Poly[bis­(N,N-dimethyl­formamide)(μ-formato)(μ5-4-oxidoisophthalato)dizinc(II)]

Jhon, Y.H.; Kim, J.

doi:10.1107/S1600536809028566

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m990

doi:10.1107/S1600536809028566

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Poly[bis(N,N-dimethylformamide)(μ-formato)(μ₅-4-oxidoisophthalato)dizinc(II)]

Young Ho Jhon ^a and Jaheon Kim ^a ^*

^aDepartment of Chemistry, and CAMDRC, Soongsil University, 511 Sangdo-dong, Dongjak-Ku, Seoul 156-743, Republic of Korea
^*Correspondence e-mail: jaheon@ssu.ac.kr

(Received 16 July 2009; accepted 20 July 2009; online 25 July 2009)

The title compound, [Zn₂(CHO₂)(C₈H₃O₅)(C₃H₇NO)₂]_n, is a three-dimensional metal–organic framework, of which two independent Zn^II atoms (denoted Zn1 and Zn2) are linked by both 4-oxidoisophthalate and formate bridging ligands. The 4-oxidoisophthalate ligands link two Zn1-type and three Zn2-type atoms, forming a corrugated sheet roughly parallel to the ac plane. The formate ions join two neighboring sheets along the b axis, forming a three-dimensional network. Two independent dimethylformamide ligands are coordinated to separate Zn^II atoms and fill the voids provided by the framework. Both types of Zn^II atoms have a distorted trigonal-bipyramidal coordination geometry.

Related literature

Zn ions and 4-hydroxyisophthalates can be assembled in a different way due to an auxiliary pyridyl ligand; see: Zhang et al. (2004 ).

Experimental

Crystal data

[Zn₂(CHO₂)(C₈H₃O₅)(C₃H₇NO)₂]
M_r = 501.05
Monoclinic, P 2₁ /n
a = 9.1190 (4) Å
b = 14.7355 (6) Å
c = 14.4711 (6) Å
β = 107.752 (1)°
V = 1851.94 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 173 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.551, T_max = 0.768
9831 measured reflections
3343 independent reflections
2881 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.097
S = 1.18
3343 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.99 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O4ⁱ	1.960 (3)
Zn1—O2	1.972 (3)
Zn1—O6	1.977 (3)
Zn1—O1	2.083 (2)
Zn1—O8	2.127 (3)
Zn2—O5ⁱ	1.978 (3)
Zn2—O1	2.029 (3)
Zn2—O3ⁱⁱ	2.038 (3)
Zn2—O7ⁱⁱⁱ	2.075 (3)
Zn2—O9	2.114 (3)
Symmetry codes: (i) x+1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 and MS Modeling (Accelrys, 2005 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028566/xu2557sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028566/xu2557Isup2.hkl

checkCIF report

Related literature top

Zn ions and 4-hydroxyisophthalates can be assembled in a different way due to an auxiliary pyridyl ligand; see: Zhang et al. (2004).

Experimental top

The hydroxybenzene-2,4-dicarboxylic acid was purchased from TCI. Hydroxybenzene-2,4-dicarboxylic acid (10 mg, 0.06 mmol) and Zn(NO₃)₂.6H₂O (32 mg, 0.11 mmol) were dissolved in the mixture of N,N'-dimethylformamide (1.0 ml) and H₂O (0.05 ml) solution in 20 ml vial. Then the vial was capped tightly, and placed at 105 °C for 7 days to obtain the crystals for the X-ray crystallographic study.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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) and MS Modeling (Accelrys, 2005).

Figures top

Fig. 1. The fragment structure of (I) is shown with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) x + 1, y, z; (ii) x + 1/2, -y + 3/2, z + 1/2; (iii) -x + 3/2, y + 1/2, -z + 3/2; (iv) x - 1/2, -y + 3/2, z - 1/2; (v) x - 1, y, z; (vi) -x + 3/2, y - 1/2, -z + 3/2]

Poly[bis(N,N-dimethylformamide)(µ-formato)(µ₅-4- oxidoisophthalato)dizinc(II)] top

