Two- and three-dimensional coordination polymers based on zinc(II) and furan-2,5-di­carb­oxy­lic acid: structure variation due to metal-to-linker ratio

Two Zn^II-based coordination polymers (CPs) were synthesized by the hydro­thermal method, using Zn(NO₃)₂·6H₂O and furan-2,5-di­carb­oxy­lic acid (FDCA) in di­methyl­formamide (DMF) solvent, at 95 °C. Poly[tetra­kis­(di­methyl­aza­nium) [tetra­kis­(μ₂-furan-2,5-di­carboxyl­ato-κ²O²:O⁵)dizinc(II)]], {(C₂H₈N)₄[Zn₂(C₆H₂O₅)₄]}_n or {[DMA]₄[Zn^II₂(FDC)₄]}_n (DMA = di­methyl­azanium and FDC = furan-2,5-di­carboxyl­ate), (1), was obtained with a 1:1 molar ratio of Zn^II and FDCA. It crystallized in the monoclinic space group C2/c. Coordinated by Zn^II ions, FDC²⁻ ligands form 2₁ double-stranded helices propagating along the b axis. The helices are inter­connected and extend laterally in the a direction, forming a two-dimensional (2D) sheet-like network. The 2D sheets are stacked along the c direction without inter­connections. DMA cations are cocrystallized in (1) and are hydrogen bonded with carboxyl­ate O atoms of the FDC²⁻ ligands. The hydrogen-bonding pattern consists of R₂²(4) and R₂²(10) motifs alternating in a chain. Poly[bis­(di­methyl­aza­nium) [bis­(μ₄-furan-2,5-di­carboxyl­ato-κO²:κO^2′:κO⁵:κO⁵)bis­(μ₃-furan-2,5-di­carboxyl­ato-κO²:κO^2′:κO⁵)dizinc(II)] di­methyl­form­amide 3.08-solvate], {(C₂H₈N)₂[Zn₂(C₆H₂O₅)₄]·3.08C₃H₇NO}_n or {[DMA]₂[Zn^II₃(FDC)₄]·3.08DMF}_n, (2), was obtained with a 1:2 molar ratio of Zn^II and FDCA. It crystallized in the monoclinic space group P2₁/c, forming a three-dimensional network. The pores are filled with DMA cations and DMF solvent mol­ecules.

Computing details

For both structures, data collection: APRX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2008) and VESTA (Momma & Izumi, 2011); software used to prepare material for publication: APEX2 (Bruker, 2010), SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Poly[tetrakis(dimethylazanium) [tetrakis(µ₂-furan-2,5-dicarboxylato-κ²O²:O⁵)dizinc(II)]] (1)

