Poly[(μ2-4,4′-bipyridine-κ2N:N′)bis­(μ4-cyclo­hexane-1,3-dicarboxyl­ato-κ4O:O′:O′′:O′′′)dizinc(II)]

Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536809035168

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1179

doi:10.1107/S1600536809035168

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Poly[(μ₂-4,4′-bipyridine-κ²N:N′)bis(μ₄-cyclohexane-1,3-dicarboxylato-κ⁴O:O′:O′′:O′′′)dizinc(II)]

Mohd. Razali Rizal ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 August 2009; accepted 1 September 2009; online 9 September 2009)

The cyclohexane-1,3-dicarboxylate dianion in the title three-dimensional coordination polymer, [Zn₂(C₈H₁₀O₄)₂(C₁₀H₈N₂)]_n, has one carboxylate group in an equatorial position and the other in an axial position of the cyclohexane ring, which adopts a chair conformation. The carboxylate groups function as bridges to two adjacent Zn^II atoms, generating a layer motif. Adjacent layers are linked through the 4,4′-bipyridine N-heterocycle, forming a three-dimensional network; the geometry of Zn^II is square-pyramidal with the N atom of the N-heterocycle occupying the apical position. The N-heterocycle lies about a center of inversion and is disordered in a 1:1 ratio with respect to the C atoms bearing H atoms.

Related literature

For the zinc cyclohexane-1,3-dicarboxylate adduct of 1,10-phenanthroline, see: Bailey et al. (2008 ).

Experimental

Crystal data

[Zn₂(C₈H₁₀O₄)₂(C₁₀H₈N₂)]
M_r = 313.64
Monoclinic, C 2/c
a = 22.251 (2) Å
b = 13.436 (1) Å
c = 8.552 (1) Å
β = 104.446 (5)°
V = 2475.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.99 mm⁻¹
T = 100 K
0.12 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.557, T_max = 1.000
8536 measured reflections
2175 independent reflections
1407 reflections with I > 2σ(I)
R_int = 0.116

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.123
S = 0.99
2175 reflections
184 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSHELL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035168/tk2535sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035168/tk2535Isup2.hkl

checkCIF report

Related literature top

For the zinc cyclohexane-1,3-dicarboxylate adduct of 1,10-phenanthroline, see: Bailey et al. (2008).

Experimental top

Zinc acetate (0.15 g, 0.76 mmol), cyclohexane-1,3-dicarboxylic acid (mixture of cis- and trans-isomers) (0.13 g, 0.76 mmol) and 4,4'-bipyridine (0.12 g, 0.76 mmol) along with water (18 ml) were heated in a 23-ml Teflon-lined stainless-steel Parr bomb. The bomb was heated at 403 K for 3 days. The bomb was cooled to room temperature at 5 K per hour. Tiny crystals were isolated from the solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSHELL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. 50% Probability displacement ellipsoid plot of the asymmetric unit of Zn₂(C₁₀H₈N₂)(C₈H₁₀O₄)₂ extended to show the coordination environment of the zinc center and a full molecule of 4,4'-bipyridine. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry operations i: 0.5-x, 1.5-y, 1-z; ii: 0.5-x, 0.5+y, 0.5-z; iii: x, 1-y, 0.5+z.

Poly[(µ₂-4,4'-bipyridine-κ²N:N')bis(µ₄-cyclohexane- 1,3-dicarboxylato-κ⁴O:O':O'':O''')dizinc(II)] top

