(Acetato-κO)(acetato-κ2O,O′)[2-(3,5-di­methyl-1H-pyrazol-1-yl-κN2)quinoline-κN]zinc(II)

Najib, M.H. bin; Tan, A.L.; Young, D.J.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812025664

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m897-m898

https://doi.org/10.1107/S1600536812025664

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(Acetato-κO)(acetato-κ²O,O′)[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)quinoline-κN]zinc(II)

Muhd. Hidayat bin Najib,^a Ai Ling Tan,^a David J. Young,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aFaculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 4 June 2012; accepted 5 June 2012; online 13 June 2012)

The Zn^II atom in the title compound, [Zn(C₂H₃O₂)₂(C₁₄H₁₃N₃)], is coordinated by an N₂O₃ donor set defined by the quinolinyl- and pyrazolyl-N atoms of the chelating heterocyclic ligand, and three carboxylate-O atoms derived from the monodentate and bidentate carboxylate ligands. Distortions from the ideal square-pyramidal coordination geometry relate to the restricted bite angle of the chelating ligands, i.e. O—Zn—O = 59.65 (5) and N—Zn—N = 76.50 (6)°, and the close approach of the non-coordinating carbonyl atom [Zn⋯O = 2.858 (2) Å]. In the crystal, molecules are consolidated into a three-dimensional architecture by C—H⋯O interactions

Related literature

For background to luminescent coordination complexes, see: Bai et al. (2011 , 2012 ); Chou et al. (2011 ); Wang (2001 ). For the synthesis, see: Savel'eva et al. (2009 ); Scott et al. (1952 ). For the structure of the dichlorido analogue, see: Najib et al. (2012 ). For additional geometric analysis, see: Addison et al. (1984 ).

Experimental

Crystal data

[Zn(C₂H₃O₂)₂(C₁₄H₁₃N₃)]
M_r = 406.73
Triclinic, $[P \overline 1]$
a = 7.6586 (4) Å
b = 10.7334 (6) Å
c = 11.5772 (4) Å
α = 69.437 (4)°
β = 81.546 (3)°
γ = 72.736 (4)°
V = 849.93 (7) Å³
Z = 2
Cu Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.617, T_max = 1.000
6205 measured reflections
3498 independent reflections
3322 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.03
3498 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn—O1	2.0388 (14)
Zn—O2	2.3240 (15)
Zn—O3	1.9397 (13)
Zn—N1	2.0570 (15)
Zn—N3	2.1460 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O3ⁱ	0.98	2.57	3.544 (2)	176
C5—H5A⋯O2ⁱⁱ	0.98	2.60	3.417 (3)	141
C7—H7⋯O2ⁱⁱ	0.95	2.56	3.235 (2)	128
C9—H9C⋯O4ⁱⁱⁱ	0.98	2.36	3.274 (2)	156
C12—H12⋯O1^iv	0.95	2.51	3.310 (2)	142
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y+1, -z+2; (iv) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025664/hb6839sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025664/hb6839Isup2.hkl

checkCIF report

Comment top

Many Zn^II complexes of nitrogen-containing ligands exhibit intense emission at room temperature (Wang, 2001; Chou et al., 2011; Bai et al., 2011; Bai et al., 2012). The title compound was prepared as part of a series of potentially luminescent coordination complexes for use in organic light emitting diode (OLED) materials. We have previously reported the solid-state structure of dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-2)quinoline]zinc(II) (Najib et al., 2012), i.e. the dichlorido analogue of the title compound, (I).

