Poly[tris­(2,5-dimethyl­benzene-1,4-­dicarboxyl­ato)bis­(pyridine)trizinc(II)]

Wang, F.-K.; Yang, S.-Y.; Huang, R.-B.; Nie, L.

doi:10.1107/S1600536810004848

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m282

doi:10.1107/S1600536810004848

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Poly[tris(2,5-dimethylbenzene-1,4-dicarboxylato)bis(pyridine)trizinc(II)]

Fang-Kuo Wang,^a,^b ^* Shi-Yao Yang,^b Rong-Bin Huang ^b and Li Nie ^a

^aDepartment of Chemistry, West Anhui University, Lu' an 237012, People's Republic of China, and ^bDepartment of Chemistry, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: wangfangkuo2491@126.com

(Received 26 October 2009; accepted 7 February 2010; online 13 February 2010)

The asymmetric unit of the title polymeric compound, [Zn₃(C₁₀H₈O₄)₃(C₅H₅N)₂]_n or [Zn₃(dmbdc)₃(py)₂]_n (dmbdc = 2,5-dimethylbenzenedicarboxylate; py = pyridine) contains two Zn(II) ions, one of which is located on an inversion centre, one and a half 2,5-dimethylbenzenedicarboxylate ligands and one pyridine ligand. Each ZnO₆ octahedron is sandwiched between two ZnO₄N square-pyramids, forming a trinuclear zinc secondary building unit (SBU); each SBU is further linked by six 2,5-dimethylbenzenedicarboxylate ligands with six adjacent trinuclear zinc SBU's, forming a two-dimensional layer structure with a (3,6) net. One of the three zinc ions is octahedrally coordinated and the other two are square-pyramidally coordinated. The coordination modes for 2,5-dimethylbenzenedicarboxylates are bis(bidentate) or bidentate-tridentate.

Related literature

For the potential applications of metal-organic frameworks formed from terephthalic acid and its derivatives, see Wang et al. (2007 ); Grzesiak et al. (2006 ); Rosi et al. (2005 ); Burrows et al. (2005 ); Liao et al. (2006 ); Yang et al. (2002 ); Eddaoudi et al. (2002 ). For related structures, see: Wang et al. (2008 ); Zhou et al. (2009 ).

Experimental

Crystal data

[Zn₃(C₁₀H₈O₄)₃(C₅H₅N)₂]
M_r = 930.80
Monoclinic, C 2/c
a = 22.3372 (15) Å
b = 10.2643 (7) Å
c = 16.9261 (11) Å
β = 105.140 (1)°
V = 3746.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 299 K
0.12 × 0.08 × 0.07 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.798, T_max = 0.874
16107 measured reflections
4487 independent reflections
3559 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.156
S = 1.08
4487 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810004848/bv2132sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004848/bv2132Isup2.hkl

checkCIF report

Comment top

Terephthalic acid and its derivatives have been used to construct metal-organic frameworks. Some of these compounds display interesting structures and have potential applications (Wang et al., 2007; Grzesiak et al., 2006; Rosi et al., 2005; Burrows et al., 2005; Liao et al., 2006; Yang et al., 2002; Eddaoudi et al.,2002; Zhou et al., 2009). In this paper we report a coordination polymer [Zn₃(dmbdc)₃(py)₂]_n, 1 (dmbdc=2,5-dimethylbenzenedicarboxylate; py=pyridine) synthesized by hydrothermal reaction.

