Acridinium (6-carboxy-pyridine-2-carboxyl-ato)(pyridine-2,6-dicarboxyl-ato)zincate(II) penta-hydrate.

The reaction of Zn(NO(3))(2) with pyridine-2,6-dicarboxylic acid (pydcH(2)) and acridine (acr) in aqueous solution leads to the formation of the title compound, (C(13)H(10)N)[Zn(C(7)H(3)NO(4))(C(7)H(4)NO(4))]·5H(2)O or (acrH)[Zn(pydcH)(pydc)]·5H(2)O. In the title compound, the Zn(II) atom is coordinated by four O atoms and two N atoms from the tridentate chelating rings of (pydc)(2-) and (pydcH)(-) anions. The geometry of the resulting ZnN(2)O(4) coordination can be described as distorted octa-hedral. To balance the charges, one protonated acridine (acrH)(+) cation is present. In the crystal structure, extensive O-H⋯O and N-H⋯O hydrogen bonds involving acrH(+), the complex anion and uncoordinated water mol-ecules form a three-dimensional network.

Related literature

For related structures, see: Aghabozorg et al. (2009 ▶); Moghimi et al. (2005 ▶); Ranjbar et al. (2002 ▶); Tabatabaee et al. (2008 ▶); Aghabozorg, Attar Gharamaleki et al. (2008 ▶); Aghabozorg, Firoozi et al. (2008 ▶); Aghabozorg, Manteghi et al. (2008 ▶); Safaei-Ghomi et al. (2009 ▶); Soleimannejad et al. (2008 ▶).

Experimental

Crystal data

(C13H10N)[Zn(C7H3NO4)(C7H4NO4)]·5H2O

M = 666.89

Monoclinic,

a = 9.6083 (5) Å

b = 18.9681 (9) Å

c = 15.5435 (8) Å

β = 96.051 (1)°

V = 2817.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.95 mm−1

T = 120 K

0.60 × 0.14 × 0.14 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.652, T max = 0.879

26948 measured reflections

7457 independent reflections

5795 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.06

7457 reflections

445 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.87 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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/S1600536809011106/bq2129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011106/bq2129Isup2.hkl

