Poly[(μ(3)-benzene-1,3,5-tricarboxyl-ato-κO:O:O)(μ(2)-2-methyl-imidazolato-κN:N')tris-(2-methyl-imidazole-κN)dizinc(II)].

Hydro-thermal reaction involving zinc nitrate hexa-hydrate, tris-odium benzene-1,3,5-tricarboxyl-ate (Na(3)BTC) and 2-methyl-imidazole (2-MeImH) yielded the title compound, [Zn(2)(C(9)H(3)O(6))(C(4)H(5)N(2))(C(4)H(6)N(2))(3)]. In this mixed-ligand metal-organic compound, Zn(2+) ions are coordinated by N atoms from 2-MeImH mol-ecules and (2-MeIm)(-) ions, as well as by O atoms from (BTC)(3-) ions. This results in two different distorted tetra-hedra, viz. ZnN(3)O and ZnN(2)O(2). These tetra-hedra are inter-connected via (BTC)(3-) ions and N:N'-bridging (2-MeIm)(-) ions, thus forming a layered structure in the bc plane. Hydrogen bonds between the O atoms of carboxyl-ate ions and NH groups of 2-MeImH ligands link the layers into a three-dimensional structure.

Related literature

For metal-organic frameworks, see: Li et al. (1999 ▶); Kitagawa et al. (2004 ▶); Stock (2010 ▶); Maniam et al. (2010 ▶). For related structures, see: Cheng et al. (2001 ▶); Zheng et al. (2010 ▶); Huang et al. (2006 ▶); Martins et al. (2010 ▶); Park et al. (2006 ▶).

Experimental

Crystal data

[Zn2(C9H3O6)(C4H5N2)(C4H6N2)3]

M = 665.28

Orthorhombic,

a = 18.9722 (6) Å

b = 18.2247 (4) Å

c = 16.5585 (4) Å

V = 5725.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.73 mm−1

T = 293 K

0.16 × 0.09 × 0.07 mm

Data collection

Stoe IPDS-1 diffractometer

Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2008 ▶) T min = 0.684, T max = 0.814

38494 measured reflections

7732 independent reflections

6222 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.143

S = 1.13

7732 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.54 e Å−3

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015844/bt5531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015844/bt5531Isup2.hkl

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

[Zn2(C9H3O6)(C4H5N2)(C4H6N2)3]	F(000) = 2720
Mr = 665.28	Dx = 1.544 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 40409 reflections
a = 18.9722 (6) Å	θ = 1.6–29.7°
b = 18.2247 (4) Å	µ = 1.73 mm−1
c = 16.5585 (4) Å	T = 293 K
V = 5725.3 (3) Å3	Block, colourless
Z = 8	0.16 × 0.09 × 0.07 mm

Stoe IPDS-1 diffractometer	7732 independent reflections
Radiation source: fine-focus sealed tube	6222 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ scans	θmax = 29.3°, θmin = 1.6°
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2008)	h = −26→26
Tmin = 0.684, Tmax = 0.814	k = −24→23
38494 measured reflections	l = −16→22

