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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m864–m865.
Published online 2009 July 4. doi:  10.1107/S1600536809024544
PMCID: PMC2977319

Bis(μ-phenyl­methano­lato)bis­({4-[(E)-(4-tert-butyl­phen­yl)(2-pyrid­ylmethyl­imino)meth­yl]-3-methyl-1-phenyl-1H-pyrazol-5-olato}zinc(II))

Abstract

In the title centrosymmetric dimeric ZnII complex, [Zn2(C27H27N4O)2(C7H7O)2], the ZnII center is coordinated by two N atoms and one O atom of the ketiminate ligand and two bridging O atoms of the benzyl­alkoxy groups. The geometry around the ZnII ions is distorted trigonal-bipyramidal.

Related literature

For the potential applications of polyesters, see: Gref et al. (1994 [triangle]); Jeong et al. (1997 [triangle]). Many zinc complexes with various ligands are effective initiators/catalysts for the ring-opening polymerization (ROP) of cyclic esters, see: Chamberlain et al. (2001 [triangle]); Williams et al. (2003 [triangle]); Dechy-Cabaret et al. (2004 [triangle]); Chen et al. (2005 [triangle]); Wu et al. (2006 [triangle]); Huang et al. (2009 [triangle]); Hung et al. (2008 [triangle]). Tripodal tridentate ligand-supported zinc complexes have been used for the polymerization of lactides, see: Chisholm et al. (2000 [triangle]). Recently, a series of zinc alkoxides (Yu et al., 2002 [triangle]; Lee et al., 2007 [triangle]) coordinated with simple N,N,O-tridentate ketiminate ligands has been synthesized and these derivatives showed highly catalytic activity with regard to the ROP of lactides. For Zn—O and Zn—N distances in other zinc ketiminate complexes, see: Hung & Lin (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m864-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C27H27N4O)2(C7H7O)2]
  • M r = 1192.04
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m864-efi1.jpg
  • a = 9.0873 (15) Å
  • b = 13.363 (2) Å
  • c = 13.397 (2) Å
  • α = 72.206 (3)°
  • β = 74.018 (3)°
  • γ = 88.664 (3)°
  • V = 1485.9 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.86 mm−1
  • T = 293 K
  • 0.41 × 0.32 × 0.25 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.719, T max = 0.813
  • 8258 measured reflections
  • 5792 independent reflections
  • 4450 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.137
  • S = 1.01
  • 5792 reflections
  • 370 parameters
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024544/bt2979sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024544/bt2979Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from National Science Council of the Republic of China is gratefully appreciated. Helpful comments from the reviewers are also greatly appreciated.

supplementary crystallographic information

Comment

Polyesters such as poly(ε-caprolactone) (PCL) and poly(lactide) (PLA) and their copolymers have attracted intensive attention due to their potential applications in many fields (Gref et al.,1994; Jeong et al., 1997). The major polymerization methods for these polymers are the ring-opening polymerization (ROP) of cyclic esters. Many zinc complexes with various ligands were effective initiator/catalyst for the ROP of cyclic esters (Chamberlain et al., 2001; Williams et al., 2003; Dechy-Cabaret et al. 2004, Chen, et al., 2005; Wu, et al., 2006; Hung et al., 2008, 2009). Tripodal tridentate ligand supported zinc complexes have been synthesized and used for the polymerization of lactides and the polymerization is living with relatively low polydispersities (Chisholm et al., 2000). Recently, a series of zinc alkoxides (Yu, et al., 2002; Lee, et al., 2007) coordinated with simple NNO-tridentate ketiminate ligands has been synthesized and these derivatives showed highly catalytic activity with regard to the ROP of lactides. However, these complexes had no (or little) stereoselectivities for the polymerization of rac-lactides. In order to obtain catalytic activity as well as enhance stereoselectivity of the corresponding metal alkoxides, we (Huang, et al., 2009) have developed a unsymmetric NNO-ketiminate system derived from 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one. In the presence of pyrazole fused a chelating arm, the metal derivatives can be stabilized by an extensive π-conjugate system. In this study, we reported the synthesis and crystal structure of [LZn(µ-OBn)]2, where L and benzyloxy are the NNO-tridentate ketiminate ligand and benzylalkoxy group, respectively.