Crystal data

(C2H8N)4[Zn2(C6H2O5)4]	F(000) = 3840
Mr = 931.42	Dx = 1.571 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.9306 (6) Å	Cell parameters from 10240 reflections
b = 23.9322 (6) Å	θ = 2.5–32.4°
c = 14.9917 (4) Å	µ = 1.31 mm^−1
β = 113.4847 (4)°	T = 150 K
V = 7874.7 (4) Å^3	Plate, colourless
Z = 8	0.26 × 0.17 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer	12993 independent reflections
Radiation source: sealed tube	5280 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 8.333 pixels mm^-1	θmax = 31.5°, θmin = 1.6°
φ and ω scans	h = −35→34
Absorption correction: analytical (XPREP; Bruker, 2010)	k = −35→34
Tmin = 0.775, Tmax = 0.949	l = −22→21
52443 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0023P)^2 + 6.9P] where P = (Fo^2 + 2Fc^2)/3
12993 reflections	(Δ/σ)max = 0.001
532 parameters	Δρmax = 1.26 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.24880 (2)	0.31244 (2)	0.25004 (2)	0.01282 (12)
Zn2	0.500000	0.06399 (2)	0.250000	0.01318 (14)
Zn3	0.000000	0.06171 (2)	0.250000	0.01309 (14)
O1A	0.32094 (11)	0.26434 (9)	0.31546 (18)	0.0176 (6)
O2A	0.36043 (9)	0.33271 (7)	0.42596 (15)	0.0211 (5)
C3A	0.36384 (13)	0.28761 (11)	0.3874 (2)	0.0166 (6)
C4A	0.42328 (13)	0.25774 (11)	0.4273 (2)	0.0164 (6)
C5A	0.47709 (16)	0.27004 (13)	0.5022 (3)	0.0176 (9)
H5A	0.485086	0.300598	0.545988	0.021*
C6A	0.51892 (16)	0.22800 (13)	0.5017 (3)	0.0181 (8)
H6A	0.560478	0.225050	0.545211	0.022*
C7A	0.48822 (12)	0.19301 (11)	0.4274 (2)	0.0167 (6)
O8A	0.42898 (8)	0.21053 (7)	0.38013 (14)	0.0160 (4)
C9A	0.50788 (13)	0.14334 (11)	0.3874 (2)	0.0162 (6)
O10A	0.56281 (8)	0.13080 (8)	0.42544 (15)	0.0215 (5)
O11A	0.46652 (10)	0.11781 (9)	0.31633 (18)	0.0176 (5)
O1B	0.18488 (11)	0.25644 (9)	0.18466 (19)	0.0186 (6)
C3B	0.19016 (12)	0.23112 (11)	0.1131 (2)	0.0166 (6)
O2B	0.22561 (9)	0.24406 (8)	0.07421 (15)	0.0213 (5)
C4B	0.15024 (12)	0.18164 (11)	0.0733 (2)	0.0170 (6)
C5B	0.14337 (16)	0.14663 (14)	−0.0019 (3)	0.0188 (8)
H5B	0.163139	0.149376	−0.045539	0.023*
C6B	0.10090 (15)	0.10527 (13)	−0.0023 (3)	0.0171 (8)
H6B	0.086758	0.074710	−0.046045	0.021*
C7B	0.08430 (12)	0.11797 (11)	0.0725 (2)	0.0164 (6)
O8B	0.11411 (8)	0.16479 (7)	0.11989 (13)	0.0160 (4)
C9B	0.04462 (12)	0.08835 (11)	0.1127 (2)	0.0168 (6)
O10B	0.02234 (9)	0.04302 (7)	0.07451 (15)	0.0213 (5)
O11B	0.03711 (10)	0.11202 (9)	0.18358 (18)	0.0177 (5)
O1C	0.20893 (11)	0.36058 (9)	0.31454 (18)	0.0188 (6)
O2C	0.22469 (9)	0.29314 (8)	0.42659 (15)	0.0213 (5)
C3C	0.20188 (12)	0.33804 (11)	0.3867 (2)	0.0162 (6)
C4C	0.16255 (12)	0.36865 (11)	0.4266 (2)	0.0163 (6)
C5C	0.14619 (16)	0.35700 (14)	0.5016 (3)	0.0183 (8)
H5C	0.159552	0.326314	0.545258	0.022*
C6C	0.10528 (15)	0.39969 (13)	0.5018 (3)	0.0179 (8)
H6C	0.085703	0.403148	0.545629	0.021*
C7C	0.09941 (12)	0.43480 (11)	0.4272 (2)	0.0159 (6)
O8C	0.13433 (8)	0.41634 (7)	0.37979 (13)	0.0158 (4)
C9C	0.06028 (12)	0.48445 (11)	0.3870 (2)	0.0165 (6)
O10C	0.02389 (9)	0.49740 (8)	0.42431 (15)	0.0214 (5)
O11C	0.06656 (11)	0.50992 (9)	0.31622 (19)	0.0178 (6)
O1D	0.28125 (10)	0.36821 (9)	0.18571 (18)	0.0185 (6)
C3D	0.24070 (13)	0.39302 (11)	0.1133 (2)	0.0165 (6)
O2D	0.18587 (8)	0.37994 (8)	0.07375 (15)	0.0210 (5)
C4D	0.26107 (12)	0.44224 (11)	0.0734 (2)	0.0159 (6)
C5D	0.23017 (16)	0.47734 (13)	−0.0017 (3)	0.0173 (8)
H5D	0.188708	0.474397	−0.045697	0.021*
C6D	0.27237 (16)	0.51919 (13)	−0.0011 (3)	0.0177 (9)
H6D	0.264607	0.550001	−0.044383	0.021*
C7D	0.32608 (13)	0.50652 (11)	0.0735 (2)	0.0165 (6)
O8D	0.31999 (8)	0.45926 (7)	0.12017 (13)	0.0153 (4)
C9D	0.38583 (13)	0.53592 (11)	0.1130 (2)	0.0165 (6)
O10D	0.38926 (9)	0.58145 (8)	0.07567 (15)	0.0216 (5)
O11D	0.42923 (10)	0.51187 (9)	0.18375 (19)	0.0178 (6)
C1E	0.32221 (16)	0.14937 (15)	0.1656 (3)	0.0257 (9)
H1E1	0.358150	0.126574	0.201973	0.038*
H1E2	0.287987	0.124920	0.128418	0.038*
H1E3	0.311515	0.171838	0.211199	0.038*
N2E	0.33578 (13)	0.18674 (11)	0.0983 (2)	0.0193 (7)
H2E1	0.348550	0.165868	0.059260	0.023*
H2E2	0.301092	0.204816	0.059731	0.023*
C3E	0.38312 (16)	0.22839 (15)	0.1506 (3)	0.0252 (8)
H3E1	0.367438	0.254108	0.186059	0.038*
H3E2	0.394019	0.249453	0.103844	0.038*
H3E3	0.419285	0.209216	0.196734	0.038*
C1F	0.19098 (17)	0.15395 (14)	0.3494 (3)	0.0252 (8)
H1F1	0.160755	0.127816	0.306204	0.038*
H1F2	0.225145	0.132946	0.396575	0.038*
H1F3	0.205876	0.178139	0.310871	0.038*
N2F	0.16249 (13)	0.18862 (11)	0.4017 (2)	0.0194 (7)
H2F1	0.151704	0.166340	0.441400	0.023*
H2F2	0.190199	0.213895	0.439581	0.023*
C3F	0.10794 (16)	0.21866 (15)	0.3343 (3)	0.0268 (9)
H3F1	0.118827	0.241011	0.288792	0.040*
H3F2	0.092500	0.243299	0.371525	0.040*
H3F3	0.076364	0.191574	0.297866	0.040*
C1G	0.06561 (17)	0.39711 (14)	0.1503 (3)	0.0247 (8)
H1G1	0.098884	0.372030	0.188734	0.037*
H1G2	0.032326	0.375233	0.103107	0.037*
H1G3	0.050727	0.417024	0.193670	0.037*
N2G	0.08809 (13)	0.43795 (11)	0.0982 (2)	0.0196 (7)
H2G1	0.056321	0.459043	0.058354	0.024*
H2G2	0.103720	0.419249	0.060536	0.024*
C3G	0.13557 (16)	0.47515 (15)	0.1660 (3)	0.0257 (8)
H3G1	0.117722	0.498372	0.201724	0.039*
