Poly[tetra­kis(μ4-4,6-dimethyl-5-nitro­benzene-1,3-dicarboxyl­ato-κ2O1:O1′:O3:O3′)bis­(pyridine-κN)dizinc]

Ma, Q.-Y.; Guan, R.-F.; Li, G.-Z.

doi:10.1107/S1600536811013092

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m586

doi:10.1107/S1600536811013092

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Poly[tetrakis(μ₄-4,6-dimethyl-5-nitrobenzene-1,3-dicarboxylato-κ²O¹:O^1′:O³:O^3′)bis(pyridine-κN)dizinc]

Qing-Yu Ma,^a ^* Rui-Fang Guan ^a and Guo-Zhong Li ^a

^aSchool of Materials Science and Engineering, University of Jinan, Jinan 250100, People's Republic of China
^*Correspondence e-mail: mse_maqy@ujn.edu.cn

(Received 19 January 2011; accepted 7 April 2011; online 13 April 2011)

In the title complex, [Zn₂(C₁₀H₇NO₆)₂(C₅H₅N)₂]_n, the repeat unit is a centrosymmetic tetra-carboxylato-O,O'-bridged dimer in which each Zn^II atom is five-coordinated by four O atoms from different dianionic 4,6-dimethyl-5-nitroisophthalate ligands [Zn—O = 2.0283 (18)–2.0540 (19) Å] and one N atom from a pyridine molecule [Zn—N = 2.030 (2) Å] in the axial site of a slightly distorted square-pyramidal coordination sphere. The Zn⋯Zn separation is 2.9750 (6) Å. The complex dimers are extended into a two-dimensional polymeric structure parallel to (100) through bridges provided by the second carboxylate group of the ligand.

Related literature

For the structure of a similar but discrete tetra-carboxylato-bridged Zn₂ dimer, see: Yu et al. (2011 ).

Experimental

Crystal data

[Zn(C₁₀H₇NO₆)(C₅H₅N)]
M_r = 381.64
Monoclinic, P 2₁ /c
a = 10.2947 (9) Å
b = 11.8526 (10) Å
c = 12.8501 (11) Å
β = 97.933 (2)°
V = 1553.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.824, T_max = 0.879
8899 measured reflections
3525 independent reflections
2750 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.081
S = 1.03
3525 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: 10.1107/S1600536811013092/zs2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013092/zs2089Isup2.hkl

checkCIF report

Comment top

The title complex [Zn₂(C₁₀H₇NO₆)₂(C₅H₅N)₂]_n (I) was obtained by chance when we were attempting to prepare some porous metal-organic framework materials by the reaction of 4,6-dimethyl-5-nitroisophthalic acid with Zn(NO₃)₂. In (I), the repeating unit is a centrosymmetic tetra-carboxylato O,O' bridged dimer (Fig. 1) in which each Zn^II is five-coordinated by four O atoms from different dianionic 4,6-dimethyl-5-nitroisophthalate ligands [Zn—O, 2.0283 (18)–2.0540 (19) Å] and one N atom from a pyridine molecule [Zn—N, 2.030 (2) Å] in the axial site of a slightly distorted square pyramidal coordination sphere. Each of the Zn atoms has an approximately square-pyramidal environment, with four O atoms in a plane and the pyridine N atom at the apical site. The Zn—Zn separation in the dimer is 2.9750 (6) Å. This dimeric unit is similar to that found in the structure of the tetra-benzoato-bridged but discrete Zn₂ dimer with 4-(dimethylamino)pyridine (Yu et al., 2011). The complex dimers in (I) are extended into a two-dimensional polymer structure through bridges provided by the second carboxylate group of the ligand (Figs. 2, 3).

Related literature top

For the structure of a similar but discrete tetra-carboxylato-bridged Zn₂ dimer, see: Yu et al. (2011).