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0602P)2 + 8.9412P] where P = (Fo2 + 2Fc2)/3
7732 reflections	(Δ/σ)max < 0.001
370 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.54 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	0.45797 (2)	0.21003 (2)	0.06434 (3)	0.03012 (11)
Zn2	0.86974 (2)	−0.02837 (2)	0.16875 (2)	0.02691 (11)
O1	0.82544 (13)	0.04108 (16)	−0.22416 (15)	0.0317 (6)
O2	0.75851 (19)	0.1297 (2)	−0.27156 (19)	0.0542 (9)
O3	0.54340 (16)	0.20240 (19)	−0.1090 (2)	0.0482 (8)
O4	0.53500 (14)	0.15579 (16)	0.01530 (17)	0.0372 (6)
O5	0.73489 (17)	0.0422 (2)	0.14383 (17)	0.0461 (8)
O6	0.81368 (14)	−0.01665 (16)	0.06956 (16)	0.0367 (6)
C1	0.73604 (17)	0.0869 (2)	−0.1391 (2)	0.0262 (6)
C2	0.67256 (19)	0.1251 (2)	−0.1327 (2)	0.0301 (7)
H2A	0.6548	0.1500	−0.1773	0.036*
C3	0.63563 (18)	0.1261 (2)	−0.0602 (2)	0.0299 (7)
C4	0.66398 (18)	0.0910 (2)	0.0066 (2)	0.0301 (7)
H4A	0.6397	0.0921	0.0554	0.036*
C5	0.72805 (18)	0.0544 (2)	0.0019 (2)	0.0271 (7)
C6	0.76310 (18)	0.0509 (2)	−0.0720 (2)	0.0276 (7)
H6A	0.8048	0.0243	−0.0763	0.033*
C7	0.77524 (18)	0.0865 (2)	−0.2179 (2)	0.0289 (7)
C8	0.56601 (18)	0.1652 (2)	−0.0522 (2)	0.0302 (7)
C9	0.76020 (19)	0.0245 (2)	0.0779 (2)	0.0296 (7)
C1E	0.9480 (2)	0.1157 (3)	0.1420 (3)	0.0398 (9)
C2E	0.9061 (3)	0.1880 (3)	0.2364 (3)	0.0512 (11)
H2E	0.8966	0.2290	0.2680	0.061*
C3E	0.8810 (2)	0.1201 (3)	0.2469 (3)	0.0423 (9)
H3E	0.8505	0.1058	0.2879	0.051*
C4E	0.9881 (3)	0.0916 (3)	0.0703 (3)	0.0579 (13)
H4E1	1.0137	0.1325	0.0484	0.070*
H4E2	0.9561	0.0730	0.0304	0.070*
H4E3	1.0206	0.0537	0.0856	0.070*
N1E	0.90718 (18)	0.07433 (19)	0.1879 (2)	0.0352 (7)
N2E	0.9484 (2)	0.1849 (2)	0.1696 (3)	0.0471 (9)
H2EN	0.9713	0.2210	0.1489	0.057*
C1F	0.3558 (2)	0.1785 (2)	−0.0669 (3)	0.0396 (9)
C2F	0.3373 (2)	0.2885 (3)	−0.0222 (3)	0.0427 (10)
H2F	0.3412	0.3314	0.0079	0.051*
C3F	0.2905 (2)	0.2767 (3)	−0.0822 (3)	0.0495 (11)
H3F	0.2565	0.3093	−0.1010	0.059*
C4F	0.3840 (3)	0.1032 (3)	−0.0801 (4)	0.0613 (15)
H4F1	0.3585	0.0800	−0.1232	0.074*
H4F2	0.3787	0.0749	−0.0315	0.074*
H4F3	0.4330	0.1060	−0.0941	0.074*
N1F	0.37830 (16)	0.22648 (19)	−0.0125 (2)	0.0353 (7)
N2F	0.30319 (19)	0.2075 (2)	−0.1096 (3)	0.0479 (9)
H2FN	0.2809	0.1861	−0.1482	0.057*
C1G	0.3665 (3)	0.1373 (3)	0.1915 (4)	0.0604 (14)
C2G	0.4502 (3)	0.0661 (3)	0.1528 (4)	0.0667 (16)
H2G	0.4899	0.0485	0.1260	0.080*
C3G	0.4119 (4)	0.0282 (4)	0.2072 (4)	0.0738 (17)
H3G	0.4194	−0.0198	0.2241	0.089*
C4G	0.3175 (5)	0.2000 (5)	0.1996 (7)	0.131 (4)
H4G1	0.2818	0.1883	0.2386	0.157*
H4G2	0.2958	0.2098	0.1484	0.157*
H4G3	0.3431	0.2426	0.2172	0.157*
N1G	0.4217 (2)	0.1347 (2)	0.1431 (2)	0.0444 (8)
N2G	0.3604 (3)	0.0740 (3)	0.2321 (3)	0.0631 (13)
H2GN	0.3290	0.0643	0.2680	0.076*
C1H	0.94630 (18)	−0.1645 (2)	0.1130 (2)	0.0328 (8)
C2H	1.01834 (19)	−0.0828 (2)	0.1579 (2)	0.0338 (8)
H2H	1.0369	−0.0393	0.1782	0.041*
C3H	1.05531 (18)	−0.1437 (2)	0.1393 (3)	0.0359 (8)
H3H	1.1038	−0.1493	0.1452	0.043*
C4H	0.8800 (2)	−0.2001 (3)	0.0853 (4)	0.0578 (15)
H4H1	0.8900	−0.2490	0.0671	0.069*
H4H2	0.8601	−0.1721	0.0418	0.069*
H4H3	0.8470	−0.2020	0.1293	0.069*
N1H	0.94875 (15)	−0.09609 (18)	0.14179 (19)	0.0302 (6)
N2H	1.01007 (16)	−0.19593 (18)	0.1103 (2)	0.0324 (7)