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

(C13H10N)[Zn(C7H3NO4)(C7H4NO4)]·5H2O	F(000) = 1376
Mr = 666.89	Dx = 1.572 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8302 reflections
a = 9.6083 (5) Å	θ = 2.2–29.7°
b = 18.9681 (9) Å	µ = 0.95 mm−1
c = 15.5435 (8) Å	T = 120 K
β = 96.051 (1)°	Prism, yellow
V = 2817.0 (2) Å3	0.60 × 0.14 × 0.14 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	7457 independent reflections
Radiation source: normal-focus sealed tube	5795 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 29.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→13
Tmin = 0.652, Tmax = 0.879	k = −25→25
26948 measured reflections	l = −21→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0451P)2 + 2.9525P] where P = (Fo2 + 2Fc2)/3
7457 reflections	(Δ/σ)max = 0.002
445 parameters	Δρmax = 0.87 e Å−3
0 restraints	Δρmin = −0.35 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
Zn1	0.49831 (3)	0.093889 (12)	0.701036 (14)	0.01975 (8)
O1	0.34045 (16)	0.18535 (8)	0.71906 (9)	0.0242 (3)
O2	0.23932 (16)	0.23960 (8)	0.82468 (10)	0.0231 (3)
H2O	0.198 (5)	0.261 (2)	0.779 (3)	0.092 (15)*
O3	0.63925 (16)	0.01596 (8)	0.74853 (9)	0.0227 (3)
O4	0.73383 (16)	−0.03264 (8)	0.87279 (10)	0.0248 (3)
O5	0.32802 (16)	0.02475 (8)	0.65903 (9)	0.0229 (3)
O6	0.20086 (16)	−0.01389 (8)	0.53928 (10)	0.0262 (3)
O7	0.65542 (15)	0.17569 (8)	0.68086 (9)	0.0218 (3)
O8	0.74307 (17)	0.23451 (8)	0.57367 (10)	0.0269 (3)
N1	0.48997 (17)	0.10445 (8)	0.82995 (10)	0.0167 (3)
N2	0.48458 (17)	0.10381 (8)	0.57225 (10)	0.0155 (3)
C1	0.4084 (2)	0.15173 (10)	0.86374 (12)	0.0182 (4)
C2	0.4085 (2)	0.15979 (10)	0.95278 (13)	0.0200 (4)
H2A	0.3487	0.1928	0.9764	0.024*
C3	0.5000 (2)	0.11747 (11)	1.00590 (13)	0.0222 (4)
H3A	0.5039	0.1219	1.0670	0.027*
C4	0.5854 (2)	0.06882 (11)	0.96989 (13)	0.0207 (4)
H4A	0.6485	0.0401	1.0057	0.025*
C5	0.5764 (2)	0.06307 (10)	0.88014 (12)	0.0168 (4)
C6	0.3236 (2)	0.19449 (10)	0.79562 (13)	0.0191 (4)
C7	0.6578 (2)	0.01088 (10)	0.83018 (13)	0.0193 (4)
C8	0.3880 (2)	0.06609 (10)	0.52419 (12)	0.0170 (4)
C9	0.3753 (2)	0.07039 (11)	0.43455 (12)	0.0198 (4)
H9A	0.3063	0.0438	0.4003	0.024*
