Tris(2-ethyl-1H-imidazole-κN3)(terephthalato-κO)zinc(II)

Xie, Q.-A.; Dong, G.-Y.; Yu, Y.-M.; Wang, Y.-G.

doi:10.1107/S1600536809014755

Tris(2-ethyl-1H-imidazole-κN³)(terephthalato-κO)zinc(II)

Q.-A. Xie, G.-Y. Dong, Y.-M. Yu and Y.-G. Wang

The title compound, [Zn(C₈H₄O₄)(C₅H₈N₂)₃], has a neutral monomeric structure in which one terephthalate dianion and three 2-ethyl-1H-imidazole ligands coordinate to the Zn^II ion in a distorted tetrahedral geometry. The methyl group of one of the ethyl groups is disordered over two positions with occupancies of 0.66 (2) and 0.34 (2). In the crystal structure, molecules are linked into a three-dimensional hydrogen-bonded network by intermolecular N—H

O interactions involving the uncoordinated carboxylate O atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809014755/ci2775sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809014755/ci2775Isup2.hkl Contains datablock I

CCDC reference: 731183

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
Disorder in main residue
R factor = 0.073
wR factor = 0.114
Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.65 Ratio

Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.82 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    --  C23     ..       5.11 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT234_ALERT_4_C Large Hirshfeld Difference C14    --  C17     ..       0.21 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               5719
           Count of symmetry unique reflns         2908
           Completeness (_total/calc)            196.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2811
           Fraction of Friedel pairs measured     0.967
           Are heavy atom types Z>Si present        yes
PLAT301_ALERT_3_G Note Main Residue  Disorder ....................       3.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         16
PLAT033_ALERT_4_G Flack x Parameter Value Deviates from Zero .....       0.05
PLAT062_ALERT_4_G Rescale T(min) & T(max) by .....................       0.99
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Metal complexes with imidazole can serve as biomimetic ligands for histidine residues which frequently participate in the co-ordination spheres of metalloenzyme active sites. In particular, carboxylate-histidine-zinc triad systems are regularly observed, and play important roles in the catalytic processes of more than thirty zinc enzymes (Chen et al., 1994). However, crystal structure reports of such model zinc complexes containing neutral imidazole ligands are rather rare, and so far only a few examples have been presented (Kimura et al., 1991; Chen et al., 1994). Here, we report the synthesis and crystal structure of the title complex.

The title compound is a monomeric zinc(II) complex (Fig. 1). The Zn^II center is four coordinated by three monodentate 2-ethyl-1H-imidazole ligands and by a monodentate terephthalate group, forming a distorted tetrahedral N3,O geometry. The Zn—N bond lengths are in the range 2.014 (6)–2.047 (7) Å and the Zn—O distance is 1.943 (6) Å (Table 1). The most distorted bond angle is O1—Zn1—N1 at 100.5 (3)°.

The N—H···O hydrogen bonds (Table 2) formed between three uncoordinated 2-ethyl-H-imidazole N atoms and two uncoordinated carboxylate O atoms, resulted in a three-dimensional hydrogen-bonded network.

Related literature top

For the crystal structures of related Zn^II complexes, see: Chen et al. (1994); Kimura et al. (1991); Yang et al. (2002).

Experimental top

The title compound was synthesized by a solvothermal method from Zn(NO₃)₂.6H₂O (29.8 mg, 0.1 mmol), terephthalic acid (77.6 mg,0.4 mmol), 2-ethylimidazole (38.4 mg, 0.4 mmol) and water-ethanol mixed slovent (3 ml). The starting mixture was homogenized and transferred to a sealed Teflon-lined solvothermal bomb (bomb volume: 25 ml) and heated at 433 K for 3 d under autogenous pressure. After cooling in a water bath, colourless crystals were obtained, which were washed and rinsed with distilled water and absolute ethyl alcohol (yield: 51.8% on the basis of Zn(NO₃)₂.6H₂O). Analysis calculated (%) for C₂₃H₂₈N₆O₄Zn: C 53.34, H 5.45, N 16.23%; found: C 53.18, H 5.43, N 16.13.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids. For clarity, H atoms have been omitted. Only the major disorder component is shown.

