catena-Poly[[[aqua-(4,4'-dimethyl-2,2'-bipyridine-κ(2)N,N')zinc]-μ-3-chloro-benzene-1,2-dicaboxylato-κ(2)O(2):O(3)] [[(4,4'-dimethyl-2,2'-bipyridine-κ(2)N,N')zinc]-μ-3-chloro-benzene-1,2-dicaboxylato-κ(2)O(2):O(3)]].

In the title compound, {[Zn(C(8)H(3)ClO(4))(C(12)H(12)N(2))(H(2)O)]·[Zn(C(8)H(3)ClO(4))(C(12)H(12)N(2))]}(n), one Zn(2+) ion is five-coordin-ated by two O atoms from two different 3-chloro-benzene-1,2-dicarboxyl-ate ligands, one O atom from a water mol-ecule and two N atoms from a 4,4'-dimethyl-2,2'-bipyridine ligand, while the second Zn(2+) ion is four-coordinated by two O atoms from two different 3-chloro-benzene-1,2-dicarboxyl-ate ligands, and two N atoms from a 4,4'-bimethyl-2,2'-bipyridine ligand. The crystal structure exhibits a three-dimensional supra-molecular structure composed of alternate Zn(C(8)H(3)O(4)Cl)(C(12)H(12)N(2)) and Zn(C(8)H(3)O(4)Cl)(C(12)H(12)N(2))(H(2)O) chains, which are linked together by face-to-face π-π inter-actions [shortest centroid-centroid distances of 3.661 (4) and 3.6901 (3) Å], O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ▶); Ockwig et al. (2005 ▶); Zang et al. (2011 ▶). For related O—H⋯O hydrogen bonds, see: Desiraju et al. (2004 ▶). For related π–π inter­actions, see: Zang et al. (2010 ▶). For related C—H⋯O hydrogen bonds, see: Desiraju et al. (1996 ▶). For related C—H⋯π inter­actions, see: Nishio et al. (1998 ▶).

Experimental

Crystal data

[Zn(C8H3ClO4)(C12H12N2)(H2O)]·[Zn(C8H3ClO4)(C12H12N2)]

M = 914.38

Orthorhombic,

a = 34.050 (4) Å

b = 14.1831 (10) Å

c = 7.8764 (6) Å

V = 3803.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.47 mm−1

T = 291 K

0.20 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.971, T max = 1.000

10533 measured reflections

6396 independent reflections

5076 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.104

S = 1.07

6396 reflections

518 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 2200 Friedel pairs

Flack parameter: 0.093 (14)

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014006/zq2156sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014006/zq2156Isup2.hkl

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

[Zn(C8H3ClO4)(C12H12N2)(H2O)]·[Zn(C8H3ClO4)(C12H12N2)]	Dx = 1.597 Mg m−3
Mr = 914.38	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pna21	Cell parameters from 1842 reflections
a = 34.050 (4) Å	θ = 2.9–29.3°
b = 14.1831 (10) Å	µ = 1.47 mm−1
c = 7.8764 (6) Å	T = 291 K
V = 3803.8 (6) Å3	Prismatic, colourless
Z = 4	0.20 × 0.18 × 0.16 mm
F(000) = 1864

Oxford Diffraction Xcalibur Eos Gemini diffractometer	6396 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 16.2312 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −18→42
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −17→17
Tmin = 0.971, Tmax = 1.000	l = −7→9
10533 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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
6396 reflections	Δρmax = 0.63 e Å−3
518 parameters	Δρmin = −0.37 e Å−3
1 restraint	Absolute structure: Flack (1983), 2200 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.093 (14)

