(Acetato-κO)(2,5,5,7,9,12,12,14-octa-methyl-1,4,8,11-tetra-aza-cyclo-tetra-decane-κN,N',N'',N''')zinc perchlorate.

The Zn(II) atom in the cation of the title salt, [Zn(C(2)H(3)O(2))(C(18)H(40)N(4))]ClO(4), is five-coordinated by the four N atoms of the macrocycle and the O atom of the monodentate acetate ligand. The N(4)O donor set is based on a trigonal bipyramid with two N atoms occupying axial positions [N-Zn-N = 170.89 (16)°]. The perchlorate anions are associated with the cations via N-H⋯O hydrogen bonds; intra-molecular N-H⋯O(acetate) inter-actions are also observed. The neutral aggregates are connected into an helical chain along the b axis via N-H⋯O(acetate) hydrogen bonds. The perchlorate anion was found to be disordered about a pseudo-threefold axis: the major component of the disorder had a site occupancy factor of 0.692 (11).

Related literature

For background to the synthesis, characterization, kinetic studies and biological activity of 14-membered methyl-substituted tetra­aza­macrocyclic ligands, their N-substituted derivatives and their n class="Chemical">metal complexes, see: Bembi et al. (1990 ▶); Roy et al. (2007 ▶, 2011 ▶); Hazari et al. (2008 ▶). For additional geometric analysis, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Zn(C2H3O2)(C18H40N4)]ClO4

M = 536.40

Orthorhombic,

a = 17.822 (6) Å

b = 12.995 (6) Å

c = 22.381 (7) Å

V = 5183 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.09 mm−1

T = 153 K

0.30 × 0.11 × 0.04 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.602, T max = 1.000

23785 measured reflections

4534 independent reflections

4080 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.183

S = 1.29

4534 reflections

320 parameters

22 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045582/hb6470sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045582/hb6470Isup2.hkl

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

[Zn(C2H3O2)(C18H40N4)]ClO4	F(000) = 2288
Mr = 536.40	Dx = 1.375 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7295 reflections
a = 17.822 (6) Å	θ = 2.9–30.3°
b = 12.995 (6) Å	µ = 1.09 mm−1
c = 22.381 (7) Å	T = 153 K
V = 5183 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.11 × 0.04 mm

Rigaku AFC12K/SATURN724 diffractometer	4534 independent reflections
Radiation source: fine-focus sealed tube	4080 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→19
Tmin = 0.602, Tmax = 1.000	k = −12→15
23785 measured reflections	l = −23→26