C10	0.4666 (2)	0.11477 (11)	0.39627 (13)	0.0227 (4)
H10A	0.4619	0.1176	0.3350	0.027*
C11	0.5645 (2)	0.15491 (11)	0.44730 (13)	0.0213 (4)
H11A	0.6256	0.1862	0.4219	0.026*
C12	0.5702 (2)	0.14777 (10)	0.53652 (12)	0.0167 (4)
C13	0.2970 (2)	0.02123 (10)	0.57769 (13)	0.0190 (4)
C14	0.6661 (2)	0.18976 (10)	0.60159 (13)	0.0189 (4)
N3	0.76898 (19)	0.21857 (9)	0.84229 (12)	0.0208 (3)
H3N	0.746 (3)	0.2148 (15)	0.7896 (19)	0.037 (8)*
C15	0.6925 (2)	0.26041 (10)	0.88993 (13)	0.0204 (4)
C16	0.5844 (2)	0.30294 (11)	0.85003 (15)	0.0255 (4)
H16A	0.5673	0.3048	0.7887	0.031*
C17	0.5043 (3)	0.34143 (11)	0.90007 (16)	0.0302 (5)
H17A	0.4304	0.3695	0.8731	0.036*
C18	0.5291 (3)	0.34042 (12)	0.99176 (16)	0.0321 (5)
H18A	0.4708	0.3671	1.0253	0.039*
C19	0.6361 (3)	0.30137 (13)	1.03178 (15)	0.0311 (5)
H19A	0.6538	0.3021	1.0931	0.037*
C20	0.7215 (2)	0.25951 (11)	0.98225 (13)	0.0238 (4)
C21	0.8285 (2)	0.21652 (12)	1.01903 (14)	0.0284 (5)
H21A	0.8496	0.2160	1.0801	0.034*
C22	0.9057 (2)	0.17410 (11)	0.96824 (14)	0.0263 (4)
C23	1.0150 (3)	0.12781 (14)	1.00362 (18)	0.0382 (6)
H23A	1.0393	0.1257	1.0644	0.046*
C24	1.0833 (3)	0.08721 (13)	0.9503 (2)	0.0426 (7)
H24A	1.1552	0.0565	0.9743	0.051*
C25	1.0502 (3)	0.08954 (12)	0.8598 (2)	0.0397 (6)
H25A	1.1008	0.0606	0.8241	0.048*
C26	0.9464 (2)	0.13276 (12)	0.82196 (17)	0.0309 (5)
H26A	0.9245	0.1338	0.7609	0.037*
C27	0.8730 (2)	0.17567 (11)	0.87635 (14)	0.0231 (4)
O1W	0.84765 (17)	0.32871 (9)	0.69335 (11)	0.0251 (3)
H1W1	0.815 (3)	0.3033 (16)	0.656 (2)	0.034 (8)*
H2W1	0.813 (4)	0.369 (2)	0.681 (2)	0.065 (11)*
O2W	0.96559 (18)	−0.06357 (9)	0.77630 (12)	0.0279 (3)
H1W2	0.909 (3)	−0.0493 (17)	0.808 (2)	0.045 (9)*
H2W2	0.940 (3)	−0.0417 (16)	0.729 (2)	0.039 (8)*
O3W	0.12555 (19)	0.31700 (9)	0.71080 (10)	0.0262 (3)
H1W3	0.037 (4)	0.3180 (18)	0.708 (2)	0.051 (9)*
H2W3	0.170 (5)	0.356 (2)	0.710 (3)	0.084 (14)*
O4W	0.25508 (19)	−0.05822 (9)	0.79542 (12)	0.0302 (4)
H1W4	0.170 (4)	−0.0602 (18)	0.791 (2)	0.049 (10)*
H2W4	0.268 (4)	−0.0327 (18)	0.755 (2)	0.050 (9)*
O5W	0.0430 (2)	−0.01699 (10)	0.37439 (12)	0.0322 (4)
H1W5	−0.029 (3)	−0.0086 (15)	0.3945 (19)	0.031 (7)*
H2W5	0.099 (4)	−0.016 (2)	0.421 (3)	0.066 (11)*