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	0.446526 (19)	0.36444 (4)	0.62772 (9)	0.02863 (16)
Zn2	0.73030 (2)	0.67276 (5)	0.37248 (10)	0.03441 (18)
Cl1	0.53270 (7)	0.15962 (15)	−0.2478 (2)	0.0655 (6)
Cl2	0.84880 (6)	0.65033 (13)	1.2682 (2)	0.0487 (5)
O1	0.48307 (15)	0.3004 (3)	0.4755 (5)	0.0462 (13)
O1W	0.47741 (14)	0.4839 (3)	0.7036 (6)	0.0493 (13)
H1WA	0.4918	0.5028	0.6220	0.074*
H1WB	0.4881	0.4524	0.7830	0.074*
O2	0.45488 (16)	0.3521 (3)	0.2380 (6)	0.0524 (14)
O3	0.46114 (11)	0.2980 (3)	−0.1501 (5)	0.0289 (9)
O4	0.51092 (14)	0.3849 (3)	−0.0516 (5)	0.0450 (12)
O5	0.77114 (14)	0.6635 (4)	0.5400 (6)	0.0487 (13)
O6	0.73636 (14)	0.6683 (4)	0.7724 (6)	0.0651 (17)
O7	0.75751 (13)	0.7136 (3)	1.1661 (5)	0.0400 (11)
O8	0.76227 (13)	0.5605 (3)	1.1177 (7)	0.0553 (13)
N1	0.39925 (14)	0.4462 (3)	0.5397 (6)	0.0282 (12)
N2	0.39966 (14)	0.2639 (3)	0.6065 (7)	0.0315 (12)
N3	0.68490 (14)	0.5810 (3)	0.3955 (6)	0.0335 (12)
N4	0.68816 (15)	0.7651 (3)	0.4601 (6)	0.0329 (13)
C1	0.47656 (19)	0.2992 (5)	0.3164 (7)	0.0305 (15)
C1A	0.49032 (19)	0.3121 (4)	−0.0579 (7)	0.0266 (14)
C2	0.5919 (2)	0.9246 (5)	0.6602 (12)	0.072 (3)
H2A	0.5960	0.9384	0.7781	0.107*
H2B	0.5682	0.8888	0.6473	0.107*
H2C	0.5898	0.9824	0.5975	0.107*
C3	0.49776 (19)	0.2223 (4)	0.2198 (7)	0.0264 (14)
C4	0.50368 (18)	0.2278 (4)	0.0461 (7)	0.0263 (14)
C5	0.5226 (2)	0.1537 (4)	−0.0331 (9)	0.0388 (18)
C6	0.5346 (2)	0.0737 (5)	0.0544 (9)	0.0463 (19)
H6	0.5470	0.0246	−0.0028	0.056*
C7	0.5282 (2)	0.0680 (5)	0.2251 (9)	0.0447 (19)
H7	0.5356	0.0143	0.2846	0.054*
C8	0.5105 (2)	0.1420 (4)	0.3089 (8)	0.0404 (18)
H8	0.5071	0.1388	0.4258	0.049*
C9	0.7673 (2)	0.6666 (5)	0.7003 (9)	0.0356 (17)
C10	0.77225 (18)	0.6434 (4)	1.0906 (7)	0.0325 (15)
C11	0.80563 (19)	0.6689 (4)	0.7983 (7)	0.0292 (15)
C12	0.80732 (19)	0.6604 (4)	0.9751 (7)	0.0251 (14)
C13	0.8441 (2)	0.6620 (4)	1.0484 (8)	0.0308 (15)
C14	0.8786 (2)	0.6732 (4)	0.9570 (9)	0.0384 (17)
H14	0.9028	0.6751	1.0115	0.046*
C15	0.8759 (2)	0.6812 (5)	0.7839 (10)	0.0473 (19)
H15	0.8986	0.6874	0.7192	0.057*
C16	0.8403 (2)	0.6802 (4)	0.7065 (7)	0.0354 (16)
H16	0.8390	0.6873	0.5892	0.043*
C17	0.4015 (2)	0.5397 (4)	0.5072 (9)	0.0426 (17)
H17	0.4248	0.5717	0.5298	0.051*
C18	0.3702 (2)	0.5882 (4)	0.4417 (9)	0.0448 (18)
H18	0.3724	0.6526	0.4209	0.054*
C19	0.3356 (2)	0.5428 (4)	0.4066 (8)	0.0404 (17)
C20	0.33365 (19)	0.4466 (4)	0.4388 (8)	0.0378 (16)
H20	0.3105	0.4136	0.4181	0.045*
C21	0.36621 (18)	0.4002 (4)	0.5020 (7)	0.0281 (14)
C22	0.36610 (18)	0.2978 (4)	0.5409 (7)	0.0285 (14)
C23	0.33407 (19)	0.2400 (4)	0.5094 (8)	0.0371 (16)
H23	0.3112	0.2650	0.4631	0.045*
C24	0.3363 (2)	0.1447 (4)	0.5475 (9)	0.0441 (18)
C25	0.3715 (2)	0.1119 (4)	0.6178 (11)	0.0478 (18)
H25	0.3743	0.0485	0.6453	0.057*
C26	0.4011 (2)	0.1728 (4)	0.6454 (9)	0.0471 (18)
H26	0.4240	0.1497	0.6947	0.057*
C27	0.3001 (2)	0.5942 (5)	0.3372 (12)	0.074 (3)
H27A	0.2881	0.6302	0.4263	0.111*
H27B	0.2816	0.5492	0.2937	0.111*
H27C	0.3082	0.6357	0.2475	0.111*
C28	0.3008 (2)	0.0812 (5)	0.5202 (10)	0.064 (2)
H28A	0.2998	0.0345	0.6084	0.096*
H28B	0.3029	0.0506	0.4119	0.096*
H28C	0.2772	0.1184	0.5233	0.096*
C29	0.6922 (2)	0.8562 (5)	0.4932 (10)	0.0499 (19)
H29	0.7161	0.8853	0.4702	0.060*
C30	0.6618 (2)	0.9098 (4)	0.5612 (9)	0.049 (2)
H30	0.6656	0.9734	0.5847	0.059*
C31	0.62615 (19)	0.8681 (4)	0.5935 (9)	0.0410 (18)
C32	0.62257 (19)	0.7715 (4)	0.5612 (8)	0.0356 (16)
H32	0.5989	0.7408	0.5827	0.043*
C33	0.65364 (19)	0.7224 (4)	0.4983 (7)	0.0290 (14)
C34	0.65222 (19)	0.6193 (4)	0.4647 (7)	0.0296 (15)
C35	0.61938 (19)	0.5652 (4)	0.5012 (7)	0.0351 (16)
H35	0.5973	0.5938	0.5480	0.042*
C36	0.6189 (2)	0.4691 (4)	0.4691 (8)	0.0384 (17)
C37	0.6532 (2)	0.4317 (4)	0.3981 (10)	0.0473 (19)
H37	0.6547	0.3676	0.3745	0.057*
C38	0.6845 (2)	0.4887 (4)	0.3632 (10)	0.0460 (17)
H38	0.7067	0.4617	0.3144	0.055*
C39	0.5834 (2)	0.4107 (5)	0.5081 (10)	0.059 (2)
H39A	0.5900	0.3642	0.5920	0.088*
H39B	0.5746	0.3799	0.4066	0.088*
H39C	0.5629	0.4506	0.5509	0.088*