H3G2	0.151789	0.499194	0.129023	0.039*
H3G3	0.168593	0.452498	0.212053	0.039*
C1H	0.43391 (17)	0.40512 (15)	0.3345 (3)	0.0261 (9)
H1H1	0.399976	0.382748	0.289924	0.039*
H1H2	0.467880	0.380428	0.371829	0.039*
H1H3	0.447177	0.431672	0.297140	0.039*
N2H	0.41381 (13)	0.43612 (11)	0.4020 (2)	0.0192 (7)
H2H1	0.444773	0.458312	0.441111	0.023*
H2H2	0.404941	0.411359	0.440596	0.023*
C3H	0.35951 (16)	0.47112 (15)	0.3494 (3)	0.0246 (8)
H3H1	0.367924	0.496037	0.304400	0.037*
H3H2	0.349898	0.493448	0.396285	0.037*
H3H3	0.324798	0.447025	0.312843	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0119 (3)	0.0113 (2)	0.0161 (4)	−0.00009 (11)	0.0065 (3)	−0.00020 (12)
Zn2	0.0122 (3)	0.0110 (3)	0.0177 (4)	0.000	0.0073 (3)	0.000
Zn3	0.0121 (3)	0.0108 (3)	0.0174 (4)	0.000	0.0069 (3)	0.000
O1A	0.0158 (13)	0.0173 (11)	0.0173 (16)	0.0038 (10)	0.0039 (12)	−0.0032 (10)
O2A	0.0262 (11)	0.0156 (9)	0.0248 (13)	0.0004 (8)	0.0137 (10)	−0.0049 (9)
C3A	0.0186 (15)	0.0154 (13)	0.0182 (16)	0.0004 (11)	0.0099 (13)	0.0023 (11)
C4A	0.0204 (15)	0.0134 (13)	0.0179 (17)	−0.0005 (11)	0.0102 (13)	−0.0019 (11)
C5A	0.019 (2)	0.0145 (17)	0.019 (2)	−0.0036 (14)	0.0070 (18)	−0.0054 (15)
C6A	0.0119 (19)	0.0212 (18)	0.017 (2)	−0.0014 (14)	0.0013 (16)	0.0006 (15)
C7A	0.0135 (14)	0.0168 (13)	0.0187 (17)	0.0017 (11)	0.0052 (12)	0.0028 (12)
O8A	0.0136 (10)	0.0165 (9)	0.0164 (11)	0.0010 (8)	0.0043 (8)	−0.0027 (8)
C9A	0.0158 (14)	0.0171 (13)	0.0171 (16)	0.0006 (11)	0.0080 (12)	0.0030 (12)
O10A	0.0132 (10)	0.0233 (10)	0.0271 (13)	0.0033 (8)	0.0073 (9)	0.0024 (9)
O11A	0.0150 (12)	0.0182 (11)	0.0173 (15)	0.0041 (9)	0.0041 (10)	−0.0038 (10)
O1B	0.0194 (14)	0.0202 (11)	0.0186 (16)	−0.0073 (10)	0.0102 (12)	−0.0038 (10)
C3B	0.0139 (14)	0.0182 (13)	0.0176 (16)	0.0032 (11)	0.0062 (12)	0.0041 (11)
O2B	0.0191 (11)	0.0245 (10)	0.0249 (13)	0.0006 (8)	0.0134 (9)	0.0043 (9)
C4B	0.0146 (14)	0.0186 (13)	0.0197 (17)	0.0013 (11)	0.0088 (12)	0.0039 (11)
C5B	0.0238 (19)	0.0216 (16)	0.015 (2)	0.0059 (14)	0.0118 (16)	−0.0015 (14)
C6B	0.0174 (17)	0.0120 (15)	0.022 (2)	−0.0042 (13)	0.0084 (16)	−0.0025 (14)
C7B	0.0149 (14)	0.0142 (13)	0.0183 (17)	−0.0007 (11)	0.0045 (12)	−0.0007 (11)
O8B	0.0170 (10)	0.0154 (9)	0.0179 (11)	−0.0028 (8)	0.0095 (9)	−0.0022 (8)
C9B	0.0136 (14)	0.0157 (13)	0.0194 (16)	0.0000 (11)	0.0049 (12)	0.0008 (11)
O10B	0.0215 (11)	0.0145 (9)	0.0264 (13)	−0.0039 (8)	0.0079 (10)	−0.0036 (8)
O11B	0.0206 (12)	0.0172 (11)	0.0184 (15)	−0.0064 (9)	0.0109 (11)	−0.0033 (10)
O1C	0.0224 (13)	0.0182 (11)	0.0180 (15)	0.0077 (9)	0.0104 (11)	0.0032 (10)
O2C	0.0211 (11)	0.0157 (10)	0.0242 (12)	0.0029 (8)	0.0059 (9)	0.0032 (8)
C3C	0.0143 (13)	0.0140 (13)	0.0163 (16)	−0.0021 (11)	0.0020 (12)	−0.0012 (11)
C4C	0.0160 (14)	0.0134 (13)	0.0182 (16)	0.0012 (11)	0.0054 (12)	0.0017 (11)
C5C	0.0218 (18)	0.0189 (15)	0.014 (2)	−0.0035 (13)	0.0066 (15)	0.0061 (14)
C6C	0.0159 (17)	0.0192 (15)	0.022 (2)	0.0023 (13)	0.0112 (16)	0.0000 (14)
C7C	0.0172 (14)	0.0163 (13)	0.0161 (16)	−0.0014 (11)	0.0087 (12)	−0.0015 (11)
O8C	0.0170 (10)	0.0157 (9)	0.0157 (11)	0.0032 (8)	0.0076 (9)	0.0017 (8)
C9C	0.0150 (14)	0.0179 (13)	0.0160 (16)	−0.0010 (11)	0.0057 (12)	−0.0038 (11)
O10C	0.0197 (11)	0.0224 (10)	0.0267 (13)	0.0014 (8)	0.0141 (10)	−0.0032 (9)
O11C	0.0213 (14)	0.0167 (11)	0.0180 (16)	0.0059 (10)	0.0105 (12)	0.0034 (10)
O1D	0.0154 (12)	0.0194 (11)	0.0178 (15)	−0.0045 (9)	0.0036 (11)	0.0042 (10)
C3D	0.0147 (14)	0.0163 (13)	0.0191 (17)	−0.0003 (11)	0.0076 (12)	−0.0029 (12)
O2D	0.0137 (10)	0.0242 (10)	0.0242 (13)	−0.0034 (8)	0.0065 (9)	−0.0036 (9)
C4D	0.0120 (13)	0.0169 (13)	0.0177 (16)	−0.0012 (11)	0.0047 (12)	−0.0011 (11)
C5D	0.0122 (19)	0.0197 (18)	0.017 (2)	0.0021 (14)	0.0031 (17)	0.0001 (15)
C6D	0.020 (2)	0.0152 (17)	0.017 (2)	0.0038 (14)	0.0064 (17)	0.0050 (15)
C7D	0.0171 (14)	0.0144 (13)	0.0194 (17)	0.0010 (11)	0.0086 (13)	0.0023 (11)
O8D	0.0136 (10)	0.0151 (9)	0.0156 (11)	−0.0011 (7)	0.0042 (8)	0.0026 (8)
C9D	0.0207 (15)	0.0149 (13)	0.0170 (16)	0.0007 (11)	0.0107 (13)	−0.0011 (11)
O10D	0.0253 (11)	0.0160 (9)	0.0259 (13)	−0.0012 (8)	0.0125 (10)	0.0038 (8)
O11D	0.0154 (13)	0.0181 (11)	0.0172 (16)	−0.0033 (9)	0.0035 (11)	0.0039 (10)
C1E	0.0225 (18)	0.0271 (18)	0.028 (2)	−0.0007 (14)	0.0102 (16)	0.0022 (15)
N2E	0.0186 (17)	0.0209 (16)	0.017 (2)	0.0052 (13)	0.0052 (15)	−0.0013 (14)
C3E	0.0245 (18)	0.0284 (17)	0.023 (2)	−0.0027 (14)	0.0096 (15)	−0.0021 (14)
C1F	0.0285 (19)	0.0240 (17)	0.022 (2)	0.0018 (14)	0.0094 (16)	0.0015 (14)
N2F	0.0216 (18)	0.0213 (16)	0.015 (2)	−0.0058 (13)	0.0070 (15)	−0.0004 (14)
C3F	0.0244 (19)	0.0250 (17)	0.031 (2)	0.0029 (14)	0.0104 (16)	0.0013 (15)
C1G	0.0240 (18)	0.0289 (18)	0.021 (2)	−0.0015 (14)	0.0085 (15)	0.0012 (14)
N2G	0.0217 (18)	0.0227 (16)	0.015 (2)	0.0080 (13)	0.0075 (15)	0.0023 (14)
C3G	0.0256 (19)	0.0250 (16)	0.027 (2)	−0.0025 (14)	0.0110 (16)	−0.0006 (14)
C1H	0.0277 (19)	0.0246 (17)	0.029 (2)	0.0022 (14)	0.0143 (17)	−0.0003 (15)
N2H	0.0197 (17)	0.0202 (16)	0.016 (2)	−0.0052 (13)	0.0049 (15)	0.0014 (13)
C3H	0.0255 (19)	0.0252 (16)	0.0212 (19)	0.0014 (14)	0.0075 (15)	0.0000 (14)