	U11	U22	U33	U12	U13	U23
Zn1	0.02513 (13)	0.02160 (13)	0.01244 (12)	−0.00038 (9)	0.00163 (9)	−0.00009 (8)
O1	0.0300 (8)	0.0264 (7)	0.0162 (7)	0.0090 (6)	0.0017 (6)	0.0001 (6)
O2	0.0248 (8)	0.0238 (7)	0.0208 (7)	0.0080 (6)	0.0026 (6)	−0.0013 (6)
O3	0.0293 (8)	0.0239 (7)	0.0149 (6)	0.0062 (6)	0.0015 (6)	−0.0021 (5)
O4	0.0279 (8)	0.0236 (7)	0.0227 (7)	0.0082 (6)	0.0012 (6)	0.0023 (6)
O5	0.0251 (7)	0.0262 (7)	0.0172 (7)	−0.0050 (6)	0.0018 (6)	0.0018 (6)
O6	0.0247 (8)	0.0276 (8)	0.0255 (8)	−0.0079 (6)	−0.0008 (6)	0.0004 (6)
O7	0.0266 (8)	0.0233 (7)	0.0152 (6)	−0.0052 (6)	0.0011 (5)	−0.0005 (5)
O8	0.0298 (8)	0.0273 (8)	0.0236 (7)	−0.0114 (6)	0.0030 (6)	−0.0003 (6)
N1	0.0194 (8)	0.0174 (7)	0.0132 (7)	−0.0023 (6)	0.0014 (6)	−0.0003 (6)
N2	0.0166 (8)	0.0164 (7)	0.0136 (7)	0.0014 (6)	0.0018 (6)	−0.0007 (6)
C1	0.0195 (9)	0.0177 (9)	0.0178 (9)	−0.0024 (7)	0.0030 (7)	−0.0010 (7)
C2	0.0231 (10)	0.0189 (9)	0.0187 (9)	−0.0006 (7)	0.0046 (7)	−0.0029 (7)
C3	0.0281 (10)	0.0245 (10)	0.0146 (9)	−0.0029 (8)	0.0050 (8)	−0.0033 (7)
C4	0.0255 (10)	0.0194 (9)	0.0168 (9)	−0.0012 (8)	0.0001 (7)	0.0021 (7)
C5	0.0172 (9)	0.0153 (8)	0.0178 (9)	−0.0021 (7)	0.0005 (7)	−0.0008 (7)
C6	0.0193 (9)	0.0192 (9)	0.0188 (9)	0.0004 (7)	0.0017 (7)	−0.0003 (7)
C7	0.0205 (9)	0.0185 (9)	0.0190 (9)	0.0001 (7)	0.0020 (7)	−0.0004 (7)
C8	0.0181 (9)	0.0151 (8)	0.0178 (9)	0.0025 (7)	0.0014 (7)	−0.0006 (7)
C9	0.0212 (10)	0.0210 (9)	0.0168 (9)	−0.0002 (7)	−0.0007 (7)	−0.0027 (7)
C10	0.0277 (11)	0.0273 (10)	0.0130 (9)	0.0003 (8)	0.0015 (8)	0.0003 (7)
C11	0.0247 (10)	0.0221 (9)	0.0176 (9)	−0.0013 (8)	0.0045 (8)	0.0023 (7)
C12	0.0173 (9)	0.0161 (8)	0.0164 (8)	0.0017 (7)	0.0004 (7)	0.0000 (7)
C13	0.0200 (9)	0.0170 (9)	0.0203 (9)	0.0007 (7)	0.0031 (7)	0.0007 (7)
C14	0.0192 (9)	0.0177 (9)	0.0197 (9)	−0.0009 (7)	0.0014 (7)	−0.0015 (7)
N3	0.0238 (9)	0.0194 (8)	0.0183 (8)	−0.0032 (7)	−0.0024 (7)	0.0010 (6)
C15	0.0220 (10)	0.0191 (9)	0.0197 (9)	−0.0058 (7)	0.0007 (7)	0.0009 (7)
C16	0.0284 (11)	0.0206 (10)	0.0267 (10)	−0.0008 (8)	−0.0011 (8)	0.0020 (8)
C17	0.0298 (12)	0.0193 (10)	0.0418 (13)	−0.0009 (8)	0.0054 (10)	0.0004 (9)
C18	0.0361 (13)	0.0248 (11)	0.0375 (13)	−0.0055 (9)	0.0132 (10)	−0.0072 (9)
C19	0.0388 (13)	0.0325 (12)	0.0233 (10)	−0.0139 (10)	0.0084 (9)	−0.0064 (9)
C20	0.0277 (11)	0.0225 (10)	0.0206 (10)	−0.0095 (8)	0.0006 (8)	0.0002 (8)
C21	0.0327 (12)	0.0317 (11)	0.0193 (10)	−0.0119 (9)	−0.0049 (9)	0.0051 (8)
C22	0.0240 (10)	0.0238 (10)	0.0289 (11)	−0.0070 (8)	−0.0081 (8)	0.0083 (8)
C23	0.0312 (13)	0.0341 (13)	0.0452 (14)	−0.0058 (10)	−0.0146 (11)	0.0147 (11)
C24	0.0259 (12)	0.0279 (12)	0.070 (2)	0.0008 (10)	−0.0132 (12)	0.0085 (12)
C25	0.0268 (12)	0.0219 (11)	0.0692 (19)	−0.0018 (9)	0.0003 (12)	−0.0086 (11)
C26	0.0247 (11)	0.0251 (11)	0.0424 (13)	−0.0023 (9)	0.0014 (10)	−0.0060 (9)
C27	0.0213 (10)	0.0190 (9)	0.0280 (10)	−0.0059 (8)	−0.0028 (8)	0.0014 (8)
O1W	0.0268 (8)	0.0240 (8)	0.0233 (8)	−0.0020 (6)	−0.0036 (6)	−0.0009 (6)
O2W	0.0274 (8)	0.0299 (8)	0.0273 (8)	0.0023 (7)	0.0068 (7)	−0.0007 (7)
O3W	0.0239 (8)	0.0250 (8)	0.0290 (8)	0.0035 (6)	−0.0010 (6)	−0.0002 (6)
O4W	0.0274 (9)	0.0298 (9)	0.0341 (9)	0.0025 (7)	0.0064 (7)	0.0095 (7)
O5W	0.0264 (9)	0.0412 (10)	0.0288 (9)	−0.0026 (7)	0.0019 (7)	0.0048 (7)