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	w = 1/[σ2(Fo2) + (0.0546P)2 + 10.5654P] where P = (Fo2 + 2Fc2)/3
4534 reflections	(Δ/σ)max = 0.002
320 parameters	Δρmax = 0.63 e Å−3
22 restraints	Δρmin = −0.48 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
Zn	1.01476 (3)	0.24442 (4)	0.65431 (3)	0.0345 (2)
O1	1.0503 (2)	0.2678 (3)	0.73667 (16)	0.0433 (9)
O2	1.0583 (2)	0.1015 (3)	0.76154 (16)	0.0491 (10)
N1	1.0563 (2)	0.3315 (3)	0.58108 (19)	0.0335 (9)
H1N	1.032 (3)	0.304 (4)	0.5507 (16)	0.040*
N2	0.9363 (2)	0.3757 (3)	0.6641 (2)	0.0392 (10)
H2N	0.952 (3)	0.419 (3)	0.6913 (19)	0.047*
N3	0.9287 (2)	0.1464 (3)	0.62552 (19)	0.0349 (10)
H3N	0.923 (3)	0.166 (4)	0.5881 (9)	0.042*
N4	1.0846 (2)	0.1156 (3)	0.63040 (19)	0.0351 (10)
H4N	1.093 (3)	0.086 (4)	0.6652 (12)	0.042*
C1	1.0292 (3)	0.4397 (4)	0.5913 (2)	0.0379 (12)
H1	1.0340	0.4792	0.5531	0.046*
C2	1.0757 (3)	0.4927 (4)	0.6390 (3)	0.0444 (14)
H2A	1.0825	0.4461	0.6730	0.067*
H2B	1.0498	0.5552	0.6524	0.067*
H2C	1.1248	0.5111	0.6225	0.067*
C3	0.9465 (3)	0.4332 (4)	0.6080 (2)	0.0404 (13)
H3A	0.9259	0.5035	0.6126	0.048*
H3B	0.9185	0.3985	0.5755	0.048*
C4	0.8573 (3)	0.3561 (5)	0.6842 (3)	0.0467 (14)
C5	0.8056 (4)	0.4482 (5)	0.6709 (4)	0.0645 (19)
H5A	0.8290	0.5115	0.6856	0.097*
H5B	0.7572	0.4380	0.6909	0.097*
H5C	0.7976	0.4535	0.6277	0.097*
C6	0.8606 (4)	0.3452 (5)	0.7522 (3)	0.0587 (17)
H6A	0.8995	0.2952	0.7629	0.088*
H6B	0.8119	0.3214	0.7670	0.088*
H6C	0.8725	0.4121	0.7701	0.088*
C7	0.8231 (3)	0.2632 (4)	0.6516 (3)	0.0477 (15)
H7A	0.8237	0.2799	0.6084	0.057*
H7B	0.7697	0.2597	0.6636	0.057*
C8	0.8554 (3)	0.1523 (4)	0.6580 (3)	0.0439 (13)
H8	0.8203	0.1065	0.6354	0.053*
C9	0.8603 (3)	0.1078 (5)	0.7196 (3)	0.0535 (16)
H9A	0.8657	0.0329	0.7169	0.080*
H9B	0.8146	0.1247	0.7418	0.080*
H9C	0.9039	0.1368	0.7403	0.080*