The structure of 1 contains trinuclear zinc SBU's (SBU = Secondary Building Unit) (Fig. 1), in which each ZnO₆ octahedron sandwiched between two ZnO₄N square-pyramids. The three Zn ions exhibit two different coordination geometries: Zn1 coordinates to four oxygen atoms from three carboxylates in the plane and a nitrogen atom from py (py = pyridine) at the apex giving a distorted square-pyramidal geometry; Zn2 atom is coordinated by six oxygen atoms from six dmbdc anions (dmbdc=2,5-dimethylbenzenedicarboxylate) to constitute a slightly distorted octahedral environment. Coordination polymers with similar but different trinuclear zinc SBU's have been reported in recent years (Wang et al., 2008). There are two coordination modes for the dmbdc in the structure of 1, one is bis(bidentate), and the other one adopts bidentate and tridentate for each of its carboxyl groups. However, each trinuclear zinc SBU is further linked by six dmbdc ligands to six adjacent trinuclear zinc SBU's to form a two-dimensional sheet with a (3,6) net parallel to bc plane (Fig. 2). The two-dimensional sheets are further packed in an ABAB··· mode along b axis (Fig. 3). Coordinated pyridine molecules lie in the both sides of trinuclear zinc SBU's respectively.

Related literature top

For the potential applications of metal-organic frameworks formed from terephthalic acid and its derivatives, see Wang et al. (2007); Grzesiak et al. (2006); Rosi et al. (2005); Burrows et al. (2005); Liao et al. (2006); Yang et al. (2002); Eddaoudi et al. (2002). For related structures, see: Wang et al. (2008); Zhou et al. (2009).

Experimental top

A suspension of 2,5-dimethylbenzenedicarboxylic acid (H₂dmbdc, 0.097 g, 0.50 mmol) in H₂O (12 ml), pyridine was slowly added to the solution until pH was adjusted to 7, then Zn(NO₃)₂^.6H₂O (0.15 g, 0.50 mmol) was added. The mixture was placed in a 20 ml Teflon-lined vessel, heated to 120°C at the rate of 0.2°C/min, and kept at 120°C for 3 days, then slowly cooled down to room temperature at the rate of 0.1°C/min. Colorless platelet crystals (0.062 g, yield 40%) were separated by filtration, washed with deionized water and dried in air. Elemental Analysis: C₄₀H₃₄N₂O₁₂Zn₃, found (calc.) C 51.52 (51.61), H 3.66 (3.69), N 2.99 (3.01). FTIR (KBr, cm^-1): 3454 (m), 3031 (w), 2961 (m), 2739 (w), 1922 (w), 1820 (m),1452 (m), 1399 (s), 1347 (m), 1158 (m), 1074 (s), 918 (s), 797 (versus).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The connection of the trinuclear zinc SBU's. (Hydrogen atoms are omitted for clarity.)
	Fig. 2. A perspective view of the two-dimensional (3, 6) net of 1 on bc plane. (Hydrogen atoms are omitted for clarity.)
	Fig. 3. View of two-dimensional (3, 6) net of 1 stacked by ABAB mode along b axis. (Hydrogen atoms are omitted for clarity.)

Poly[tris(2,5-dimethylbenzene-1,4-dicarboxylato)bis(pyridine)trizinc(II)] top

Crystal data top

[Zn₃(C₁₀H₈O₄)₃(C₅H₅N)₂]	F(000) = 1896
M_r = 930.80	D_x = 1.650 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2781 reflections
a = 22.3372 (15) Å	θ = 2.2–25.0°
b = 10.2643 (7) Å	µ = 1.97 mm⁻¹
c = 16.9261 (11) Å	T = 299 K
β = 105.140 (1)°	Block, colorless
V = 3746.0 (4) Å³	0.12 × 0.08 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEX area-detector diffractometer	4487 independent reflections
Radiation source: fine-focus sealed tube	3559 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scan	θ_max = 28.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −28→30
T_min = 0.798, T_max = 0.874	k = −13→13
16107 measured reflections	l = −21→22

Refinement top

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0282P)² + 12.5564P] where P = (F_o² + 2F_c²)/3
4487 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Zn₃(C₁₀H₈O₄)₃(C₅H₅N)₂]	V = 3746.0 (4) Å³
M_r = 930.80	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.3372 (15) Å	µ = 1.97 mm⁻¹
b = 10.2643 (7) Å	T = 299 K
c = 16.9261 (11) Å	0.12 × 0.08 × 0.07 mm
β = 105.140 (1)°

