Poly[[diaqua-bis-{μ-4-[6-(4-carboxyphenyl)-4,4'-bipyridin-2-yl]benzoato-κ(2)O:N(4')}zinc] dimethyl-formamide tetra-solvate].

In the title compound, {[Zn(C(24)H(15)N(2)O(4))(2)(H(2)O)(2)]·4C(3)H(7)NO}(n), the Zn(II) ion is located on an inversion center and is six-coordinated by two N atoms from two ligands, two carboxylate O atoms from two other symmetry-related ligands and two O atoms from two water mol-ecules, furnishing a slightly distorted octa-hedral geometry. The Zn(II) atoms are connected by the bridging ligands into a layer parallel to (101). O-H⋯O hydrogen bonds link the layers and the dimethyl-formamide solvent mol-ecules. π-π inter-actions between the pyridine and benzene rings [centroid-centroid distances = 3.7428 (17) and 3.7619 (17) Å] and intra-layer O-H⋯O hydrogen bonds are also present.

Related literature

For the design of transition metal complexes with supra­molecular structures, see: Li et al. (2011 ▶); Wang et al. (2010 ▶); Yang et al. (2007 ▶). For related structures, see: Song et al. (2012 ▶).

Experimental

Crystal data

[Zn(C24H15N2O4)2(H2O)2]·4C3H7NO

M = 1184.57

Monoclinic,

a = 7.4744 (5) Å

b = 17.7122 (13) Å

c = 21.4993 (15) Å

β = 95.075 (1)°

V = 2835.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.839, T max = 0.915

15534 measured reflections

5606 independent reflections

3804 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.158

S = 1.05

5606 reflections

385 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043838/hy2597sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043838/hy2597Isup2.hkl

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

[Zn(C24H15N2O4)2(H2O)2]·4C3H7NO	F(000) = 1240
Mr = 1184.57	Dx = 1.388 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5607 reflections
a = 7.4744 (5) Å	θ = 1.0–26.1°
b = 17.7122 (13) Å	µ = 0.51 mm−1
c = 21.4993 (15) Å	T = 293 K
β = 95.075 (1)°	Block, colorless
V = 2835.1 (3) Å3	0.25 × 0.22 × 0.19 mm
Z = 2