This solid structure of [LZn(µ-OBn)]2 reveals a dimeric ZnII complex in which the zinc center is coordinated to N,N,O atoms of the ketiminate ligand and two bridging oxygen atoms of the benzylalkoxy groups. The geometry around the zinc ion is a distorted trigonal bipyramid with τ = 0.51 and atoms O(1), O(2), and N(3) sitting on the equatorial positions. The bond distances between zinc and the coordinated atoms of Zn—O(2) 1.999 (2); Zn—O(1) 2.0137 (19); Zn—O(2 A) 2.0254 (17); Zn—N(3) 2.092 (2); and Zn—N(4) 2.115 (2) are compatible with the Zn—O and Zn—N distances found in other zinc ketiminate complexes (Huang et al., 2009).

Experimental

The ligand, (4Z)-4-{[(pyridin-2-yl)methylamino](4-tert-butylphenyl)methylene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (L—H) was prepared by the following procedures. 2-(Aminomethyl)pyridine (1.03 ml, 10.0 mmol) and 4-[(4-tert-butylphenyl)carbonyl]-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one (3.34 g, 10.0 mmol) were refluxed in ethanol (40 ml) for 24 h. The volatile materials were removed in under vacuum to produce yellow powder. The powder was then dissolved in hot ethanol (30 ml) and cooled to -18°C for 24 h giving yellow crystals.

The title complex was synthesized by the following procedures. Diethylzinc (2.2 ml, 1.0 M in hexane, 2.2 mmol) was slowly added to a suspension of L—H (0.85 g, 2.0 mmol) in toluene (40 ml). The mixture was stirred at 0°C for 3 h and the volatile materials were removed in under vacuum to yield white powder. The powder was dissolved in toluene (40 ml), and then benzyl alcohol (0.21 ml, 2.0 mmol) was added at 0°C. Continuously stirring at 0°C for another 3 h, the mixture initially turned colorless and then into white turbid. After filtration and washing with cooled toluene three times, a white powder was obtained. The resulting powder was recrystallized with a mixted dichloromathane and hexane solution to yield white crystals.

Refinement

The methyl H atoms were constrained to an ideal geometry with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.95–1.00 Å and Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
A view of the molecular structure of the title compound with displacement ellipsoids shown at the 20% probability level. Symmetry operator (A): 1-x,1-y,2-z.

Crystal data

[Zn2(C27H27N4O)2(C7H7O)2]Z = 1
Mr = 1192.04F(000) = 624
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0873 (15) ÅCell parameters from 4007 reflections
b = 13.363 (2) Åθ = 2.3–26.0°
c = 13.397 (2) ŵ = 0.86 mm1
α = 72.206 (3)°T = 293 K
β = 74.018 (3)°Parallelepiped, white
γ = 88.664 (3)°0.41 × 0.32 × 0.25 mm
V = 1485.9 (4) Å3

Data collection

Bruker SMART 1000 CCD diffractometer5792 independent reflections
Radiation source: fine-focus sealed tube4450 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 26.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.719, Tmax = 0.813k = −16→14
8258 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0902P)2] where P = (Fo2 + 2Fc2)/3
5792 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = −0.44 e Å3

Special details

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.