Data collection top

Bruker SMART APEX area-detector diffractometer	4487 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3559 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.874	R_int = 0.059
16107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0282P)² + 12.5564P] where P = (F_o² + 2F_c²)/3
4487 reflections	Δρ_max = 0.74 e Å⁻³
262 parameters	Δρ_min = −0.63 e Å⁻³

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	0.40381 (2)	0.67147 (5)	0.55736 (3)	0.02859 (17)
Zn2	0.2500	0.7500	0.5000	0.02465 (19)
O1	0.40247 (16)	0.7797 (3)	0.4622 (2)	0.0379 (8)
O2	0.31369 (15)	0.8673 (3)	0.4686 (2)	0.0347 (7)
O3	0.29594 (17)	1.2435 (4)	0.12228 (19)	0.0425 (9)
O4	0.39737 (16)	1.2197 (4)	0.1478 (2)	0.0426 (9)
O5	0.37531 (18)	0.4905 (4)	0.5713 (3)	0.0557 (11)
O6	0.30025 (18)	0.5819 (3)	0.4821 (2)	0.0444 (9)
N1	0.49686 (18)	0.6283 (4)	0.5907 (3)	0.0397 (10)
C1	0.3588 (2)	0.9476 (5)	0.3687 (3)	0.0309 (10)
C2	0.4095 (2)	0.9664 (5)	0.3361 (3)	0.0368 (11)
C3	0.4018 (2)	1.0506 (5)	0.2701 (3)	0.0362 (11)
H3A	0.4354	1.0645	0.2483	0.043*
C4	0.3476 (2)	1.1143 (4)	0.2354 (3)	0.0297 (9)
C5	0.2970 (2)	1.0983 (5)	0.2683 (3)	0.0310 (9)
C6	0.3049 (2)	1.0147 (5)	0.3343 (3)	0.0325 (10)
H6A	0.2716	1.0031	0.3570	0.039*
C7	0.3581 (2)	0.8590 (4)	0.4383 (3)	0.0297 (9)
C8	0.4722 (3)	0.9037 (8)	0.3691 (5)	0.074 (2)
H8A	0.5009	0.9382	0.3409	0.111*
H8B	0.4686	0.8112	0.3608	0.111*
H8C	0.4871	0.9218	0.4265	0.111*
C9	0.3457 (2)	1.1994 (4)	0.1631 (3)	0.0308 (10)
C10	0.2367 (3)	1.1692 (6)	0.2392 (4)	0.0521 (15)
H10A	0.2090	1.1424	0.2709	0.078*
H10B	0.2187	1.1493	0.1825	0.078*
H10C	0.2439	1.2613	0.2454	0.078*
C11	0.3226 (2)	0.4861 (5)	0.5232 (3)	0.0400 (12)
C12	0.2872 (2)	0.3605 (4)	0.5142 (3)	0.0322 (10)
C13	0.2293 (2)	0.3618 (4)	0.4598 (3)	0.0363 (11)
H13A	0.2154	0.4392	0.4327	0.044*
C14	0.3094 (2)	0.2458 (5)	0.5566 (3)	0.0381 (11)
C15	0.3713 (3)	0.2313 (6)	0.6163 (4)	0.0630 (18)
H15A	0.3768	0.1427	0.6351	0.095*
H15B	0.3738	0.2881	0.6621	0.095*
H15C	0.4033	0.2537	0.5903	0.095*
C16	0.5188 (3)	0.5242 (8)	0.6329 (6)	0.103 (4)
H16A	0.4911	0.4643	0.6447	0.124*
C17	0.5805 (4)	0.5003 (10)	0.6601 (8)	0.134 (5)
H17A	0.5944	0.4256	0.6906	0.161*
C18	0.6214 (3)	0.5840 (8)	0.6433 (6)	0.081 (2)