Crystal data top

[Zn₂(CHO₂)(C₈H₃O₅)(C₃H₇NO)₂]	F(000) = 1016
M_r = 501.05	D_x = 1.797 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5137 reflections
a = 9.1190 (4) Å	θ = 2.4–28.3°
b = 14.7355 (6) Å	µ = 2.64 mm⁻¹
c = 14.4711 (6) Å	T = 173 K
β = 107.752 (1)°	Rectangular, light yellow
V = 1851.94 (13) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.551, T_max = 0.768	k = −17→13
9831 measured reflections	l = −16→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0404P)² + 1.5088P] where P = (F_o² + 2F_c²)/3
3343 reflections	(Δ/σ)_max = 0.011
257 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.99 e Å⁻³

Crystal data top

[Zn₂(CHO₂)(C₈H₃O₅)(C₃H₇NO)₂]	V = 1851.94 (13) Å³
M_r = 501.05	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1190 (4) Å	µ = 2.64 mm⁻¹
b = 14.7355 (6) Å	T = 173 K
c = 14.4711 (6) Å	0.25 × 0.20 × 0.10 mm
β = 107.752 (1)°

Data collection top

Bruker SMART CCD diffractometer	3343 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2881 reflections with I > 2σ(I)
T_min = 0.551, T_max = 0.768	R_int = 0.066
9831 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.18	Δρ_max = 0.76 e Å⁻³
3343 reflections	Δρ_min = −0.99 e Å⁻³
257 parameters

