Poly[[hexa-aqua-bis-(μ(3)-benzene-1,3,5-tricarboxyl-ato-κO:O:O)bis-(5,5'-dimethyl-2,2'-bipyridine-κN,N')trizinc] hexa-hydrate].

In the title compound, {[Zn(3)(C(9)H(3)O(6))(2)(C(12)H(12)N(2))(2)(H(2)O)(6)]·6H(2)O}(n), one Zn(II) atom, lying on an inversion center, is six-coordinated by two O atoms from two benzene-1,3,5-tricarboxyl-ate (btc) ligands and four water mol-ecules in a distorted octa-hedral geometry. The other Zn(II) atom is five-coordinated by two N atoms from a 5,5'-dimethyl-2,2'-bipyridine (dmbpy) ligand, two O atoms from two btc ligands and one water mol-ecule in a distorted trigonal-bipyramidal geometry. The compound features a one-dimensional ladder structure, with windows of ca 10.245 (1) × 15.446 (2) Å. The ladders are linked together by inter-molecular O-H⋯O hydrogen bonds and π-π inter-actions between the benzene rings and between the pyridine rings [centroid-to-centroid distances 3.858 (2) and 3.911 (3) Å, respectively] to form a three-dimensional supra-molecular structure. One of the lattice water molecules is disordered over two positions in a 0.592:0.408 ratio.

Related literature

For background to network topologies and the applications of coordination polymers, see: Maspoch et al. (2007 ▶); Ockwig et al. (2005 ▶). For background to effective methods for the construction of coordination polymers, see: Du et al. (2007 ▶); Zang et al. (2006 ▶, 2010 ▶). For O—H⋯O hydrogen bonds, see: Desiraju (2004 ▶).

Experimental

Crystal data

[Zn3(C9H3O6)2(C12H12N2)2(H2O)6]·6H2O

M = 1195.00

Triclinic,

a = 10.2454 (10) Å

b = 10.5799 (10) Å

c = 12.658 (1) Å

α = 68.910 (8)°

β = 74.848 (8)°

γ = 81.834 (8)°

V = 1233.90 (19) Å3

Z = 1

Mo Kα radiation

μ = 1.54 mm−1

T = 296 K

0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.739, T max = 0.759

9149 measured reflections

4330 independent reflections

3426 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.01

4330 reflections

336 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022173/hy2439sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022173/hy2439Isup2.hkl

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

[Zn3(C9H3O6)2(C12H12N2)2(H2O)6]·6H2O	Z = 1
Mr = 1195.00	F(000) = 616
Triclinic, P1	Dx = 1.608 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2454 (10) Å	Cell parameters from 3902 reflections
b = 10.5799 (10) Å	θ = 3.0–29.2°
c = 12.658 (1) Å	µ = 1.54 mm−1
α = 68.910 (8)°	T = 296 K
β = 74.848 (8)°	Block, colourless
γ = 81.834 (8)°	0.21 × 0.20 × 0.19 mm
V = 1233.90 (19) Å3

