Diacetato{4′-[4-(benz­yloxy)phen­yl]-2,2′:6′,2′′-terpyridine}zinc(II)

Li, W.; Lu, Z.G.

doi:10.1107/S1600536809049502

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1672

doi:10.1107/S1600536809049502

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Diacetato{4′-[4-(benzyloxy)phenyl]-2,2′:6′,2′′-terpyridine}zinc(II)

Wei Li ^a ^* and Zhan Guo Lu ^a

^aSchool of Food Engineering, Harbin University of Commerce, Harbin 150076, People's Republic of China
^*Correspondence e-mail: liw@hrbcu.edu.cn

(Received 13 November 2009; accepted 19 November 2009; online 25 November 2009)

In the title compound, [Zn(CH₃COO)₂(C₂₈H₂₁N₃O)], the Zn^II ion is in a trigonal–bipyramidal ZnN₃O₂ coordination with a tridentate N-chelating 4′-[4-(benzyloxy)phenyl)-2,2′:6′,2′′-terpyridine ligand in the equatorial position and two acetate anions in the axial positions. The three pyridine rings are approximately coplanar, with a maximum deviation of 0.03 Å from the mean plane. The phenoxy substituent makes a dihedral angle of 18.1 (2)° with the central pyridine ring. The benzyl group has a C—O—C—C torsion angle of 77.62 (8)° relative to the phenoxy ring. In the crystal, molecules are linked via C—H⋯O hydrogen bonds.

Related literature

For the synthesis of functionalized terpyridines, see: Heller & Schubert (2003 ). For other structures with terpyridine ligands, see: Duprez et al. (2005 ). For a trans–trans arrangement of the pyridine rings about the interannular C—C bonds in the structure of a similar ligand, see: Anthonysamy et al. (2007 ). PLATON (Spek, 2009 ) was used for structure evaluation.

Experimental

Crystal data

[Zn(C₂H₃O₂)₂(C₂₈H₂₁N₃O)]
M_r = 598.94
Monoclinic, P n
a = 8.3959 (17) Å
b = 15.564 (3) Å
c = 10.702 (2) Å
β = 102.23 (3)°
V = 1366.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 291 K
0.26 × 0.23 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.791, T_max = 0.826
13194 measured reflections
5859 independent reflections
3538 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.106
S = 0.98
5859 reflections
373 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 2733 Friedel pairs
Flack parameter: 0.108 (13)

Table 1
Selected bond lengths (Å)

Zn1—N1	2.187 (4)
Zn1—N2	2.090 (3)
Zn1—N3	2.151 (5)
Zn1—O2	2.014 (4)
Zn1—O4	1.961 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5ⁱ	0.93	2.39	3.293 (7)	163
C12—H12⋯O3ⁱⁱ	0.93	2.24	3.147 (7)	165
C22—H22B⋯O4ⁱⁱⁱ	0.97	2.48	3.429 (6)	166
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049502/wm2284sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049502/wm2284Isup2.hkl

checkCIF report

Comment top

Functionalized terpyridines are interesting materials (Heller & Schubert, 2003). 2,2':6',2"-terpyridine and its derivatives have been used as key building blocks in supramolecular frameworks (Duprez et al., 2005). We report here the crystal structure of the title compound, (I).

In the molecular structure of (I) (Fig. 1), the three pyridine rings are approximately coplanar (max. deviation from the mean plane 0.03 Å). The Zn^II ion is in a trigonal-bipyramidal coordination by a neutral tridentate 4'-[4-(benzyloxy)phenyl)-2,2':6',2"-terpyridine ligand in equatorial and two acetate anions in axial positions (Table 1). The phenoxy substituent makes a dihedral angle of 18.1 (2)° with the central pyridine ring. The torsion angle between the benzoyl group and the attached phenoxy ring, defined by atoms C19—O01—C22—C23, is 77.6 (7)°.

Molecules of (I) are linked via O—H···C hydrogen bonds, as shown in Fig. 2. Molecules associate via C(22)—H(22B)···O(4)#3 interactions, forming a chain along the b axis. Adjacent chains are interconnected via C(4)—H(4)···O(5)#1 and C(12)—H(12)···O(3)#2 interactions, leading to the formation of a two dimensional network (Table 2).

In the structure of a similar ligand molecule (Anthonysamy et al., 2007) a trans-trans arrangement of the pyridine rings about the interannular C—C bonds is observed.