Tris(2-ethyl-1H-imidazole-κN³)(terephthalato-κO)zinc(II) top

Crystal data top

[Zn(C₈H₄O₄)(C₅H₈N₂)₃]	F(000) = 1080
M_r = 517.90	D_x = 1.354 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1240 reflections
a = 11.548 (2) Å	θ = 4.5–25.0°
b = 11.759 (2) Å	µ = 1.01 mm⁻¹
c = 18.719 (4) Å	T = 293 K
β = 91.79 (3)°	Block, white
V = 2540.7 (8) Å³	0.30 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	5719 independent reflections
Radiation source: fine-focus sealed tube	3534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.742, T_max = 0.812	k = −15→15
13021 measured reflections	l = −24→24

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)] = 0.073	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0189P)² + 0.8316P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
5719 reflections	Δρ_max = 0.51 e Å⁻³
317 parameters	Δρ_min = −0.28 e Å⁻³
16 restraints	Absolute structure: Flack (1983), 2826 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.049 (15)

Crystal data top

[Zn(C₈H₄O₄)(C₅H₈N₂)₃]	V = 2540.7 (8) Å³
M_r = 517.90	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 11.548 (2) Å	µ = 1.01 mm⁻¹
b = 11.759 (2) Å	T = 293 K
c = 18.719 (4) Å	0.30 × 0.25 × 0.22 mm
β = 91.79 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5719 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3534 reflections with I > 2σ(I)
T_min = 0.742, T_max = 0.812	R_int = 0.086
13021 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	H-atom parameters constrained
wR(F²) = 0.114	Δρ_max = 0.51 e Å⁻³
S = 1.12	Δρ_min = −0.28 e Å⁻³
5719 reflections	Absolute structure: Flack (1983), 2826 Friedel pairs
317 parameters	Absolute structure parameter: 0.049 (15)
16 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	Occ. (<1)
Zn1	0.31207 (5)	0.87464 (5)	1.00368 (4)	0.04221 (18)
O1	0.3327 (4)	1.0107 (4)	0.9463 (2)	0.0616 (12)
O2	0.1668 (4)	0.9779 (4)	0.8862 (3)	0.0651 (13)
O3	0.4207 (4)	1.5052 (4)	0.7476 (2)	0.0570 (12)
O4	0.3054 (4)	1.4345 (4)	0.6625 (2)	0.0628 (12)
N1	0.4459 (4)	0.8920 (4)	1.0769 (2)	0.0459 (13)
N2	0.6080 (5)	0.9487 (4)	1.1293 (3)	0.0647 (15)
H2	0.6768	0.9759	1.1355	0.078*
N3	0.1653 (4)	0.8651 (4)	1.0592 (2)	0.0421 (11)
N4	0.0232 (5)	0.8949 (5)	1.1303 (3)	0.0639 (15)
H4	−0.0184	0.9259	1.1622	0.077*
N5	0.3423 (4)	0.7220 (4)	0.9580 (2)	0.0436 (12)
N6	0.4022 (5)	0.5903 (4)	0.8863 (3)	0.0529 (14)