Crystal data top

[Zn₂(C₈H₁₀O₄)₂(C₁₀H₈N₂)]	F(000) = 1288
M_r = 313.64	D_x = 1.683 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 543 reflections
a = 22.251 (2) Å	θ = 2.8–21.0°
b = 13.436 (1) Å	µ = 1.99 mm⁻¹
c = 8.552 (1) Å	T = 100 K
β = 104.446 (5)°	Prism, colorless
V = 2475.8 (3) Å³	0.12 × 0.02 × 0.02 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	2175 independent reflections
Radiation source: fine-focus sealed tube	1407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→25
T_min = 0.557, T_max = 1.000	k = −15→15
8536 measured reflections	l = −10→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0478P)²] where P = (F_o² + 2F_c²)/3
2175 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.77 e Å⁻³
36 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Zn₂(C₈H₁₀O₄)₂(C₁₀H₈N₂)]	V = 2475.8 (3) Å³
M_r = 313.64	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.251 (2) Å	µ = 1.99 mm⁻¹
b = 13.436 (1) Å	T = 100 K
c = 8.552 (1) Å	0.12 × 0.02 × 0.02 mm
β = 104.446 (5)°

Data collection top

Bruker SMART APEX diffractometer	2175 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1407 reflections with I > 2σ(I)
T_min = 0.557, T_max = 1.000	R_int = 0.116
8536 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	36 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	Δρ_max = 0.77 e Å⁻³
2175 reflections	Δρ_min = −0.65 e Å⁻³
184 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.30423 (3)	0.80190 (5)	0.58500 (8)	0.0148 (2)
O1	0.33841 (19)	0.7868 (3)	0.3855 (5)	0.0226 (10)
O2	0.25270 (18)	0.7072 (3)	0.2612 (4)	0.0220 (10)
O3	0.24532 (18)	0.4228 (3)	0.0174 (4)	0.0192 (9)
O4	0.33149 (18)	0.3418 (3)	0.1412 (5)	0.0196 (10)
N1	0.3745 (2)	0.8727 (3)	0.7432 (5)	0.0157 (11)
C1	0.3081 (3)	0.7349 (4)	0.2723 (7)	0.0182 (14)
C2	0.3373 (3)	0.7034 (4)	0.1370 (7)	0.0190 (13)
H2	0.3281	0.7563	0.0521	0.023*
C3	0.4082 (3)	0.6950 (4)	0.1978 (7)	0.0207 (13)
H3A	0.4265	0.6834	0.1052	0.025*
H3B	0.4252	0.7581	0.2503	0.025*
C4	0.4259 (3)	0.6096 (4)	0.3182 (7)	0.0218 (14)
H4A	0.4716	0.6040	0.3530	0.026*
H4B	0.4104	0.6239	0.4148	0.026*
C5	0.3985 (3)	0.5113 (4)	0.2433 (7)	0.0232 (15)
H5A	0.4182	0.4929	0.1556	0.028*
H5B	0.4080	0.4584	0.3263	0.028*
C6	0.3287 (3)	0.5179 (4)	0.1755 (7)	0.0183 (14)
H6	0.3108	0.5325	0.2693	0.022*
C7	0.3106 (3)	0.6056 (4)	0.0586 (7)	0.0194 (14)
H7A	0.3261	0.5935	−0.0386	0.023*
H7B	0.2648	0.6107	0.0240	0.023*