C10	0.9591 (3)	0.0393 (4)	0.6200 (2)	0.0369 (12)
H10	0.9632	0.0086	0.6608	0.044*
C11	0.9102 (3)	−0.0302 (4)	0.5816 (3)	0.0435 (13)
H11A	0.8634	−0.0454	0.6028	0.065*
H11B	0.9370	−0.0945	0.5734	0.065*
H11C	0.8987	0.0046	0.5438	0.065*
C12	1.0379 (3)	0.0472 (4)	0.5929 (2)	0.0372 (12)
H12A	1.0610	−0.0220	0.5907	0.045*
H12B	1.0347	0.0752	0.5518	0.045*
C13	1.1625 (3)	0.1373 (4)	0.6071 (2)	0.0397 (12)
C14	1.2063 (3)	0.1843 (5)	0.6585 (3)	0.0494 (15)
H14A	1.2567	0.2030	0.6448	0.074*
H14B	1.2101	0.1343	0.6911	0.074*
H14C	1.1802	0.2461	0.6728	0.074*
C15	1.2013 (3)	0.0373 (5)	0.5876 (3)	0.0500 (15)
H15A	1.2539	0.0515	0.5778	0.075*
H15B	1.1758	0.0094	0.5524	0.075*
H15C	1.1989	−0.0129	0.6202	0.075*
C16	1.1590 (3)	0.2100 (4)	0.5530 (2)	0.0359 (12)
H16A	1.1229	0.1803	0.5242	0.043*
H16B	1.2089	0.2089	0.5336	0.043*
C17	1.1374 (3)	0.3234 (4)	0.5624 (2)	0.0352 (12)
H17	1.1693	0.3523	0.5951	0.042*
C18	1.1531 (3)	0.3833 (4)	0.5052 (2)	0.0449 (13)
H18A	1.2058	0.3746	0.4940	0.067*
H18B	1.1426	0.4564	0.5118	0.067*
H18C	1.1209	0.3573	0.4731	0.067*
C19	1.0657 (3)	0.1956 (4)	0.7740 (2)	0.0390 (12)
C20	1.0900 (4)	0.2282 (5)	0.8341 (3)	0.0555 (16)
H20A	1.0463	0.2319	0.8606	0.083*
H20B	1.1137	0.2961	0.8316	0.083*
H20C	1.1260	0.1783	0.8500	0.083*
Cl	0.90070 (8)	0.24995 (10)	0.45914 (6)	0.0454 (4)	0.692 (11)
O3	0.8898 (3)	0.2216 (4)	0.39872 (16)	0.0672 (13)	0.692 (11)
O4	0.9752 (3)	0.2296 (10)	0.4786 (4)	0.102 (4)	0.692 (11)
O5	0.8516 (5)	0.1844 (6)	0.4969 (3)	0.081 (3)	0.692 (11)
O6	0.8776 (6)	0.3529 (4)	0.4698 (3)	0.074 (3)	0.692 (11)
Cl1	0.90070 (8)	0.24995 (10)	0.45914 (6)	0.0454 (4)	0.308 (11)
O13	0.8898 (3)	0.2216 (4)	0.39872 (16)	0.0672 (13)	0.308 (11)
O14	0.9755 (6)	0.2979 (15)	0.4630 (7)	0.102 (4)	0.308 (11)
O15	0.8985 (12)	0.1657 (9)	0.4985 (5)	0.081 (3)	0.308 (11)
O16	0.8483 (9)	0.3283 (11)	0.4765 (7)	0.074 (3)	0.308 (11)