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

xyzUiso*/Ueq
Zn0.65973 (4)0.51056 (2)0.92949 (2)0.04217 (14)
O10.6604 (2)0.39430 (15)0.86285 (14)0.0471 (5)
O20.4651 (2)0.58125 (14)0.92139 (14)0.0427 (5)
N10.5943 (3)0.36547 (18)0.71795 (17)0.0414 (5)
N20.6169 (3)0.41391 (19)0.60618 (18)0.0479 (6)
N30.8186 (3)0.5971 (2)0.78379 (19)0.0502 (6)
N40.8045 (3)0.5874 (2)0.98662 (19)0.0510 (6)
C10.4996 (3)0.2706 (2)0.7697 (2)0.0445 (7)
C20.4698 (5)0.2198 (3)0.8796 (3)0.0766 (12)
H2B0.51210.24680.92260.092*
C30.3759 (6)0.1277 (4)0.9260 (3)0.0979 (17)
H3A0.35720.09261.00030.118*
C40.3106 (5)0.0875 (3)0.8657 (3)0.0866 (13)
H4A0.24590.02660.89840.104*
C50.3417 (5)0.1382 (3)0.7558 (3)0.0741 (11)
H5A0.29880.11090.71330.089*
C60.4359 (4)0.2295 (3)0.7076 (3)0.0557 (8)
H6A0.45630.26330.63290.067*
C70.7005 (3)0.5016 (2)0.5823 (2)0.0420 (6)
C80.7365 (3)0.5136 (2)0.6750 (2)0.0397 (6)
C90.6646 (3)0.4231 (2)0.7623 (2)0.0388 (6)
C100.7436 (4)0.5707 (3)0.4660 (2)0.0585 (8)
H10A0.70020.53970.42380.088*
H10B0.85330.57790.43730.088*
H10C0.70500.63880.46240.088*
C110.8166 (3)0.5975 (2)0.6870 (2)0.0401 (6)
C120.8939 (3)0.6863 (2)0.5875 (2)0.0415 (6)
C131.0346 (4)0.6780 (2)0.5185 (2)0.0527 (8)
H13A1.08600.61690.53550.063*
C141.0994 (4)0.7592 (3)0.4250 (2)0.0543 (8)
H14A1.19480.75190.38030.065*
C151.0275 (3)0.8518 (2)0.3950 (2)0.0449 (7)
C160.8896 (4)0.8605 (2)0.4664 (2)0.0507 (7)
H16A0.83940.92240.45060.061*
C170.8241 (3)0.7793 (2)0.5609 (2)0.0488 (7)
H17A0.73100.78780.60740.059*
C181.1010 (4)0.9370 (3)0.2872 (2)0.0528 (8)
C191.2569 (4)0.9755 (3)0.2883 (3)0.0788 (12)
H19A1.24371.00520.34680.118*
H19B1.30401.02820.22000.118*
H19C1.32120.91740.29890.118*
C201.0036 (5)1.0308 (3)0.2664 (3)0.0740 (11)
H20A0.99031.06210.32370.111*
H20B0.90521.00790.26480.111*
H20C1.05371.08180.19750.111*
C211.1214 (5)0.8895 (3)0.1935 (3)0.0781 (12)
H21A1.02310.86450.19370.117*
H21B1.18660.83190.20330.117*
H21C1.16700.94240.12500.117*
C220.9139 (4)0.6774 (3)0.7947 (3)0.0656 (10)
H22A0.87420.74590.77040.079*
H22B1.01770.67960.74870.079*
C230.9158 (3)0.6541 (2)0.9110 (2)0.0471 (7)
C241.0260 (4)0.7008 (3)0.9383 (3)0.0596 (8)
H24A1.10380.74620.88380.072*
C251.0206 (4)0.6803 (3)1.0458 (3)0.0723 (11)
H25A1.09430.71111.06550.087*
C260.9044 (5)0.6135 (4)1.1235 (3)0.0837 (13)
H26A0.89660.59871.19730.100*
C270.8007 (5)0.5690 (3)1.0911 (3)0.0770 (12)
H27A0.72260.52321.14460.092*
C280.4663 (4)0.6915 (2)0.8848 (2)0.0480 (7)
H28A0.56520.72070.88090.058*
H28B0.38890.71420.93800.058*
C290.4367 (3)0.7360 (2)0.7741 (2)0.0403 (6)
C300.4252 (3)0.6741 (2)0.7107 (2)0.0487 (7)
H30A0.43710.60220.73540.058*
C310.3960 (4)0.7178 (3)0.6106 (3)0.0654 (10)
H31A0.38500.67490.56970.078*
C320.3834 (5)0.8241 (4)0.5718 (3)0.0781 (12)
H32A0.36560.85360.50410.094*
C330.3972 (5)0.8868 (3)0.6333 (3)0.0729 (11)
H33A0.38910.95900.60690.087*
C340.4229 (4)0.8433 (3)0.7342 (2)0.0534 (8)