H6	0.4181	0.5548	0.8477	0.063*
C1	0.2545 (6)	1.0340 (5)	0.8977 (3)	0.0476 (15)
C2	0.2797 (5)	1.1396 (5)	0.8544 (3)	0.0392 (14)
C3	0.3797 (5)	1.2032 (5)	0.8667 (3)	0.0443 (15)
H3	0.4319	1.1816	0.9030	0.053*
C4	0.4029 (5)	1.2980 (5)	0.8259 (3)	0.0420 (14)
H4A	0.4702	1.3396	0.8351	0.050*
C5	0.3255 (5)	1.3317 (4)	0.7707 (3)	0.0341 (13)
C6	0.2258 (5)	1.2678 (5)	0.7579 (3)	0.0407 (15)
H6A	0.1738	1.2885	0.7213	0.049*
C7	0.2034 (5)	1.1723 (5)	0.8001 (3)	0.0447 (15)
H7	0.1362	1.1304	0.7913	0.054*
C8	0.3515 (5)	1.4310 (5)	0.7235 (3)	0.0427 (15)
C9	0.5509 (6)	0.9366 (5)	1.0669 (3)	0.0470 (15)
C10	0.5378 (8)	0.9101 (7)	1.1818 (4)	0.088 (3)
H10	0.5553	0.9084	1.2306	0.106*
C11	0.4387 (6)	0.8751 (6)	1.1490 (4)	0.074 (2)
H11	0.3754	0.8444	1.1717	0.088*
C12	0.6028 (5)	0.9657 (5)	0.9961 (3)	0.0558 (18)
H12A	0.6636	1.0218	1.0038	0.067*
H12B	0.5436	0.9993	0.9649	0.067*
C13	0.6528 (8)	0.8621 (7)	0.9599 (4)	0.101 (3)
H13A	0.6846	0.8842	0.9152	0.152*
H13B	0.5927	0.8070	0.9515	0.152*
H13C	0.7128	0.8297	0.9902	0.152*
C14	0.1249 (5)	0.9330 (5)	1.1079 (3)	0.0498 (16)
C15	−0.0025 (6)	0.7984 (6)	1.0934 (4)	0.066 (2)
H15	−0.0683	0.7535	1.0974	0.080*
C16	0.0867 (5)	0.7808 (5)	1.0497 (4)	0.0542 (17)
H16	0.0930	0.7203	1.0181	0.065*
C17	0.1830 (8)	1.0329 (7)	1.1407 (5)	0.110 (3)
H17A	0.1455	1.0515	1.1848	0.132*	0.661 (18)
H17B	0.2629	1.0134	1.1526	0.132*	0.661 (18)
H17C	0.2519	1.0460	1.1144	0.132*	0.339 (18)
H17D	0.2080	1.0100	1.1879	0.132*	0.339 (18)
C18A	0.1810 (13)	1.1331 (11)	1.0944 (8)	0.115 (6)	0.661 (18)
H18A	0.2203	1.1948	1.1184	0.172*	0.661 (18)
H18B	0.1022	1.1544	1.0835	0.172*	0.661 (18)
H18C	0.2192	1.1158	1.0509	0.172*	0.661 (18)
C18B	0.1283 (18)	1.1454 (12)	1.1528 (14)	0.079 (9)	0.339 (18)
H18D	0.1837	1.1955	1.1756	0.119*	0.339 (18)
H18E	0.0631	1.1362	1.1828	0.119*	0.339 (18)
H18F	0.1029	1.1772	1.1077	0.119*	0.339 (18)
C19	0.3515 (5)	0.6916 (5)	0.8896 (3)	0.0445 (15)
C20	0.4250 (6)	0.5515 (5)	0.9545 (3)	0.0547 (17)
H20	0.4601	0.4832	0.9678	0.066*
C21	0.3857 (5)	0.6335 (5)	0.9983 (3)	0.0482 (15)
H21	0.3879	0.6304	1.0480	0.058*
C22	0.3089 (7)	0.7583 (6)	0.8248 (4)	0.070 (2)
H22A	0.2804	0.7060	0.7883	0.085*
H22B	0.2450	0.8067	0.8381	0.085*
C23	0.4025 (8)	0.8302 (8)	0.7949 (5)	0.124 (4)
H23A	0.3723	0.8713	0.7541	0.187*
H23B	0.4653	0.7825	0.7808	0.187*