The Zn^II atom in (I), Fig. 1, is chelated by quinolinyl- and pyrazolyl-N atoms of the heterocyclic ligand, and three carboxylate-O atoms derived from the monodentate and bidentate carboxylates, Table 1. The resulting N₂O₃ donor set defines an approximate square pyramid with the Zn atom lying 0.8591 (8) Å out of the plane defined by the O1, O2, N1 and N3 atoms [r.m.s. deviation = 0.1122 Å] in the direction of the O3 atom. The assignment of coordination geometry is quantified by the value of τ = 0.06 which compares to the τ values of 0.0 and 1.0 for ideal square pyramidal and trigonal bipyramidal geometries, respectively (Addison et al., 1984). Significant distortions in the coordination geometry are apparent owing the restricted bite angles of the chelating ligands, i.e. O1—Zn—O2 = 59.65 (5)° and N1—Zn—N3 = 76.50 (6)°. Further distortions are related to the relatively close approach of the O4 atom to Zn, the Zn···O4 separation is 2.858 (2) Å. The five-membered chelate ring is approximately planar with a r.m.s. deviation = 0.088 Å and with maximum deviations of 0.074 (2) and -0.057 (1) Å for the N1 and Zn atoms, respectively. The bidentate ligand is planar with the dihedral angle between the quinolinyl and pyrazolyl rings being 2.14 (6)°.

Molecules are consolidated into a three-dimensional architecture by C—H···O interactions, Fig. 2 and Table 2.

Related literature top

For background to luminescent coordination complexes, see: Bai et al. (2011, 2012); Chou et al. (2011); Wang (2001). For the synthesis, see: Savel'eva et al. (2009); Scott et al. (1952). For the structure of the dichlorido analogue, see: Najib et al. (2012). For additional geometric analysis, see: Addison et al. (1984).

Experimental top

The title compound was prepared by modification of a literature procedure (Savel'eva et al., 2009) and as previously described for the corresponding dichloride (Najib et al., 2012). 3,5-Dimethyl-1-(2'-quinolyl)pyrazole (0.0908 g), prepared as in the literature (Scott et al., 1952), in a mixture of EtOH (4 ml) and CH₂Cl₂ (2 ml) was added to a suspension of Zn(OAc)₂ (0.0764 g) in EtOH (8 ml). The solution was heated to dissolve the Zn(OAc)₂. Light-brown prisms formed over a period of 16 h and were collected by filtration, washed with EtOH and recrystallized from CH₂Cl₂/hexane. Yield 0.0733 g (44%). M.pt: 474 K. IR v/cm^-1: 2925, 2864, 2365, 2323, 1604, 1507, 1424, 1388.

Structure description top

Molecules are consolidated into a three-dimensional architecture by C—H···O interactions, Fig. 2 and Table 2.

For background to luminescent coordination complexes, see: Bai et al. (2011, 2012); Chou et al. (2011); Wang (2001). For the synthesis, see: Savel'eva et al. (2009); Scott et al. (1952). For the structure of the dichlorido analogue, see: Najib et al. (2012). For additional geometric analysis, see: Addison et al. (1984).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the unit-cell contents of (I) in projection down the c axis. The C—H···O interactions are shown as orange dashed lines.

(Acetato-κO)(acetato-κ²O,O')[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)quinoline-κN]zinc(II) top

Crystal data top

[Zn(C₂H₃O₂)₂(C₁₄H₁₃N₃)]	Z = 2
M_r = 406.73	F(000) = 420
Triclinic, P1	D_x = 1.589 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.6586 (4) Å	Cell parameters from 3775 reflections
b = 10.7334 (6) Å	θ = 4.6–76.3°
c = 11.5772 (4) Å	µ = 2.27 mm⁻¹
α = 69.437 (4)°	T = 100 K
β = 81.546 (3)°	Prism, light-brown
γ = 72.736 (4)°	0.25 × 0.15 × 0.05 mm
V = 849.93 (7) Å³