	U11	U22	U33	U12	U13	U23
Zn1	0.02406 (18)	0.0339 (2)	0.0324 (2)	−0.00044 (16)	0.00318 (16)	−0.00303 (18)
Zn2	0.02578 (18)	0.0330 (2)	0.02195 (18)	0.00254 (16)	0.00150 (15)	0.00171 (16)
O1	0.0277 (11)	0.0457 (15)	0.0218 (11)	0.0058 (10)	0.0038 (9)	−0.0020 (11)
O2	0.064 (2)	0.067 (2)	0.0317 (15)	0.0266 (17)	0.0106 (14)	0.0175 (16)
O3	0.0392 (15)	0.059 (2)	0.0460 (17)	0.0201 (14)	0.0056 (14)	0.0122 (16)
O4	0.0305 (13)	0.0449 (15)	0.0361 (15)	0.0112 (11)	0.0091 (11)	0.0009 (12)
O5	0.0490 (17)	0.066 (2)	0.0232 (12)	0.0188 (15)	0.0029 (12)	0.0022 (14)
O6	0.0354 (13)	0.0493 (17)	0.0254 (12)	0.0162 (12)	−0.0044 (10)	0.0017 (12)
C1	0.0248 (15)	0.0310 (17)	0.0228 (15)	−0.0002 (13)	0.0014 (12)	−0.0024 (13)
C2	0.0306 (16)	0.0342 (18)	0.0253 (16)	0.0060 (14)	−0.0006 (13)	0.0027 (15)
C3	0.0293 (16)	0.0323 (17)	0.0281 (17)	0.0038 (13)	0.0033 (14)	0.0000 (14)
C4	0.0268 (15)	0.0383 (19)	0.0252 (16)	0.0017 (14)	0.0035 (13)	0.0017 (15)
C5	0.0274 (15)	0.0325 (17)	0.0215 (15)	0.0023 (13)	−0.0009 (12)	−0.0003 (13)
C6	0.0255 (15)	0.0323 (17)	0.0250 (16)	0.0041 (12)	−0.0006 (12)	−0.0012 (14)
C7	0.0283 (15)	0.0357 (18)	0.0228 (15)	0.0002 (13)	0.0002 (12)	0.0002 (14)
C8	0.0256 (15)	0.0348 (18)	0.0300 (18)	0.0031 (13)	0.0010 (13)	−0.0009 (15)
C9	0.0301 (16)	0.0369 (18)	0.0217 (15)	0.0030 (14)	−0.0010 (12)	0.0014 (14)
C1E	0.037 (2)	0.044 (2)	0.038 (2)	−0.0042 (17)	0.0001 (16)	0.0052 (18)
C2E	0.058 (3)	0.041 (2)	0.054 (3)	−0.005 (2)	−0.004 (2)	−0.009 (2)
C3E	0.042 (2)	0.044 (2)	0.041 (2)	−0.0027 (17)	0.0055 (17)	−0.0072 (19)
C4E	0.061 (3)	0.065 (3)	0.048 (3)	−0.002 (3)	0.019 (2)	0.014 (3)
N1E	0.0395 (17)	0.0330 (17)	0.0330 (17)	−0.0053 (13)	0.0025 (13)	−0.0001 (13)
N2E	0.049 (2)	0.0393 (19)	0.053 (2)	−0.0128 (16)	−0.0061 (18)	0.0047 (18)
C1F	0.0324 (18)	0.042 (2)	0.045 (2)	−0.0075 (16)	−0.0023 (16)	−0.0096 (19)
C2F	0.0330 (18)	0.043 (2)	0.052 (3)	0.0046 (16)	−0.0054 (17)	−0.016 (2)
C3F	0.037 (2)	0.057 (3)	0.055 (3)	0.0069 (19)	−0.0136 (19)	−0.014 (2)
C4F	0.058 (3)	0.040 (3)	0.086 (4)	−0.003 (2)	−0.010 (3)	−0.021 (3)
N1F	0.0261 (14)	0.0379 (17)	0.0420 (18)	−0.0006 (12)	−0.0046 (13)	−0.0075 (14)
N2F	0.0368 (17)	0.057 (2)	0.049 (2)	−0.0025 (16)	−0.0129 (16)	−0.0165 (19)
C1G	0.066 (3)	0.054 (3)	0.061 (3)	−0.016 (2)	0.034 (3)	−0.003 (3)
C2G	0.063 (3)	0.061 (3)	0.076 (4)	0.006 (3)	0.016 (3)	0.024 (3)
C3G	0.080 (4)	0.067 (4)	0.074 (4)	−0.005 (3)	0.008 (3)	0.028 (3)
C4G	0.130 (7)	0.093 (6)	0.169 (10)	0.021 (5)	0.116 (7)	0.016 (6)
N1G	0.0441 (19)	0.049 (2)	0.0405 (19)	−0.0053 (16)	0.0117 (16)	0.0037 (17)
N2G	0.072 (3)	0.070 (3)	0.047 (2)	−0.027 (2)	0.020 (2)	0.004 (2)
C1H	0.0244 (16)	0.039 (2)	0.0348 (19)	0.0002 (14)	0.0025 (14)	−0.0037 (16)
C2H	0.0288 (16)	0.041 (2)	0.0317 (19)	0.0012 (15)	−0.0039 (14)	−0.0053 (16)
C3H	0.0219 (15)	0.048 (2)	0.038 (2)	0.0040 (14)	−0.0044 (14)	−0.0122 (18)
C4H	0.0225 (18)	0.058 (3)	0.092 (4)	0.0010 (18)	0.000 (2)	−0.024 (3)
N1H	0.0244 (13)	0.0361 (16)	0.0302 (15)	0.0039 (12)	0.0007 (11)	−0.0044 (13)
N2H	0.0257 (14)	0.0363 (17)	0.0350 (16)	0.0034 (12)	0.0002 (12)	−0.0051 (14)

