[μ-(4S,5S,15S,16S)-10,21-Di-tert-butyl-4,5,15,16-tetra-phenyl-3,6,14,17-tetra-aza-tricyclo-[17.3.1.1]tetra-cosa-1(23),8,10,12(24),19,21-hexa-ene-23,24-diolato-κN,N,O,O:NN,O,O]bis-[(acetato-κO)zinc(II)] ethanol disolvate.

In the title compound, [Zn(2)(C(36)H(42)N(4)O(2))(CH(3)COO)(2)]·2CH(3)CH(2)OH, a centrosymmetric dinuclear zinc macrocyclic complex is accompanied by two half-occupied ethanol solvent molecues resulting in a 1:2 macrocycle-solvent composition. The Zn(II) atom has a square-pyramidal geometry arising from an N(2)O(3) donor set, being coordinated by two N atoms and two O atoms from the macrocyclic ligand in the equatorial sites and one O atom from an acetate anion in the apical site. The two Zn(II) atoms are linked by two phenolate O atoms, generating a four-membered Zn(2)O(2) ring at the centre of the macrocycle. The tert-butyl group shows rotational disorder over two sets of sites in a 0.552 (12):0.448 (12) ratio. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds are seen and a short intra-molecular C-H⋯O contact occurs.

Related literature

For background to the biochemistry of zinc compounds, see: Lipscomb & Straeter (1996 ▶); Burley et al. (1990 ▶); Roderick & Mathews (1993 ▶); Bazzicalupi et al. (1997 ▶). For related structures, see: Dutta et al. (2005 ▶); Liu et al. (2007 ▶). For further synthetic details, see: Tian et al. (1999 ▶).

Experimental

Crystal data

[Zn2(C36H42N4O2)(C2H3O2)2]·2C2H6O

M = 903.70

Triclinic,

a = 9.0566 (3) Å

b = 10.8410 (5) Å

c = 14.2828 (5) Å

α = 71.246 (4)°

β = 86.514 (3)°

γ = 78.362 (3)°

V = 1300.56 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.97 mm−1

T = 293 K

0.45 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.748, T max = 0.824

11846 measured reflections

6368 independent reflections

4133 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.253

S = 1.05

6368 reflections

285 parameters

655 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.15 e Å−3

Δρmin = −0.77 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021990/hb2961sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021990/hb2961Isup2.hkl

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

[Zn2(C36H42N4O2)(C2H3O2)2]·2C2H6O	Z = 1
Mr = 903.70	F(000) = 476
Triclinic, P1	Dx = 1.154 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0566 (3) Å	Cell parameters from 2131 reflections
b = 10.8410 (5) Å	θ = 3.1–26.5°
c = 14.2828 (5) Å	µ = 0.97 mm−1
α = 71.246 (4)°	T = 293 K
β = 86.514 (3)°	Block, yellow
γ = 78.362 (3)°	0.45 × 0.25 × 0.20 mm
V = 1300.56 (9) Å3

Oxford Diffraction Gemini R Ultra diffractometer	6368 independent reflections
Radiation source: fine-focus sealed tube	4133 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 29.8°, θmin = 4.4°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −14→14
Tmin = 0.748, Tmax = 0.824	l = −18→19
11846 measured reflections

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.253	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.1644P)2] where P = (Fo2 + 2Fc2)/3
6368 reflections	(Δ/σ)max < 0.001
285 parameters	Δρmax = 1.15 e Å−3
655 restraints	Δρmin = −0.77 e Å−3

