Poly[[bis­(dimethyl­formamide)[μ7-5,5′-(methyl­enedi­oxy)diisophthalato]dizinc] dimethyl­formamide monosolvate]

Li, C.-Q.; Qiu, W.-G.; He, H.

doi:10.1107/S1600536811037056

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1406

https://doi.org/10.1107/S1600536811037056

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Poly[[bis(dimethylformamide)[μ₇-5,5′-(methylenedioxy)diisophthalato]dizinc] dimethylformamide monosolvate]

Chuan-Qiang Li,^a Wen-Ge Qiu ^a ^* and Hong He ^a

^aCollege of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100124, People's Republic of China
^*Correspondence e-mail: qiuwenge@bjut.edu.cn

(Received 27 May 2011; accepted 13 September 2011; online 20 September 2011)

In the crystal structure of the title coordination polymer, {[Zn₂(C₁₇H₈O₁₀)(C₃H₇NO)₂]·C₃H₇NO}_n, the molecular building block (MBB), viz. {Zn₂(CO₂)₄(C₃H₇NO)₂}, comprises two zinc atoms, each bridged by three carboxylate groups. These two Zn atoms exhibit different coordination environments: a distorted coordination intermediate between trigonal–pyramidal, and square–pyramidal formed by the two coordinated dimethylformamide molecules and three carboxylate groups, and a distorted tetrahedral coordination defined by carboxylate groups of which three are bidentate bridging and the fourth is a monodentate ligand. Thus, each ligand connects four MBBs, forming the three-dimensional polymer.

Related literature

For the use of flexible multicarboxylate ligands as building blocks in the assembly of coordination frameworks, see: Kim et al. (2004 ); Zhu et al. (2005 ); Hawxwell et al. (2007 ). For the synthesis, see: Karmakar & Goldberg (2010 ).

Experimental

Crystal data

[Zn₂(C₁₇H₈O₁₀)(C₃H₇NO)₂]·C₃H₇NO
M_r = 722.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.2562 (6) Å
b = 13.1744 (7) Å
c = 20.3965 (12) Å
V = 3024.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.66 mm⁻¹
T = 173 K
0.15 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2008 ) T_min = 0.789, T_max = 0.814
15188 measured reflections
5261 independent reflections
5131 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.064
S = 1.07
5261 reflections
403 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ), 2298 Friedel pairs
Flack parameter: 0.010 (9)

Table 1
Selected bond lengths (Å)

Zn1—O10ⁱ	1.9779 (19)
Zn1—O4ⁱⁱ	2.010 (2)
Zn1—O11	2.030 (2)
Zn1—O2	2.052 (2)
Zn1—O12	2.073 (2)
Zn2—O8ⁱⁱⁱ	1.953 (2)
Zn2—O9ⁱ	1.966 (2)
Zn2—O3ⁱⁱ	1.967 (2)
Zn2—O1	1.986 (2)
Symmetry codes: (i) x, y+1, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037056/kp2331sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037056/kp2331Isup2.hkl

checkCIF report

Comment top

The use of flexible multicarboxylate ligands as building blocks in the assembly of coordination frameworks has been an attractive strategy because some conformational freedom of the ligand molecules may offer various possibilities for release of the steric strain imposed by the metal-ligand association and relaxation of the network architecture (Kim et al. 2004; Zhu et al. 2005). Herein we chose a flexible multicarboxylate ligand, 1,1-bis-[3,5-bis(carboxy) phenoxy]methane, reacted with zinc nitrate affording a new three-dimensional coordination polymer, namely the title compound, (I), [Zn(ii)₂(L)(DMF)₃]_n, where L=1,1-bis-[3,5-bis(carboxylato) phenoxy]methane, DMF=N,N-dimethyl formamide.

The molecular building blocks (MBBs) of the compound (I) comprise two zinc centres, in which the two Zn atoms are five-coordinated and four-coordinated respectively. The different coordination environments in the dinuclear zinc cluster (Fig. 1, Table 1) reveal the Zn1 centre coordinated by five oxygen atoms from three L ligands and two DMF molecules, while the Zn2 centre is coordinated by four oxygen atoms from four L ligands. A non-coordinated solvent molecule of DMF occupies the interstitial voids within the framework.

