An octa-nuclear zinc(II) complex with 6,6'-dihydr-oxy-2,2'-[1,2-phenyl-enebis(nitrilo-methyl-idyne)]diphenol.

The asymmetric unit of the title compound, tetra-aqua-tetrakis-{μ(3)-6,6'-di-oxido-2,2'-[1,2-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}octa-zinc(II) dimethyl sulfoxide tetra-solvate dihydrate, [Zn(8)(C(20)H(12)N(2)O(4))(4)(H(2)O)(4)]·4C(2)H(6)OS·2H(2)O, contains one quarter of a Zn(II) octa-nuclear complex with symmetry, one dimethyl sulfoxide mol-ecule and one half of a water mol-ecule which lies on a twofold rotation axis. The Zn(II) atoms of the octa-nuclear complex have two different five-coordinate environments, viz. ZnN(2)O(3) and ZnO(5). All eight Zn(II) centers adopt a distorted square-pyramidal coordination; four Zn(II) ions have the N(2)O(2) tetra-dentate Schiff base ligand bound in a basal plane and the coordinated water mol-ecule occupying the apical site, while the remaing four Zn(II) ions are bound by five O atoms from three Schiff base ligands. In the crystal structure, Zn(II) complex mol-ecules, coordinated and uncoord-inated water mol-ecules and dimethyl sulfoxide mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming a three-dimensional framework.

Related literature

For related literatures on Schiff base ZnII coordination complexes, see: Basak et al. 2007 ▶; Collinson & Fenton (1996 ▶); Pal et al. (2005 ▶); Tarafder et al. (2002 ▶). For related structures, see: Eltayeb et al. (2007a ▶,b ▶,c ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Zn8(C20H12N2O4)4(H2O)4]·4C2H6OS·2H2O

M = 2321.03

Tetragonal,

a = 18.1324 (3) Å

c = 13.3813 (3) Å

V = 4399.56 (14) Å3

Z = 2

Mo Kα radiation

μ = 2.32 mm−1

T = 100.0 (1) K

0.57 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.352, T max = 0.796

26700 measured reflections

5851 independent reflections

3700 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.02

5851 reflections

314 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −1.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017340/ci2611sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017340/ci2611Isup2.hkl

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

[Zn8(C20H12N2O4)4(H2O)4]·4C2H6OS·2H2O	Z = 2
Mr = 2321.03	F000 = 2360
Tetragonal, P42/n	Dx = 1.752 Mg m−3
Hall symbol: -P 4bc	Mo Kα radiation λ = 0.71073 Å
a = 18.1324 (3) Å	Cell parameters from 5851 reflections
b = 18.1324 (3) Å	θ = 2.9–29.0º
c = 13.3813 (3) Å	µ = 2.32 mm−1
α = 90º	T = 100.0 (1) K
β = 90º	Needle, orange
γ = 90º	0.57 × 0.13 × 0.10 mm
V = 4399.56 (14) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5851 independent reflections
Radiation source: fine-focus sealed tube	3700 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.085
Detector resolution: 8.33 pixels mm-1	θmax = 29.0º
T = 100.0(1) K	θmin = 2.9º
ω scans	h = −24→11
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −24→24
Tmin = 0.352, Tmax = 0.796	l = −18→18
26700 measured reflections