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	0.05562 (7)	0.12433 (7)	0.50054 (5)	0.0340 (3)
C1	−0.1270 (7)	−0.0328 (6)	0.6667 (4)	0.0348 (12)
C2	−0.0490 (7)	−0.0070 (7)	0.7384 (5)	0.0393 (13)
C3	−0.0831 (8)	−0.0639 (8)	0.8383 (5)	0.0466 (15)
H3	−0.0290	−0.0493	0.8858	0.056*
C4	0.0649 (7)	0.0818 (7)	0.7131 (5)	0.0414 (13)
H4A	0.0126	0.1736	0.6901	0.050*
H4B	0.1207	0.0693	0.7724	0.050*
C5	0.3043 (7)	0.1208 (6)	0.6217 (5)	0.0378 (12)
C6	0.3920 (8)	0.1117 (7)	0.7007 (6)	0.0465 (14)
H6	0.3657	0.0661	0.7646	0.056*
C7	0.5162 (8)	0.1685 (8)	0.6863 (6)	0.0509 (15)
H7	0.5743	0.1609	0.7401	0.061*
C8	0.5554 (8)	0.2371 (8)	0.5923 (6)	0.0489 (15)
H8	0.6404	0.2755	0.5821	0.059*
C9	0.4671 (7)	0.2484 (7)	0.5129 (6)	0.0454 (14)
H9	0.4931	0.2953	0.4493	0.055*
C10	0.3420 (7)	0.1915 (6)	0.5269 (5)	0.0375 (12)
C11	0.3368 (7)	0.1223 (7)	0.3804 (5)	0.0397 (13)
H11A	0.3798	0.0336	0.4223	0.048*
H11B	0.4192	0.1649	0.3484	0.048*
C12	0.2376 (7)	0.1125 (7)	0.3023 (5)	0.0397 (13)
C13	0.2679 (8)	0.1641 (8)	0.2016 (5)	0.0513 (15)
H13	0.3412	0.2163	0.1820	0.062*
C14	0.1915 (9)	0.1397 (8)	0.1302 (5)	0.0530 (16)
C15	0.2210 (10)	0.2038 (10)	0.0195 (6)	0.070 (2)
C16	0.0903 (18)	0.274 (2)	−0.0392 (19)	0.106 (6)*	0.448 (12)
H16A	0.0088	0.2276	−0.0169	0.159*	0.448 (12)
H16B	0.1117	0.2812	−0.1072	0.159*	0.448 (12)
H16C	0.0625	0.3617	−0.0331	0.159*	0.448 (12)
C17	0.3466 (18)	0.269 (2)	−0.0069 (17)	0.078 (5)*	0.448 (12)
H17A	0.4286	0.2207	0.0380	0.117*	0.448 (12)
H17B	0.3183	0.3576	−0.0035	0.117*	0.448 (12)
H17C	0.3774	0.2721	−0.0730	0.117*	0.448 (12)
C18	0.276 (3)	0.084 (2)	−0.022 (2)	0.101 (6)*	0.448 (12)
H18A	0.3649	0.0287	0.0136	0.151*	0.448 (12)
H18B	0.2996	0.1178	−0.0908	0.151*	0.448 (12)
H18C	0.1983	0.0336	−0.0136	0.151*	0.448 (12)
C16'	0.146 (3)	0.3448 (14)	−0.0045 (17)	0.106 (5)*	0.552 (12)