H34A0.43100.88640.77560.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn0.0478 (2)0.0436 (2)0.02763 (18)−0.01468 (14)−0.00437 (13)−0.00471 (13)
O10.0647 (13)0.0423 (11)0.0272 (9)−0.0156 (9)−0.0091 (9)−0.0030 (8)
O20.0523 (12)0.0410 (11)0.0266 (9)−0.0093 (9)−0.0090 (8)0.0000 (8)
N10.0531 (14)0.0391 (12)0.0267 (11)−0.0090 (10)−0.0062 (10)−0.0066 (9)
N20.0598 (16)0.0497 (14)0.0302 (12)−0.0059 (12)−0.0118 (11)−0.0069 (10)
N30.0580 (15)0.0508 (14)0.0328 (12)−0.0232 (12)−0.0025 (11)−0.0077 (11)
N40.0551 (15)0.0541 (15)0.0392 (13)−0.0164 (12)−0.0099 (11)−0.0095 (11)
C10.0483 (16)0.0417 (15)0.0385 (15)−0.0071 (12)−0.0060 (12)−0.0101 (12)
C20.108 (3)0.074 (2)0.0359 (17)−0.049 (2)−0.0090 (18)−0.0065 (16)
C30.137 (4)0.088 (3)0.046 (2)−0.065 (3)−0.010 (2)0.001 (2)
C40.095 (3)0.078 (3)0.072 (3)−0.050 (2)−0.009 (2)−0.013 (2)
C50.082 (3)0.073 (2)0.069 (2)−0.027 (2)−0.025 (2)−0.019 (2)
C60.066 (2)0.0536 (18)0.0472 (17)−0.0116 (15)−0.0185 (15)−0.0125 (15)
C70.0477 (16)0.0404 (15)0.0321 (13)−0.0004 (12)−0.0072 (12)−0.0063 (12)
C80.0460 (15)0.0356 (14)0.0291 (13)−0.0032 (11)−0.0034 (11)−0.0042 (11)
C90.0429 (15)0.0360 (14)0.0320 (13)−0.0025 (11)−0.0036 (11)−0.0084 (11)
C100.081 (2)0.0513 (18)0.0347 (15)−0.0091 (16)−0.0180 (15)0.0010 (14)
C110.0387 (14)0.0379 (14)0.0339 (14)−0.0030 (11)−0.0021 (11)−0.0042 (11)
C120.0433 (15)0.0399 (15)0.0323 (13)−0.0091 (12)−0.0024 (11)−0.0050 (11)
C130.0492 (17)0.0459 (17)0.0440 (16)0.0024 (13)0.0039 (13)−0.0022 (14)
C140.0409 (16)0.0532 (18)0.0461 (17)0.0005 (13)0.0096 (13)−0.0025 (14)
C150.0422 (15)0.0438 (16)0.0377 (15)−0.0102 (12)−0.0051 (12)−0.0016 (12)
C160.0544 (18)0.0388 (16)0.0455 (17)−0.0009 (13)−0.0050 (14)−0.0018 (13)
C170.0427 (16)0.0471 (17)0.0430 (16)−0.0017 (13)0.0042 (13)−0.0088 (13)
C180.0507 (17)0.0523 (18)0.0417 (16)−0.0163 (14)−0.0078 (13)0.0017 (14)
C190.060 (2)0.083 (3)0.066 (2)−0.034 (2)−0.0106 (18)0.013 (2)
C200.077 (3)0.053 (2)0.067 (2)−0.0181 (18)−0.015 (2)0.0134 (18)
C210.094 (3)0.081 (3)0.0379 (18)−0.019 (2)−0.0038 (18)0.0005 (18)
C220.077 (2)0.063 (2)0.0444 (17)−0.0382 (18)−0.0040 (16)−0.0076 (16)
C230.0465 (16)0.0455 (16)0.0438 (16)−0.0097 (13)−0.0053 (13)−0.0118 (13)
C240.0512 (19)0.061 (2)0.063 (2)−0.0147 (15)−0.0099 (16)−0.0178 (17)
C250.068 (2)0.086 (3)0.073 (2)−0.013 (2)−0.034 (2)−0.026 (2)
C260.100 (3)0.102 (3)0.053 (2)−0.030 (3)−0.032 (2)−0.018 (2)
C270.091 (3)0.091 (3)0.0382 (18)−0.039 (2)−0.0133 (18)−0.0074 (18)
C280.0621 (19)0.0452 (16)0.0309 (14)−0.0088 (14)−0.0118 (13)−0.0040 (12)
C290.0336 (14)0.0458 (15)0.0309 (13)−0.0058 (11)−0.0021 (11)−0.0025 (11)
C300.0511 (17)0.0510 (17)0.0347 (14)−0.0074 (13)−0.0073 (13)−0.0037 (13)
C310.073 (2)0.082 (3)0.0418 (18)−0.0075 (19)−0.0205 (17)−0.0154 (18)
C320.088 (3)0.095 (3)0.045 (2)0.007 (2)−0.032 (2)0.000 (2)
C330.088 (3)0.057 (2)0.055 (2)0.0158 (19)−0.0182 (19)0.0073 (17)
C340.0531 (18)0.0544 (19)0.0442 (17)0.0009 (14)−0.0103 (14)−0.0062 (14)