Related literature top

For the use of flexible multicarboxylate ligands as building blocks in the assembly of coordination frameworks, see: Kim et al. (2004); Zhu et al. (2005). For related literature [on what subject(s)?], see: Hawxwell et al. (2007). For the synthesis, see: Karmakar & Goldberg (2010).

Experimental top

The tetracarboxylic ligand, H₄L was synthesised using the literature method of Karmakar (2010). A mixture of zinc nitrate hexahydrate (0.02 mmol, 6 mg) and the H₄L ligand (0.01 mmol, 3.8 mg) in DMF (0.8 mL) was placed in a 5 mL sealed glass vial, and heated at 358 K for 72 h. Colourless crystals of the title compound were obtained after cooling to room temperature (yield of 52%, based on H₄L).

Structure description top

Computing details top

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

Figures top

	Fig. 1. Crystal structure of compound(1) with labeling and displacement ellipsoids drawn at the 30% probability level; the hydrogen atoms and DMF molecules have been omitted for clarity.
	Fig. 2. The perspective view of the polymeric structure. The hydrogen atoms and solvent moleculs have been omitted for clarity.

Poly[[bis(dimethylformamide)[µ₇-5,5'-(methylenedioxy)diisophthalato]dizinc] dimethylformamide monosolvate] top

Crystal data top

[Zn₂(C₁₇H₈O₁₀)(C₃H₇NO)₂]·C₃H₇NO	F(000) = 1480
M_r = 722.26	D_x = 1.586 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9981 reflections
a = 11.2562 (6) Å	θ = 2.4–28.2°
b = 13.1744 (7) Å	µ = 1.66 mm⁻¹
c = 20.3965 (12) Å	T = 173 K
V = 3024.7 (3) Å³	Block, colourless
Z = 4	0.15 × 0.14 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	5261 independent reflections
Radiation source: fine-focus sealed tube	5131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 2008)	h = −12→13
T_min = 0.789, T_max = 0.814	k = −15→12
15188 measured reflections	l = −16→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0225P)² + 2.9204P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
5261 reflections	Δρ_max = 1.02 e Å⁻³
403 parameters	Δρ_min = −0.51 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 2298 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (9)