Experimental top

4,6-Dimethyl-5-nitroisophthalic acid (2 mg, 0.0046 mmol) and Zn(NO₃)₂ (4 mg, 0.0137 mmol) were dissolved in 1 ml of a mixed DMSO–H₂O solvent (2:1) and 2 drops pyridine were added. This solution was sealed in a Pyrex glass tube and heated to 120° C over a period of 10 h, and then maintained at this temperature for 50 h, after which it was cooled to room temperature over 17 h. Colourless rod crystals were obtained, which were filtered, washed with water and dried in air.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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. The atom numbering scheme for the centrosymmetric dimeric unit in the title compound with displacement ellipsoids drawn at the 30% probability level. Symmetry codes are: (i) -x+1, -y, -z + 1; (ii) -x + 1, y - 1/2, -z - 3/2; (iii) x, -y + 1/2, z + 1/2. The second set of hydrogen atoms on the 50% rotationally-disordered methyl groups (C8 and C9) are omitted.
	Fig. 2. The two-dimensional polymeric extension of the title compound viewed down the a axial direction.
	Fig. 3. The packed structure of the title compound viewed down the c axial direction.

Poly[tetrakis(µ₄-4,6-dimethyl-5-nitrobenzene-1,3-dicarboxylato- κ²O¹:O^1':O³:O^3')bis(pyridine- κN)dizinc] top

