catena-Poly[[bis­(1-methyl-1H-imidazole-κN3)zinc]-μ-3-nitro­phthalato-κ2O1:O2]

Zhang, X.-J.; Guo, M.-L.

doi:10.1107/S1600536812004576

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m262-m263

doi:10.1107/S1600536812004576

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catena-Poly[[bis(1-methyl-1H-imidazole-κN³)zinc]-μ-3-nitrophthalato-κ²O¹:O²]

Xi-Juan Zhang ^a and Ming-Lin Guo ^b ^*

^aSchool of Materials and Key Laboratory of Hollow Fiber Membrane Materials and Membrane Process, Tianjin Polytechnic University, Tianjin 300387, People's Republic of China, and ^bSchool of Environment and Chemical Engineering, and Key Laboratory of Hollow Fiber Membrane Materials and Membrane Process, Tianjin Polytechnic University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: guomlin@yahoo.com

(Received 8 January 2012; accepted 2 February 2012; online 10 February 2012)

In the title complex, [Zn(C₈H₃NO₆)(C₄H₆N₂)₂]_n, the carboxylate groups of the 3-nitrophthalate dianion ligand coordinate the Zn^II ion in a bis-monodentate mode. The Zn^II ion shows distorted tetrahedral coordination as it is bonded to two O atoms from the carboxylate groups of symmetry-related 3-nitrophthalate anions and two N atoms of two independent 1-methylimidazole molecules. The bridging 3-nitrophthalate ligand allows the formation of one-dimensional chains in the c direction. The crystal structure is further stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related structures with methylimidazole, see: Baca et al. (2003 , 2004 ); Zhao (2008 ). For related coordination modes of phthalate and substituted phthalate with metal, see: Biagini Cingi et al. (1978 ); Guo & Guo (2007 ); Ma et al. (2004 ); Wang et al. (2009 ); Yang et al. (2003 ).

Experimental

Crystal data

[Zn(C₈H₃NO₆)(C₄H₆N₂)₂]
M_r = 438.70
Monoclinic, P 2₁ /c
a = 8.375 (2) Å
b = 16.005 (4) Å
c = 14.057 (4) Å
β = 102.618 (4)°
V = 1838.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 294 K
0.18 × 0.06 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.883, T_max = 0.921
13428 measured reflections
3240 independent reflections
2904 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.06
3240 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond angles (°)

O2—Zn1—O3ⁱ	105.60 (6)
O2—Zn1—N3	123.39 (7)
O3ⁱ—Zn1—N3	110.17 (7)
O2—Zn1—N1	104.66 (6)
O3ⁱ—Zn1—N1	103.44 (7)
N3—Zn1—N1	107.78 (7)
O1—C1—O2	126.52 (18)
O4—C8—O3	125.73 (19)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O4	0.93	2.25	3.156 (3)	166
C11—H11⋯O1ⁱⁱ	0.93	2.53	3.297 (3)	140
C12—H12A⋯O5ⁱⁱⁱ	0.96	2.44	3.078 (3)	124
C13—H13⋯O1ⁱ	0.93	2.46	3.373 (3)	169
C16—H16B⋯O2^iv	0.96	2.44	3.345 (3)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536812004576/bh2410sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004576/bh2410Isup2.hkl

checkCIF report

Comment top

Aromatic dicarboxylate ligands such as phthalate (phth) and substituted phthalate have been used in architecture of polymeric metal complexes because they can act as a bis-monodentate, bis-bidentate and combined modes of coordination to form short bridges via one carboxylato end, or long bridges via the benzene ring, leading to a great variety of structures (Zhao, 2008; Biagini Cingi et al., 1978; Guo & Guo, 2007; Wang et al., 2009; Ma et al., 2004; Baca et al., 2003, 2004; Yang et al., 2003). We have used the 3-nitrophthalate dianion as a ligand, and have obtained the title novel four-coordinate 3-nitrophthalate-zinc complex. We describe here the structure of this one-dimensional metal-nitrophthalate coordination polymer with bis-monodentate coordination mode.

