Guanidinium (aqua-2κO)(4-hydr-oxy-6-carboxy-pyridine-2-carboxyl-ato-2κO,N,O)(μ-4-hydroxy-pyridine-2,6-dicarboxyl-ato-1:2κO,N,O:O)(4-hydroxy-pyridine-2,6-dicarboxyl-ato-1κO,N,O)dizincate(II) dihydrate.

The title compound, (CH(6)N(3))[Zn(2)(C(7)H(3)NO(5))(2)(C(7)H(4)NO(5))(H(2)O)]·2H(2)O, has an anionic binuclear complex of Zn(II) balanced with a guanidinium cation. There are two uncoord-inated water mol-ecules in the structure. The asymmetric unit of the compound has two different coordination types (the coordination of Zn1 is distorted trigonal-bipyramidal, while that of Zn2 is distorted octahedral) of Zn(II) in the crystal structure that are bridged to each other via one hypydc(2-) group (hypydcH(2) is 4-hydroxy-pyridine-2,6-dicarboxylic acid). A variety of inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds involving water mol-ecules, cations and anions, and also a weak π-π inter-action [3.798 (1) Å], are responsible for extending the structure into a three-dimensional network.

Related literature

For related literature, see: Moghimi, Aghabozorg, Sheshmani, et al. (2005 ▶); Moghimi, Aghabozorg, Soleimannejad et al. (2005 ▶); Aghabozorg et al. (2008 ▶); Ranjbar et al. (2002 ▶); Sharif et al. (2007 ▶).

Experimental

Crystal data

(CH6N3)[Zn2(n class="CellLine">C7H3NO5)2(C7H4NO5)(H2O)]·2H2O

M = 789.20

Triclinic,

a = 9.1077 (12) Å

b = 9.2900 (12) Å

c = 16.347 (3) Å

α = 96.018 (4)°

β = 99.229 (4)°

γ = 91.760 (7)°

V = 1356.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.87 mm−1

T = 100 (2) K

0.21 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.695, T max = 0.807

19615 measured reflections

8987 independent reflections

6765 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.089

S = 1.00

8987 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: APEX2; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003930/om2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003930/om2211Isup2.hkl

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

(CH6N3)[Zn2(C7H3N1O5)2(C7H4N1O5)(H2O)]·2H2O	Z = 2
Mr = 789.20	F000 = 800
Triclinic, P1	Dx = 1.933 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.1077 (12) Å	Cell parameters from 540 reflections
b = 9.2900 (12) Å	θ = 2.8–27.2º
c = 16.347 (3) Å	µ = 1.87 mm−1
α = 96.018 (4)º	T = 100 (2) K
β = 99.229 (4)º	Prism, colourless
γ = 91.760 (7)º	0.21 × 0.15 × 0.12 mm
V = 1356.1 (3) Å3

