catena-Poly[[[(2,2′-bipyridyl-κ²N,N′)zinc(II)]-μ₃-(5-hydroxy­isophthalato-κ⁴O,O′:O′′:O′′′)] monohydrate]

The title compound, {[Zn(C₈H₄O₅)(C₁₀H₈N₂)]·H₂O}_n, was synthesized by reacting Zn(NO₃)₂, 5-hydroxy­isophthalic acid and 2,2′-bipyridine under hydro­thermal conditions. Self-assembly between the bridging ligands, chelating ligands and metal ions results in a one-dimensional coordination polymer, in which the Zn^II atom is six-coordinate and shows a [ZnN₂O₄] octa­hedral geometry. The ribbons are inter­connected by an extensive network of hydrogen bonds involving the water mol­ecule, the hydroxyl group and the carboxyl­ate O atoms, forming a two-dimensional layer. These layers are connected through π–π inter­actions between the pyridyl rings [centroid-to-centroid distance 3.57 (1) Å].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Zn1    -   O2      ..      12.44 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT128_ALERT_4_C Non-standard setting of Space-group P2/c    ....      P2/n
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   O1      ..       9.45 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   O3_b    ..       5.62 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The design and construction of coordination polymers has attracted much attention owing to their intriguing topologies and potential applications as functional materials (Inoue et al., 2001). Many networks with various structural motifs have been documented in the past decade (Amabilino & Stoddart, 1995). Unlike pyridine-2,4-, 3,4- 2,5- and 2,6-dicarboxylic acids, which have been widely used as bridging ligands to assemble various coordination polymers, 5-hydroxyisophthalic acid (H₂hip) as a member of the multicarboxylate ligands has been rarely reported (Plater et al., 2001). We report here the synthesis and structure of a zinc(II) coordination polymer constructed from 5-hydroxyisophthalic acid and 2,2'-bipyridine (bpy).

In the title compound, the asymmetric unit contains one Zn^II atom, one hip ligand, one bpy ligand and one lattice water molecule. Each Zn^II atom is coordinated by four O atoms from three hip ligands (Table 1) and two N atoms from a chelating bpy ligand in a distorted octahedral geometry (Fig. 1). Each pair of adjacent Zn^II atoms are bridged by two hip ligands to form a binuclear Zn subunit. The adjacent binuclear subunits are further interconnected by two hip ligands to form a one-dimensional ribbon running along the a + c direction (Fig. 2). These ribbons are decorated with bpy ligands alternately at two sides.

The ribbons are interconnected by an extensive network of hydrogen bonds involving water molecule, hydroxyl group and carboxylate O atoms (Table 2), forming a two-dimensional layer. The layers are connected through π–π interactions between the pyridyl rings with a centroid-to-centroid distance of 3.57 (1) Å.

Related literature

For related literature, see: Amabilino & Stoddart (1995); Inoue et al. (2001); Plater et al. (2001).

S2. Experimental

A mixture of Zn(NO₃)₂.2H₂O (0.120 g, 0.5 mmol), 5-hydroxyisophthalic acid (0.091 g, 0.5 mmol), 2,2'-bipyridine (0.078 g, 0.5 mmol), NaOH (0.04 g, 1 mmol) and water (10 ml) was sealed in a 23 ml Teflon-lined reactor, which was heated at 453 K for 6 d and then cooled to room temperature at a rate of 5 K h^-1 (yield 58%). Analysis calculated for C₁₈H₁₄N₂O₆Zn: C 51.51, H 3.36, N 6.67%; found: C 51.68, H 3.64, N 6.73%.