Crystal data top

[Zn₂(C₁₇H₈O₁₀)(C₃H₇NO)₂]·C₃H₇NO	V = 3024.7 (3) Å³
M_r = 722.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.2562 (6) Å	µ = 1.66 mm⁻¹
b = 13.1744 (7) Å	T = 173 K
c = 20.3965 (12) Å	0.15 × 0.14 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	5261 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2008)	5131 reflections with I > 2σ(I)
T_min = 0.789, T_max = 0.814	R_int = 0.022
15188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	Δρ_max = 1.02 e Å⁻³
S = 1.07	Δρ_min = −0.51 e Å⁻³
5261 reflections	Absolute structure: Flack (1983), 2298 Friedel pairs
403 parameters	Absolute structure parameter: 0.010 (9)
7 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.32282 (3)	1.02153 (3)	0.532246 (16)	0.01304 (8)
Zn2	0.11040 (3)	0.92795 (2)	0.640664 (15)	0.01034 (8)
O1	0.25310 (18)	0.84177 (15)	0.65422 (10)	0.0142 (4)
O2	0.3248 (2)	0.86905 (15)	0.55265 (10)	0.0186 (5)
O3	0.55588 (18)	0.60034 (16)	0.44912 (10)	0.0173 (5)
O4	0.6626 (2)	0.49210 (16)	0.51036 (10)	0.0226 (5)
O5	0.48922 (18)	0.55461 (15)	0.74102 (10)	0.0141 (4)
O6	0.51506 (17)	0.38160 (16)	0.71297 (10)	0.0142 (4)
O7	0.13001 (19)	0.47767 (17)	0.83474 (11)	0.0232 (5)
O8	0.00425 (18)	0.35644 (16)	0.80428 (10)	0.0157 (4)
O9	0.14499 (16)	0.06646 (15)	0.67100 (10)	0.0151 (4)
O10	0.32214 (19)	0.08120 (16)	0.62123 (9)	0.0166 (4)
O11	0.5015 (2)	1.0047 (2)	0.52425 (14)	0.0353 (6)
O12	0.3428 (2)	1.15866 (19)	0.48368 (12)	0.0306 (6)
O13	0.3138 (3)	1.0302 (2)	0.33443 (15)	0.0499 (7)
N1	0.6865 (3)	1.0308 (3)	0.48390 (18)	0.0495 (8)
N2	0.3226 (3)	1.2560 (2)	0.39360 (14)	0.0247 (6)
N3	0.4694 (3)	0.9184 (2)	0.35115 (14)	0.0322 (7)
C1	0.4858 (3)	0.5963 (2)	0.67844 (14)	0.0138 (6)
C2	0.4123 (3)	0.6810 (2)	0.67289 (14)	0.0137 (6)
H2	0.3707	0.7057	0.7101	0.016*
C3	0.4002 (3)	0.7295 (2)	0.61255 (14)	0.0137 (6)
C4	0.4597 (3)	0.6924 (2)	0.55776 (15)	0.0146 (6)
H4	0.4517	0.7256	0.5167	0.018*
C5	0.5308 (3)	0.6065 (2)	0.56331 (15)	0.0141 (6)
C6	0.5468 (3)	0.5589 (2)	0.62467 (14)	0.0126 (6)
H6	0.5986	0.5023	0.6290	0.015*
C7	0.3202 (3)	0.8206 (2)	0.60605 (14)	0.0130 (6)
C8	0.5879 (2)	0.5635 (2)	0.50290 (14)	0.0149 (6)
C9	0.5557 (3)	0.4640 (2)	0.75127 (14)	0.0148 (6)
H9A	0.6401	0.4772	0.7407	0.018*
H9B	0.5511	0.4452	0.7982	0.018*
C10	0.4025 (3)	0.3430 (2)	0.72419 (13)	0.0129 (6)
C11	0.3158 (3)	0.3889 (2)	0.76253 (14)	0.0139 (6)
H11	0.3324	0.4504	0.7851	0.017*
C12	0.2037 (3)	0.3435 (2)	0.76758 (14)	0.0136 (6)