Bruker APEXII CCD area-detector diffractometer	8987 independent reflections
Radiation source: fine-focus sealed tube	6765 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
T = 100(2) K	θmax = 31.5º
ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.695, Tmax = 0.807	k = −13→13
19615 measured reflections	l = −23→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
8987 reflections	Δρmax = 0.59 e Å−3
433 parameters	Δρmin = −0.56 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.43557 (3)	0.16470 (2)	0.258415 (14)	0.01093 (6)
Zn2	0.18238 (3)	0.50031 (2)	0.310910 (14)	0.01149 (6)
N1	0.36197 (18)	0.12238 (18)	0.13492 (10)	0.0107 (3)
N2	0.18759 (19)	0.47854 (18)	0.18862 (10)	0.0110 (3)
N3	0.23352 (18)	0.48751 (17)	0.43438 (10)	0.0099 (3)
N4	0.3338 (2)	−0.10238 (19)	0.43263 (11)	0.0157 (4)
H4A	0.3274	−0.1284	0.3788	0.019*
H4B	0.3992	−0.1414	0.4684	0.019*
N5	0.2568 (2)	0.03721 (19)	0.54093 (11)	0.0156 (4)
H5A	0.3235	−0.0004	0.5767	0.019*
H5B	0.1978	0.1023	0.5589	0.019*
N6	0.1460 (2)	0.0554 (2)	0.40657 (11)	0.0148 (4)
H6A	0.1387	0.0300	0.3526	0.018*
H6B	0.0875	0.1205	0.4252	0.018*
O1	0.59008 (16)	0.29141 (15)	0.21141 (9)	0.0137 (3)
O2	0.63792 (18)	0.36048 (18)	0.09069 (9)	0.0215 (3)
O3	0.21305 (16)	0.00289 (16)	0.23874 (9)	0.0145 (3)
O4	0.07106 (17)	−0.13769 (16)	0.13266 (9)	0.0153 (3)
H4C	0.0149	−0.1491	0.1678	0.018*
O5	0.27628 (16)	0.02110 (16)	−0.11860 (9)	0.0143 (3)
H5C	0.2173	−0.0520	−0.1315	0.017*
O6	0.34222 (17)	0.67780 (16)	0.29445 (9)	0.0146 (3)
O7	0.44783 (17)	0.76832 (16)	0.19381 (9)	0.0172 (3)
O8	0.00950 (16)	0.32407 (16)	0.26076 (9)	0.0143 (3)
O9	−0.05698 (17)	0.17203 (16)	0.14388 (9)	0.0159 (3)
O10	0.19172 (17)	0.42385 (16)	−0.06347 (9)	0.0171 (3)
H10A	0.2427	0.4907	−0.0779	0.021*
O11	0.04286 (16)	0.64962 (15)	0.35657 (9)	0.0135 (3)
O12	−0.01195 (16)	0.76190 (15)	0.47515 (9)	0.0147 (3)
O13	0.35192 (16)	0.31130 (15)	0.32996 (9)	0.0129 (3)
O14	0.49768 (17)	0.21787 (16)	0.43224 (9)	0.0166 (3)
O15	0.31816 (17)	0.47150 (16)	0.68773 (9)	0.0160 (3)
H15	0.3166	0.5532	0.7150	0.019*
C1	0.4418 (2)	0.1863 (2)	0.08551 (12)	0.0107 (4)
C2	0.4131 (2)	0.1565 (2)	−0.00030 (12)	0.0122 (4)
H2A	0.4696	0.2048	−0.0342	0.015*
C3	0.2999 (2)	0.0541 (2)	−0.03617 (12)	0.0110 (4)
C4	0.2169 (2)	−0.0136 (2)	0.01602 (12)	0.0115 (4)
H4D	0.1386	−0.0835	−0.0065	0.014*
C5	0.2529 (2)	0.0247 (2)	0.10110 (12)	0.0112 (4)
C6	0.5679 (2)	0.2891 (2)	0.13240 (13)	0.0127 (4)
C7	0.1755 (2)	−0.0385 (2)	0.16419 (12)	0.0118 (4)
C8	0.2775 (2)	0.5651 (2)	0.15616 (12)	0.0116 (4)
C9	0.2842 (2)	0.5519 (2)	0.07219 (13)	0.0136 (4)
H9A	0.3492	0.6146	0.0506	0.016*
C10	0.1938 (2)	0.4448 (2)	0.01905 (12)	0.0127 (4)
C11	0.1009 (2)	0.3538 (2)	0.05356 (12)	0.0127 (4)
H11A	0.0391	0.2794	0.0193	0.015*
C12	0.1010 (2)	0.3745 (2)	0.13860 (12)	0.0109 (4)
C13	0.3656 (2)	0.6799 (2)	0.22034 (13)	0.0124 (4)
C14	0.0089 (2)	0.2824 (2)	0.18459 (12)	0.0118 (4)
C15	0.1664 (2)	0.5794 (2)	0.48423 (12)	0.0109 (4)
C16	0.1924 (2)	0.5833 (2)	0.57028 (12)	0.0123 (4)
H16A	0.1455	0.6509	0.6041	0.015*
C17	0.2895 (2)	0.4848 (2)	0.60600 (12)	0.0123 (4)
C18	0.3603 (2)	0.3900 (2)	0.55377 (12)	0.0116 (4)
H18A	0.4279	0.3230	0.5764	0.014*
C19	0.3294 (2)	0.3963 (2)	0.46898 (12)	0.0107 (4)
C20	0.0565 (2)	0.6734 (2)	0.43629 (12)	0.0114 (4)
C21	0.4003 (2)	0.2998 (2)	0.40786 (12)	0.0106 (4)
C22	0.2451 (2)	−0.0043 (2)	0.45983 (13)	0.0125 (4)
O1W	0.55695 (16)	0.00217 (15)	0.28937 (9)	0.0130 (3)
H1	0.6477	0.0287	0.2913	0.020*
H2	0.5227	−0.0755	0.2593	0.020*
O2W	−0.15742 (16)	0.07809 (17)	0.30343 (9)	0.0166 (3)
H3	−0.1151	0.1488	0.2859	0.025*
H4	−0.1159	0.0052	0.2830	0.025*
O3W	−0.09191 (17)	−0.20352 (17)	0.24040 (9)	0.0180 (3)
H5	−0.0481	−0.2423	0.2819	0.027*
H6	−0.1443	−0.2697	0.2077	0.027*