Bruker APEXII CCD diffractometer	5606 independent reflections
Radiation source: fine-focus sealed tube	3804 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
Tmin = 0.839, Tmax = 0.915	k = −16→21
15534 measured reflections	l = −26→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.078P)2 + 1.0747P] where P = (Fo2 + 2Fc2)/3
5606 reflections	(Δ/σ)max < 0.001
385 parameters	Δρmax = 0.40 e Å−3
3 restraints	Δρmin = −0.35 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.0000	0.5000	0.0000	0.03205 (18)
C1	0.6503 (5)	0.73356 (19)	0.63443 (16)	0.0392 (8)
C2	0.6897 (4)	0.66640 (18)	0.59720 (14)	0.0331 (7)
C3	0.6424 (4)	0.59554 (18)	0.61726 (15)	0.0347 (8)
H3	0.5935	0.5901	0.6553	0.042*
C4	0.6676 (4)	0.53241 (19)	0.58068 (14)	0.0318 (7)
H4	0.6355	0.4850	0.5945	0.038*
C5	0.7403 (4)	0.53927 (17)	0.52353 (13)	0.0266 (6)
C6	0.7865 (4)	0.61109 (18)	0.50425 (15)	0.0317 (7)
H6	0.8333	0.6170	0.4659	0.038*
C7	0.7642 (4)	0.67359 (18)	0.54074 (15)	0.0336 (7)
H7	0.7993	0.7209	0.5275	0.040*
C8	0.7645 (4)	0.47318 (18)	0.48218 (14)	0.0275 (7)
C9	0.7387 (4)	0.39894 (17)	0.50138 (14)	0.0275 (7)
H9	0.7094	0.3891	0.5417	0.033*
C10	0.7572 (4)	0.33962 (17)	0.45977 (13)	0.0264 (6)
C11	0.8034 (4)	0.35839 (17)	0.40001 (13)	0.0288 (7)
H11	0.8162	0.3207	0.3706	0.035*
C12	0.8302 (4)	0.43340 (17)	0.38481 (13)	0.0263 (6)
C13	0.8806 (4)	0.45519 (17)	0.32174 (13)	0.0278 (7)
C14	0.8268 (4)	0.41227 (18)	0.26902 (14)	0.0329 (7)
H14	0.7549	0.3700	0.2729	0.039*
C15	0.8791 (4)	0.43189 (18)	0.21099 (14)	0.0326 (7)
H15	0.8420	0.4028	0.1762	0.039*
C16	0.9868 (4)	0.49489 (17)	0.20442 (14)	0.0283 (7)
C17	1.0387 (4)	0.53839 (18)	0.25678 (14)	0.0321 (7)
H17	1.1100	0.5809	0.2528	0.038*
C18	0.9856 (4)	0.51921 (18)	0.31450 (14)	0.0324 (7)
H18	1.0202	0.5492	0.3490	0.039*
C19	1.0453 (5)	0.51556 (17)	0.14145 (15)	0.0333 (8)
C20	0.7223 (4)	0.26062 (17)	0.47603 (13)	0.0266 (6)
C21	0.7949 (4)	0.19986 (18)	0.44509 (14)	0.0344 (8)
H21	0.8797	0.2085	0.4168	0.041*
C22	0.7410 (4)	0.12758 (18)	0.45651 (14)	0.0348 (7)
H22	0.7923	0.0882	0.4357	0.042*
C23	0.5550 (4)	0.16840 (18)	0.52842 (14)	0.0326 (7)
H23	0.4745	0.1578	0.5578	0.039*
C24	0.6034 (4)	0.24235 (17)	0.52010 (13)	0.0292 (7)
H24	0.5568	0.2802	0.5439	0.035*
C25	0.5183 (11)	0.7258 (3)	0.2575 (3)	0.128 (3)
H25A	0.5527	0.7407	0.2173	0.192*
H25B	0.5922	0.7515	0.2896	0.192*
H25C	0.3947	0.7387	0.2606	0.192*
C26	0.5986 (7)	0.6048 (3)	0.2118 (2)	0.0877 (17)
H26A	0.6200	0.6397	0.1791	0.132*
H26B	0.5067	0.5697	0.1970	0.132*
H26C	0.7073	0.5778	0.2243	0.132*
C27	0.5016 (7)	0.6134 (3)	0.3160 (2)	0.0726 (13)
H27	0.5261	0.5620	0.3197	0.087*
C28	0.8396 (6)	0.1388 (3)	0.6757 (2)	0.0836 (16)
H28A	0.8060	0.1752	0.7056	0.125*
H28B	0.8962	0.0964	0.6971	0.125*
H28C	0.7344	0.1222	0.6506	0.125*
C29	1.0019 (7)	0.2524 (3)	0.6437 (2)	0.0759 (14)
H29A	0.9434	0.2711	0.6786	0.114*
H29B	0.9580	0.2792	0.6066	0.114*
H29C	1.1291	0.2599	0.6513	0.114*
C30	1.0301 (5)	0.1338 (2)	0.59015 (18)	0.0506 (10)
H30	0.9951	0.0835	0.5854	0.061*
N1	0.8119 (3)	0.49033 (14)	0.42511 (11)	0.0278 (6)
N2	0.6181 (3)	0.11067 (14)	0.49621 (11)	0.0313 (6)
N3	0.5410 (4)	0.64597 (18)	0.26498 (14)	0.0501 (8)
N4	0.9645 (4)	0.1733 (2)	0.63570 (15)	0.0520 (8)
O1	0.9686 (3)	0.48245 (12)	0.09483 (9)	0.0361 (6)
O2	1.1689 (3)	0.56380 (13)	0.13980 (10)	0.0432 (6)
O3	0.7257 (4)	0.79565 (15)	0.61423 (13)	0.0569 (7)
H3A	0.683 (6)	0.8386 (13)	0.624 (2)	0.085*
O4	0.5576 (4)	0.73346 (15)	0.67822 (12)	0.0544 (7)
O5	0.4357 (5)	0.64314 (19)	0.35968 (14)	0.0839 (11)
O6	1.1334 (4)	0.15890 (17)	0.55402 (13)	0.0590 (8)
O1W	1.2630 (3)	0.54461 (14)	0.02156 (11)	0.0416 (6)
H1A	1.299 (5)	0.5844 (14)	0.0047 (18)	0.062*
H1B	1.278 (5)	0.559 (2)	0.0592 (8)	0.062*