C13	0.1795 (3)	0.2524 (2)	0.73604 (13)	0.0134 (6)
H13	0.1039	0.2212	0.7409	0.016*
C14	0.2666 (3)	0.2068 (2)	0.69721 (14)	0.0127 (6)
C15	0.3786 (3)	0.2523 (2)	0.69091 (14)	0.0126 (6)
H15	0.4379	0.2218	0.6642	0.015*
C16	0.1075 (3)	0.3978 (2)	0.80611 (13)	0.0144 (6)
C17	0.2425 (2)	0.1110 (2)	0.66028 (13)	0.0111 (6)
C18	0.5723 (3)	1.0484 (3)	0.4863 (2)	0.0432 (11)
H18	0.5409	1.0978	0.4571	0.052*
C19	0.7341 (6)	0.9558 (5)	0.5254 (3)	0.0816 (16)
H19A	0.6697	0.9236	0.5502	0.122*
H19B	0.7906	0.9871	0.5558	0.122*
H19C	0.7750	0.9045	0.4990	0.122*
C20	0.7647 (4)	1.0820 (5)	0.4373 (3)	0.0732 (17)
H20A	0.7176	1.1271	0.4093	0.110*
H20B	0.8049	1.0313	0.4100	0.110*
H20C	0.8240	1.1219	0.4612	0.110*
C21	0.2853 (3)	1.1867 (3)	0.43474 (17)	0.0240 (7)
H21	0.2103	1.1560	0.4268	0.029*
C22	0.2583 (4)	1.2772 (3)	0.3324 (2)	0.0437 (11)
H22A	0.3031	1.2496	0.2952	0.066*
H22B	0.2492	1.3507	0.3270	0.066*
H22C	0.1796	1.2453	0.3341	0.066*
C23	0.4417 (3)	1.2999 (3)	0.3995 (2)	0.0364 (10)
H23A	0.4678	1.2963	0.4453	0.055*
H23B	0.4399	1.3710	0.3853	0.055*
H23C	0.4972	1.2617	0.3718	0.055*
C24	0.4167 (3)	1.0000 (3)	0.32387 (19)	0.0347 (9)
H24	0.4628	1.0381	0.2936	0.042*
C25	0.4002 (5)	0.8543 (3)	0.3960 (2)	0.0493 (11)
H25A	0.3157	0.8708	0.3918	0.074*
H25B	0.4260	0.8666	0.4412	0.074*
H25C	0.4128	0.7827	0.3849	0.074*
C26	0.5865 (4)	0.8865 (4)	0.3345 (2)	0.0451 (10)
H26A	0.6201	0.9331	0.3019	0.068*
H26B	0.5837	0.8178	0.3163	0.068*
H26C	0.6364	0.8868	0.3739	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01357 (16)	0.01255 (16)	0.01301 (16)	−0.00049 (14)	0.00072 (13)	−0.00015 (14)
Zn2	0.01203 (15)	0.00882 (15)	0.01017 (15)	−0.00059 (13)	0.00052 (13)	−0.00001 (13)
O1	0.0166 (10)	0.0147 (10)	0.0114 (10)	0.0036 (8)	0.0003 (8)	−0.0023 (8)
O2	0.0252 (11)	0.0154 (11)	0.0153 (11)	0.0040 (10)	0.0024 (9)	0.0010 (8)
O3	0.0182 (10)	0.0207 (12)	0.0129 (10)	0.0038 (9)	0.0020 (9)	0.0006 (9)
O4	0.0282 (12)	0.0181 (12)	0.0215 (11)	0.0101 (10)	0.0129 (9)	0.0061 (9)
O5	0.0210 (10)	0.0110 (11)	0.0102 (10)	0.0011 (8)	0.0001 (8)	0.0012 (8)
O6	0.0106 (10)	0.0111 (10)	0.0209 (11)	−0.0012 (8)	0.0009 (8)	−0.0023 (9)
O7	0.0230 (11)	0.0171 (11)	0.0296 (12)	0.0006 (10)	0.0042 (9)	−0.0094 (11)
O8	0.0152 (10)	0.0145 (11)	0.0175 (11)	0.0009 (9)	0.0041 (8)	−0.0011 (9)
O9	0.0145 (10)	0.0104 (10)	0.0203 (10)	−0.0009 (8)	0.0005 (8)	−0.0030 (9)
O10	0.0182 (10)	0.0173 (10)	0.0143 (10)	0.0026 (10)	0.0014 (9)	−0.0050 (8)