	U11	U22	U33	U12	U13	U23
Zn1	0.01283 (12)	0.01187 (11)	0.00817 (11)	0.00039 (9)	0.00278 (8)	0.00002 (8)
Zn2	0.01472 (12)	0.01176 (11)	0.00832 (11)	0.00042 (9)	0.00333 (9)	0.00050 (8)
N1	0.0103 (8)	0.0110 (8)	0.0105 (8)	0.0004 (6)	0.0018 (6)	0.0002 (6)
N2	0.0132 (8)	0.0094 (7)	0.0110 (8)	−0.0014 (6)	0.0041 (6)	0.0017 (6)
N3	0.0107 (8)	0.0092 (7)	0.0098 (8)	−0.0002 (6)	0.0029 (6)	−0.0007 (6)
N4	0.0170 (9)	0.0171 (9)	0.0126 (8)	0.0048 (7)	0.0011 (7)	0.0004 (7)
N5	0.0209 (9)	0.0180 (9)	0.0080 (8)	0.0026 (7)	0.0023 (7)	0.0011 (6)
N6	0.0148 (8)	0.0211 (9)	0.0095 (8)	0.0057 (7)	0.0033 (6)	0.0023 (7)
O1	0.0154 (7)	0.0155 (7)	0.0095 (7)	−0.0029 (6)	0.0019 (5)	−0.0003 (5)
O2	0.0243 (9)	0.0271 (9)	0.0127 (7)	−0.0133 (7)	0.0042 (6)	0.0033 (6)
O3	0.0164 (7)	0.0181 (7)	0.0085 (7)	−0.0015 (6)	0.0024 (5)	−0.0003 (5)
O4	0.0176 (7)	0.0176 (7)	0.0111 (7)	−0.0068 (6)	0.0056 (6)	0.0004 (6)
O5	0.0154 (7)	0.0182 (7)	0.0081 (7)	−0.0071 (6)	0.0014 (5)	−0.0012 (5)
O6	0.0199 (8)	0.0138 (7)	0.0102 (7)	−0.0022 (6)	0.0049 (6)	0.0000 (5)
O7	0.0232 (8)	0.0137 (7)	0.0148 (7)	−0.0068 (6)	0.0065 (6)	−0.0011 (6)
O8	0.0166 (7)	0.0168 (7)	0.0100 (7)	−0.0036 (6)	0.0050 (6)	0.0004 (5)
O9	0.0170 (7)	0.0162 (7)	0.0138 (7)	−0.0068 (6)	0.0031 (6)	−0.0002 (6)
O10	0.0250 (8)	0.0169 (7)	0.0093 (7)	−0.0083 (6)	0.0050 (6)	0.0002 (6)
O11	0.0155 (7)	0.0145 (7)	0.0111 (7)	0.0023 (6)	0.0035 (5)	0.0018 (5)
O12	0.0151 (7)	0.0136 (7)	0.0162 (7)	0.0032 (6)	0.0059 (6)	0.0002 (6)
O13	0.0159 (7)	0.0131 (7)	0.0101 (7)	0.0018 (6)	0.0043 (5)	−0.0002 (5)
O14	0.0179 (8)	0.0169 (7)	0.0158 (7)	0.0067 (6)	0.0047 (6)	0.0009 (6)
O15	0.0227 (8)	0.0160 (7)	0.0081 (7)	0.0024 (6)	0.0005 (6)	−0.0016 (5)
C1	0.0109 (9)	0.0095 (8)	0.0120 (9)	0.0006 (7)	0.0032 (7)	0.0007 (7)
C2	0.0126 (9)	0.0133 (9)	0.0114 (9)	0.0010 (7)	0.0031 (7)	0.0029 (7)
C3	0.0131 (9)	0.0115 (9)	0.0084 (9)	0.0020 (7)	0.0015 (7)	0.0010 (7)
C4	0.0117 (9)	0.0112 (9)	0.0113 (9)	−0.0028 (7)	0.0012 (7)	0.0012 (7)
C5	0.0110 (9)	0.0122 (9)	0.0110 (9)	0.0000 (7)	0.0036 (7)	0.0014 (7)
C6	0.0136 (9)	0.0135 (9)	0.0110 (9)	−0.0022 (7)	0.0032 (7)	0.0000 (7)
C7	0.0116 (9)	0.0124 (9)	0.0124 (9)	0.0010 (7)	0.0039 (7)	0.0022 (7)
C8	0.0143 (9)	0.0091 (9)	0.0116 (9)	−0.0008 (7)	0.0031 (7)	0.0005 (7)
C9	0.0163 (10)	0.0125 (9)	0.0122 (9)	−0.0027 (8)	0.0033 (8)	0.0017 (7)
C10	0.0160 (10)	0.0124 (9)	0.0101 (9)	0.0010 (8)	0.0032 (7)	0.0014 (7)
C11	0.0145 (9)	0.0121 (9)	0.0113 (9)	−0.0012 (7)	0.0016 (7)	0.0010 (7)
C12	0.0110 (9)	0.0091 (8)	0.0123 (9)	−0.0012 (7)	0.0017 (7)	0.0005 (7)
C13	0.0156 (10)	0.0090 (8)	0.0125 (9)	−0.0011 (7)	0.0024 (7)	0.0003 (7)
C14	0.0105 (9)	0.0129 (9)	0.0122 (9)	0.0000 (7)	0.0018 (7)	0.0027 (7)
C15	0.0112 (9)	0.0089 (8)	0.0127 (9)	−0.0016 (7)	0.0035 (7)	−0.0002 (7)
C16	0.0136 (9)	0.0120 (9)	0.0111 (9)	−0.0016 (7)	0.0041 (7)	−0.0016 (7)
C17	0.0122 (9)	0.0125 (9)	0.0116 (9)	−0.0033 (7)	0.0024 (7)	−0.0006 (7)
C18	0.0121 (9)	0.0109 (9)	0.0115 (9)	−0.0014 (7)	0.0013 (7)	0.0003 (7)
C19	0.0116 (9)	0.0094 (8)	0.0112 (9)	−0.0014 (7)	0.0036 (7)	−0.0002 (7)
C20	0.0110 (9)	0.0101 (9)	0.0136 (9)	−0.0025 (7)	0.0032 (7)	0.0024 (7)
C21	0.0095 (9)	0.0106 (9)	0.0121 (9)	−0.0022 (7)	0.0044 (7)	0.0001 (7)
C22	0.0124 (9)	0.0128 (9)	0.0125 (9)	−0.0026 (7)	0.0029 (7)	0.0018 (7)
O1W	0.0127 (7)	0.0121 (7)	0.0132 (7)	−0.0014 (5)	0.0010 (5)	−0.0009 (5)
O2W	0.0159 (7)	0.0188 (8)	0.0158 (7)	−0.0018 (6)	0.0040 (6)	0.0032 (6)
O3W	0.0200 (8)	0.0199 (8)	0.0151 (7)	0.0022 (6)	0.0030 (6)	0.0069 (6)

