Hexa-μ2-acetato-1:2κ4O:O′;1:2κ2O:O;2:3κ4O:O′;2:3κ2O:O-bis­(2-amino-7-chloro-5-methyl-1,8-naphthyridine)-1κN1,3κN1-trizinc(II)

Li, X.-S.; Mo, J.; Yuan, L.; Liu, J.-H.; Zhang, S.-M.

doi:10.1107/S1600536808024549

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1128

doi:10.1107/S1600536808024549

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Hexa-μ₂-acetato-1:2κ⁴O:O′;1:2κ²O:O;2:3κ⁴O:O′;2:3κ²O:O-bis(2-amino-7-chloro-5-methyl-1,8-naphthyridine)-1κN¹,3κN¹-trizinc(II)

Xin-Sheng Li,^a Juan Mo,^a ^* Li Yuan,^a Jian-Hua Liu ^a and Su-Mei Zhang ^a

^aCollege of Animal Husbandry and Veterinary Studies, Henan Agricultural University, Zhengzhou, Henan Province 450002, People's Republic of China
^*Correspondence e-mail: mojuan52@126.com

(Received 11 June 2008; accepted 31 July 2008; online 6 August 2008)

The title complex, [Zn₃(C₂H₃O₂)₆(C₉H₈ClN₃)₂], contains three Zn^II atoms bridged by six acetate ligands. The central Zn^II ion, located on an inversion centre, is surrounded by six O atoms from acetate ligands in a distorted octahedral geometry [Zn—O = 1.9588 (12)–2.1237 (12) Å]. The terminal Zn^II ions are coordinated by one N atom of 2-amino-7-chloro-5-methyl-1,8-naphthyridine and three O atoms of three acetate ligands in a distorted tetrahedral geometry. The separation between the central and terminal Zn^II ions is 3.245 (3) Å.

Related literature

For related literature, see: Baker & Norman (2004 ); Lis et al. (2005 ); Stadie et al. (2007 ).

Experimental

Crystal data

[Zn₃(C₂H₃O₂)₆(C₉H₈ClN₃)₂]
M_r = 937.64
Triclinic, $[P \overline 1]$
a = 9.1978 (12) Å
b = 9.2108 (13) Å
c = 12.0457 (16) Å
α = 93.602 (3)°
β = 91.685 (2)°
γ = 118.247 (2)°
V = 895.2 (2) Å³
Z = 1
Mo Kα radiation
μ = 2.21 mm⁻¹
T = 113 (2) K
0.12 × 0.08 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.782, T_max = 0.956
11008 measured reflections
4221 independent reflections
3495 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.065
S = 1.01
4221 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O3	2.0724 (12)
Zn1—O5	2.0910 (12)
Zn1—O1	2.1237 (12)
Zn2—O3	1.9588 (12)
Zn2—O2	1.9748 (12)
Zn2—N2	2.0379 (14)

O3—Zn1—O5ⁱ	91.21 (5)
O3—Zn1—O5	88.79 (5)
O3—Zn1—O1ⁱ	89.96 (5)
O5—Zn1—O1ⁱ	93.21 (5)
O3—Zn1—O1	90.04 (5)
O5—Zn1—O1	86.79 (5)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O2	0.85 (2)	2.15 (2)	2.921 (2)	150.0 (17)
N3—H3A⋯O5ⁱⁱ	0.87 (2)	2.09 (2)	2.958 (2)	171.0 (19)
Symmetry code: (ii) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024549/hg2413sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024549/hg2413Isup2.hkl

checkCIF report

Comment top

Acetic acid is versatile ligand which can function in monodentate or bidentate modes in metal complexes (Baker & Norman, 2004; Lis et al., 2005; Stadie et al., 2007). Here, we report the crystal structure of the title compound, (I), in which three Zn^II ions are bridged by three acetic acid ligands.

The middle Zn atom in (I) (Fig. 1) has a distorted octahedral coordination geometry involving six O atoms of six acetic acid ligands. The Zn—O bonds lengths are between 1.9588 (12) and 2.1237 (12)Å (Table 1). The End Zn^II ion is coordinated by one N atom of 2-amino-4-methyl-7-chloro-1,8-naphthyridine and three O atoms of three acetic acid ligands, and has a distorted tetrahedron coordination geometry. The distance of two neighboring Zn^II ions separated by two O atoms of each two acetate bridging ligands and one O atoms of one acetate bridging ligand is 3.245 (3) Å.