H23C	0.4301	0.8831	0.8306	0.187*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0425 (3)	0.0409 (3)	0.0436 (4)	0.0011 (5)	0.0069 (2)	0.0037 (4)
O1	0.059 (3)	0.059 (3)	0.067 (3)	0.006 (2)	0.004 (2)	0.027 (2)
O2	0.052 (3)	0.052 (3)	0.092 (4)	−0.005 (2)	0.005 (3)	0.017 (3)
O3	0.081 (3)	0.052 (3)	0.039 (3)	−0.003 (3)	0.015 (2)	0.010 (2)
O4	0.066 (3)	0.078 (3)	0.044 (3)	0.007 (3)	−0.005 (2)	0.020 (3)
N1	0.051 (3)	0.050 (3)	0.037 (3)	−0.008 (3)	0.003 (2)	0.003 (2)
N2	0.060 (4)	0.071 (4)	0.062 (4)	−0.004 (3)	−0.012 (3)	−0.011 (3)
N3	0.045 (3)	0.042 (3)	0.040 (3)	0.000 (3)	0.009 (2)	−0.005 (3)
N4	0.063 (4)	0.065 (4)	0.064 (4)	0.009 (3)	0.021 (3)	−0.012 (3)
N5	0.047 (3)	0.050 (3)	0.035 (3)	0.003 (2)	0.005 (2)	0.001 (2)
N6	0.071 (4)	0.043 (3)	0.045 (3)	0.007 (3)	0.015 (3)	0.000 (3)
C1	0.050 (4)	0.042 (4)	0.052 (4)	0.013 (3)	0.011 (3)	0.002 (3)
C2	0.044 (3)	0.035 (3)	0.038 (3)	0.005 (3)	0.004 (3)	0.002 (3)
C3	0.053 (4)	0.040 (4)	0.039 (4)	0.007 (3)	−0.007 (3)	0.007 (3)
C4	0.041 (4)	0.041 (4)	0.043 (4)	0.001 (3)	−0.002 (3)	0.001 (3)
C5	0.038 (3)	0.039 (3)	0.026 (3)	0.010 (3)	0.008 (2)	0.002 (3)
C6	0.037 (4)	0.051 (4)	0.033 (3)	0.009 (3)	−0.006 (3)	−0.002 (3)
C7	0.041 (4)	0.050 (4)	0.043 (4)	0.003 (3)	0.002 (3)	−0.003 (3)
C8	0.041 (4)	0.046 (4)	0.042 (4)	0.013 (3)	0.013 (3)	0.007 (3)
C9	0.058 (4)	0.029 (3)	0.053 (4)	0.003 (3)	0.000 (3)	−0.006 (3)
C10	0.095 (7)	0.127 (8)	0.042 (5)	0.006 (6)	−0.003 (5)	−0.008 (5)
C11	0.071 (5)	0.096 (6)	0.053 (5)	−0.004 (5)	0.002 (4)	0.013 (4)
C12	0.042 (4)	0.062 (5)	0.064 (5)	−0.010 (3)	0.005 (3)	0.004 (4)
C13	0.110 (7)	0.102 (7)	0.095 (7)	−0.010 (6)	0.047 (5)	−0.036 (6)
C14	0.049 (4)	0.049 (4)	0.052 (4)	−0.005 (3)	0.004 (3)	−0.010 (3)
C15	0.049 (4)	0.060 (5)	0.091 (6)	−0.016 (4)	0.011 (4)	−0.008 (4)
C16	0.044 (4)	0.046 (4)	0.073 (5)	−0.007 (3)	0.008 (3)	−0.019 (3)
C17	0.105 (8)	0.092 (7)	0.134 (8)	−0.003 (6)	0.015 (6)	−0.032 (6)
C18A	0.116 (9)	0.103 (9)	0.125 (10)	−0.004 (7)	0.002 (7)	0.009 (7)
C18B	0.077 (11)	0.069 (12)	0.092 (12)	−0.004 (8)	0.006 (8)	−0.009 (8)
C19	0.051 (4)	0.042 (4)	0.041 (4)	0.000 (3)	0.009 (3)	0.002 (3)
C20	0.066 (4)	0.045 (4)	0.053 (4)	0.009 (3)	0.007 (3)	0.005 (3)
C21	0.052 (4)	0.055 (4)	0.038 (3)	−0.001 (3)	−0.001 (3)	0.002 (3)
C22	0.101 (6)	0.056 (5)	0.054 (5)	0.020 (4)	0.012 (4)	0.006 (4)
C23	0.119 (8)	0.167 (10)	0.089 (7)	0.057 (7)	0.028 (6)	0.054 (7)