Crystal data top

[Zn(C₁₀H₇NO₆)(C₅H₅N)]	F(000) = 776
M_r = 381.64	D_x = 1.632 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2968 reflections
a = 10.2947 (9) Å	θ = 2.3–26.1°
b = 11.8526 (10) Å	µ = 1.62 mm⁻¹
c = 12.8501 (11) Å	T = 298 K
β = 97.933 (2)°	Rod, colourless
V = 1553.0 (2) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3525 independent reflections
Radiation source: fine-focus sealed tube	2750 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.7°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→13
T_min = 0.824, T_max = 0.879	k = −15→15
8899 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0353P)² + 0.6981P] where P = (F_o² + 2F_c²)/3
3525 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Zn(C₁₀H₇NO₆)(C₅H₅N)]	V = 1553.0 (2) Å³
M_r = 381.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2947 (9) Å	µ = 1.62 mm⁻¹
b = 11.8526 (10) Å	T = 298 K
c = 12.8501 (11) Å	0.12 × 0.10 × 0.08 mm
β = 97.933 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3525 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2750 reflections with I > 2σ(I)
T_min = 0.824, T_max = 0.879	R_int = 0.029
8899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
3525 reflections	Δρ_min = −0.43 e Å⁻³
217 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
Zn1	0.63668 (3)	−0.03544 (2)	0.53898 (2)	0.0233 (1)
O1	0.65410 (19)	0.13708 (16)	0.54695 (18)	0.0546 (8)
O2	0.4496 (2)	0.18909 (15)	0.49411 (17)	0.0508 (7)
O3	0.55390 (18)	−0.03094 (18)	0.67374 (14)	0.0454 (7)
O4	0.6491 (2)	−0.02213 (19)	0.38329 (14)	0.0499 (7)
O5	0.7497 (2)	0.62087 (19)	0.42547 (16)	0.0600 (8)
O6	0.9095 (2)	0.5865 (2)	0.5453 (2)	0.0703 (10)
N1	0.7959 (2)	0.57613 (18)	0.50579 (17)	0.0352 (7)
N2	0.8232 (2)	−0.07998 (17)	0.59645 (16)	0.0298 (6)
C1	0.5998 (2)	0.32743 (18)	0.56737 (17)	0.0245 (7)
C2	0.6751 (2)	0.39863 (19)	0.51257 (17)	0.0253 (7)
C3	0.7112 (2)	0.50127 (19)	0.56086 (18)	0.0258 (7)
C4	0.6795 (2)	0.53868 (18)	0.65714 (17)	0.0253 (7)
C5	0.5997 (2)	0.46553 (19)	0.70674 (17)	0.0235 (6)
C6	0.5600 (2)	0.36307 (19)	0.66100 (17)	0.0260 (7)
C7	0.5647 (3)	0.2080 (2)	0.53197 (18)	0.0283 (7)
C8	0.7134 (3)	0.3664 (2)	0.4076 (2)	0.0382 (9)
C9	0.7241 (3)	0.6519 (2)	0.7019 (2)	0.0416 (9)
C10	0.5618 (2)	0.48883 (19)	0.81384 (17)	0.0259 (7)
C11	0.9056 (3)	−0.1198 (3)	0.5336 (2)	0.0455 (10)
C12	1.0338 (3)	−0.1460 (3)	0.5712 (3)	0.0625 (14)
C13	1.0764 (3)	−0.1350 (3)	0.6760 (3)	0.0739 (15)
C14	0.9916 (4)	−0.0970 (4)	0.7408 (3)	0.0817 (14)
C15	0.8655 (3)	−0.0695 (3)	0.6982 (2)	0.0559 (11)
H6A	0.50520	0.31680	0.69400	0.0310*
H8A	0.67890	0.29300	0.38790	0.0570*	0.500
H8B	0.80720	0.36510	0.41230	0.0570*	0.500
H8C	0.67830	0.42060	0.35570	0.0570*	0.500
H8D	0.76410	0.42610	0.38270	0.0570*	0.500
H8E	0.63580	0.35410	0.35830	0.0570*	0.500
H8F	0.76460	0.29850	0.41490	0.0570*	0.500
H9A	0.69250	0.66260	0.76810	0.0620*	0.500
H9B	0.69000	0.71040	0.65410	0.0620*	0.500
H9C	0.81820	0.65490	0.71220	0.0620*	0.500
H9D	0.77470	0.68930	0.65480	0.0620*	0.500
H9E	0.77710	0.64150	0.76880	0.0620*	0.500
H9F	0.64890	0.69700	0.71080	0.0620*	0.500
H11A	0.87570	−0.13000	0.46260	0.0550*
H12A	1.09060	−0.17090	0.52580	0.0750*
H13A	1.16230	−0.15320	0.70300	0.0890*
H14A	1.01850	−0.08980	0.81260	0.0980*
H15A	0.80810	−0.04270	0.74230	0.0670*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0253 (2)	0.0240 (2)	0.0210 (1)	0.0011 (1)	0.0044 (1)	0.0003 (1)
O1	0.0406 (12)	0.0231 (10)	0.0991 (18)	0.0015 (9)	0.0057 (12)	−0.0082 (10)
O2	0.0471 (12)	0.0278 (10)	0.0708 (14)	−0.0077 (9)	−0.0156 (10)	−0.0060 (9)
O3	0.0346 (10)	0.0791 (15)	0.0245 (9)	0.0051 (10)	0.0108 (8)	0.0017 (9)
O4	0.0510 (12)	0.0788 (15)	0.0218 (9)	0.0216 (11)	0.0114 (9)	0.0125 (9)
O5	0.0789 (16)	0.0588 (14)	0.0439 (12)	−0.0111 (12)	0.0142 (11)	0.0230 (11)
O6	0.0460 (14)	0.0838 (18)	0.0819 (18)	−0.0243 (13)	0.0113 (13)	0.0200 (15)
N1	0.0456 (14)	0.0298 (11)	0.0338 (12)	−0.0076 (10)	0.0185 (10)	−0.0013 (9)
N2	0.0285 (11)	0.0286 (10)	0.0324 (11)	0.0014 (9)	0.0047 (9)	−0.0001 (9)
C1	0.0281 (12)	0.0225 (11)	0.0229 (11)	−0.0012 (9)	0.0036 (9)	−0.0028 (9)
C2	0.0302 (12)	0.0246 (12)	0.0220 (11)	0.0007 (10)	0.0064 (9)	−0.0024 (9)
C3	0.0298 (13)	0.0227 (11)	0.0261 (12)	−0.0020 (9)	0.0077 (10)	0.0036 (9)
C4	0.0317 (13)	0.0204 (11)	0.0239 (11)	−0.0007 (10)	0.0043 (9)	−0.0005 (9)
C5	0.0278 (12)	0.0243 (11)	0.0189 (10)	0.0017 (10)	0.0047 (9)	−0.0002 (9)
C6	0.0303 (13)	0.0243 (12)	0.0244 (12)	−0.0048 (9)	0.0079 (10)	0.0010 (9)
C7	0.0412 (15)	0.0237 (12)	0.0215 (11)	−0.0049 (11)	0.0100 (10)	−0.0010 (9)
C8	0.0552 (18)	0.0334 (14)	0.0293 (13)	0.0001 (12)	0.0171 (12)	−0.0026 (11)
C9	0.0616 (19)	0.0268 (13)	0.0390 (15)	−0.0123 (13)	0.0160 (14)	−0.0078 (11)
C10	0.0355 (14)	0.0236 (12)	0.0195 (11)	0.0024 (10)	0.0075 (10)	0.0011 (9)
C11	0.0412 (17)	0.0514 (18)	0.0456 (16)	0.0133 (14)	0.0122 (13)	0.0050 (14)
C12	0.0423 (19)	0.066 (2)	0.083 (3)	0.0198 (16)	0.0219 (18)	0.004 (2)
C13	0.0309 (18)	0.073 (3)	0.111 (3)	0.0081 (17)	−0.0148 (19)	−0.020 (2)
C14	0.053 (2)	0.110 (3)	0.071 (2)	0.023 (2)	−0.0308 (19)	−0.039 (2)
C15	0.0443 (18)	0.074 (2)	0.0458 (18)	0.0131 (16)	−0.0064 (14)	−0.0239 (16)