Zn1—O4	1.942 (3)	N2E—H2EN	0.8600
Zn2—O6	1.968 (3)	C1F—N1F	1.325 (5)
Zn2—O1i	1.976 (2)	C1F—N2F	1.333 (6)
Zn1—N2Hii	1.971 (3)	C1F—C4F	1.490 (7)
Zn1—N1F	1.998 (3)	C2F—C3F	1.349 (6)
Zn1—N1G	2.015 (4)	C2F—N1F	1.381 (5)
Zn2—N1H	1.992 (3)	C2F—H2F	0.9300
Zn2—N1E	2.027 (3)	C3F—N2F	1.361 (6)
O1—C7	1.265 (4)	C3F—H3F	0.9300
O2—C7	1.228 (5)	C4F—H4F1	0.9600
O3—C8	1.236 (5)	C4F—H4F2	0.9600
O4—C8	1.274 (5)	C4F—H4F3	0.9600
O5—C9	1.236 (5)	N2F—H2FN	0.8600
O6—C9	1.269 (4)	C1G—N1G	1.319 (6)
C1—C6	1.388 (5)	C1G—N2G	1.340 (7)
C1—C2	1.395 (5)	C1G—C4G	1.480 (10)
C1—C7	1.503 (5)	C2G—C3G	1.348 (8)
C2—C3	1.390 (5)	C2G—N1G	1.372 (7)
C2—H2A	0.9300	C2G—H2G	0.9300
C3—C4	1.386 (5)	C3G—N2G	1.349 (8)
C3—C8	1.507 (5)	C3G—H3G	0.9300
C4—C5	1.389 (5)	C4G—H4G1	0.9600
C4—H4A	0.9300	C4G—H4G2	0.9600
C5—C6	1.394 (5)	C4G—H4G3	0.9600
C5—C9	1.501 (5)	N2G—H2GN	0.8600
C6—H6A	0.9300	C1H—N1H	1.336 (5)
C1E—N1E	1.321 (5)	C1H—N2H	1.339 (4)
C1E—N2E	1.340 (6)	C1H—C4H	1.488 (5)
C1E—C4E	1.477 (7)	C2H—C3H	1.348 (6)
C2E—C3E	1.338 (7)	C2H—N1H	1.369 (4)
C2E—N2E	1.368 (7)	C2H—H2H	0.9300
C2E—H2E	0.9300	C3H—N2H	1.368 (5)
C3E—N1E	1.377 (5)	C3H—H3H	0.9300
C3E—H3E	0.9300	C4H—H4H1	0.9600
C4E—H4E1	0.9600	C4H—H4H2	0.9600
C4E—H4E2	0.9600	C4H—H4H3	0.9600
C4E—H4E3	0.9600
O4—Zn1—N2Hii	111.87 (13)	N1F—C1F—N2F	109.9 (4)
O4—Zn1—N1F	112.28 (13)	N1F—C1F—C4F	126.3 (4)
N2Hii—Zn1—N1F	110.38 (14)	N2F—C1F—C4F	123.8 (4)
O4—Zn1—N1G	100.42 (14)	C3F—C2F—N1F	109.0 (4)
N2Hii—Zn1—N1G	116.61 (16)	C3F—C2F—H2F	125.5
N1F—Zn1—N1G	104.81 (15)	N1F—C2F—H2F	125.5
O6—Zn2—O1i	122.12 (11)	C2F—C3F—N2F	106.1 (4)
O6—Zn2—N1H	106.66 (12)	C2F—C3F—H3F	127.0
O1i—Zn2—N1H	116.64 (13)	N2F—C3F—H3F	127.0
O6—Zn2—N1E	102.68 (13)	C1F—C4F—H4F1	109.5
O1i—Zn2—N1E	96.73 (13)	C1F—C4F—H4F2	109.5