Geometric parameters (Å, º)

Zn1—O1B	1.975 (2)	C3D—O2D	1.245 (3)
Zn1—O1C	1.977 (2)	C3D—C4D	1.488 (4)
Zn1—O1D	1.978 (2)	C4D—C5D	1.363 (4)
Zn1—O1A	1.979 (2)	C4D—O8D	1.363 (3)
Zn2—O11A	1.981 (2)	C5D—C6D	1.420 (5)
Zn2—O11A^i	1.981 (2)	C5D—H5D	0.9500
Zn2—O11C^ii	1.984 (2)	C6D—C7D	1.360 (5)
Zn2—O11C^iii	1.984 (2)	C6D—H6D	0.9500
Zn3—O11B^iv	1.984 (2)	C7D—O8D	1.368 (3)
Zn3—O11B	1.984 (2)	C7D—C9D	1.488 (4)
Zn3—O11D^v	1.984 (2)	C9D—O10D	1.242 (3)
Zn3—O11D^ii	1.984 (2)	C9D—O11D	1.287 (4)
O1A—C3A	1.282 (4)	C1E—N2E	1.478 (4)
O2A—C3A	1.243 (3)	C1E—H1E1	0.9800
C3A—C4A	1.488 (4)	C1E—H1E2	0.9800
C4A—C5A	1.361 (5)	C1E—H1E3	0.9800
C4A—O8A	1.369 (3)	N2E—C3E	1.478 (4)
C5A—C6A	1.421 (5)	N2E—H2E1	0.9100
C5A—H5A	0.9500	N2E—H2E2	0.9100
C6A—C7A	1.352 (4)	C3E—H3E1	0.9800
C6A—H6A	0.9500	C3E—H3E2	0.9800
C7A—O8A	1.374 (3)	C3E—H3E3	0.9800
C7A—C9A	1.490 (4)	C1F—N2F	1.481 (4)
C9A—O10A	1.243 (3)	C1F—H1F1	0.9800
C9A—O11A	1.284 (4)	C1F—H1F2	0.9800
O1B—C3B	1.282 (4)	C1F—H1F3	0.9800
C3B—O2B	1.244 (3)	N2F—C3F	1.480 (4)
C3B—C4B	1.489 (4)	N2F—H2F1	0.9100
C4B—C5B	1.361 (4)	N2F—H2F2	0.9100
C4B—O8B	1.371 (3)	C3F—H3F1	0.9800
C5B—C6B	1.417 (3)	C3F—H3F2	0.9800
C5B—H5B	0.9500	C3F—H3F3	0.9800
C6B—C7B	1.364 (4)	C1G—N2G	1.480 (4)
C6B—H6B	0.9500	C1G—H1G1	0.9800
C7B—O8B	1.366 (3)	C1G—H1G2	0.9800
C7B—C9B	1.491 (4)	C1G—H1G3	0.9800
C9B—O10B	1.243 (3)	N2G—C3G	1.482 (4)
C9B—O11B	1.279 (4)	N2G—H2G1	0.9100
O1C—C3C	1.279 (4)	N2G—H2G2	0.9100
O2C—C3C	1.245 (3)	C3G—H3G1	0.9800
C3C—C4C	1.492 (4)	C3G—H3G2	0.9800
C4C—C5C	1.360 (4)	C3G—H3G3	0.9800
C4C—O8C	1.369 (3)	C1H—N2H	1.482 (4)
C5C—C6C	1.416 (3)	C1H—H1H1	0.9800
C5C—H5C	0.9500	C1H—H1H2	0.9800
C6C—C7C	1.361 (4)	C1H—H1H3	0.9800
C6C—H6C	0.9500	N2H—C3H	1.482 (4)
C7C—O8C	1.369 (3)	N2H—H2H1	0.9100
C7C—C9C	1.484 (4)	N2H—H2H2	0.9100
C9C—O10C	1.247 (3)	C3H—H3H1	0.9800
C9C—O11C	1.284 (4)	C3H—H3H2	0.9800
O1D—C3D	1.278 (4)	C3H—H3H3	0.9800
O1B—Zn1—O1C	102.05 (10)	O8D—C4D—C3D	117.9 (2)
O1B—Zn1—O1D	126.36 (10)	C4D—C5D—C6D	106.2 (3)
O1C—Zn1—O1D	101.83 (11)	C4D—C5D—H5D	126.9
O1B—Zn1—O1A	101.62 (11)	C6D—C5D—H5D	126.9
O1C—Zn1—O1A	126.31 (10)	C7D—C6D—C5D	106.5 (3)
O1D—Zn1—O1A	101.52 (10)	C7D—C6D—H6D	126.7
O11A—Zn2—O11A^i	98.89 (14)	C5D—C6D—H6D	126.7
O11A—Zn2—O11C^ii	105.70 (9)	C6D—C7D—O8D	110.3 (2)
O11A^i—Zn2—O11C^ii	125.27 (10)	C6D—C7D—C9D	131.7 (3)
O11A—Zn2—O11C^iii	125.27 (10)	O8D—C7D—C9D	117.9 (2)
O11A^i—Zn2—O11C^iii	105.70 (9)	C4D—O8D—C7D	106.5 (2)
O11C^ii—Zn2—O11C^iii	98.59 (13)	O10D—C9D—O11D	125.9 (3)
O11B^iv—Zn3—O11B	105.24 (13)	O10D—C9D—C7D	117.4 (3)
O11B^iv—Zn3—O11D^v	98.78 (10)	O11D—C9D—C7D	116.7 (2)
O11B—Zn3—O11D^v	125.25 (10)	C9D—O11D—Zn3^vii	113.03 (17)
O11B^iv—Zn3—O11D^ii	125.25 (10)	N2E—C1E—H1E1	109.5
O11B—Zn3—O11D^ii	98.78 (10)	N2E—C1E—H1E2	109.5
O11D^v—Zn3—O11D^ii	106.10 (13)	H1E1—C1E—H1E2	109.5
C3A—O1A—Zn1	114.34 (18)	N2E—C1E—H1E3	109.5
O2A—C3A—O1A	126.1 (3)	H1E1—C1E—H1E3	109.5
O2A—C3A—C4A	117.4 (3)	H1E2—C1E—H1E3	109.5
O1A—C3A—C4A	116.5 (2)	C3E—N2E—C1E	112.1 (3)
C5A—C4A—O8A	110.4 (2)	C3E—N2E—H2E1	109.2
C5A—C4A—C3A	131.8 (3)	C1E—N2E—H2E1	109.2
O8A—C4A—C3A	117.7 (3)	C3E—N2E—H2E2	109.2
C4A—C5A—C6A	106.2 (3)	C1E—N2E—H2E2	109.2
C4A—C5A—H5A	126.9	H2E1—N2E—H2E2	107.9
C6A—C5A—H5A	126.9	N2E—C3E—H3E1	109.5
C7A—C6A—C5A	106.9 (3)	N2E—C3E—H3E2	109.5
C7A—C6A—H6A	126.6	H3E1—C3E—H3E2	109.5
C5A—C6A—H6A	126.6	N2E—C3E—H3E3	109.5
C6A—C7A—O8A	110.3 (2)	H3E1—C3E—H3E3	109.5
C6A—C7A—C9A	132.1 (3)	H3E2—C3E—H3E3	109.5
O8A—C7A—C9A	117.5 (3)	N2F—C1F—H1F1	109.5
C4A—O8A—C7A	106.3 (2)	N2F—C1F—H1F2	109.5
O10A—C9A—O11A	126.2 (3)	H1F1—C1F—H1F2	109.5
O10A—C9A—C7A	117.0 (3)	N2F—C1F—H1F3	109.5
O11A—C9A—C7A	116.8 (2)	H1F1—C1F—H1F3	109.5
C9A—O11A—Zn2	113.20 (18)	H1F2—C1F—H1F3	109.5
C3B—O1B—Zn1	114.89 (18)	C3F—N2F—C1F	112.2 (3)
O2B—C3B—O1B	126.0 (3)	C3F—N2F—H2F1	109.2
O2B—C3B—C4B	117.3 (3)	C1F—N2F—H2F1	109.2
O1B—C3B—C4B	116.7 (2)	C3F—N2F—H2F2	109.2
C5B—C4B—O8B	110.4 (2)	C1F—N2F—H2F2	109.2
C5B—C4B—C3B	131.9 (3)	H2F1—N2F—H2F2	107.9
O8B—C4B—C3B	117.6 (2)	N2F—C3F—H3F1	109.5
C4B—C5B—C6B	106.5 (2)	N2F—C3F—H3F2	109.5
C4B—C5B—H5B	126.8	H3F1—C3F—H3F2	109.5
C6B—C5B—H5B	126.8	N2F—C3F—H3F3	109.5
C7B—C6B—C5B	106.5 (2)	H3F1—C3F—H3F3	109.5
C7B—C6B—H6B	126.7	H3F2—C3F—H3F3	109.5
C5B—C6B—H6B	126.7	N2G—C1G—H1G1	109.5
C6B—C7B—O8B	110.4 (2)	N2G—C1G—H1G2	109.5
C6B—C7B—C9B	131.8 (3)	H1G1—C1G—H1G2	109.5
O8B—C7B—C9B	117.6 (2)	N2G—C1G—H1G3	109.5