	U11	U22	U33	U12	U13	U23
Zn1	0.0519 (3)	0.0240 (3)	0.0219 (3)	0.0006 (2)	0.0128 (2)	0.0000 (2)
C1	0.050 (2)	0.033 (2)	0.0353 (19)	0.0030 (16)	0.0075 (16)	−0.0027 (15)
C2	0.0362 (17)	0.0336 (18)	0.0293 (17)	0.0046 (14)	0.0013 (14)	−0.0048 (14)
C3	0.0421 (18)	0.0354 (19)	0.0278 (17)	0.0034 (15)	0.0100 (14)	0.0005 (14)
C4	0.0413 (18)	0.0293 (17)	0.0254 (16)	0.0013 (14)	0.0066 (14)	0.0021 (13)
C5	0.0270 (15)	0.0278 (17)	0.0248 (16)	0.0007 (13)	0.0013 (12)	0.0009 (12)
C6	0.0361 (17)	0.0308 (18)	0.0291 (17)	−0.0009 (14)	0.0081 (14)	−0.0001 (13)
C7	0.0378 (18)	0.0275 (17)	0.0360 (18)	−0.0006 (14)	0.0060 (15)	0.0006 (14)
C8	0.0272 (15)	0.0292 (16)	0.0266 (16)	−0.0020 (13)	0.0054 (13)	−0.0014 (13)
C9	0.0295 (16)	0.0309 (17)	0.0228 (15)	−0.0004 (13)	0.0057 (13)	0.0016 (12)
C10	0.0298 (15)	0.0284 (16)	0.0214 (15)	0.0015 (13)	0.0046 (12)	0.0016 (12)
C11	0.0371 (17)	0.0282 (17)	0.0217 (15)	0.0012 (13)	0.0063 (13)	−0.0005 (12)
C12	0.0317 (16)	0.0287 (17)	0.0187 (14)	−0.0002 (13)	0.0039 (12)	0.0017 (12)
C13	0.0338 (16)	0.0274 (17)	0.0229 (15)	0.0020 (13)	0.0074 (13)	0.0034 (12)
C14	0.0452 (19)	0.0290 (17)	0.0261 (16)	−0.0059 (14)	0.0118 (14)	0.0008 (13)
C15	0.0480 (19)	0.0296 (18)	0.0211 (15)	0.0010 (14)	0.0075 (14)	0.0008 (13)
C16	0.0390 (17)	0.0244 (16)	0.0226 (15)	0.0038 (13)	0.0102 (13)	0.0026 (12)
C17	0.0437 (18)	0.0272 (17)	0.0263 (16)	−0.0049 (14)	0.0081 (14)	0.0032 (13)
C18	0.0448 (18)	0.0322 (18)	0.0209 (16)	−0.0038 (14)	0.0065 (14)	−0.0012 (12)
C19	0.0482 (19)	0.0265 (18)	0.0268 (17)	0.0052 (15)	0.0115 (15)	0.0043 (13)
C20	0.0333 (16)	0.0241 (16)	0.0229 (15)	0.0006 (13)	0.0054 (12)	0.0001 (12)
C21	0.0439 (19)	0.0327 (18)	0.0286 (17)	−0.0002 (15)	0.0144 (15)	0.0001 (13)
C22	0.0481 (19)	0.0285 (17)	0.0296 (17)	0.0029 (15)	0.0132 (15)	−0.0025 (13)
C23	0.0461 (19)	0.0294 (17)	0.0240 (16)	0.0000 (14)	0.0124 (14)	0.0014 (13)
C24	0.0406 (17)	0.0264 (16)	0.0213 (15)	−0.0009 (13)	0.0063 (13)	−0.0003 (12)
C25	0.226 (8)	0.052 (4)	0.107 (5)	0.005 (4)	0.016 (5)	0.023 (3)
C26	0.084 (3)	0.127 (5)	0.055 (3)	0.038 (3)	0.025 (3)	0.002 (3)
C27	0.103 (4)	0.055 (3)	0.064 (3)	0.011 (3)	0.032 (3)	0.009 (2)
C28	0.078 (3)	0.116 (5)	0.061 (3)	−0.027 (3)	0.031 (3)	−0.016 (3)
C29	0.092 (3)	0.065 (3)	0.073 (3)	0.005 (3)	0.020 (3)	−0.018 (2)
C30	0.054 (2)	0.051 (2)	0.047 (2)	0.0043 (19)	0.0038 (19)	−0.0033 (18)
N1	0.0320 (13)	0.0289 (15)	0.0235 (13)	−0.0014 (11)	0.0069 (11)	0.0025 (10)
N2	0.0468 (16)	0.0251 (14)	0.0232 (13)	−0.0013 (12)	0.0103 (12)	0.0005 (10)
N3	0.059 (2)	0.051 (2)	0.0425 (18)	0.0119 (16)	0.0188 (15)	0.0105 (15)
N4	0.0484 (18)	0.063 (2)	0.0460 (19)	0.0022 (16)	0.0137 (15)	−0.0078 (16)
O1	0.0617 (15)	0.0290 (13)	0.0190 (11)	−0.0026 (10)	0.0118 (11)	−0.0013 (9)
O2	0.0644 (16)	0.0364 (14)	0.0311 (12)	−0.0112 (12)	0.0170 (11)	0.0010 (10)
O3	0.0751 (19)	0.0377 (16)	0.0612 (17)	0.0008 (14)	0.0256 (15)	−0.0095 (13)
O4	0.0735 (18)	0.0479 (17)	0.0439 (15)	0.0008 (14)	0.0177 (14)	−0.0080 (12)
O5	0.134 (3)	0.071 (2)	0.0527 (18)	0.008 (2)	0.044 (2)	−0.0085 (16)
O6	0.0602 (17)	0.065 (2)	0.0548 (17)	0.0113 (14)	0.0242 (14)	−0.0028 (14)
O1W	0.0544 (15)	0.0381 (15)	0.0345 (13)	−0.0061 (12)	0.0165 (12)	−0.0018 (11)