C8	0.3000 (3)	0.4193 (4)	0.1038 (7)	0.0180 (14)
C9	0.4299 (6)	0.8277 (15)	0.8020 (17)	0.015 (3)	0.50
H9	0.4346	0.7607	0.7715	0.019*	0.50
C10	0.4800 (11)	0.8744 (6)	0.9043 (19)	0.022 (3)	0.50
H10	0.5181	0.8400	0.9432	0.027*	0.50
C9'	0.4219 (6)	0.8212 (16)	0.8385 (15)	0.015 (3)	0.50
H9'	0.4213	0.7506	0.8346	0.019*	0.50
C10'	0.4713 (10)	0.8691 (6)	0.942 (2)	0.022 (3)	0.50
H10'	0.5040	0.8311	1.0076	0.027*	0.50
C11	0.4734 (2)	0.9726 (4)	0.9490 (6)	0.0155 (13)
C12	0.4164 (6)	1.0188 (15)	0.8894 (17)	0.016 (3)	0.50
H12	0.4102	1.0856	0.9184	0.019*	0.50
C13	0.3687 (11)	0.9669 (6)	0.7878 (19)	0.014 (2)	0.50
H13	0.3301	0.9996	0.7477	0.017*	0.50
C12'	0.4238 (6)	1.0236 (16)	0.8504 (16)	0.016 (3)	0.50
H12'	0.4230	1.0943	0.8524	0.019*	0.50
C13'	0.3758 (10)	0.9721 (6)	0.750 (2)	0.014 (2)	0.50
H13'	0.3425	1.0085	0.6828	0.017*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0119 (4)	0.0150 (4)	0.0150 (3)	−0.0020 (3)	−0.0011 (2)	−0.0008 (3)
O1	0.027 (2)	0.021 (2)	0.021 (2)	−0.0065 (19)	0.0087 (19)	−0.0056 (18)
O2	0.019 (2)	0.030 (3)	0.017 (2)	−0.002 (2)	0.0051 (18)	−0.0029 (18)
O3	0.011 (2)	0.018 (2)	0.023 (2)	0.0018 (18)	−0.0065 (19)	0.0021 (18)
O4	0.021 (3)	0.013 (2)	0.021 (2)	0.0026 (18)	−0.0026 (19)	−0.0014 (17)
N1	0.016 (3)	0.018 (3)	0.013 (2)	0.001 (2)	0.003 (2)	−0.003 (2)
C1	0.024 (4)	0.008 (3)	0.022 (3)	0.000 (2)	0.005 (3)	0.002 (2)
C2	0.023 (3)	0.017 (3)	0.016 (3)	0.000 (3)	0.004 (3)	−0.002 (3)
C3	0.017 (3)	0.020 (3)	0.025 (3)	−0.004 (3)	0.006 (3)	−0.005 (3)
C4	0.017 (4)	0.027 (4)	0.020 (3)	0.003 (3)	0.004 (3)	−0.005 (3)
C5	0.020 (4)	0.021 (3)	0.027 (4)	0.000 (3)	0.003 (3)	0.000 (3)
C6	0.015 (4)	0.017 (3)	0.021 (3)	−0.002 (3)	0.000 (3)	0.002 (3)
C7	0.024 (4)	0.019 (3)	0.014 (3)	−0.001 (3)	0.003 (3)	−0.003 (2)
C8	0.026 (4)	0.015 (3)	0.013 (3)	−0.001 (3)	0.005 (3)	0.001 (3)
C9	0.025 (5)	0.013 (4)	0.011 (6)	−0.001 (4)	0.008 (4)	0.005 (4)
C10	0.018 (6)	0.022 (4)	0.022 (7)	0.000 (3)	−0.004 (4)	0.007 (3)
C9'	0.025 (5)	0.013 (4)	0.011 (6)	−0.001 (4)	0.008 (4)	0.005 (4)
C10'	0.018 (6)	0.022 (4)	0.022 (7)	0.000 (3)	−0.004 (4)	0.007 (3)
C11	0.010 (3)	0.021 (3)	0.013 (3)	−0.002 (3)	−0.001 (3)	−0.001 (2)
C12	0.015 (4)	0.017 (3)	0.017 (6)	−0.002 (3)	0.009 (4)	−0.006 (4)
C13	0.008 (5)	0.018 (3)	0.015 (7)	0.001 (3)	0.000 (4)	−0.002 (3)
C12'	0.015 (4)	0.017 (3)	0.017 (6)	−0.002 (3)	0.009 (4)	−0.006 (4)
C13'	0.008 (5)	0.018 (3)	0.015 (7)	0.001 (3)	0.000 (4)	−0.002 (3)