Related literature top

For the synthesis of functionalized terpyridines, see: Heller & Schubert (2003). For other structures with terpyridine ligands, see: Duprez et al. (2005). For a trans–trans arrangement of the pyridine rings about the interannular C—C bonds in the structure of a similar ligand, see: Anthonysamy et al. (2007). PLATON (Spek, 2009) was used for structure evaluation.

Experimental top

To a tetrahydrofuran solution (10 ml) of the ligand L (0.100 g, 0.241 mmol) was slowly added a methanolic solution (10 ml) of zinc acetate (0.044 g, 0.241 mmol). After stirring for 3 h at ambient temperature, a white solid was collected by filtration and washed with MeOH. Colorless single crystals suitable for X-ray determination were obtained by vapour diffusion of diethyl ether into a methanol solution of the powder sample over the course of 5 days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of a hydrogen-bonded (dashed lines) chain in (I). H atoms not involved in hydrogen bonding have been omitted.

Diacetato{4'-[4-(benzyloxy)phenyl]-2,2':6',2''-terpyridine}zinc(II) top

Crystal data top

[Zn(C₂H₃O₂)₂(C₂₈H₂₁N₃O)]	F(000) = 620
M_r = 598.94	D_x = 1.455 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 8985 reflections
a = 8.3959 (17) Å	θ = 3.1–27.4°
b = 15.564 (3) Å	µ = 0.95 mm⁻¹
c = 10.702 (2) Å	T = 291 K
β = 102.23 (3)°	Block, colorless
V = 1366.7 (5) Å³	0.26 × 0.23 × 0.21 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	5859 independent reflections
Radiation source: fine-focus sealed tube	3538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scan	θ_max = 27.4°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.791, T_max = 0.826	k = −20→20
13194 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0503P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
5859 reflections	Δρ_max = 0.48 e Å⁻³
373 parameters	Δρ_min = −0.56 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2733 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.108 (13)