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	0.72276 (5)	0.65094 (3)	0.63563 (3)	0.01168 (14)
Zn2	0.81689 (5)	0.74739 (3)	0.86581 (3)	0.01100 (14)
O1	0.6482 (3)	0.70324 (18)	0.74736 (18)	0.0122 (6)
O2	0.5239 (3)	0.69042 (19)	0.54535 (18)	0.0154 (6)
O3	0.2738 (3)	0.7065 (2)	0.48774 (18)	0.0170 (6)
O4	−0.0743 (3)	0.7091 (2)	0.67563 (19)	0.0205 (7)
O5	0.0125 (3)	0.7240 (2)	0.83755 (19)	0.0178 (6)
O6	0.7196 (4)	0.5270 (2)	0.6874 (2)	0.0311 (8)
O7	0.7029 (4)	0.3780 (2)	0.6904 (2)	0.0240 (7)
O8	0.7888 (3)	0.6054 (2)	0.51459 (19)	0.0209 (7)
O9	0.8384 (4)	0.6248 (2)	0.9446 (2)	0.0255 (7)
N1	0.7454 (4)	0.5608 (2)	0.3589 (2)	0.0209 (8)
N2	0.7907 (5)	0.4794 (3)	0.9734 (3)	0.0256 (9)
C1	0.5022 (4)	0.7046 (3)	0.7454 (3)	0.0114 (8)
C2	0.3757 (4)	0.7015 (3)	0.6584 (3)	0.0110 (8)
C3	0.2254 (4)	0.7048 (3)	0.6639 (3)	0.0123 (8)
H3	0.1419	0.7020	0.6055	0.015*
C4	0.1940 (4)	0.7121 (3)	0.7516 (3)	0.0129 (8)
C5	0.3178 (4)	0.7163 (3)	0.8370 (3)	0.0143 (8)
H5	0.2987	0.7221	0.8976	0.017*
C6	0.4675 (4)	0.7120 (3)	0.8342 (3)	0.0145 (8)
H6	0.5495	0.7139	0.8933	0.017*
C7	0.3937 (4)	0.6988 (3)	0.5587 (3)	0.0108 (8)
C8	0.0325 (4)	0.7156 (3)	0.7551 (3)	0.0130 (8)
C9	0.7218 (4)	0.4501 (3)	0.6507 (3)	0.0163 (9)
H9	0.7389	0.4467	0.5893	0.020*
C10	0.7002 (5)	0.5902 (3)	0.4312 (3)	0.0178 (9)
H10	0.5933	0.6007	0.4196	0.021*
C11	0.9072 (5)	0.5454 (3)	0.3685 (3)	0.0322 (12)
H11A	0.9713	0.5693	0.4310	0.039*
H11B	0.9334	0.5765	0.3157	0.039*
H11C	0.9258	0.4802	0.3652	0.039*
C12	0.6343 (6)	0.5446 (3)	0.2635 (3)	0.0292 (11)
H12A	0.5303	0.5583	0.2659	0.035*
H12B	0.6395	0.4809	0.2453	0.035*
H12C	0.6584	0.5838	0.2154	0.035*
C13	0.8027 (5)	0.5464 (3)	0.9161 (3)	0.0238 (10)
H13	0.7829	0.5339	0.8490	0.029*
C14	0.8165 (8)	0.4940 (4)	1.0762 (4)	0.0464 (15)
H14A	0.8540	0.5560	1.0933	0.056*
H14B	0.8933	0.4506	1.1134	0.056*
H14C	0.7197	0.4853	1.0912	0.056*
C15	0.7510 (7)	0.3869 (3)	0.9373 (4)	0.0399 (13)
H15A	0.7490	0.3835	0.8693	0.048*
H15B	0.6493	0.3709	0.9422	0.048*
H15C	0.8280	0.3444	0.9761	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0099 (2)	0.0170 (3)	0.0074 (2)	0.00076 (18)	0.00155 (16)	−0.00134 (18)
Zn2	0.0099 (2)	0.0173 (3)	0.0057 (2)	−0.00064 (17)	0.00219 (16)	−0.00158 (17)
O1	0.0084 (13)	0.0204 (16)	0.0076 (13)	0.0010 (11)	0.0020 (10)	−0.0036 (11)
O2	0.0117 (14)	0.0273 (17)	0.0078 (13)	0.0023 (11)	0.0038 (11)	0.0010 (12)
O3	0.0114 (14)	0.0310 (18)	0.0074 (13)	0.0011 (12)	0.0012 (11)	0.0015 (12)
O4	0.0092 (14)	0.040 (2)	0.0103 (14)	−0.0031 (12)	0.0003 (11)	−0.0018 (13)
O5	0.0139 (14)	0.0320 (18)	0.0095 (14)	0.0036 (12)	0.0066 (11)	0.0023 (12)
O6	0.064 (2)	0.0158 (18)	0.0153 (16)	0.0015 (15)	0.0140 (16)	−0.0019 (13)
O7	0.0392 (19)	0.0185 (17)	0.0145 (15)	0.0019 (13)	0.0087 (13)	0.0021 (12)
O8	0.0177 (15)	0.0326 (19)	0.0118 (14)	0.0054 (13)	0.0038 (12)	−0.0032 (13)
O9	0.0361 (19)	0.0203 (18)	0.0192 (16)	0.0002 (14)	0.0069 (14)	0.0039 (13)
N1	0.028 (2)	0.022 (2)	0.0132 (17)	0.0032 (15)	0.0076 (15)	−0.0039 (15)
N2	0.043 (2)	0.018 (2)	0.0175 (19)	0.0009 (17)	0.0119 (17)	0.0012 (15)
C1	0.0093 (19)	0.012 (2)	0.0129 (19)	−0.0008 (15)	0.0030 (15)	−0.0017 (15)
C2	0.016 (2)	0.011 (2)	0.0060 (18)	−0.0021 (15)	0.0038 (15)	−0.0003 (15)
C3	0.0117 (19)	0.016 (2)	0.0080 (18)	−0.0010 (15)	0.0008 (15)	−0.0016 (15)
C4	0.013 (2)	0.016 (2)	0.0106 (19)	0.0001 (15)	0.0047 (15)	0.0002 (15)
C5	0.016 (2)	0.018 (2)	0.0096 (19)	−0.0024 (16)	0.0051 (16)	−0.0021 (16)
C6	0.0105 (19)	0.024 (2)	0.0062 (18)	0.0013 (16)	−0.0011 (15)	−0.0032 (16)
C7	0.014 (2)	0.011 (2)	0.0069 (18)	0.0002 (15)	0.0035 (15)	0.0006 (15)
C8	0.012 (2)	0.015 (2)	0.013 (2)	0.0000 (15)	0.0051 (16)	0.0011 (15)
C9	0.018 (2)	0.020 (2)	0.0104 (19)	−0.0015 (17)	0.0038 (16)	−0.0009 (17)
C10	0.018 (2)	0.020 (2)	0.017 (2)	0.0017 (17)	0.0082 (17)	0.0006 (17)
C11	0.031 (3)	0.044 (3)	0.025 (2)	0.009 (2)	0.014 (2)	−0.004 (2)
C12	0.037 (3)	0.037 (3)	0.015 (2)	0.002 (2)	0.008 (2)	−0.008 (2)
C13	0.030 (3)	0.031 (3)	0.009 (2)	0.002 (2)	0.0045 (18)	0.0003 (19)
C14	0.095 (5)	0.026 (3)	0.026 (3)	0.000 (3)	0.031 (3)	0.003 (2)
C15	0.065 (4)	0.024 (3)	0.024 (3)	−0.008 (2)	0.003 (2)	0.004 (2)