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3498 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3322 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.6°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→13
T_min = 0.617, T_max = 1.000	l = −11→14
6205 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0448P)² + 0.5376P] where P = (F_o² + 2F_c²)/3
3498 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Zn(C₂H₃O₂)₂(C₁₄H₁₃N₃)]	γ = 72.736 (4)°
M_r = 406.73	V = 849.93 (7) Å³
Triclinic, P1	Z = 2
a = 7.6586 (4) Å	Cu Kα radiation
b = 10.7334 (6) Å	µ = 2.27 mm⁻¹
c = 11.5772 (4) Å	T = 100 K
α = 69.437 (4)°	0.25 × 0.15 × 0.05 mm
β = 81.546 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3498 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3322 reflections with I > 2σ(I)
T_min = 0.617, T_max = 1.000	R_int = 0.021
6205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	Δρ_max = 0.67 e Å⁻³
3498 reflections	Δρ_min = −0.45 e Å⁻³
239 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
Zn	0.81157 (3)	0.72065 (2)	0.729830 (19)	0.01539 (9)
O1	0.54802 (18)	0.81205 (15)	0.67857 (12)	0.0237 (3)
O2	0.7235 (2)	0.72283 (17)	0.54526 (14)	0.0333 (3)
O3	0.97606 (19)	0.83912 (14)	0.66803 (13)	0.0251 (3)
O4	0.8163 (2)	0.95459 (18)	0.79237 (13)	0.0346 (4)
N1	0.9903 (2)	0.53183 (15)	0.73964 (13)	0.0157 (3)
N2	0.9663 (2)	0.42401 (15)	0.84284 (13)	0.0148 (3)
N3	0.76154 (19)	0.59226 (15)	0.91411 (13)	0.0147 (3)
C1	0.5715 (3)	0.78835 (18)	0.57607 (17)	0.0191 (3)
C2	0.4136 (3)	0.8434 (2)	0.49227 (18)	0.0247 (4)
H2A	0.4333	0.7891	0.4366	0.037*
H2B	0.4053	0.9401	0.4436	0.037*
H2C	0.2996	0.8367	0.5421	0.037*
C3	0.9376 (3)	0.93922 (19)	0.71118 (16)	0.0203 (4)
C4	1.0519 (3)	1.0407 (2)	0.65732 (18)	0.0238 (4)
H4A	1.0008	1.1202	0.6865	0.036*
H4B	1.0515	1.0719	0.5670	0.036*
H4C	1.1778	0.9961	0.6834	0.036*
C5	1.1702 (3)	0.56456 (19)	0.54237 (16)	0.0216 (4)
H5A	1.1823	0.5196	0.4800	0.032*
H5B	1.2888	0.5773	0.5503	0.032*
H5C	1.0801	0.6546	0.5171	0.032*
C6	1.1083 (2)	0.47655 (18)	0.66347 (16)	0.0169 (3)
C7	1.1602 (2)	0.33201 (18)	0.71639 (16)	0.0172 (3)
H7	1.2427	0.2686	0.6804	0.021*
C8	1.0696 (2)	0.29988 (18)	0.82920 (16)	0.0162 (3)
C9	1.0774 (3)	0.15864 (18)	0.91825 (16)	0.0197 (3)
H9A	1.1598	0.0897	0.8838	0.029*
H9B	0.9545	0.1441	0.9330	0.029*
H9C	1.1231	0.1494	0.9964	0.029*
C10	0.8445 (2)	0.45914 (18)	0.93770 (15)	0.0146 (3)
C11	0.8173 (2)	0.35645 (18)	1.04951 (16)	0.0175 (3)
H11	0.8819	0.2624	1.0634	0.021*