Zn1—O1	2.096 (2)	C18—H18	0.9300
Zn1—O1i	2.096 (2)	C19—O1	1.255 (4)
Zn1—O1W	2.131 (3)	C19—O2	1.261 (4)
Zn1—O1Wi	2.131 (3)	C20—C24	1.393 (4)
Zn1—N2ii	2.154 (3)	C20—C21	1.400 (4)
Zn1—N2iii	2.154 (3)	C21—C22	1.371 (4)
C1—O4	1.217 (4)	C21—H21	0.9300
C1—O3	1.326 (4)	C22—N2	1.342 (4)
C1—C2	1.478 (4)	C22—H22	0.9300
C2—C3	1.383 (5)	C23—N2	1.344 (4)
C2—C7	1.385 (4)	C23—C24	1.375 (4)
C3—C4	1.389 (4)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.392 (4)	C25—N3	1.431 (6)
C4—H4	0.9300	C25—H25A	0.9600
C5—C6	1.391 (4)	C25—H25B	0.9600
C5—C8	1.490 (4)	C25—H25C	0.9600
C6—C7	1.375 (4)	C26—N3	1.453 (5)
C6—H6	0.9300	C26—H26A	0.9600
C7—H7	0.9300	C26—H26B	0.9600
C8—N1	1.342 (4)	C26—H26C	0.9600
C8—C9	1.397 (4)	C27—O5	1.217 (5)
C9—C10	1.395 (4)	C27—N3	1.297 (5)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.400 (4)	C28—N4	1.458 (5)
C10—C20	1.471 (4)	C28—H28A	0.9600
C11—C12	1.387 (4)	C28—H28B	0.9600
C11—H11	0.9300	C28—H28C	0.9600
C12—N1	1.344 (4)	C29—N4	1.436 (5)
C12—C13	1.490 (4)	C29—H29A	0.9600
C13—C14	1.394 (4)	C29—H29B	0.9600
C13—C18	1.396 (4)	C29—H29C	0.9600
C14—C15	1.384 (4)	C30—O6	1.226 (4)
C14—H14	0.9300	C30—N4	1.333 (5)
C15—C16	1.390 (4)	C30—H30	0.9300
C15—H15	0.9300	N2—Zn1iv	2.154 (3)
C16—C17	1.391 (4)	O3—H3A	0.86 (1)
C16—C19	1.504 (4)	O1W—H1A	0.85 (1)
C17—C18	1.378 (4)	O1W—H1B	0.85 (1)
C17—H17	0.9300
O1—Zn1—O1i	180.0	C17—C18—C13	120.7 (3)
O1—Zn1—O1W	91.38 (9)	C17—C18—H18	119.7
O1i—Zn1—O1W	88.62 (9)	C13—C18—H18	119.7
O1—Zn1—O1Wi	88.62 (9)	O1—C19—O2	125.3 (3)
O1i—Zn1—O1Wi	91.38 (9)	O1—C19—C16	117.1 (3)
O1W—Zn1—O1Wi	180.0	O2—C19—C16	117.5 (3)
O1—Zn1—N2ii	89.05 (9)	C24—C20—C21	116.2 (3)
O1i—Zn1—N2ii	90.95 (9)	C24—C20—C10	121.3 (3)
O1W—Zn1—N2ii	88.43 (10)	C21—C20—C10	122.3 (3)
O1Wi—Zn1—N2ii	91.57 (10)	C22—C21—C20	120.1 (3)
O1—Zn1—N2iii	90.95 (9)	C22—C21—H21	120.0
O1i—Zn1—N2iii	89.05 (9)	C20—C21—H21	120.0
O1W—Zn1—N2iii	91.57 (10)	N2—C22—C21	123.4 (3)
O1Wi—Zn1—N2iii	88.43 (10)	N2—C22—H22	118.3
N2ii—Zn1—N2iii	180.0	C21—C22—H22	118.3
O4—C1—O3	122.8 (3)	N2—C23—C24	123.3 (3)