N1H—Zn2—N1E	110.08 (13)	H4F1—C4F—H4F2	109.5
C7—O1—Zn2iii	118.0 (2)	C1F—C4F—H4F3	109.5
C8—O4—Zn1	130.2 (3)	H4F1—C4F—H4F3	109.5
C9—O6—Zn2	113.9 (2)	H4F2—C4F—H4F3	109.5
C6—C1—C2	119.6 (3)	C1F—N1F—C2F	106.2 (3)
C6—C1—C7	120.7 (3)	C1F—N1F—Zn1	125.3 (3)
C2—C1—C7	119.7 (3)	C2F—N1F—Zn1	128.5 (3)
C3—C2—C1	120.5 (3)	C1F—N2F—C3F	108.8 (4)
C3—C2—H2A	119.8	C1F—N2F—H2FN	125.6
C1—C2—H2A	119.8	C3F—N2F—H2FN	125.6
C4—C3—C2	119.2 (3)	N1G—C1G—N2G	110.0 (5)
C4—C3—C8	119.2 (3)	N1G—C1G—C4G	125.6 (5)
C2—C3—C8	121.6 (3)	N2G—C1G—C4G	124.4 (5)
C3—C4—C5	121.1 (3)	C3G—C2G—N1G	109.4 (6)
C3—C4—H4A	119.5	C3G—C2G—H2G	125.3
C5—C4—H4A	119.5	N1G—C2G—H2G	125.3
C4—C5—C6	119.3 (3)	N2G—C3G—C2G	106.1 (6)
C4—C5—C9	118.9 (3)	N2G—C3G—H3G	126.9
C6—C5—C9	121.7 (3)	C2G—C3G—H3G	126.9
C1—C6—C5	120.3 (3)	C1G—C4G—H4G1	109.5
C1—C6—H6A	119.9	C1G—C4G—H4G2	109.5
C5—C6—H6A	119.9	H4G1—C4G—H4G2	109.5
O2—C7—O1	123.7 (3)	C1G—C4G—H4G3	109.5
O2—C7—C1	119.8 (3)	H4G1—C4G—H4G3	109.5
O1—C7—C1	116.5 (3)	H4G2—C4G—H4G3	109.5
O3—C8—O4	125.5 (3)	C1G—N1G—C2G	105.9 (4)
O3—C8—C3	119.8 (3)	C1G—N1G—Zn1	129.8 (4)
O4—C8—C3	114.7 (3)	C2G—N1G—Zn1	124.2 (3)
O5—C9—O6	124.1 (3)	C1G—N2G—C3G	108.5 (4)
O5—C9—C5	119.2 (3)	C1G—N2G—H2GN	125.8
O6—C9—C5	116.7 (3)	C3G—N2G—H2GN	125.8
N1E—C1E—N2E	110.2 (4)	N1H—C1H—N2H	112.3 (3)
N1E—C1E—C4E	126.4 (4)	N1H—C1H—C4H	123.1 (3)
N2E—C1E—C4E	123.4 (4)	N2H—C1H—C4H	124.6 (4)
C3E—C2E—N2E	105.9 (4)	C3H—C2H—N1H	108.2 (3)
C3E—C2E—H2E	127.0	C3H—C2H—H2H	125.9
N2E—C2E—H2E	127.0	N1H—C2H—H2H	125.9
C2E—C3E—N1E	109.9 (4)	C2H—C3H—N2H	109.1 (3)
C2E—C3E—H3E	125.1	C2H—C3H—H3H	125.5
N1E—C3E—H3E	125.1	N2H—C3H—H3H	125.5
C1E—C4E—H4E1	109.5	C1H—C4H—H4H1	109.5
C1E—C4E—H4E2	109.5	C1H—C4H—H4H2	109.5
H4E1—C4E—H4E2	109.5	H4H1—C4H—H4H2	109.5
C1E—C4E—H4E3	109.5	C1H—C4H—H4H3	109.5