S3. Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). H atoms of water molecule were located in a difference Fourier map and refined with a distance restrain of O—H = 0.85 (1) and U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures

	Fig. 1. Part of the polymeric structure of the title compound with symmetric equivalent atoms to complete the Zn coordination. Displacement ellipsoids are drawn at the 30% probability level. Lattice water molecule has been omitted. [Symmetry codes: (i) x + 1/2, -y + 2, z + 1/2; (ii) -x, -y + 2, -z.]
	Fig. 2. A view of the one-dimensional ribbon structure. H atoms and lattice water molecule have been omitted for clarity.

catena-Poly[[(2,2'-bipyridyl-κ²N,N')zinc(II)]-µ₃– (5-hydroxyisophthalato-κ⁴O,O':O'':O''') monohydrate]

Crystal data

[Zn(C8H4O5)(C10H8N2)]·H2O	F(000) = 856
Mr = 419.68	Dx = 1.656 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 3685 reflections
a = 8.777 (2) Å	θ = 2.5–22.4°
b = 10.9763 (16) Å	µ = 1.50 mm^−1
c = 17.981 (3) Å	T = 293 K
β = 103.650 (14)°	Block, colourless
V = 1683.4 (5) Å^3	0.37 × 0.32 × 0.23 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3880 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ϕ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→1
Tmin = 0.608, Tmax = 0.720	k = −1→14
5111 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0632P)^2] where P = (Fo^2 + 2Fc^2)/3
3880 reflections	(Δ/σ)max = 0.001
250 parameters	Δρmax = 0.43 e Å^−3
3 restraints	Δρmin = −0.72 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.04335 (4)	0.79387 (3)	0.171663 (16)	0.02547 (12)
C1	−0.1934 (4)	0.8493 (3)	0.06332 (15)	0.0333 (7)
C2	−0.3194 (3)	0.8800 (3)	−0.00631 (14)	0.0266 (6)
C3	−0.2932 (3)	0.9639 (3)	−0.06037 (14)	0.0265 (6)
H3A	−0.1974	1.0041	−0.0529	0.032*
C4	−0.4116 (3)	0.9871 (2)	−0.12579 (14)	0.0252 (6)
C5	−0.5553 (3)	0.9282 (3)	−0.13638 (15)	0.0294 (6)
H5A	−0.6339	0.9437	−0.1800	0.035*
C6	−0.5818 (3)	0.8457 (3)	−0.08168 (16)	0.0290 (6)
C7	−0.4635 (4)	0.8226 (3)	−0.01715 (15)	0.0297 (6)
H7A	−0.4811	0.7678	0.0194	0.036*
C8	−0.3810 (3)	1.0759 (3)	−0.18412 (14)	0.0260 (6)
C9	−0.0538 (4)	0.6455 (3)	0.29853 (17)	0.0422 (8)
H9A	−0.0723	0.7214	0.3176	0.051*
C10	−0.0911 (5)	0.5421 (4)	0.33393 (19)	0.0558 (10)
H10A	−0.1345	0.5484	0.3762	0.067*
C11	−0.0640 (5)	0.4309 (4)	0.3066 (2)	0.0634 (12)
H11A	−0.0877	0.3604	0.3303	0.076*
C12	−0.0003 (5)	0.4235 (3)	0.2430 (2)	0.0509 (9)
H12A	0.0187	0.3482	0.2232	0.061*
C13	0.1464 (4)	0.4292 (3)	0.1073 (2)	0.0473 (8)
H13A	0.1391	0.3524	0.1280	0.057*
C14	0.2047 (4)	0.4431 (4)	0.0426 (2)	0.0546 (10)
H14A	0.2353	0.3751	0.0188	0.066*
C15	0.2171 (4)	0.5564 (4)	0.0140 (2)	0.0510 (9)
H15A	0.2572	0.5670	−0.0290	0.061*
C16	0.1694 (4)	0.6549 (3)	0.04976 (17)	0.0393 (7)