	U11	U22	U33	U12	U13	U23
Zn	0.0378 (4)	0.0312 (4)	0.0344 (4)	−0.0006 (3)	0.0006 (2)	0.0000 (2)
O1	0.054 (2)	0.042 (2)	0.034 (2)	0.0042 (18)	−0.0023 (17)	−0.0004 (17)
O2	0.071 (3)	0.038 (2)	0.038 (2)	−0.006 (2)	−0.0047 (19)	0.0031 (18)
N1	0.036 (2)	0.029 (2)	0.035 (2)	0.0017 (19)	−0.0041 (18)	−0.0017 (18)
N2	0.039 (3)	0.036 (3)	0.042 (3)	0.003 (2)	0.001 (2)	−0.004 (2)
N3	0.036 (2)	0.032 (2)	0.037 (2)	0.0009 (18)	0.0018 (19)	−0.0004 (19)
N4	0.038 (2)	0.033 (2)	0.034 (2)	0.0042 (19)	−0.0036 (19)	0.0014 (19)
C1	0.053 (3)	0.025 (3)	0.036 (3)	0.004 (2)	0.004 (2)	0.000 (2)
C2	0.053 (4)	0.033 (3)	0.047 (3)	−0.008 (3)	0.012 (3)	−0.009 (2)
C3	0.044 (3)	0.037 (3)	0.041 (3)	0.008 (2)	−0.001 (2)	−0.005 (2)
C4	0.044 (3)	0.041 (3)	0.055 (4)	0.000 (3)	0.007 (3)	−0.008 (3)
C5	0.049 (4)	0.045 (4)	0.100 (5)	0.009 (3)	0.005 (4)	−0.014 (4)
C6	0.058 (4)	0.057 (4)	0.060 (4)	−0.013 (3)	0.024 (3)	−0.017 (3)
C7	0.034 (3)	0.050 (4)	0.059 (4)	0.000 (3)	0.004 (3)	−0.013 (3)
C8	0.044 (3)	0.034 (3)	0.053 (3)	−0.005 (2)	0.006 (3)	−0.009 (3)
C9	0.053 (4)	0.052 (4)	0.056 (4)	−0.008 (3)	0.014 (3)	−0.005 (3)
C10	0.044 (3)	0.028 (3)	0.038 (3)	0.001 (2)	−0.003 (2)	0.001 (2)
C11	0.051 (3)	0.032 (3)	0.047 (3)	−0.006 (3)	0.005 (3)	−0.003 (2)
C12	0.039 (3)	0.034 (3)	0.038 (3)	0.004 (2)	0.000 (2)	−0.005 (2)
C13	0.037 (3)	0.036 (3)	0.046 (3)	0.005 (2)	−0.003 (2)	−0.002 (2)
C14	0.046 (3)	0.054 (4)	0.048 (4)	−0.002 (3)	−0.006 (3)	0.004 (3)
C15	0.044 (3)	0.045 (3)	0.061 (4)	0.008 (3)	0.002 (3)	0.002 (3)
C16	0.034 (3)	0.035 (3)	0.039 (3)	0.001 (2)	0.000 (2)	−0.005 (2)
C17	0.038 (3)	0.035 (3)	0.032 (3)	−0.001 (2)	0.000 (2)	−0.004 (2)
C18	0.049 (3)	0.037 (3)	0.049 (3)	−0.003 (3)	0.005 (3)	0.002 (3)
C19	0.038 (3)	0.044 (3)	0.035 (3)	0.002 (2)	0.007 (2)	0.010 (2)
C20	0.076 (5)	0.046 (4)	0.045 (3)	−0.008 (3)	−0.006 (3)	0.001 (3)
Cl	0.0548 (9)	0.0363 (7)	0.0450 (8)	0.0057 (6)	−0.0117 (6)	−0.0036 (6)
O3	0.090 (4)	0.066 (3)	0.045 (3)	0.003 (3)	−0.022 (2)	−0.010 (2)
O4	0.060 (4)	0.161 (11)	0.085 (6)	0.047 (6)	−0.037 (4)	−0.066 (7)
O5	0.103 (8)	0.070 (5)	0.069 (4)	−0.023 (5)	−0.008 (5)	0.019 (3)
O6	0.122 (8)	0.025 (4)	0.076 (4)	0.008 (4)	−0.001 (4)	0.001 (3)
Cl1	0.0548 (9)	0.0363 (7)	0.0450 (8)	0.0057 (6)	−0.0117 (6)	−0.0036 (6)
O13	0.090 (4)	0.066 (3)	0.045 (3)	0.003 (3)	−0.022 (2)	−0.010 (2)
O14	0.060 (4)	0.161 (11)	0.085 (6)	0.047 (6)	−0.037 (4)	−0.066 (7)
O15	0.103 (8)	0.070 (5)	0.069 (4)	−0.023 (5)	−0.008 (5)	0.019 (3)
O16	0.122 (8)	0.025 (4)	0.076 (4)	0.008 (4)	−0.001 (4)	0.001 (3)