Zn1—N2	2.0011 (16)	N3—C27	1.352 (3)
Zn1—N1	2.0238 (16)	N3—C15	1.354 (3)
Zn1—O3	2.0864 (14)	N3—H3N	0.83 (3)
Zn1—O5	2.1443 (15)	C15—C16	1.407 (3)
Zn1—O7	2.2100 (14)	C15—C20	1.433 (3)
Zn1—O1	2.3406 (14)	C16—C17	1.362 (3)
O1—C6	1.230 (2)	C16—H16A	0.9500
O2—C6	1.292 (2)	C17—C18	1.420 (4)
O2—H2O	0.87 (5)	C17—H17A	0.9500
O3—C7	1.267 (2)	C18—C19	1.363 (4)
O4—C7	1.246 (2)	C18—H18A	0.9500
O5—C13	1.270 (2)	C19—C20	1.425 (3)
O6—C13	1.240 (2)	C19—H19A	0.9500
O7—C14	1.275 (2)	C20—C21	1.387 (3)
O8—C14	1.234 (2)	C21—C22	1.395 (3)
N1—C5	1.334 (2)	C21—H21A	0.9500
N1—C1	1.335 (2)	C22—C27	1.430 (3)
N2—C12	1.333 (2)	C22—C23	1.433 (3)
N2—C8	1.336 (2)	C23—C24	1.351 (4)
C1—C2	1.392 (3)	C23—H23A	0.9500
C1—C6	1.503 (3)	C24—C25	1.411 (4)
C2—C3	1.395 (3)	C24—H24A	0.9500
C2—H2A	0.9500	C25—C26	1.374 (4)
C3—C4	1.391 (3)	C25—H25A	0.9500
C3—H3A	0.9500	C26—C27	1.414 (3)
C4—C5	1.393 (3)	C26—H26A	0.9500
C4—H4A	0.9500	O1W—H1W1	0.79 (3)
C5—C7	1.524 (3)	O1W—H2W1	0.84 (4)
C8—C9	1.388 (3)	O2W—H1W2	0.82 (3)
C8—C13	1.527 (3)	O2W—H2W2	0.85 (3)
C9—C10	1.394 (3)	O3W—H1W3	0.85 (4)
C9—H9A	0.9500	O3W—H2W3	0.85 (5)
C10—C11	1.392 (3)	O4W—H1W4	0.82 (4)
C10—H10A	0.9500	O4W—H2W4	0.81 (4)
C11—C12	1.389 (3)	O5W—H1W5	0.80 (3)
C11—H11A	0.9500	O5W—H2W5	0.86 (4)
C12—C14	1.520 (3)
N2—Zn1—N1	167.38 (7)	C10—C11—H11A	121.0
N2—Zn1—O3	113.11 (6)	N2—C12—C11	121.08 (18)
N1—Zn1—O3	79.15 (6)	N2—C12—C14	114.08 (16)
N2—Zn1—O5	77.60 (6)	C11—C12—C14	124.79 (18)
N1—Zn1—O5	104.68 (6)	O6—C13—O5	126.33 (19)
O3—Zn1—O5	96.92 (6)	O6—C13—C8	118.50 (17)
N2—Zn1—O7	76.47 (6)	O5—C13—C8	115.16 (17)
N1—Zn1—O7	99.78 (6)	O8—C14—O7	126.56 (18)
O3—Zn1—O7	96.89 (6)	O8—C14—C12	118.05 (17)
O5—Zn1—O7	153.75 (5)	O7—C14—C12	115.37 (17)
N2—Zn1—O1	94.29 (6)	C27—N3—C15	124.05 (19)
N1—Zn1—O1	73.40 (6)	C27—N3—H3N	116 (2)
O3—Zn1—O1	152.55 (5)	C15—N3—H3N	119 (2)
O5—Zn1—O1	90.37 (6)	N3—C15—C16	120.89 (19)
O7—Zn1—O1	87.57 (6)	N3—C15—C20	118.76 (19)
C6—O1—Zn1	111.93 (13)	C16—C15—C20	120.3 (2)
C6—O2—H2O	106 (3)	C17—C16—C15	119.4 (2)
C7—O3—Zn1	115.21 (12)	C17—C16—H16A	120.3
C13—O5—Zn1	115.26 (12)	C15—C16—H16A	120.3
C14—O7—Zn1	114.18 (12)	C16—C17—C18	121.4 (2)
C5—N1—C1	121.40 (17)	C16—C17—H17A	119.3
C5—N1—Zn1	115.70 (13)	C18—C17—H17A	119.3
C1—N1—Zn1	122.84 (13)	C19—C18—C17	120.3 (2)
C12—N2—C8	121.65 (16)	C19—C18—H18A	119.9
C12—N2—Zn1	119.81 (13)	C17—C18—H18A	119.9
C8—N2—Zn1	118.53 (13)	C18—C19—C20	120.4 (2)
N1—C1—C2	121.71 (18)	C18—C19—H19A	119.8
N1—C1—C6	112.49 (16)	C20—C19—H19A	119.8