The asymmetric unit in the structure of the title compound comprises one Zn atom, one complete 3-nitrophthalate dianion and two non-equivalent 1-methylimidazole molecules, and is shown in Fig. 1 in a symmetry-expanded view, which displays the full coordination sphere of the Zn atom. Selected geometric parameters are given in Table 1.

The Zn atom exhibits a distorted tetrahedral environment with atoms O2, O3ⁱ (see Fig. 1 for symmetry codes) of two non-equivalent 3-nitrophthalate dianions and N1 and N3 atoms of coordinated 1-methylimidazole molecules (see Table 1 for bond lengths and angles), and this results in forming one-dimensional chains along the c direction. These are further aggregated into a three-dimensional framework via weak C—H···O interactions (see Table 2). A packing diagram is shown in Fig. 2.

Related literature top

For related structures with methylimidazole, see: Baca et al. (2003, 2004); Zhao (2008). For related coordination modes of phthalate and substituted phthalate with metal, see: Biagini Cingi et al. (1978); Guo & Guo (2007); Ma et al. (2004); Wang et al. (2009); Yang et al. (2003).

Experimental top

Zinc oxide (0.21 g, 2.5 mmol) was added to a stirred solution of 3-nitrophthalic acid (0.53 g, 2.5 mmol) in boiling water (20.0 ml) over a period of 40 min, then drip 1-methylimidazole (0.33 g, 4 mmol) in the solution. After filtration, slow evaporation over a period of one week at room temperature provided colorless needle of the title complex.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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. A view of the structure of the title complex, showing the coordination environment for Zn atom; displacement ellipsoids are drawn at the 30% probability level [Symmetry code: (i) x, -y+1/2, z+1/2].
	Fig. 2. The packing diagram of the complex, viewed down the b axis, showing its one dimensional chain structure along the c direction.

catena-Poly[[bis(1-methyl-1Himidazole-κN³)zinc]- µ-3-nitrophthalato-κ²O¹:O²] top

Crystal data top

[Zn(C₈H₃NO₆)(C₄H₆N₂)₂]	F(000) = 896
M_r = 438.70	D_x = 1.585 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6551 reflections
a = 8.375 (2) Å	θ = 1.5–27.9°
b = 16.005 (4) Å	µ = 1.38 mm⁻¹
c = 14.057 (4) Å	T = 294 K
β = 102.618 (4)°	Needle, colorless
V = 1838.7 (8) Å³	0.18 × 0.06 × 0.06 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3240 independent reflections
Radiation source: rotating anode	2904 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.027
Detector resolution: 28.57 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −19→18
T_min = 0.883, T_max = 0.921	l = −16→16
13428 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0448P)² + 0.3182P] where P = (F_o² + 2F_c²)/3
3240 reflections	(Δ/σ)_max = 0.009
255 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³
0 constraints