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0592P)2 + 6.834P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5851 reflections	Δρmax = 0.67 e Å−3
314 parameters	Δρmin = −1.34 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Zn1	0.22916 (3)	0.46426 (3)	0.07015 (4)	0.01886 (13)
Zn2	0.34013 (2)	0.35177 (2)	0.24587 (4)	0.01728 (13)
O1	0.35359 (15)	0.25401 (15)	0.1791 (2)	0.0188 (6)
O2	0.28402 (15)	0.36961 (15)	0.1029 (2)	0.0192 (6)
O3	0.14565 (15)	0.43546 (15)	0.1585 (2)	0.0189 (6)
O4	0.05238 (16)	0.38411 (16)	0.2903 (3)	0.0277 (7)
N1	0.26712 (19)	0.45884 (18)	−0.0754 (3)	0.0210 (7)
N2	0.1627 (2)	0.54198 (19)	−0.0038 (3)	0.0233 (8)
C1	0.3139 (2)	0.3234 (2)	0.0380 (3)	0.0177 (8)
C2	0.3494 (2)	0.2598 (2)	0.0780 (3)	0.0182 (8)
C3	0.3795 (2)	0.2079 (2)	0.0141 (3)	0.0222 (9)
H3A	0.4019	0.1661	0.0407	0.027*
C4	0.3768 (3)	0.2170 (2)	−0.0899 (4)	0.0282 (10)
H4A	0.3952	0.1805	−0.1320	0.034*
C5	0.3471 (2)	0.2795 (2)	−0.1285 (3)	0.0248 (9)
H5A	0.3470	0.2861	−0.1974	0.030*
C6	0.3166 (2)	0.3342 (2)	−0.0672 (3)	0.0216 (9)
C7	0.2939 (2)	0.4005 (2)	−0.1172 (3)	0.0231 (9)
H7A	0.2990	0.4016	−0.1863	0.028*
C8	0.2508 (2)	0.5228 (2)	−0.1328 (3)	0.0234 (9)
C9	0.2866 (3)	0.5429 (3)	−0.2203 (4)	0.0296 (10)
H9A	0.3238	0.5133	−0.2462	0.035*
C10	0.2663 (3)	0.6077 (3)	−0.2689 (4)	0.0349 (12)
H10A	0.2893	0.6207	−0.3285	0.042*
C11	0.2123 (3)	0.6529 (3)	−0.2295 (4)	0.0326 (11)
H11A	0.1990	0.6959	−0.2626	0.039*
C12	0.1781 (3)	0.6342 (2)	−0.1410 (4)	0.0278 (10)
H12A	0.1428	0.6655	−0.1138	0.033*
C13	0.1960 (2)	0.5688 (2)	−0.0920 (3)	0.0218 (9)
C14	0.0969 (2)	0.5594 (2)	0.0204 (4)	0.0250 (9)
H14A	0.0727	0.5940	−0.0191	0.030*
C15	0.0574 (2)	0.5294 (2)	0.1044 (3)	0.0223 (9)
C16	−0.0143 (2)	0.5597 (2)	0.1196 (4)	0.0261 (10)
H16A	−0.0298	0.5988	0.0797	0.031*
C17	−0.0604 (2)	0.5332 (2)	0.1905 (4)	0.0269 (10)
H17A	−0.1065	0.5546	0.1998	0.032*
C18	−0.0388 (2)	0.4735 (2)	0.2496 (4)	0.0250 (9)
H18A	−0.0707	0.4551	0.2978	0.030*
C19	0.0295 (2)	0.4420 (2)	0.2369 (3)	0.0209 (9)
C20	0.0805 (2)	0.4700 (2)	0.1638 (3)	0.0199 (9)
S1	0.42019 (7)	0.60730 (7)	−0.06159 (11)	0.0376 (3)
O5	0.3672 (2)	0.6353 (2)	0.0183 (3)	0.0436 (9)
C21	0.5096 (3)	0.6047 (3)	−0.0076 (5)	0.0449 (14)
H21A	0.5122	0.5650	0.0397	0.067*
H21B	0.5192	0.6506	0.0258	0.067*
H21C	0.5457	0.5972	−0.0591	0.067*
C22	0.4357 (4)	0.6846 (3)	−0.1418 (5)	0.0504 (16)
H22A	0.3913	0.6957	−0.1778	0.076*
H22B	0.4744	0.6731	−0.1881	0.076*
H22C	0.4498	0.7266	−0.1023	0.076*
O1W	0.29110 (16)	0.53937 (16)	0.1423 (3)	0.0251 (7)
H1W1	0.321 (2)	0.5050 (19)	0.154 (4)	0.038*
H2W1	0.311 (2)	0.570 (2)	0.105 (3)	0.038*
O2W	0.2500	0.7500	0.0625 (6)	0.104 (3)
H1W2	0.278 (5)	0.724 (5)	0.026 (2)	0.156*