H16D	0.0426	0.3503	0.0157	0.158*	0.552 (12)
H16E	0.1510	0.3878	−0.0745	0.158*	0.552 (12)
H16F	0.1963	0.3879	0.0297	0.158*	0.552 (12)
C17'	0.373 (3)	0.163 (3)	0.0001 (18)	0.106 (5)*	0.552 (12)
H17D	0.3988	0.0676	0.0228	0.160*	0.552 (12)
H17E	0.4347	0.1978	0.0340	0.160*	0.552 (12)
H17F	0.3908	0.1950	−0.0697	0.160*	0.552 (12)
C18'	0.154 (2)	0.1537 (17)	−0.0493 (15)	0.083 (4)*	0.552 (12)
H18D	0.0463	0.1770	−0.0471	0.124*	0.552 (12)
H18E	0.1845	0.0589	−0.0303	0.124*	0.552 (12)
H18F	0.1882	0.1926	−0.1152	0.124*	0.552 (12)
C19	−0.1180 (8)	0.3676 (7)	0.4525 (7)	0.0524 (18)
C20	−0.2183 (11)	0.4959 (9)	0.3983 (7)	0.074 (3)
H20A	−0.2489	0.4915	0.3365	0.110*
H20B	−0.1644	0.5672	0.3861	0.110*
H20C	−0.3057	0.5112	0.4376	0.110*
C21	0.192 (3)	0.573 (3)	0.260 (2)	0.107 (7)*	0.50
H21A	0.2097	0.6567	0.2627	0.129*	0.50
H21B	0.0950	0.5895	0.2286	0.129*	0.50
C22	0.308 (3)	0.525 (3)	0.197 (2)	0.117 (7)*	0.50
H22A	0.3097	0.5925	0.1341	0.176*	0.50
H22B	0.2863	0.4467	0.1867	0.176*	0.50
H22C	0.4052	0.5031	0.2281	0.176*	0.50
C23	0.690 (2)	0.287 (2)	0.1224 (14)	0.081 (5)	0.50
H23A	0.7180	0.3421	0.0591	0.121*	0.50
H23B	0.5824	0.3020	0.1279	0.121*	0.50
H23C	0.7284	0.1956	0.1289	0.121*	0.50
C24	0.7513 (19)	0.3194 (16)	0.1974 (12)	0.058 (4)	0.50
H24A	0.7141	0.4124	0.1901	0.070*	0.50
H24B	0.8602	0.3056	0.1912	0.070*	0.50
O1	−0.0909 (5)	0.2773 (5)	0.4110 (4)	0.0537 (13)
O2	−0.0635 (7)	0.3485 (6)	0.5334 (5)	0.0669 (15)
O3	−0.1018 (5)	0.0163 (4)	0.5695 (3)	0.0338 (9)
O4	0.1846 (10)	0.4916 (7)	0.3531 (5)	0.0344 (18)	0.50
H4	0.1170	0.5264	0.3826	0.052*	0.50
O5	0.7114 (8)	0.2386 (7)	0.2940 (5)	0.0252 (15)	0.50
H5	0.7511	0.2567	0.3367	0.038*	0.50
H2N	0.205 (8)	−0.030 (3)	0.652 (5)	0.050 (6)*
H1N	0.225 (12)	0.271 (6)	0.394 (5)	0.095 (4)*
N2	0.1736 (6)	0.0556 (5)	0.6353 (4)	0.0366 (11)
N1	0.2504 (6)	0.2002 (5)	0.4438 (4)	0.0342 (11)