C7B—O8B—C4B	106.3 (2)	H1G1—C1G—H1G3	109.5
O10B—C9B—O11B	126.3 (3)	H1G2—C1G—H1G3	109.5
O10B—C9B—C7B	117.0 (3)	C1G—N2G—C3G	112.1 (3)
O11B—C9B—C7B	116.7 (2)	C1G—N2G—H2G1	109.2
C9B—O11B—Zn3	112.81 (18)	C3G—N2G—H2G1	109.2
C3C—O1C—Zn1	114.84 (18)	C1G—N2G—H2G2	109.2
O2C—C3C—O1C	126.1 (3)	C3G—N2G—H2G2	109.2
O2C—C3C—C4C	117.2 (3)	H2G1—N2G—H2G2	107.9
O1C—C3C—C4C	116.7 (2)	N2G—C3G—H3G1	109.5
C5C—C4C—O8C	110.4 (2)	N2G—C3G—H3G2	109.5
C5C—C4C—C3C	131.8 (3)	H3G1—C3G—H3G2	109.5
O8C—C4C—C3C	117.7 (2)	N2G—C3G—H3G3	109.5
C4C—C5C—C6C	106.3 (2)	H3G1—C3G—H3G3	109.5
C4C—C5C—H5C	126.8	H3G2—C3G—H3G3	109.5
C6C—C5C—H5C	126.8	N2H—C1H—H1H1	109.5
C7C—C6C—C5C	106.8 (2)	N2H—C1H—H1H2	109.5
C7C—C6C—H6C	126.6	H1H1—C1H—H1H2	109.5
C5C—C6C—H6C	126.6	N2H—C1H—H1H3	109.5
C6C—C7C—O8C	110.1 (2)	H1H1—C1H—H1H3	109.5
C6C—C7C—C9C	132.1 (3)	H1H2—C1H—H1H3	109.5
O8C—C7C—C9C	117.7 (2)	C1H—N2H—C3H	112.0 (3)
C4C—O8C—C7C	106.4 (2)	C1H—N2H—H2H1	109.2
O10C—C9C—O11C	125.8 (3)	C3H—N2H—H2H1	109.2
O10C—C9C—C7C	117.2 (3)	C1H—N2H—H2H2	109.2
O11C—C9C—C7C	117.0 (2)	C3H—N2H—H2H2	109.2
C9C—O11C—Zn2^vi	112.85 (18)	H2H1—N2H—H2H2	107.9
C3D—O1D—Zn1	114.53 (18)	N2H—C3H—H3H1	109.5
O2D—C3D—O1D	125.9 (3)	N2H—C3H—H3H2	109.5
O2D—C3D—C4D	117.3 (3)	H3H1—C3H—H3H2	109.5
O1D—C3D—C4D	116.7 (2)	N2H—C3H—H3H3	109.5
C5D—C4D—O8D	110.5 (2)	H3H1—C3H—H3H3	109.5
C5D—C4D—C3D	131.5 (3)	H3H2—C3H—H3H3	109.5
Zn1—O1A—C3A—O2A	10.5 (4)	Zn1—O1C—C3C—O2C	10.4 (4)
Zn1—O1A—C3A—C4A	−168.86 (18)	Zn1—O1C—C3C—C4C	−169.57 (18)
O2A—C3A—C4A—C5A	1.2 (5)	O2C—C3C—C4C—C5C	0.6 (5)
O1A—C3A—C4A—C5A	−179.4 (3)	O1C—C3C—C4C—C5C	−179.5 (3)
O2A—C3A—C4A—O8A	−174.6 (2)	O2C—C3C—C4C—O8C	−176.2 (2)
O1A—C3A—C4A—O8A	4.9 (4)	O1C—C3C—C4C—O8C	3.8 (4)
O8A—C4A—C5A—C6A	0.0 (4)	O8C—C4C—C5C—C6C	0.2 (3)
C3A—C4A—C5A—C6A	−176.0 (3)	C3C—C4C—C5C—C6C	−176.8 (3)
C4A—C5A—C6A—C7A	−0.1 (4)	C4C—C5C—C6C—C7C	−0.2 (3)
C5A—C6A—C7A—O8A	0.2 (4)	C5C—C6C—C7C—O8C	0.2 (3)
C5A—C6A—C7A—C9A	176.4 (3)	C5C—C6C—C7C—C9C	175.3 (3)
C5A—C4A—O8A—C7A	0.1 (3)	C5C—C4C—O8C—C7C	0.0 (3)
C3A—C4A—O8A—C7A	176.7 (2)	C3C—C4C—O8C—C7C	177.4 (2)
C6A—C7A—O8A—C4A	−0.2 (3)	C6C—C7C—O8C—C4C	−0.1 (3)
C9A—C7A—O8A—C4A	−177.0 (2)	C9C—C7C—O8C—C4C	−176.0 (2)
C6A—C7A—C9A—O10A	−2.1 (5)	C6C—C7C—C9C—O10C	−2.2 (5)
O8A—C7A—C9A—O10A	173.8 (2)	O8C—C7C—C9C—O10C	172.6 (2)
C6A—C7A—C9A—O11A	178.4 (3)	C6C—C7C—C9C—O11C	178.4 (3)
O8A—C7A—C9A—O11A	−5.6 (4)	O8C—C7C—C9C—O11C	−6.8 (4)
O10A—C9A—O11A—Zn2	−12.5 (4)	O10C—C9C—O11C—Zn2^vi	−12.3 (4)
C7A—C9A—O11A—Zn2	166.93 (18)	C7C—C9C—O11C—Zn2^vi	166.96 (19)
Zn1—O1B—C3B—O2B	−10.7 (4)	Zn1—O1D—C3D—O2D	−10.2 (4)
Zn1—O1B—C3B—C4B	169.09 (18)	Zn1—O1D—C3D—C4D	169.30 (18)
O2B—C3B—C4B—C5B	−1.7 (5)	O2D—C3D—C4D—C5D	−0.4 (5)
O1B—C3B—C4B—C5B	178.5 (3)	O1D—C3D—C4D—C5D	−180.0 (3)
O2B—C3B—C4B—O8B	175.6 (2)	O2D—C3D—C4D—O8D	175.6 (2)
O1B—C3B—C4B—O8B	−4.2 (4)	O1D—C3D—C4D—O8D	−3.9 (4)
O8B—C4B—C5B—C6B	−0.4 (3)	O8D—C4D—C5D—C6D	−0.6 (4)
C3B—C4B—C5B—C6B	177.0 (3)	C3D—C4D—C5D—C6D	175.7 (3)
C4B—C5B—C6B—C7B	0.4 (3)	C4D—C5D—C6D—C7D	0.6 (4)
C5B—C6B—C7B—O8B	−0.2 (3)	C5D—C6D—C7D—O8D	−0.3 (4)
C5B—C6B—C7B—C9B	−175.4 (3)	C5D—C6D—C7D—C9D	−176.8 (3)
C6B—C7B—O8B—C4B	0.0 (3)	C5D—C4D—O8D—C7D	0.4 (3)
C9B—C7B—O8B—C4B	175.9 (2)	C3D—C4D—O8D—C7D	−176.4 (2)
C5B—C4B—O8B—C7B	0.2 (3)	C6D—C7D—O8D—C4D	0.0 (3)
C3B—C4B—O8B—C7B	−177.6 (2)	C9D—C7D—O8D—C4D	177.0 (2)
C6B—C7B—C9B—O10B	1.5 (5)	C6D—C7D—C9D—O10D	2.6 (5)
O8B—C7B—C9B—O10B	−173.4 (2)	O8D—C7D—C9D—O10D	−173.6 (2)
C6B—C7B—C9B—O11B	−178.9 (3)	C6D—C7D—C9D—O11D	−178.0 (3)
O8B—C7B—C9B—O11B	6.3 (4)	O8D—C7D—C9D—O11D	5.8 (4)
O10B—C9B—O11B—Zn3	12.8 (4)	O10D—C9D—O11D—Zn3^vii	12.5 (4)
C7B—C9B—O11B—Zn3	−166.81 (18)	C7D—C9D—O11D—Zn3^vii	−166.86 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2E—H2E1···O10A^i	0.91	2.21	2.915 (3)	134
N2E—H2E1···O2D^viii	0.91	2.13	2.899 (3)	141
N2E—H2E2···O2B	0.91	2.12	2.864 (3)	138
N2E—H2E2···O2B^viii	0.91	2.22	2.926 (4)	134
N2F—H2F1···O2A^ix	0.91	2.12	2.893 (3)	142
N2F—H2F1···O10D^ii	0.91	2.23	2.926 (3)	133
N2F—H2F2···O2C	0.91	2.11	2.858 (3)	139
N2F—H2F2···O2C^ix	0.91	2.22	2.927 (4)	134
N2G—H2G1···O10C^iv	0.91	2.23	2.932 (3)	133
N2G—H2G1···O10C^x	0.91	2.12	2.891 (4)	142
N2G—H2G2···O10A^xi	0.91	2.22	2.922 (4)	134
N2G—H2G2···O2D	0.91	2.12	2.867 (3)	139
N2H—H2H1···O10B^xii	0.91	2.22	2.928 (3)	134
N2H—H2H1···O10B^xiii	0.91	2.12	2.886 (4)	141
N2H—H2H2···O2A	0.91	2.13	2.872 (3)	138
N2H—H2H2···O10D^xiv	0.91	2.21	2.918 (4)	134