H16A	0.1782	0.7325	0.0303	0.047*
C17	0.0992 (3)	0.5322 (3)	0.14052 (17)	0.0320 (6)
C18	0.0340 (4)	0.5299 (3)	0.20978 (17)	0.0333 (7)
N1	0.0082 (3)	0.6396 (2)	0.23741 (13)	0.0313 (5)
N2	0.1105 (3)	0.6432 (2)	0.11174 (13)	0.0297 (5)
O1	−0.0610 (3)	0.9002 (2)	0.07345 (12)	0.0420 (5)
O2	−0.2190 (3)	0.7718 (2)	0.10882 (12)	0.0491 (6)
O3	−0.2652 (2)	1.1432 (2)	−0.16680 (11)	0.0359 (5)
O4	−0.4802 (2)	1.07902 (19)	−0.24867 (10)	0.0329 (5)
O5	−0.7167 (3)	0.7825 (2)	−0.08941 (13)	0.0432 (6)
H5B	−0.7905	0.8242	−0.1123	0.065*
O1W	0.9935 (4)	0.1276 (2)	0.15885 (16)	0.0578 (7)
H1WA	1.003 (6)	0.086 (3)	0.1992 (13)	0.087*
H1WB	1.014 (6)	0.085 (3)	0.1235 (15)	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03291 (19)	0.02413 (18)	0.01813 (16)	0.00019 (14)	0.00356 (12)	−0.00048 (12)
C1	0.0404 (17)	0.0369 (16)	0.0210 (12)	0.0125 (14)	0.0042 (12)	−0.0026 (12)
C2	0.0306 (14)	0.0297 (14)	0.0193 (11)	0.0034 (12)	0.0058 (10)	−0.0008 (11)
C3	0.0263 (13)	0.0314 (14)	0.0206 (11)	−0.0006 (12)	0.0027 (10)	−0.0018 (11)
C4	0.0296 (14)	0.0262 (13)	0.0195 (11)	−0.0015 (12)	0.0053 (10)	0.0002 (10)
C5	0.0307 (14)	0.0337 (15)	0.0216 (12)	0.0005 (13)	0.0018 (11)	0.0021 (11)
C6	0.0276 (14)	0.0304 (15)	0.0292 (13)	−0.0018 (12)	0.0071 (11)	0.0015 (12)
C7	0.0371 (16)	0.0284 (14)	0.0246 (12)	0.0024 (13)	0.0090 (12)	0.0044 (11)
C8	0.0298 (14)	0.0274 (14)	0.0209 (12)	−0.0011 (12)	0.0066 (11)	0.0001 (10)
C9	0.0488 (19)	0.050 (2)	0.0289 (14)	−0.0088 (17)	0.0105 (14)	−0.0011 (14)
C10	0.064 (2)	0.071 (3)	0.0339 (17)	−0.015 (2)	0.0151 (17)	0.0118 (18)
C11	0.077 (3)	0.054 (2)	0.060 (2)	−0.018 (2)	0.019 (2)	0.023 (2)
C12	0.060 (2)	0.0345 (18)	0.056 (2)	−0.0060 (17)	0.0090 (18)	0.0107 (16)
C13	0.054 (2)	0.0302 (16)	0.055 (2)	0.0049 (16)	0.0071 (17)	−0.0062 (15)
C14	0.053 (2)	0.052 (2)	0.061 (2)	0.0072 (19)	0.0178 (19)	−0.0225 (19)
C15	0.051 (2)	0.063 (2)	0.0433 (19)	−0.0040 (19)	0.0198 (17)	−0.0173 (18)
C16	0.0465 (19)	0.0411 (18)	0.0344 (15)	−0.0047 (16)	0.0175 (14)	−0.0064 (14)
C17	0.0290 (15)	0.0302 (15)	0.0338 (15)	−0.0015 (13)	0.0014 (12)	−0.0023 (12)
C18	0.0325 (15)	0.0300 (15)	0.0336 (15)	−0.0038 (13)	0.0002 (12)	0.0010 (12)
N1	0.0349 (13)	0.0339 (13)	0.0235 (11)	−0.0032 (11)	0.0038 (10)	0.0042 (10)
N2	0.0314 (13)	0.0285 (12)	0.0296 (12)	−0.0034 (11)	0.0083 (10)	−0.0056 (10)
O1	0.0365 (12)	0.0500 (14)	0.0333 (11)	0.0009 (11)	−0.0044 (9)	0.0020 (10)
O2	0.0505 (15)	0.0616 (16)	0.0317 (11)	0.0056 (13)	0.0029 (10)	0.0201 (11)
O3	0.0363 (11)	0.0440 (12)	0.0266 (10)	−0.0162 (10)	0.0062 (9)	0.0010 (9)
O4	0.0380 (11)	0.0356 (11)	0.0211 (9)	−0.0060 (9)	−0.0009 (8)	0.0071 (8)
O5	0.0322 (12)	0.0487 (14)	0.0468 (13)	−0.0086 (11)	0.0057 (10)	0.0143 (11)
O1W	0.0690 (18)	0.0398 (14)	0.0631 (17)	0.0135 (14)	0.0125 (15)	0.0079 (13)