Related literature top

For related literature, see: Baker & Norman (2004); Lis et al. (2005); Stadie et al. (2007).

Experimental top

A 10 ml dichloromethane solution of 2-amino-5-methyl-7-chloro-1,8-naphthyridine (0.039 g, 0.2 mmol) was added to a 20 mL dichloromethane solution of Zn(CH₃COO)₂ (0.055 g, 0.3 mmol) under an N₂ atmosphere. The mixture was stirred for 10 h. Colorless crystals suitable for X-ray diffraction were formed by vapour diffusion of diethyl ethyl ether into dichloromethane solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level. (Symmetry code: 1 - x, 1 - y, 1 - z).

Hexa-µ₂-acetato-1:2κ⁴O:O';1:2κ²O:O;2:3κ⁴O:O';2:3κ²O:O- bis(2-amino-7-chloro-5-methyl-1,8-naphthyridine)-1κN¹,3κN¹- trizinc(II) top

Crystal data top

[Zn₃(C₂H₃O₂)₆(C₉H₈ClN₃)₂]	Z = 1
M_r = 937.64	F(000) = 476
Triclinic, P1	D_x = 1.739 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 9.1978 (12) Å	Cell parameters from 2625 reflections
b = 9.2108 (13) Å	θ = 2.5–25.0°
c = 12.0457 (16) Å	µ = 2.21 mm⁻¹
α = 93.602 (3)°	T = 113 K
β = 91.685 (2)°	Prism, colorless
γ = 118.247 (2)°	0.12 × 0.08 × 0.02 mm
V = 895.2 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4221 independent reflections
Radiation source: fine-focus sealed tube	3495 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.782, T_max = 0.956	k = −12→12
11008 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0354P)²] where P = (F_o² + 2F_c²)/3
4221 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Zn₃(C₂H₃O₂)₆(C₉H₈ClN₃)₂]	γ = 118.247 (2)°
M_r = 937.64	V = 895.2 (2) Å³
Triclinic, P1	Z = 1
a = 9.1978 (12) Å	Mo Kα radiation
b = 9.2108 (13) Å	µ = 2.21 mm⁻¹
c = 12.0457 (16) Å	T = 113 K
α = 93.602 (3)°	0.12 × 0.08 × 0.02 mm
β = 91.685 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4221 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3495 reflections with I > 2σ(I)
T_min = 0.782, T_max = 0.956	R_int = 0.030
11008 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.36 e Å⁻³
4221 reflections	Δρ_min = −0.65 e Å⁻³
253 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. 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
Zn1	0.5000	0.5000	0.5000	0.01215 (8)
Zn2	0.81766 (2)	0.76297 (2)	0.660723 (16)	0.01398 (7)
Cl1	0.47109 (6)	0.69320 (6)	0.93855 (4)	0.03122 (13)
N1	0.75010 (17)	0.85718 (17)	0.85071 (12)	0.0158 (3)
N2	0.97997 (17)	0.97283 (17)	0.75522 (12)	0.0136 (3)
N3	1.20715 (19)	1.0819 (2)	0.64915 (13)	0.0181 (3)
H3A	1.299 (3)	1.168 (3)	0.6360 (17)	0.024 (6)*
H3B	1.164 (2)	0.998 (2)	0.6007 (17)	0.018 (5)*
C1	0.6629 (2)	0.8670 (2)	0.93115 (15)	0.0179 (4)
C2	0.7103 (2)	1.0020 (2)	1.01047 (15)	0.0182 (4)
H2	0.6394	0.9999	1.0669	0.022*
C3	0.8637 (2)	1.1386 (2)	1.00414 (14)	0.0163 (4)
C4	0.9626 (2)	1.1348 (2)	0.91812 (14)	0.0143 (3)
C5	0.8998 (2)	0.9917 (2)	0.84338 (14)	0.0138 (3)
C6	1.1288 (2)	1.0979 (2)	0.73619 (14)	0.0140 (4)
C7	1.2028 (2)	1.2477 (2)	0.80965 (15)	0.0174 (4)
H7	1.3084	1.3350	0.7962	0.021*
C8	1.1228 (2)	1.2645 (2)	0.89753 (15)	0.0170 (4)
H8	1.1731	1.3632	0.9462	0.020*