C2—C1—C6	125.77 (18)	C21—C20—C19	123.3 (2)
C1—C2—C3	117.39 (18)	C21—C20—C15	118.5 (2)
C1—C2—H2A	121.3	C19—C20—C15	118.2 (2)
C3—C2—H2A	121.3	C20—C21—C22	121.4 (2)
C4—C3—C2	120.34 (18)	C20—C21—H21A	119.3
C4—C3—H3A	119.8	C22—C21—H21A	119.3
C2—C3—H3A	119.8	C21—C22—C27	118.6 (2)
C3—C4—C5	118.55 (18)	C21—C22—C23	123.2 (2)
C3—C4—H4A	120.7	C27—C22—C23	118.1 (2)
C5—C4—H4A	120.7	C24—C23—C22	119.9 (2)
N1—C5—C4	120.58 (18)	C24—C23—H23A	120.1
N1—C5—C7	113.94 (16)	C22—C23—H23A	120.1
C4—C5—C7	125.47 (18)	C23—C24—C25	121.4 (2)
O1—C6—O2	125.66 (19)	C23—C24—H24A	119.3
O1—C6—C1	119.23 (18)	C25—C24—H24A	119.3
O2—C6—C1	115.09 (17)	C26—C25—C24	121.5 (3)
O4—C7—O3	126.57 (19)	C26—C25—H25A	119.2
O4—C7—C5	117.59 (17)	C24—C25—H25A	119.2
O3—C7—C5	115.84 (17)	C25—C26—C27	118.2 (2)
N2—C8—C9	120.81 (18)	C25—C26—H26A	120.9
N2—C8—C13	113.42 (16)	C27—C26—H26A	120.9
C9—C8—C13	125.76 (18)	N3—C27—C26	120.4 (2)
C8—C9—C10	118.12 (18)	N3—C27—C22	118.6 (2)
C8—C9—H9A	120.9	C26—C27—C22	120.9 (2)
C10—C9—H9A	120.9	H1W1—O1W—H2W1	105 (3)
C11—C10—C9	120.35 (18)	H1W2—O2W—H2W2	102 (3)
C11—C10—H10A	119.8	H1W3—O3W—H2W3	119 (4)
C9—C10—H10A	119.8	H1W4—O4W—H2W4	101 (3)
C12—C11—C10	117.95 (19)	H1W5—O5W—H2W5	99 (3)
C12—C11—H11A	121.0
N2—Zn1—O1—C6	−179.71 (14)	Zn1—O3—C7—C5	−1.0 (2)
N1—Zn1—O1—C6	−2.52 (14)	N1—C5—C7—O4	−175.43 (18)
O3—Zn1—O1—C6	−3.2 (2)	C4—C5—C7—O4	3.6 (3)
O5—Zn1—O1—C6	102.70 (14)	N1—C5—C7—O3	3.8 (3)
O7—Zn1—O1—C6	−103.48 (14)	C4—C5—C7—O3	−177.18 (19)
N2—Zn1—O3—C7	175.78 (14)	C12—N2—C8—C9	1.3 (3)
N1—Zn1—O3—C7	−1.10 (14)	Zn1—N2—C8—C9	−179.21 (14)
O5—Zn1—O3—C7	−104.79 (15)	C12—N2—C8—C13	−177.72 (16)
O7—Zn1—O3—C7	97.59 (14)	Zn1—N2—C8—C13	1.8 (2)
O1—Zn1—O3—C7	−0.5 (2)	N2—C8—C9—C10	0.4 (3)
N2—Zn1—O5—C13	0.03 (14)	C13—C8—C9—C10	179.29 (18)
N1—Zn1—O5—C13	167.26 (14)	C8—C9—C10—C11	−1.8 (3)
O3—Zn1—O5—C13	−112.19 (14)	C9—C10—C11—C12	1.6 (3)
O7—Zn1—O5—C13	9.1 (2)	C8—N2—C12—C11	−1.5 (3)
O1—Zn1—O5—C13	94.34 (14)	Zn1—N2—C12—C11	178.99 (14)
N2—Zn1—O7—C14	−1.10 (13)	C8—N2—C12—C14	176.01 (16)
N1—Zn1—O7—C14	−168.79 (14)	Zn1—N2—C12—C14	−3.5 (2)
O3—Zn1—O7—C14	111.08 (14)	C10—C11—C12—N2	0.0 (3)
O5—Zn1—O7—C14	−10.2 (2)	C10—C11—C12—C14	−177.22 (19)
O1—Zn1—O7—C14	−96.10 (14)	Zn1—O5—C13—O6	−178.26 (17)
N2—Zn1—N1—C5	−163.5 (3)	Zn1—O5—C13—C8	0.8 (2)
O3—Zn1—N1—C5	3.30 (13)	N2—C8—C13—O6	177.49 (17)
O5—Zn1—N1—C5	97.69 (14)	C9—C8—C13—O6	−1.5 (3)
O7—Zn1—N1—C5	−91.92 (14)	N2—C8—C13—O5	−1.7 (2)
O1—Zn1—N1—C5	−176.39 (15)	C9—C8—C13—O5	179.34 (19)