Geometric parameters (Å, º) top

Zn1—O1	2.0540 (19)	C5—C10	1.507 (3)
Zn1—O3	2.0336 (18)	C11—C12	1.377 (4)
Zn1—O4	2.0283 (18)	C12—C13	1.364 (5)
Zn1—N2	2.030 (2)	C13—C14	1.363 (5)
Zn1—O2ⁱ	2.0450 (19)	C14—C15	1.377 (5)
O1—C7	1.242 (3)	C6—H6A	0.9300
O2—C7	1.238 (4)	C8—H8A	0.9600
O3—C10ⁱⁱ	1.246 (3)	C8—H8B	0.9600
O4—C10ⁱⁱⁱ	1.240 (3)	C8—H8C	0.9600
O5—N1	1.199 (3)	C8—H8D	0.9600
O6—N1	1.215 (3)	C8—H8E	0.9600
N1—C3	1.490 (3)	C8—H8F	0.9600
N2—C11	1.336 (4)	C9—H9A	0.9600
N2—C15	1.326 (3)	C9—H9B	0.9600
C1—C2	1.400 (3)	C9—H9C	0.9600
C1—C6	1.389 (3)	C9—H9D	0.9600
C1—C7	1.515 (3)	C9—H9E	0.9600
C2—C3	1.393 (3)	C9—H9F	0.9600
C2—C8	1.506 (3)	C11—H11A	0.9300
C3—C4	1.395 (3)	C12—H12A	0.9300
C4—C5	1.406 (3)	C13—H13A	0.9300
C4—C9	1.507 (3)	C14—H14A	0.9300
C5—C6	1.386 (3)	C15—H15A	0.9300