Bruker APEXII CCD diffractometer	4330 independent reflections
Radiation source: fine-focus sealed tube	3426 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→11
Tmin = 0.739, Tmax = 0.759	k = −12→12
9149 measured reflections	l = −14→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.3228P] where P = (Fo2 + 2Fc2)/3
4330 reflections	(Δ/σ)max < 0.001
336 parameters	Δρmax = 0.74 e Å−3
12 restraints	Δρmin = −0.59 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.12533 (4)	0.26423 (4)	0.27950 (4)	0.02392 (16)
Zn2	0.5000	−0.5000	0.5000	0.0307 (2)
O1	0.2755 (2)	0.1223 (3)	0.3318 (2)	0.0318 (7)
O2	0.3634 (3)	0.3178 (3)	0.2870 (3)	0.0402 (7)
O3	0.8425 (3)	0.3214 (2)	0.3035 (2)	0.0308 (7)
O4	0.9762 (2)	0.1367 (2)	0.3164 (2)	0.0291 (6)
O5	0.7603 (3)	−0.3095 (2)	0.4380 (3)	0.0328 (7)
O6	0.5455 (3)	−0.3002 (3)	0.4271 (3)	0.0361 (7)
O1W	0.0603 (3)	0.3070 (3)	0.4344 (2)	0.0333 (7)
H1WA	0.1250	0.3022	0.4656	0.050*
H1WB	−0.0007	0.2560	0.4821	0.050*
O2W	0.4783 (3)	−0.4920 (3)	0.3334 (3)	0.0432 (8)
H2WA	0.4387	−0.5581	0.3356	0.065*
H2WB	0.4504	−0.4322	0.2770	0.065*
O3W	0.7074 (3)	−0.5649 (3)	0.4677 (3)	0.0408 (8)
H3WB	0.7155	−0.6398	0.4555	0.061*
H3WC	0.7508	−0.5056	0.4082	0.061*
O4W	0.4365 (14)	0.6435 (16)	0.0453 (12)	0.117 (3)	0.408 (9)
H4WA	0.4059	0.6795	0.1072	0.175*	0.408 (9)
H4WB	0.4578	0.5864	0.0534	0.175*	0.408 (9)
O4W'	0.4797 (10)	0.5541 (10)	0.0114 (9)	0.117 (3)	0.592 (9)
H4WD	0.4529	0.4924	0.0792	0.175*	0.592 (9)
H4WE	0.4258	0.6206	−0.0140	0.175*	0.592 (9)
O5W	0.3621 (5)	0.7702 (6)	0.2466 (6)	0.142 (2)
H5WA	0.2969	0.7985	0.2914	0.213*
H5WC	0.4226	0.7649	0.2885	0.213*
O6W	0.1335 (5)	0.8711 (5)	0.4028 (4)	0.1048 (18)