Geometric parameters (Å, º) top

Zn1—O1	2.044 (4)	C4—H4B	0.9900
Zn1—O2ⁱ	2.045 (4)	C5—C6	1.519 (8)
Zn1—O3ⁱⁱ	2.034 (4)	C5—H5A	0.9900
Zn1—O4ⁱⁱⁱ	2.044 (4)	C5—H5B	0.9900
Zn1—N1	2.031 (5)	C6—C8	1.532 (8)
Zn1—Zn1ⁱ	2.8517 (13)	C6—C7	1.533 (7)
O1—C1	1.246 (7)	C6—H6	1.0000
O2—C1	1.267 (7)	C7—H7A	0.9900
O2—Zn1ⁱ	2.045 (4)	C7—H7B	0.9900
O3—C8	1.257 (7)	C9—C10	1.384 (10)
O3—Zn1^iv	2.034 (4)	C9—H9	0.9500
O4—C8	1.252 (7)	C10—C11	1.392 (10)
O4—Zn1^v	2.044 (4)	C10—H10	0.9500
N1—C13'	1.338 (9)	C9'—C10'	1.385 (10)
N1—C13	1.338 (9)	C9'—H9'	0.9500
N1—C9'	1.351 (9)	C10'—C11	1.393 (10)
N1—C9	1.351 (9)	C10'—H10'	0.9500
C1—C2	1.522 (8)	C11—C12'	1.390 (10)
C2—C7	1.526 (7)	C11—C12	1.391 (10)
C2—C3	1.537 (8)	C11—C11^vi	1.478 (11)
C2—H2	1.0000	C12—C13	1.380 (10)
C3—C4	1.526 (8)	C12—H12	0.9500
C3—H3A	0.9900	C13—H13	0.9500
C3—H3B	0.9900	C12'—C13'	1.380 (10)
C4—C5	1.526 (8)	C12'—H12'	0.9500
C4—H4A	0.9900	C13'—H13'	0.9500

N1—Zn1—O3ⁱⁱ	99.06 (17)	C6—C5—H5B	109.2
N1—Zn1—O2ⁱ	95.55 (16)	C4—C5—H5B	109.2
O3ⁱⁱ—Zn1—O2ⁱ	88.19 (16)	H5A—C5—H5B	107.9
N1—Zn1—O1	102.59 (16)	C5—C6—C8	112.8 (5)
O3ⁱⁱ—Zn1—O1	89.70 (15)	C5—C6—C7	111.8 (5)
O2ⁱ—Zn1—O1	161.85 (15)	C8—C6—C7	112.9 (5)
N1—Zn1—O4ⁱⁱⁱ	98.71 (17)	C5—C6—H6	106.3
O3ⁱⁱ—Zn1—O4ⁱⁱⁱ	162.21 (15)	C8—C6—H6	106.3
O2ⁱ—Zn1—O4ⁱⁱⁱ	89.29 (16)	C7—C6—H6	106.3
O1—Zn1—O4ⁱⁱⁱ	87.23 (15)	C2—C7—C6	111.4 (5)
N1—Zn1—Zn1ⁱ	169.00 (12)	C2—C7—H7A	109.3
O3ⁱⁱ—Zn1—Zn1ⁱ	82.66 (11)	C6—C7—H7A	109.3
O2ⁱ—Zn1—Zn1ⁱ	73.59 (11)	C2—C7—H7B	109.3