Crystal data top

[Zn(C₈H₃NO₆)(C₄H₆N₂)₂]	V = 1838.7 (8) Å³
M_r = 438.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.375 (2) Å	µ = 1.38 mm⁻¹
b = 16.005 (4) Å	T = 294 K
c = 14.057 (4) Å	0.18 × 0.06 × 0.06 mm
β = 102.618 (4)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3240 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2904 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.921	R_int = 0.027
13428 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.06	Δρ_max = 0.43 e Å⁻³
3240 reflections	Δρ_min = −0.37 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.37841 (3)	0.207619 (14)	0.455381 (16)	0.01901 (10)
O1	0.40470 (16)	0.33302 (8)	0.29849 (10)	0.0208 (3)
O2	0.21557 (17)	0.27506 (9)	0.36867 (10)	0.0232 (3)
O3	0.25521 (18)	0.36236 (9)	0.02871 (10)	0.0240 (3)
O4	0.21554 (18)	0.24772 (9)	0.11179 (10)	0.0247 (3)
O5	0.1941 (2)	0.44350 (11)	0.44209 (11)	0.0380 (4)
O6	−0.0626 (2)	0.41913 (11)	0.43565 (12)	0.0429 (4)
N1	0.4567 (2)	0.12574 (10)	0.36701 (12)	0.0205 (4)
N2	0.4793 (2)	0.05951 (11)	0.23352 (12)	0.0242 (4)
N3	0.5739 (2)	0.25540 (11)	0.54444 (12)	0.0230 (4)
N4	0.7568 (2)	0.28401 (11)	0.67687 (13)	0.0282 (4)
N5	0.0545 (2)	0.42875 (11)	0.39749 (13)	0.0289 (4)
C1	0.2635 (2)	0.32439 (12)	0.30897 (13)	0.0178 (4)
C2	0.1264 (2)	0.37573 (12)	0.24794 (14)	0.0180 (4)
C3	0.0247 (3)	0.42461 (13)	0.29116 (15)	0.0246 (5)
C4	−0.0997 (3)	0.47334 (15)	0.23928 (17)	0.0353 (6)
H4	−0.1657	0.5046	0.2712	0.042*
C5	−0.1245 (3)	0.47481 (16)	0.13908 (17)	0.0392 (6)
H5	−0.2058	0.5085	0.1026	0.047*
C6	−0.0277 (3)	0.42597 (14)	0.09312 (16)	0.0320 (5)
H6	−0.0457	0.4265	0.0255	0.038*
C7	0.0960 (2)	0.37607 (12)	0.14624 (14)	0.0205 (4)
C8	0.1969 (2)	0.32282 (13)	0.09277 (14)	0.0208 (4)
C9	0.4173 (2)	0.12626 (12)	0.27040 (15)	0.0217 (5)
H9	0.3547	0.1675	0.2331	0.026*
C10	0.5501 (3)	0.05407 (14)	0.39165 (16)	0.0283 (5)
H10	0.5967	0.0371	0.4549	0.034*
C11	0.5631 (3)	0.01286 (14)	0.31019 (16)	0.0302 (5)
H11	0.6178	−0.0372	0.3066	0.036*
C12	0.4611 (3)	0.03974 (15)	0.13012 (16)	0.0350 (6)
H12A	0.3992	0.0830	0.0914	0.053*
H12B	0.4050	−0.0126	0.1161	0.053*
H12C	0.5673	0.0358	0.1150	0.053*
C13	0.6139 (3)	0.24697 (13)	0.64004 (15)	0.0244 (5)
H13	0.5510	0.2190	0.6768	0.029*
C14	0.6993 (3)	0.30033 (14)	0.51958 (17)	0.0305 (5)
H14	0.7046	0.3160	0.4566	0.037*
C15	0.8124 (3)	0.31792 (15)	0.60038 (17)	0.0344 (6)
H15	0.9094	0.3473	0.6039	0.041*
C16	0.8332 (3)	0.29180 (16)	0.78106 (17)	0.0407 (6)
H16A	0.8170	0.3474	0.8027	0.061*
H16B	0.9483	0.2807	0.7910	0.061*
H16C	0.7842	0.2524	0.8176	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02000 (15)	0.01878 (15)	0.01866 (14)	−0.00048 (9)	0.00515 (10)	0.00074 (9)
O1	0.0161 (8)	0.0221 (8)	0.0249 (7)	0.0007 (6)	0.0061 (6)	0.0011 (6)
O2	0.0216 (8)	0.0265 (8)	0.0231 (7)	0.0019 (6)	0.0087 (6)	0.0072 (6)
O3	0.0287 (8)	0.0241 (8)	0.0211 (7)	0.0016 (6)	0.0099 (6)	−0.0014 (6)
O4	0.0267 (9)	0.0216 (8)	0.0249 (8)	0.0037 (6)	0.0036 (6)	−0.0006 (6)
O5	0.0327 (10)	0.0483 (11)	0.0323 (9)	0.0025 (8)	0.0058 (7)	−0.0094 (8)
O6	0.0411 (11)	0.0552 (11)	0.0412 (10)	0.0013 (9)	0.0285 (8)	−0.0008 (9)
N1	0.0228 (10)	0.0190 (9)	0.0207 (9)	0.0013 (7)	0.0068 (7)	0.0010 (7)
N2	0.0248 (10)	0.0224 (9)	0.0269 (9)	−0.0005 (8)	0.0086 (8)	−0.0023 (8)
N3	0.0197 (9)	0.0255 (10)	0.0245 (9)	−0.0002 (7)	0.0066 (7)	−0.0014 (8)
N4	0.0187 (10)	0.0357 (11)	0.0295 (10)	0.0015 (8)	0.0036 (8)	−0.0062 (8)
N5	0.0340 (12)	0.0273 (10)	0.0289 (10)	0.0058 (8)	0.0146 (9)	−0.0006 (8)
C1	0.0217 (11)	0.0157 (10)	0.0163 (10)	−0.0006 (8)	0.0047 (8)	−0.0030 (8)
C2	0.0163 (10)	0.0169 (10)	0.0220 (10)	−0.0001 (8)	0.0066 (8)	0.0023 (8)
C3	0.0248 (12)	0.0261 (12)	0.0251 (11)	0.0029 (9)	0.0106 (9)	0.0013 (9)
C4	0.0301 (14)	0.0393 (14)	0.0395 (14)	0.0162 (11)	0.0142 (11)	0.0017 (11)
C5	0.0300 (14)	0.0484 (16)	0.0380 (14)	0.0215 (11)	0.0047 (11)	0.0079 (12)
C6	0.0279 (13)	0.0407 (14)	0.0257 (12)	0.0086 (10)	0.0027 (9)	0.0041 (10)
C7	0.0166 (11)	0.0221 (11)	0.0232 (10)	0.0011 (8)	0.0052 (8)	0.0009 (9)
C8	0.0165 (11)	0.0261 (12)	0.0175 (10)	0.0002 (9)	−0.0013 (8)	−0.0027 (9)
C9	0.0187 (11)	0.0176 (11)	0.0292 (11)	−0.0002 (8)	0.0058 (8)	0.0011 (9)
C10	0.0273 (13)	0.0291 (12)	0.0285 (11)	0.0057 (10)	0.0059 (9)	0.0088 (10)
C11	0.0305 (13)	0.0240 (12)	0.0375 (13)	0.0091 (10)	0.0104 (10)	0.0043 (10)
C12	0.0433 (15)	0.0348 (13)	0.0287 (12)	−0.0035 (11)	0.0115 (11)	−0.0080 (11)
C13	0.0206 (11)	0.0263 (12)	0.0269 (11)	0.0016 (9)	0.0066 (9)	−0.0010 (9)
C14	0.0286 (13)	0.0348 (13)	0.0313 (13)	−0.0064 (10)	0.0134 (10)	−0.0026 (10)
C15	0.0237 (13)	0.0396 (14)	0.0425 (14)	−0.0095 (10)	0.0129 (10)	−0.0082 (12)
C16	0.0277 (14)	0.0570 (17)	0.0324 (14)	0.0029 (11)	−0.0047 (10)	−0.0035 (12)