H6WB	0.1775	0.9325	0.4047	0.157*
H6WD	0.0961	0.9389	0.3584	0.157*
N1	0.1983 (3)	0.2550 (3)	0.1050 (3)	0.0302 (8)
N2	0.1122 (3)	0.4690 (3)	0.1716 (3)	0.0269 (7)
C1	0.3732 (4)	0.1913 (4)	0.3168 (3)	0.0247 (8)
C2	0.8611 (4)	0.1978 (4)	0.3186 (3)	0.0207 (8)
C3	0.6509 (4)	−0.2463 (4)	0.4204 (3)	0.0248 (8)
C4	0.5062 (3)	0.1165 (4)	0.3354 (3)	0.0216 (8)
C5	0.6183 (3)	0.1867 (4)	0.3203 (3)	0.0235 (8)
H5	0.6110	0.2808	0.2988	0.028*
C6	0.7415 (3)	0.1176 (3)	0.3371 (3)	0.0207 (8)
C7	0.7516 (3)	−0.0216 (3)	0.3692 (3)	0.0201 (8)
H7	0.8338	−0.0679	0.3806	0.024*
C8	0.6407 (4)	−0.0943 (3)	0.3851 (3)	0.0215 (8)
C9	0.5189 (4)	−0.0233 (4)	0.3676 (3)	0.0225 (8)
H9	0.4443	−0.0708	0.3777	0.027*
C10	0.2447 (4)	0.1427 (4)	0.0791 (4)	0.0375 (10)
H10	0.2463	0.0610	0.1400	0.045*
C11	0.2910 (4)	0.1418 (5)	−0.0342 (4)	0.0412 (11)
C12	0.3435 (6)	0.0116 (5)	−0.0579 (5)	0.0621 (15)
H12A	0.3412	−0.0615	0.0144	0.093*
H12B	0.4349	0.0210	−0.1032	0.093*
H12C	0.2876	−0.0075	−0.1000	0.093*
C13	0.2863 (5)	0.2651 (5)	−0.1217 (4)	0.0447 (11)
H13	0.3157	0.2694	−0.1988	0.054*
C14	0.2389 (5)	0.3818 (5)	−0.0967 (4)	0.0419 (11)
H14	0.2364	0.4645	−0.1564	0.050*
C15	0.1949 (4)	0.3746 (4)	0.0188 (3)	0.0304 (9)
C16	0.1458 (4)	0.4930 (4)	0.0569 (4)	0.0287 (9)
C17	0.1358 (4)	0.6233 (4)	−0.0215 (4)	0.0386 (11)
H17	0.1577	0.6387	−0.1010	0.046*
C18	0.0930 (5)	0.7297 (4)	0.0198 (4)	0.0443 (12)
H18	0.0871	0.8175	−0.0322	0.053*
C19	0.0590 (4)	0.7070 (4)	0.1378 (4)	0.0381 (11)
C20	0.0129 (5)	0.8197 (5)	0.1863 (5)	0.0533 (13)
H20A	0.0763	0.8258	0.2281	0.080*
H20B	−0.0747	0.8018	0.2381	0.080*
H20C	0.0073	0.9038	0.1240	0.080*
C21	0.0697 (4)	0.5739 (4)	0.2107 (4)	0.0341 (10)
H21	0.0465	0.5561	0.2906	0.041*