H4E1—C4E—H4E3	109.5	H4H1—C4H—H4H3	109.5
H4E2—C4E—H4E3	109.5	H4H2—C4H—H4H3	109.5
C1E—N1E—C3E	105.8 (4)	C1H—N1H—C2H	105.6 (3)
C1E—N1E—Zn2	130.0 (3)	C1H—N1H—Zn2	129.2 (2)
C3E—N1E—Zn2	122.9 (3)	C2H—N1H—Zn2	124.9 (3)
C1E—N2E—C2E	108.2 (4)	C1H—N2H—C3H	104.9 (3)
C1E—N2E—H2EN	125.9	C1H—N2H—Zn1iv	131.5 (3)
C2E—N2E—H2EN	125.9	C3H—N2H—Zn1iv	123.2 (2)
N2Hii—Zn1—O4—C8	−76.9 (4)	N1F—C2F—C3F—N2F	−0.3 (6)
N1F—Zn1—O4—C8	47.9 (4)	N2F—C1F—N1F—C2F	0.0 (5)
N1G—Zn1—O4—C8	158.8 (4)	C4F—C1F—N1F—C2F	179.9 (5)
O1i—Zn2—O6—C9	41.1 (3)	N2F—C1F—N1F—Zn1	−178.4 (3)
N1H—Zn2—O6—C9	178.8 (3)	C4F—C1F—N1F—Zn1	1.5 (7)
N1E—Zn2—O6—C9	−65.4 (3)	C3F—C2F—N1F—C1F	0.2 (5)
C6—C1—C2—C3	−1.3 (6)	C3F—C2F—N1F—Zn1	178.5 (3)
C7—C1—C2—C3	−180.0 (3)	O4—Zn1—N1F—C1F	37.9 (4)
C1—C2—C3—C4	2.5 (6)	N2Hii—Zn1—N1F—C1F	163.5 (3)
C1—C2—C3—C8	−178.4 (3)	N1G—Zn1—N1F—C1F	−70.2 (4)
C2—C3—C4—C5	−0.7 (6)	O4—Zn1—N1F—C2F	−140.1 (4)
C8—C3—C4—C5	−179.9 (3)	N2Hii—Zn1—N1F—C2F	−14.6 (4)
C3—C4—C5—C6	−2.2 (6)	N1G—Zn1—N1F—C2F	111.8 (4)
C3—C4—C5—C9	173.4 (4)	N1F—C1F—N2F—C3F	−0.2 (6)
C2—C1—C6—C5	−1.7 (5)	C4F—C1F—N2F—C3F	179.9 (5)
C7—C1—C6—C5	177.0 (3)	C2F—C3F—N2F—C1F	0.3 (6)
C4—C5—C6—C1	3.4 (5)	N1G—C2G—C3G—N2G	−1.1 (8)
C9—C5—C6—C1	−172.1 (3)	N2G—C1G—N1G—C2G	1.3 (7)
Zn2iii—O1—C7—O2	−9.8 (5)	C4G—C1G—N1G—C2G	−177.9 (8)
Zn2iii—O1—C7—C1	171.5 (2)	N2G—C1G—N1G—Zn1	178.2 (4)
C6—C1—C7—O2	−165.6 (4)	C4G—C1G—N1G—Zn1	−1.0 (11)
C2—C1—C7—O2	13.0 (6)	C3G—C2G—N1G—C1G	−0.1 (8)
C6—C1—C7—O1	13.2 (5)	C3G—C2G—N1G—Zn1	−177.2 (5)
C2—C1—C7—O1	−168.2 (3)	O4—Zn1—N1G—C1G	−175.7 (5)
Zn1—O4—C8—O3	−16.3 (6)	N2Hii—Zn1—N1G—C1G	63.3 (5)
Zn1—O4—C8—C3	164.1 (3)	N1F—Zn1—N1G—C1G	−59.1 (5)
C4—C3—C8—O3	173.2 (4)	O4—Zn1—N1G—C2G	0.7 (5)
C2—C3—C8—O3	−5.9 (6)	N2Hii—Zn1—N1G—C2G	−120.3 (5)
C4—C3—C8—O4	−7.2 (5)	N1F—Zn1—N1G—C2G	117.3 (5)