Geometric parameters (Å, °)

Zn—O21.999 (2)C15—C161.379 (4)
Zn—O12.0137 (19)C15—C181.526 (4)
Zn—O2i2.0253 (17)C16—C171.382 (4)
Zn—N32.092 (2)C16—H16A0.9300
Zn—N42.114 (2)C17—H17A0.9300
Zn—Zni2.9612 (8)C18—C201.518 (5)
O1—C91.272 (3)C18—C191.523 (5)
O2—C281.403 (3)C18—C211.539 (5)
O2—Zni2.0253 (17)C19—H19A0.9600
N1—C91.367 (3)C19—H19B0.9600
N1—N21.396 (3)C19—H19C0.9600
N1—C11.419 (3)C20—H20A0.9600
N2—C71.315 (4)C20—H20B0.9600
N3—C111.300 (4)C20—H20C0.9600
N3—C221.460 (4)C21—H21A0.9600
N4—C231.329 (4)C21—H21B0.9600
N4—C271.335 (4)C21—H21C0.9600
C1—C21.372 (4)C22—C231.498 (4)
C1—C61.374 (4)C22—H22A0.9700
C2—C31.384 (5)C22—H22B0.9700
C2—H2B0.9300C23—C241.377 (4)
C3—C41.355 (5)C24—C251.368 (5)
C3—H3A0.9300C24—H24A0.9300
C4—C51.370 (5)C25—C261.366 (5)
C4—H4A0.9300C25—H25A0.9300
C5—C61.378 (5)C26—C271.356 (5)
C5—H5A0.9300C26—H26A0.9300
C6—H6A0.9300C27—H27A0.9300
C7—C81.423 (4)C28—C291.516 (4)
C7—C101.495 (4)C28—H28A0.9700
C8—C91.418 (4)C28—H28B0.9700
C8—C111.422 (4)C29—C301.378 (4)
C10—H10A0.9600C29—C341.385 (4)
C10—H10B0.9600C30—C311.386 (4)
C10—H10C0.9600C30—H30A0.9300
C11—C121.495 (3)C31—C321.369 (6)
C12—C171.375 (4)C31—H31A0.9300
C12—C131.381 (4)C32—C331.370 (6)
C13—C141.374 (4)C32—H32A0.9300
C13—H13A0.9300C33—C341.380 (5)
C14—C151.386 (4)C33—H33A0.9300
C14—H14A0.9300C34—H34A0.9300
O2—Zn—O1105.69 (8)C14—C15—C18119.9 (3)
O2—Zn—O2i85.26 (8)C15—C16—C17121.4 (3)
O1—Zn—O2i92.46 (7)C15—C16—H16A119.3
O2—Zn—N3103.26 (9)C17—C16—H16A119.3
O1—Zn—N387.87 (9)C12—C17—C16121.3 (3)
O2i—Zn—N3171.07 (9)C12—C17—H17A119.3
O2—Zn—N4113.40 (10)C16—C17—H17A119.3
O1—Zn—N4140.49 (10)C15—C18—C20112.5 (3)
O2i—Zn—N496.22 (8)C15—C18—C19109.5 (3)
N3—Zn—N478.03 (9)C20—C18—C19108.5 (3)
O2—Zn—Zni42.97 (5)C15—C18—C21108.6 (3)
O1—Zn—Zni102.23 (6)C20—C18—C21108.1 (3)
O2i—Zn—Zni42.29 (6)C19—C18—C21109.7 (3)
N3—Zn—Zni146.15 (8)C18—C19—H19A109.5
N4—Zn—Zni110.01 (7)C18—C19—H19B109.5
C9—O1—Zn116.06 (17)H19A—C19—H19B109.5
C28—O2—Zn120.26 (18)C18—C19—H19C109.5
C28—O2—Zni124.18 (17)H19A—C19—H19C109.5
Zn—O2—Zni94.74 (8)H19B—C19—H19C109.5
C9—N1—N2111.9 (2)C18—C20—H20A109.5
C9—N1—C1129.6 (2)C18—C20—H20B109.5