	U11	U22	U33	U12	U13	U23
Zn1	0.0304 (4)	0.0382 (4)	0.0374 (5)	−0.0082 (3)	0.0014 (3)	−0.0165 (3)
C1	0.031 (3)	0.042 (3)	0.036 (3)	−0.006 (2)	0.003 (2)	−0.019 (2)
C2	0.035 (3)	0.049 (3)	0.041 (3)	−0.009 (2)	0.001 (2)	−0.024 (3)
C3	0.043 (3)	0.065 (4)	0.038 (3)	−0.013 (3)	0.000 (3)	−0.022 (3)
C4	0.040 (3)	0.052 (3)	0.040 (3)	−0.015 (2)	0.003 (2)	−0.022 (2)
C5	0.029 (2)	0.044 (3)	0.047 (3)	−0.009 (2)	−0.001 (2)	−0.023 (2)
C6	0.040 (3)	0.058 (3)	0.049 (3)	−0.012 (3)	−0.002 (3)	−0.026 (3)
C7	0.038 (3)	0.063 (4)	0.061 (4)	−0.011 (3)	−0.009 (3)	−0.030 (3)
C8	0.032 (3)	0.061 (4)	0.060 (4)	−0.016 (3)	−0.005 (3)	−0.024 (3)
C9	0.036 (3)	0.054 (3)	0.053 (3)	−0.015 (3)	0.003 (3)	−0.023 (3)
C10	0.030 (2)	0.041 (3)	0.048 (3)	−0.008 (2)	0.000 (2)	−0.023 (2)
C11	0.032 (3)	0.052 (3)	0.044 (3)	−0.014 (2)	0.006 (2)	−0.024 (2)
C12	0.035 (3)	0.051 (3)	0.040 (3)	−0.015 (2)	0.007 (2)	−0.022 (3)
C13	0.048 (3)	0.067 (4)	0.046 (3)	−0.025 (3)	0.010 (3)	−0.021 (3)
C14	0.055 (3)	0.069 (4)	0.042 (3)	−0.021 (3)	0.009 (3)	−0.024 (3)
C15	0.071 (4)	0.095 (5)	0.050 (4)	−0.035 (4)	0.011 (3)	−0.021 (4)
C19	0.035 (4)	0.041 (4)	0.077 (5)	−0.008 (3)	0.003 (4)	−0.014 (4)
C20	0.077 (6)	0.055 (5)	0.083 (6)	0.014 (4)	−0.017 (5)	−0.027 (5)
C23	0.067 (10)	0.097 (12)	0.058 (9)	−0.011 (9)	0.004 (8)	0.000 (9)
C24	0.060 (9)	0.051 (8)	0.062 (9)	−0.008 (7)	−0.013 (7)	−0.016 (7)
O1	0.042 (3)	0.040 (3)	0.078 (4)	−0.001 (2)	−0.005 (2)	−0.021 (2)
O2	0.067 (4)	0.057 (3)	0.069 (4)	−0.002 (3)	−0.012 (3)	−0.014 (3)
O3	0.033 (2)	0.039 (2)	0.033 (2)	−0.0101 (17)	0.0037 (17)	−0.0157 (18)
O4	0.056 (5)	0.015 (3)	0.024 (4)	−0.001 (3)	0.009 (4)	0.000 (3)
O5	0.026 (4)	0.024 (4)	0.027 (4)	−0.008 (3)	−0.004 (3)	−0.008 (3)
N2	0.034 (3)	0.042 (3)	0.040 (3)	−0.010 (2)	0.000 (2)	−0.019 (2)
N1	0.032 (3)	0.037 (3)	0.037 (3)	−0.005 (2)	0.000 (2)	−0.017 (2)