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iv) −x, y, −z+1/2; (viii) −x+1/2, −y+1/2, −z; (ix) −x+1/2, −y+1/2, −z+1; (x) x, −y+1, z−1/2; (xi) x−1/2, −y+1/2, z−1/2; (xii) −x+1/2, y+1/2, −z+1/2; (xiii) x+1/2, −y+1/2, z+1/2; (xiv) x, −y+1, z+1/2.

Poly[bis(dimethylazanium) [bis(µ₄-furan-2,5-dicarboxylato-κO²:κO^2':κO⁵:κO⁵)bis(µ₃-furan-2,5-dicarboxylato-κO²:κO^2':κO⁵)dizinc(II)] dimethylformamide 3.08-solvate] (2)

Crystal data

(C2H8N)2[Zn2(C6H2O5)4]·3.08C3H7NO	F(000) = 1159
Mr = 1130.50	Dx = 1.508 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.2803 (3) Å	Cell parameters from 17707 reflections
b = 15.1916 (5) Å	θ = 2.2–31.7°
c = 17.7731 (6) Å	µ = 1.52 mm^−1
β = 96.4221 (6)°	T = 150 K
V = 2489.97 (14) Å^3	Block, colourless
Z = 2	0.33 × 0.30 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer	7255 independent reflections
Radiation source: sealed tube	6472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.333 pixels mm^-1	θmax = 30.0°, θmin = 1.8°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −21→20
Tmin = 0.605, Tmax = 0.796	l = −24→24
41068 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0119P)^2 + 11.1698P] where P = (Fo^2 + 2Fc^2)/3
7255 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 1.76 e Å^−3
121 restraints	Δρmin = −1.18 e Å^−3