	U11	U22	U33	U12	U13	U23
Zn1	0.0204 (2)	0.0191 (2)	0.0171 (3)	0.00136 (18)	0.0007 (2)	0.0010 (2)
Zn2	0.0177 (2)	0.0191 (2)	0.0150 (2)	−0.00013 (18)	0.0004 (2)	−0.0005 (2)
O1	0.0245 (14)	0.0182 (13)	0.0139 (15)	0.0013 (11)	−0.0015 (13)	0.0006 (12)
O2	0.0229 (14)	0.0219 (14)	0.0128 (14)	0.0035 (11)	0.0021 (12)	−0.0020 (12)
O3	0.0182 (13)	0.0181 (13)	0.0205 (16)	0.0015 (10)	−0.0001 (12)	0.0022 (12)
O4	0.0263 (15)	0.0267 (15)	0.0302 (19)	0.0052 (12)	0.0069 (15)	0.0101 (15)
N1	0.0245 (17)	0.0203 (16)	0.0181 (19)	0.0016 (14)	0.0011 (16)	0.0018 (15)
N2	0.0261 (18)	0.0229 (17)	0.021 (2)	0.0033 (14)	0.0014 (17)	0.0014 (16)
C1	0.0195 (19)	0.0168 (18)	0.017 (2)	−0.0004 (15)	−0.0013 (17)	−0.0030 (17)
C2	0.0204 (18)	0.0192 (18)	0.015 (2)	0.0001 (15)	0.0052 (17)	−0.0002 (18)
C3	0.025 (2)	0.021 (2)	0.020 (2)	0.0031 (16)	0.0047 (19)	0.0000 (19)
C4	0.041 (3)	0.025 (2)	0.019 (2)	0.0074 (19)	0.003 (2)	−0.0046 (19)
C5	0.035 (2)	0.026 (2)	0.013 (2)	0.0031 (18)	0.0017 (19)	−0.0014 (19)
C6	0.023 (2)	0.023 (2)	0.019 (2)	0.0008 (16)	−0.0007 (19)	−0.0020 (19)
C7	0.024 (2)	0.030 (2)	0.015 (2)	0.0005 (17)	−0.0027 (19)	0.0018 (19)
C8	0.027 (2)	0.022 (2)	0.021 (2)	0.0005 (17)	−0.004 (2)	0.0010 (19)
C9	0.036 (3)	0.029 (2)	0.023 (2)	0.0043 (19)	0.002 (2)	0.004 (2)
C10	0.045 (3)	0.030 (2)	0.030 (3)	−0.002 (2)	0.007 (2)	0.011 (2)
C11	0.040 (3)	0.028 (2)	0.029 (3)	0.002 (2)	−0.002 (2)	0.009 (2)
C12	0.029 (2)	0.025 (2)	0.030 (3)	0.0036 (17)	0.001 (2)	0.002 (2)
C13	0.022 (2)	0.024 (2)	0.019 (2)	0.0000 (16)	−0.0007 (18)	0.0058 (18)
C14	0.029 (2)	0.024 (2)	0.022 (2)	0.0078 (17)	−0.001 (2)	0.0065 (19)
C15	0.026 (2)	0.0188 (19)	0.022 (2)	0.0027 (16)	−0.0011 (19)	−0.0004 (18)
C16	0.030 (2)	0.023 (2)	0.026 (3)	0.0071 (17)	−0.003 (2)	0.001 (2)
C17	0.027 (2)	0.027 (2)	0.026 (3)	0.0071 (18)	0.000 (2)	−0.001 (2)
C18	0.025 (2)	0.027 (2)	0.023 (2)	−0.0004 (17)	0.006 (2)	0.000 (2)
C19	0.0211 (19)	0.0185 (18)	0.023 (2)	−0.0011 (15)	−0.0010 (18)	−0.0030 (18)
C20	0.0210 (19)	0.0192 (19)	0.020 (2)	0.0004 (15)	−0.0038 (18)	−0.0025 (18)
S1	0.0380 (7)	0.0359 (7)	0.0389 (8)	−0.0037 (5)	0.0043 (6)	−0.0010 (6)
O5	0.044 (2)	0.045 (2)	0.042 (2)	−0.0087 (17)	0.0120 (19)	−0.0001 (19)
C21	0.038 (3)	0.057 (4)	0.039 (3)	−0.005 (2)	0.004 (3)	0.001 (3)
C22	0.062 (4)	0.042 (3)	0.048 (4)	0.007 (3)	0.021 (3)	0.005 (3)
O1W	0.0260 (16)	0.0203 (15)	0.0290 (19)	−0.0008 (12)	−0.0009 (14)	−0.0011 (14)
O2W	0.134 (8)	0.130 (8)	0.047 (5)	0.075 (6)	0.000	0.000