O4—C1—C2	124.9 (3)	N2—C23—H23	118.3
O3—C1—C2	112.3 (3)	C24—C23—H23	118.3
C3—C2—C7	119.4 (3)	C23—C24—C20	120.1 (3)
C3—C2—C1	119.5 (3)	C23—C24—H24	120.0
C7—C2—C1	121.0 (3)	C20—C24—H24	120.0
C2—C3—C4	120.2 (3)	N3—C25—H25A	109.5
C2—C3—H3	119.9	N3—C25—H25B	109.5
C4—C3—H3	119.9	H25A—C25—H25B	109.5
C3—C4—C5	120.8 (3)	N3—C25—H25C	109.5
C3—C4—H4	119.6	H25A—C25—H25C	109.5
C5—C4—H4	119.6	H25B—C25—H25C	109.5
C6—C5—C4	118.0 (3)	N3—C26—H26A	109.5
C6—C5—C8	119.6 (3)	N3—C26—H26B	109.5
C4—C5—C8	122.4 (3)	H26A—C26—H26B	109.5
C7—C6—C5	121.4 (3)	N3—C26—H26C	109.5
C7—C6—H6	119.3	H26A—C26—H26C	109.5
C5—C6—H6	119.3	H26B—C26—H26C	109.5
C6—C7—C2	120.3 (3)	O5—C27—N3	126.7 (5)
C6—C7—H7	119.9	O5—C27—H27	116.6
C2—C7—H7	119.9	N3—C27—H27	116.6
N1—C8—C9	122.5 (3)	N4—C28—H28A	109.5
N1—C8—C5	115.0 (3)	N4—C28—H28B	109.5
C9—C8—C5	122.4 (3)	H28A—C28—H28B	109.5
C10—C9—C8	119.7 (3)	N4—C28—H28C	109.5
C10—C9—H9	120.1	H28A—C28—H28C	109.5
C8—C9—H9	120.1	H28B—C28—H28C	109.5
C9—C10—C11	117.1 (3)	N4—C29—H29A	109.5
C9—C10—C20	122.3 (3)	N4—C29—H29B	109.5
C11—C10—C20	120.5 (3)	H29A—C29—H29B	109.5
C12—C11—C10	119.8 (3)	N4—C29—H29C	109.5
C12—C11—H11	120.1	H29A—C29—H29C	109.5
C10—C11—H11	120.1	H29B—C29—H29C	109.5
N1—C12—C11	122.8 (3)	O6—C30—N4	124.6 (4)
N1—C12—C13	116.1 (3)	O6—C30—H30	117.7
C11—C12—C13	121.1 (3)	N4—C30—H30	117.7
C14—C13—C18	118.5 (3)	C8—N1—C12	118.0 (3)
C14—C13—C12	121.4 (3)	C22—N2—C23	116.7 (3)
C18—C13—C12	120.1 (3)	C22—N2—Zn1iv	122.2 (2)
C15—C14—C13	120.8 (3)	C23—N2—Zn1iv	120.6 (2)
C15—C14—H14	119.6	C27—N3—C25	120.0 (4)
C13—C14—H14	119.6	C27—N3—C26	123.2 (4)
C14—C15—C16	120.3 (3)	C25—N3—C26	116.6 (4)
C14—C15—H15	119.8	C30—N4—C29	121.4 (4)
C16—C15—H15	119.8	C30—N4—C28	120.6 (4)
C15—C16—C17	119.0 (3)	C29—N4—C28	117.8 (4)
C15—C16—C19	120.3 (3)	C19—O1—Zn1	128.7 (2)
C17—C16—C19	120.7 (3)	C1—O3—H3A	119 (3)
C18—C17—C16	120.7 (3)	Zn1—O1W—H1A	122 (3)
C18—C17—H17	119.7	Zn1—O1W—H1B	111 (3)
C16—C17—H17	119.7	H1A—O1W—H1B	98 (4)
O4—C1—C2—C3	−9.9 (5)	C19—C16—C17—C18	−179.7 (3)
O3—C1—C2—C3	171.1 (3)	C16—C17—C18—C13	0.8 (5)