Zn1—O1	2.025 (5)	C16—H16A	0.9600
Zn1—O3	2.033 (4)	C16—H16B	0.9600
Zn1—O3i	2.043 (4)	C16—H16C	0.9600
Zn1—N2	2.100 (5)	C17—H17A	0.9600
Zn1—N1	2.104 (5)	C17—H17B	0.9600
Zn1—Zn1i	3.0670 (13)	C17—H17C	0.9600
C1—O3	1.341 (7)	C18—H18A	0.9600
C1—C2	1.407 (8)	C18—H18B	0.9600
C1—C12i	1.412 (9)	C18—H18C	0.9600
C2—C3	1.403 (9)	C16'—H16D	0.9600
C2—C4	1.501 (9)	C16'—H16E	0.9600
C3—C14i	1.370 (10)	C16'—H16F	0.9600
C3—H3	0.9300	C17'—H17D	0.9600
C4—N2	1.496 (8)	C17'—H17E	0.9600
C4—H4A	0.9700	C17'—H17F	0.9600
C4—H4B	0.9700	C18'—H18D	0.9600
C5—C6	1.385 (9)	C18'—H18E	0.9600
C5—C10	1.386 (9)	C18'—H18F	0.9600
C5—N2	1.470 (8)	C19—O2	1.223 (10)
C6—C7	1.363 (10)	C19—O1	1.276 (9)
C6—H6	0.9300	C19—C20	1.497 (11)
C7—C8	1.374 (11)	C20—H20A	0.9600
C7—H7	0.9300	C20—H20B	0.9600
C8—C9	1.386 (10)	C20—H20C	0.9600
C8—H8	0.9300	C21—O4	1.34 (3)
C9—C10	1.371 (9)	C21—C22	1.47 (3)
C9—H9	0.9300	C21—H21A	0.9700
C10—N1	1.456 (8)	C21—H21B	0.9700
C11—N1	1.511 (7)	C22—H22A	0.9600
C11—C12	1.517 (9)	C22—H22B	0.9600
C11—H11A	0.9700	C22—H22C	0.9600
C11—H11B	0.9700	C23—C24	1.40 (2)
C12—C13	1.398 (10)	C23—H23A	0.9600
C12—C1i	1.412 (9)	C23—H23B	0.9600
C13—C14	1.387 (10)	C23—H23C	0.9600
C13—H13	0.9300	C24—O5	1.446 (18)
C14—C3i	1.370 (10)	C24—H24A	0.9700
C14—C15	1.540 (11)	C24—H24B	0.9700
C15—C17'	1.40 (2)	O3—Zn1i	2.043 (4)
C15—C16	1.426 (11)	O4—H4	0.8200
C15—C17	1.426 (11)	O5—H5	0.8200
C15—C18'	1.475 (17)	N2—H2N	0.87 (3)
C15—C16'	1.479 (11)	N1—H1N	0.86 (3)
C15—C18	1.57 (2)
O1—Zn1—O3	96.05 (19)	H16A—C16—H16B	109.5
O1—Zn1—O3i	105.62 (19)	C15—C16—H16C	109.5
O3—Zn1—O3i	82.40 (17)	H16A—C16—H16C	109.5
O1—Zn1—N2	144.5 (2)	H16B—C16—H16C	109.5
O3—Zn1—N2	88.07 (18)	C15—C17—H17A	109.5
O3i—Zn1—N2	109.82 (19)	C15—C17—H17B	109.5
O1—Zn1—N1	95.6 (2)	H17A—C17—H17B	109.5
O3—Zn1—N1	168.18 (18)	C15—C17—H17C	109.5
O3i—Zn1—N1	92.33 (17)	H17A—C17—H17C	109.5
N2—Zn1—N1	83.8 (2)	H17B—C17—H17C	109.5
O1—Zn1—Zn1i	104.44 (14)	C15—C18—H18A	109.5
O3—Zn1—Zn1i	41.32 (11)	C15—C18—H18B	109.5
O3i—Zn1—Zn1i	41.08 (11)	H18A—C18—H18B	109.5
N2—Zn1—Zn1i	101.75 (15)	C15—C18—H18C	109.5
N1—Zn1—Zn1i	132.53 (13)	H18A—C18—H18C	109.5
O3—C1—C2	122.6 (6)	H18B—C18—H18C	109.5
O3—C1—C12i	118.4 (5)	C15—C16'—H16D	109.5
C2—C1—C12i	119.0 (6)	C15—C16'—H16E	109.5
C3—C2—C1	118.2 (6)	H16D—C16'—H16E	109.5
C3—C2—C4	118.5 (6)	C15—C16'—H16F	109.5
C1—C2—C4	123.2 (6)	H16D—C16'—H16F	109.5
C14i—C3—C2	123.6 (6)	H16E—C16'—H16F	109.5
C14i—C3—H3	118.2	C15—C17'—H17D	109.5
C2—C3—H3	118.2	C15—C17'—H17E	109.5
N2—C4—C2	112.9 (5)	H17D—C17'—H17E	109.5
N2—C4—H4A	109.0	C15—C17'—H17F	109.5
C2—C4—H4A	109.0	H17D—C17'—H17F	109.5
N2—C4—H4B	109.0	H17E—C17'—H17F	109.5
C2—C4—H4B	109.0	C15—C18'—H18D	109.5
H4A—C4—H4B	107.8	C15—C18'—H18E	109.5
C6—C5—C10	119.2 (6)	H18D—C18'—H18E	109.5
C6—C5—N2	121.9 (6)	C15—C18'—H18F	109.5
C10—C5—N2	118.9 (5)	H18D—C18'—H18F	109.5