Geometric parameters (Å, º) top

Zn1—O4ⁱ	1.960 (3)	N2—C15	1.465 (6)
Zn1—O2	1.972 (3)	C1—C6	1.418 (5)
Zn1—O6	1.977 (3)	C1—C2	1.425 (5)
Zn1—O1	2.083 (2)	C2—C3	1.397 (5)
Zn1—O8	2.127 (3)	C2—C7	1.502 (5)
Zn2—O5ⁱ	1.978 (3)	C3—C4	1.389 (5)
Zn2—O1	2.029 (3)	C3—H3	0.9500
Zn2—O3ⁱⁱ	2.038 (3)	C4—C5	1.398 (5)
Zn2—O7ⁱⁱⁱ	2.075 (3)	C4—C8	1.489 (5)
Zn2—O9	2.114 (3)	C5—C6	1.379 (5)
O1—C1	1.323 (4)	C5—H5	0.9500
O2—C7	1.266 (4)	C6—H6	0.9500
O3—C7	1.256 (4)	C9—H9	0.9500
O3—Zn2^iv	2.038 (3)	C10—H10	0.9500
O4—C8	1.264 (5)	C11—H11A	0.9800
O4—Zn1^v	1.960 (3)	C11—H11B	0.9800
O5—C8	1.267 (4)	C11—H11C	0.9800
O5—Zn2^v	1.978 (3)	C12—H12A	0.9800
O6—C9	1.255 (5)	C12—H12B	0.9800
O7—C9	1.244 (5)	C12—H12C	0.9800
O7—Zn2^vi	2.075 (3)	C13—H13	0.9500
O8—C10	1.250 (5)	C14—H14A	0.9800
O9—C13	1.236 (5)	C14—H14B	0.9800
N1—C10	1.311 (5)	C14—H14C	0.9800
N1—C11	1.457 (6)	C15—H15A	0.9800
N1—C12	1.462 (6)	C15—H15B	0.9800
N2—C13	1.316 (6)	C15—H15C	0.9800
N2—C14	1.448 (6)