H18A	0.6638	0.5700	0.6634	0.098*
C19	0.6002 (3)	0.6877 (7)	0.5972 (4)	0.0612 (17)
H19A	0.6274	0.7453	0.5821	0.073*
C20	0.5379 (3)	0.7074 (6)	0.5725 (4)	0.0536 (15)
H20A	0.5234	0.7808	0.5411	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0302 (3)	0.0257 (3)	0.0305 (3)	−0.0001 (2)	0.0090 (2)	0.0002 (2)
Zn2	0.0236 (4)	0.0256 (4)	0.0249 (3)	−0.0023 (3)	0.0067 (3)	−0.0003 (3)
O1	0.0374 (18)	0.0410 (19)	0.0380 (18)	0.0055 (15)	0.0149 (15)	0.0153 (15)
O2	0.0362 (18)	0.0304 (17)	0.0437 (19)	−0.0038 (14)	0.0213 (15)	0.0055 (14)
O3	0.042 (2)	0.060 (2)	0.0234 (15)	0.0153 (17)	0.0050 (15)	0.0087 (16)
O4	0.0374 (19)	0.053 (2)	0.0365 (18)	−0.0024 (16)	0.0089 (15)	0.0189 (16)
O5	0.042 (2)	0.035 (2)	0.087 (3)	−0.0140 (17)	0.011 (2)	−0.007 (2)
O6	0.065 (2)	0.0217 (16)	0.058 (2)	−0.0018 (16)	0.038 (2)	−0.0008 (16)
N1	0.028 (2)	0.037 (2)	0.052 (3)	0.0043 (17)	0.0073 (18)	0.002 (2)
C1	0.029 (2)	0.036 (2)	0.030 (2)	−0.0017 (18)	0.0097 (18)	0.0038 (19)
C2	0.031 (2)	0.040 (3)	0.044 (3)	0.004 (2)	0.018 (2)	0.009 (2)
C3	0.032 (2)	0.045 (3)	0.036 (2)	0.002 (2)	0.016 (2)	0.009 (2)
C4	0.030 (2)	0.031 (2)	0.026 (2)	−0.0008 (18)	0.0042 (18)	0.0016 (18)
C5	0.027 (2)	0.033 (2)	0.031 (2)	−0.0005 (18)	0.0057 (18)	0.0025 (19)
C6	0.029 (2)	0.035 (2)	0.037 (2)	0.0010 (19)	0.0134 (19)	0.004 (2)
C7	0.031 (2)	0.026 (2)	0.033 (2)	−0.0048 (18)	0.0113 (19)	0.0013 (18)
C8	0.041 (3)	0.100 (5)	0.092 (5)	0.031 (4)	0.037 (3)	0.060 (5)
C9	0.036 (3)	0.028 (2)	0.027 (2)	−0.0017 (19)	0.0062 (19)	−0.0019 (18)
C10	0.036 (3)	0.070 (4)	0.051 (3)	0.013 (3)	0.014 (2)	0.020 (3)
C11	0.045 (3)	0.027 (2)	0.055 (3)	−0.005 (2)	0.027 (3)	−0.011 (2)
C12	0.032 (2)	0.021 (2)	0.049 (3)	−0.0012 (17)	0.019 (2)	−0.0027 (19)
C13	0.034 (2)	0.023 (2)	0.053 (3)	0.0055 (18)	0.012 (2)	0.007 (2)
C14	0.033 (2)	0.031 (2)	0.050 (3)	0.0039 (19)	0.009 (2)	0.002 (2)
C15	0.042 (3)	0.049 (4)	0.084 (5)	0.002 (3)	−0.008 (3)	0.014 (3)
C16	0.047 (4)	0.083 (6)	0.166 (9)	0.003 (4)	0.006 (5)	0.071 (6)
C17	0.045 (4)	0.109 (7)	0.231 (13)	0.015 (5)	0.006 (6)	0.098 (9)
C18	0.037 (3)	0.081 (5)	0.121 (7)	0.012 (4)	0.010 (4)	−0.002 (5)
C19	0.038 (3)	0.078 (5)	0.069 (4)	−0.011 (3)	0.015 (3)	−0.014 (4)
C20	0.043 (3)	0.059 (4)	0.059 (4)	−0.006 (3)	0.014 (3)	0.007 (3)