Special details

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. DMA counter ion and DMF solvent molecule are disordered in 2 orientations and were refined with geometric and atomic displacement parameters restrained to be similar. ADPs are also restrained to correspond to rigid body motions.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.500000	0.500000	1.000000	0.02270 (11)
Zn2	0.42599 (3)	0.61076 (2)	0.83985 (2)	0.02074 (8)
O1A	0.3026 (2)	0.46504 (15)	0.94902 (13)	0.0281 (5)
O2A	0.2326 (2)	0.57061 (16)	0.86327 (12)	0.0285 (5)
C3A	0.2101 (3)	0.5076 (2)	0.90644 (16)	0.0240 (6)
C4A	0.0572 (3)	0.4795 (2)	0.90756 (16)	0.0241 (6)
C5A	−0.0023 (3)	0.4055 (2)	0.93325 (19)	0.0293 (6)
H5A	0.047939	0.355376	0.954731	0.035*
C6A	−0.1553 (3)	0.4177 (2)	0.92162 (18)	0.0285 (6)
H6A	−0.227587	0.377337	0.933539	0.034*
O8A	−0.0480 (2)	0.53740 (15)	0.87952 (11)	0.0236 (4)
C9A	−0.3087 (3)	0.5513 (2)	0.86701 (16)	0.0235 (5)
C7A	−0.1772 (3)	0.4985 (2)	0.89015 (16)	0.0231 (5)
O10A	−0.4299 (2)	0.52153 (15)	0.88787 (12)	0.0241 (4)
O11A	−0.3037 (2)	0.61822 (17)	0.82919 (13)	0.0323 (5)
O1B	0.3871 (4)	0.5295 (2)	0.71541 (18)	0.0609 (9)
O2B	0.4031 (3)	0.6704 (2)	0.73894 (13)	0.0434 (7)
C3B	0.3940 (4)	0.6060 (3)	0.69386 (19)	0.0401 (9)
C4B	0.3949 (4)	0.6244 (2)	0.61219 (18)	0.0317 (7)
C5B	0.3848 (5)	0.5702 (3)	0.5522 (2)	0.0412 (8)
H5B	0.370363	0.508294	0.552333	0.049*
C6B	0.4002 (5)	0.6242 (2)	0.48841 (19)	0.0390 (8)
H6B	0.397570	0.605338	0.437309	0.047*
C7B	0.4194 (3)	0.7075 (2)	0.51421 (16)	0.0268 (6)
O8B	0.4160 (2)	0.70942 (16)	0.59083 (11)	0.0272 (4)
C9B	0.4401 (3)	0.7915 (2)	0.47440 (16)	0.0241 (5)
O10B	0.4452 (3)	0.78259 (15)	0.40358 (12)	0.0296 (5)
O11B	0.4473 (2)	0.86162 (15)	0.51109 (12)	0.0262 (4)
C1C	0.6353 (7)	0.8458 (5)	0.7049 (4)	0.0629 (17)	0.776 (7)
H1C1	0.574893	0.841455	0.656112	0.094*	0.776 (7)
H1C2	0.713651	0.802335	0.706710	0.094*	0.776 (7)
H1C3	0.676770	0.905024	0.710651	0.094*	0.776 (7)
C2C	0.3980 (7)	0.8689 (4)	0.7584 (4)	0.0643 (18)	0.776 (7)
H2C1	0.404820	0.931417	0.772102	0.096*	0.776 (7)
H2C2	0.340689	0.837935	0.793168	0.096*	0.776 (7)
H2C3	0.351019	0.862963	0.706472	0.096*	0.776 (7)
N1C	0.5499 (8)	0.8293 (5)	0.7638 (5)	0.0759 (18)	0.776 (7)
H1C4	0.599909	0.848799	0.807604	0.091*	0.776 (7)
H1C5	0.540948	0.769899	0.768106	0.091*	0.776 (7)
C1D	0.663 (2)	0.8323 (12)	0.8278 (11)	0.047 (4)	0.224 (7)
H1D1	0.701489	0.777449	0.809192	0.071*	0.224 (7)
H1D2	0.647396	0.825368	0.881147	0.071*	0.224 (7)
H1D3	0.731375	0.880291	0.822767	0.071*	0.224 (7)
C2D	0.513 (3)	0.8508 (15)	0.6928 (12)	0.064 (4)	0.224 (7)
H2D1	0.506217	0.911345	0.673617	0.096*	0.224 (7)
H2D2	0.425525	0.818249	0.673642	0.096*	0.224 (7)
H2D3	0.598233	0.822119	0.675607	0.096*	0.224 (7)
N1D	0.529 (3)	0.852 (2)	0.7848 (15)	0.0759 (18)	0.224 (7)
H1D4	0.502397	0.906770	0.799058	0.091*	0.224 (7)
H1D5	0.462158	0.813818	0.799551	0.091*	0.224 (7)
C1E	0.9981 (9)	0.8863 (6)	0.9853 (5)	0.083 (3)	0.731 (6)
H1E1	1.056307	0.868246	1.032142	0.125*	0.731 (6)
H1E2	0.913595	0.919788	0.997668	0.125*	0.731 (6)
H1E3	1.056963	0.923268	0.955397	0.125*	0.731 (6)
C2E	1.0522 (9)	0.7540 (5)	0.9148 (5)	0.080 (3)	0.731 (6)
H2E1	1.106458	0.786446	0.879548	0.120*	0.731 (6)
H2E2	1.001875	0.704224	0.888397	0.120*	0.731 (6)
H2E3	1.119335	0.732054	0.957122	0.120*	0.731 (6)
N1E	0.9505 (6)	0.8100 (4)	0.9424 (4)	0.0672 (19)	0.731 (6)
C3E	0.8234 (8)	0.8076 (5)	0.9054 (6)	0.080 (3)	0.731 (6)
H3D	0.803362	0.757231	0.874286	0.096*	0.731 (6)
O1E	0.7253 (6)	0.8607 (4)	0.9045 (5)	0.101 (2)	0.731 (6)
C1F	0.7740 (8)	0.9140 (9)	0.1494 (6)	0.162 (5)	0.811 (6)
H1F1	0.770899	0.897919	0.095837	0.244*	0.811 (6)
H1F2	0.730440	0.972246	0.153730	0.244*	0.811 (6)
H1F3	0.719683	0.870457	0.175613	0.244*	0.811 (6)
C2F	0.9906 (8)	0.8380 (6)	0.2079 (5)	0.097 (3)	0.811 (6)
H2F1	1.080393	0.852086	0.240084	0.145*	0.811 (6)
H2F2	1.013422	0.803594	0.164185	0.145*	0.811 (6)
H2F3	0.926612	0.803778	0.237081	0.145*	0.811 (6)
N1F	0.9213 (6)	0.9158 (6)	0.1830 (4)	0.097 (2)	0.811 (6)
C3F	0.9796 (12)	0.9914 (7)	0.2006 (5)	0.111 (3)	0.811 (6)
H3F	1.076886	0.989030	0.223786	0.133*	0.811 (6)
O1F	0.9289 (12)	1.0651 (6)	0.1920 (6)	0.179 (4)	0.811 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0159 (2)	0.0302 (2)	0.0219 (2)	0.00078 (17)	0.00181 (16)	0.00438 (18)
Zn2	0.01996 (15)	0.02485 (16)	0.01738 (14)	0.00132 (12)	0.00194 (11)	0.00302 (12)
O1A	0.0160 (9)	0.0335 (12)	0.0344 (11)	0.0001 (8)	0.0006 (8)	0.0065 (9)
O2A	0.0179 (9)	0.0393 (13)	0.0287 (11)	0.0000 (9)	0.0037 (8)	0.0083 (9)
C3A	0.0150 (11)	0.0329 (15)	0.0245 (13)	0.0006 (10)	0.0037 (10)	−0.0006 (11)
C4A	0.0145 (11)	0.0337 (15)	0.0243 (13)	0.0016 (10)	0.0030 (10)	0.0014 (11)
C5A	0.0173 (12)	0.0344 (17)	0.0364 (16)	0.0021 (11)	0.0046 (11)	0.0046 (13)
C6A	0.0166 (12)	0.0355 (16)	0.0342 (16)	−0.0012 (11)	0.0056 (11)	0.0021 (13)
O8A	0.0129 (8)	0.0339 (11)	0.0242 (10)	0.0005 (8)	0.0029 (7)	0.0024 (8)
C9A	0.0162 (12)	0.0349 (15)	0.0196 (12)	0.0007 (11)	0.0027 (9)	−0.0029 (11)
C7A	0.0132 (11)	0.0349 (15)	0.0215 (12)	−0.0012 (10)	0.0036 (9)	−0.0012 (11)
O10A	0.0133 (8)	0.0341 (11)	0.0248 (10)	0.0012 (8)	0.0020 (7)	0.0008 (8)
O11A	0.0229 (10)	0.0402 (13)	0.0343 (12)	0.0035 (9)	0.0049 (9)	0.0090 (10)
O1B	0.068 (2)	0.071 (2)	0.0465 (17)	0.0187 (17)	0.0205 (15)	0.0339 (16)
O2B	0.0306 (12)	0.079 (2)	0.0201 (11)	−0.0048 (13)	0.0013 (9)	0.0108 (12)
C3B	0.0250 (15)	0.070 (3)	0.0259 (15)	0.0096 (16)	0.0064 (12)	0.0182 (17)
C4B	0.0292 (15)	0.0417 (19)	0.0245 (14)	0.0048 (13)	0.0049 (11)	0.0098 (13)
C5B	0.058 (2)	0.0326 (18)	0.0345 (18)	0.0006 (16)	0.0115 (16)	0.0080 (14)
C6B	0.061 (2)	0.0328 (18)	0.0240 (15)	−0.0015 (16)	0.0087 (15)	0.0010 (13)
C7B	0.0308 (15)	0.0326 (16)	0.0174 (12)	0.0014 (12)	0.0046 (11)	0.0019 (11)
O8B	0.0258 (10)	0.0383 (12)	0.0174 (9)	0.0006 (9)	0.0030 (8)	0.0016 (8)
C9B	0.0198 (12)	0.0295 (15)	0.0234 (13)	0.0014 (11)	0.0042 (10)	0.0010 (11)
O10B	0.0402 (12)	0.0275 (11)	0.0224 (10)	0.0020 (9)	0.0093 (9)	0.0013 (8)
O11B	0.0222 (10)	0.0300 (11)	0.0267 (10)	0.0000 (8)	0.0041 (8)	−0.0031 (9)
C1C	0.061 (4)	0.060 (4)	0.066 (4)	−0.023 (3)	0.000 (3)	−0.022 (3)
C2C	0.066 (4)	0.054 (4)	0.068 (4)	−0.007 (3)	−0.010 (3)	0.019 (3)
N1C	0.074 (3)	0.070 (4)	0.079 (4)	−0.001 (3)	−0.013 (3)	−0.006 (3)
C1D	0.055 (8)	0.037 (8)	0.049 (8)	−0.012 (7)	0.001 (6)	0.011 (7)
C2D	0.075 (9)	0.049 (8)	0.062 (6)	0.006 (8)	−0.015 (7)	−0.008 (7)
N1D	0.074 (3)	0.070 (4)	0.079 (4)	−0.001 (3)	−0.013 (3)	−0.006 (3)
C1E	0.064 (5)	0.111 (7)	0.074 (5)	−0.028 (5)	0.006 (4)	−0.041 (5)
C2E	0.109 (7)	0.041 (4)	0.096 (6)	0.001 (4)	0.037 (5)	0.007 (4)
N1E	0.048 (3)	0.050 (3)	0.096 (5)	0.008 (2)	−0.028 (3)	−0.016 (3)
C3E	0.054 (4)	0.047 (4)	0.134 (8)	0.002 (3)	−0.008 (5)	−0.008 (4)
O1E	0.067 (4)	0.076 (4)	0.158 (7)	0.007 (3)	0.004 (4)	−0.012 (4)
C1F	0.049 (4)	0.323 (14)	0.111 (7)	−0.017 (6)	−0.009 (4)	0.119 (8)
C2F	0.065 (4)	0.145 (6)	0.077 (5)	−0.020 (5)	−0.004 (4)	−0.004 (5)
N1F	0.052 (3)	0.174 (6)	0.065 (4)	−0.018 (4)	0.006 (3)	0.033 (4)
C3F	0.139 (7)	0.134 (6)	0.062 (4)	0.022 (5)	0.020 (5)	0.034 (5)
O1F	0.224 (10)	0.168 (6)	0.155 (8)	0.049 (7)	0.064 (7)	0.061 (6)