N2—Zn1—N1—C1	13.6 (4)	Zn1—O7—C14—O8	177.92 (17)
O3—Zn1—N1—C1	−179.60 (16)	Zn1—O7—C14—C12	−0.3 (2)
O5—Zn1—N1—C1	−85.21 (15)	N2—C12—C14—O8	−176.04 (18)
O7—Zn1—N1—C1	85.18 (15)	C11—C12—C14—O8	1.4 (3)
O1—Zn1—N1—C1	0.71 (14)	N2—C12—C14—O7	2.3 (2)
N1—Zn1—N2—C12	76.6 (3)	C11—C12—C14—O7	179.78 (19)
O3—Zn1—N2—C12	−89.25 (15)	C27—N3—C15—C16	−179.05 (19)
O5—Zn1—N2—C12	178.44 (15)	C27—N3—C15—C20	−0.4 (3)
O7—Zn1—N2—C12	2.55 (14)	N3—C15—C16—C17	176.4 (2)
O1—Zn1—N2—C12	89.01 (14)	C20—C15—C16—C17	−2.2 (3)
N1—Zn1—N2—C8	−102.9 (3)	C15—C16—C17—C18	1.0 (3)
O3—Zn1—N2—C8	91.25 (14)	C16—C17—C18—C19	1.1 (3)
O5—Zn1—N2—C8	−1.06 (13)	C17—C18—C19—C20	−1.9 (3)
O7—Zn1—N2—C8	−176.94 (15)	C18—C19—C20—C21	−177.4 (2)
O1—Zn1—N2—C8	−90.49 (14)	C18—C19—C20—C15	0.7 (3)
C5—N1—C1—C2	−0.5 (3)	N3—C15—C20—C21	1.0 (3)
Zn1—N1—C1—C2	−177.47 (14)	C16—C15—C20—C21	179.63 (19)
C5—N1—C1—C6	177.80 (17)	N3—C15—C20—C19	−177.22 (18)
Zn1—N1—C1—C6	0.9 (2)	C16—C15—C20—C19	1.4 (3)
N1—C1—C2—C3	1.4 (3)	C19—C20—C21—C22	177.2 (2)
C6—C1—C2—C3	−176.73 (19)	C15—C20—C21—C22	−0.9 (3)
C1—C2—C3—C4	−0.8 (3)	C20—C21—C22—C27	0.2 (3)
C2—C3—C4—C5	−0.6 (3)	C20—C21—C22—C23	−178.6 (2)
C1—N1—C5—C4	−0.9 (3)	C21—C22—C23—C24	178.6 (2)
Zn1—N1—C5—C4	176.22 (14)	C27—C22—C23—C24	−0.2 (3)
C1—N1—C5—C7	178.16 (17)	C22—C23—C24—C25	0.4 (4)
Zn1—N1—C5—C7	−4.7 (2)	C23—C24—C25—C26	−0.5 (4)
C3—C4—C5—N1	1.5 (3)	C24—C25—C26—C27	0.3 (4)
C3—C4—C5—C7	−177.51 (19)	C15—N3—C27—C26	178.98 (19)
Zn1—O1—C6—O2	−177.61 (16)	C15—N3—C27—C22	−0.3 (3)
Zn1—O1—C6—C1	3.8 (2)	C25—C26—C27—N3	−179.3 (2)
N1—C1—C6—O1	−3.4 (3)	C25—C26—C27—C22	−0.1 (3)
C2—C1—C6—O1	174.9 (2)	C21—C22—C27—N3	0.4 (3)
N1—C1—C6—O2	177.91 (17)	C23—C22—C27—N3	179.27 (19)
C2—C1—C6—O2	−3.8 (3)	C21—C22—C27—C26	−178.9 (2)
Zn1—O3—C7—O4	178.12 (17)	C23—C22—C27—C26	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3W	0.88 (4)	1.61 (4)	2.465 (2)	166 (4)
N3—H3N···O7	0.83 (3)	1.96 (3)	2.752 (2)	159 (3)
O1W—H1W1···O8	0.79 (3)	1.91 (3)	2.696 (2)	174 (3)
O1W—H2W1···O4i	0.85 (4)	2.07 (4)	2.901 (2)	165 (3)
O2W—H1W2···O4	0.82 (3)	2.07 (3)	2.873 (2)	166 (3)
O2W—H2W2···O5Wii	0.86 (3)	1.98 (3)	2.791 (3)	158 (3)
O3W—H1W3···O1Wiii	0.85 (4)	1.82 (4)	2.665 (2)	173 (3)
O3W—H2W3···O4Wiv	0.85 (4)	1.78 (4)	2.636 (2)	174 (5)
O4W—H1W4···O2Wiii	0.81 (4)	1.95 (4)	2.768 (3)	178 (3)
O4W—H2W4···O5	0.81 (3)	1.98 (3)	2.788 (2)	172 (4)
O5W—H1W5···O6v	0.80 (3)	2.08 (3)	2.880 (2)	173 (3)
O5W—H2W5···O6	0.86 (4)	1.99 (5)	2.838 (2)	171 (4)