Crystal data top

[Zn(C₂H₃O₂)₂(C₂₈H₂₁N₃O)]	V = 1366.7 (5) Å³
M_r = 598.94	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 8.3959 (17) Å	µ = 0.95 mm⁻¹
b = 15.564 (3) Å	T = 291 K
c = 10.702 (2) Å	0.26 × 0.23 × 0.21 mm
β = 102.23 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5859 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3538 reflections with I > 2σ(I)
T_min = 0.791, T_max = 0.826	R_int = 0.043
13194 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.48 e Å⁻³
S = 0.98	Δρ_min = −0.56 e Å⁻³
5859 reflections	Absolute structure: Flack (1983), 2733 Friedel pairs
373 parameters	Absolute structure parameter: 0.108 (13)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.8831 (7)	0.3046 (4)	0.9729 (6)	0.0593 (17)
H1	0.8640	0.2457	0.9695	0.071*
C2	1.0368 (7)	0.3342 (4)	1.0203 (7)	0.071 (2)
H2	1.1225	0.2956	1.0432	0.085*
C3	1.0655 (6)	0.4200 (4)	1.0342 (5)	0.0584 (15)
H3	1.1690	0.4404	1.0707	0.070*
C4	0.9378 (6)	0.4766 (4)	0.9929 (5)	0.0547 (14)
H4	0.9538	0.5357	0.9989	0.066*
C5	0.7855 (6)	0.4424 (3)	0.9424 (5)	0.0457 (12)
C6	0.6379 (6)	0.4966 (3)	0.8920 (5)	0.0436 (13)
C7	0.6359 (6)	0.5845 (3)	0.8898 (5)	0.0505 (14)
H7	0.7320	0.6150	0.9187	0.061*
C8	0.4896 (7)	0.6291 (2)	0.8440 (7)	0.0441 (10)
C9	0.3513 (6)	0.5806 (3)	0.8006 (5)	0.0478 (13)
H9	0.2518	0.6076	0.7702	0.057*
C10	0.3608 (6)	0.4912 (3)	0.8023 (5)	0.0423 (13)
C11	0.2215 (6)	0.4320 (3)	0.7578 (5)	0.0475 (13)
C12	0.0654 (6)	0.4599 (4)	0.7014 (5)	0.0571 (15)
H12	0.0426	0.5181	0.6880	0.068*
C13	−0.0562 (7)	0.3980 (4)	0.6655 (6)	0.0645 (17)
H13	−0.1622	0.4148	0.6292	0.077*
C14	−0.0200 (7)	0.3134 (4)	0.6834 (6)	0.0600 (16)
H14	−0.0997	0.2718	0.6585	0.072*
C15	0.1373 (7)	0.2905 (4)	0.7393 (6)	0.0615 (16)
H15	0.1606	0.2325	0.7536	0.074*
C16	0.4862 (7)	0.7251 (2)	0.8434 (6)	0.0482 (11)
C17	0.6114 (7)	0.7729 (4)	0.9184 (6)	0.0603 (15)
H17	0.6995	0.7449	0.9696	0.072*
C18	0.6047 (7)	0.8626 (4)	0.9167 (6)	0.0638 (16)
H18	0.6878	0.8943	0.9676	0.077*
C19	0.4755 (6)	0.9042 (3)	0.8400 (6)	0.0562 (14)
C20	0.3523 (6)	0.8577 (3)	0.7660 (6)	0.0611 (15)
H20	0.2646	0.8859	0.7146	0.073*
C21	0.3582 (6)	0.7699 (3)	0.7674 (5)	0.0573 (14)
H21	0.2740	0.7392	0.7161	0.069*
C22	0.3569 (6)	1.0418 (3)	0.7676 (6)	0.0794 (14)
H22A	0.3336	1.0169	0.6825	0.095*
H22B	0.3954	1.1000	0.7606	0.095*
C23	0.2019 (6)	1.0450 (3)	0.8165 (5)	0.0635 (13)
C24	0.2036 (7)	1.0670 (3)	0.9414 (5)	0.0758 (14)
H24	0.3027	1.0775	0.9972	0.091*
C25	0.0619 (8)	1.0737 (4)	0.9849 (7)	0.0897 (18)
H25	0.0673	1.0886	1.0699	0.108*
C26	−0.0850 (8)	1.0595 (4)	0.9082 (8)	0.0888 (19)
H26	−0.1798	1.0633	0.9397	0.107*
C27	−0.0913 (7)	1.0392 (4)	0.7829 (8)	0.100 (2)
H27	−0.1920	1.0308	0.7283	0.120*
C28	0.0516 (8)	1.0309 (4)	0.7351 (6)	0.0859 (18)
H28	0.0456	1.0161	0.6500	0.103*
C29	0.4567 (6)	0.2751 (4)	1.0846 (6)	0.0572 (15)
C30	0.4161 (8)	0.2233 (5)	1.1989 (7)	0.100 (2)
H30A	0.3133	0.1947	1.1716	0.149*
H30B	0.4099	0.2619	1.2676	0.149*
H30C	0.4999	0.1815	1.2276	0.149*
C31	0.5525 (6)	0.2511 (4)	0.6214 (6)	0.0605 (15)
C32	0.5948 (9)	0.1794 (4)	0.5365 (6)	0.086 (2)
H32A	0.4985	0.1626	0.4757	0.129*
H32B	0.6371	0.1309	0.5885	0.129*
H32C	0.6754	0.1997	0.4919	0.129*
