24—C23158.48 (13)
Cl1—Zr—C2—C330.93 (13)C30—Zr—C24—C2379.43 (14)
C23—Zr—C2—C3115.32 (13)Cl2—Zr—C24—C23122.44 (12)
C30—Zr—C2—C3176.27 (11)C29—Zr—C24—C23115.71 (19)
Cl2—Zr—C2—C3108.69 (12)C3—Zr—C24—C2383.63 (17)
C24—Zr—C2—C3101.77 (18)C2—Zr—C24—C2321.2 (2)
C29—Zr—C2—C3168.53 (17)C4—Zr—C24—C2380.68 (13)
C4—Zr—C2—C329.08 (11)N1—Zr—C24—C25132.76 (18)
N1—Zr—C2—C199.7 (3)N2—Zr—C24—C2555.62 (19)
N2—Zr—C2—C1165.4 (2)C22—Zr—C24—C25166.7 (2)
C22—Zr—C2—C192.5 (2)Cl1—Zr—C24—C2530.10 (18)
Cl1—Zr—C2—C186.5 (2)C23—Zr—C24—C25128.4 (3)
C23—Zr—C2—C1127.3 (2)C30—Zr—C24—C25152.2 (2)
C30—Zr—C2—C158.8 (3)Cl2—Zr—C24—C25109.17 (18)
Cl2—Zr—C2—C18.7 (2)C29—Zr—C24—C25115.9 (2)
C24—Zr—C2—C1140.8 (2)C3—Zr—C24—C2544.8 (2)
C29—Zr—C2—C151.1 (3)C2—Zr—C24—C25107.2 (2)
C3—Zr—C2—C1117.4 (3)C4—Zr—C24—C2547.7 (2)
C4—Zr—C2—C1146.5 (3)N1—Zr—C24—C29111.33 (14)
N1—C2—C3—C434.3 (3)N2—Zr—C24—C29171.53 (13)
C1—C2—C3—C4150.6 (2)C22—Zr—C24—C2977.41 (14)
Zr—C2—C3—C469.6 (2)Cl1—Zr—C24—C2985.81 (13)
N1—C2—C3—Zr35.28 (17)C23—Zr—C24—C29115.71 (19)
C1—C2—C3—Zr139.88 (19)C30—Zr—C24—C2936.28 (13)
N1—Zr—C3—C221.42 (11)Cl2—Zr—C24—C296.74 (15)
N2—Zr—C3—C2121.06 (14)C3—Zr—C24—C29160.66 (14)
C22—Zr—C3—C242.71 (16)C2—Zr—C24—C29136.88 (17)
Cl1—Zr—C3—C2151.79 (12)C4—Zr—C24—C29163.61 (12)
C23—Zr—C3—C288.54 (14)C23—C24—C25—C26176.7 (2)
C30—Zr—C3—C27.9 (2)C29—C24—C25—C260.9 (3)
Cl2—Zr—C3—C267.48 (12)Zr—C24—C25—C2691.4 (2)
C24—Zr—C3—C2134.01 (13)C24—C25—C26—C271.1 (3)
C29—Zr—C3—C2157.5 (3)C25—C26—C27—C280.1 (4)
C4—Zr—C3—C2128.76 (19)C26—C27—C28—C291.0 (4)
N1—Zr—C3—C4107.34 (13)C27—C28—C29—C30176.8 (2)
N2—Zr—C3—C47.71 (11)C27—C28—C29—C241.2 (3)
C22—Zr—C3—C486.05 (15)C27—C28—C29—Zr90.5 (2)
Cl1—Zr—C3—C479.45 (12)C23—C24—C29—C300.1 (2)
C23—Zr—C3—C440.22 (16)C25—C24—C29—C30178.21 (18)
C30—Zr—C3—C4136.62 (17)Zr—C24—C29—C3061.92 (14)
Cl2—Zr—C3—C4163.76 (12)C23—C24—C29—C28178.34 (19)
C24—Zr—C3—C45.24 (19)C25—C24—C29—C280.2 (3)
C29—Zr—C3—C473.7 (4)Zr—C24—C29—C28119.6 (2)
C2—Zr—C3—C4128.76 (19)C23—C24—C29—Zr62.03 (13)