Zn1—O13	1.9541 (14)	O10—H10A	0.8400
Zn1—O1W	1.9599 (14)	O11—C20	1.284 (2)
Zn1—N1	2.0157 (17)	O12—C20	1.231 (2)
Zn1—O1	2.0955 (14)	O13—C21	1.296 (2)
Zn1—O3	2.4440 (15)	O14—C21	1.232 (2)
Zn2—N2	1.9965 (17)	O15—C17	1.339 (2)
Zn2—N3	2.0143 (17)	O15—H15	0.8400
Zn2—O11	2.0715 (14)	C1—C2	1.382 (3)
Zn2—O8	2.2311 (15)	C1—C6	1.522 (3)
Zn2—O6	2.2320 (15)	C2—C3	1.393 (3)
Zn2—O13	2.3857 (14)	C2—H2A	0.9500
N1—C5	1.334 (3)	C3—C4	1.409 (3)
N1—C1	1.340 (3)	C4—C5	1.383 (3)
N2—C8	1.337 (3)	C4—H4D	0.9500
N2—C12	1.344 (2)	C5—C7	1.497 (3)
N3—C19	1.337 (3)	C8—C9	1.377 (3)
N3—C15	1.346 (2)	C8—C13	1.524 (3)
N4—C22	1.325 (3)	C9—C10	1.401 (3)
N4—H4A	0.8800	C9—H9A	0.9500
N4—H4B	0.8800	C10—C11	1.399 (3)
N5—C22	1.328 (3)	C11—C12	1.383 (3)
N5—H5A	0.8800	C11—H11A	0.9500
N5—H5B	0.8800	C12—C14	1.515 (3)
N6—C22	1.327 (3)	C15—C16	1.385 (3)
N6—H6A	0.8800	C15—C20	1.525 (3)
N6—H6B	0.8800	C16—C17	1.399 (3)
O1—C6	1.273 (2)	C16—H16A	0.9500
O2—C6	1.233 (2)	C17—C18	1.405 (3)
O3—C7	1.229 (2)	C18—C19	1.377 (3)
O4—C7	1.307 (2)	C18—H18A	0.9500
O4—H4C	0.8400	C19—C21	1.507 (3)
O5—C3	1.331 (2)	O1W—H1	0.8500
O5—H5C	0.8400	O1W—H2	0.8500
O6—C13	1.265 (2)	O2W—H3	0.8501
O7—C13	1.251 (2)	O2W—H4	0.8499
O8—C14	1.264 (2)	O3W—H5	0.8499
O9—C14	1.243 (2)	O3W—H6	0.8500
O10—C10	1.340 (2)
O13—Zn1—O1W	129.21 (6)	C2—C3—C4	119.01 (18)
O13—Zn1—N1	123.11 (6)	C5—C4—C3	117.96 (18)
O1W—Zn1—N1	105.76 (6)	C5—C4—H4D	121.0
O13—Zn1—O1	101.14 (6)	C3—C4—H4D	121.0
O1W—Zn1—O1	100.48 (6)	N1—C5—C4	122.62 (18)
N1—Zn1—O1	79.40 (6)	N1—C5—C7	113.35 (17)
O13—Zn1—O3	93.10 (6)	C4—C5—C7	124.03 (18)
O1W—Zn1—O3	89.12 (6)	O2—C6—O1	126.81 (19)
N1—Zn1—O3	72.01 (6)	O2—C6—C1	117.40 (18)
O1—Zn1—O3	151.36 (5)	O1—C6—C1	115.79 (17)
N2—Zn2—N3	162.44 (7)	O3—C7—O4	125.56 (18)
N2—Zn2—O11	118.12 (6)	O3—C7—C5	119.99 (18)
N3—Zn2—O11	78.99 (6)	O4—C7—C5	114.45 (17)
N2—Zn2—O8	76.65 (6)	N2—C8—C9	122.00 (18)
N3—Zn2—O8	106.40 (6)	N2—C8—C13	113.48 (17)
O11—Zn2—O8	97.59 (6)	C9—C8—C13	124.49 (18)
N2—Zn2—O6	75.85 (6)	C8—C9—C10	119.03 (19)
N3—Zn2—O6	101.32 (6)	C8—C9—H9A	120.5
O11—Zn2—O6	90.99 (6)	C10—C9—H9A	120.5
O8—Zn2—O6	152.06 (5)	O10—C10—C11	117.85 (18)
N2—Zn2—O13	90.61 (6)	O10—C10—C9	123.52 (18)