C2—C3—C8—O4	173.7 (4)	N1G—C1G—N2G—C3G	−2.0 (7)
Zn2—O6—C9—O5	−16.2 (5)	C4G—C1G—N2G—C3G	177.2 (8)
Zn2—O6—C9—C5	161.9 (3)	C2G—C3G—N2G—C1G	1.9 (8)
C4—C5—C9—O5	−10.7 (6)	N1H—C2H—C3H—N2H	0.7 (5)
C6—C5—C9—O5	164.7 (4)	N2H—C1H—N1H—C2H	0.4 (5)
C4—C5—C9—O6	171.0 (3)	C4H—C1H—N1H—C2H	−178.0 (4)
C6—C5—C9—O6	−13.5 (5)	N2H—C1H—N1H—Zn2	−173.3 (3)
N2E—C2E—C3E—N1E	0.2 (6)	C4H—C1H—N1H—Zn2	8.2 (6)
N2E—C1E—N1E—C3E	−0.1 (5)	C3H—C2H—N1H—C1H	−0.7 (4)
C4E—C1E—N1E—C3E	−179.9 (5)	C3H—C2H—N1H—Zn2	173.4 (3)
N2E—C1E—N1E—Zn2	167.5 (3)	O6—Zn2—N1H—C1H	−57.7 (4)
C4E—C1E—N1E—Zn2	−12.4 (7)	O1i—Zn2—N1H—C1H	82.7 (4)
C2E—C3E—N1E—C1E	−0.1 (5)	N1E—Zn2—N1H—C1H	−168.4 (3)
C2E—C3E—N1E—Zn2	−168.8 (3)	O6—Zn2—N1H—C2H	129.6 (3)
O6—Zn2—N1E—C1E	−60.7 (4)	O1i—Zn2—N1H—C2H	−89.9 (3)
O1i—Zn2—N1E—C1E	174.2 (4)	N1E—Zn2—N1H—C2H	18.9 (4)
N1H—Zn2—N1E—C1E	52.6 (4)	N1H—C1H—N2H—C3H	0.0 (5)
O6—Zn2—N1E—C3E	105.0 (3)	C4H—C1H—N2H—C3H	178.4 (5)
O1i—Zn2—N1E—C3E	−20.1 (4)	N1H—C1H—N2H—Zn1iv	−172.7 (3)
N1H—Zn2—N1E—C3E	−141.7 (3)	C4H—C1H—N2H—Zn1iv	5.7 (7)
N1E—C1E—N2E—C2E	0.2 (5)	C2H—C3H—N2H—C1H	−0.4 (5)
C4E—C1E—N2E—C2E	−179.9 (5)	C2H—C3H—N2H—Zn1iv	173.0 (3)
C3E—C2E—N2E—C1E	−0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2E—H2EN···O3v	0.86	2.06	2.912 (5)	169
N2F—H2FN···O2vi	0.86	1.84	2.693 (5)	172
N2G—H2GN···O5vii	0.86	1.94	2.798 (5)	175

Table 1

Selected geometric parameters (Å, °)

Zn1—O4	1.942 (3)
Zn2—O6	1.968 (3)
Zn2—O1i	1.976 (2)
Zn1—N2Hii	1.971 (3)
Zn1—N1F	1.998 (3)
Zn1—N1G	2.015 (4)
Zn2—N1H	1.992 (3)
Zn2—N1E	2.027 (3)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2E—H2EN⋯O3iii	0.86	2.06	2.912 (5)	169
N2F—H2FN⋯O2iv	0.86	1.84	2.693 (5)	172
N2G—H2GN⋯O5v	0.86	1.94	2.798 (5)	175

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