Geometric parameters (Å, º) top

Zn1—O2	1.9454 (14)	C2—C7	1.396 (3)
Zn1—O3ⁱ	1.9612 (14)	C3—C4	1.376 (3)
Zn1—N3	1.9841 (17)	C4—C5	1.378 (3)
Zn1—N1	2.0116 (17)	C4—H4	0.9300
O1—C1	1.231 (2)	C5—C6	1.383 (3)
O2—C1	1.279 (2)	C5—H5	0.9300
O3—C8	1.281 (2)	C6—C7	1.389 (3)
O4—C8	1.234 (2)	C6—H6	0.9300
O5—N5	1.223 (2)	C7—C8	1.511 (3)
O6—N5	1.226 (2)	C9—H9	0.9300
N1—C9	1.326 (3)	C10—C11	1.346 (3)
N1—C10	1.389 (3)	C10—H10	0.9300
N2—C9	1.341 (3)	C11—H11	0.9300
N2—C11	1.371 (3)	C12—H12A	0.9600
N2—C12	1.463 (3)	C12—H12B	0.9600
N3—C13	1.319 (3)	C12—H12C	0.9600
N3—C14	1.380 (3)	C13—H13	0.9300
N4—C13	1.335 (3)	C14—C15	1.340 (3)
N4—C15	1.373 (3)	C14—H14	0.9300
N4—C16	1.470 (3)	C15—H15	0.9300
N5—C3	1.462 (3)	C16—H16A	0.9600
C1—C2	1.516 (3)	C16—H16B	0.9600
C2—C3	1.390 (3)	C16—H16C	0.9600