O11	0.0201 (12)	0.0384 (16)	0.0474 (16)	0.0026 (11)	0.0074 (11)	0.0003 (13)
O12	0.0300 (13)	0.0318 (13)	0.0301 (13)	−0.0156 (11)	−0.0114 (11)	0.0180 (11)
O13	0.0426 (16)	0.0524 (18)	0.0548 (18)	0.0067 (16)	0.0051 (15)	0.0042 (15)
N1	0.0242 (16)	0.074 (2)	0.050 (2)	−0.0051 (17)	0.0078 (15)	−0.0203 (16)
N2	0.0297 (15)	0.0177 (14)	0.0266 (15)	−0.0068 (13)	−0.0030 (13)	0.0092 (12)
N3	0.0499 (19)	0.0250 (16)	0.0216 (15)	−0.0043 (14)	0.0147 (14)	0.0027 (13)
C1	0.0152 (14)	0.0117 (15)	0.0145 (15)	−0.0040 (11)	−0.0043 (12)	0.0008 (11)
C2	0.0153 (15)	0.0124 (14)	0.0134 (14)	−0.0011 (12)	0.0024 (12)	−0.0015 (11)
C3	0.0150 (14)	0.0107 (14)	0.0154 (14)	−0.0014 (12)	0.0012 (12)	−0.0002 (11)
C4	0.0156 (14)	0.0165 (15)	0.0117 (13)	0.0011 (12)	0.0003 (12)	0.0025 (12)
C5	0.0114 (14)	0.0139 (15)	0.0172 (15)	−0.0003 (11)	0.0016 (12)	−0.0001 (12)
C6	0.0130 (13)	0.0091 (14)	0.0157 (15)	0.0006 (11)	0.0001 (11)	−0.0019 (11)
C7	0.0135 (14)	0.0115 (14)	0.0140 (14)	0.0004 (12)	−0.0003 (13)	−0.0005 (11)
C8	0.0136 (14)	0.0130 (14)	0.0181 (15)	−0.0019 (13)	0.0064 (12)	0.0006 (12)
C9	0.0198 (14)	0.0093 (15)	0.0154 (14)	0.0003 (12)	−0.0062 (12)	0.0026 (12)
C10	0.0135 (14)	0.0110 (14)	0.0142 (14)	0.0002 (12)	−0.0021 (12)	0.0032 (11)
C11	0.0170 (15)	0.0103 (13)	0.0145 (14)	−0.0026 (12)	0.0000 (12)	−0.0004 (11)
C12	0.0170 (15)	0.0126 (14)	0.0111 (14)	0.0029 (12)	0.0012 (11)	0.0008 (11)
C13	0.0126 (14)	0.0144 (14)	0.0131 (14)	0.0002 (12)	−0.0009 (12)	0.0011 (11)
C14	0.0167 (14)	0.0115 (14)	0.0100 (14)	0.0031 (12)	−0.0020 (12)	0.0022 (12)
C15	0.0140 (14)	0.0124 (14)	0.0113 (13)	0.0038 (12)	−0.0003 (12)	−0.0014 (11)
C16	0.0179 (14)	0.0137 (14)	0.0116 (13)	0.0016 (12)	−0.0007 (13)	0.0003 (11)
C17	0.0145 (15)	0.0087 (14)	0.0101 (13)	0.0022 (11)	−0.0023 (11)	0.0030 (11)
C18	0.0231 (19)	0.036 (2)	0.071 (3)	−0.0021 (16)	0.0152 (19)	−0.006 (2)
C19	0.0789 (18)	0.0864 (18)	0.0795 (18)	0.0028 (10)	0.0012 (10)	0.0001 (10)
C20	0.037 (2)	0.086 (4)	0.097 (4)	−0.020 (3)	0.032 (3)	−0.026 (4)
C21	0.0234 (17)	0.0222 (17)	0.0265 (18)	−0.0087 (14)	−0.0017 (14)	0.0063 (15)
C22	0.054 (3)	0.037 (2)	0.040 (2)	−0.015 (2)	−0.021 (2)	0.0180 (19)
C23	0.030 (2)	0.030 (2)	0.050 (2)	−0.0078 (16)	−0.0021 (18)	0.0211 (18)
C24	0.037 (2)	0.035 (2)	0.032 (2)	0.0023 (16)	0.0013 (16)	0.0007 (16)
C25	0.071 (3)	0.043 (2)	0.034 (2)	0.003 (2)	0.017 (2)	0.0046 (19)
C26	0.032 (2)	0.042 (2)	0.061 (3)	−0.0001 (18)	0.003 (2)	−0.010 (2)