N2—N1—C1118.4 (2)H20A—C20—H20B109.5
C7—N2—N1105.2 (2)C18—C20—H20C109.5
C11—N3—C22119.5 (2)H20A—C20—H20C109.5
C11—N3—Zn124.61 (19)H20B—C20—H20C109.5
C22—N3—Zn114.56 (19)C18—C21—H21A109.5
C23—N4—C27117.6 (3)C18—C21—H21B109.5
C23—N4—Zn116.6 (2)H21A—C21—H21B109.5
C27—N4—Zn125.7 (2)C18—C21—H21C109.5
C2—C1—C6119.6 (3)H21A—C21—H21C109.5
C2—C1—N1121.6 (3)H21B—C21—H21C109.5
C6—C1—N1118.8 (3)N3—C22—C23110.6 (2)
C1—C2—C3119.2 (3)N3—C22—H22A109.5
C1—C2—H2B120.4C23—C22—H22A109.5
C3—C2—H2B120.4N3—C22—H22B109.5
C4—C3—C2121.6 (4)C23—C22—H22B109.5
C4—C3—H3A119.2H22A—C22—H22B108.1
C2—C3—H3A119.2N4—C23—C24121.7 (3)
C3—C4—C5118.9 (3)N4—C23—C22116.7 (3)
C3—C4—H4A120.5C24—C23—C22121.5 (3)
C5—C4—H4A120.5C23—C24—C25119.7 (3)
C4—C5—C6120.5 (3)C23—C24—H24A120.1
C4—C5—H5A119.7C25—C24—H24A120.1
C6—C5—H5A119.7C26—C25—C24118.5 (3)
C1—C6—C5120.2 (3)C26—C25—H25A120.8
C1—C6—H6A119.9C24—C25—H25A120.8
C5—C6—H6A119.9C27—C26—C25118.9 (3)
N2—C7—C8112.4 (2)C27—C26—H26A120.6
N2—C7—C10117.1 (3)C25—C26—H26A120.6
C8—C7—C10130.5 (3)N4—C27—C26123.6 (3)
C7—C8—C9104.7 (2)N4—C27—H27A118.2
C7—C8—C11131.0 (2)C26—C27—H27A118.2
C9—C8—C11124.2 (2)O2—C28—C29114.0 (2)
O1—C9—N1123.1 (2)O2—C28—H28A108.7
O1—C9—C8131.0 (3)C29—C28—H28A108.7
N1—C9—C8105.8 (2)O2—C28—H28B108.7
C7—C10—H10A109.5C29—C28—H28B108.7
C7—C10—H10B109.5H28A—C28—H28B107.6
H10A—C10—H10B109.5C30—C29—C34118.5 (3)
C7—C10—H10C109.5C30—C29—C28122.6 (3)
H10A—C10—H10C109.5C34—C29—C28118.8 (3)
H10B—C10—H10C109.5C29—C30—C31120.7 (3)
N3—C11—C8119.8 (2)C29—C30—H30A119.7
N3—C11—C12121.1 (3)C31—C30—H30A119.7
C8—C11—C12119.0 (2)C32—C31—C30120.2 (4)
C17—C12—C13117.7 (3)C32—C31—H31A119.9
C17—C12—C11120.3 (3)C30—C31—H31A119.9
C13—C12—C11122.0 (3)C31—C32—C33119.7 (3)
C14—C13—C12120.7 (3)C31—C32—H32A120.2
C14—C13—H13A119.7C33—C32—H32A120.2
C12—C13—H13A119.7C32—C33—C34120.4 (3)
C13—C14—C15122.2 (3)C32—C33—H33A119.8
C13—C14—H14A118.9C34—C33—H33A119.8
C15—C14—H14A118.9C33—C34—C29120.5 (3)
C16—C15—C14116.6 (3)C33—C34—H34A119.8
C16—C15—C18123.5 (3)C29—C34—H34A119.8

Symmetry codes: (i) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2979).

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