Zn1—O3	1.990 (3)	C8—C9	1.387 (7)
Zn1—O1W	2.012 (3)	C8—C13	1.407 (6)
Zn1—O2	2.032 (3)	C9—C10	1.393 (6)
Zn1—N1	2.069 (4)	C9—H9A	0.93
Zn1—N2	2.101 (4)	C10—C11	1.381 (7)
Zn1—H1W1	2.13 (5)	C10—H10A	0.93
Zn2—O4i	1.973 (3)	C11—C12	1.379 (7)
Zn2—O1ii	1.981 (3)	C11—H11A	0.93
Zn2—O1	2.000 (3)	C12—C13	1.393 (6)
Zn2—O3i	2.152 (3)	C12—H12A	0.93
Zn2—O2	2.191 (3)	C14—C15	1.439 (6)
O1—C2	1.359 (5)	C14—H14A	0.93
O1—Zn2i	1.981 (3)	C15—C20	1.403 (6)
O2—C1	1.323 (5)	C15—C16	1.426 (6)
O3—C20	1.339 (5)	C16—C17	1.353 (7)
O3—Zn2ii	2.152 (3)	C16—H16A	0.93
O4—C19	1.336 (5)	C17—C18	1.396 (6)
O4—Zn2ii	1.973 (3)	C17—H17A	0.93
N1—C7	1.291 (5)	C18—C19	1.374 (6)
N1—C8	1.423 (5)	C18—H18A	0.93
N2—C14	1.277 (5)	C19—C20	1.439 (6)
N2—C13	1.412 (6)	S1—O5	1.525 (4)
C1—C6	1.421 (6)	S1—C21	1.775 (6)
C1—C2	1.425 (5)	S1—C22	1.787 (6)
C2—C3	1.384 (6)	C21—H21A	0.96
C3—C4	1.402 (6)	C21—H21B	0.96
C3—H3A	0.93	C21—H21C	0.96
C4—C5	1.356 (6)	C22—H22A	0.96
C4—H4A	0.93	C22—H22B	0.96
C5—C6	1.402 (6)	C22—H22C	0.96
C5—H5A	0.93	O1W—H1W1	0.837 (19)
C6—C7	1.436 (6)	O1W—H2W1	0.833 (19)
C7—H7A	0.93	O2W—H1W2	0.846 (14)
O3—Zn1—O1W	108.50 (13)	N1—C7—H7A	116.9
O3—Zn1—O2	91.31 (11)	C6—C7—H7A	116.9
O1W—Zn1—O2	101.24 (12)	C9—C8—C13	120.2 (4)
O3—Zn1—N1	143.11 (13)	C9—C8—N1	124.8 (4)
O1W—Zn1—N1	107.36 (14)	C13—C8—N1	114.9 (4)
O2—Zn1—N1	90.00 (12)	C8—C9—C10	119.5 (4)
O3—Zn1—N2	91.11 (13)	C8—C9—H9A	120.3
O1W—Zn1—N2	95.28 (13)	C10—C9—H9A	120.3
O2—Zn1—N2	161.59 (13)	C11—C10—C9	120.6 (5)
N1—Zn1—N2	77.25 (14)	C11—C10—H10A	119.7
O3—Zn1—H1W1	111.9 (13)	C9—C10—H10A	119.7
O1W—Zn1—H1W1	23.1 (7)	C12—C11—C10	120.1 (4)
O2—Zn1—H1W1	78.4 (6)	C12—C11—H11A	120.0
N1—Zn1—H1W1	104.5 (13)	C10—C11—H11A	120.0
N2—Zn1—H1W1	117.4 (6)	C11—C12—C13	120.6 (4)
O4i—Zn2—O1ii	117.28 (13)	C11—C12—H12A	119.7