Geometric parameters (Å, º) top

Zn1—O10ⁱ	1.9779 (19)	C3—C4	1.391 (4)
Zn1—O4ⁱⁱ	2.010 (2)	C3—C7	1.506 (4)
Zn1—O11	2.030 (2)	C4—C5	1.390 (4)
Zn1—O2	2.052 (2)	C4—H4	0.9500
Zn1—O12	2.073 (2)	C5—C6	1.411 (4)
Zn2—O8ⁱⁱⁱ	1.953 (2)	C5—C8	1.501 (4)
Zn2—O9ⁱ	1.966 (2)	C6—H6	0.9500
Zn2—O3ⁱⁱ	1.967 (2)	C9—H9A	0.9900
Zn2—O1	1.986 (2)	C9—H9B	0.9900
O1—C7	1.270 (3)	C10—C11	1.389 (4)
O2—C7	1.263 (3)	C10—C15	1.400 (4)
O3—C8	1.253 (4)	C11—C12	1.400 (4)
O3—Zn2^iv	1.967 (2)	C11—H11	0.9500
O4—C8	1.270 (4)	C12—C13	1.389 (4)
O4—Zn1^iv	2.010 (2)	C12—C16	1.517 (4)
O5—C1	1.390 (3)	C13—C14	1.396 (4)
O5—C9	1.424 (4)	C13—H13	0.9500
O6—C10	1.384 (3)	C14—C15	1.402 (4)
O6—C9	1.414 (4)	C14—C17	1.496 (4)
O7—C16	1.230 (4)	C15—H15	0.9500
O8—C16	1.284 (4)	C18—H18	0.9500
O8—Zn2^v	1.953 (2)	C19—H19A	0.9800
O9—C17	1.263 (3)	C19—H19B	0.9800
O9—Zn2^vi	1.966 (2)	C19—H19C	0.9800
O10—C17	1.262 (3)	C20—H20A	0.9800
O10—Zn1^vi	1.9779 (19)	C20—H20B	0.9800
O11—C18	1.252 (5)	C20—H20C	0.9800
O12—C21	1.245 (4)	C21—H21	0.9500
O13—C24	1.244 (5)	C22—H22A	0.9800
N1—C18	1.307 (5)	C22—H22B	0.9800
N1—C19	1.407 (7)	C22—H22C	0.9800
N1—C20	1.460 (6)	C23—H23A	0.9800
N2—C21	1.310 (4)	C23—H23B	0.9800
N2—C23	1.466 (5)	C23—H23C	0.9800
N2—C22	1.470 (5)	C24—H24	0.9500
N3—C24	1.348 (5)	C25—H25A	0.9800
N3—C26	1.424 (5)	C25—H25B	0.9800
N3—C25	1.468 (5)	C25—H25C	0.9800
C1—C6	1.385 (4)	C26—H26A	0.9800
C1—C2	1.394 (4)	C26—H26B	0.9800
C2—C3	1.393 (4)	C26—H26C	0.9800
C2—H2	0.9500