O2—Zn1—O3ⁱ	105.60 (6)	C5—C6—H6	119.4
O2—Zn1—N3	123.39 (7)	C7—C6—H6	119.4
O3ⁱ—Zn1—N3	110.17 (7)	C6—C7—C2	120.04 (19)
O2—Zn1—N1	104.66 (6)	C6—C7—C8	119.29 (18)
O3ⁱ—Zn1—N1	103.44 (7)	C2—C7—C8	120.67 (17)
N3—Zn1—N1	107.78 (7)	O4—C8—O3	125.73 (19)
C1—O2—Zn1	118.44 (13)	O4—C8—C7	119.97 (18)
C8—O3—Zn1ⁱⁱ	114.34 (13)	O3—C8—C7	114.30 (17)
C9—N1—C10	105.16 (17)	N1—C9—N2	111.11 (18)
C9—N1—Zn1	125.92 (14)	N1—C9—H9	124.4
C10—N1—Zn1	128.74 (14)	N2—C9—H9	124.4
C9—N2—C11	107.74 (17)	C11—C10—N1	109.76 (19)
C9—N2—C12	126.27 (18)	C11—C10—H10	125.1
C11—N2—C12	125.99 (19)	N1—C10—H10	125.1
C13—N3—C14	105.86 (18)	C10—C11—N2	106.23 (19)
C13—N3—Zn1	126.48 (15)	C10—C11—H11	126.9
C14—N3—Zn1	127.59 (15)	N2—C11—H11	126.9
C13—N4—C15	107.49 (19)	N2—C12—H12A	109.5
C13—N4—C16	125.6 (2)	N2—C12—H12B	109.5
C15—N4—C16	126.8 (2)	H12A—C12—H12B	109.5
O5—N5—O6	124.51 (19)	N2—C12—H12C	109.5
O5—N5—C3	117.59 (18)	H12A—C12—H12C	109.5
O6—N5—C3	117.88 (19)	H12B—C12—H12C	109.5
O1—C1—O2	126.52 (18)	N3—C13—N4	110.9 (2)
O1—C1—C2	119.99 (17)	N3—C13—H13	124.6
O2—C1—C2	113.49 (17)	N4—C13—H13	124.6
C3—C2—C7	116.93 (18)	C15—C14—N3	109.3 (2)
C3—C2—C1	121.21 (17)	C15—C14—H14	125.3
C7—C2—C1	121.86 (17)	N3—C14—H14	125.3
C4—C3—C2	123.5 (2)	C14—C15—N4	106.4 (2)
C4—C3—N5	117.16 (19)	C14—C15—H15	126.8
C2—C3—N5	119.23 (18)	N4—C15—H15	126.8
C3—C4—C5	118.6 (2)	N4—C16—H16A	109.5
C3—C4—H4	120.7	N4—C16—H16B	109.5
C5—C4—H4	120.7	H16A—C16—H16B	109.5
C4—C5—C6	119.7 (2)	N4—C16—H16C	109.5
C4—C5—H5	120.2	H16A—C16—H16C	109.5
C6—C5—H5	120.2	H16B—C16—H16C	109.5
C5—C6—C7	121.2 (2)