Zn—O1	1.973 (4)	C9—H9A	0.9800
Zn—N1	2.124 (4)	C9—H9B	0.9800
Zn—N2	2.216 (4)	C9—H9C	0.9800
Zn—N3	2.095 (4)	C10—C11	1.521 (7)
Zn—N4	2.153 (4)	C10—C12	1.534 (7)
O1—C19	1.286 (6)	C10—H10	1.0000
O2—C19	1.261 (7)	C11—H11A	0.9800
N1—C1	1.504 (6)	C11—H11B	0.9800
N1—C17	1.508 (6)	C11—H11C	0.9800
N1—H1N	0.882 (10)	C12—H12A	0.9900
N2—C3	1.473 (7)	C12—H12B	0.9900
N2—C4	1.500 (7)	C13—C14	1.518 (8)
N2—H2N	0.878 (10)	C13—C16	1.537 (7)
N3—C8	1.497 (7)	C13—C15	1.535 (8)
N3—C10	1.499 (6)	C14—H14A	0.9800
N3—H3N	0.879 (10)	C14—H14B	0.9800
N4—C12	1.478 (7)	C14—H14C	0.9800
N4—C13	1.511 (7)	C15—H15A	0.9800
N4—H4N	0.880 (10)	C15—H15B	0.9800
C1—C2	1.518 (7)	C15—H15C	0.9800
C1—C3	1.523 (8)	C16—C17	1.537 (7)
C1—H1	1.0000	C16—H16A	0.9900
C2—H2A	0.9800	C16—H16B	0.9900
C2—H2B	0.9800	C17—C18	1.524 (7)
C2—H2C	0.9800	C17—H17	1.0000
C3—H3A	0.9900	C18—H18A	0.9800
C3—H3B	0.9900	C18—H18B	0.9800
C4—C6	1.528 (9)	C18—H18C	0.9800
C4—C7	1.537 (8)	C19—C20	1.476 (8)
C4—C5	1.540 (8)	C20—H20A	0.9800
C5—H5A	0.9800	C20—H20B	0.9800
C5—H5B	0.9800	C20—H20C	0.9800
C5—H5C	0.9800	Cl—O6	1.420 (5)
C6—H6A	0.9800	Cl—O3	1.415 (4)
C6—H6B	0.9800	Cl—O4	1.422 (5)
C6—H6C	0.9800	Cl—O5	1.484 (5)
C7—C8	1.559 (8)	Cl1—O15	1.405 (7)
C7—H7A	0.9900	Cl1—O16	1.435 (7)
C7—H7B	0.9900	Cl1—O13	1.415 (4)
C8—C9	1.497 (8)	Cl1—O14	1.474 (8)
C8—H8	1.0000
O1—Zn—N3	128.04 (17)	C7—C8—H8	105.8
O1—Zn—N1	121.79 (16)	C8—C9—H9A	109.5
N3—Zn—N1	109.96 (17)	C8—C9—H9B	109.5
O1—Zn—N4	99.58 (16)	H9A—C9—H9B	109.5
N3—Zn—N4	82.75 (16)	C8—C9—H9C	109.5
N1—Zn—N4	91.23 (16)	H9A—C9—H9C	109.5
O1—Zn—N2	89.52 (16)	H9B—C9—H9C	109.5
N3—Zn—N2	92.08 (17)	N3—C10—C11	113.0 (4)
N1—Zn—N2	83.46 (17)	N3—C10—C12	107.5 (4)
N4—Zn—N2	170.89 (16)	C11—C10—C12	109.9 (4)
C19—O1—Zn	124.3 (4)	N3—C10—H10	108.7
C1—N1—C17	114.5 (4)	C11—C10—H10	108.7
C1—N1—Zn	105.6 (3)	C12—C10—H10	108.7
C17—N1—Zn	120.6 (3)	C10—C11—H11A	109.5
C1—N1—H1N	109 (4)	C10—C11—H11B	109.5
C17—N1—H1N	104 (4)	H11A—C11—H11B	109.5
Zn—N1—H1N	102 (4)	C10—C11—H11C	109.5
C3—N2—C4	117.2 (4)	H11A—C11—H11C	109.5
C3—N2—Zn	103.2 (3)	H11B—C11—H11C	109.5
C4—N2—Zn	119.4 (3)	N4—C12—C10	109.3 (4)
C3—N2—H2N	103 (4)	N4—C12—H12A	109.8
C4—N2—H2N	102 (4)	C10—C12—H12A	109.8
Zn—N2—H2N	111 (4)	N4—C12—H12B	109.8
C8—N3—C10	113.7 (4)	C10—C12—H12B	109.8
C8—N3—Zn	117.3 (3)	H12A—C12—H12B	108.3
C10—N3—Zn	109.0 (3)	N4—C13—C14	106.6 (4)
