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

The title compound, [Zn(C(8)H(4)O(4))(C(5)H(8)N(2))(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 tetra-hedral 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, mol-ecules are linked into a three-dimensional hydrogen-bonded network by inter-molecular N-H⋯O interactions involving the uncoordinated carboxyl-ate O atoms.

Related literature

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

Experimental

Crystal data

[Zn(C8H4O4)(C5H8N2)3]

M = 517.90

Monoclinic,

a = 11.548 (2) Å

b = 11.759 (2) Å

c = 18.719 (4) Å

β = 91.79 (3)°

V = 2540.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 293 K

0.30 × 0.25 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.742, T max = 0.812

13021 measured reflections

5719 independent reflections

3534 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.114

S = 1.12

5719 reflections

317 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 2826 Friedel pairs

Flack parameter: 0.049 (15)

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014755/ci2775sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014755/ci2775Isup2.hkl

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

[Zn(C8H4O4)(C5H8N2)3]	F(000) = 1080
Mr = 517.90	Dx = 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

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

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(Fo2) + (0.0189P)2 + 0.8316P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
5719 reflections	Δρmax = 0.51 e Å−3
317 parameters	Δρmin = −0.28 e Å−3
16 restraints	Absolute structure: Flack (1983), 2826 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.049 (15)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

Table 1

Selected bond lengths (Å)

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

Table 2

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) .