N1	0.7606 (5)	0.3578 (3)	0.9319 (5)	0.0481 (11)
N2	0.5019 (6)	0.45091 (16)	0.8450 (5)	0.0440 (7)
N3	0.2591 (6)	0.3473 (3)	0.7745 (5)	0.0523 (12)
O1	0.4850 (6)	0.99246 (16)	0.8480 (6)	0.0784 (10)
O2	0.4764 (5)	0.2367 (3)	0.9965 (4)	0.0664 (11)
O3	0.4605 (6)	0.3537 (3)	1.1031 (5)	0.0977 (14)
O4	0.5539 (5)	0.2307 (2)	0.7346 (4)	0.0696 (11)
O5	0.5191 (7)	0.3222 (3)	0.5782 (5)	0.1088 (18)
Zn1	0.50944 (8)	0.31689 (2)	0.85645 (8)	0.05098 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.049 (3)	0.046 (3)	0.082 (4)	0.007 (2)	0.012 (3)	0.009 (3)
C2	0.042 (3)	0.078 (4)	0.092 (5)	0.017 (3)	0.010 (3)	0.010 (3)
C3	0.042 (3)	0.066 (3)	0.063 (3)	−0.001 (3)	0.002 (2)	0.000 (3)
C4	0.043 (3)	0.056 (3)	0.065 (3)	0.001 (2)	0.011 (2)	−0.004 (3)
C5	0.040 (3)	0.044 (3)	0.056 (3)	−0.001 (2)	0.017 (2)	0.000 (2)
C6	0.039 (3)	0.037 (3)	0.056 (3)	0.003 (2)	0.013 (2)	−0.005 (2)
C7	0.046 (3)	0.042 (3)	0.064 (3)	−0.009 (2)	0.013 (2)	−0.003 (2)
C8	0.043 (3)	0.0359 (16)	0.055 (3)	0.003 (2)	0.013 (2)	0.001 (3)
C9	0.037 (3)	0.041 (3)	0.065 (3)	0.000 (2)	0.010 (2)	0.000 (2)
C10	0.040 (3)	0.037 (3)	0.049 (3)	0.004 (2)	0.009 (2)	−0.003 (2)
C11	0.040 (3)	0.047 (3)	0.057 (3)	−0.004 (2)	0.012 (2)	0.003 (2)
C12	0.050 (3)	0.051 (3)	0.068 (4)	0.004 (2)	0.007 (3)	0.003 (3)
C13	0.039 (3)	0.071 (4)	0.081 (4)	−0.005 (3)	0.007 (2)	−0.001 (3)
C14	0.048 (3)	0.055 (3)	0.073 (4)	−0.014 (2)	0.005 (3)	−0.009 (2)
C15	0.053 (3)	0.045 (3)	0.088 (5)	−0.011 (3)	0.017 (3)	0.001 (3)
C16	0.051 (3)	0.0395 (18)	0.057 (3)	−0.007 (2)	0.018 (2)	−0.007 (3)
C17	0.053 (3)	0.044 (3)	0.080 (4)	0.002 (2)	0.005 (3)	−0.002 (3)
C18	0.050 (3)	0.043 (3)	0.093 (4)	−0.004 (2)	0.004 (3)	−0.010 (3)
C19	0.050 (4)	0.0365 (19)	0.082 (4)	−0.002 (2)	0.014 (3)	0.000 (3)
C20	0.052 (3)	0.039 (3)	0.092 (4)	0.001 (2)	0.014 (3)	0.005 (3)
C21	0.053 (3)	0.039 (3)	0.077 (4)	−0.001 (2)	0.008 (2)	0.007 (3)
C22	0.082 (4)	0.039 (2)	0.122 (4)	0.002 (2)	0.031 (3)	0.009 (3)
C23	0.061 (3)	0.034 (2)	0.093 (4)	0.007 (2)	0.011 (3)	0.007 (2)
C24	0.065 (3)	0.065 (3)	0.095 (4)	−0.001 (3)	0.013 (3)	0.000 (3)
C25	0.088 (5)	0.080 (4)	0.109 (5)	0.003 (3)	0.038 (4)	−0.008 (3)
C26	0.081 (5)	0.067 (4)	0.124 (6)	−0.004 (3)	0.036 (4)	−0.001 (4)
C27	0.059 (4)	0.087 (5)	0.144 (7)	0.006 (3)	0.001 (4)	0.009 (4)
C28	0.082 (4)	0.080 (4)	0.090 (5)	0.000 (3)	0.008 (3)	0.001 (3)
C29	0.031 (2)	0.059 (4)	0.074 (4)	−0.007 (2)	−0.006 (2)	0.012 (3)
C30	0.076 (4)	0.106 (6)	0.113 (5)	−0.001 (4)	0.013 (4)	0.036 (5)
C31	0.045 (3)	0.048 (3)	0.084 (4)	0.003 (2)	0.002 (2)	−0.002 (3)
C32	0.089 (4)	0.094 (5)	0.074 (4)	0.022 (4)	0.017 (3)	−0.017 (3)
N1	0.040 (2)	0.037 (2)	0.071 (3)	0.0050 (19)	0.020 (2)	0.000 (2)
N2	0.0421 (15)	0.0334 (13)	0.056 (2)	−0.001 (2)	0.0103 (14)	−0.002 (2)
N3	0.047 (3)	0.040 (2)	0.068 (3)	0.000 (2)	0.010 (2)	−0.002 (2)
O1	0.062 (3)	0.0335 (13)	0.141 (3)	−0.0014 (18)	0.024 (2)	0.000 (3)
O2	0.072 (3)	0.049 (2)	0.083 (3)	−0.0032 (19)	0.027 (2)	0.004 (2)
O3	0.113 (3)	0.073 (3)	0.112 (3)	−0.017 (3)	0.034 (3)	−0.019 (3)
O4	0.078 (3)	0.049 (2)	0.080 (3)	0.008 (2)	0.014 (2)	−0.001 (2)
O5	0.138 (5)	0.077 (3)	0.118 (4)	0.024 (3)	0.042 (3)	0.026 (3)
Zn1	0.0465 (2)	0.0366 (2)	0.0702 (3)	0.0007 (4)	0.01314 (18)	0.0003 (4)