N3—Zn2—O13	72.57 (6)	C11—C10—C9	118.63 (18)
O11—Zn2—O13	151.16 (5)	C12—C11—C10	118.62 (18)
O8—Zn2—O13	86.07 (5)	C12—C11—H11A	120.7
O6—Zn2—O13	99.08 (5)	C10—C11—H11A	120.7
C5—N1—C1	119.59 (17)	N2—C12—C11	122.00 (18)
C5—N1—Zn1	124.22 (13)	N2—C12—C14	113.65 (17)
C1—N1—Zn1	115.71 (13)	C11—C12—C14	124.34 (17)
C8—N2—C12	119.71 (17)	O7—C13—O6	127.34 (19)
C8—N2—Zn2	120.75 (13)	O7—C13—C8	116.96 (18)
C12—N2—Zn2	119.54 (13)	O6—C13—C8	115.64 (17)
C19—N3—C15	118.98 (17)	O9—C14—O8	126.80 (19)
C19—N3—Zn2	124.50 (13)	O9—C14—C12	116.56 (18)
C15—N3—Zn2	116.52 (13)	O8—C14—C12	116.62 (17)
C22—N4—H4A	120.0	N3—C15—C16	122.62 (19)
C22—N4—H4B	120.0	N3—C15—C20	113.29 (17)
H4A—N4—H4B	120.0	C16—C15—C20	124.07 (18)
C22—N5—H5A	120.0	C15—C16—C17	118.16 (18)
C22—N5—H5B	120.0	C15—C16—H16A	120.9
H5A—N5—H5B	120.0	C17—C16—H16A	120.9
C22—N6—H6A	120.0	O15—C17—C16	124.33 (18)
C22—N6—H6B	120.0	O15—C17—C18	116.65 (18)
H6A—N6—H6B	120.0	C16—C17—C18	119.00 (18)
C6—O1—Zn1	114.71 (12)	C19—C18—C17	118.50 (19)
C7—O3—Zn1	109.54 (13)	C19—C18—H18A	120.7
C7—O4—H4C	109.5	C17—C18—H18A	120.8
C3—O5—H5C	109.5	N3—C19—C18	122.71 (18)
C13—O6—Zn2	114.20 (12)	N3—C19—C21	114.77 (17)
C14—O8—Zn2	112.58 (12)	C18—C19—C21	122.52 (18)
C10—O10—H10A	109.5	O12—C20—O11	125.77 (19)
C20—O11—Zn2	116.08 (13)	O12—C20—C15	119.31 (18)
C21—O13—Zn1	110.63 (12)	O11—C20—C15	114.91 (17)
C21—O13—Zn2	112.70 (12)	O14—C21—O13	123.87 (18)
Zn1—O13—Zn2	136.65 (7)	O14—C21—C19	120.94 (18)
C17—O15—H15	109.5	O13—C21—C19	115.19 (17)
N1—C1—C2	122.10 (18)	N4—C22—N6	120.63 (19)
N1—C1—C6	114.11 (17)	N4—C22—N5	120.05 (19)
C2—C1—C6	123.76 (18)	N6—C22—N5	119.30 (19)
C1—C2—C3	118.71 (18)	Zn1—O1W—H1	107.7
C1—C2—H2A	120.6	Zn1—O1W—H2	110.3
C3—C2—H2A	120.6	H1—O1W—H2	118.8
O5—C3—C2	118.70 (18)	H3—O2W—H4	103.0
O5—C3—C4	122.27 (18)	H5—O3W—H6	107.7
O13—Zn1—N1—C5	−89.84 (17)	C2—C3—C4—C5	−0.4 (3)
O1W—Zn1—N1—C5	75.66 (17)	C1—N1—C5—C4	−0.5 (3)
O1—Zn1—N1—C5	173.68 (17)	Zn1—N1—C5—C4	−172.25 (15)
O3—Zn1—N1—C5	−8.11 (15)	C1—N1—C5—C7	179.16 (17)
O13—Zn1—N1—C1	98.09 (15)	Zn1—N1—C5—C7	7.4 (2)
O1W—Zn1—N1—C1	−96.40 (14)	C3—C4—C5—N1	0.0 (3)
O1—Zn1—N1—C1	1.62 (14)	C3—C4—C5—C7	−179.55 (18)
O3—Zn1—N1—C1	179.83 (15)	Zn1—O1—C6—O2	175.64 (18)