C7—C6—C5	121.1 (7)	H18E—C18'—H18F	109.5
C7—C6—H6	119.5	O2—C19—O1	120.5 (7)
C5—C6—H6	119.5	O2—C19—C20	122.1 (7)
C6—C7—C8	119.9 (7)	O1—C19—C20	117.4 (8)
C6—C7—H7	120.0	C19—C20—H20A	109.5
C8—C7—H7	120.0	C19—C20—H20B	109.5
C7—C8—C9	119.4 (6)	H20A—C20—H20B	109.5
C7—C8—H8	120.3	C19—C20—H20C	109.5
C9—C8—H8	120.3	H20A—C20—H20C	109.5
C10—C9—C8	121.0 (7)	H20B—C20—H20C	109.5
C10—C9—H9	119.5	O4—C21—C22	116 (2)
C8—C9—H9	119.5	O4—C21—H21A	108.2
C9—C10—C5	119.4 (6)	C22—C21—H21A	108.2
C9—C10—N1	121.4 (6)	O4—C21—H21B	108.2
C5—C10—N1	119.2 (5)	C22—C21—H21B	108.2
N1—C11—C12	112.1 (5)	H21A—C21—H21B	107.4
N1—C11—H11A	109.2	C21—C22—H22A	109.5
C12—C11—H11A	109.2	C21—C22—H22B	109.5
N1—C11—H11B	109.2	H22A—C22—H22B	109.5
C12—C11—H11B	109.2	C21—C22—H22C	109.5
H11A—C11—H11B	107.9	H22A—C22—H22C	109.5
C13—C12—C1i	119.9 (6)	H22B—C22—H22C	109.5
C13—C12—C11	121.2 (6)	C24—C23—H23A	109.5
C1i—C12—C11	118.3 (6)	C24—C23—H23B	109.5
C14—C13—C12	121.6 (7)	H23A—C23—H23B	109.5
C14—C13—H13	119.2	C24—C23—H23C	109.5
C12—C13—H13	119.2	H23A—C23—H23C	109.5
C3i—C14—C13	117.6 (7)	H23B—C23—H23C	109.5
C3i—C14—C15	121.7 (7)	C23—C24—O5	111.0 (14)
C13—C14—C15	120.6 (7)	C23—C24—H24A	109.4
C17'—C15—C16	135.3 (16)	O5—C24—H24A	109.4
C17'—C15—C17	45.7 (11)	C23—C24—H24B	109.4
C16—C15—C17	113.1 (11)	O5—C24—H24B	109.4
C17'—C15—C18'	98.4 (13)	H24A—C24—H24B	108.0
C16—C15—C18'	56.2 (11)	C19—O1—Zn1	106.4 (5)
C17—C15—C18'	122.3 (14)	C1—O3—Zn1	128.5 (4)
C17'—C15—C16'	123.3 (15)	C1—O3—Zn1i	113.8 (4)
C16—C15—C16'	50.1 (11)	Zn1—O3—Zn1i	97.60 (17)
C17—C15—C16'	78.5 (13)	C21—O4—H4	109.5
C18'—C15—C16'	105.0 (10)	C24—O5—H5	109.5
C17'—C15—C14	108.8 (12)	C5—N2—C4	114.9 (5)
C16—C15—C14	115.4 (13)	C5—N2—Zn1	107.9 (4)
C17—C15—C14	118.0 (11)	C4—N2—Zn1	107.6 (4)
C18'—C15—C14	116.1 (10)	C5—N2—H2N	109 (5)
C16'—C15—C14	105.7 (12)	C4—N2—H2N	107 (5)
C17'—C15—C18	58.0 (8)	Zn1—N2—H2N	110 (5)
C16—C15—C18	102.3 (11)	C10—N1—C11	110.9 (5)
C17—C15—C18	99.6 (14)	C10—N1—Zn1	108.1 (4)
C18'—C15—C18	46.8 (10)	C11—N1—Zn1	110.1 (3)
C16'—C15—C18	145.6 (14)	C10—N1—H1N	124 (7)
C14—C15—C18	105.2 (12)	C11—N1—H1N	93 (7)
C15—C16—H16A	109.5	Zn1—N1—H1N	109 (7)
C15—C16—H16B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2	0.97	2.45	3.246 (10)	139
N1—H1N···O4	0.86 (7)	2.23 (7)	2.952 (9)	141 (6)
N2—H2N···O5ii	0.87 (4)	2.13 (4)	2.999 (9)	175 (4)
O4—H4···O2iii	0.82	2.06	2.768 (10)	145
O5—H5···O1iv	0.82	1.92	2.700 (9)	159

Table 1

Selected bond lengths (Å)

Zn1—O1	2.025 (5)
Zn1—O3	2.033 (4)
Zn1—O3i	2.043 (4)
Zn1—N2	2.100 (5)
Zn1—N1	2.104 (5)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2	0.97	2.45	3.246 (10)	139
N1—H1N⋯O4	0.86 (7)	2.23 (7)	2.952 (9)	141 (6)
N2—H2N⋯O5ii	0.87 (4)	2.13 (4)	2.999 (9)	175 (4)
O4—H4⋯O2iii	0.82	2.06	2.768 (10)	145
O5—H5⋯O1iv	0.82	1.92	2.700 (9)	159

Symmetry codes: (ii) ; (iii) ; (iv) .