O1—Zn1—O3	88.59 (9)	N2—C11—C12	121.7 (3)
O1—Zn1—O4	87.41 (9)	C11—C12—C13	119.1 (3)
O1—Zn1—N2	99.73 (8)	C12—C13—C14	119.3 (3)
O1—Zn1—O2ⁱ	158.34 (8)	C13—C14—C15	118.9 (3)
O3—Zn1—O4	158.24 (8)	N2—C15—C14	122.2 (3)
O3—Zn1—N2	100.58 (8)	C1—C6—H6A	119.00
O2ⁱ—Zn1—O3	88.82 (8)	C5—C6—H6A	119.00
O4—Zn1—N2	101.18 (8)	C2—C8—H8A	109.00
O2ⁱ—Zn1—O4	87.07 (9)	C2—C8—H8B	109.00
O2ⁱ—Zn1—N2	101.89 (8)	C2—C8—H8C	109.00
Zn1—O1—C7	127.48 (18)	C2—C8—H8D	109.00
Zn1ⁱ—O2—C7	127.43 (17)	C2—C8—H8E	109.00
Zn1—O3—C10ⁱⁱ	129.39 (16)	C2—C8—H8F	109.00
Zn1—O4—C10ⁱⁱⁱ	126.61 (17)	H8A—C8—H8B	110.00
O5—N1—O6	124.0 (2)	H8A—C8—H8C	109.00
O5—N1—C3	118.9 (2)	H8B—C8—H8C	109.00
O6—N1—C3	117.0 (2)	H8D—C8—H8E	109.00
Zn1—N2—C11	121.32 (17)	H8D—C8—H8F	110.00
Zn1—N2—C15	120.00 (19)	H8E—C8—H8F	109.00
C11—N2—C15	118.7 (2)	C4—C9—H9A	109.00
C2—C1—C6	120.2 (2)	C4—C9—H9B	109.00
C2—C1—C7	122.5 (2)	C4—C9—H9C	110.00
C6—C1—C7	117.2 (2)	C4—C9—H9D	110.00
C1—C2—C3	115.8 (2)	C4—C9—H9E	109.00
C1—C2—C8	122.0 (2)	C4—C9—H9F	109.00
C3—C2—C8	122.3 (2)	H9A—C9—H9B	109.00
N1—C3—C2	116.51 (19)	H9A—C9—H9C	109.00
N1—C3—C4	117.13 (19)	H9B—C9—H9C	110.00
C2—C3—C4	126.3 (2)	H9D—C9—H9E	109.00
C3—C4—C5	115.4 (2)	H9D—C9—H9F	110.00
C3—C4—C9	121.7 (2)	H9E—C9—H9F	109.00
C5—C4—C9	122.9 (2)	N2—C11—H11A	119.00
C4—C5—C6	120.3 (2)	C12—C11—H11A	119.00
C4—C5—C10	122.8 (2)	C11—C12—H12A	120.00
C6—C5—C10	116.71 (19)	C13—C12—H12A	120.00
C1—C6—C5	121.9 (2)	C12—C13—H13A	120.00
O1—C7—O2	126.0 (2)	C14—C13—H13A	120.00
O1—C7—C1	116.4 (2)	C13—C14—H14A	121.00
O2—C7—C1	117.6 (2)	C15—C14—H14A	121.00
O3^iv—C10—C5	117.08 (19)	N2—C15—H15A	119.00
O4^v—C10—C5	117.53 (19)	C14—C15—H15A	119.00
O3^iv—C10—O4^v	125.3 (2)