Geometric parameters (Å, º)

Zn1—O4^i	2.0449 (19)	C9—H9A	0.9300
Zn1—O3^ii	2.087 (2)	C10—C11	1.357 (6)
Zn1—N1	2.129 (2)	C10—H10A	0.9300
Zn1—N2	2.131 (2)	C11—C12	1.390 (6)
Zn1—O1	2.135 (2)	C11—H11A	0.9300
Zn1—O2	2.326 (3)	C12—C18	1.377 (4)
C1—O2	1.237 (4)	C12—H12A	0.9300
C1—O1	1.263 (4)	C13—C17	1.387 (4)
C1—C2	1.500 (4)	C13—C14	1.386 (5)
C2—C7	1.385 (4)	C13—H13A	0.9300
C2—C3	1.397 (4)	C14—C15	1.360 (6)
C3—C4	1.397 (4)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.373 (5)
C4—C5	1.390 (4)	C15—H15A	0.9300
C4—C8	1.502 (4)	C16—N2	1.341 (4)
C5—C6	1.396 (4)	C16—H16A	0.9300
C5—H5A	0.9300	C17—N2	1.337 (4)
C6—O5	1.351 (4)	C17—C18	1.489 (4)
C6—C7	1.386 (4)	C18—N1	1.342 (4)
C7—H7A	0.9300	O3—Zn1^ii	2.087 (2)
C8—O3	1.235 (3)	O4—Zn1^iii	2.0449 (19)
C8—O4	1.277 (3)	O5—H5B	0.8200
C9—N1	1.338 (4)	O1W—H1WA	0.85 (3)
C9—C10	1.378 (5)	O1W—H1WB	0.85 (3)
O4^i—Zn1—O3^ii	93.05 (8)	O3—C8—O4	123.9 (3)
O4^i—Zn1—N1	95.83 (9)	O3—C8—C4	118.9 (2)
O3^ii—Zn1—N1	123.06 (9)	O4—C8—C4	117.2 (2)
O4^i—Zn1—N2	165.77 (8)	N1—C9—C10	121.7 (3)
O3^ii—Zn1—N2	82.17 (9)	N1—C9—H9A	119.1
N1—Zn1—N2	75.95 (10)	C10—C9—H9A	119.1
O4^i—Zn1—O1	96.42 (9)	C11—C10—C9	119.5 (3)
O3^ii—Zn1—O1	90.39 (9)	C11—C10—H10A	120.2
N1—Zn1—O1	143.52 (9)	C9—C10—H10A	120.2
N2—Zn1—O1	97.00 (9)	C10—C11—C12	119.3 (3)
O4^i—Zn1—O2	99.15 (9)	C10—C11—H11A	120.4
O3^ii—Zn1—O2	147.19 (8)	C12—C11—H11A	120.4
N1—Zn1—O2	86.00 (9)	C18—C12—C11	118.6 (4)
N2—Zn1—O2	91.94 (9)	C18—C12—H12A	120.7
O1—Zn1—O2	58.17 (8)	C11—C12—H12A	120.7
O4^i—Zn1—C1	99.93 (9)	C17—C13—C14	118.6 (3)
O3^ii—Zn1—C1	119.10 (9)	C17—C13—H13A	120.7
N1—Zn1—C1	114.40 (10)	C14—C13—H13A	120.7
N2—Zn1—C1	94.09 (9)	C15—C14—C13	119.7 (3)
O1—Zn1—C1	29.40 (9)	C15—C14—H14A	120.1
O2—Zn1—C1	28.80 (9)	C13—C14—H14A	120.1
O2—C1—O1	120.9 (3)	C14—C15—C16	118.9 (3)
O2—C1—C2	119.5 (3)	C14—C15—H15A	120.5