Geometric parameters (Å, º) top

C1—N1	1.320 (7)	C19—C20	1.369 (7)
C1—C2	1.363 (9)	C19—O1	1.377 (5)
C1—H1	0.9300	C20—C21	1.369 (8)
C2—C3	1.359 (8)	C20—H20	0.9300
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.385 (7)	C22—O1	1.448 (6)
C3—H3	0.9300	C22—C23	1.503 (7)
C4—C5	1.385 (7)	C22—H22A	0.9700
C4—H4	0.9300	C22—H22B	0.9700
C5—N1	1.334 (7)	C23—C24	1.377 (7)
C5—C6	1.503 (7)	C23—C28	1.391 (7)
C6—N2	1.349 (6)	C24—C25	1.370 (8)
C6—C7	1.368 (8)	C24—H24	0.9300
C7—C8	1.406 (7)	C25—C26	1.347 (8)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.381 (7)	C26—C27	1.367 (9)
C8—C16	1.494 (5)	C26—H26	0.9300
C9—C10	1.394 (8)	C27—C28	1.406 (9)
C9—H9	0.9300	C27—H27	0.9300
C10—N2	1.333 (6)	C28—H28	0.9300
C10—C11	1.486 (7)	C29—O2	1.158 (6)
C11—N3	1.359 (7)	C29—O3	1.238 (7)
C11—C12	1.391 (7)	C29—C30	1.562 (8)
C12—C13	1.397 (7)	C30—H30A	0.9600
C12—H12	0.9300	C30—H30B	0.9600
C13—C14	1.355 (8)	C30—H30C	0.9600
C13—H13	0.9300	C31—O5	1.209 (7)
C14—C15	1.376 (8)	C31—O4	1.249 (7)
C14—H14	0.9300	C31—C32	1.527 (8)
C15—N3	1.344 (7)	C32—H32A	0.9600
C15—H15	0.9300	C32—H32B	0.9600
C16—C21	1.390 (7)	C32—H32C	0.9600
C16—C17	1.394 (7)	Zn1—N1	2.187 (4)
C17—C18	1.399 (9)	Zn1—N2	2.090 (3)
C17—H17	0.9300	Zn1—N3	2.151 (5)
C18—C19	1.376 (7)	Zn1—O2	2.014 (4)
C18—H18	0.9300	Zn1—O4	1.961 (4)