O3—Zn1—O1—C7	−70.9 (2)	C15—N2—C11—C12	−2.4 (5)
O4—Zn1—O1—C7	87.7 (2)	C11—N2—C15—C14	0.8 (5)
N2—Zn1—O1—C7	−171.4 (2)	Zn1—N2—C11—C12	177.4 (3)
O2ⁱ—Zn1—O1—C7	12.3 (4)	Zn1—N2—C15—C14	−179.1 (3)
O1—Zn1—O3—C10ⁱⁱ	82.6 (2)	C2—C1—C6—C5	−4.3 (3)
O4—Zn1—O3—C10ⁱⁱ	3.2 (4)	C2—C1—C7—O1	74.4 (3)
N2—Zn1—O3—C10ⁱⁱ	−177.8 (2)	C7—C1—C2—C8	7.3 (3)
O2ⁱ—Zn1—O3—C10ⁱⁱ	−75.9 (2)	C7—C1—C6—C5	172.4 (2)
O1—Zn1—O4—C10ⁱⁱⁱ	−75.2 (2)	C6—C1—C2—C3	3.3 (3)
O3—Zn1—O4—C10ⁱⁱⁱ	4.4 (4)	C6—C1—C7—O2	75.5 (3)
N2—Zn1—O4—C10ⁱⁱⁱ	−174.7 (2)	C7—C1—C2—C3	−173.3 (2)
O2ⁱ—Zn1—O4—C10ⁱⁱⁱ	83.8 (2)	C6—C1—C2—C8	−176.2 (2)
O1—Zn1—N2—C11	−106.3 (2)	C6—C1—C7—O1	−102.3 (3)
O1—Zn1—N2—C15	73.6 (2)	C2—C1—C7—O2	−107.9 (3)
O3—Zn1—N2—C11	163.4 (2)	C8—C2—C3—C4	179.4 (2)
O3—Zn1—N2—C15	−16.8 (2)	C8—C2—C3—N1	−2.9 (3)
O4—Zn1—N2—C11	−17.0 (2)	C1—C2—C3—C4	0.0 (3)
O4—Zn1—N2—C15	162.8 (2)	C1—C2—C3—N1	177.59 (19)
O2ⁱ—Zn1—N2—C11	72.3 (2)	N1—C3—C4—C9	2.4 (3)
O2ⁱ—Zn1—N2—C15	−107.8 (2)	C2—C3—C4—C5	−2.2 (3)
O1—Zn1—O2ⁱ—C7ⁱ	−3.3 (4)	C2—C3—C4—C9	−180.0 (2)
O3—Zn1—O2ⁱ—C7ⁱ	79.9 (2)	N1—C3—C4—C5	−179.84 (19)
O4—Zn1—O2ⁱ—C7ⁱ	−78.7 (2)	C3—C4—C5—C6	1.3 (3)
N2—Zn1—O2ⁱ—C7ⁱ	−179.5 (2)	C9—C4—C5—C6	179.0 (2)
Zn1—O1—C7—O2	−11.5 (4)	C3—C4—C5—C10	176.5 (2)
Zn1—O1—C7—C1	166.09 (17)	C9—C4—C5—C10	−5.8 (3)
Zn1ⁱ—O2—C7—O1	8.2 (4)	C10—C5—C6—C1	−173.6 (2)
Zn1ⁱ—O2—C7—C1	−169.35 (16)	C4—C5—C10—O3^iv	138.0 (2)
Zn1—O3—C10ⁱⁱ—C5ⁱⁱ	169.14 (16)	C4—C5—C10—O4^v	−44.5 (3)
Zn1—O3—C10ⁱⁱ—O4ⁱ	−8.1 (4)	C6—C5—C10—O3^iv	−46.6 (3)
Zn1—O4—C10ⁱⁱⁱ—O3ⁱ	−8.2 (4)	C6—C5—C10—O4^v	130.9 (2)
Zn1—O4—C10ⁱⁱⁱ—C5ⁱⁱⁱ	169.07 (16)	C4—C5—C6—C1	1.9 (3)
O6—N1—C3—C2	−108.6 (3)	N2—C11—C12—C13	2.5 (5)
O5—N1—C3—C4	−111.8 (3)	C11—C12—C13—C14	−0.8 (6)
O6—N1—C3—C4	69.3 (3)	C12—C13—C14—C15	−0.8 (6)
O5—N1—C3—C2	70.4 (3)	C13—C14—C15—N2	0.8 (6)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₇NO₆)(C₅H₅N)]
M_r	381.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.2947 (9), 11.8526 (10), 12.8501 (11)
β (°)	97.933 (2)
V (Å³)	1553.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.824, 0.879
No. of measured, independent and observed [I > 2σ(I)] reflections	8899, 3525, 2750
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.081, 1.03
No. of reflections	3525
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.43

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Scientific and Technological Project of Shandong Province (2008SGG0809) and Doctoral Foundation of Shandong Province (2009SBS0913).

References

Bruker (2007). APEX2 and SAINT-Plus. 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
Yu, Z.-Y., Lin, K.-H., Zhang, F.-F., Shao, M. & Li, M. (2011). Acta Cryst. E67, m206. Web of Science CSD CrossRef IUCr Journals Google Scholar

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