C12	0.6956 (2)	0.39558 (19)	1.13728 (16)	0.0186 (3)
H12	0.6735	0.3279	1.2127	0.022*
C13	0.6026 (2)	0.53597 (18)	1.11662 (16)	0.0165 (3)
C14	0.4758 (2)	0.5825 (2)	1.20508 (16)	0.0197 (4)
H14	0.4464	0.5176	1.2803	0.024*
C15	0.3960 (2)	0.7202 (2)	1.18233 (17)	0.0212 (4)
H15	0.3129	0.7509	1.2423	0.025*
C16	0.4366 (2)	0.81699 (19)	1.06979 (17)	0.0204 (4)
H16	0.3813	0.9126	1.0554	0.025*
C17	0.5549 (2)	0.77526 (18)	0.98073 (16)	0.0183 (3)
H17	0.5788	0.8414	0.9047	0.022*
C18	0.6406 (2)	0.63361 (18)	1.00311 (15)	0.0157 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.01744 (13)	0.01236 (13)	0.01501 (13)	−0.00462 (9)	−0.00080 (9)	−0.00227 (9)
O1	0.0225 (7)	0.0315 (7)	0.0164 (6)	−0.0077 (6)	−0.0021 (5)	−0.0058 (5)
O2	0.0279 (8)	0.0360 (8)	0.0346 (8)	0.0037 (6)	−0.0070 (6)	−0.0178 (7)
O3	0.0254 (7)	0.0173 (6)	0.0335 (7)	−0.0087 (5)	−0.0018 (6)	−0.0067 (5)
O4	0.0350 (8)	0.0474 (9)	0.0219 (7)	−0.0177 (7)	0.0070 (6)	−0.0096 (6)
N1	0.0193 (7)	0.0134 (7)	0.0132 (6)	−0.0059 (6)	−0.0005 (5)	−0.0015 (5)
N2	0.0172 (7)	0.0121 (6)	0.0133 (6)	−0.0044 (5)	−0.0012 (5)	−0.0012 (5)
N3	0.0159 (7)	0.0141 (7)	0.0139 (6)	−0.0045 (5)	−0.0019 (5)	−0.0034 (5)
C1	0.0218 (9)	0.0131 (8)	0.0210 (8)	−0.0073 (7)	−0.0013 (7)	−0.0013 (6)
C2	0.0265 (10)	0.0261 (10)	0.0220 (9)	−0.0074 (8)	−0.0060 (7)	−0.0062 (7)
C3	0.0231 (9)	0.0210 (9)	0.0125 (7)	−0.0048 (7)	−0.0062 (6)	0.0009 (6)
C4	0.0294 (10)	0.0212 (9)	0.0253 (9)	−0.0116 (8)	0.0022 (7)	−0.0103 (7)
C5	0.0258 (9)	0.0205 (9)	0.0179 (8)	−0.0085 (7)	0.0030 (7)	−0.0053 (7)
C6	0.0178 (8)	0.0186 (8)	0.0159 (8)	−0.0062 (7)	−0.0010 (6)	−0.0063 (7)
C7	0.0180 (8)	0.0163 (8)	0.0188 (8)	−0.0048 (6)	−0.0019 (6)	−0.0070 (7)
C8	0.0173 (8)	0.0139 (8)	0.0184 (8)	−0.0037 (6)	−0.0040 (6)	−0.0055 (6)
C9	0.0232 (9)	0.0134 (8)	0.0201 (8)	−0.0032 (7)	−0.0030 (7)	−0.0034 (7)
C10	0.0153 (8)	0.0150 (8)	0.0139 (7)	−0.0056 (6)	−0.0022 (6)	−0.0031 (6)
C11	0.0204 (8)	0.0145 (8)	0.0167 (8)	−0.0056 (6)	−0.0020 (6)	−0.0026 (6)
C12	0.0205 (8)	0.0183 (8)	0.0148 (8)	−0.0075 (7)	−0.0015 (6)	−0.0007 (6)
C13	0.0151 (8)	0.0196 (8)	0.0161 (8)	−0.0071 (7)	−0.0018 (6)	−0.0049 (7)
C14	0.0187 (8)	0.0255 (9)	0.0152 (8)	−0.0078 (7)	0.0001 (6)	−0.0058 (7)
C15	0.0166 (8)	0.0288 (10)	0.0206 (8)	−0.0053 (7)	0.0002 (6)	−0.0118 (7)
C16	0.0171 (8)	0.0205 (9)	0.0246 (9)	−0.0034 (7)	−0.0029 (7)	−0.0089 (7)
C17	0.0177 (8)	0.0168 (8)	0.0203 (8)	−0.0049 (7)	−0.0027 (6)	−0.0049 (7)
C18	0.0151 (8)	0.0178 (8)	0.0150 (8)	−0.0059 (6)	−0.0024 (6)	−0.0041 (6)