Geometric parameters (Å, º) top

Zn1—O1	1.947 (4)	C10—C11	1.346 (10)
Zn1—N3	2.018 (4)	C10—H10	0.93
Zn1—N5	2.023 (5)	C11—H11	0.93
Zn1—N1	2.044 (5)	C12—C13	1.516 (9)
O1—C1	1.291 (7)	C12—H12A	0.97
O2—C1	1.223 (7)	C12—H12B	0.97
O3—C8	1.257 (7)	C13—H13A	0.96
O4—C8	1.245 (7)	C13—H13B	0.96
N1—C9	1.339 (7)	C13—H13C	0.96
N1—C11	1.370 (8)	C14—C17	1.477 (9)
N2—C9	1.331 (8)	C15—C16	1.351 (8)
N2—C10	1.371 (9)	C15—H15	0.93
N2—H2	0.86	C16—H16	0.93
N3—C14	1.309 (7)	C17—C18A	1.462 (8)
N3—C16	1.352 (7)	C17—C18B	1.486 (9)
N4—C14	1.336 (7)	C17—H17A	0.97
N4—C15	1.356 (8)	C17—H17B	0.97
N4—H4	0.86	C17—H17C	0.96
N5—C19	1.337 (7)	C17—H17D	0.96
N5—C21	1.371 (7)	C18A—H18A	0.96
N6—C19	1.330 (7)	C18A—H18B	0.96
N6—C20	1.373 (7)	C18A—H18C	0.96
N6—H6	0.86	C18B—H18D	0.96
C1—C2	1.516 (8)	C18B—H18E	0.96
C2—C7	1.379 (7)	C18B—H18F	0.96
C2—C3	1.389 (8)	C19—C22	1.513 (9)
C3—C4	1.382 (7)	C20—C21	1.354 (7)
C3—H3	0.93	C20—H20	0.93
C4—C5	1.402 (7)	C21—H21	0.93
C4—H4A	0.93	C22—C23	1.495 (11)
C5—C6	1.389 (7)	C22—H22A	0.97
C5—C8	1.501 (7)	C22—H22B	0.97
C6—C7	1.401 (8)	C23—H23A	0.96
C6—H6A	0.93	C23—H23B	0.96
C7—H7	0.93	C23—H23C	0.96
C9—C12	1.512 (8)