O4i—Zn2—O1	128.45 (13)	C13—C12—H12A	119.7
O1ii—Zn2—O1	110.27 (16)	C12—C13—C8	119.1 (4)
O4i—Zn2—O3i	78.59 (12)	C12—C13—N2	126.0 (4)
O1ii—Zn2—O3i	112.98 (12)	C8—C13—N2	114.9 (4)
O1—Zn2—O3i	100.78 (11)	N2—C14—C15	124.8 (4)
O4i—Zn2—O2	80.99 (12)	N2—C14—H14A	117.6
O1ii—Zn2—O2	92.30 (11)	C15—C14—H14A	117.6
O1—Zn2—O2	78.31 (11)	C20—C15—C16	119.2 (4)
O3i—Zn2—O2	152.81 (11)	C20—C15—C14	125.7 (4)
C2—O1—Zn2i	124.8 (2)	C16—C15—C14	114.8 (4)
C2—O1—Zn2	111.7 (2)	C17—C16—C15	121.7 (4)
Zn2i—O1—Zn2	122.36 (15)	C17—C16—H16A	119.1
C1—O2—Zn1	126.4 (3)	C15—C16—H16A	119.1
C1—O2—Zn2	106.8 (2)	C16—C17—C18	120.0 (4)
Zn1—O2—Zn2	122.72 (14)	C16—C17—H17A	120.0
C20—O3—Zn1	125.4 (3)	C18—C17—H17A	120.0
C20—O3—Zn2ii	111.3 (2)	C19—C18—C17	120.4 (4)
Zn1—O3—Zn2ii	123.20 (13)	C19—C18—H18A	119.8
C19—O4—Zn2ii	117.4 (3)	C17—C18—H18A	119.8
C7—N1—C8	120.9 (4)	O4—C19—C18	122.7 (4)
C7—N1—Zn1	124.9 (3)	O4—C19—C20	116.2 (4)
C8—N1—Zn1	113.6 (3)	C18—C19—C20	121.1 (4)
C14—N2—C13	121.7 (4)	O3—C20—C15	126.4 (4)
C14—N2—Zn1	125.6 (3)	O3—C20—C19	115.9 (4)
C13—N2—Zn1	112.3 (3)	C15—C20—C19	117.7 (4)
O2—C1—C6	125.2 (4)	O5—S1—C21	107.4 (3)
O2—C1—C2	116.8 (4)	O5—S1—C22	105.0 (2)
C6—C1—C2	117.9 (4)	C21—S1—C22	96.9 (3)
O1—C2—C3	122.7 (4)	S1—C21—H21A	109.5
O1—C2—C1	117.5 (3)	S1—C21—H21B	109.5
C3—C2—C1	119.8 (4)	H21A—C21—H21B	109.5
C2—C3—C4	121.3 (4)	S1—C21—H21C	109.5
C2—C3—H3A	119.4	H21A—C21—H21C	109.5
C4—C3—H3A	119.4	H21B—C21—H21C	109.5
C5—C4—C3	119.3 (4)	S1—C22—H22A	109.5
C5—C4—H4A	120.3	S1—C22—H22B	109.5
C3—C4—H4A	120.3	H22A—C22—H22B	109.5
C4—C5—C6	121.7 (4)	S1—C22—H22C	109.5
C4—C5—H5A	119.2	H22A—C22—H22C	109.5
C6—C5—H5A	119.2	H22B—C22—H22C	109.5
C5—C6—C1	119.7 (4)	Zn1—O1W—H1W1	87 (4)
C5—C6—C7	115.7 (4)	Zn1—O1W—H2W1	114 (4)
C1—C6—C7	124.5 (4)	H1W1—O1W—H2W1	109 (3)