C9	0.9208 (2)	1.2883 (2)	1.08722 (16)	0.0222 (4)
H9A	0.9206	1.3797	1.0499	0.033*
H9B	1.0331	1.3213	1.1178	0.033*
H9C	0.8458	1.2608	1.1478	0.033*
C10	0.8902 (2)	0.6534 (2)	0.45903 (14)	0.0152 (4)
C11	1.0029 (2)	0.6306 (2)	0.38019 (16)	0.0206 (4)
H11A	1.0654	0.5849	0.4187	0.031*
H11B	1.0799	0.7376	0.3545	0.031*
H11C	0.9369	0.5543	0.3160	0.031*
C12	0.5768 (2)	0.8498 (2)	0.60578 (15)	0.0195 (4)
C13	0.4045 (2)	0.8233 (3)	0.59278 (19)	0.0314 (5)
H13A	0.3986	0.9177	0.6303	0.047*
H13B	0.3298	0.7220	0.6261	0.047*
H13C	0.3714	0.8128	0.5134	0.047*
C14	0.3533 (2)	0.5867 (2)	0.29542 (14)	0.0132 (3)
C15	0.3642 (2)	0.7221 (2)	0.22734 (15)	0.0200 (4)
H15A	0.3524	0.8054	0.2753	0.030*
H15B	0.2755	0.6755	0.1677	0.030*
H15C	0.4716	0.7738	0.1946	0.030*
O1	0.73730 (14)	0.56434 (14)	0.44255 (10)	0.0174 (3)
O2	0.95980 (15)	0.76262 (15)	0.54110 (10)	0.0191 (3)
O3	0.59970 (14)	0.72059 (14)	0.60042 (10)	0.0170 (3)
O4	0.69633 (18)	0.98977 (17)	0.62159 (15)	0.0385 (4)
O5	0.46887 (14)	0.62359 (14)	0.36908 (10)	0.0165 (3)
O6	0.22937 (14)	0.44604 (14)	0.27489 (10)	0.0178 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01022 (14)	0.01115 (14)	0.01260 (15)	0.00360 (11)	−0.00109 (10)	−0.00257 (11)
Zn2	0.01081 (11)	0.01109 (11)	0.01601 (12)	0.00248 (8)	−0.00174 (8)	−0.00236 (8)
Cl1	0.0224 (2)	0.0204 (2)	0.0333 (3)	−0.0039 (2)	0.0130 (2)	−0.0047 (2)
N1	0.0152 (7)	0.0122 (7)	0.0145 (8)	0.0023 (6)	−0.0001 (6)	−0.0009 (6)
N2	0.0133 (7)	0.0104 (7)	0.0141 (7)	0.0034 (6)	0.0006 (6)	0.0003 (6)
N3	0.0130 (8)	0.0141 (8)	0.0220 (9)	0.0021 (7)	0.0041 (6)	0.0008 (7)
C1	0.0159 (9)	0.0140 (9)	0.0173 (9)	0.0017 (7)	0.0027 (7)	0.0013 (7)
C2	0.0204 (9)	0.0165 (9)	0.0155 (9)	0.0070 (8)	0.0031 (7)	0.0012 (7)
C3	0.0204 (9)	0.0144 (9)	0.0145 (9)	0.0091 (8)	−0.0036 (7)	−0.0009 (7)
C4	0.0143 (8)	0.0112 (8)	0.0153 (9)	0.0049 (7)	−0.0038 (7)	−0.0006 (6)
C5	0.0134 (8)	0.0128 (8)	0.0135 (9)	0.0051 (7)	−0.0013 (7)	0.0009 (7)
C6	0.0128 (8)	0.0110 (8)	0.0170 (9)	0.0049 (7)	−0.0020 (7)	0.0011 (7)
C7	0.0118 (8)	0.0103 (8)	0.0248 (10)	0.0012 (7)	−0.0015 (7)	0.0002 (7)
C8	0.0159 (9)	0.0097 (8)	0.0214 (9)	0.0036 (7)	−0.0039 (7)	−0.0024 (7)
C9	0.0241 (10)	0.0176 (9)	0.0215 (10)	0.0081 (8)	−0.0021 (8)	−0.0053 (8)
C10	0.0165 (8)	0.0127 (8)	0.0164 (9)	0.0065 (7)	0.0019 (7)	0.0038 (7)
C11	0.0164 (9)	0.0215 (9)	0.0231 (10)	0.0083 (8)	0.0052 (7)	0.0011 (8)
C12	0.0227 (9)	0.0160 (9)	0.0190 (10)	0.0091 (8)	−0.0009 (7)	−0.0018 (7)
C13	0.0235 (10)	0.0231 (11)	0.0490 (14)	0.0136 (9)	−0.0034 (10)	−0.0060 (9)
C14	0.0136 (8)	0.0141 (8)	0.0128 (8)	0.0073 (7)	0.0042 (6)	−0.0010 (7)
C15	0.0206 (9)	0.0181 (9)	0.0201 (10)	0.0078 (8)	0.0021 (7)	0.0058 (7)
O1	0.0117 (6)	0.0176 (6)	0.0191 (7)	0.0044 (5)	0.0018 (5)	−0.0026 (5)
O2	0.0139 (6)	0.0172 (6)	0.0195 (7)	0.0027 (5)	0.0008 (5)	−0.0041 (5)
O3	0.0150 (6)	0.0134 (6)	0.0223 (7)	0.0079 (5)	−0.0053 (5)	−0.0076 (5)
O4	0.0261 (8)	0.0178 (7)	0.0673 (11)	0.0077 (6)	−0.0081 (7)	0.0025 (7)
O5	0.0133 (6)	0.0132 (6)	0.0179 (7)	0.0022 (5)	−0.0016 (5)	0.0020 (5)
O6	0.0151 (6)	0.0125 (6)	0.0214 (7)	0.0037 (5)	−0.0038 (5)	−0.0014 (5)