O1—Zn1—N3	116.67 (18)	C13—C12—H12B	109.2
O1—Zn1—N5	118.06 (18)	H12A—C12—H12B	107.9
N3—Zn1—N5	109.09 (19)	C12—C13—H13A	109.5
O1—Zn1—N1	100.7 (2)	C12—C13—H13B	109.5
N3—Zn1—N1	106.87 (18)	H13A—C13—H13B	109.5
N5—Zn1—N1	103.6 (2)	C12—C13—H13C	109.5
C1—O1—Zn1	117.9 (4)	H13A—C13—H13C	109.5
C9—N1—C11	106.1 (5)	H13B—C13—H13C	109.5
C9—N1—Zn1	127.9 (4)	N3—C14—N4	110.5 (5)
C11—N1—Zn1	125.3 (4)	N3—C14—C17	127.4 (6)
C9—N2—C10	107.8 (6)	N4—C14—C17	121.9 (6)
C9—N2—H2	126.1	C16—C15—N4	106.1 (6)
C10—N2—H2	126.1	C16—C15—H15	127.0
C14—N3—C16	106.6 (5)	N4—C15—H15	127.0
C14—N3—Zn1	130.4 (4)	C15—C16—N3	109.3 (6)
C16—N3—Zn1	123.0 (4)	C15—C16—H16	125.4
C14—N4—C15	107.6 (5)	N3—C16—H16	125.4
C14—N4—H4	126.2	C18A—C17—C14	113.4 (9)
C15—N4—H4	126.2	C14—C17—C18B	125.6 (11)
C19—N5—C21	106.6 (5)	C18A—C17—H17A	108.9
C19—N5—Zn1	131.5 (4)	C14—C17—H17A	108.9
C21—N5—Zn1	120.4 (4)	C18A—C17—H17B	108.9
C19—N6—C20	109.1 (5)	C14—C17—H17B	108.9
C19—N6—H6	125.4	H17A—C17—H17B	107.7
C20—N6—H6	125.4	C14—C17—H17C	106.7
O2—C1—O1	124.6 (6)	C18B—C17—H17C	107.3
O2—C1—C2	121.3 (6)	C14—C17—H17D	106.2
O1—C1—C2	114.1 (6)	C18B—C17—H17D	103.1
C7—C2—C3	118.7 (5)	H17C—C17—H17D	106.7
C7—C2—C1	119.6 (5)	C17—C18A—H18A	109.5
C3—C2—C1	121.7 (5)	C17—C18A—H18B	109.5
C4—C3—C2	121.2 (5)	H18A—C18A—H18B	109.5
C4—C3—H3	119.4	C17—C18A—H18C	109.5
C2—C3—H3	119.4	H18A—C18A—H18C	109.5
C3—C4—C5	120.3 (5)	H18B—C18A—H18C	109.5
C3—C4—H4A	119.8	C17—C18B—H18D	109.5
C5—C4—H4A	119.8	C17—C18B—H18E	109.5
C6—C5—C4	118.7 (5)	H18D—C18B—H18E	109.5
C6—C5—C8	120.0 (5)	C17—C18B—H18F	109.5
C4—C5—C8	121.3 (5)	H18D—C18B—H18F	109.5
C5—C6—C7	120.2 (5)	H18E—C18B—H18F	109.5
C5—C6—H6A	119.9	N6—C19—N5	109.4 (5)
C7—C6—H6A	119.9	N6—C19—C22	124.1 (6)
C2—C7—C6	120.9 (6)	N5—C19—C22	126.5 (6)
C2—C7—H7	119.5	C21—C20—N6	105.6 (5)
C6—C7—H7	119.5	C21—C20—H20	127.2
O4—C8—O3	123.7 (6)	N6—C20—H20	127.2
O4—C8—C5	118.5 (6)	C20—C21—N5	109.3 (5)
O3—C8—C5	117.7 (5)	C20—C21—H21	125.3
N2—C9—N1	110.3 (6)	N5—C21—H21	125.3
N2—C9—C12	123.0 (6)	C23—C22—C19	111.9 (7)
N1—C9—C12	126.7 (6)	C23—C22—H22A	109.2
C11—C10—N2	106.8 (7)	C19—C22—H22A	109.2
C11—C10—H10	126.6	C23—C22—H22B	109.2
N2—C10—H10	126.6	C19—C22—H22B	109.2
C10—C11—N1	109.1 (7)	H22A—C22—H22B	107.9
C10—C11—H11	125.5	C22—C23—H23A	109.5
N1—C11—H11	125.5	C22—C23—H23B	109.5
C9—C12—C13	112.1 (5)	H23A—C23—H23B	109.5
C9—C12—H12A	109.2	C22—C23—H23C	109.5
C13—C12—H12A	109.2	H23A—C23—H23C	109.5
C9—C12—H12B	109.2	H23B—C23—H23C	109.5