	U11	U22	U33	U12	U13	U23
Zn1	0.0188 (3)	0.0242 (3)	0.0267 (3)	−0.00367 (17)	−0.00609 (18)	−0.00453 (19)
Zn2	0.0273 (4)	0.0215 (3)	0.0435 (4)	−0.0059 (3)	−0.0063 (3)	−0.0107 (3)
O1	0.0175 (14)	0.0356 (15)	0.0417 (18)	−0.0021 (11)	−0.0126 (12)	−0.0080 (13)
O2	0.0321 (17)	0.0315 (16)	0.059 (2)	0.0060 (12)	−0.0200 (15)	−0.0145 (14)
O3	0.0290 (15)	0.0192 (14)	0.0441 (18)	−0.0061 (11)	−0.0087 (13)	−0.0086 (12)
O4	0.0138 (13)	0.0267 (14)	0.0460 (18)	−0.0001 (11)	−0.0073 (12)	−0.0112 (13)
O5	0.0298 (16)	0.0214 (14)	0.0508 (19)	0.0007 (11)	−0.0178 (14)	−0.0111 (13)
O6	0.0268 (15)	0.0224 (14)	0.062 (2)	−0.0077 (11)	−0.0145 (14)	−0.0120 (14)
O1W	0.0301 (15)	0.0433 (17)	0.0287 (16)	−0.0092 (12)	−0.0089 (12)	−0.0104 (13)
O2W	0.055 (2)	0.0332 (16)	0.046 (2)	−0.0066 (14)	−0.0158 (16)	−0.0136 (14)
O3W	0.0314 (16)	0.0288 (15)	0.062 (2)	−0.0021 (12)	−0.0040 (14)	−0.0191 (15)
O4W	0.113 (3)	0.119 (3)	0.118 (3)	−0.0102 (14)	−0.0282 (15)	−0.0372 (15)
O4W'	0.113 (3)	0.119 (3)	0.118 (3)	−0.0102 (14)	−0.0282 (15)	−0.0372 (15)
O5W	0.101 (4)	0.110 (4)	0.181 (6)	0.005 (3)	−0.051 (4)	0.001 (4)
O6W	0.134 (4)	0.123 (4)	0.060 (3)	−0.088 (3)	−0.015 (3)	−0.010 (3)
N1	0.0326 (19)	0.0304 (18)	0.0263 (19)	−0.0060 (14)	−0.0052 (15)	−0.0074 (15)
N2	0.0208 (17)	0.0305 (18)	0.028 (2)	−0.0039 (13)	−0.0064 (14)	−0.0063 (15)
C1	0.0166 (19)	0.034 (2)	0.024 (2)	0.0013 (16)	−0.0068 (15)	−0.0099 (17)
C2	0.021 (2)	0.0235 (19)	0.0158 (19)	−0.0072 (15)	−0.0019 (15)	−0.0034 (15)
C3	0.029 (2)	0.0240 (19)	0.023 (2)	−0.0083 (17)	−0.0042 (16)	−0.0090 (16)
C4	0.0177 (19)	0.029 (2)	0.018 (2)	−0.0007 (15)	−0.0030 (15)	−0.0088 (16)
C5	0.0210 (19)	0.0210 (18)	0.027 (2)	−0.0016 (15)	−0.0076 (16)	−0.0039 (16)
C6	0.0172 (18)	0.0230 (18)	0.023 (2)	−0.0042 (14)	−0.0044 (15)	−0.0075 (16)
C7	0.0162 (18)	0.0193 (17)	0.023 (2)	−0.0018 (14)	−0.0043 (15)	−0.0054 (15)
C8	0.024 (2)	0.0216 (18)	0.020 (2)	−0.0039 (15)	−0.0046 (15)	−0.0082 (16)
C9	0.0166 (19)	0.0274 (19)	0.024 (2)	−0.0048 (15)	−0.0049 (15)	−0.0085 (16)
C10	0.044 (3)	0.032 (2)	0.035 (3)	−0.0078 (19)	−0.009 (2)	−0.008 (2)
C11	0.040 (3)	0.051 (3)	0.039 (3)	−0.005 (2)	−0.007 (2)	−0.023 (2)
C12	0.077 (4)	0.057 (3)	0.058 (4)	0.001 (3)	−0.007 (3)	−0.034 (3)
C13	0.050 (3)	0.057 (3)	0.029 (3)	−0.008 (2)	−0.007 (2)	−0.017 (2)
C14	0.050 (3)	0.044 (3)	0.028 (3)	−0.008 (2)	−0.008 (2)	−0.006 (2)
C15	0.025 (2)	0.036 (2)	0.031 (2)	−0.0059 (17)	−0.0084 (18)	−0.0081 (19)
C16	0.025 (2)	0.029 (2)	0.033 (3)	−0.0058 (16)	−0.0085 (18)	−0.0090 (18)
C17	0.050 (3)	0.033 (2)	0.025 (2)	−0.005 (2)	−0.009 (2)	0.0014 (19)
C18	0.049 (3)	0.030 (2)	0.045 (3)	−0.003 (2)	−0.017 (2)	0.002 (2)
C19	0.031 (2)	0.031 (2)	0.050 (3)	0.0001 (18)	−0.012 (2)	−0.011 (2)
C20	0.056 (3)	0.040 (3)	0.063 (4)	0.001 (2)	−0.010 (3)	−0.020 (3)
C21	0.033 (2)	0.033 (2)	0.036 (3)	−0.0050 (18)	−0.0079 (19)	−0.0092 (19)