Geometric parameters (Å, º) top

Zn—O1	2.0388 (14)	C5—H5B	0.9800
Zn—O2	2.3240 (15)	C5—H5C	0.9800
Zn—O3	1.9397 (13)	C6—C7	1.406 (2)
Zn—N1	2.0570 (15)	C7—C8	1.366 (2)
Zn—N3	2.1460 (14)	C7—H7	0.9500
O1—C1	1.276 (2)	C8—C9	1.494 (2)
O2—C1	1.243 (2)	C9—H9A	0.9800
O3—C3	1.279 (2)	C9—H9B	0.9800
O4—C3	1.239 (2)	C9—H9C	0.9800
N1—C6	1.327 (2)	C10—C11	1.410 (2)
N1—N2	1.3752 (19)	C11—C12	1.366 (3)
N2—C8	1.383 (2)	C11—H11	0.9500
N2—C10	1.414 (2)	C12—C13	1.412 (3)
N3—C10	1.326 (2)	C12—H12	0.9500
N3—C18	1.383 (2)	C13—C18	1.418 (2)
C1—C2	1.507 (3)	C13—C14	1.422 (2)
C2—H2A	0.9800	C14—C15	1.365 (3)
C2—H2B	0.9800	C14—H14	0.9500
C2—H2C	0.9800	C15—C16	1.413 (3)
C3—C4	1.507 (3)	C15—H15	0.9500
C4—H4A	0.9800	C16—C17	1.376 (3)
C4—H4B	0.9800	C16—H16	0.9500
C4—H4C	0.9800	C17—C18	1.411 (2)
C5—C6	1.491 (2)	C17—H17	0.9500
C5—H5A	0.9800

O3—Zn—O1	115.05 (6)	H5A—C5—H5C	109.5
O3—Zn—N1	100.66 (6)	H5B—C5—H5C	109.5
O1—Zn—N1	133.70 (6)	N1—C6—C7	109.92 (15)
O3—Zn—N3	130.20 (6)	N1—C6—C5	121.23 (16)
O1—Zn—N3	99.32 (5)	C7—C6—C5	128.84 (16)
N1—Zn—N3	76.50 (6)	C8—C7—C6	107.15 (16)
O3—Zn—O2	100.51 (6)	C8—C7—H7	126.4
O1—Zn—O2	59.65 (5)	C6—C7—H7	126.4
N1—Zn—O2	86.61 (6)	C7—C8—N2	106.19 (15)
N3—Zn—O2	128.42 (6)	C7—C8—C9	126.73 (16)
C1—O1—Zn	96.11 (11)	N2—C8—C9	127.07 (15)
C1—O2—Zn	83.96 (12)	C8—C9—H9A	109.5
C3—O3—Zn	113.89 (12)	C8—C9—H9B	109.5
C6—N1—N2	106.53 (14)	H9A—C9—H9B	109.5
C6—N1—Zn	137.00 (12)	C8—C9—H9C	109.5
N2—N1—Zn	115.34 (10)	H9A—C9—H9C	109.5
N1—N2—C8	110.21 (13)	H9B—C9—H9C	109.5
N1—N2—C10	116.43 (14)	N3—C10—N2	115.77 (14)
C8—N2—C10	133.36 (14)	N3—C10—C11	123.55 (16)
C10—N3—C18	118.69 (14)	N2—C10—C11	120.68 (15)
C10—N3—Zn	114.76 (11)	C12—C11—C10	118.35 (16)
C18—N3—Zn	126.25 (11)	C12—C11—H11	120.8
O2—C1—O1	120.25 (17)	C10—C11—H11	120.8
O2—C1—C2	120.74 (17)	C11—C12—C13	120.42 (16)
O1—C1—C2	119.00 (17)	C11—C12—H12	119.8
C1—C2—H2A	109.5	C13—C12—H12	119.8
C1—C2—H2B	109.5	C12—C13—C18	117.95 (16)
H2A—C2—H2B	109.5	C12—C13—C14	122.76 (16)
C1—C2—H2C	109.5	C18—C13—C14	119.28 (16)
H2A—C2—H2C	109.5	C15—C14—C13	120.20 (16)
H2B—C2—H2C	109.5	C15—C14—H14	119.9
O4—C3—O3	123.91 (18)	C13—C14—H14	119.9
O4—C3—C4	120.51 (18)	C14—C15—C16	120.16 (17)
O3—C3—C4	115.58 (16)	C14—C15—H15	119.9
C3—C4—H4A	109.5	C16—C15—H15	119.9
C3—C4—H4B	109.5	C17—C16—C15	121.15 (17)
H4A—C4—H4B	109.5	C17—C16—H16	119.4
C3—C4—H4C	109.5	C15—C16—H16	119.4
H4A—C4—H4C	109.5	C16—C17—C18	119.54 (16)
H4B—C4—H4C	109.5	C16—C17—H17	120.2
C6—C5—H5A	109.5	C18—C17—H17	120.2
C6—C5—H5B	109.5	N3—C18—C17	119.36 (15)
H5A—C5—H5B	109.5	N3—C18—C13	121.01 (16)
C6—C5—H5C	109.5	C17—C18—C13	119.63 (16)