Geometric parameters (Å, º) top

Zn1—O3	2.0724 (12)	C7—C8	1.349 (2)
Zn1—O3ⁱ	2.0724 (12)	C7—H7	0.9500
Zn1—O5ⁱ	2.0910 (12)	C8—H8	0.9500
Zn1—O5	2.0910 (12)	C9—H9A	0.9800
Zn1—O1ⁱ	2.1237 (12)	C9—H9B	0.9800
Zn1—O1	2.1237 (12)	C9—H9C	0.9800
Zn2—O3	1.9588 (12)	C10—O1	1.249 (2)
Zn2—O2	1.9748 (12)	C10—O2	1.275 (2)
Zn2—O6ⁱ	1.9783 (12)	C10—C11	1.504 (2)
Zn2—N2	2.0379 (14)	C11—H11A	0.9800
Cl1—C1	1.7428 (18)	C11—H11B	0.9800
N1—C1	1.302 (2)	C11—H11C	0.9800
N1—C5	1.358 (2)	C12—O4	1.234 (2)
N2—C6	1.346 (2)	C12—O3	1.301 (2)
N2—C5	1.359 (2)	C12—C13	1.487 (2)
N3—C6	1.329 (2)	C13—H13A	0.9800
N3—H3A	0.87 (2)	C13—H13B	0.9800
N3—H3B	0.85 (2)	C13—H13C	0.9800
C1—C2	1.401 (2)	C14—O6	1.259 (2)
C2—C3	1.385 (2)	C14—O5	1.264 (2)
C2—H2	0.9500	C14—C15	1.502 (2)
C3—C4	1.408 (2)	C15—H15A	0.9800
C3—C9	1.512 (2)	C15—H15B	0.9800
C4—C5	1.407 (2)	C15—H15C	0.9800
C4—C8	1.433 (2)	O6—Zn2ⁱ	1.9783 (12)
C6—C7	1.439 (2)