O4—C1—C2—C7	166.5 (3)	C14—C13—C18—C17	−1.7 (5)
O3—C1—C2—C7	−12.6 (5)	C12—C13—C18—C17	177.6 (3)
C7—C2—C3—C4	−0.7 (5)	C15—C16—C19—O1	12.2 (4)
C1—C2—C3—C4	175.7 (3)	C17—C16—C19—O1	−167.6 (3)
C2—C3—C4—C5	−0.1 (5)	C15—C16—C19—O2	−166.8 (3)
C3—C4—C5—C6	−0.1 (5)	C17—C16—C19—O2	13.4 (5)
C3—C4—C5—C8	−178.2 (3)	C9—C10—C20—C24	26.9 (4)
C4—C5—C6—C7	1.1 (4)	C11—C10—C20—C24	−150.4 (3)
C8—C5—C6—C7	179.3 (3)	C9—C10—C20—C21	−158.1 (3)
C5—C6—C7—C2	−1.9 (5)	C11—C10—C20—C21	24.6 (4)
C3—C2—C7—C6	1.7 (5)	C24—C20—C21—C22	3.3 (4)
C1—C2—C7—C6	−174.6 (3)	C10—C20—C21—C22	−171.9 (3)
C6—C5—C8—N1	−7.2 (4)	C20—C21—C22—N2	0.7 (5)
C4—C5—C8—N1	170.9 (3)	N2—C23—C24—C20	0.6 (5)
C6—C5—C8—C9	173.1 (3)	C21—C20—C24—C23	−3.9 (4)
C4—C5—C8—C9	−8.8 (4)	C10—C20—C24—C23	171.3 (3)
N1—C8—C9—C10	−1.9 (4)	C9—C8—N1—C12	1.8 (4)
C5—C8—C9—C10	177.7 (3)	C5—C8—N1—C12	−177.9 (2)
C8—C9—C10—C11	0.7 (4)	C11—C12—N1—C8	−0.4 (4)
C8—C9—C10—C20	−176.6 (3)	C13—C12—N1—C8	179.2 (2)
C9—C10—C11—C12	0.5 (4)	C21—C22—N2—C23	−4.0 (5)
C20—C10—C11—C12	177.9 (3)	C21—C22—N2—Zn1iv	168.0 (2)
C10—C11—C12—N1	−0.7 (5)	C24—C23—N2—C22	3.4 (5)
C10—C11—C12—C13	179.6 (3)	C24—C23—N2—Zn1iv	−168.8 (2)
N1—C12—C13—C14	−150.2 (3)	O5—C27—N3—C25	4.1 (8)
C11—C12—C13—C14	29.5 (4)	O5—C27—N3—C26	−172.1 (5)
N1—C12—C13—C18	30.6 (4)	O6—C30—N4—C29	4.2 (6)
C11—C12—C13—C18	−149.7 (3)	O6—C30—N4—C28	178.8 (4)
C18—C13—C14—C15	1.2 (5)	O2—C19—O1—Zn1	−5.2 (5)
C12—C13—C14—C15	−178.1 (3)	C16—C19—O1—Zn1	175.85 (19)
C13—C14—C15—C16	0.1 (5)	O1W—Zn1—O1—C19	24.7 (3)
C14—C15—C16—C17	−1.0 (5)	O1Wi—Zn1—O1—C19	−155.3 (3)
C14—C15—C16—C19	179.3 (3)	N2ii—Zn1—O1—C19	113.1 (3)
C15—C16—C17—C18	0.5 (5)	N2iii—Zn1—O1—C19	−66.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O6v	0.85 (1)	1.93 (2)	2.750 (4)	164 (4)
O1W—H1B···O2	0.85 (1)	1.98 (2)	2.718 (3)	145 (4)
O3—H3A···O2vi	0.86 (1)	1.77 (2)	2.592 (3)	161 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O6i	0.85 (1)	1.93 (2)	2.750 (4)	164 (4)
O1W—H1B⋯O2	0.85 (1)	1.98 (2)	2.718 (3)	145 (4)
O3—H3A⋯O2ii	0.86 (1)	1.77 (2)	2.592 (3)	161 (5)

Symmetry codes: (i) ; (ii) .