Zn1—O4i	2.033 (2)	N2—C16	1.338 (5)
Zn1—O1	2.055 (3)	N2—C21	1.346 (5)
Zn1—O1W	2.089 (3)	C1—C4	1.505 (5)
Zn1—N2	2.112 (3)	C2—C6	1.509 (5)
Zn1—N1	2.172 (3)	C3—C8	1.502 (5)
Zn2—O6ii	2.047 (2)	C4—C9	1.382 (5)
Zn2—O6	2.047 (2)	C4—C5	1.390 (5)
Zn2—O3Wii	2.119 (3)	C5—C6	1.393 (5)
Zn2—O3W	2.119 (3)	C5—H5	0.9300
Zn2—O2W	2.148 (3)	C6—C7	1.375 (5)
Zn2—O2Wii	2.148 (3)	C7—C8	1.393 (5)
O1—C1	1.256 (4)	C7—H7	0.9300
O2—C1	1.250 (5)	C8—C9	1.389 (5)
O3—C2	1.246 (4)	C9—H9	0.9300
O4—C2	1.260 (4)	C10—C11	1.391 (6)
O4—Zn1iii	2.033 (2)	C10—H10	0.9300
O5—C3	1.250 (4)	C11—C13	1.378 (6)
O6—C3	1.260 (4)	C11—C12	1.510 (7)
O1W—H1WA	0.8433	C12—H12A	0.9600
O1W—H1WB	0.8428	C12—H12B	0.9600
O2W—H2WA	0.8457	C12—H12C	0.9600
O2W—H2WB	0.8499	C13—C14	1.375 (7)
O3W—H3WB	0.8500	C13—H13	0.9300
O3W—H3WC	0.8500	C14—C15	1.390 (6)
O4W—H4WA	0.9537	C14—H14	0.9300
O4W—H4WB	0.5942	C15—C16	1.477 (6)
O4W—H4WE	0.9037	C16—C17	1.387 (5)
O4W'—O4W'iv	1.27 (2)	C17—C18	1.377 (6)
O4W'—H4WB	0.7048	C17—H17	0.9300
O4W'—H4WD	0.8736	C18—C19	1.380 (6)
O4W'—H4WE	0.8501	C18—H18	0.9300
O5W—H5WA	0.8514	C19—C21	1.386 (6)
O5W—H5WC	0.9000	C19—C20	1.496 (6)
O6W—H6WB	0.8520	C20—H20A	0.9599
O6W—H6WD	0.8499	C20—H20B	0.9600
N1—C10	1.335 (5)	C20—H20C	0.9601
N1—C15	1.344 (5)	C21—H21	0.9300
O4i—Zn1—O1	98.75 (10)	O6—C3—C8	115.5 (3)
O4i—Zn1—O1W	95.22 (11)	C9—C4—C5	118.9 (3)
O1—Zn1—O1W	95.94 (11)	C9—C4—C1	120.4 (3)
O4i—Zn1—N2	121.50 (11)	C5—C4—C1	120.7 (3)
O1—Zn1—N2	137.13 (11)	C4—C5—C6	120.7 (3)
O1W—Zn1—N2	94.52 (12)	C4—C5—H5	119.7
O4i—Zn1—N1	91.75 (12)	C6—C5—H5	119.7
O1—Zn1—N1	89.17 (12)	C7—C6—C5	119.4 (3)
O1W—Zn1—N1	170.62 (11)	C7—C6—C2	121.7 (3)
N2—Zn1—N1	76.46 (13)	C5—C6—C2	119.0 (3)
O6ii—Zn2—O6	180.00 (15)	C6—C7—C8	121.1 (3)
O6ii—Zn2—O3Wii	91.78 (11)	C6—C7—H7	119.4
O6—Zn2—O3Wii	88.22 (11)	C8—C7—H7	119.4
O6ii—Zn2—O3W	88.22 (11)	C9—C8—C7	118.6 (3)
O6—Zn2—O3W	91.78 (11)	C9—C8—C3	120.0 (3)
O3Wii—Zn2—O3W	180.0	C7—C8—C3	121.4 (3)
O6ii—Zn2—O2W	91.61 (11)	C4—C9—C8	121.4 (3)
O6—Zn2—O2W	88.39 (11)	C4—C9—H9	119.3
O3Wii—Zn2—O2W	86.71 (12)	C8—C9—H9	119.3
O3W—Zn2—O2W	93.29 (12)	N1—C10—C11	123.4 (4)
O6ii—Zn2—O2Wii	88.39 (11)	N1—C10—H10	118.3
O6—Zn2—O2Wii	91.61 (11)	C11—C10—H10	118.3
O3Wii—Zn2—O2Wii	93.29 (12)	C13—C11—C10	116.4 (4)
O3W—Zn2—O2Wii	86.71 (12)	C13—C11—C12	122.7 (4)