Geometric parameters (Å, º)

Zn1—O1A^i	2.022 (2)	C1C—H1C3	0.9800
Zn1—O1A	2.022 (2)	C2C—N1C	1.526 (10)
Zn1—O11B^ii	2.172 (2)	C2C—H2C1	0.9800
Zn1—O11B^iii	2.172 (2)	C2C—H2C2	0.9800
Zn1—O10A^iv	2.189 (2)	C2C—H2C3	0.9800
Zn1—O10A^v	2.189 (2)	N1C—H1C4	0.9100
Zn2—O10B^ii	1.973 (2)	N1C—H1C5	0.9100
Zn2—O2A	1.984 (2)	C1D—N1D	1.41 (3)
Zn2—O2B	2.000 (2)	C1D—H1D1	0.9800
Zn2—O10A^iv	2.024 (2)	C1D—H1D2	0.9800
O1A—C3A	1.258 (4)	C1D—H1D3	0.9800
O2A—C3A	1.259 (4)	C2D—N1D	1.63 (3)
C3A—C4A	1.484 (4)	C2D—H2D1	0.9800
C4A—C5A	1.355 (4)	C2D—H2D2	0.9800
C4A—O8A	1.366 (3)	C2D—H2D3	0.9800
C5A—C6A	1.424 (4)	N1D—H1D4	0.9100
C5A—H5A	0.9500	N1D—H1D5	0.9100
C6A—C7A	1.355 (5)	C1E—N1E	1.430 (7)
C6A—H6A	0.9500	C1E—H1E1	0.9800
O8A—C7A	1.369 (3)	C1E—H1E2	0.9800
C9A—O11A	1.222 (4)	C1E—H1E3	0.9800
C9A—O10A	1.304 (3)	C2E—N1E	1.399 (8)
C9A—C7A	1.479 (4)	C2E—H2E1	0.9800
O1B—C3B	1.228 (5)	C2E—H2E2	0.9800
O2B—C3B	1.261 (5)	C2E—H2E3	0.9800
C3B—C4B	1.479 (4)	N1E—C3E	1.285 (8)
C4B—C5B	1.343 (5)	C3E—O1E	1.216 (8)
C4B—O8B	1.366 (4)	C3E—H3D	0.9500
C5B—C6B	1.419 (5)	C1F—N1F	1.429 (8)
C5B—H5B	0.9500	C1F—H1F1	0.9800
C6B—C7B	1.351 (5)	C1F—H1F2	0.9800
C6B—H6B	0.9500	C1F—H1F3	0.9800
C7B—O8B	1.366 (3)	C2F—N1F	1.393 (9)
C7B—C9B	1.482 (4)	C2F—H2F1	0.9800
C9B—O11B	1.247 (4)	C2F—H2F2	0.9800
C9B—O10B	1.272 (3)	C2F—H2F3	0.9800
C1C—N1C	1.405 (10)	N1F—C3F	1.293 (9)
C1C—H1C1	0.9800	C3F—O1F	1.218 (9)
C1C—H1C2	0.9800	C3F—H3F	0.9500
O1A^i—Zn1—O1A	180.0	N1C—C1C—H1C3	109.5
O1A^i—Zn1—O11B^ii	84.67 (9)	H1C1—C1C—H1C3	109.5
O1A—Zn1—O11B^ii	95.33 (9)	H1C2—C1C—H1C3	109.5
O1A^i—Zn1—O11B^iii	95.33 (9)	N1C—C2C—H2C1	109.5
O1A—Zn1—O11B^iii	84.67 (9)	N1C—C2C—H2C2	109.5
O11B^ii—Zn1—O11B^iii	180.0	H2C1—C2C—H2C2	109.5
O1A^i—Zn1—O10A^iv	91.28 (8)	N1C—C2C—H2C3	109.5
O1A—Zn1—O10A^iv	88.72 (8)	H2C1—C2C—H2C3	109.5
O11B^ii—Zn1—O10A^iv	91.77 (8)	H2C2—C2C—H2C3	109.5
O11B^iii—Zn1—O10A^iv	88.23 (8)	C1C—N1C—C2C	118.5 (7)
O1A^i—Zn1—O10A^v	88.72 (8)	C1C—N1C—H1C4	107.7
O1A—Zn1—O10A^v	91.28 (8)	C2C—N1C—H1C4	107.7
O11B^ii—Zn1—O10A^v	88.23 (8)	C1C—N1C—H1C5	107.7
O11B^iii—Zn1—O10A^v	91.77 (8)	C2C—N1C—H1C5	107.7
O10A^iv—Zn1—O10A^v	180.0	H1C4—N1C—H1C5	107.1
O10B^ii—Zn2—O2A	99.09 (10)	N1D—C1D—H1D1	109.5
O10B^ii—Zn2—O2B	97.84 (11)	N1D—C1D—H1D2	109.5
O2A—Zn2—O2B	108.65 (10)	H1D1—C1D—H1D2	109.5
O10B^ii—Zn2—O10A^iv	107.14 (9)	N1D—C1D—H1D3	109.5
O2A—Zn2—O10A^iv	106.03 (9)	H1D1—C1D—H1D3	109.5
O2B—Zn2—O10A^iv	132.89 (10)	H1D2—C1D—H1D3	109.5
C3A—O1A—Zn1	131.1 (2)	N1D—C2D—H2D1	109.5
C3A—O2A—Zn2	125.26 (19)	N1D—C2D—H2D2	109.5
O1A—C3A—O2A	127.5 (3)	H2D1—C2D—H2D2	109.5
O1A—C3A—C4A	115.7 (3)	N1D—C2D—H2D3	109.5
O2A—C3A—C4A	116.8 (3)	H2D1—C2D—H2D3	109.5
C5A—C4A—O8A	110.8 (2)	H2D2—C2D—H2D3	109.5
C5A—C4A—C3A	132.1 (3)	C1D—N1D—C2D	121 (2)
O8A—C4A—C3A	117.1 (3)	C1D—N1D—H1D4	107.1
C4A—C5A—C6A	106.3 (3)	C2D—N1D—H1D4	107.1
C4A—C5A—H5A	126.9	C1D—N1D—H1D5	107.1
C6A—C5A—H5A	126.9	C2D—N1D—H1D5	107.1
C7A—C6A—C5A	106.2 (3)	H1D4—N1D—H1D5	106.8
C7A—C6A—H6A	126.9	N1E—C1E—H1E1	109.5
C5A—C6A—H6A	126.9	N1E—C1E—H1E2	109.5
C4A—O8A—C7A	105.9 (2)	H1E1—C1E—H1E2	109.5
O11A—C9A—O10A	122.2 (3)	N1E—C1E—H1E3	109.5
O11A—C9A—C7A	121.5 (3)	H1E1—C1E—H1E3	109.5
O10A—C9A—C7A	116.4 (3)	H1E2—C1E—H1E3	109.5
C6A—C7A—O8A	110.8 (2)	N1E—C2E—H2E1	109.5
C6A—C7A—C9A	133.4 (3)	N1E—C2E—H2E2	109.5
O8A—C7A—C9A	115.9 (3)	H2E1—C2E—H2E2	109.5
C9A—O10A—Zn2^vi	101.42 (18)	N1E—C2E—H2E3	109.5
C9A—O10A—Zn1^vi	131.61 (18)	H2E1—C2E—H2E3	109.5
Zn2^vi—O10A—Zn1^vi	103.56 (9)	H2E2—C2E—H2E3	109.5
C3B—O2B—Zn2	102.2 (2)	C3E—N1E—C2E	114.8 (7)
O1B—C3B—O2B	122.6 (3)	C3E—N1E—C1E	120.4 (6)
O1B—C3B—C4B	119.4 (4)	C2E—N1E—C1E	120.0 (6)
O2B—C3B—C4B	118.0 (4)	O1E—C3E—N1E	129.1 (8)
C5B—C4B—O8B	111.0 (3)	O1E—C3E—H3D	115.4
C5B—C4B—C3B	131.0 (4)	N1E—C3E—H3D	115.4
O8B—C4B—C3B	117.9 (3)	N1F—C1F—H1F1	109.5
C4B—C5B—C6B	106.0 (3)	N1F—C1F—H1F2	109.5
C4B—C5B—H5B	127.0	H1F1—C1F—H1F2	109.5
C6B—C5B—H5B	127.0	N1F—C1F—H1F3	109.5
C7B—C6B—C5B	107.0 (3)	H1F1—C1F—H1F3	109.5
C7B—C6B—H6B	126.5	H1F2—C1F—H1F3	109.5
C5B—C6B—H6B	126.5	N1F—C2F—H2F1	109.5
C6B—C7B—O8B	109.9 (3)	N1F—C2F—H2F2	109.5
C6B—C7B—C9B	131.6 (3)	H2F1—C2F—H2F2	109.5
O8B—C7B—C9B	118.5 (3)	N1F—C2F—H2F3	109.5
C4B—O8B—C7B	106.1 (3)	H2F1—C2F—H2F3	109.5
O11B—C9B—O10B	127.0 (3)	H2F2—C2F—H2F3	109.5
O11B—C9B—C7B	119.2 (3)	C3F—N1F—C2F	120.7 (7)
O10B—C9B—C7B	113.7 (3)	C3F—N1F—C1F	118.3 (9)
C9B—O10B—Zn2^vii	118.0 (2)	C2F—N1F—C1F	120.1 (8)
C9B—O11B—Zn1^viii	141.2 (2)	O1F—C3F—N1F	129.9 (11)
N1C—C1C—H1C1	109.5	O1F—C3F—H3F	115.1
N1C—C1C—H1C2	109.5	N1F—C3F—H3F	115.1
H1C1—C1C—H1C2	109.5
Zn1—O1A—C3A—O2A	27.3 (5)	Zn2—O2B—C3B—C4B	−172.2 (2)
Zn1—O1A—C3A—C4A	−152.9 (2)	O1B—C3B—C4B—C5B	2.3 (6)
Zn2—O2A—C3A—O1A	8.7 (5)	O2B—C3B—C4B—C5B	−179.0 (4)
Zn2—O2A—C3A—C4A	−171.1 (2)	O1B—C3B—C4B—O8B	−174.1 (3)
O1A—C3A—C4A—C5A	−16.0 (5)	O2B—C3B—C4B—O8B	4.6 (5)
O2A—C3A—C4A—C5A	163.8 (3)	O8B—C4B—C5B—C6B	−0.1 (4)
O1A—C3A—C4A—O8A	162.4 (3)	C3B—C4B—C5B—C6B	−176.7 (4)
O2A—C3A—C4A—O8A	−17.8 (4)	C4B—C5B—C6B—C7B	0.3 (5)
O8A—C4A—C5A—C6A	−0.8 (4)	C5B—C6B—C7B—O8B	−0.4 (4)
C3A—C4A—C5A—C6A	177.7 (3)	C5B—C6B—C7B—C9B	−179.5 (3)
C4A—C5A—C6A—C7A	−0.4 (4)	C5B—C4B—O8B—C7B	−0.1 (4)
C5A—C4A—O8A—C7A	1.6 (3)	C3B—C4B—O8B—C7B	177.0 (3)
C3A—C4A—O8A—C7A	−177.1 (2)	C6B—C7B—O8B—C4B	0.3 (4)
C5A—C6A—C7A—O8A	1.4 (4)	C9B—C7B—O8B—C4B	179.6 (3)
C5A—C6A—C7A—C9A	−177.6 (3)	C6B—C7B—C9B—O11B	175.9 (4)
C4A—O8A—C7A—C6A	−1.8 (3)	O8B—C7B—C9B—O11B	−3.2 (4)
C4A—O8A—C7A—C9A	177.3 (2)	C6B—C7B—C9B—O10B	−2.6 (5)
O11A—C9A—C7A—C6A	−169.0 (3)	O8B—C7B—C9B—O10B	178.4 (3)
O10A—C9A—C7A—C6A	9.7 (5)	O11B—C9B—O10B—Zn2^vii	−12.5 (4)
O11A—C9A—C7A—O8A	12.1 (4)	C7B—C9B—O10B—Zn2^vii	165.9 (2)
O10A—C9A—C7A—O8A	−169.3 (2)	O10B—C9B—O11B—Zn1^viii	−11.9 (5)
O11A—C9A—O10A—Zn2^vi	1.1 (3)	C7B—C9B—O11B—Zn1^viii	169.9 (2)
C7A—C9A—O10A—Zn2^vi	−177.5 (2)	C2E—N1E—C3E—O1E	−161.5 (10)
O11A—C9A—O10A—Zn1^vi	−118.8 (3)	C1E—N1E—C3E—O1E	−6.1 (16)
C7A—C9A—O10A—Zn1^vi	62.5 (4)	C2F—N1F—C3F—O1F	−170.2 (10)
Zn2—O2B—C3B—O1B	6.5 (4)	C1F—N1F—C3F—O1F	−1.4 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1C(a)—H1C4(a)···O1E(a)	0.91	1.98	2.867 (11)	166
N1C(a)—H1C5(a)···O2B	0.91	2.01	2.782 (9)	142
N1D(b)—H1D4(b)···O1B^viii	0.91	2.16	2.81 (3)	127
N1D(b)—H1D5(b)···O2B	0.91	2.46	3.07 (3)	124
N1D(b)—H1D5(b)···O10B^ii	0.91	2.38	3.10 (3)	136

Symmetry codes: (ii) x, −y+3/2, z+1/2; (viii) −x+1, y+1/2, −z+3/2.