N3—Zn2—N2—C8	−80.4 (3)	Zn1—O1—C6—C1	−4.7 (2)
O11—Zn2—N2—C8	85.88 (16)	N1—C1—C6—O2	−174.20 (18)
O8—Zn2—N2—C8	177.43 (16)	C2—C1—C6—O2	7.8 (3)
O6—Zn2—N2—C8	2.45 (15)	N1—C1—C6—O1	6.1 (3)
O13—Zn2—N2—C8	−96.76 (15)	C2—C1—C6—O1	−171.92 (19)
N3—Zn2—N2—C12	98.9 (3)	Zn1—O3—C7—O4	172.31 (16)
O11—Zn2—N2—C12	−94.91 (15)	Zn1—O3—C7—C5	−7.0 (2)
O8—Zn2—N2—C12	−3.36 (14)	N1—C5—C7—O3	1.3 (3)
O6—Zn2—N2—C12	−178.34 (16)	C4—C5—C7—O3	−179.03 (19)
O13—Zn2—N2—C12	82.45 (15)	N1—C5—C7—O4	−178.08 (17)
N2—Zn2—N3—C19	−15.1 (3)	C4—C5—C7—O4	1.5 (3)
O11—Zn2—N3—C19	177.21 (16)	C12—N2—C8—C9	0.3 (3)
O8—Zn2—N3—C19	82.45 (16)	Zn2—N2—C8—C9	179.54 (15)
O6—Zn2—N3—C19	−93.99 (16)	C12—N2—C8—C13	178.52 (17)
O13—Zn2—N3—C19	2.08 (15)	Zn2—N2—C8—C13	−2.3 (2)
N2—Zn2—N3—C15	164.06 (19)	N2—C8—C9—C10	0.2 (3)
O11—Zn2—N3—C15	−3.60 (14)	C13—C8—C9—C10	−177.83 (19)
O8—Zn2—N3—C15	−98.36 (14)	C8—C9—C10—O10	179.67 (19)
O6—Zn2—N3—C15	85.20 (14)	C8—C9—C10—C11	−0.7 (3)
O13—Zn2—N3—C15	−178.73 (15)	O10—C10—C11—C12	−179.61 (18)
O13—Zn1—O1—C6	−120.04 (14)	C9—C10—C11—C12	0.7 (3)
O1W—Zn1—O1—C6	106.20 (14)	C8—N2—C12—C11	−0.3 (3)
N1—Zn1—O1—C6	1.94 (14)	Zn2—N2—C12—C11	−179.50 (15)
O3—Zn1—O1—C6	−1.6 (2)	C8—N2—C12—C14	178.22 (17)
O13—Zn1—O3—C7	131.73 (14)	Zn2—N2—C12—C14	−1.0 (2)
O1W—Zn1—O3—C7	−99.05 (14)	C10—C11—C12—N2	−0.2 (3)
N1—Zn1—O3—C7	7.85 (13)	C10—C11—C12—C14	−178.59 (18)
O1—Zn1—O3—C7	11.5 (2)	Zn2—O6—C13—O7	178.91 (18)
N2—Zn2—O6—C13	−2.32 (14)	Zn2—O6—C13—C8	1.9 (2)
N3—Zn2—O6—C13	159.91 (14)	N2—C8—C13—O7	−177.34 (18)
O11—Zn2—O6—C13	−121.12 (14)	C9—C8—C13—O7	0.8 (3)
O8—Zn2—O6—C13	−12.8 (2)	N2—C8—C13—O6	0.0 (3)
O13—Zn2—O6—C13	86.01 (14)	C9—C8—C13—O6	178.2 (2)
N2—Zn2—O8—C14	8.08 (14)	Zn2—O8—C14—O9	167.49 (17)
N3—Zn2—O8—C14	−154.02 (14)	Zn2—O8—C14—C12	−11.0 (2)
O11—Zn2—O8—C14	125.28 (14)	N2—C12—C14—O9	−170.05 (18)
O6—Zn2—O8—C14	18.5 (2)	C11—C12—C14—O9	8.4 (3)
O13—Zn2—O8—C14	−83.49 (14)	N2—C12—C14—O8	8.6 (3)
N2—Zn2—O11—C20	−171.55 (13)	C11—C12—C14—O8	−172.96 (19)
N3—Zn2—O11—C20	4.25 (14)	C19—N3—C15—C16	−0.1 (3)
O8—Zn2—O11—C20	109.57 (14)	Zn2—N3—C15—C16	−179.36 (15)
O6—Zn2—O11—C20	−97.09 (14)	C19—N3—C15—C20	−178.17 (17)