O1—C1—C2	119.6 (3)	C16—C15—H15A	120.5
O2—C1—Zn1	64.87 (17)	N2—C16—C15	122.2 (3)
O1—C1—Zn1	56.11 (15)	N2—C16—H16A	118.9
C2—C1—Zn1	173.3 (2)	C15—C16—H16A	118.9
C7—C2—C3	119.8 (2)	N2—C17—C13	121.3 (3)
C7—C2—C1	119.0 (3)	N2—C17—C18	114.7 (3)
C3—C2—C1	121.2 (3)	C13—C17—C18	124.0 (3)
C4—C3—C2	119.6 (3)	N1—C18—C12	121.8 (3)
C4—C3—H3A	120.2	N1—C18—C17	115.2 (3)
C2—C3—H3A	120.2	C12—C18—C17	123.0 (3)
C5—C4—C3	120.1 (2)	C9—N1—C18	119.0 (3)
C5—C4—C8	120.8 (2)	C9—N1—Zn1	123.9 (2)
C3—C4—C8	119.1 (2)	C18—N1—Zn1	116.67 (19)
C4—C5—C6	120.1 (2)	C17—N2—C16	119.2 (3)
C4—C5—H5A	119.9	C17—N2—Zn1	117.20 (19)
C6—C5—H5A	119.9	C16—N2—Zn1	123.5 (2)
O5—C6—C7	117.2 (3)	C1—O1—Zn1	94.49 (18)
O5—C6—C5	123.3 (3)	C1—O2—Zn1	86.3 (2)
C7—C6—C5	119.5 (3)	C8—O3—Zn1^ii	155.2 (2)
C2—C7—C6	120.9 (3)	C8—O4—Zn1^iii	119.67 (18)
C2—C7—H7A	119.5	C6—O5—H5B	109.5
C6—C7—H7A	119.5	H1WA—O1W—H1WB	111 (3)
O4^i—Zn1—C1—O2	−90.96 (19)	C17—C18—N1—Zn1	5.8 (3)
O3^ii—Zn1—C1—O2	169.88 (17)	O4^i—Zn1—N1—C9	16.1 (3)
N1—Zn1—C1—O2	10.2 (2)	O3^ii—Zn1—N1—C9	113.6 (2)
N2—Zn1—C1—O2	86.58 (19)	N2—Zn1—N1—C9	−175.7 (3)
O1—Zn1—C1—O2	−176.4 (3)	O1—Zn1—N1—C9	−93.0 (3)
O4^i—Zn1—C1—O1	85.45 (18)	O2—Zn1—N1—C9	−82.7 (3)
O3^ii—Zn1—C1—O1	−13.7 (2)	C1—Zn1—N1—C9	−87.6 (3)
N1—Zn1—C1—O1	−173.44 (17)	O4^i—Zn1—N1—C18	−171.7 (2)
N2—Zn1—C1—O1	−97.02 (18)	O3^ii—Zn1—N1—C18	−74.2 (2)
O2—Zn1—C1—O1	176.4 (3)	N2—Zn1—N1—C18	−3.5 (2)
O2—C1—C2—C7	1.5 (4)	O1—Zn1—N1—C18	79.2 (3)
O1—C1—C2—C7	179.3 (3)	O2—Zn1—N1—C18	89.5 (2)
O2—C1—C2—C3	−177.8 (3)	C1—Zn1—N1—C18	84.6 (2)
O1—C1—C2—C3	0.1 (4)	C13—C17—N2—C16	−0.4 (4)
C7—C2—C3—C4	−1.4 (4)	C18—C17—N2—C16	179.3 (3)
C1—C2—C3—C4	177.8 (2)	C13—C17—N2—Zn1	−177.3 (2)
C2—C3—C4—C5	0.9 (4)	C18—C17—N2—Zn1	2.4 (3)
C2—C3—C4—C8	−179.0 (2)	C15—C16—N2—C17	0.8 (5)
C3—C4—C5—C6	0.0 (4)	C15—C16—N2—Zn1	177.5 (3)