Geometric parameters (Å, º) top

Zn1—O4ⁱ	1.931 (3)	C4—C9	1.496 (6)
Zn1—O1	1.950 (3)	C5—C6	1.384 (6)
Zn1—O5	1.998 (4)	C5—C10	1.495 (7)
Zn1—N1	2.055 (4)	C6—H6A	0.9300
Zn1—C11	2.588 (5)	C8—H8A	0.9600
Zn2—O2	2.037 (3)	C8—H8B	0.9600
Zn2—O2ⁱⁱ	2.037 (3)	C8—H8C	0.9600
Zn2—O3ⁱⁱⁱ	2.057 (3)	C10—H10A	0.9600
Zn2—O3ⁱ	2.057 (3)	C10—H10B	0.9600
Zn2—O6	2.123 (3)	C10—H10C	0.9600
Zn2—O6ⁱⁱ	2.123 (3)	C11—C12	1.500 (6)
O1—C7	1.265 (6)	C12—C13	1.378 (7)
O2—C7	1.233 (5)	C12—C14	1.401 (7)
O3—C9	1.231 (6)	C13—C14^vi	1.385 (7)
O3—Zn2^iv	2.057 (3)	C13—H13A	0.9300
O4—C9	1.264 (6)	C14—C13^vi	1.385 (7)
O4—Zn1^v	1.931 (3)	C14—C15	1.492 (7)
O5—C11	1.245 (6)	C15—H15A	0.9600
O6—C11	1.233 (6)	C15—H15B	0.9600
N1—C16	1.308 (8)	C15—H15C	0.9600
N1—C20	1.320 (7)	C16—C17	1.356 (10)
C1—C6	1.378 (6)	C16—H16A	0.9300
C1—C2	1.395 (6)	C17—C18	1.337 (11)
C1—C7	1.492 (6)	C17—H17A	0.9300
C2—C3	1.387 (7)	C18—C19	1.332 (10)
C2—C8	1.511 (7)	C18—H18A	0.9300
C3—C4	1.367 (6)	C19—C20	1.359 (8)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.393 (6)	C20—H20A	0.9300