O13—Zn2—O11—C20	13.9 (2)	Zn2—N3—C15—C20	2.6 (2)
O1W—Zn1—O13—C21	7.05 (16)	N3—C15—C16—C17	−1.7 (3)
N1—Zn1—O13—C21	168.94 (12)	C20—C15—C16—C17	176.16 (18)
O1—Zn1—O13—C21	−106.53 (13)	C15—C16—C17—O15	−176.19 (18)
O3—Zn1—O13—C21	98.44 (13)	C15—C16—C17—C18	2.1 (3)
O1W—Zn1—O13—Zn2	−171.49 (8)	O15—C17—C18—C19	177.56 (18)
N1—Zn1—O13—Zn2	−9.60 (14)	C16—C17—C18—C19	−0.9 (3)
O1—Zn1—O13—Zn2	74.93 (11)	C15—N3—C19—C18	1.5 (3)
O3—Zn1—O13—Zn2	−80.10 (10)	Zn2—N3—C19—C18	−179.35 (14)
N2—Zn2—O13—C21	170.56 (13)	C15—N3—C19—C21	−179.06 (17)
N3—Zn2—O13—C21	−4.31 (13)	Zn2—N3—C19—C21	0.1 (2)
O11—Zn2—O13—C21	−14.27 (19)	C17—C18—C19—N3	−0.9 (3)
O8—Zn2—O13—C21	−112.87 (13)	C17—C18—C19—C21	179.63 (17)
O6—Zn2—O13—C21	94.79 (13)	Zn2—O11—C20—O12	177.04 (16)
N2—Zn2—O13—Zn1	−10.92 (11)	Zn2—O11—C20—C15	−4.1 (2)
N3—Zn2—O13—Zn1	174.20 (12)	N3—C15—C20—O12	−179.99 (18)
O11—Zn2—O13—Zn1	164.25 (9)	C16—C15—C20—O12	2.0 (3)
O8—Zn2—O13—Zn1	65.65 (10)	N3—C15—C20—O11	1.0 (2)
O6—Zn2—O13—Zn1	−86.69 (11)	C16—C15—C20—O11	−176.98 (18)
C5—N1—C1—C2	1.2 (3)	Zn1—O13—C21—O14	7.2 (2)
Zn1—N1—C1—C2	173.70 (15)	Zn2—O13—C21—O14	−173.85 (16)
C5—N1—C1—C6	−176.84 (17)	Zn1—O13—C21—C19	−173.27 (12)
Zn1—N1—C1—C6	−4.4 (2)	Zn2—O13—C21—C19	5.6 (2)
N1—C1—C2—C3	−1.5 (3)	N3—C19—C21—O14	175.23 (18)
C6—C1—C2—C3	176.35 (18)	C18—C19—C21—O14	−5.3 (3)
C1—C2—C3—O5	−177.33 (18)	N3—C19—C21—O13	−4.3 (2)
C1—C2—C3—C4	1.1 (3)	C18—C19—C21—O13	175.18 (18)
O5—C3—C4—C5	177.99 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O6i	0.88	2.17	2.894 (2)	139
N4—H4B···O14ii	0.88	1.95	2.810 (2)	164
N5—H5A···O1Wii	0.88	2.29	3.074 (2)	149
N5—H5B···O12iii	0.88	2.18	2.949 (2)	146
N6—H6A···O3	0.88	2.08	2.901 (2)	156
N6—H6B···O12iii	0.88	2.09	2.882 (2)	150
O4—H4C···O3W	0.84	1.76	2.586 (2)	170
O5—H5C···O9iv	0.84	1.78	2.596 (2)	163
O10—H10A···O2v	0.84	1.78	2.615 (2)	171
O15—H15···O1vi	0.84	1.87	2.637 (2)	152
O1W—H1···O2Wvii	0.85	1.79	2.642 (2)	175
O1W—H2···O7i	0.85	1.76	2.609 (2)	178
O2W—H3···O8	0.85	2.07	2.912 (2)	171
O2W—H4···O3W	0.85	2.02	2.827 (2)	158
O3W—H5···O11i	0.85	1.78	2.622 (2)	170
O3W—H6···O10iv	0.85	2.59	3.344 (2)	148
C4—H4D···O9iv	0.95	2.30	2.993 (2)	129
C9—H9A···O2v	0.95	2.37	3.046 (3)	128