C8—C4—C5—C6	179.9 (3)	O4^i—Zn1—N2—C17	56.3 (5)
C4—C5—C6—O5	−177.8 (3)	O3^ii—Zn1—N2—C17	127.4 (2)
C4—C5—C6—C7	−0.4 (4)	N1—Zn1—N2—C17	0.4 (2)
C3—C2—C7—C6	1.0 (4)	O1—Zn1—N2—C17	−143.2 (2)
C1—C2—C7—C6	−178.3 (3)	O2—Zn1—N2—C17	−85.0 (2)
O5—C6—C7—C2	177.5 (3)	C1—Zn1—N2—C17	−113.8 (2)
C5—C6—C7—C2	−0.1 (4)	O4^i—Zn1—N2—C16	−120.5 (4)
C5—C4—C8—O3	166.5 (3)	O3^ii—Zn1—N2—C16	−49.4 (2)
C3—C4—C8—O3	−13.6 (4)	N1—Zn1—N2—C16	−176.4 (3)
C5—C4—C8—O4	−11.8 (4)	O1—Zn1—N2—C16	40.1 (3)
C3—C4—C8—O4	168.1 (3)	O2—Zn1—N2—C16	98.2 (2)
N1—C9—C10—C11	0.3 (6)	C1—Zn1—N2—C16	69.5 (3)
C9—C10—C11—C12	−0.6 (6)	O2—C1—O1—Zn1	3.8 (3)
C10—C11—C12—C18	0.3 (6)	C2—C1—O1—Zn1	−174.0 (2)
C17—C13—C14—C15	1.2 (6)	O4^i—Zn1—O1—C1	−98.84 (18)
C13—C14—C15—C16	−0.8 (6)	O3^ii—Zn1—O1—C1	168.04 (18)
C14—C15—C16—N2	−0.2 (6)	N1—Zn1—O1—C1	10.1 (3)
C14—C13—C17—N2	−0.6 (5)	N2—Zn1—O1—C1	85.89 (18)
C14—C13—C17—C18	179.7 (3)	O2—Zn1—O1—C1	−2.04 (17)
C11—C12—C18—N1	0.3 (5)	O1—C1—O2—Zn1	−3.5 (3)
C11—C12—C18—C17	−178.7 (3)	C2—C1—O2—Zn1	174.3 (2)
N2—C17—C18—N1	−5.4 (4)	O4^i—Zn1—O2—C1	93.99 (18)
C13—C17—C18—N1	174.3 (3)	O3^ii—Zn1—O2—C1	−16.5 (3)
N2—C17—C18—C12	173.6 (3)	N1—Zn1—O2—C1	−170.74 (19)
C13—C17—C18—C12	−6.7 (5)	N2—Zn1—O2—C1	−94.97 (19)
C10—C9—N1—C18	0.3 (5)	O1—Zn1—O2—C1	2.08 (17)
C10—C9—N1—Zn1	172.4 (3)	O4—C8—O3—Zn1^ii	−71.6 (6)
C12—C18—N1—C9	−0.6 (5)	C4—C8—O3—Zn1^ii	110.2 (4)
C17—C18—N1—C9	178.4 (3)	O3—C8—O4—Zn1^iii	−2.8 (4)
C12—C18—N1—Zn1	−173.2 (3)	C4—C8—O4—Zn1^iii	175.39 (17)

Symmetry codes: (i) x+1/2, −y+2, z+1/2; (ii) −x, −y+2, −z; (iii) x−1/2, −y+2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1W^iv	0.82	1.86	2.646 (4)	161
O1W—H1WA···O4^v	0.85 (3)	2.02 (2)	2.790 (3)	150 (4)
O1W—H1WB···O1^vi	0.85 (3)	2.25 (3)	2.910 (4)	135 (4)

Symmetry codes: (iv) −x, −y+1, −z; (v) x+3/2, −y+1, z+1/2; (vi) x+1, y−1, z.