O4ⁱ—Zn1—O1	109.70 (17)	O2—C7—C1	117.6 (4)
O4ⁱ—Zn1—O5	110.64 (18)	O1—C7—C1	118.4 (4)
O1—Zn1—O5	133.67 (17)	C2—C8—H8A	109.5
O4ⁱ—Zn1—N1	100.73 (17)	C2—C8—H8B	109.5
O1—Zn1—N1	98.40 (16)	H8A—C8—H8B	109.5
O5—Zn1—N1	95.60 (17)	C2—C8—H8C	109.5
O4ⁱ—Zn1—C11	114.20 (16)	H8A—C8—H8C	109.5
O1—Zn1—C11	112.05 (17)	H8B—C8—H8C	109.5
O5—Zn1—C11	27.91 (16)	O3—C9—O4	124.3 (4)
N1—Zn1—C11	120.16 (17)	O3—C9—C4	120.2 (4)
O2—Zn2—O2ⁱⁱ	180.00 (18)	O4—C9—C4	115.5 (4)
O2—Zn2—O3ⁱⁱⁱ	87.46 (14)	C5—C10—H10A	109.5
O2ⁱⁱ—Zn2—O3ⁱⁱⁱ	92.54 (14)	C5—C10—H10B	109.5
O2—Zn2—O3ⁱ	92.54 (14)	H10A—C10—H10B	109.5
O2ⁱⁱ—Zn2—O3ⁱ	87.46 (14)	C5—C10—H10C	109.5
O3ⁱⁱⁱ—Zn2—O3ⁱ	180.000 (1)	H10A—C10—H10C	109.5
O2—Zn2—O6	90.67 (13)	H10B—C10—H10C	109.5
O2ⁱⁱ—Zn2—O6	89.33 (13)	O6—C11—O5	121.0 (5)
O3ⁱⁱⁱ—Zn2—O6	88.47 (15)	O6—C11—C12	120.2 (5)
O3ⁱ—Zn2—O6	91.53 (15)	O5—C11—C12	118.8 (5)
O2—Zn2—O6ⁱⁱ	89.33 (13)	O6—C11—Zn1	72.3 (3)
O2ⁱⁱ—Zn2—O6ⁱⁱ	90.67 (13)	O5—C11—Zn1	48.7 (2)
O3ⁱⁱⁱ—Zn2—O6ⁱⁱ	91.53 (15)	C12—C11—Zn1	167.2 (4)
O3ⁱ—Zn2—O6ⁱⁱ	88.47 (15)	C13—C12—C14	119.8 (4)
O6—Zn2—O6ⁱⁱ	180.0 (2)	C13—C12—C11	116.0 (4)
C7—O1—Zn1	118.2 (3)	C14—C12—C11	124.3 (5)
C7—O2—Zn2	139.4 (3)	C12—C13—C14^vi	123.7 (4)
C9—O3—Zn2^iv	135.7 (3)	C12—C13—H13A	118.2
C9—O4—Zn1^v	121.2 (3)	C14^vi—C13—H13A	118.2
C11—O5—Zn1	103.4 (3)	C13^vi—C14—C12	116.6 (5)
C11—O6—Zn2	136.0 (3)	C13^vi—C14—C15	118.4 (5)
C16—N1—C20	116.5 (5)	C12—C14—C15	125.0 (5)
C16—N1—Zn1	122.3 (4)	C14—C15—H15A	109.5
C20—N1—Zn1	121.2 (4)	C14—C15—H15B	109.5
C6—C1—C2	118.3 (4)	H15A—C15—H15B	109.5
C6—C1—C7	116.7 (4)	C14—C15—H15C	109.5
C2—C1—C7	125.1 (4)	H15A—C15—H15C	109.5
C3—C2—C1	117.6 (4)	H15B—C15—H15C	109.5
C3—C2—C8	118.1 (4)	N1—C16—C17	122.5 (7)
C1—C2—C8	124.4 (4)	N1—C16—H16A	118.8
C4—C3—C2	123.6 (4)	C17—C16—H16A	118.8
C4—C3—H3A	118.2	C18—C17—C16	120.0 (8)
C2—C3—H3A	118.2	C18—C17—H17A	120.0
C3—C4—C5	119.5 (4)	C16—C17—H17A	120.0
C3—C4—C9	117.6 (4)	C19—C18—C17	118.8 (7)
C5—C4—C9	122.9 (4)	C19—C18—H18A	120.6
C6—C5—C4	116.7 (4)	C17—C18—H18A	120.6
C6—C5—C10	118.8 (4)	C18—C19—C20	118.5 (7)
C4—C5—C10	124.5 (4)	C18—C19—H19A	120.7
C1—C6—C5	124.3 (4)	C20—C19—H19A	120.7
C1—C6—H6A	117.8	N1—C20—C19	123.7 (6)
C5—C6—H6A	117.8	N1—C20—H20A	118.2
O2—C7—O1	124.0 (4)	C19—C20—H20A	118.2

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

Experimental details

Crystal data
Chemical formula	[Zn₃(C₁₀H₈O₄)₃(C₅H₅N)₂]
M_r	930.80
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	22.3372 (15), 10.2643 (7), 16.9261 (11)
β (°)	105.140 (1)
V (Å³)	3746.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.12 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.798, 0.874
No. of measured, independent and observed [I > 2σ(I)] reflections	16107, 4487, 3559
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.677

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.156, 1.08
No. of reflections	4487
No. of parameters	262
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0282P)² + 12.5564P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.63

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Acknowledgements

We are grateful for financial support by the National Natural Science Foundation of China (grant No. 20471049) and Xiamen University.

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