N1—C7—C6	126.3 (4)
O4i—Zn2—O1—C2	−44.4 (3)	C6—C1—C2—C3	−5.4 (6)
O1ii—Zn2—O1—C2	112.0 (3)	O1—C2—C3—C4	−177.4 (4)
O3i—Zn2—O1—C2	−128.4 (2)	C1—C2—C3—C4	0.9 (6)
O2—Zn2—O1—C2	23.9 (2)	C2—C3—C4—C5	3.0 (7)
O4i—Zn2—O1—Zn2i	147.45 (15)	C3—C4—C5—C6	−2.3 (7)
O1ii—Zn2—O1—Zn2i	−56.06 (14)	C4—C5—C6—C1	−2.4 (7)
O3i—Zn2—O1—Zn2i	63.54 (17)	C4—C5—C6—C7	174.0 (4)
O2—Zn2—O1—Zn2i	−144.18 (17)	O2—C1—C6—C5	−177.2 (4)
O3—Zn1—O2—C1	130.5 (3)	C2—C1—C6—C5	6.2 (6)
O1W—Zn1—O2—C1	−120.3 (3)	O2—C1—C6—C7	6.7 (7)
N1—Zn1—O2—C1	−12.6 (3)	C2—C1—C6—C7	−169.9 (4)
N2—Zn1—O2—C1	33.0 (6)	C8—N1—C7—C6	176.2 (4)
O3—Zn1—O2—Zn2	−75.11 (16)	Zn1—N1—C7—C6	−13.8 (6)
O1W—Zn1—O2—Zn2	34.05 (18)	C5—C6—C7—N1	−177.3 (4)
N1—Zn1—O2—Zn2	141.76 (17)	C1—C6—C7—N1	−1.1 (7)
N2—Zn1—O2—Zn2	−172.6 (3)	C7—N1—C8—C9	−28.3 (7)
O4i—Zn2—O2—C1	107.0 (3)	Zn1—N1—C8—C9	160.6 (4)
O1ii—Zn2—O2—C1	−135.8 (2)	C7—N1—C8—C13	154.6 (4)
O1—Zn2—O2—C1	−25.5 (2)	Zn1—N1—C8—C13	−16.5 (5)
O3i—Zn2—O2—C1	65.3 (3)	C13—C8—C9—C10	−1.9 (7)
O4i—Zn2—O2—Zn1	−51.73 (17)	N1—C8—C9—C10	−179.0 (4)
O1ii—Zn2—O2—Zn1	65.53 (16)	C8—C9—C10—C11	1.6 (8)
O1—Zn2—O2—Zn1	175.75 (18)	C9—C10—C11—C12	0.2 (8)
O3i—Zn2—O2—Zn1	−93.4 (3)	C10—C11—C12—C13	−1.8 (7)
O1W—Zn1—O3—C20	87.5 (3)	C11—C12—C13—C8	1.5 (7)
O2—Zn1—O3—C20	−170.2 (3)	C11—C12—C13—N2	−177.0 (4)
N1—Zn1—O3—C20	−78.4 (4)	C9—C8—C13—C12	0.4 (7)
N2—Zn1—O3—C20	−8.4 (3)	N1—C8—C13—C12	177.7 (4)
O1W—Zn1—O3—Zn2ii	−95.24 (18)	C9—C8—C13—N2	179.0 (4)
O2—Zn1—O3—Zn2ii	7.07 (17)	N1—C8—C13—N2	−3.7 (6)
N1—Zn1—O3—Zn2ii	98.8 (2)	C14—N2—C13—C12	26.1 (7)
N2—Zn1—O3—Zn2ii	168.82 (18)	Zn1—N2—C13—C12	−159.8 (4)
O3—Zn1—N1—C7	−74.8 (4)	C14—N2—C13—C8	−152.4 (4)
O1W—Zn1—N1—C7	119.1 (3)	Zn1—N2—C13—C8	21.7 (5)
O2—Zn1—N1—C7	17.3 (4)	C13—N2—C14—C15	174.5 (4)
N2—Zn1—N1—C7	−149.3 (4)	Zn1—N2—C14—C15	1.3 (7)