	U11	U22	U33	U12	U13	U23
Zn1	0.0277 (4)	0.0328 (3)	0.0254 (3)	0.0020 (3)	0.0000 (4)	0.0016 (3)
Zn2	0.0264 (4)	0.0442 (4)	0.0327 (4)	0.0009 (3)	0.0010 (4)	−0.0032 (4)
Cl1	0.0765 (16)	0.0915 (15)	0.0283 (10)	0.0279 (13)	0.0089 (10)	−0.0091 (10)
Cl2	0.0505 (13)	0.0658 (12)	0.0297 (9)	0.0041 (10)	−0.0054 (8)	−0.0054 (8)
O1	0.053 (3)	0.070 (3)	0.016 (2)	0.021 (3)	0.002 (2)	−0.005 (2)
O1W	0.060 (4)	0.040 (3)	0.048 (3)	−0.014 (2)	−0.011 (2)	0.015 (2)
O2	0.071 (4)	0.056 (3)	0.031 (3)	0.027 (3)	−0.005 (3)	−0.011 (2)
O3	0.029 (2)	0.038 (2)	0.020 (2)	−0.0047 (18)	−0.0028 (19)	0.0053 (19)
O4	0.048 (3)	0.044 (3)	0.043 (3)	−0.015 (2)	−0.017 (2)	0.007 (2)
O5	0.034 (3)	0.081 (4)	0.030 (3)	0.004 (3)	−0.003 (2)	−0.001 (2)
O6	0.025 (3)	0.127 (5)	0.043 (3)	−0.006 (3)	0.003 (3)	0.007 (3)
O7	0.041 (3)	0.048 (3)	0.032 (3)	0.008 (2)	0.004 (2)	−0.010 (2)
O8	0.048 (3)	0.041 (3)	0.077 (3)	−0.002 (2)	0.018 (3)	0.015 (3)
N1	0.024 (3)	0.027 (3)	0.033 (3)	0.001 (2)	0.008 (2)	0.000 (2)
N2	0.032 (3)	0.029 (3)	0.033 (3)	−0.001 (2)	−0.006 (3)	0.001 (2)
N3	0.031 (3)	0.033 (3)	0.037 (3)	0.003 (2)	0.000 (3)	−0.011 (3)
N4	0.024 (3)	0.030 (3)	0.045 (3)	0.001 (2)	0.000 (2)	−0.007 (2)
C1	0.025 (4)	0.039 (4)	0.028 (3)	−0.001 (3)	0.002 (3)	0.000 (3)
C1A	0.028 (4)	0.033 (3)	0.019 (3)	−0.002 (3)	0.002 (3)	−0.004 (3)
C2	0.050 (5)	0.046 (4)	0.120 (8)	−0.003 (4)	0.028 (5)	−0.024 (5)
C3	0.029 (4)	0.032 (3)	0.019 (3)	−0.002 (3)	−0.005 (3)	−0.003 (3)
C4	0.017 (3)	0.032 (3)	0.029 (3)	−0.003 (3)	−0.004 (3)	−0.004 (3)
C5	0.038 (5)	0.037 (4)	0.041 (4)	−0.001 (3)	−0.007 (3)	−0.004 (3)
C6	0.048 (5)	0.037 (4)	0.054 (5)	0.011 (4)	−0.003 (4)	−0.007 (3)
C7	0.057 (5)	0.039 (4)	0.038 (4)	0.013 (4)	−0.015 (4)	0.007 (3)
C8	0.049 (5)	0.044 (4)	0.027 (4)	0.000 (4)	−0.007 (3)	0.004 (3)
C9	0.035 (4)	0.040 (4)	0.033 (4)	0.005 (3)	0.008 (3)	0.002 (3)
C10	0.030 (4)	0.045 (4)	0.022 (4)	−0.003 (3)	−0.004 (3)	−0.003 (3)
C11	0.027 (4)	0.029 (3)	0.031 (3)	0.003 (3)	−0.002 (3)	−0.004 (3)
C12	0.029 (4)	0.023 (3)	0.023 (3)	0.000 (3)	0.000 (3)	−0.006 (2)
C13	0.039 (4)	0.025 (3)	0.028 (3)	0.005 (3)	0.000 (3)	−0.002 (3)
C14	0.034 (4)	0.048 (4)	0.033 (4)	−0.003 (3)	0.001 (3)	−0.005 (3)
C15	0.028 (4)	0.059 (5)	0.055 (5)	0.002 (4)	0.007 (4)	0.000 (4)
C16	0.043 (5)	0.049 (4)	0.014 (3)	−0.002 (3)	−0.001 (3)	−0.002 (3)
C17	0.033 (4)	0.030 (3)	0.064 (5)	0.003 (3)	0.009 (4)	0.004 (3)
C18	0.042 (5)	0.026 (3)	0.066 (5)	0.008 (3)	0.007 (4)	0.001 (3)
C19	0.036 (4)	0.042 (4)	0.043 (4)	0.012 (3)	0.000 (3)	0.000 (3)
C20	0.027 (4)	0.042 (4)	0.044 (4)	0.002 (3)	−0.002 (3)	0.008 (3)
C21	0.022 (3)	0.038 (3)	0.024 (3)	−0.003 (3)	0.002 (3)	−0.005 (3)
C22	0.028 (4)	0.041 (3)	0.017 (3)	0.000 (3)	0.002 (3)	−0.002 (3)
C23	0.026 (4)	0.038 (4)	0.047 (4)	−0.005 (3)	−0.001 (3)	−0.005 (3)
C24	0.051 (5)	0.035 (4)	0.047 (4)	−0.015 (4)	−0.001 (4)	−0.005 (3)
C25	0.064 (5)	0.025 (3)	0.055 (4)	0.002 (3)	−0.006 (5)	0.001 (4)
C26	0.054 (5)	0.039 (3)	0.048 (4)	−0.003 (3)	−0.014 (4)	0.005 (4)
C27	0.053 (5)	0.057 (5)	0.112 (8)	0.018 (4)	−0.018 (6)	0.022 (5)
C28	0.059 (6)	0.048 (4)	0.086 (6)	−0.023 (4)	−0.006 (5)	−0.005 (4)
C29	0.040 (5)	0.046 (4)	0.064 (5)	−0.011 (4)	0.011 (4)	−0.004 (4)
C30	0.043 (4)	0.028 (3)	0.076 (5)	−0.005 (3)	0.003 (4)	−0.011 (3)
C31	0.034 (4)	0.040 (3)	0.050 (5)	0.008 (3)	0.006 (3)	−0.015 (3)
C32	0.028 (4)	0.038 (4)	0.041 (4)	−0.005 (3)	0.001 (3)	−0.004 (3)
C33	0.030 (4)	0.031 (3)	0.026 (3)	0.000 (3)	−0.006 (3)	−0.002 (3)
C34	0.027 (4)	0.034 (3)	0.027 (3)	0.000 (3)	−0.002 (3)	−0.004 (3)
C35	0.025 (4)	0.043 (4)	0.038 (4)	−0.004 (3)	0.000 (3)	0.000 (3)
C36	0.039 (4)	0.031 (3)	0.045 (4)	−0.004 (3)	−0.011 (3)	−0.001 (3)
C37	0.047 (5)	0.029 (3)	0.066 (5)	−0.001 (3)	0.002 (4)	−0.002 (4)
C38	0.034 (4)	0.043 (4)	0.061 (5)	0.007 (3)	−0.001 (4)	−0.012 (4)
C39	0.044 (5)	0.034 (4)	0.098 (6)	0.000 (4)	−0.001 (5)	0.007 (4)

Zn1—O1	1.952 (4)	C12—C13	1.378 (9)
Zn1—O1W	2.082 (4)	C13—C14	1.387 (9)
Zn1—O3i	2.049 (4)	C14—H14	0.9300
Zn1—N1	2.102 (5)	C14—C15	1.371 (8)
Zn1—N2	2.146 (4)	C15—H15	0.9300
Zn2—O5	1.921 (5)	C15—C16	1.357 (9)
Zn2—O7ii	1.958 (4)	C16—H16	0.9300
Zn2—N3	2.029 (5)	C17—H17	0.9300
Zn2—N4	2.062 (5)	C17—C18	1.370 (9)
Cl1—C5	1.729 (7)	C18—H18	0.9300
Cl2—C13	1.747 (6)	C18—C19	1.372 (9)
O1—C1	1.273 (7)	C19—C20	1.389 (8)
O1W—H1WA	0.8512	C19—C27	1.513 (9)
O1W—H1WB	0.8501	C20—H20	0.9300
O2—C1	1.220 (8)	C20—C21	1.382 (8)
O3—Zn1ii	2.049 (4)	C21—C22	1.484 (8)
O3—C1A	1.246 (7)	C22—C23	1.387 (8)
O4—C1A	1.249 (7)	C23—H23	0.9300
O5—C9	1.270 (7)	C23—C24	1.386 (9)
O6—C9	1.196 (8)	C24—C25	1.400 (9)
O7—Zn2i	1.958 (4)	C24—C28	1.523 (9)
O7—C10	1.264 (7)	C25—H25	0.9300
O8—C10	1.242 (7)	C25—C26	1.347 (8)
N1—C17	1.352 (8)	C26—H26	0.9300
N1—C21	1.334 (7)	C27—H27A	0.9600
N2—C22	1.343 (7)	C27—H27B	0.9600
N2—C26	1.329 (7)	C27—H27C	0.9600
N3—C34	1.353 (7)	C28—H28A	0.9600
N3—C38	1.334 (7)	C28—H28B	0.9600
N4—C29	1.325 (8)	C28—H28C	0.9600
N4—C33	1.357 (8)	C29—H29	0.9300
C1—C3	1.514 (8)	C29—C30	1.391 (9)
C1A—C4	1.520 (8)	C30—H30	0.9300
C2—H2A	0.9600	C30—C31	1.374 (9)
C2—H2B	0.9600	C31—C32	1.400 (8)
C2—H2C	0.9600	C32—H32	0.9300
C2—C31	1.507 (8)	C32—C33	1.360 (8)
C3—C4	1.385 (7)	C33—C34	1.487 (8)
C3—C8	1.407 (8)	C34—C35	1.386 (8)
C4—C5	1.381 (9)	C35—H35	0.9300
C5—C6	1.389 (9)	C35—C36	1.386 (8)
C6—H6	0.9300	C36—C37	1.399 (9)
C6—C7	1.365 (9)	C36—C39	1.498 (9)
C7—H7	0.9300	C37—H37	0.9300
C7—C8	1.377 (9)	C37—C38	1.364 (9)
C8—H8	0.9300	C38—H38	0.9300
C9—C11	1.518 (9)	C39—H39A	0.9600
C10—C12	1.521 (9)	C39—H39B	0.9600
C11—C12	1.399 (7)	C39—H39C	0.9600
C11—C16	1.394 (9)
O1—Zn1—O1W	103.5 (2)	C16—C15—C14	120.3 (7)
O1—Zn1—O3i	98.96 (17)	C16—C15—H15	119.9
O1—Zn1—N1	122.84 (18)	C11—C16—H16	119.2
O1—Zn1—N2	96.7 (2)	C15—C16—C11	121.7 (6)
O1W—Zn1—N1	91.85 (18)	C15—C16—H16	119.2
O1W—Zn1—N2	159.80 (19)	N1—C17—H17	119.4
O3i—Zn1—O1W	90.36 (16)	N1—C17—C18	121.3 (6)
O3i—Zn1—N1	136.19 (17)	C18—C17—H17	119.4
O3i—Zn1—N2	86.66 (17)	C17—C18—H18	119.7
N1—Zn1—N2	76.79 (18)	C17—C18—C19	120.6 (6)
O5—Zn2—O7ii	104.35 (19)	C19—C18—H18	119.7
O5—Zn2—N3	116.5 (2)	C18—C19—C20	117.7 (6)
O5—Zn2—N4	108.5 (2)	C18—C19—C27	122.1 (6)
O7ii—Zn2—N3	128.6 (2)	C20—C19—C27	120.1 (6)
O7ii—Zn2—N4	114.78 (19)	C19—C20—H20	120.1
N3—Zn2—N4	81.22 (19)	C21—C20—C19	119.7 (6)
C1—O1—Zn1	120.0 (4)	C21—C20—H20	120.1
Zn1—O1W—H1WA	109.3	N1—C21—C20	121.6 (6)
Zn1—O1W—H1WB	89.9	N1—C21—C22	115.8 (5)
H1WA—O1W—H1WB	118.4	C20—C21—C22	122.6 (6)
C1A—O3—Zn1ii	128.1 (4)	N2—C22—C21	115.3 (5)
C9—O5—Zn2	127.2 (5)	N2—C22—C23	121.8 (5)
C10—O7—Zn2i	110.2 (4)	C23—C22—C21	122.9 (6)
C17—N1—Zn1	124.0 (4)	C22—C23—H23	120.2
C21—N1—Zn1	116.7 (4)	C24—C23—C22	119.7 (6)
C21—N1—C17	119.1 (6)	C24—C23—H23	120.2
C22—N2—Zn1	115.1 (4)	C23—C24—C25	117.1 (6)
C26—N2—Zn1	126.8 (4)	C23—C24—C28	120.2 (7)
C26—N2—C22	118.0 (5)	C25—C24—C28	122.6 (6)
C34—N3—Zn2	113.9 (4)	C24—C25—H25	120.2
C38—N3—Zn2	128.4 (4)	C26—C25—C24	119.6 (6)
C38—N3—C34	117.5 (5)	C26—C25—H25	120.2
C29—N4—Zn2	127.8 (5)	N2—C26—C25	123.9 (6)
C29—N4—C33	118.8 (6)	N2—C26—H26	118.1
C33—N4—Zn2	113.2 (4)	C25—C26—H26	118.1
O1—C1—C3	114.9 (6)	C19—C27—H27A	109.5
O2—C1—O1	126.6 (6)	C19—C27—H27B	109.5
O2—C1—C3	118.5 (5)	C19—C27—H27C	109.5
O3—C1A—O4	127.1 (6)	H27A—C27—H27B	109.5
O3—C1A—C4	115.2 (5)	H27A—C27—H27C	109.5
O4—C1A—C4	117.4 (5)	H27B—C27—H27C	109.5
H2A—C2—H2B	109.5	C24—C28—H28A	109.5
H2A—C2—H2C	109.5	C24—C28—H28B	109.5
H2B—C2—H2C	109.5	C24—C28—H28C	109.5
C31—C2—H2A	109.5	H28A—C28—H28B	109.5
C31—C2—H2B	109.5	H28A—C28—H28C	109.5
C31—C2—H2C	109.5	H28B—C28—H28C	109.5
C4—C3—C1	121.7 (6)	N4—C29—H29	118.9
C4—C3—C8	119.5 (6)	N4—C29—C30	122.1 (6)
C8—C3—C1	118.7 (5)	C30—C29—H29	118.9
C3—C4—C1A	122.2 (6)	C29—C30—H30	120.2
C5—C4—C1A	119.7 (5)	C31—C30—C29	119.6 (6)
C5—C4—C3	118.1 (6)	C31—C30—H30	120.2
C4—C5—Cl1	119.9 (5)	C30—C31—C2	121.3 (6)
C4—C5—C6	122.3 (6)	C30—C31—C32	117.7 (6)
C6—C5—Cl1	117.8 (5)	C32—C31—C2	121.1 (6)
C5—C6—H6	120.3	C31—C32—H32	120.0
C7—C6—C5	119.3 (7)	C33—C32—C31	120.0 (6)
C7—C6—H6	120.3	C33—C32—H32	120.0
C6—C7—H7	120.1	N4—C33—C32	121.7 (5)
C6—C7—C8	119.8 (6)	N4—C33—C34	115.4 (5)
C8—C7—H7	120.1	C32—C33—C34	122.9 (6)
C3—C8—H8	119.6	N3—C34—C33	116.1 (5)
C7—C8—C3	120.9 (6)	N3—C34—C35	121.7 (5)
C7—C8—H8	119.6	C35—C34—C33	122.2 (6)
O5—C9—C11	114.7 (6)	C34—C35—H35	119.5
O6—C9—O5	124.3 (7)	C36—C35—C34	121.0 (6)
O6—C9—C11	121.0 (6)	C36—C35—H35	119.5
O7—C10—C12	117.9 (5)	C35—C36—C37	115.9 (6)
O8—C10—O7	123.8 (6)	C35—C36—C39	121.0 (6)
O8—C10—C12	117.9 (6)	C37—C36—C39	123.1 (6)
C12—C11—C9	122.7 (6)	C36—C37—H37	119.8
C16—C11—C9	117.9 (6)	C38—C37—C36	120.5 (6)
C16—C11—C12	119.4 (6)	C38—C37—H37	119.8
C11—C12—C10	125.2 (6)	N3—C38—C37	123.4 (6)
C13—C12—C10	117.7 (5)	N3—C38—H38	118.3
C13—C12—C11	117.0 (6)	C37—C38—H38	118.3
C12—C13—Cl2	119.9 (5)	C36—C39—H39A	109.5
C12—C13—C14	123.6 (6)	C36—C39—H39B	109.5
C14—C13—Cl2	116.6 (5)	C36—C39—H39C	109.5
C13—C14—H14	121.0	H39A—C39—H39B	109.5
C15—C14—C13	118.0 (8)	H39A—C39—H39C	109.5
C15—C14—H14	121.0	H39B—C39—H39C	109.5
C14—C15—H15	119.9
Zn1—O1—C1—O2	18.8 (10)	N3—C34—C35—C36	0.5 (9)
Zn1—O1—C1—C3	−159.9 (4)	N4—Zn2—O5—C9	34.9 (7)
Zn1ii—O3—C1A—O4	22.0 (9)	N4—Zn2—N3—C34	−4.7 (4)
Zn1ii—O3—C1A—C4	−152.6 (4)	N4—Zn2—N3—C38	−179.3 (6)
Zn1—N1—C17—C18	176.6 (5)	N4—C29—C30—C31	−1.0 (11)
Zn1—N1—C21—C20	−178.3 (5)	N4—C33—C34—N3	−1.9 (8)
Zn1—N1—C21—C22	4.9 (6)	N4—C33—C34—C35	178.3 (6)
Zn1—N2—C22—C21	−3.0 (6)	C1—C3—C4—C1A	1.6 (10)
Zn1—N2—C22—C23	175.9 (4)	C1—C3—C4—C5	−178.7 (6)
Zn1—N2—C26—C25	−175.1 (6)	C1—C3—C8—C7	176.6 (6)
Zn2—O5—C9—O6	6.5 (12)	C1A—C4—C5—Cl1	2.7 (9)
Zn2—O5—C9—C11	−173.1 (4)	C1A—C4—C5—C6	−178.4 (6)
Zn2i—O7—C10—O8	17.5 (8)	C2—C31—C32—C33	178.9 (7)
Zn2i—O7—C10—C12	−155.3 (4)	C3—C4—C5—Cl1	−177.0 (5)
Zn2—N3—C34—C33	5.0 (6)	C3—C4—C5—C6	1.9 (10)
Zn2—N3—C34—C35	−175.2 (4)	C4—C3—C8—C7	−1.3 (10)
Zn2—N3—C38—C37	173.7 (6)	C4—C5—C6—C7	−0.9 (12)
Zn2—N4—C29—C30	−176.3 (5)	C5—C6—C7—C8	−1.3 (12)
Zn2—N4—C33—C32	178.6 (5)	C6—C7—C8—C3	2.3 (11)
Zn2—N4—C33—C34	−2.0 (6)	C8—C3—C4—C1A	179.5 (6)
Cl1—C5—C6—C7	178.0 (6)	C8—C3—C4—C5	−0.8 (10)
Cl2—C13—C14—C15	179.1 (5)	C9—C11—C12—C10	3.1 (9)
O1—Zn1—N1—C17	−90.0 (5)	C9—C11—C12—C13	178.9 (5)
O1—Zn1—N1—C21	84.6 (4)	C9—C11—C16—C15	−178.7 (6)
O1—Zn1—N2—C22	−118.1 (4)	C10—C12—C13—Cl2	−3.1 (7)
O1—Zn1—N2—C26	59.4 (6)	C10—C12—C13—C14	177.4 (6)
O1—C1—C3—C4	−160.0 (6)	C11—C12—C13—Cl2	−179.2 (4)
O1—C1—C3—C8	22.1 (9)	C11—C12—C13—C14	1.3 (9)
O1W—Zn1—O1—C1	−108.3 (5)	C12—C11—C16—C15	1.5 (10)
O1W—Zn1—N1—C17	17.3 (5)	C12—C13—C14—C15	−1.4 (10)
O1W—Zn1—N1—C21	−168.0 (4)	C13—C14—C15—C16	1.4 (11)
O1W—Zn1—N2—C22	61.4 (8)	C14—C15—C16—C11	−1.5 (11)
O1W—Zn1—N2—C26	−121.2 (6)	C16—C11—C12—C10	−177.1 (6)
O2—C1—C3—C4	21.2 (10)	C16—C11—C12—C13	−1.3 (8)
O2—C1—C3—C8	−156.7 (6)	C17—N1—C21—C20	−3.4 (9)
O3i—Zn1—O1—C1	159.2 (5)	C17—N1—C21—C22	179.8 (5)
O3i—Zn1—N1—C17	109.8 (5)	C17—C18—C19—C20	−0.3 (10)
O3i—Zn1—N1—C21	−75.6 (5)	C17—C18—C19—C27	178.9 (7)
O3i—Zn1—N2—C22	143.3 (4)	C18—C19—C20—C21	−0.9 (9)
O3i—Zn1—N2—C26	−39.3 (6)	C19—C20—C21—N1	2.8 (9)
O3—C1A—C4—C3	−106.9 (7)	C19—C20—C21—C22	179.4 (5)