O3—Zn1—O3ⁱ	180.0	C8—C7—C6	120.23 (16)
O3—Zn1—O5ⁱ	91.21 (5)	C8—C7—H7	119.9
O3ⁱ—Zn1—O5ⁱ	88.79 (5)	C6—C7—H7	119.9
O3—Zn1—O5	88.79 (5)	C7—C8—C4	120.55 (16)
O3ⁱ—Zn1—O5	91.21 (5)	C7—C8—H8	119.7
O5ⁱ—Zn1—O5	180.000 (1)	C4—C8—H8	119.7
O3—Zn1—O1ⁱ	89.96 (5)	C3—C9—H9A	109.5
O3ⁱ—Zn1—O1ⁱ	90.04 (5)	C3—C9—H9B	109.5
O5ⁱ—Zn1—O1ⁱ	86.79 (5)	H9A—C9—H9B	109.5
O5—Zn1—O1ⁱ	93.21 (5)	C3—C9—H9C	109.5
O3—Zn1—O1	90.04 (5)	H9A—C9—H9C	109.5
O3ⁱ—Zn1—O1	89.96 (5)	H9B—C9—H9C	109.5
O5ⁱ—Zn1—O1	93.21 (5)	O1—C10—O2	124.22 (16)
O5—Zn1—O1	86.79 (5)	O1—C10—C11	119.27 (15)
O1ⁱ—Zn1—O1	180.0	O2—C10—C11	116.48 (15)
O3—Zn2—O2	111.65 (5)	C10—C11—H11A	109.5
O3—Zn2—O6ⁱ	103.18 (5)	C10—C11—H11B	109.5
O2—Zn2—O6ⁱ	100.45 (5)	H11A—C11—H11B	109.5
O3—Zn2—N2	124.29 (5)	C10—C11—H11C	109.5
O2—Zn2—N2	99.92 (5)	H11A—C11—H11C	109.5
O6ⁱ—Zn2—N2	115.01 (6)	H11B—C11—H11C	109.5
C1—N1—C5	116.26 (15)	O4—C12—O3	120.09 (17)
C6—N2—C5	118.94 (14)	O4—C12—C13	121.64 (17)
C6—N2—Zn2	132.49 (12)	O3—C12—C13	118.27 (16)
C5—N2—Zn2	107.49 (10)	C12—C13—H13A	109.5
C6—N3—H3A	117.2 (13)	C12—C13—H13B	109.5
C6—N3—H3B	122.8 (13)	H13A—C13—H13B	109.5
H3A—N3—H3B	119.2 (19)	C12—C13—H13C	109.5
N1—C1—C2	125.99 (16)	H13A—C13—H13C	109.5
N1—C1—Cl1	115.41 (13)	H13B—C13—H13C	109.5
C2—C1—Cl1	118.60 (14)	O6—C14—O5	125.42 (16)
C3—C2—C1	117.92 (16)	O6—C14—C15	117.28 (16)
C3—C2—H2	121.0	O5—C14—C15	117.30 (15)
C1—C2—H2	121.0	C14—C15—H15A	109.5
C2—C3—C4	118.36 (16)	C14—C15—H15B	109.5
C2—C3—C9	120.18 (16)	H15A—C15—H15B	109.5
C4—C3—C9	121.44 (16)	C14—C15—H15C	109.5
C5—C4—C3	118.00 (15)	H15A—C15—H15C	109.5
C5—C4—C8	115.72 (15)	H15B—C15—H15C	109.5
C3—C4—C8	126.28 (16)	C10—O1—Zn1	146.79 (11)
N1—C5—N2	112.32 (14)	C10—O2—Zn2	116.68 (11)
N1—C5—C4	123.46 (15)	C12—O3—Zn2	114.47 (11)
N2—C5—C4	124.21 (15)	C12—O3—Zn1	134.69 (11)
N3—C6—N2	119.47 (15)	Zn2—O3—Zn1	107.19 (5)
N3—C6—C7	120.21 (16)	C14—O5—Zn1	133.41 (11)
N2—C6—C7	120.32 (15)	C14—O6—Zn2ⁱ	128.40 (12)