Table 1

Selected bond lengths (Å)

Zn1—N2	2.0011 (16)
Zn1—N1	2.0238 (16)
Zn1—O3	2.0864 (14)
Zn1—O5	2.1443 (15)
Zn1—O7	2.2100 (14)
Zn1—O1	2.3406 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3W	0.88 (4)	1.61 (4)	2.465 (2)	166 (4)
N3—H3N⋯O7	0.83 (3)	1.96 (3)	2.752 (2)	159 (3)
O1W—H1W1⋯O8	0.79 (3)	1.91 (3)	2.696 (2)	174 (3)
O1W—H2W1⋯O4i	0.85 (4)	2.07 (4)	2.901 (2)	165 (3)
O2W—H1W2⋯O4	0.82 (3)	2.07 (3)	2.873 (2)	166 (3)
O2W—H2W2⋯O5Wii	0.86 (3)	1.98 (3)	2.791 (3)	158 (3)
O3W—H1W3⋯O1Wiii	0.85 (4)	1.82 (4)	2.665 (2)	173 (3)
O3W—H2W3⋯O4Wiv	0.85 (4)	1.78 (4)	2.636 (2)	174 (5)
O4W—H1W4⋯O2Wiii	0.81 (4)	1.95 (4)	2.768 (3)	178 (3)
O4W—H2W4⋯O5	0.81 (3)	1.98 (3)	2.788 (2)	172 (4)
O5W—H1W5⋯O6v	0.80 (3)	2.08 (3)	2.880 (2)	173 (3)
O5W—H2W5⋯O6	0.86 (4)	1.99 (5)	2.838 (2)	171 (4)

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