O1—Zn1—Zn1ⁱ	88.25 (12)	C6—C7—H7B	109.3
O4ⁱⁱⁱ—Zn1—Zn1ⁱ	79.73 (11)	H7A—C7—H7B	108.0
C1—O1—Zn1	117.5 (4)	O4—C8—O3	125.4 (5)
C1—O2—Zn1ⁱ	135.7 (4)	O4—C8—C6	117.8 (5)
C8—O3—Zn1^iv	124.3 (4)	O3—C8—C6	116.7 (5)
C8—O4—Zn1^v	127.7 (4)	N1—C9—C10	123 (2)
C13'—N1—C9'	118.7 (15)	N1—C9—H9	118.4
C13—N1—C9'	115.4 (14)	C10—C9—H9	118.4
C13'—N1—C9	115.0 (15)	C9—C10—C11	119 (2)
C13—N1—C9	117.4 (15)	C9—C10—H10	120.6
C13'—N1—Zn1	120.0 (11)	C11—C10—H10	120.6
C13—N1—Zn1	121.4 (11)	N1—C9'—C10'	122 (2)
C9'—N1—Zn1	121.2 (11)	N1—C9'—H9'	119.2
C9—N1—Zn1	121.2 (11)	C10'—C9'—H9'	119.2
O1—C1—O2	123.4 (5)	C9'—C10'—C11	120 (2)
O1—C1—C2	119.6 (5)	C9'—C10'—H10'	119.8
O2—C1—C2	116.9 (5)	C11—C10'—H10'	119.8
C7—C2—C1	112.3 (5)	C12'—C11—C10	115.0 (14)
C7—C2—C3	109.8 (5)	C12—C11—C10	118.1 (14)
C1—C2—C3	111.1 (5)	C12'—C11—C10'	116.8 (14)
C7—C2—H2	107.8	C12—C11—C10'	114.3 (14)
C1—C2—H2	107.8	C12'—C11—C11^vi	120.7 (12)
C3—C2—H2	107.8	C12—C11—C11^vi	121.1 (12)
C4—C3—C2	110.7 (5)	C10—C11—C11^vi	120.7 (12)
C4—C3—H3A	109.5	C10'—C11—C11^vi	122.5 (11)
C2—C3—H3A	109.5	C13—C12—C11	120 (2)
C4—C3—H3B	109.5	C13—C12—H12	120.2
C2—C3—H3B	109.5	C11—C12—H12	120.2
H3A—C3—H3B	108.1	N1—C13—C12	123 (2)
C5—C4—C3	111.0 (5)	N1—C13—H13	118.5
C5—C4—H4A	109.4	C12—C13—H13	118.5
C3—C4—H4A	109.4	C13'—C12'—C11	120 (2)
C5—C4—H4B	109.4	C13'—C12'—H12'	119.8
C3—C4—H4B	109.4	C11—C12'—H12'	119.8
H4A—C4—H4B	108.0	N1—C13'—C12'	122 (2)
C6—C5—C4	111.9 (5)	N1—C13'—H13'	118.9
C6—C5—H5A	109.2	C12'—C13'—H13'	118.9
C4—C5—H5A	109.2