N1—C1—C2	121.4 (6)	O1—C22—H22A	108.9
N1—C1—H1	119.3	C23—C22—H22A	108.9
C2—C1—H1	119.3	O1—C22—H22B	108.9
C3—C2—C1	120.3 (6)	C23—C22—H22B	108.9
C3—C2—H2	119.9	H22A—C22—H22B	107.7
C1—C2—H2	119.9	C24—C23—C28	118.0 (5)
C2—C3—C4	118.8 (5)	C24—C23—C22	121.0 (5)
C2—C3—H3	120.6	C28—C23—C22	120.9 (5)
C4—C3—H3	120.6	C25—C24—C23	121.1 (5)
C5—C4—C3	117.9 (6)	C25—C24—H24	119.4
C5—C4—H4	121.0	C23—C24—H24	119.4
C3—C4—H4	121.0	C26—C25—C24	122.0 (7)
N1—C5—C4	121.8 (5)	C26—C25—H25	119.0
N1—C5—C6	115.0 (4)	C24—C25—H25	119.0
C4—C5—C6	123.2 (5)	C25—C26—C27	118.4 (6)
N2—C6—C7	121.0 (5)	C25—C26—H26	120.8
N2—C6—C5	113.9 (4)	C27—C26—H26	120.8
C7—C6—C5	125.1 (5)	C26—C27—C28	121.3 (5)
C6—C7—C8	120.4 (5)	C26—C27—H27	119.3
C6—C7—H7	119.8	C28—C27—H27	119.3
C8—C7—H7	119.8	C23—C28—C27	119.2 (6)
C9—C8—C7	117.3 (3)	C23—C28—H28	120.4
C9—C8—C16	122.1 (5)	C27—C28—H28	120.4
C7—C8—C16	120.6 (5)	O2—C29—O3	129.6 (6)
C8—C9—C10	120.0 (5)	O2—C29—C30	117.6 (5)
C8—C9—H9	120.0	O3—C29—C30	112.8 (6)
C10—C9—H9	120.0	C29—C30—H30A	109.5
N2—C10—C9	121.2 (5)	C29—C30—H30B	109.5
N2—C10—C11	113.6 (5)	H30A—C30—H30B	109.5
C9—C10—C11	125.2 (5)	C29—C30—H30C	109.5
N3—C11—C12	122.1 (5)	H30A—C30—H30C	109.5
N3—C11—C10	114.4 (4)	H30B—C30—H30C	109.5
C12—C11—C10	123.4 (5)	O5—C31—O4	123.8 (6)
C11—C12—C13	118.1 (6)	O5—C31—C32	120.4 (7)
C11—C12—H12	121.0	O4—C31—C32	115.8 (5)
C13—C12—H12	121.0	C31—C32—H32A	109.5
C14—C13—C12	120.1 (5)	C31—C32—H32B	109.5
C14—C13—H13	119.9	H32A—C32—H32B	109.5
C12—C13—H13	119.9	C31—C32—H32C	109.5
C13—C14—C15	118.6 (6)	H32A—C32—H32C	109.5
C13—C14—H14	120.7	H32B—C32—H32C	109.5
C15—C14—H14	120.7	C1—N1—C5	119.6 (5)
N3—C15—C14	123.7 (6)	C1—N1—Zn1	124.2 (4)
N3—C15—H15	118.1	C5—N1—Zn1	116.1 (3)
C14—C15—H15	118.1	C10—N2—C6	120.0 (3)
C21—C16—C17	117.7 (4)	C10—N2—Zn1	120.2 (4)
C21—C16—C8	121.0 (5)	C6—N2—Zn1	119.5 (4)
C17—C16—C8	121.3 (5)	C15—N3—C11	117.3 (5)
C16—C17—C18	120.2 (5)	C15—N3—Zn1	126.1 (4)
C16—C17—H17	119.9	C11—N3—Zn1	116.6 (3)
C18—C17—H17	119.9	C19—O1—C22	117.8 (4)
C19—C18—C17	120.1 (5)	C29—O2—Zn1	110.5 (4)
C19—C18—H18	119.9	C31—O4—Zn1	120.5 (4)
C17—C18—H18	119.9	O4—Zn1—O2	98.42 (13)
C20—C19—C18	120.0 (4)	O4—Zn1—N2	130.6 (2)
C20—C19—O1	126.1 (5)	O2—Zn1—N2	130.9 (2)
C18—C19—O1	113.8 (5)	O4—Zn1—N3	100.76 (19)
C21—C20—C19	120.0 (5)	O2—Zn1—N3	99.39 (18)
C21—C20—H20	120.0	N2—Zn1—N3	75.02 (19)
C19—C20—H20	120.0	N4—Zn1—N1	98.04 (17)
C20—C21—C16	122.0 (5)	O2—Zn1—N1	100.36 (18)
C20—C21—H21	119.0	N2—Zn1—N1	75.28 (18)
C16—C21—H21	119.0	N3—Zn1—N1	150.30 (11)
O1—C22—C23	113.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5ⁱ	0.93	2.39	3.293 (7)	163
C12—H12···O3ⁱⁱ	0.93	2.24	3.147 (7)	165
C22—H22B···O4ⁱⁱⁱ	0.97	2.48	3.429 (6)	166

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

Experimental details

Crystal data
Chemical formula	[Zn(C₂H₃O₂)₂(C₂₈H₂₁N₃O)]
M_r	598.94
Crystal system, space group	Monoclinic, Pn
Temperature (K)	291
a, b, c (Å)	8.3959 (17), 15.564 (3), 10.702 (2)
β (°)	102.23 (3)
V (Å³)	1366.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.26 × 0.23 × 0.21

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.791, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	13194, 5859, 3538
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.106, 0.98
No. of reflections	5859
No. of parameters	373
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.56
Absolute structure	Flack (1983), 2733 Friedel pairs
Absolute structure parameter	0.108 (13)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—N1	2.187 (4)	Zn1—O2	2.014 (4)
Zn1—N2	2.090 (3)	Zn1—O4	1.961 (4)
Zn1—N3	2.151 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5ⁱ	0.93	2.39	3.293 (7)	163.4
C12—H12···O3ⁱⁱ	0.93	2.24	3.147 (7)	164.8
C22—H22B···O4ⁱⁱⁱ	0.97	2.48	3.429 (6)	166.1

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

Acknowledgements

The authors thank Dr Guang Feng Hou for the single-crystal analysis.

References

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