O10ⁱ—Zn1—O4ⁱⁱ	115.39 (9)	C11—C10—C15	120.6 (3)
O10ⁱ—Zn1—O11	96.95 (10)	C10—C11—C12	119.3 (3)
O4ⁱⁱ—Zn1—O11	147.61 (11)	C10—C11—H11	120.4
O10ⁱ—Zn1—O2	101.72 (8)	C12—C11—H11	120.4
O4ⁱⁱ—Zn1—O2	90.56 (9)	C13—C12—C11	120.8 (3)
O11—Zn1—O2	84.18 (10)	C13—C12—C16	120.5 (3)
O10ⁱ—Zn1—O12	95.31 (10)	C11—C12—C16	118.7 (3)
O4ⁱⁱ—Zn1—O12	88.20 (9)	C12—C13—C14	119.8 (3)
O11—Zn1—O12	87.10 (10)	C12—C13—H13	120.1
O2—Zn1—O12	161.68 (9)	C14—C13—H13	120.1
O8ⁱⁱⁱ—Zn2—O9ⁱ	113.43 (9)	C13—C14—C15	120.0 (3)
O8ⁱⁱⁱ—Zn2—O3ⁱⁱ	103.75 (9)	C13—C14—C17	121.4 (3)
O9ⁱ—Zn2—O3ⁱⁱ	122.06 (9)	C15—C14—C17	118.5 (3)
O8ⁱⁱⁱ—Zn2—O1	100.29 (8)	C10—C15—C14	119.5 (3)
O9ⁱ—Zn2—O1	109.06 (8)	C10—C15—H15	120.2
O3ⁱⁱ—Zn2—O1	105.88 (9)	C14—C15—H15	120.2
C7—O1—Zn2	119.91 (18)	O7—C16—O8	124.3 (3)
C7—O2—Zn1	131.99 (19)	O7—C16—C12	120.2 (3)
C8—O3—Zn2^iv	130.68 (19)	O8—C16—C12	115.5 (2)
C8—O4—Zn1^iv	127.46 (18)	O10—C17—O9	125.6 (3)
C1—O5—C9	118.7 (2)	O10—C17—C14	116.8 (3)
C10—O6—C9	119.1 (2)	O9—C17—C14	117.5 (3)
C16—O8—Zn2^v	112.12 (18)	O11—C18—N1	124.6 (4)
C17—O9—Zn2^vi	123.25 (18)	O11—C18—H18	117.7
C17—O10—Zn1^vi	134.87 (19)	N1—C18—H18	117.7
C18—O11—Zn1	129.1 (3)	N1—C19—H19A	109.5
C21—O12—Zn1	125.8 (2)	N1—C19—H19B	109.5
C18—N1—C19	118.5 (5)	H19A—C19—H19B	109.5
C18—N1—C20	122.3 (5)	N1—C19—H19C	109.5
C19—N1—C20	119.1 (4)	H19A—C19—H19C	109.5
C21—N2—C23	121.0 (3)	H19B—C19—H19C	109.5
C21—N2—C22	121.3 (3)	N1—C20—H20A	109.5
C23—N2—C22	116.5 (3)	N1—C20—H20B	109.5
C24—N3—C26	122.9 (3)	H20A—C20—H20B	109.5
C24—N3—C25	118.8 (3)	N1—C20—H20C	109.5
C26—N3—C25	118.0 (4)	H20A—C20—H20C	109.5
C6—C1—O5	125.0 (3)	H20B—C20—H20C	109.5
C6—C1—C2	121.0 (3)	O12—C21—N2	123.7 (3)
O5—C1—C2	114.1 (3)	O12—C21—H21	118.2
C3—C2—C1	119.8 (3)	N2—C21—H21	118.2
C3—C2—H2	120.1	N2—C22—H22A	109.5
C1—C2—H2	120.1	N2—C22—H22B	109.5
C4—C3—C2	120.1 (3)	H22A—C22—H22B	109.5
C4—C3—C7	119.8 (3)	N2—C22—H22C	109.5
C2—C3—C7	120.1 (3)	H22A—C22—H22C	109.5
C5—C4—C3	119.8 (3)	H22B—C22—H22C	109.5
C5—C4—H4	120.1	N2—C23—H23A	109.5
C3—C4—H4	120.1	N2—C23—H23B	109.5
C4—C5—C6	120.5 (3)	H23A—C23—H23B	109.5
C4—C5—C8	119.2 (3)	N2—C23—H23C	109.5
C6—C5—C8	120.3 (3)	H23A—C23—H23C	109.5
C1—C6—C5	118.8 (3)	H23B—C23—H23C	109.5
C1—C6—H6	120.6	O13—C24—N3	126.4 (4)
C5—C6—H6	120.6	O13—C24—H24	116.8
O2—C7—O1	125.5 (3)	N3—C24—H24	116.8
O2—C7—C3	117.0 (3)	N3—C25—H25A	109.5
O1—C7—C3	117.5 (2)	N3—C25—H25B	109.5
O3—C8—O4	125.6 (3)	H25A—C25—H25B	109.5
O3—C8—C5	116.7 (2)	N3—C25—H25C	109.5
O4—C8—C5	117.7 (3)	H25A—C25—H25C	109.5
O6—C9—O5	113.1 (2)	H25B—C25—H25C	109.5
O6—C9—H9A	109.0	N3—C26—H26A	109.5
O5—C9—H9A	109.0	N3—C26—H26B	109.5
O6—C9—H9B	109.0	H26A—C26—H26B	109.5
O5—C9—H9B	109.0	N3—C26—H26C	109.5
H9A—C9—H9B	107.8	H26A—C26—H26C	109.5
O6—C10—C11	125.2 (3)	H26B—C26—H26C	109.5
O6—C10—C15	114.1 (3)