C8—N3—H3N	110 (4)	N4—C13—C16	110.4 (4)
C10—N3—H3N	103 (4)	C14—C13—C16	111.8 (5)
Zn—N3—H3N	102 (4)	N4—C13—C15	110.7 (4)
C12—N4—C13	115.7 (4)	C14—C13—C15	109.0 (5)
C12—N4—Zn	106.5 (3)	C16—C13—C15	108.4 (4)
C13—N4—Zn	118.1 (3)	C13—C14—H14A	109.5
C12—N4—H4N	109 (4)	C13—C14—H14B	109.5
C13—N4—H4N	104 (4)	H14A—C14—H14B	109.5
Zn—N4—H4N	102 (4)	C13—C14—H14C	109.5
N1—C1—C2	110.9 (4)	H14A—C14—H14C	109.5
N1—C1—C3	107.2 (4)	H14B—C14—H14C	109.5
C2—C1—C3	112.4 (4)	C13—C15—H15A	109.5
N1—C1—H1	108.8	C13—C15—H15B	109.5
C2—C1—H1	108.8	H15A—C15—H15B	109.5
C3—C1—H1	108.8	C13—C15—H15C	109.5
C1—C2—H2A	109.5	H15A—C15—H15C	109.5
C1—C2—H2B	109.5	H15B—C15—H15C	109.5
H2A—C2—H2B	109.5	C13—C16—C17	119.5 (4)
C1—C2—H2C	109.5	C13—C16—H16A	107.5
H2A—C2—H2C	109.5	C17—C16—H16A	107.5
H2B—C2—H2C	109.5	C13—C16—H16B	107.5
N2—C3—C1	110.9 (4)	C17—C16—H16B	107.5
N2—C3—H3A	109.5	H16A—C16—H16B	107.0
C1—C3—H3A	109.5	N1—C17—C18	111.9 (4)
N2—C3—H3B	109.5	N1—C17—C16	110.2 (4)
C1—C3—H3B	109.5	C18—C17—C16	109.2 (4)
H3A—C3—H3B	108.1	N1—C17—H17	108.5
N2—C4—C6	106.2 (5)	C18—C17—H17	108.5
N2—C4—C7	111.3 (4)	C16—C17—H17	108.5
C6—C4—C7	114.6 (5)	C17—C18—H18A	109.5
N2—C4—C5	111.8 (5)	C17—C18—H18B	109.5
C6—C4—C5	106.7 (5)	H18A—C18—H18B	109.5
C7—C4—C5	106.3 (5)	C17—C18—H18C	109.5
C4—C5—H5A	109.5	H18A—C18—H18C	109.5
C4—C5—H5B	109.5	H18B—C18—H18C	109.5
H5A—C5—H5B	109.5	O2—C19—O1	122.8 (5)
C4—C5—H5C	109.5	O2—C19—C20	120.7 (5)
H5A—C5—H5C	109.5	O1—C19—C20	116.4 (5)
H5B—C5—H5C	109.5	C19—C20—H20A	109.5
C4—C6—H6A	109.5	C19—C20—H20B	109.5
C4—C6—H6B	109.5	H20A—C20—H20B	109.5
H6A—C6—H6B	109.5	C19—C20—H20C	109.5
C4—C6—H6C	109.5	H20A—C20—H20C	109.5
H6A—C6—H6C	109.5	H20B—C20—H20C	109.5
H6B—C6—H6C	109.5	O6—Cl—O3	111.5 (4)
C4—C7—C8	122.4 (5)	O6—Cl—O4	113.3 (4)
C4—C7—H7A	106.7	O3—Cl—O4	111.8 (4)
C8—C7—H7A	106.7	O6—Cl—O5	106.0 (4)
C4—C7—H7B	106.7	O3—Cl—O5	108.3 (4)
C8—C7—H7B	106.7	O4—Cl—O5	105.6 (4)
H7A—C7—H7B	106.6	O15—Cl1—O16	111.4 (7)
N3—C8—C9	112.1 (5)	O15—Cl1—O13	113.1 (6)
N3—C8—C7	108.9 (4)	O16—Cl1—O13	110.8 (6)
C9—C8—C7	117.6 (5)	O15—Cl1—O14	108.5 (6)
N3—C8—H8	105.8	O16—Cl1—O14	105.8 (6)
C9—C8—H8	105.8	O13—Cl1—O14	106.9 (6)
N3—Zn—O1—C19	48.1 (5)	C3—N2—C4—C6	−153.3 (5)
N1—Zn—O1—C19	−137.6 (4)	Zn—N2—C4—C6	80.8 (5)
N4—Zn—O1—C19	−40.2 (4)	C3—N2—C4—C7	81.4 (6)
N2—Zn—O1—C19	140.4 (4)	Zn—N2—C4—C7	−44.5 (6)