O3ⁱ—Zn1—O2—C1	−177.09 (13)	C4—C5—C6—C7	−0.9 (4)
N3—Zn1—O2—C1	55.12 (16)	C5—C6—C7—C2	−1.2 (3)
N1—Zn1—O2—C1	−68.28 (15)	C5—C6—C7—C8	179.1 (2)
O2—Zn1—N1—C9	7.11 (18)	C3—C2—C7—C6	2.2 (3)
O3ⁱ—Zn1—N1—C9	117.49 (17)	C1—C2—C7—C6	−178.04 (19)
N3—Zn1—N1—C9	−125.83 (17)	C3—C2—C7—C8	−178.14 (18)
O2—Zn1—N1—C10	−167.15 (17)	C1—C2—C7—C8	1.7 (3)
O3ⁱ—Zn1—N1—C10	−56.76 (19)	Zn1ⁱⁱ—O3—C8—O4	1.6 (3)
N3—Zn1—N1—C10	59.91 (19)	Zn1ⁱⁱ—O3—C8—C7	−177.52 (12)
O2—Zn1—N3—C13	121.96 (17)	C6—C7—C8—O4	−129.1 (2)
O3ⁱ—Zn1—N3—C13	−3.9 (2)	C2—C7—C8—O4	51.2 (3)
N1—Zn1—N3—C13	−116.05 (18)	C6—C7—C8—O3	50.1 (3)
O2—Zn1—N3—C14	−61.5 (2)	C2—C7—C8—O3	−129.6 (2)
O3ⁱ—Zn1—N3—C14	172.64 (17)	C10—N1—C9—N2	0.3 (2)
N1—Zn1—N3—C14	60.4 (2)	Zn1—N1—C9—N2	−175.08 (13)
Zn1—O2—C1—O1	1.6 (3)	C11—N2—C9—N1	0.3 (2)
Zn1—O2—C1—C2	−177.94 (12)	C12—N2—C9—N1	−179.79 (19)
O1—C1—C2—C3	−125.2 (2)	C9—N1—C10—C11	−0.7 (2)
O2—C1—C2—C3	54.5 (2)	Zn1—N1—C10—C11	174.44 (15)
O1—C1—C2—C7	55.0 (3)	N1—C10—C11—N2	0.9 (3)
O2—C1—C2—C7	−125.3 (2)	C9—N2—C11—C10	−0.7 (2)
C7—C2—C3—C4	−1.3 (3)	C12—N2—C11—C10	179.3 (2)
C1—C2—C3—C4	178.9 (2)	C14—N3—C13—N4	0.1 (2)
C7—C2—C3—N5	−178.00 (18)	Zn1—N3—C13—N4	177.23 (14)
C1—C2—C3—N5	2.2 (3)	C15—N4—C13—N3	−0.3 (2)
O5—N5—C3—C4	−127.4 (2)	C16—N4—C13—N3	175.7 (2)
O6—N5—C3—C4	50.9 (3)	C13—N3—C14—C15	0.1 (3)
O5—N5—C3—C2	49.5 (3)	Zn1—N3—C14—C15	−176.93 (16)
O6—N5—C3—C2	−132.1 (2)	N3—C14—C15—N4	−0.3 (3)
C2—C3—C4—C5	−0.7 (4)	C13—N4—C15—C14	0.4 (3)
N5—C3—C4—C5	176.1 (2)	C16—N4—C15—C14	−175.5 (2)
C3—C4—C5—C6	1.8 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4	0.93	2.25	3.156 (3)	166
C11—H11···O1ⁱⁱⁱ	0.93	2.53	3.297 (3)	140
C12—H12A···O5ⁱⁱ	0.96	2.44	3.078 (3)	124
C13—H13···O1ⁱ	0.93	2.46	3.373 (3)	169
C16—H16B···O2^iv	0.96	2.44	3.345 (3)	158

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₃NO₆)(C₄H₆N₂)₂]
M_r	438.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	8.375 (2), 16.005 (4), 14.057 (4)
β (°)	102.618 (4)
V (Å³)	1838.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.18 × 0.06 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.883, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	13428, 3240, 2904
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.06
No. of reflections	3240
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.37

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top

O2—Zn1—O3ⁱ	105.60 (6)	O3ⁱ—Zn1—N1	103.44 (7)
O2—Zn1—N3	123.39 (7)	N3—Zn1—N1	107.78 (7)
O3ⁱ—Zn1—N3	110.17 (7)	O1—C1—O2	126.52 (18)
O2—Zn1—N1	104.66 (6)	O4—C8—O3	125.73 (19)

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4	0.93	2.25	3.156 (3)	165.6
C11—H11···O1ⁱⁱ	0.93	2.53	3.297 (3)	139.8
C12—H12A···O5ⁱⁱⁱ	0.96	2.44	3.078 (3)	123.6
C13—H13···O1ⁱ	0.93	2.46	3.373 (3)	168.5
C16—H16B···O2^iv	0.96	2.44	3.345 (3)	158.2

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

Acknowledgements

The authors thank Tianjin Polytechnic University for financial support.

References

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