C14—N2—C4—C3176.21 (19)C25—C24—C29—Zr119.86 (18)
Zr—N2—C4—C315.0 (2)N1—Zr—C29—C3019.93 (16)
C14—N2—C4—C51.7 (3)N2—Zr—C29—C30126.30 (12)
Zr—N2—C4—C5167.14 (19)C22—Zr—C29—C3038.26 (12)
C14—N2—C4—Zr168.8 (2)Cl1—Zr—C29—C30153.08 (12)
C2—C3—C4—N252.7 (3)C23—Zr—C29—C3079.46 (14)
Zr—C3—C4—N212.98 (18)Cl2—Zr—C29—C3069.15 (12)
C2—C3—C4—C5125.4 (2)C24—Zr—C29—C30116.46 (19)
Zr—C3—C4—C5168.95 (17)C3—Zr—C29—C30158.9 (3)
C2—C3—C4—Zr65.6 (2)C2—Zr—C29—C3011.7 (2)
N1—Zr—C4—N2106.47 (13)C4—Zr—C29—C30142.85 (12)
C22—Zr—C4—N244.47 (16)N1—Zr—C29—C28148.19 (17)
Cl1—Zr—C4—N297.14 (12)N2—Zr—C29—C28105.43 (18)
C23—Zr—C4—N215.93 (14)C22—Zr—C29—C28166.5 (2)
C30—Zr—C4—N233.7 (3)Cl1—Zr—C29—C2824.82 (18)
Cl2—Zr—C4—N2175.99 (11)C23—Zr—C29—C28152.3 (2)
C24—Zr—C4—N217.65 (15)C30—Zr—C29—C28128.3 (2)
C29—Zr—C4—N232.68 (18)Cl2—Zr—C29—C2859.11 (19)
C3—Zr—C4—N2165.6 (2)C24—Zr—C29—C28115.3 (2)
C2—Zr—C4—N2136.36 (15)C3—Zr—C29—C2830.6 (4)
N1—Zr—C4—C359.15 (12)C2—Zr—C29—C28116.6 (2)
N2—Zr—C4—C3165.6 (2)C4—Zr—C29—C2888.9 (2)
C22—Zr—C4—C3121.16 (13)N1—Zr—C29—C2496.53 (14)
Cl1—Zr—C4—C397.23 (12)N2—Zr—C29—C249.85 (15)
C23—Zr—C4—C3149.70 (13)C22—Zr—C29—C2478.19 (14)
C30—Zr—C4—C3131.9 (2)Cl1—Zr—C29—C2490.46 (13)
Cl2—Zr—C4—C318.38 (13)C23—Zr—C29—C2436.99 (12)
C24—Zr—C4—C3176.73 (12)C30—Zr—C29—C24116.46 (19)
C29—Zr—C4—C3161.69 (13)Cl2—Zr—C29—C24174.39 (12)
C2—Zr—C4—C329.27 (12)C3—Zr—C29—C2484.7 (4)
N1—Zr—C4—C5168.7 (8)C2—Zr—C29—C24128.14 (18)
N2—Zr—C4—C584.8 (8)C4—Zr—C29—C2426.39 (19)
C22—Zr—C4—C5129.3 (8)C23—C22—C30—C294.4 (2)
Cl1—Zr—C4—C512.3 (8)Zr—C22—C30—C2970.56 (15)
C23—Zr—C4—C5100.8 (8)C23—C22—C30—Zr66.21 (14)
C30—Zr—C4—C5118.5 (8)C28—C29—C30—C22175.5 (2)
Cl2—Zr—C4—C591.1 (8)C24—C29—C30—C222.7 (2)
C24—Zr—C4—C567.2 (8)Zr—C29—C30—C2266.98 (14)
C29—Zr—C4—C552.2 (8)C28—C29—C30—Zr117.6 (2)
C3—Zr—C4—C5109.5 (8)C24—C29—C30—Zr64.27 (14)
C2—Zr—C4—C5138.8 (8)N1—Zr—C30—C2251.54 (14)
C2—N1—C6—C11113.5 (2)N2—Zr—C30—C2236.65 (17)
Zr—N1—C6—C1144.9 (3)Cl1—Zr—C30—C22142.44 (12)