O3—Zn—O1—C1	86.61 (12)	Zn—N1—C6—C7	−165.93 (13)
N1—Zn—O1—C1	−50.21 (13)	N2—N1—C6—C5	−178.46 (15)
N3—Zn—O1—C1	−130.39 (11)	Zn—N1—C6—C5	15.0 (3)
O2—Zn—O1—C1	−1.07 (10)	N1—C6—C7—C8	−0.2 (2)
O3—Zn—O2—C1	−111.88 (12)	C5—C6—C7—C8	178.77 (18)
O1—Zn—O2—C1	1.10 (10)	C6—C7—C8—N2	−0.27 (19)
N1—Zn—O2—C1	147.89 (12)	C6—C7—C8—C9	178.33 (17)
N3—Zn—O2—C1	78.10 (13)	N1—N2—C8—C7	0.66 (19)
O1—Zn—O3—C3	65.51 (14)	C10—N2—C8—C7	179.74 (17)
N1—Zn—O3—C3	−144.72 (13)	N1—N2—C8—C9	−177.92 (16)
N3—Zn—O3—C3	−63.46 (15)	C10—N2—C8—C9	1.2 (3)
O2—Zn—O3—C3	126.78 (13)	C18—N3—C10—N2	179.97 (14)
O3—Zn—N1—C6	−55.42 (18)	Zn—N3—C10—N2	5.87 (19)
O1—Zn—N1—C6	85.47 (19)	C18—N3—C10—C11	−0.4 (3)
N3—Zn—N1—C6	175.51 (19)	Zn—N3—C10—C11	−174.50 (13)
O2—Zn—N1—C6	44.64 (18)	N1—N2—C10—N3	2.6 (2)
O3—Zn—N1—N2	138.85 (11)	C8—N2—C10—N3	−176.44 (17)
O1—Zn—N1—N2	−80.26 (13)	N1—N2—C10—C11	−177.04 (15)
N3—Zn—N1—N2	9.79 (11)	C8—N2—C10—C11	3.9 (3)
O2—Zn—N1—N2	−121.08 (12)	N3—C10—C11—C12	1.6 (3)
C6—N1—N2—C8	−0.80 (18)	N2—C10—C11—C12	−178.81 (16)
Zn—N1—N2—C8	169.09 (11)	C10—C11—C12—C13	−1.1 (3)
C6—N1—N2—C10	179.95 (14)	C11—C12—C13—C18	−0.4 (3)
Zn—N1—N2—C10	−10.16 (18)	C11—C12—C13—C14	−179.51 (17)
O3—Zn—N3—C10	−101.18 (13)	C12—C13—C14—C15	177.08 (17)
O1—Zn—N3—C10	124.36 (12)	C18—C13—C14—C15	−2.0 (3)
N1—Zn—N3—C10	−8.53 (12)	C13—C14—C15—C16	1.1 (3)
O2—Zn—N3—C10	65.92 (14)	C14—C15—C16—C17	0.7 (3)
O3—Zn—N3—C18	85.24 (15)	C15—C16—C17—C18	−1.5 (3)
O1—Zn—N3—C18	−49.22 (14)	C10—N3—C18—C17	178.31 (15)
N1—Zn—N3—C18	177.89 (15)	Zn—N3—C18—C17	−8.3 (2)
O2—Zn—N3—C18	−107.66 (14)	C10—N3—C18—C13	−1.2 (2)
Zn—O2—C1—O1	−1.76 (17)	Zn—N3—C18—C13	172.15 (12)
Zn—O2—C1—C2	177.01 (16)	C16—C17—C18—N3	−179.02 (16)
Zn—O1—C1—O2	2.01 (19)	C16—C17—C18—C13	0.5 (3)
Zn—O1—C1—C2	−176.78 (14)	C12—C13—C18—N3	1.6 (2)
Zn—O3—C3—O4	5.5 (2)	C14—C13—C18—N3	−179.25 (15)
Zn—O3—C3—C4	−174.94 (12)	C12—C13—C18—C17	−177.93 (16)
N2—N1—C6—C7	0.63 (19)	C14—C13—C18—C17	1.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O3ⁱ	0.98	2.57	3.544 (2)	176
C5—H5A···O2ⁱⁱ	0.98	2.60	3.417 (3)	141
C7—H7···O2ⁱⁱ	0.95	2.56	3.235 (2)	128
C9—H9C···O4ⁱⁱⁱ	0.98	2.36	3.274 (2)	156
C12—H12···O1^iv	0.95	2.51	3.310 (2)	142