N1—Zn1—O1—C1	171.8 (4)	C3—C2—C7—C6	56.6 (6)
O3ⁱⁱ—Zn1—O1—C1	−89.0 (4)	C5—C6—C7—C2	−54.5 (6)
O2ⁱ—Zn1—O1—C1	−5.7 (7)	C8—C6—C7—C2	177.0 (5)
O4ⁱⁱⁱ—Zn1—O1—C1	73.5 (4)	Zn1^v—O4—C8—O3	−3.1 (8)
Zn1ⁱ—Zn1—O1—C1	−6.3 (4)	Zn1^v—O4—C8—C6	173.7 (3)
O3ⁱⁱ—Zn1—N1—C13'	−0.6 (6)	Zn1^iv—O3—C8—O4	−0.9 (8)
O2ⁱ—Zn1—N1—C13'	−89.7 (6)	Zn1^iv—O3—C8—C6	−177.8 (3)
O1—Zn1—N1—C13'	91.1 (6)	C5—C6—C8—O4	16.7 (7)
O4ⁱⁱⁱ—Zn1—N1—C13'	−179.8 (6)	C7—C6—C8—O4	144.6 (5)
Zn1ⁱ—Zn1—N1—C13'	−98.8 (9)	C5—C6—C8—O3	−166.2 (5)
O3ⁱⁱ—Zn1—N1—C13	19.4 (6)	C7—C6—C8—O3	−38.3 (7)
O2ⁱ—Zn1—N1—C13	−69.6 (6)	C13'—N1—C9—C10	19.0 (10)
O1—Zn1—N1—C13	111.2 (6)	C13—N1—C9—C10	−0.1 (3)
O4ⁱⁱⁱ—Zn1—N1—C13	−159.8 (6)	Zn1—N1—C9—C10	177.0 (3)
Zn1ⁱ—Zn1—N1—C13	−78.8 (10)	N1—C9—C10—C11	−0.2 (3)
O3ⁱⁱ—Zn1—N1—C9'	−177.8 (6)	C13'—N1—C9'—C10'	−0.1 (3)
O2ⁱ—Zn1—N1—C9'	93.2 (6)	Zn1—N1—C9'—C10'	177.1 (3)
O1—Zn1—N1—C9'	−86.0 (6)	N1—C9'—C10'—C11	−0.3 (3)
O4ⁱⁱⁱ—Zn1—N1—C9'	3.0 (6)	C9—C10—C11—C12'	−18.2 (11)
Zn1ⁱ—Zn1—N1—C9'	84.0 (9)	C9—C10—C11—C12	0.6 (6)
O3ⁱⁱ—Zn1—N1—C9	−157.6 (6)	C9—C10—C11—C10'	82 (6)
O2ⁱ—Zn1—N1—C9	113.4 (6)	C9—C10—C11—C11^vi	−176.8 (5)
O1—Zn1—N1—C9	−65.9 (6)	C9'—C10'—C11—C12'	0.7 (6)
O4ⁱⁱⁱ—Zn1—N1—C9	23.2 (6)	C9'—C10'—C11—C12	19.4 (10)
Zn1ⁱ—Zn1—N1—C9	104.2 (9)	C9'—C10'—C11—C10	−87 (6)
Zn1—O1—C1—O2	13.7 (8)	C9'—C10'—C11—C11^vi	−177.0 (6)
Zn1—O1—C1—C2	−167.4 (4)	C10—C11—C12—C13	−0.6 (8)
Zn1ⁱ—O2—C1—O1	−16.9 (9)	C10'—C11—C12—C13	−19.4 (12)
Zn1ⁱ—O2—C1—C2	164.2 (4)	C11^vi—C11—C12—C13	176.7 (7)
O1—C1—C2—C7	152.2 (5)	C13'—N1—C13—C12	−86 (7)
O2—C1—C2—C7	−28.9 (7)	C9'—N1—C13—C12	19.2 (12)
O1—C1—C2—C3	28.7 (7)	C9—N1—C13—C12	0.1 (7)
O2—C1—C2—C3	−152.3 (5)	Zn1—N1—C13—C12	−177.0 (5)
C7—C2—C3—C4	−58.1 (6)	C11—C12—C13—N1	0.3 (9)
C1—C2—C3—C4	66.7 (6)	C10'—C11—C12'—C13'	−0.8 (8)
C2—C3—C4—C5	57.2 (6)	C11^vi—C11—C12'—C13'	176.9 (6)
C3—C4—C5—C6	−54.6 (7)	C9'—N1—C13'—C12'	0.0 (7)
C4—C5—C6—C8	−178.4 (5)	Zn1—N1—C13'—C12'	−177.3 (5)
C4—C5—C6—C7	53.2 (6)	C11—C12'—C13'—N1	0.5 (9)
C1—C2—C7—C6	−67.6 (6)

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₈H₁₀O₄)₂(C₁₀H₈N₂)]
M_r	313.64
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	22.251 (2), 13.436 (1), 8.552 (1)
β (°)	104.446 (5)
V (Å³)	2475.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.12 × 0.02 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.557, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8536, 2175, 1407
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.123, 0.99
No. of reflections	2175
No. of parameters	184
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.65

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XSHELL (Sheldrick, 2008), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Bailey, A. J., Lee, C., Feller, R. K., Orton, J. B., Mellot-Draznieks, C., Slater, B., Harrison, W. T. A., Simoncic, P., Navrotsky, A., Grossel, M. C. & Cheetham, A. K. (2008). Angew. Chem. Int. Ed. 47, 8634–8637. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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