N3—Zn1—O1—C1	−58.2 (5)	C4—C5—C8—O3	−23.6 (8)
N5—Zn1—O1—C1	74.8 (4)	C10—N2—C9—N1	0.3 (7)
N1—Zn1—O1—C1	−173.4 (4)	C10—N2—C9—C12	−177.4 (6)
O1—Zn1—N1—C9	−34.4 (5)	C11—N1—C9—N2	−0.5 (7)
N3—Zn1—N1—C9	−156.7 (5)	Zn1—N1—C9—N2	170.7 (4)
N5—Zn1—N1—C9	88.1 (5)	C11—N1—C9—C12	177.1 (6)
O1—Zn1—N1—C11	135.2 (5)	Zn1—N1—C9—C12	−11.7 (9)
N3—Zn1—N1—C11	12.9 (6)	C9—N2—C10—C11	0.1 (8)
N5—Zn1—N1—C11	−102.3 (6)	N2—C10—C11—N1	−0.3 (9)
O1—Zn1—N3—C14	−58.6 (6)	C9—N1—C11—C10	0.5 (8)
N5—Zn1—N3—C14	164.5 (5)	Zn1—N1—C11—C10	−171.0 (5)
N1—Zn1—N3—C14	53.0 (6)	N2—C9—C12—C13	96.4 (7)
O1—Zn1—N3—C16	120.4 (5)	N1—C9—C12—C13	−80.8 (8)
N5—Zn1—N3—C16	−16.6 (5)	C16—N3—C14—N4	0.2 (7)
N1—Zn1—N3—C16	−128.0 (5)	Zn1—N3—C14—N4	179.3 (4)
O1—Zn1—N5—C19	−16.2 (6)	C16—N3—C14—C17	175.1 (7)
N3—Zn1—N5—C19	120.0 (5)	Zn1—N3—C14—C17	−5.7 (10)
N1—Zn1—N5—C19	−126.4 (5)	C15—N4—C14—N3	−0.4 (7)
O1—Zn1—N5—C21	147.3 (4)	C15—N4—C14—C17	−175.7 (7)
N3—Zn1—N5—C21	−76.4 (4)	C14—N4—C15—C16	0.5 (8)
N1—Zn1—N5—C21	37.2 (5)	N4—C15—C16—N3	−0.4 (8)
Zn1—O1—C1—O2	1.8 (8)	C14—N3—C16—C15	0.1 (8)
Zn1—O1—C1—C2	−178.4 (3)	Zn1—N3—C16—C15	−179.1 (5)
O2—C1—C2—C7	−1.2 (8)	N3—C14—C17—C18A	77.0 (12)
O1—C1—C2—C7	179.0 (5)	N4—C14—C17—C18A	−108.6 (11)
O2—C1—C2—C3	−179.4 (5)	N3—C14—C17—C18B	135.1 (15)
O1—C1—C2—C3	0.8 (8)	N4—C14—C17—C18B	−50.5 (17)
C7—C2—C3—C4	0.4 (8)	C20—N6—C19—N5	1.3 (7)
C1—C2—C3—C4	178.6 (5)	C20—N6—C19—C22	−177.2 (6)
C2—C3—C4—C5	−0.3 (8)	C21—N5—C19—N6	−2.1 (6)
C3—C4—C5—C6	−0.2 (8)	Zn1—N5—C19—N6	163.1 (4)
C3—C4—C5—C8	−177.1 (5)	C21—N5—C19—C22	176.4 (6)
C4—C5—C6—C7	0.5 (8)	Zn1—N5—C19—C22	−18.4 (9)
C8—C5—C6—C7	177.5 (5)	C19—N6—C20—C21	0.1 (7)
C3—C2—C7—C6	0.0 (8)	N6—C20—C21—N5	−1.4 (7)
C1—C2—C7—C6	−178.3 (5)	C19—N5—C21—C20	2.2 (7)
C5—C6—C7—C2	−0.4 (8)	Zn1—N5—C21—C20	−165.0 (4)
C6—C5—C8—O4	−21.7 (8)	N6—C19—C22—C23	−86.7 (9)
C4—C5—C8—O4	155.2 (5)	N5—C19—C22—C23	95.0 (8)
C6—C5—C8—O3	159.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.88	2.717 (7)	165
N4—H4···O3ⁱⁱ	0.86	1.94	2.787 (7)	167
N6—H6···O3ⁱⁱⁱ	0.86	1.96	2.797 (7)	163

Symmetry codes: (i) x+1/2, −y+5/2, z+1/2; (ii) x−1/2, −y+5/2, z+1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₄)(C₅H₈N₂)₃]
M_r	517.90
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	11.548 (2), 11.759 (2), 18.719 (4)
β (°)	91.79 (3)
V (Å³)	2540.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.30 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.742, 0.812
No. of measured, independent and observed [I > 2σ(I)] reflections	13021, 5719, 3534
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.114, 1.12
No. of reflections	5719
No. of parameters	317
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.28
Absolute structure	Flack (1983), 2826 Friedel pairs
Absolute structure parameter	0.049 (15)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	1.947 (4)	Zn1—N5	2.023 (5)
Zn1—N3	2.018 (4)	Zn1—N1	2.044 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.88	2.717 (7)	165
N4—H4···O3ⁱⁱ	0.86	1.94	2.787 (7)	167
N6—H6···O3ⁱⁱⁱ	0.86	1.96	2.797 (7)	163

Symmetry codes: (i) x+1/2, −y+5/2, z+1/2; (ii) x−1/2, −y+5/2, z+1/2; (iii) x, y−1, z.

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