O4ⁱ—Zn1—O2	131.40 (12)	C3—C4—C8	121.0 (3)
O4ⁱ—Zn1—O6	114.44 (14)	C5—C4—C8	120.6 (3)
O2—Zn1—O6	114.00 (13)	C6—C5—C4	120.8 (3)
O4ⁱ—Zn1—O1	96.38 (11)	C6—C5—H5	119.6
O2—Zn1—O1	87.33 (10)	C4—C5—H5	119.6
O6—Zn1—O1	90.09 (12)	C5—C6—C1	121.8 (3)
O4ⁱ—Zn1—O8	84.39 (11)	C5—C6—H6	119.1
O2—Zn1—O8	88.94 (10)	C1—C6—H6	119.1
O6—Zn1—O8	93.51 (12)	O3—C7—O2	120.5 (3)
O1—Zn1—O8	175.63 (11)	O3—C7—C2	117.4 (3)
O5ⁱ—Zn2—O1	105.56 (11)	O2—C7—C2	122.1 (3)
O5ⁱ—Zn2—O3ⁱⁱ	131.40 (11)	O4—C8—O5	124.9 (3)
O1—Zn2—O3ⁱⁱ	122.80 (10)	O4—C8—C4	117.5 (3)
O5ⁱ—Zn2—O7ⁱⁱⁱ	93.28 (12)	O5—C8—C4	117.6 (3)
O1—Zn2—O7ⁱⁱⁱ	90.76 (11)	O7—C9—O6	123.7 (4)
O3ⁱⁱ—Zn2—O7ⁱⁱⁱ	90.77 (11)	O7—C9—H9	118.2
O5ⁱ—Zn2—O9	91.22 (12)	O6—C9—H9	118.2
O1—Zn2—O9	95.94 (12)	O8—C10—N1	124.1 (4)
O3ⁱⁱ—Zn2—O9	80.11 (12)	O8—C10—H10	117.9
O7ⁱⁱⁱ—Zn2—O9	170.64 (11)	N1—C10—H10	117.9
C1—O1—Zn2	120.8 (2)	N1—C11—H11A	109.5
C1—O1—Zn1	123.6 (2)	N1—C11—H11B	109.5
Zn2—O1—Zn1	115.56 (11)	H11A—C11—H11B	109.5
C7—O2—Zn1	130.1 (2)	N1—C11—H11C	109.5
C7—O3—Zn2^iv	112.9 (2)	H11A—C11—H11C	109.5
C8—O4—Zn1^v	134.3 (3)	H11B—C11—H11C	109.5
C8—O5—Zn2^v	127.6 (3)	N1—C12—H12A	109.5
C9—O6—Zn1	132.1 (3)	N1—C12—H12B	109.5
C9—O7—Zn2^vi	128.2 (3)	H12A—C12—H12B	109.5
C10—O8—Zn1	126.1 (3)	N1—C12—H12C	109.5
C13—O9—Zn2	130.3 (3)	H12A—C12—H12C	109.5
C10—N1—C11	122.1 (4)	H12B—C12—H12C	109.5
C10—N1—C12	120.8 (4)	O9—C13—N2	123.6 (4)
C11—N1—C12	117.1 (3)	O9—C13—H13	118.2
C13—N2—C14	121.1 (4)	N2—C13—H13	118.2
C13—N2—C15	122.1 (4)	N2—C14—H14A	109.5
C14—N2—C15	116.7 (4)	N2—C14—H14B	109.5
O1—C1—C6	118.9 (3)	H14A—C14—H14B	109.5
O1—C1—C2	123.9 (3)	N2—C14—H14C	109.5
C6—C1—C2	117.2 (3)	H14A—C14—H14C	109.5
C3—C2—C1	119.5 (3)	H14B—C14—H14C	109.5
C3—C2—C7	116.9 (3)	N2—C15—H15A	109.5
C1—C2—C7	123.6 (3)	N2—C15—H15B	109.5
C4—C3—C2	122.3 (3)	H15A—C15—H15B	109.5
C4—C3—H3	118.9	N2—C15—H15C	109.5
C2—C3—H3	118.9	H15A—C15—H15C	109.5
C3—C4—C5	118.4 (3)	H15B—C15—H15C	109.5