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

Experimental details

Crystal data
Chemical formula	[Zn(C₂H₃O₂)₂(C₁₄H₁₃N₃)]
M_r	406.73
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.6586 (4), 10.7334 (6), 11.5772 (4)
α, β, γ (°)	69.437 (4), 81.546 (3), 72.736 (4)
V (Å³)	849.93 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.617, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6205, 3498, 3322
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.03
No. of reflections	3498
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.45

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Zn—O1	2.0388 (14)	Zn—N1	2.0570 (15)
Zn—O2	2.3240 (15)	Zn—N3	2.1460 (14)
Zn—O3	1.9397 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O3ⁱ	0.98	2.57	3.544 (2)	176
C5—H5A···O2ⁱⁱ	0.98	2.60	3.417 (3)	141
C7—H7···O2ⁱⁱ	0.95	2.56	3.235 (2)	128
C9—H9C···O4ⁱⁱⁱ	0.98	2.36	3.274 (2)	156
C12—H12···O1^iv	0.95	2.51	3.310 (2)	142

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

Footnotes

‡Additional correspondence author, e-mail: david.young@ubd.edu.bn.

Acknowledgements

We gratefully acknowledge funding from the Brunei Research Council, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Bai, S.-Q., Young, D. J. & Hor, T. S. A. (2011). Chem. Asian J. 6, 292–304. Web of Science CrossRef CAS PubMed Google Scholar
Bai, S.-Q., Young, A. M., Hu, J. J., Young, D. J., Zhang, X., Zong, Y., Xu, J., Zuo, J.-L. & Hor, T. S. A. (2012). CrystEngComm, 14, 961–971. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chou, P.-T., Chi, Y., Chung, M.-W. & Lin, C.-C. (2011). Coord. Chem. Rev. 255, 2653–2665. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Najib, M. H. bin, Tan, A. L., Young, D. J., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, m571–m572. CSD CrossRef IUCr Journals Google Scholar
Savel'eva, Z. A., Popov, S. A., Klevtsova, R. F., Glinskaya, L. A., Uskov, E. M., Tkachev, A. V. & Larionov, S. V. (2009). Russ. Chem. Bull., Int. Ed. 58, 1837–1840. Google Scholar
Scott, F. L., Crowley, K. M. & Reilly, J. (1952). J. Am. Chem. Soc. 74, 3444–3445. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S. (2001). Coord. Chem. Rev. 215, 79–98. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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