Zn1—O13	1.9541 (14)
Zn1—O1W	1.9599 (14)
Zn1—N1	2.0157 (17)
Zn1—O1	2.0955 (14)
Zn1—O3	2.4440 (15)
Zn2—N2	1.9965 (17)
Zn2—N3	2.0143 (17)
Zn2—O11	2.0715 (14)
Zn2—O8	2.2311 (15)
Zn2—O6	2.2320 (15)
Zn2—O13	2.3857 (14)

O13—Zn1—O1	101.14 (6)
O1—Zn1—O3	151.36 (5)
N2—Zn2—N3	162.44 (7)
O11—Zn2—O6	90.99 (6)
O8—Zn2—O6	152.06 (5)
O11—Zn2—O13	151.16 (5)
O8—Zn2—O13	86.07 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O6i	0.88	2.17	2.894 (2)	139
N4—H4B⋯O14ii	0.88	1.95	2.810 (2)	164
N5—H5A⋯O1Wii	0.88	2.29	3.074 (2)	149
N5—H5B⋯O12iii	0.88	2.18	2.949 (2)	146
N6—H6A⋯O3	0.88	2.08	2.901 (2)	156
N6—H6B⋯O12iii	0.88	2.09	2.882 (2)	150
O4—H4C⋯O3W	0.84	1.75	2.586 (2)	170
O5—H5C⋯O9iv	0.84	1.78	2.596 (2)	163
O10—H10A⋯O2v	0.84	1.78	2.615 (2)	171
O15—H15⋯O1vi	0.84	1.87	2.637 (2)	152
O1W—H1⋯O2Wvii	0.85	1.79	2.642 (2)	175
O1W—H2⋯O7i	0.85	1.76	2.609 (2)	178
O2W—H3⋯O8	0.85	2.07	2.912 (2)	171
O2W—H4⋯O3W	0.85	2.02	2.827 (2)	158
O3W—H5⋯O11i	0.85	1.78	2.622 (2)	170
O3W—H6⋯O10iv	0.85	2.59	3.344 (2)	148
C4—H4D⋯O9iv	0.95	2.30	2.993 (2)	129
C9—H9A⋯O2v	0.95	2.37	3.046 (3)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .