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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1374–m1375.
Published online 2009 October 17. doi:  10.1107/S1600536809041634
PMCID: PMC2971239

(Propane-1,3-diammonium) bis­(4-hydroxy­pyridine-2,6-dicarboxyl­ato-κ3 O 2,N,O 6)zinc(II) 3.5-hydrate

Abstract

The asymmetric unit of the title compound, (C3H12N2)[Zn(C7H3NO5)2]·3.5H2O, contains two formula units. The compound consists of an anionic complex, a doubly protonated propane-1,3-diamine as a counter-ion and 3.5 uncoord­inated water mol­ecules. The coordination polyhedron around the ZnII atom is distorted octa­hedral, defined by four O atoms and two N atoms from two Hchel (H3chel = 4-hydroxy­pyridine-2,6-dicarboxylic acid) ligands. In the crystal structure, O—H(...)O, N—H(...)O and C—H(...)O hydrogen bonds along with π–π stacking inter­actions [centroid–centroid distance = 3.473 (2) Å] are observed to reinforce the crystal cohesion.

Related literature

For related structures, see: Aghabozorg et al. (2007 [triangle], 2008a [triangle],b [triangle]); Hall et al. (2000 [triangle]); Ramos Silva et al. (2008 [triangle]); Soleimannejad et al. (2009 [triangle]); Zhou et al. (2003 [triangle], 2007 [triangle]); Zou et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1374-scheme1.jpg

Experimental

Crystal data

  • (C3H12N2)[Zn(C7H3NO5)2]·3.5H2O
  • M r = 566.78
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1374-efi2.jpg
  • a = 11.853 (3) Å
  • b = 12.633 (2) Å
  • c = 15.333 (3) Å
  • β = 98.93 (3)°
  • V = 2268.1 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.16 mm−1
  • T = 120 K
  • 0.25 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.757, T max = 0.891
  • 24459 measured reflections
  • 11831 independent reflections
  • 9079 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.080
  • S = 1.00
  • 11831 reflections
  • 659 parameters
  • 14 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.61 e Å−3
  • Δρmin = −0.38 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 5792 Friedel pairs
  • Flack parameter: 0.492 (8)

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041634/hy2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041634/hy2228Isup2.hkl

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

Acknowledgments

The authors are grateful to University of Kurdistan for financial support of this work.

supplementary crystallographic information

Comment

There are several reports on coordination of 4-hydroxypyridine-2,6-dicarboxylic acid (H3chel) to metals, such as [Fe(Hchel)Cl(H2O)2](18-crown-6).2H2O (Zhou et al., 2007), [Cu(Hchel)(dmp].3H2O (Soleimannejad et al., 2009), Na5[Gd(chel)2(Hchel)].16H2O (Hall et al., 2000) and (tataH)2[Cu(Hchel)2.6H2O (tata = 2,4,6-triamino-1,3,5-triazine) (Ramos Silva et al., 2008), (GH)2[Ni(Hchel)2].2H2O (G = guanidine) (Aghabozorg et al., 2008b), [Zn(chel)(H2O)3].0.25CH3CN.H2O (Zhou et al., 2003), [Zn3(chel)2.8H2O]n (Zou et al., 2009), [Zn12(Hchel)12(H2O)10.12H2O]n (Aghabozorg et al., 2007), and the most similar to the title compound, (pnH2)[Hg(Hchel)Cl(H2O)]2.4H2O (pn = propane-1,3-diamine) (Aghabozorg et al., 2008a).

The title compound has two molecules in the asymmetric unit (Fig. 1). All Zn—O and Zn—N bond lengths and angles are in normal range (Table 1). In the asymmetric unit, the two complexes slightly differ in bond lengths and bond angles. Both complexes have a six-coordinated octahedral geometry around the ZnII atom. The N1—Zn1—N2 and N3—Zn2—N4 angles, 157.03 (13) and 160.29 (12)°, respectively, are the nearest angles to linearity, so it can be concluded that the N atoms of the two Hchel ligands locate at the axial positions, and the other atoms at the equatorial positions of the distorted octahedral geometry.

The crystal structure contains many O—H···O, N—H···O and C—H···O hydrogen bonds, shown in Table 2. The π–π stacking with centroid–centroid distance of 3.473 (2) Å is illustrated in Fig. 2. The crystal packing is shown in Fig. 3.

Experimental

From a solution of propane-1,3-diamine (0.029 g, 0.4 mmol) and 4-hydroxypyridine-2,6-dicarboxylic acid (0.073 g, 0.4 mmol) in THF (30 ml), a white precipitate was obtained. By mixing the precipitate with Zn(NO3)2.6H2O (0.052 g, 0.2 mmol) in water (25 ml) and heating for 2 h at 333 K, colourless crystals of the title compound were obtained after allowing the mixture to stand for four weeks at room temperature.

Refinement

H atoms of OH and NH3 groups and water molecules were found in difference Fourier maps. The H atoms bound to O5, O15, O1W and O2W were refined with Uiso(H) = 1.2Ueq(O), and the others were refined as riding atoms, with Uiso(H) = 1.2Ueq(O,N). H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 (aromatic) and 0.97 (CH2) Å and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines denote hydrogen bonds.
Fig. 2.
The π–π stacking interaction (dotted line), with centroid–centroid distance of 3.473 (2) Å. [Symmetry code: (i) x, -y, -1/2+z.]
Fig. 3.
The crystal packing of the title compound.

Crystal data

(C3H12N2)[Zn(C7H3NO5)2]·3.5H2OF(000) = 1172
Mr = 566.78Dx = 1.660 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 587 reflections
a = 11.853 (3) Åθ = 3–29°
b = 12.633 (2) ŵ = 1.16 mm1
c = 15.333 (3) ÅT = 120 K
β = 98.93 (3)°Plate, colorless
V = 2268.1 (8) Å30.25 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer11831 independent reflections
Radiation source: fine-focus sealed tube9079 reflections with I > 2σ(I)
graphiteRint = 0.037
[var phi] and ω scansθmax = 29.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.757, Tmax = 0.891k = −17→17
24459 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080w = 1/[σ2(Fo2) + (0.026P)2 + 0.24P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
11831 reflectionsΔρmax = 0.61 e Å3
659 parametersΔρmin = −0.38 e Å3
14 restraintsAbsolute structure: Flack (1983), 5792 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.492 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Zn10.50235 (3)0.46750 (3)0.88270 (2)0.01608 (10)
O10.6535 (2)0.53464 (18)0.85562 (18)0.0177 (6)
O20.7867 (2)0.5165 (2)0.76790 (18)0.0218 (6)
O30.3643 (2)0.32454 (19)0.86439 (16)0.0219 (6)
O40.3500 (2)0.16616 (18)0.79754 (15)0.0236 (5)
O50.5712 (3)0.2441 (2)0.54295 (18)0.0228 (6)
H5O0.613 (3)0.272 (3)0.512 (2)0.027*
N10.5313 (2)0.3803 (2)0.77863 (19)0.0145 (7)
C10.6915 (3)0.4956 (3)0.7887 (2)0.0159 (8)
C20.6169 (3)0.4132 (3)0.7370 (3)0.0155 (8)
C30.6351 (3)0.3701 (3)0.6581 (2)0.0154 (8)
H3A0.69460.39430.63040.018*
C40.5629 (3)0.2894 (3)0.6200 (2)0.0170 (8)
C50.4795 (3)0.2504 (3)0.6674 (2)0.0172 (8)
H5A0.43390.19330.64610.021*
C60.4662 (3)0.2980 (3)0.7460 (2)0.0151 (8)
C70.3843 (3)0.2600 (3)0.8063 (2)0.0191 (8)
O60.3962 (2)0.59727 (19)0.82811 (16)0.0189 (6)
O70.2541 (2)0.7022 (2)0.85680 (17)0.0221 (6)
O80.5893 (2)0.3753 (2)0.99522 (17)0.0181 (6)
O90.5808 (2)0.3416 (2)1.13726 (17)0.0193 (6)
O100.2270 (2)0.5656 (2)1.17553 (17)0.0249 (6)
H10O0.17250.61301.15890.030*
N20.4233 (3)0.5118 (2)0.9829 (2)0.0144 (7)
C80.3277 (3)0.6312 (3)0.8767 (2)0.0175 (8)
C90.3388 (3)0.5825 (3)0.9677 (2)0.0146 (8)
C100.2703 (3)0.6058 (3)1.0312 (2)0.0158 (8)
H10A0.21370.65741.02150.019*
C110.2901 (3)0.5481 (3)1.1109 (3)0.0161 (8)
C120.3777 (3)0.4745 (3)1.1256 (3)0.0124 (8)
H12A0.39160.43641.17810.015*
C130.4437 (3)0.4593 (3)1.0600 (3)0.0141 (8)
C140.5452 (3)0.3849 (3)1.0661 (3)0.0141 (8)
Zn2−0.12188 (3)−0.02728 (3)1.01277 (2)0.01528 (10)
O110.0296 (2)−0.14519 (19)1.04823 (16)0.0196 (6)
O120.0786 (2)−0.2812 (2)1.14128 (17)0.0319 (6)
O13−0.2797 (2)0.0411 (2)1.03501 (18)0.0184 (6)
O14−0.4204 (2)0.0173 (2)1.11457 (18)0.0206 (6)
O15−0.2106 (2)−0.2439 (2)1.35147 (18)0.0237 (6)
H15O−0.269 (3)−0.216 (3)1.372 (2)0.028*
N3−0.1529 (2)−0.1050 (2)1.1203 (2)0.0146 (6)
C150.0181 (3)−0.2057 (3)1.1134 (2)0.0210 (8)
C16−0.0838 (3)−0.1806 (3)1.1597 (2)0.0154 (8)
C17−0.1023 (3)−0.2290 (3)1.2367 (2)0.0182 (8)
H17A−0.0533−0.28161.26260.022*
C18−0.1958 (3)−0.1973 (3)1.2748 (2)0.0168 (8)
C19−0.2690 (3)−0.1203 (3)1.2332 (2)0.0167 (8)
H19A−0.3322−0.09821.25750.020*
C20−0.2460 (3)−0.0772 (3)1.1549 (2)0.0132 (8)
C21−0.3222 (3)0.0008 (3)1.0986 (3)0.0155 (8)
O16−0.0287 (2)0.1199 (2)1.06223 (17)0.0182 (6)
O170.1104 (2)0.2269 (2)1.03114 (16)0.0181 (6)
O18−0.1961 (2)−0.1272 (2)0.90562 (17)0.0183 (6)
O19−0.1854 (2)−0.1664 (2)0.76526 (18)0.0237 (6)
O200.1724 (2)0.0551 (2)0.73170 (17)0.0210 (6)
H20O0.22490.10160.74000.025*
N4−0.0427 (3)0.0196 (2)0.9128 (2)0.0131 (7)
C220.0418 (3)0.1510 (3)1.0141 (2)0.0165 (8)
C230.0400 (3)0.0918 (3)0.9267 (2)0.0130 (8)
C240.1146 (3)0.1069 (3)0.8686 (2)0.0144 (8)
H24A0.17200.15760.87940.017*
C250.1029 (3)0.0445 (3)0.7922 (3)0.0153 (8)
C260.0155 (3)−0.0297 (3)0.7771 (3)0.0152 (8)
H26A0.0054−0.07120.72640.018*
C27−0.0557 (3)−0.0399 (3)0.8396 (3)0.0125 (8)
C28−0.1520 (3)−0.1184 (3)0.8355 (3)0.0158 (8)
N50.4016 (3)−0.0146 (2)0.4508 (2)0.0209 (7)
H5NA0.4519−0.01890.49760.025*
H5NB0.35270.00150.48470.025*
H5NC0.3881−0.07300.42230.025*
N60.4727 (2)0.1754 (2)0.20851 (17)0.0222 (6)
H6NA0.49420.12040.18240.027*
H6NB0.40070.17830.21080.027*
H6NC0.49590.23430.18940.027*
C290.4101 (3)0.0808 (3)0.3943 (2)0.0207 (7)
H29A0.41040.14430.42990.025*
H29B0.34410.08370.34820.025*
C300.5171 (3)0.0768 (3)0.3532 (2)0.0222 (8)
H30A0.51340.01540.31500.027*
H30B0.58180.06730.39970.027*
C310.5382 (3)0.1748 (3)0.2996 (2)0.0213 (8)
H31A0.51790.23730.33060.026*
H31B0.61900.17910.29600.026*
N70.8201 (3)0.2833 (2)0.1175 (2)0.0263 (7)
H7NA0.85280.24210.08430.032*
H7NB0.83400.27380.17360.032*
H7NC0.75340.30850.12050.032*
N80.9664 (3)0.5324 (2)−0.0880 (2)0.0232 (7)
H8NA0.98210.5988−0.08390.028*
H8NB0.90290.5212−0.12230.028*
H8NC1.01920.4900−0.09900.028*
C320.8925 (3)0.3776 (3)0.1081 (2)0.0256 (8)
H32A0.97130.36150.13200.031*
H32B0.86800.43590.14170.031*
C330.8851 (3)0.4100 (3)0.0125 (2)0.0211 (7)
H33A0.91400.3533−0.02050.025*
H33B0.80580.4222−0.01250.025*
C340.9533 (3)0.5094 (3)0.0042 (2)0.0227 (7)
H34A0.91560.56870.02770.027*
H34B1.02830.50180.03930.027*
O1W0.7384 (3)0.6872 (2)0.96956 (19)0.0235 (6)
H1WA0.758 (3)0.737 (3)0.941 (3)0.028*
H1WB0.714 (3)0.642 (3)0.929 (2)0.028*
O2W0.6128 (2)0.1819 (2)0.91942 (18)0.0229 (6)
H2WA0.602 (3)0.233 (3)0.951 (2)0.027*
H2WB0.643 (3)0.137 (3)0.961 (2)0.027*
O3W0.1322 (2)0.62023 (18)0.39603 (17)0.0344 (6)
H3WA0.12630.66420.43440.041*
H3WB0.19580.64130.38940.041*
O4W0.2384 (2)0.0285 (2)0.56029 (16)0.0341 (6)
H4WA0.25480.00460.61040.041*
H4WB0.17360.05260.55670.041*
O5W0.23614 (19)0.81030 (18)0.70209 (15)0.0255 (5)
H5WA0.23150.76550.74010.031*
H5WB0.18930.80100.65750.031*
O6W0.0423 (2)0.73460 (18)0.90019 (17)0.0248 (6)
H6WA0.03330.77590.93980.030*
H6WB0.09650.73390.87280.030*
O7W0.3576 (2)0.21434 (19)1.02412 (16)0.0246 (6)
H7WA0.35530.25660.98330.030*
H7WB0.29130.22191.03220.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0172 (2)0.0175 (2)0.0147 (2)−0.00004 (18)0.00636 (18)−0.00176 (18)
O10.0188 (15)0.0194 (14)0.0159 (15)−0.0038 (11)0.0052 (12)−0.0028 (10)
O20.0157 (14)0.0304 (15)0.0201 (14)−0.0037 (12)0.0051 (11)0.0000 (11)
O30.0209 (13)0.0257 (14)0.0201 (14)−0.0004 (11)0.0062 (11)−0.0026 (11)
O40.0232 (13)0.0202 (12)0.0284 (13)−0.0076 (10)0.0066 (11)−0.0002 (10)
O50.0300 (15)0.0262 (14)0.0145 (14)−0.0010 (12)0.0109 (11)−0.0053 (11)
N10.0120 (15)0.0170 (15)0.0139 (16)−0.0012 (12)0.0002 (12)0.0007 (12)
C10.021 (2)0.0150 (17)0.0120 (18)0.0005 (15)0.0040 (15)0.0070 (15)
C20.0155 (19)0.0157 (17)0.0150 (19)0.0014 (15)0.0012 (15)0.0042 (15)
C30.0195 (18)0.0145 (17)0.0131 (18)0.0015 (14)0.0056 (15)−0.0007 (14)
C40.0175 (18)0.0148 (17)0.018 (2)0.0005 (14)0.0012 (15)−0.0015 (15)
C50.0159 (18)0.0174 (18)0.0179 (19)0.0000 (14)0.0011 (14)−0.0027 (14)
C60.0158 (18)0.0129 (16)0.0160 (18)0.0002 (13)0.0005 (14)0.0012 (13)
C70.0126 (17)0.0239 (19)0.0219 (19)−0.0018 (14)0.0060 (14)0.0017 (15)
O60.0258 (14)0.0178 (13)0.0147 (13)0.0015 (11)0.0082 (11)0.0001 (10)
O70.0216 (14)0.0236 (13)0.0220 (14)0.0079 (11)0.0061 (11)0.0087 (11)
O80.0186 (13)0.0195 (13)0.0178 (14)0.0053 (11)0.0085 (11)0.0013 (11)
O90.0195 (14)0.0183 (13)0.0198 (15)0.0033 (11)0.0022 (11)0.0034 (11)
O100.0277 (15)0.0321 (15)0.0172 (14)0.0166 (13)0.0112 (12)0.0091 (12)
N20.0138 (17)0.0142 (15)0.0156 (18)0.0011 (12)0.0033 (14)−0.0003 (13)
C80.0174 (18)0.0218 (19)0.0137 (18)−0.0021 (15)0.0031 (15)0.0016 (14)
C90.0158 (19)0.0171 (18)0.0101 (18)−0.0024 (15)−0.0007 (15)0.0017 (14)
C100.0126 (19)0.0195 (19)0.015 (2)0.0044 (15)0.0004 (16)0.0004 (15)
C110.0175 (19)0.0197 (18)0.0119 (19)−0.0022 (15)0.0048 (15)0.0000 (15)
C120.0136 (18)0.0149 (18)0.0086 (17)0.0021 (14)0.0011 (14)−0.0003 (13)
C130.0138 (19)0.0131 (18)0.015 (2)−0.0035 (14)0.0010 (16)0.0011 (14)
C140.0121 (17)0.0106 (17)0.020 (2)−0.0004 (14)0.0035 (15)−0.0019 (15)
Zn20.0154 (2)0.0173 (2)0.0139 (2)0.00010 (18)0.00470 (18)0.00074 (18)
O110.0136 (12)0.0253 (13)0.0206 (13)0.0047 (10)0.0050 (10)0.0058 (11)
O120.0290 (14)0.0288 (14)0.0389 (16)0.0161 (12)0.0088 (12)0.0054 (12)
O130.0168 (15)0.0226 (14)0.0173 (15)0.0064 (11)0.0077 (12)0.0060 (11)
O140.0158 (13)0.0230 (14)0.0245 (15)0.0031 (11)0.0077 (11)0.0014 (11)
O150.0270 (15)0.0259 (14)0.0190 (14)0.0017 (12)0.0059 (11)0.0054 (11)
N30.0107 (15)0.0167 (15)0.0164 (16)0.0009 (12)0.0022 (13)0.0013 (12)
C150.0166 (17)0.0193 (18)0.027 (2)0.0030 (14)0.0029 (15)−0.0009 (15)
C160.0121 (17)0.0185 (18)0.0161 (18)−0.0037 (13)0.0031 (14)0.0002 (14)
C170.0174 (19)0.0184 (18)0.0175 (19)−0.0024 (14)−0.0014 (15)−0.0013 (14)
C180.0199 (19)0.0203 (18)0.0108 (18)−0.0099 (15)0.0046 (14)0.0016 (15)
C190.0138 (18)0.0176 (18)0.019 (2)−0.0024 (14)0.0049 (15)−0.0027 (15)
C200.0110 (17)0.0156 (17)0.0136 (19)−0.0029 (14)0.0030 (14)−0.0036 (14)
C210.0142 (19)0.0151 (17)0.0166 (19)−0.0002 (15)0.0005 (15)−0.0001 (16)
O160.0205 (13)0.0200 (13)0.0151 (13)−0.0034 (10)0.0066 (10)−0.0035 (10)
O170.0182 (13)0.0217 (13)0.0143 (12)−0.0060 (10)0.0017 (10)−0.0027 (10)
O180.0174 (13)0.0212 (14)0.0175 (14)−0.0040 (11)0.0069 (11)−0.0002 (11)
O190.0216 (14)0.0296 (15)0.0204 (15)−0.0100 (12)0.0054 (12)−0.0081 (12)
O200.0227 (14)0.0250 (13)0.0175 (14)−0.0117 (11)0.0100 (11)−0.0058 (11)
N40.0140 (16)0.0165 (16)0.0088 (16)0.0002 (13)0.0015 (13)−0.0002 (12)
C220.0164 (18)0.0157 (17)0.0163 (19)0.0008 (14)−0.0010 (15)0.0005 (14)
C230.0122 (18)0.0100 (16)0.0163 (19)−0.0009 (14)0.0000 (15)0.0025 (14)
C240.0145 (19)0.0126 (17)0.016 (2)−0.0009 (15)0.0025 (16)−0.0018 (14)
C250.0131 (19)0.0181 (18)0.0148 (19)−0.0013 (14)0.0026 (15)0.0022 (15)
C260.0147 (19)0.0146 (18)0.016 (2)0.0007 (14)0.0013 (15)−0.0042 (14)
C270.0102 (18)0.0130 (18)0.013 (2)−0.0021 (14)−0.0014 (15)0.0024 (14)
C280.0132 (18)0.0172 (18)0.0170 (19)0.0023 (15)0.0027 (15)−0.0020 (15)
N50.0171 (15)0.0196 (15)0.0254 (18)0.0002 (12)0.0016 (13)−0.0045 (13)
N60.0213 (15)0.0205 (14)0.0260 (15)0.0038 (12)0.0069 (12)0.0013 (12)
C290.0233 (18)0.0172 (17)0.0216 (17)−0.0001 (14)0.0030 (14)0.0024 (14)
C300.0160 (17)0.0241 (18)0.026 (2)0.0000 (14)0.0006 (15)0.0039 (15)
C310.0167 (18)0.0242 (19)0.0222 (19)0.0006 (15)0.0002 (15)0.0004 (15)
N70.0214 (16)0.0316 (17)0.0272 (17)0.0113 (14)0.0080 (13)0.0018 (14)
N80.0185 (16)0.0197 (15)0.0299 (19)0.0001 (12)−0.0005 (13)−0.0035 (13)
C320.0252 (19)0.031 (2)0.0220 (18)0.0004 (16)0.0073 (15)−0.0004 (15)
C330.0190 (18)0.0220 (17)0.0216 (18)0.0035 (15)0.0005 (14)−0.0013 (15)
C340.0241 (18)0.0264 (18)0.0170 (17)−0.0012 (15)0.0017 (14)−0.0004 (14)
O1W0.0332 (15)0.0187 (14)0.0200 (15)−0.0064 (12)0.0090 (12)−0.0002 (11)
O2W0.0331 (16)0.0172 (13)0.0185 (15)0.0068 (11)0.0044 (12)0.0023 (11)
O3W0.0301 (14)0.0278 (14)0.0491 (17)−0.0086 (12)0.0184 (13)−0.0109 (12)
O4W0.0255 (14)0.0562 (18)0.0217 (13)0.0094 (13)0.0067 (11)−0.0025 (13)
O5W0.0251 (13)0.0329 (14)0.0172 (12)−0.0035 (11)−0.0009 (10)0.0069 (10)
O6W0.0275 (14)0.0194 (13)0.0301 (15)0.0026 (11)0.0126 (12)0.0022 (11)
O7W0.0204 (13)0.0264 (13)0.0277 (15)−0.0008 (11)0.0058 (11)−0.0004 (11)

Geometric parameters (Å, °)

Zn1—N12.012 (3)O17—C221.259 (4)
Zn1—N21.999 (3)O18—C281.271 (4)
Zn1—O12.081 (3)O19—C281.246 (4)
Zn1—O32.424 (3)O20—C251.340 (5)
Zn1—O62.155 (3)O20—H20O0.8504
Zn1—O82.201 (3)N4—C231.331 (5)
O1—C11.282 (5)N4—C271.340 (5)
O2—C11.247 (5)C22—C231.533 (5)
O3—C71.257 (4)C23—C241.362 (5)
O4—C71.254 (4)C24—C251.401 (5)
O5—C41.330 (5)C24—H24A0.9300
O5—H5O0.82 (3)C25—C261.390 (5)
N1—C61.345 (4)C26—C271.378 (6)
N1—C21.345 (5)C26—H26A0.9300
C1—C21.508 (5)C27—C281.506 (5)
C2—C31.374 (5)N5—C291.497 (4)
C3—C41.399 (5)N5—H5NA0.8599
C3—H3A0.9300N5—H5NB0.8600
C4—C51.404 (5)N5—H5NC0.8601
C5—C61.377 (5)N6—C311.489 (4)
C5—H5A0.9300N6—H6NA0.8601
C6—C71.519 (5)N6—H6NB0.8600
O6—C81.259 (4)N6—H6NC0.8599
O7—C81.256 (5)C29—C301.501 (4)
O8—C141.283 (4)C29—H29A0.9700
O9—C141.235 (4)C29—H29B0.9700
O10—C111.349 (5)C30—C311.528 (5)
O10—H10O0.8881C30—H30A0.9700
N2—C91.335 (5)C30—H30B0.9700
N2—C131.345 (5)C31—H31A0.9700
C8—C91.510 (5)C31—H31B0.9700
C9—C101.394 (5)N7—C321.488 (4)
C10—C111.412 (5)N7—H7NA0.8601
C10—H10A0.9300N7—H7NB0.8600
C11—C121.386 (5)N7—H7NC0.8599
C12—C131.380 (5)N8—C341.475 (4)
C12—H12A0.9300N8—H8NA0.8601
C13—C141.518 (5)N8—H8NB0.8600
Zn2—N32.001 (3)N8—H8NC0.8598
Zn2—N42.007 (3)C32—C331.512 (5)
Zn2—O112.331 (2)C32—H32A0.9700
Zn2—O132.135 (3)C32—H32B0.9700
Zn2—O162.234 (3)C33—C341.510 (5)
Zn2—O182.149 (3)C33—H33A0.9700
O11—C151.283 (4)C33—H33B0.9700
O12—C151.229 (4)C34—H34A0.9700
O13—C211.272 (5)C34—H34B0.9700
O14—C211.244 (5)O1W—H1WA0.81 (3)
O15—C181.351 (4)O1W—H1WB0.86 (3)
O15—H15O0.88 (2)O2W—H2WA0.84 (3)
N3—C161.340 (4)O2W—H2WB0.89 (3)
N3—C201.344 (5)O3W—H3WA0.8200
C15—C161.526 (5)O3W—H3WB0.8199
C16—C171.376 (5)O4W—H4WA0.8200
C17—C181.389 (5)O4W—H4WB0.8200
C17—H17A0.9300O5W—H5WA0.8199
C18—C191.391 (5)O5W—H5WB0.8200
C19—C201.384 (5)O6W—H6WA0.8200
C19—H19A0.9300O6W—H6WB0.8200
C20—C211.513 (5)O7W—H7WA0.8201
O16—C221.260 (4)O7W—H7WB0.8200
N2—Zn1—N1157.03 (13)C20—C19—H19A120.6
N2—Zn1—O1124.02 (12)C18—C19—H19A120.6
N1—Zn1—O178.86 (12)N3—C20—C19121.6 (3)
N2—Zn1—O676.72 (11)N3—C20—C21113.5 (3)
N1—Zn1—O6105.64 (11)C19—C20—C21124.8 (3)
O1—Zn1—O694.67 (10)O14—C21—O13125.3 (4)
N2—Zn1—O876.36 (11)O14—C21—C20119.4 (3)
N1—Zn1—O8102.43 (11)O13—C21—C20115.2 (3)
O1—Zn1—O893.39 (10)C22—O16—Zn2113.5 (2)
O6—Zn1—O8151.79 (10)C28—O18—Zn2115.0 (2)
N2—Zn1—O384.80 (11)C25—O20—H20O118.6
N1—Zn1—O372.27 (11)C23—N4—C27120.3 (3)
O1—Zn1—O3150.12 (9)C23—N4—Zn2120.0 (3)
O6—Zn1—O3100.28 (9)C27—N4—Zn2117.9 (2)
O8—Zn1—O385.54 (9)O17—C22—O16125.6 (3)
C1—O1—Zn1115.0 (2)O17—C22—C23118.3 (3)
C7—O3—Zn1111.5 (2)O16—C22—C23116.1 (3)
C4—O5—H5O118 (3)N4—C23—C24121.9 (3)
C6—N1—C2119.6 (3)N4—C23—C22112.6 (3)
C6—N1—Zn1124.1 (2)C24—C23—C22125.5 (3)
C2—N1—Zn1116.2 (2)C23—C24—C25118.5 (3)
O2—C1—O1124.6 (4)C23—C24—H24A120.7
O2—C1—C2119.5 (4)C25—C24—H24A120.7
O1—C1—C2115.8 (3)O20—C25—C26118.4 (4)
N1—C2—C3121.9 (3)O20—C25—C24122.1 (3)
N1—C2—C1112.8 (3)C26—C25—C24119.6 (4)
C3—C2—C1125.2 (3)C27—C26—C25117.9 (4)
C2—C3—C4119.2 (4)C27—C26—H26A121.0
C2—C3—H3A120.4C25—C26—H26A121.0
C4—C3—H3A120.4N4—C27—C26121.8 (3)
O5—C4—C3124.0 (3)N4—C27—C28113.1 (3)
O5—C4—C5117.7 (3)C26—C27—C28125.1 (3)
C3—C4—C5118.2 (3)O19—C28—O18124.8 (4)
C6—C5—C4119.0 (4)O19—C28—C27119.6 (3)
C6—C5—H5A120.5O18—C28—C27115.5 (3)
C4—C5—H5A120.5C29—N5—H5NA115.7
N1—C6—C5121.7 (3)C29—N5—H5NB105.8
N1—C6—C7113.7 (3)H5NA—N5—H5NB87.5
C5—C6—C7124.5 (3)C29—N5—H5NC114.7
O4—C7—O3126.5 (3)H5NA—N5—H5NC114.9
O4—C7—C6117.4 (3)H5NB—N5—H5NC114.9
O3—C7—C6115.8 (3)C31—N6—H6NA106.5
C8—O6—Zn1114.8 (2)C31—N6—H6NB109.8
C14—O8—Zn1114.3 (2)H6NA—N6—H6NB114.9
C11—O10—H10O111.1C31—N6—H6NC100.1
C9—N2—C13120.7 (3)H6NA—N6—H6NC114.0
C9—N2—Zn1118.8 (3)H6NB—N6—H6NC110.4
C13—N2—Zn1119.7 (3)N5—C29—C30110.7 (3)
O7—C8—O6125.9 (4)N5—C29—H29A109.5
O7—C8—C9118.2 (3)C30—C29—H29A109.5
O6—C8—C9115.9 (3)N5—C29—H29B109.5
N2—C9—C10121.5 (3)C30—C29—H29B109.5
N2—C9—C8112.9 (3)H29A—C29—H29B108.1
C10—C9—C8125.6 (3)C29—C30—C31114.7 (3)
C9—C10—C11117.3 (3)C29—C30—H30A108.6
C9—C10—H10A121.3C31—C30—H30A108.6
C11—C10—H10A121.3C29—C30—H30B108.6
O10—C11—C12118.6 (4)C31—C30—H30B108.6
O10—C11—C10120.9 (3)H30A—C30—H30B107.6
C12—C11—C10120.5 (4)N6—C31—C30113.8 (3)
C13—C12—C11118.0 (4)N6—C31—H31A108.8
C13—C12—H12A121.0C30—C31—H31A108.8
C11—C12—H12A121.0N6—C31—H31B108.8
N2—C13—C12121.9 (3)C30—C31—H31B108.8
N2—C13—C14113.1 (3)H31A—C31—H31B107.7
C12—C13—C14125.0 (3)C32—N7—H7NA96.1
O9—C14—O8125.3 (3)C32—N7—H7NB100.6
O9—C14—C13119.2 (3)H7NA—N7—H7NB118.2
O8—C14—C13115.5 (3)C32—N7—H7NC104.9
N3—Zn2—N4160.29 (12)H7NA—N7—H7NC139.3
N3—Zn2—O1377.85 (11)H7NB—N7—H7NC91.9
N4—Zn2—O13121.86 (11)C34—N8—H8NA100.1
N3—Zn2—O18103.62 (11)C34—N8—H8NB110.0
N4—Zn2—O1876.93 (11)H8NA—N8—H8NB111.4
O13—Zn2—O1895.44 (10)C34—N8—H8NC104.7
N3—Zn2—O16105.86 (11)H8NA—N8—H8NC117.7
N4—Zn2—O1675.45 (11)H8NB—N8—H8NC111.9
O13—Zn2—O1690.48 (10)N7—C32—C33111.3 (3)
O18—Zn2—O16150.52 (10)N7—C32—H32A109.4
N3—Zn2—O1174.19 (10)C33—C32—H32A109.4
N4—Zn2—O1186.11 (11)N7—C32—H32B109.4
O13—Zn2—O11152.03 (10)C33—C32—H32B109.4
O18—Zn2—O1190.70 (10)H32A—C32—H32B108.0
O16—Zn2—O1197.49 (9)C34—C33—C32110.8 (3)
C15—O11—Zn2113.1 (2)C34—C33—H33A109.5
C21—O13—Zn2115.0 (2)C32—C33—H33A109.5
C18—O15—H15O111 (2)C34—C33—H33B109.5
C16—N3—C20119.4 (3)C32—C33—H33B109.5
C16—N3—Zn2123.0 (2)H33A—C33—H33B108.1
C20—N3—Zn2117.6 (2)N8—C34—C33112.4 (3)
O12—C15—O11127.3 (3)N8—C34—H34A109.1
O12—C15—C16117.4 (3)C33—C34—H34A109.1
O11—C15—C16115.2 (3)N8—C34—H34B109.1
N3—C16—C17122.4 (3)C33—C34—H34B109.1
N3—C16—C15114.2 (3)H34A—C34—H34B107.9
C17—C16—C15123.3 (3)H1WA—O1W—H1WB102 (4)
C16—C17—C18118.4 (4)H2WA—O2W—H2WB100 (4)
C16—C17—H17A120.8H3WA—O3W—H3WB93.0
C18—C17—H17A120.8H4WA—O4W—H4WB106.5
O15—C18—C17117.4 (3)H5WA—O5W—H5WB112.4
O15—C18—C19123.2 (3)H6WA—O6W—H6WB126.0
C17—C18—C19119.4 (3)H7WA—O7W—H7WB97.0
C20—C19—C18118.7 (3)
N2—Zn1—O1—C1179.8 (2)O13—Zn2—O11—C153.0 (4)
N1—Zn1—O1—C12.0 (3)O18—Zn2—O11—C15−100.0 (2)
O6—Zn1—O1—C1−103.1 (3)O16—Zn2—O11—C15108.4 (2)
O8—Zn1—O1—C1104.0 (3)N3—Zn2—O13—C21−3.4 (3)
O3—Zn1—O1—C117.0 (4)N4—Zn2—O13—C21177.4 (3)
N2—Zn1—O3—C7−174.3 (2)O18—Zn2—O13—C2199.4 (3)
N1—Zn1—O3—C76.9 (2)O16—Zn2—O13—C21−109.5 (3)
O1—Zn1—O3—C7−8.6 (3)O11—Zn2—O13—C21−2.4 (4)
O6—Zn1—O3—C7110.2 (2)N4—Zn2—N3—C16−2.9 (5)
O8—Zn1—O3—C7−97.7 (2)O13—Zn2—N3—C16179.0 (3)
N2—Zn1—N1—C61.0 (5)O18—Zn2—N3—C1686.3 (3)
O1—Zn1—N1—C6176.4 (3)O16—Zn2—N3—C16−94.0 (3)
O6—Zn1—N1—C6−91.9 (3)O11—Zn2—N3—C16−0.5 (3)
O8—Zn1—N1—C685.3 (3)N4—Zn2—N3—C20175.3 (3)
O3—Zn1—N1—C64.2 (3)O13—Zn2—N3—C20−2.8 (2)
N2—Zn1—N1—C2176.2 (3)O18—Zn2—N3—C20−95.5 (3)
O1—Zn1—N1—C2−8.4 (2)O16—Zn2—N3—C2084.2 (3)
O6—Zn1—N1—C283.3 (3)O11—Zn2—N3—C20177.7 (3)
O8—Zn1—N1—C2−99.5 (3)Zn2—O11—C15—O12172.8 (3)
O3—Zn1—N1—C2179.4 (3)Zn2—O11—C15—C16−6.2 (4)
Zn1—O1—C1—O2−171.5 (3)C20—N3—C16—C17−2.2 (5)
Zn1—O1—C1—C24.1 (4)Zn2—N3—C16—C17175.9 (3)
C6—N1—C2—C34.8 (5)C20—N3—C16—C15179.4 (3)
Zn1—N1—C2—C3−170.6 (3)Zn2—N3—C16—C15−2.5 (4)
C6—N1—C2—C1−171.9 (3)O12—C15—C16—N3−173.1 (3)
Zn1—N1—C2—C112.7 (4)O11—C15—C16—N36.0 (4)
O2—C1—C2—N1164.8 (3)O12—C15—C16—C178.5 (5)
O1—C1—C2—N1−11.0 (5)O11—C15—C16—C17−172.4 (3)
O2—C1—C2—C3−11.8 (6)N3—C16—C17—C18−0.4 (5)
O1—C1—C2—C3172.5 (3)C15—C16—C17—C18177.8 (3)
N1—C2—C3—C4−0.2 (5)C16—C17—C18—O15−178.3 (3)
C1—C2—C3—C4176.0 (3)C16—C17—C18—C191.6 (5)
C2—C3—C4—O5178.2 (4)O15—C18—C19—C20179.7 (3)
C2—C3—C4—C5−4.5 (5)C17—C18—C19—C20−0.2 (5)
O5—C4—C5—C6−177.8 (3)C16—N3—C20—C193.7 (5)
C3—C4—C5—C64.8 (5)Zn2—N3—C20—C19−174.5 (3)
C2—N1—C6—C5−4.5 (5)C16—N3—C20—C21−174.2 (3)
Zn1—N1—C6—C5170.6 (3)Zn2—N3—C20—C217.6 (4)
C2—N1—C6—C7171.9 (3)C18—C19—C20—N3−2.5 (5)
Zn1—N1—C6—C7−13.1 (4)C18—C19—C20—C21175.1 (3)
C4—C5—C6—N1−0.3 (5)Zn2—O13—C21—O14−168.6 (3)
C4—C5—C6—C7−176.3 (3)Zn2—O13—C21—C208.2 (4)
Zn1—O3—C7—O4159.6 (3)N3—C20—C21—O14166.5 (3)
Zn1—O3—C7—C6−15.2 (4)C19—C20—C21—O14−11.3 (6)
N1—C6—C7—O4−156.3 (3)N3—C20—C21—O13−10.5 (5)
C5—C6—C7—O419.9 (5)C19—C20—C21—O13171.7 (3)
N1—C6—C7—O318.9 (4)N3—Zn2—O16—C22148.1 (2)
C5—C6—C7—O3−164.8 (3)N4—Zn2—O16—C22−11.5 (2)
N2—Zn1—O6—C8−7.6 (3)O13—Zn2—O16—C22−134.4 (2)
N1—Zn1—O6—C8148.8 (3)O18—Zn2—O16—C22−32.4 (3)
O1—Zn1—O6—C8−131.5 (3)O11—Zn2—O16—C2272.5 (2)
O8—Zn1—O6—C8−25.3 (4)N3—Zn2—O18—C28−154.0 (3)
O3—Zn1—O6—C874.5 (3)N4—Zn2—O18—C285.7 (3)
N2—Zn1—O8—C145.6 (2)O13—Zn2—O18—C28127.2 (3)
N1—Zn1—O8—C14−150.9 (2)O16—Zn2—O18—C2826.5 (4)
O1—Zn1—O8—C14129.8 (2)O11—Zn2—O18—C28−80.1 (3)
O6—Zn1—O8—C1423.4 (4)N3—Zn2—N4—C23−81.9 (5)
O3—Zn1—O8—C14−80.1 (2)O13—Zn2—N4—C2395.9 (3)
N1—Zn1—N2—C9−90.0 (4)O18—Zn2—N4—C23−175.8 (3)
O1—Zn1—N2—C995.5 (3)O16—Zn2—N4—C2314.6 (3)
O6—Zn1—N2—C98.8 (3)O11—Zn2—N4—C23−84.2 (3)
O8—Zn1—N2—C9−179.7 (3)N3—Zn2—N4—C2782.8 (5)
O3—Zn1—N2—C9−93.1 (3)O13—Zn2—N4—C27−99.5 (3)
N1—Zn1—N2—C1380.0 (4)O18—Zn2—N4—C27−11.2 (3)
O1—Zn1—N2—C13−94.5 (3)O16—Zn2—N4—C27179.2 (3)
O6—Zn1—N2—C13178.8 (3)O11—Zn2—N4—C2780.4 (3)
O8—Zn1—N2—C13−9.7 (3)Zn2—O16—C22—O17−174.4 (3)
O3—Zn1—N2—C1377.0 (3)Zn2—O16—C22—C237.3 (4)
Zn1—O6—C8—O7−176.1 (3)C27—N4—C23—C24−0.9 (5)
Zn1—O6—C8—C95.3 (4)Zn2—N4—C23—C24163.4 (3)
C13—N2—C9—C101.2 (5)C27—N4—C23—C22−179.5 (3)
Zn1—N2—C9—C10171.1 (3)Zn2—N4—C23—C22−15.2 (4)
C13—N2—C9—C8−178.6 (3)O17—C22—C23—N4−174.4 (3)
Zn1—N2—C9—C8−8.7 (4)O16—C22—C23—N44.0 (4)
O7—C8—C9—N2−176.9 (3)O17—C22—C23—C247.0 (5)
O6—C8—C9—N21.7 (5)O16—C22—C23—C24−174.5 (3)
O7—C8—C9—C103.2 (6)N4—C23—C24—C250.2 (5)
O6—C8—C9—C10−178.1 (4)C22—C23—C24—C25178.5 (3)
N2—C9—C10—C11−3.0 (5)C23—C24—C25—O20179.6 (3)
C8—C9—C10—C11176.9 (3)C23—C24—C25—C260.8 (5)
C9—C10—C11—O10−179.6 (3)O20—C25—C26—C27−179.8 (3)
C9—C10—C11—C122.5 (5)C24—C25—C26—C27−1.1 (5)
O10—C11—C12—C13−178.3 (3)C23—N4—C27—C260.7 (5)
C10—C11—C12—C13−0.4 (5)Zn2—N4—C27—C26−163.9 (3)
C9—N2—C13—C121.1 (5)C23—N4—C27—C28179.0 (3)
Zn1—N2—C13—C12−168.7 (3)Zn2—N4—C27—C2814.4 (4)
C9—N2—C13—C14−178.3 (3)C25—C26—C27—N40.3 (5)
Zn1—N2—C13—C1411.9 (4)C25—C26—C27—C28−177.8 (3)
C11—C12—C13—N2−1.5 (5)Zn2—O18—C28—O19−177.3 (3)
C11—C12—C13—C14177.8 (3)Zn2—O18—C28—C270.0 (4)
Zn1—O8—C14—O9−179.1 (3)N4—C27—C28—O19168.4 (3)
Zn1—O8—C14—C13−1.3 (4)C26—C27—C28—O19−13.3 (6)
N2—C13—C14—O9171.6 (3)N4—C27—C28—O18−9.1 (5)
C12—C13—C14—O9−7.8 (5)C26—C27—C28—O18169.2 (3)
N2—C13—C14—O8−6.4 (4)N5—C29—C30—C31−175.7 (3)
C12—C13—C14—O8174.3 (3)C29—C30—C31—N6−81.2 (4)
N3—Zn2—O11—C153.9 (2)N7—C32—C33—C34176.7 (3)
N4—Zn2—O11—C15−176.9 (2)C32—C33—C34—N8169.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5O···O1Wi0.82 (4)1.79 (4)2.577 (5)162 (3)
O10—H10O···O12ii0.891.732.613 (4)170
O15—H15O···O2Wiii0.88 (4)1.73 (4)2.600 (4)170 (4)
O20—H20O···O40.851.802.600 (3)156
N5—H5NA···O14iv0.862.163.019 (4)176
N5—H5NB···O4W0.861.942.804 (4)176
N5—H5NC···O4v0.862.233.019 (4)152
N5—H5NC···O7Wv0.862.442.843 (4)110
N6—H6NA···O14vi0.862.032.870 (4)164
N6—H6NB···O5Wi0.861.942.796 (3)174
N6—H6NC···O9vii0.861.932.771 (4)164
N7—H7NA···O16vi0.862.152.943 (4)153
N7—H7NB···O19iv0.861.992.714 (4)141
N7—H7NC···O9vii0.862.142.991 (4)169
N8—H8NA···O6Wvi0.861.892.724 (4)164
N8—H8NB···O2vii0.862.002.828 (4)160
N8—H8NC···O3Wviii0.861.942.791 (4)169
O1W—H1WA···O18ix0.82 (4)1.90 (4)2.701 (4)164 (4)
O1W—H1WB···O10.86 (3)1.84 (4)2.690 (4)171 (4)
O2W—H2WA···O80.83 (4)1.94 (4)2.738 (4)163 (3)
O2W—H2WB···O13x0.89 (3)1.81 (3)2.688 (4)171 (3)
O3W—H3WA···O17i0.822.052.873 (4)179
O3W—H3WB···O3i0.822.142.950 (3)172
O4W—H4WA···O200.822.322.876 (4)126
O4W—H4WB···O11v0.822.062.862 (3)167
O5W—H5WA···O70.821.942.717 (3)158
O5W—H5WB···O17i0.822.052.846 (3)165
O6W—H6WA···O11ii0.821.942.755 (4)169
O6W—H6WB···O70.821.962.726 (3)154
O7W—H7WA···O30.822.032.829 (3)164
O7W—H7WB···O170.822.142.953 (3)170
C12—H12A···O6xi0.932.333.209 (5)157
C26—H26A···O16v0.932.563.448 (5)160
C31—H31A···O6i0.972.543.398 (5)148
C31—H31B···O19iv0.972.443.400 (4)170
C32—H32B···O2i0.972.373.213 (4)145

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z; (iii) x−1, −y, z+1/2; (iv) x+1, −y, z−1/2; (v) x, −y, z−1/2; (vi) x+1, y, z−1; (vii) x, y, z−1; (viii) x+1, −y+1, z−1/2; (ix) x+1, y+1, z; (x) x+1, y, z; (xi) x, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2228).

References

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