O3—C1A—C4—C5	73.4 (7)	C20—C21—C22—N2	−178.0 (6)
O4—C1A—C4—C3	77.9 (8)	C20—C21—C22—C23	3.2 (9)
O4—C1A—C4—C5	−101.8 (7)	C21—N1—C17—C18	2.1 (9)
O5—Zn2—N3—C34	101.7 (4)	C21—C22—C23—C24	179.3 (6)
O5—Zn2—N3—C38	−72.9 (6)	C22—N2—C26—C25	2.3 (11)
O5—Zn2—N4—C29	63.2 (6)	C22—C23—C24—C25	0.4 (9)
O5—Zn2—N4—C33	−111.5 (4)	C22—C23—C24—C28	177.5 (6)
O5—C9—C11—C12	−171.7 (6)	C23—C24—C25—C26	0.1 (11)
O5—C9—C11—C16	8.5 (9)	C24—C25—C26—N2	−1.4 (12)
O6—C9—C11—C12	8.7 (10)	C26—N2—C22—C21	179.3 (6)
O6—C9—C11—C16	−171.1 (7)	C26—N2—C22—C23	−1.8 (9)
O7ii—Zn2—O5—C9	157.7 (6)	C27—C19—C20—C21	179.9 (7)
O7ii—Zn2—N3—C34	−119.5 (4)	C28—C24—C25—C26	−177.0 (7)
O7ii—Zn2—N3—C38	65.9 (7)	C29—N4—C33—C32	3.5 (9)
O7ii—Zn2—N4—C29	−53.1 (6)	C29—N4—C33—C34	−177.2 (6)
O7ii—Zn2—N4—C33	132.3 (4)	C29—C30—C31—C2	−177.3 (7)
O7—C10—C12—C11	−99.1 (7)	C29—C30—C31—C32	2.2 (10)
O7—C10—C12—C13	85.1 (7)	C30—C31—C32—C33	−0.7 (10)
O8—C10—C12—C11	87.7 (8)	C31—C32—C33—N4	−2.2 (9)
O8—C10—C12—C13	−88.1 (7)	C31—C32—C33—C34	178.6 (5)
N1—Zn1—O1—C1	−7.1 (6)	C32—C33—C34—N3	177.4 (6)
N1—Zn1—N2—C22	4.2 (4)	C32—C33—C34—C35	−2.4 (9)
N1—Zn1—N2—C26	−178.4 (6)	C33—N4—C29—C30	−1.9 (10)
N1—C17—C18—C19	−0.3 (10)	C33—C34—C35—C36	−179.8 (5)
N1—C21—C22—N2	−1.2 (7)	C34—N3—C38—C37	−0.7 (11)
N1—C21—C22—C23	180.0 (6)	C34—C35—C36—C37	−0.2 (9)
N2—Zn1—O1—C1	71.5 (5)	C34—C35—C36—C39	−179.9 (6)
N2—Zn1—N1—C17	−179.5 (5)	C35—C36—C37—C38	−0.5 (10)
N2—Zn1—N1—C21	−4.9 (4)	C36—C37—C38—N3	1.0 (12)
N2—C22—C23—C24	0.5 (9)	C38—N3—C34—C33	−179.8 (6)
N3—Zn2—O5—C9	−54.4 (7)	C38—N3—C34—C35	0.0 (9)
N3—Zn2—N4—C29	178.3 (6)	C39—C36—C37—C38	179.2 (7)
N3—Zn2—N4—C33	3.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4iii	0.85	2.10	2.768 (6)	135
O1W—H1WB···O4i	0.85	1.79	2.644 (6)	179
O1W—H1WB···O3i	0.85	2.43	2.930 (5)	118
C17—H17···O4iii	0.93	2.36	3.202 (8)	150
C20—H20···O6iv	0.93	2.28	3.171 (8)	160
C23—H23···O6iv	0.93	2.40	3.306 (8)	164
C32—H32···O2iii	0.93	2.57	3.459 (8)	161
C35—H35···O2iii	0.93	2.45	3.353 (8)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4i	0.85	2.10	2.768 (6)	135
O1W—H1WB⋯O4ii	0.85	1.79	2.644 (6)	179
O1W—H1WB⋯O3ii	0.85	2.43	2.930 (5)	118
C17—H17⋯O4i	0.93	2.36	3.202 (8)	150
C20—H20⋯O6iii	0.93	2.28	3.171 (8)	160
C23—H23⋯O6iii	0.93	2.40	3.306 (8)	164
C32—H32⋯O2i	0.93	2.57	3.459 (8)	161
C35—H35⋯O2i	0.93	2.45	3.353 (8)	165

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