O2W—Zn2—O2Wii	180.0	C10—C11—C12	120.9 (4)
C1—O1—Zn1	104.3 (2)	C11—C12—H12A	109.5
C2—O4—Zn1iii	112.2 (2)	C11—C12—H12B	109.5
C3—O6—Zn2	129.0 (2)	H12A—C12—H12B	109.5
Zn1—O1W—H1WA	111.8	C11—C12—H12C	109.5
Zn1—O1W—H1WB	112.0	H12A—C12—H12C	109.5
H1WA—O1W—H1WB	110.0	H12B—C12—H12C	109.5
Zn2—O2W—H2WA	114.2	C14—C13—C11	121.1 (4)
Zn2—O2W—H2WB	135.2	C14—C13—H13	119.5
H2WA—O2W—H2WB	97.6	C11—C13—H13	119.5
Zn2—O3W—H3WB	109.3	C13—C14—C15	119.2 (4)
Zn2—O3W—H3WC	109.3	C13—C14—H14	120.4
H3WB—O3W—H3WC	109.5	C15—C14—H14	120.4
H4WA—O4W—H4WB	121.9	N1—C15—C14	120.4 (4)
H4WA—O4W—H4WE	153.9	N1—C15—C16	115.2 (4)
H4WB—O4W—H4WE	73.1	C14—C15—C16	124.3 (4)
O4W'iv—O4W'—H4WB	148.4	N2—C16—C17	121.1 (4)
O4W'iv—O4W'—H4WD	78.5	N2—C16—C15	116.7 (3)
H4WB—O4W'—H4WD	71.6	C17—C16—C15	122.3 (4)
O4W'iv—O4W'—H4WE	133.7	C18—C17—C16	119.3 (4)
H4WB—O4W'—H4WE	72.4	C18—C17—H17	120.4
H4WD—O4W'—H4WE	119.7	C16—C17—H17	120.4
H5WA—O5W—H5WC	94.0	C17—C18—C19	120.5 (4)
H6WB—O6W—H6WD	82.4	C17—C18—H18	119.8
C10—N1—C15	119.6 (4)	C19—C18—H18	119.8
C10—N1—Zn1	125.4 (3)	C18—C19—C21	116.9 (4)
C15—N1—Zn1	115.0 (3)	C18—C19—C20	122.2 (4)
C16—N2—C21	119.0 (3)	C21—C19—C20	120.8 (4)
C16—N2—Zn1	116.5 (3)	C19—C20—H20A	109.5
C21—N2—Zn1	124.5 (3)	C19—C20—H20B	109.4
O2—C1—O1	122.5 (3)	H20A—C20—H20B	109.5
O2—C1—C4	119.7 (3)	C19—C20—H20C	109.5
O1—C1—C4	117.8 (3)	H20A—C20—H20C	109.5
O3—C2—O4	123.0 (3)	H20B—C20—H20C	109.5
O3—C2—C6	118.8 (3)	N2—C21—C19	123.2 (4)
O4—C2—C6	118.2 (3)	N2—C21—H21	118.4
O5—C3—O6	125.0 (3)	C19—C21—H21	118.4
O5—C3—C8	119.5 (3)
O4i—Zn1—O1—C1	−177.5 (2)	C2—C6—C7—C8	−179.4 (3)
O1W—Zn1—O1—C1	−81.3 (3)	C6—C7—C8—C9	0.1 (6)
N2—Zn1—O1—C1	22.0 (3)	C6—C7—C8—C3	−179.9 (3)
N1—Zn1—O1—C1	90.9 (3)	O5—C3—C8—C9	−178.7 (4)
O3Wii—Zn2—O6—C3	152.0 (4)	O6—C3—C8—C9	3.0 (5)
O3W—Zn2—O6—C3	−28.0 (4)	O5—C3—C8—C7	1.3 (6)
O2W—Zn2—O6—C3	−121.2 (4)	O6—C3—C8—C7	−177.1 (3)
O2Wii—Zn2—O6—C3	58.8 (4)	C5—C4—C9—C8	0.1 (6)
O4i—Zn1—N1—C10	−60.6 (3)	C1—C4—C9—C8	179.9 (3)
O1—Zn1—N1—C10	38.1 (3)	C7—C8—C9—C4	−0.2 (6)
N2—Zn1—N1—C10	177.4 (3)	C3—C8—C9—C4	179.8 (3)
O4i—Zn1—N1—C15	119.6 (3)	C15—N1—C10—C11	0.0 (6)
O1—Zn1—N1—C15	−141.7 (3)	Zn1—N1—C10—C11	−179.8 (3)
N2—Zn1—N1—C15	−2.4 (3)	N1—C10—C11—C13	−0.3 (7)
O4i—Zn1—N2—C16	−80.7 (3)	N1—C10—C11—C12	179.5 (4)
O1—Zn1—N2—C16	76.6 (3)	C10—C11—C13—C14	0.3 (7)