O1—Zn—N1—C1	−66.6 (4)	C3—N2—C4—C5	−37.3 (7)
N3—Zn—N1—C1	108.6 (3)	Zn—N2—C4—C5	−163.1 (4)
N4—Zn—N1—C1	−168.7 (3)	N2—C4—C7—C8	63.1 (7)
N2—Zn—N1—C1	18.7 (3)	C6—C4—C7—C8	−57.4 (7)
O1—Zn—N1—C17	65.2 (4)	C5—C4—C7—C8	−175.0 (5)
N3—Zn—N1—C17	−119.6 (4)	C10—N3—C8—C9	57.6 (6)
N4—Zn—N1—C17	−36.9 (4)	Zn—N3—C8—C9	−71.3 (5)
N2—Zn—N1—C17	150.5 (4)	C10—N3—C8—C7	−170.5 (4)
O1—Zn—N2—C3	134.4 (3)	Zn—N3—C8—C7	60.6 (5)
N3—Zn—N2—C3	−97.6 (3)	C4—C7—C8—N3	−71.8 (7)
N1—Zn—N2—C3	12.3 (3)	C4—C7—C8—C9	57.1 (8)
O1—Zn—N2—C4	−93.4 (4)	C8—N3—C10—C11	65.2 (6)
N3—Zn—N2—C4	34.7 (4)	Zn—N3—C10—C11	−161.8 (4)
N1—Zn—N2—C4	144.5 (4)	C8—N3—C10—C12	−173.3 (4)
O1—Zn—N3—C8	48.5 (4)	Zn—N3—C10—C12	−40.3 (5)
N1—Zn—N3—C8	−126.3 (4)	C13—N4—C12—C10	−175.8 (4)
N4—Zn—N3—C8	145.0 (4)	Zn—N4—C12—C10	−42.4 (5)
N2—Zn—N3—C8	−42.5 (4)	N3—C10—C12—N4	56.2 (5)
O1—Zn—N3—C10	−82.6 (4)	C11—C10—C12—N4	179.6 (4)
N1—Zn—N3—C10	102.6 (3)	C12—N4—C13—C14	−165.8 (4)
N4—Zn—N3—C10	13.9 (3)	Zn—N4—C13—C14	66.3 (5)
N2—Zn—N3—C10	−173.6 (3)	C12—N4—C13—C16	72.6 (5)
O1—Zn—N4—C12	143.2 (3)	Zn—N4—C13—C16	−55.3 (5)
N3—Zn—N4—C12	15.7 (3)	C12—N4—C13—C15	−47.5 (6)
N1—Zn—N4—C12	−94.3 (3)	Zn—N4—C13—C15	−175.3 (3)
O1—Zn—N4—C13	−84.7 (4)	N4—C13—C16—C17	70.6 (6)
N3—Zn—N4—C13	147.8 (4)	C14—C13—C16—C17	−47.8 (6)
N1—Zn—N4—C13	37.8 (4)	C15—C13—C16—C17	−167.9 (5)
C17—N1—C1—C2	−58.5 (5)	C1—N1—C17—C18	−58.2 (6)
Zn—N1—C1—C2	76.7 (4)	Zn—N1—C17—C18	174.0 (3)
C17—N1—C1—C3	178.5 (4)	C1—N1—C17—C16	−179.8 (4)
Zn—N1—C1—C3	−46.3 (4)	Zn—N1—C17—C16	52.3 (5)
C4—N2—C3—C1	−175.7 (4)	C13—C16—C17—N1	−68.1 (6)
Zn—N2—C3—C1	−42.2 (5)	C13—C16—C17—C18	168.7 (5)
N1—C1—C3—N2	62.6 (5)	Zn—O1—C19—O2	−1.1 (7)
C2—C1—C3—N2	−59.5 (6)	Zn—O1—C19—C20	−178.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O4	0.88 (4)	2.14 (5)	3.017 (10)	177 (5)
N2—H2n···O2i	0.88 (4)	2.60 (4)	3.375 (6)	147 (4)
N3—H3n···O5	0.88 (3)	2.42 (3)	3.228 (8)	153 (5)
N4—H4n···O2	0.88 (3)	2.25 (3)	2.978 (6)	140 (4)

Table 1

Selected bond lengths (Å)

Zn—O1	1.973 (4)
Zn—N1	2.124 (4)
Zn—N2	2.216 (4)
Zn—N3	2.095 (4)
Zn—N4	2.153 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O4	0.88 (4)	2.14 (5)	3.017 (10)	177 (5)
N2—H2n⋯O2i	0.88 (4)	2.60 (4)	3.375 (6)	147 (4)
N3—H3n⋯O5	0.88 (3)	2.42 (3)	3.228 (8)	153 (5)
N4—H4n⋯O2	0.88 (3)	2.25 (3)	2.978 (6)	140 (4)

Symmetry code: (i) .