O3—Zn2—N2—C6	−112.51 (15)	C11—C10—O1—Zn1	177.44 (14)
O2—Zn2—N2—C6	12.43 (16)	O3—Zn1—O1—C10	18.1 (2)
O6ⁱ—Zn2—N2—C6	118.98 (15)	O3ⁱ—Zn1—O1—C10	−161.9 (2)
O3—Zn2—N2—C5	55.10 (13)	O5ⁱ—Zn1—O1—C10	−73.1 (2)
O2—Zn2—N2—C5	−179.96 (11)	O5—Zn1—O1—C10	106.9 (2)
O6ⁱ—Zn2—N2—C5	−73.41 (12)	O1—C10—O2—Zn2	10.3 (2)
C5—N1—C1—C2	−0.7 (3)	C11—C10—O2—Zn2	−168.04 (12)
C5—N1—C1—Cl1	179.79 (13)	O3—Zn2—O2—C10	−39.80 (14)
N1—C1—C2—C3	−0.1 (3)	O6ⁱ—Zn2—O2—C10	69.02 (13)
Cl1—C1—C2—C3	179.40 (14)	N2—Zn2—O2—C10	−173.03 (12)
C1—C2—C3—C4	0.5 (3)	O4—C12—O3—Zn2	16.8 (2)
C1—C2—C3—C9	179.64 (16)	C13—C12—O3—Zn2	−163.00 (14)
C2—C3—C4—C5	−0.1 (2)	O4—C12—O3—Zn1	−138.26 (16)
C9—C3—C4—C5	−179.27 (16)	C13—C12—O3—Zn1	41.9 (3)
C2—C3—C4—C8	179.11 (17)	O2—Zn2—O3—C12	−106.56 (12)
C9—C3—C4—C8	0.0 (3)	O6ⁱ—Zn2—O3—C12	146.38 (12)
C1—N1—C5—N2	−178.05 (15)	N2—Zn2—O3—C12	13.12 (15)
C1—N1—C5—C4	1.1 (3)	O2—Zn2—O3—Zn1	55.16 (7)
C6—N2—C5—N1	178.72 (15)	O6ⁱ—Zn2—O3—Zn1	−51.90 (7)
Zn2—N2—C5—N1	9.14 (17)	N2—Zn2—O3—Zn1	174.84 (5)
C6—N2—C5—C4	−0.5 (2)	O5ⁱ—Zn1—O3—C12	−148.65 (17)
Zn2—N2—C5—C4	−170.03 (14)	O5—Zn1—O3—C12	31.35 (17)
C3—C4—C5—N1	−0.7 (3)	O1ⁱ—Zn1—O3—C12	−61.86 (17)
C8—C4—C5—N1	179.97 (16)	O1—Zn1—O3—C12	118.14 (17)
C3—C4—C5—N2	178.36 (15)	O5ⁱ—Zn1—O3—Zn2	55.03 (6)
C8—C4—C5—N2	−1.0 (3)	O5—Zn1—O3—Zn2	−124.97 (6)
C5—N2—C6—N3	−178.89 (16)	O1ⁱ—Zn1—O3—Zn2	141.82 (6)
Zn2—N2—C6—N3	−12.4 (2)	O1—Zn1—O3—Zn2	−38.18 (6)
C5—N2—C6—C7	1.3 (2)	O6—C14—O5—Zn1	−10.3 (3)
Zn2—N2—C6—C7	167.75 (12)	C15—C14—O5—Zn1	169.19 (11)
N3—C6—C7—C8	179.50 (17)	O3—Zn1—O5—C14	−137.70 (15)
N2—C6—C7—C8	−0.7 (3)	O3ⁱ—Zn1—O5—C14	42.30 (15)
C6—C7—C8—C4	−0.8 (3)	O1ⁱ—Zn1—O5—C14	−47.81 (15)
C5—C4—C8—C7	1.6 (3)	O1—Zn1—O5—C14	132.19 (15)
C3—C4—C8—C7	−177.70 (17)	O5—C14—O6—Zn2ⁱ	−5.4 (3)
O2—C10—O1—Zn1	−0.9 (3)	C15—C14—O6—Zn2ⁱ	175.15 (11)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2	0.85 (2)	2.15 (2)	2.921 (2)	150.0 (17)
N3—H3A···O5ⁱⁱ	0.87 (2)	2.09 (2)	2.958 (2)	171.0 (19)

Symmetry code: (ii) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn₃(C₂H₃O₂)₆(C₉H₈ClN₃)₂]
M_r	937.64
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.1978 (12), 9.2108 (13), 12.0457 (16)
α, β, γ (°)	93.602 (3), 91.685 (2), 118.247 (2)
V (Å³)	895.2 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.21
Crystal size (mm)	0.12 × 0.08 × 0.02

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.782, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	11008, 4221, 3495
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.065, 1.01
No. of reflections	4221
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.65

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O3	2.0724 (12)	Zn2—O3	1.9588 (12)
Zn1—O5	2.0910 (12)	Zn2—O2	1.9748 (12)
Zn1—O1	2.1237 (12)	Zn2—N2	2.0379 (14)

O3—Zn1—O5ⁱ	91.21 (5)	O5—Zn1—O1ⁱ	93.21 (5)
O3—Zn1—O5	88.79 (5)	O3—Zn1—O1	90.04 (5)
O3—Zn1—O1ⁱ	89.96 (5)	O5—Zn1—O1	86.79 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2	0.85 (2)	2.15 (2)	2.921 (2)	150.0 (17)
N3—H3A···O5ⁱⁱ	0.87 (2)	2.09 (2)	2.958 (2)	171.0 (19)

Symmetry code: (ii) −x+2, −y+2, −z+1.

Acknowledgements

We thank Henan Agricultural University for the generous support of this study.

References

Baker, R. S. & Norman, R. E. (2004). Acta Cryst. E60, m1761–m1763. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lis, T., Kinzhybalo, V. & Zieba, K. (2005). Acta Cryst. E61, m2382–m2384. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stadie, N. P., Sanchez-Smith, R. & Groy, T. L. (2007). Acta Cryst. E63, m2153–m2154. Web of Science CSD CrossRef IUCr Journals Google Scholar

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