O1W—Zn1—N2—C16	−179.7 (3)	C12—C11—C13—C14	−179.4 (5)
N1—Zn1—N2—C16	2.9 (3)	C11—C13—C14—C15	−0.1 (7)
O4i—Zn1—N2—C21	97.6 (3)	C10—N1—C15—C14	0.2 (6)
O1—Zn1—N2—C21	−105.1 (3)	Zn1—N1—C15—C14	180.0 (3)
O1W—Zn1—N2—C21	−1.3 (3)	C10—N1—C15—C16	−178.1 (3)
N1—Zn1—N2—C21	−178.7 (3)	Zn1—N1—C15—C16	1.7 (4)
Zn1—O1—C1—O2	6.0 (5)	C13—C14—C15—N1	−0.1 (6)
Zn1—O1—C1—C4	−173.7 (3)	C13—C14—C15—C16	178.0 (4)
Zn1iii—O4—C2—O3	−2.2 (5)	C21—N2—C16—C17	−0.9 (6)
Zn1iii—O4—C2—C6	176.1 (2)	Zn1—N2—C16—C17	177.5 (3)
Zn2—O6—C3—O5	14.6 (6)	C21—N2—C16—C15	178.5 (3)
Zn2—O6—C3—C8	−167.1 (2)	Zn1—N2—C16—C15	−3.0 (4)
O2—C1—C4—C9	−179.5 (4)	N1—C15—C16—N2	0.8 (5)
O1—C1—C4—C9	0.1 (5)	C14—C15—C16—N2	−177.4 (4)
O2—C1—C4—C5	0.3 (6)	N1—C15—C16—C17	−179.7 (4)
O1—C1—C4—C5	180.0 (3)	C14—C15—C16—C17	2.0 (6)
C9—C4—C5—C6	0.1 (6)	N2—C16—C17—C18	1.3 (6)
C1—C4—C5—C6	−179.8 (3)	C15—C16—C17—C18	−178.1 (4)
C4—C5—C6—C7	−0.1 (6)	C16—C17—C18—C19	−0.8 (7)
C4—C5—C6—C2	179.3 (3)	C17—C18—C19—C21	−0.1 (6)
O3—C2—C6—C7	−171.4 (3)	C17—C18—C19—C20	179.6 (4)
O4—C2—C6—C7	10.2 (5)	C16—N2—C21—C19	0.0 (6)
O3—C2—C6—C5	9.1 (5)	Zn1—N2—C21—C19	−178.4 (3)
O4—C2—C6—C5	−169.2 (3)	C18—C19—C21—N2	0.6 (6)
C5—C6—C7—C8	0.0 (6)	C20—C19—C21—N2	−179.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5v	0.84	1.93	2.754 (4)	166
O1W—H1WB···O6Wvi	0.84	1.96	2.805 (5)	176
O2W—H2WA···O2vii	0.85	1.95	2.768 (4)	162
O2W—H2WB···O5Wvii	0.85	2.14	2.806 (6)	135
O3W—H3WB···O3vii	0.85	2.16	2.740 (4)	125
O3W—H3WC···O5	0.85	2.26	2.705 (4)	113
O4W—H4WA···O5W	0.95	2.22	3.166 (19)	173
O4W'—H4WD···O2	0.87	2.63	3.499 (11)	177
O5W—H5WA···O6W	0.85	2.14	2.987 (9)	179
O5W—H5WC···O6viii	0.90	2.28	3.151 (7)	164
O6W—H6WB···O1viii	0.85	2.16	2.947 (5)	154
O6W—H6WD···O4ix	0.85	2.23	3.019 (6)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5i	0.84	1.93	2.754 (4)	166
O1W—H1WB⋯O6Wii	0.84	1.96	2.805 (5)	176
O2W—H2WA⋯O2iii	0.85	1.95	2.768 (4)	162
O2W—H2WB⋯O5Wiii	0.85	2.14	2.806 (6)	135
O3W—H3WB⋯O3iii	0.85	2.16	2.740 (4)	125
O3W—H3WC⋯O5	0.85	2.26	2.705 (4)	113
O4W—H4WA⋯O5W	0.95	2.22	3.166 (19)	173
O4W′—H4WD⋯O2	0.87	2.63	3.499 (11)	177
O5W—H5WA⋯O6W	0.85	2.14	2.987 (9)	179
O5W—H5WC⋯O6iv	0.90	2.28	3.151 (7)	164
O6W—H6WB⋯O1iv	0.85	2.16	2.947 (5)	154
O6W—H6WD⋯O4v	0.85	2.23	3.019 (6)	154

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