O8ⁱⁱⁱ—Zn2—O1—C7	138.9 (2)	C6—C5—C8—O3	169.7 (3)
O9ⁱ—Zn2—O1—C7	−101.7 (2)	C4—C5—C8—O4	172.4 (3)
O3ⁱⁱ—Zn2—O1—C7	31.3 (2)	C6—C5—C8—O4	−9.2 (4)
O10ⁱ—Zn1—O2—C7	3.6 (3)	C10—O6—C9—O5	−65.0 (3)
O4ⁱⁱ—Zn1—O2—C7	−112.5 (3)	C1—O5—C9—O6	−60.1 (3)
O11—Zn1—O2—C7	99.5 (3)	C9—O6—C10—C11	11.8 (4)
O12—Zn1—O2—C7	161.5 (3)	C9—O6—C10—C15	−170.6 (2)
O10ⁱ—Zn1—O11—C18	−113.8 (4)	O6—C10—C11—C12	177.4 (3)
O4ⁱⁱ—Zn1—O11—C18	63.2 (4)	C15—C10—C11—C12	0.0 (4)
O2—Zn1—O11—C18	145.0 (4)	C10—C11—C12—C13	1.5 (4)
O12—Zn1—O11—C18	−18.8 (4)	C10—C11—C12—C16	−176.2 (2)
O10ⁱ—Zn1—O12—C21	−134.1 (3)	C11—C12—C13—C14	−1.9 (4)
O4ⁱⁱ—Zn1—O12—C21	−18.7 (3)	C16—C12—C13—C14	175.7 (3)
O11—Zn1—O12—C21	129.2 (3)	C12—C13—C14—C15	0.9 (4)
O2—Zn1—O12—C21	67.6 (5)	C12—C13—C14—C17	−177.5 (3)
C9—O5—C1—C6	−3.0 (4)	O6—C10—C15—C14	−178.6 (2)
C9—O5—C1—C2	176.2 (2)	C11—C10—C15—C14	−0.9 (4)
C6—C1—C2—C3	−0.3 (4)	C13—C14—C15—C10	0.5 (4)
O5—C1—C2—C3	−179.5 (2)	C17—C14—C15—C10	179.0 (2)
C1—C2—C3—C4	1.1 (4)	Zn2^v—O8—C16—O7	−5.5 (4)
C1—C2—C3—C7	179.5 (3)	Zn2^v—O8—C16—C12	176.76 (18)
C2—C3—C4—C5	0.2 (4)	C13—C12—C16—O7	178.9 (3)
C7—C3—C4—C5	−178.1 (3)	C11—C12—C16—O7	−3.4 (4)
C3—C4—C5—C6	−2.4 (4)	C13—C12—C16—O8	−3.3 (4)
C3—C4—C5—C8	176.0 (3)	C11—C12—C16—O8	174.4 (3)
O5—C1—C6—C5	177.3 (3)	Zn1^vi—O10—C17—O9	41.3 (4)
C2—C1—C6—C5	−1.8 (4)	Zn1^vi—O10—C17—C14	−139.2 (2)
C4—C5—C6—C1	3.2 (4)	Zn2^vi—O9—C17—O10	11.7 (4)
C8—C5—C6—C1	−175.2 (3)	Zn2^vi—O9—C17—C14	−167.89 (18)
Zn1—O2—C7—O1	41.7 (5)	C13—C14—C17—O10	172.8 (3)
Zn1—O2—C7—C3	−139.1 (2)	C15—C14—C17—O10	−5.6 (4)
Zn2—O1—C7—O2	19.6 (4)	C13—C14—C17—O9	−7.6 (4)
Zn2—O1—C7—C3	−159.64 (19)	C15—C14—C17—O9	174.0 (2)
C4—C3—C7—O2	−10.6 (4)	Zn1—O11—C18—N1	−178.6 (3)
C2—C3—C7—O2	171.0 (3)	C19—N1—C18—O11	1.8 (7)
C4—C3—C7—O1	168.7 (3)	C20—N1—C18—O11	178.2 (4)
C2—C3—C7—O1	−9.7 (4)	Zn1—O12—C21—N2	−157.8 (3)
Zn2^iv—O3—C8—O4	−4.0 (5)	C23—N2—C21—O12	5.5 (6)
Zn2^iv—O3—C8—C5	177.16 (19)	C22—N2—C21—O12	172.3 (4)
Zn1^iv—O4—C8—O3	47.0 (4)	C26—N3—C24—O13	177.5 (4)
Zn1^iv—O4—C8—C5	−134.2 (2)	C25—N3—C24—O13	2.8 (6)
C4—C5—C8—O3	−8.7 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₁₇H₈O₁₀)(C₃H₇NO)₂]·C₃H₇NO
M_r	722.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	11.2562 (6), 13.1744 (7), 20.3965 (12)
V (Å³)	3024.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.66
Crystal size (mm)	0.15 × 0.14 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker 2008)
T_min, T_max	0.789, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	15188, 5261, 5131
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.064, 1.07
No. of reflections	5261
No. of parameters	403
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.51
Absolute structure	Flack (1983), 2298 Friedel pairs
Absolute structure parameter	0.010 (9)

Computer programs: APEX2 (Bruker 2008), SAINT (Bruker 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O10ⁱ	1.9779 (19)	Zn2—O8ⁱⁱⁱ	1.953 (2)
Zn1—O4ⁱⁱ	2.010 (2)	Zn2—O9ⁱ	1.966 (2)
Zn1—O11	2.030 (2)	Zn2—O3ⁱⁱ	1.967 (2)
Zn1—O2	2.052 (2)	Zn2—O1	1.986 (2)
Zn1—O12	2.073 (2)

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

Acknowledgements

This work was supported by the National High Technology Research and Development Program 863 (No. 2009AA063201).

References

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