C2—N1—C6—C768.5 (2)C23—Zr—C30—C2237.03 (13)
Zr—N1—C6—C7133.1 (2)Cl2—Zr—C30—C22137.64 (13)
C11—C6—C7—C86.2 (3)C24—Zr—C30—C2277.53 (14)
N1—C6—C7—C8171.90 (19)C29—Zr—C30—C22113.58 (18)
C11—C6—C7—C12170.5 (2)C3—Zr—C30—C2276.7 (2)
N1—C6—C7—C1211.4 (3)C2—Zr—C30—C2271.68 (14)
C6—C7—C8—C93.0 (3)C4—Zr—C30—C2215.9 (3)
C12—C7—C8—C9173.8 (2)N1—Zr—C30—C29165.12 (12)
C7—C8—C9—C101.6 (4)N2—Zr—C30—C2976.93 (15)
C8—C9—C10—C113.1 (4)C22—Zr—C30—C29113.58 (18)
C9—C10—C11—C60.1 (3)Cl1—Zr—C30—C2928.85 (13)
C9—C10—C11—C13176.9 (2)C23—Zr—C30—C2976.56 (13)
C7—C6—C11—C104.7 (3)Cl2—Zr—C30—C29108.78 (12)
N1—C6—C11—C10173.3 (2)C24—Zr—C30—C2936.06 (11)
C7—C6—C11—C13172.1 (2)C3—Zr—C30—C29169.71 (16)
N1—C6—C11—C139.9 (3)C2—Zr—C30—C29174.74 (11)
C4—N2—C14—C1971.3 (3)C4—Zr—C30—C2997.6 (2)
Zr—N2—C14—C1992.4 (3)C36—C31—C32—C333.4 (8)
C4—N2—C14—C15109.9 (2)C37—C31—C32—C33176.3 (9)
Zr—N2—C14—C1586.5 (3)C31—C32—C33—C343.9 (14)
C19—C14—C15—C162.4 (3)C32—C33—C34—C354 (2)
N2—C14—C15—C16176.45 (19)C33—C34—C35—C363 (2)
C19—C14—C15—C20172.6 (2)C34—C35—C36—C312.9 (14)
N2—C14—C15—C208.5 (3)C32—C31—C36—C352.9 (9)
C14—C15—C16—C171.6 (3)C37—C31—C36—C35176.0 (9)
C20—C15—C16—C17173.7 (2)

Experimental details

Crystal data
Chemical formula[Zr(Cl)2(C21H25N2)(C9H7)]·0.5C7H8
Mr628.77
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)25.6719 (7), 12.2509 (3), 22.6278 (6)
β (°) 122.701 (1)
V3)5988.6 (3)
Z8
Radiation typeCu Kα
µ (mm1)4.83
Crystal size (mm)0.27 × 0.21 × 0.18
Data collection
DiffractometerBruker SMART 6000
Absorption correctionMulti-scan
(SADABS; Sheldrick,1996)
Tmin, Tmax0.322, 0.419
No. of measured, independent and
observed [I > 2σ(I)] reflections
36248, 5814, 5182
Rint0.036
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.086, 1.00
No. of reflections5814
No. of parameters380
No. of restraints42
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.99

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), UdMX (local program).

 

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