O5ⁱ—Zn2—O1—C1	176.2 (3)	C6—C1—C2—C3	−0.6 (5)
O3ⁱⁱ—Zn2—O1—C1	1.2 (3)	O1—C1—C2—C7	−1.7 (6)
O7ⁱⁱⁱ—Zn2—O1—C1	−90.2 (3)	C6—C1—C2—C7	176.7 (4)
O9—Zn2—O1—C1	83.2 (3)	C1—C2—C3—C4	0.7 (6)
O5ⁱ—Zn2—O1—Zn1	−0.87 (17)	C7—C2—C3—C4	−176.7 (4)
O3ⁱⁱ—Zn2—O1—Zn1	−175.84 (12)	C2—C3—C4—C5	0.0 (6)
O7ⁱⁱⁱ—Zn2—O1—Zn1	92.75 (14)	C2—C3—C4—C8	180.0 (4)
O9—Zn2—O1—Zn1	−93.80 (14)	C3—C4—C5—C6	−0.9 (6)
O4ⁱ—Zn1—O1—C1	162.9 (3)	C8—C4—C5—C6	179.2 (4)
O2—Zn1—O1—C1	31.5 (3)	C4—C5—C6—C1	1.0 (6)
O6—Zn1—O1—C1	−82.5 (3)	O1—C1—C6—C5	178.2 (4)
O8—Zn1—O1—C1	63.1 (15)	C2—C1—C6—C5	−0.3 (6)
O4ⁱ—Zn1—O1—Zn2	−20.14 (16)	Zn2^iv—O3—C7—O2	−22.4 (5)
O2—Zn1—O1—Zn2	−151.52 (15)	Zn2^iv—O3—C7—C2	156.6 (3)
O6—Zn1—O1—Zn2	94.47 (16)	Zn1—O2—C7—O3	−165.0 (3)
O8—Zn1—O1—Zn2	−120.0 (14)	Zn1—O2—C7—C2	16.1 (5)
O4ⁱ—Zn1—O2—C7	−125.3 (3)	C3—C2—C7—O3	5.2 (5)
O6—Zn1—O2—C7	59.7 (4)	C1—C2—C7—O3	−172.1 (4)
O1—Zn1—O2—C7	−29.2 (3)	C3—C2—C7—O2	−175.8 (4)
O8—Zn1—O2—C7	153.1 (3)	C1—C2—C7—O2	6.9 (6)
O4ⁱ—Zn1—O6—C9	−99.1 (4)	Zn1^v—O4—C8—O5	−36.5 (6)
O2—Zn1—O6—C9	76.7 (4)	Zn1^v—O4—C8—C4	142.9 (3)
O1—Zn1—O6—C9	163.8 (4)	Zn2^v—O5—C8—O4	−9.7 (6)
O8—Zn1—O6—C9	−13.7 (4)	Zn2^v—O5—C8—C4	170.9 (3)
O4ⁱ—Zn1—O8—C10	−149.8 (4)	C3—C4—C8—O4	1.8 (6)
O2—Zn1—O8—C10	−18.0 (3)	C5—C4—C8—O4	−178.2 (4)
O6—Zn1—O8—C10	96.0 (4)	C3—C4—C8—O5	−178.7 (4)
O1—Zn1—O8—C10	−49.5 (16)	C5—C4—C8—O5	1.3 (6)
O5ⁱ—Zn2—O9—C13	−83.7 (4)	Zn2^vi—O7—C9—O6	173.7 (3)
O1—Zn2—O9—C13	22.1 (4)	Zn1—O6—C9—O7	−172.2 (3)
O3ⁱⁱ—Zn2—O9—C13	144.4 (4)	Zn1—O8—C10—N1	−178.9 (3)
O7ⁱⁱⁱ—Zn2—O9—C13	157.6 (7)	C11—N1—C10—O8	−2.0 (7)
Zn2—O1—C1—C6	−18.0 (5)	C12—N1—C10—O8	179.9 (4)
Zn1—O1—C1—C6	158.8 (3)	Zn2—O9—C13—N2	−164.4 (3)
Zn2—O1—C1—C2	160.4 (3)	C14—N2—C13—O9	1.1 (7)
Zn1—O1—C1—C2	−22.9 (5)	C15—N2—C13—O9	−178.8 (5)
O1—C1—C2—C3	−179.0 (3)

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

Experimental details

Crystal data
Chemical formula	[Zn₂(CHO₂)(C₈H₃O₅)(C₃H₇NO)₂]
M_r	501.05
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.1190 (4), 14.7355 (6), 14.4711 (6)
β (°)	107.752 (1)
V (Å³)	1851.94 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.64
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.551, 0.768
No. of measured, independent and observed [I > 2σ(I)] reflections	9831, 3343, 2881
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.097, 1.18
No. of reflections	3343
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.99

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and MS Modeling (Accelrys, 2005).

Selected bond lengths (Å) top

Zn1—O4ⁱ	1.960 (3)	Zn2—O5ⁱ	1.978 (3)
Zn1—O2	1.972 (3)	Zn2—O1	2.029 (3)
Zn1—O6	1.977 (3)	Zn2—O3ⁱⁱ	2.038 (3)
Zn1—O1	2.083 (2)	Zn2—O7ⁱⁱⁱ	2.075 (3)
Zn1—O8	2.127 (3)	Zn2—O9	2.114 (3)

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

Acknowledgements

We acknowledge financial support provided by the Korea Research Foundation (grant No. KRF–2006–351–C00016).

References

Accelrys (2005). MS Modeling. Accelrys Inc., San Diego, CA, USA. Google Scholar
Bruker (1997). SMART 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
Zhang, X., Chen, J., Xu, K., Ding, C., She, W. & Chen, X. (2004). Inorg. Chim. Acta, 357, 1389–1396. Web of Science CSD CrossRef CAS Google Scholar

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