O3—Zn1—N1—C8	95.8 (3)	N2—C14—C15—C20	−9.3 (8)
O1W—Zn1—N1—C8	−70.2 (3)	N2—C14—C15—C16	177.2 (4)
O2—Zn1—N1—C8	−172.0 (3)	C20—C15—C16—C17	0.7 (7)
N2—Zn1—N1—C8	21.4 (3)	C14—C15—C16—C17	174.7 (4)
O3—Zn1—N2—C14	5.9 (4)	C15—C16—C17—C18	−1.4 (7)
O1W—Zn1—N2—C14	−102.8 (4)	C16—C17—C18—C19	0.6 (7)
O2—Zn1—N2—C14	103.4 (5)	Zn2ii—O4—C19—C18	174.6 (3)
N1—Zn1—N2—C14	150.6 (4)	Zn2ii—O4—C19—C20	−5.1 (5)
O3—Zn1—N2—C13	−167.9 (3)	C17—C18—C19—O4	−178.9 (4)
O1W—Zn1—N2—C13	83.4 (3)	C17—C18—C19—C20	0.9 (7)
O2—Zn1—N2—C13	−70.4 (5)	Zn1—O3—C20—C15	4.3 (6)
N1—Zn1—N2—C13	−23.2 (3)	Zn2ii—O3—C20—C15	−173.3 (3)
Zn1—O2—C1—C6	3.8 (6)	Zn1—O3—C20—C19	−176.8 (3)
Zn2—O2—C1—C6	−153.8 (3)	Zn2ii—O3—C20—C19	5.7 (4)
Zn1—O2—C1—C2	−179.5 (3)	C16—C15—C20—O3	179.7 (4)
Zn2—O2—C1—C2	22.8 (4)	C14—C15—C20—O3	6.4 (7)
Zn2i—O1—C2—C3	−33.8 (5)	C16—C15—C20—C19	0.7 (6)
Zn2—O1—C2—C3	158.5 (3)	C14—C15—C20—C19	−172.5 (4)
Zn2i—O1—C2—C1	147.9 (3)	O4—C19—C20—O3	−0.8 (6)
Zn2—O1—C2—C1	−19.8 (4)	C18—C19—C20—O3	179.4 (4)
O2—C1—C2—O1	−4.0 (5)	O4—C19—C20—C15	178.2 (4)
C6—C1—C2—O1	173.0 (3)	C18—C19—C20—C15	−1.5 (6)
O2—C1—C2—C3	177.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4i	0.84 (4)	1.72 (4)	2.535 (4)	164 (5)
O2W—H1W2···O5	0.85 (8)	2.28 (9)	3.032 (4)	147 (4)
O1W—H2W1···O5	0.83 (4)	1.95 (4)	2.772 (5)	174 (4)
C3—H3A···O3iii	0.93	2.57	3.271 (5)	132
C21—H21C···O4iv	0.96	2.52	3.454 (7)	165
C21—H21B···Cg1v	0.96	2.81	3.475 (6)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4i	0.84 (4)	1.72 (4)	2.535 (4)	164 (5)
O2W—H1W2⋯O5	0.85 (8)	2.28 (9)	3.032 (4)	147 (4)
O1W—H2W1⋯O5	0.83 (4)	1.95 (4)	2.772 (5)	174 (4)
C3—H3A⋯O3ii	0.93	2.57	3.271 (5)	132
C21—H21C⋯O4iii	0.96	2.52	3.454 (7)	165
C21—H21B⋯Cg1iv	0.96	2.81	3.475 (6)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C1–C6 ring.