Poly[[[μ2-1,1′-(butane-1,4-di­yl)bis­(1H-imidazole)-κ2N3:N3′](μ2-2,6-di­methyl­pyridine-3,5-dicarboxyl­ato-κ2O3:O5)zinc] dihydrate]

Yue, Y.-M.; Qian, L.; Zhu, Z.-H.; Wang, C.; Gao, T.

doi:10.1107/S1600536811039481

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1471-m1472

https://doi.org/10.1107/S1600536811039481

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Poly[[[μ₂-1,1′-(butane-1,4-diyl)bis(1H-imidazole)-κ²N³:N^3′](μ₂-2,6-dimethylpyridine-3,5-dicarboxylato-κ²O³:O⁵)zinc] dihydrate]

Yu-Mei Yue,^a ^* Lei Qian,^b Zheng-Hao Zhu,^c Cheng Wang ^d and Ting Gao ^d

^aPesticide Engineering Research Center of Heilongjiang Province, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDaqing Oil Field Water Supply Company, Institute of Source of Water Researching, Daqing 163458, People's Republic of China, ^cDepartment of Service, Dionex China Ltd, Beijing 100029, People's Republic of China, and ^dSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: yueyumei@yahoo.com.cn

(Received 15 July 2011; accepted 26 September 2011; online 30 September 2011)

In the title coordination polymer, {[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O}_n, the Zn^II ion displays a distorted tetrahedral geometry with two imidazole N atoms from two 1,1′-(butane-1,4-diyl)bis(imidazole) (bbi) ligands and two carboxylate O atoms from two 2,6-dimethylpyridine-3,5-dicarboxylate (dpdc) ligands. The bbi and dpdc ligands bridge the Zn^II ions, forming layers parallel to (011). O—H⋯O and O—H⋯N hydrogen bonds and π–π interactions between the imidazole rings [centroid–centroid distance = 3.807 (5) Å] connect the layers. Two of the three uncoordinated water molecules are disordered, each over two 0.25-occupancy positions.

Related literature

For transition metal complexes derived from 2,6-dimethylpyridine-3,5-dicarboxylic acid, see: Chen et al. (2009 ); Huang et al. (2008 ); Zhang et al. (2008a ); Zhou et al. (2009 ). For metal complexes derived from 1,1′-(butane-1,4-diyl)bis(imidazole) and carboxylic acids, see: Lan et al. (2008 ); Tian et al. (2009 ); Zhang et al. (2008b ).

Experimental

Crystal data

[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O
M_r = 484.82
Orthorhombic, P c a 2₁
a = 17.8088 (12) Å
b = 9.4003 (4) Å
c = 15.5798 (8) Å
V = 2608.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 K
0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.807, T_max = 0.823
14228 measured reflections
4717 independent reflections
3753 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.175
S = 1.03
4717 reflections
315 parameters
36 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.64 e Å⁻³
Absolute structure: Flack (1983 ), 2186 Friedel pairs
Flack parameter: 0.03 (2)

Table 1
Selected bond lengths (Å)

Zn1—O1	1.954 (4)
Zn1—O4ⁱ	1.965 (3)
Zn1—N2	1.994 (6)
Zn1—N4ⁱⁱ	2.032 (6)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+2, -y+2, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1B⋯O2ⁱⁱⁱ	0.87 (4)	1.99 (4)	2.820 (9)	160 (4)
O1W—H1A⋯N1	0.87 (3)	1.95 (3)	2.736 (10)	149 (5)
Symmetry code: (iii) $[x-{\script{1\over 2}}, -y+1, z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811039481/hy2452sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039481/hy2452Isup2.hkl

checkCIF report

Comment top

In recent years, great interest has been focused on the crystal engineering of coordination frameworks. As is already known, pyridine-3,5-dicarboxylic acid is a rigid and linear ligand that possesses the capability to bridge metal atoms in various coordination modes through the carboxylate O atoms and the pyridine N atom (Chen et al., 2009; Huang et al., 2008; Zhang et al., 2008a; Zhou et al., 2009). Flexible 1,1'-(butane-1,4-diyl)bis(imidazole) (bbi) ligand with organic carboxylic acids can build diverse topological architectures (Lan et al., 2008; Tian et al., 2009; Zhang et al., 2008b). Herein, we report the crystal structure of the title compound obtained by reacting bbi and 2,6-dimethylpyridine-3,5-dicarboxylic acid (H₂dpdc) with Zn(NO₃)₂.

In the title compound (Fig. 1), the Zn^II ion has a distorted tetrahedral geometry with two imidazole N atoms from two different bbi ligands and two carboxylate O atoms from two different dpdc ligands (Table 1). The bbi and dpdc ligands bridge the Zn^II ions into a layer parallel to (0 1 1) (Fig. 2). O—H···O and O—H···N hydrogen bonds (Table 2) and π–π interactions between the imidazole rings [centroid–centroid distance = 3.807 (5) Å] connect the layers.

Related literature top

For transition metal complexes of 2,6-dimethylpyridine-3,5-dicarboxylic acid, see: Chen et al. (2009); Huang et al. (2008); Zhang et al. (2008a); Zhou et al. (2009). For metal complexes of 1,1'-(butane-1,4-diyl)bis(imidazole) and carboxylic acids, see: Lan et al. (2008); Tian et al. (2009); Zhang et al. (2008b).

Experimental top

The title complex was obtained by the reaction of zinc(II) nitrate (59.5 mg, 0.2 mmol) with bbi (37.6 mg, 0.2 mmol) and H₂dpdc (39.4 mg, 0.2 mmol) in DMF/ethanol/water (10/10/5 ml). The mixture was stirred for 1 h and the solution was placed at room temperature for solvent volatilization. Single crystals were obtained after several days. Analysis, calculated for C₁₉H₂₅N₅O₆Zn: C 47.96, H 5.08, N 14.72%; found: C 48.08, H 5.49, N 14.52%.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) x, 1+y, z; (ii) 2-x, 2-y, 0.5+z.]
	Fig. 2. The crystal packing of the title compound, showing the layer structure.

Poly[[[µ₂-1,1'-(butane-1,4-diyl)bis(1H-imidazole)- κ²N³:N^3'](µ₂-2,6-dimethylpyridine-3,5-dicarboxylato- κ²O³:O⁵)zinc] dihydrate] top

Crystal data top

[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O	D_x = 1.234 Mg m⁻³
M_r = 484.82	Melting point: not measured K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4717 reflections
a = 17.8088 (12) Å	θ = 2.3–25.5°
b = 9.4003 (4) Å	µ = 0.98 mm⁻¹
c = 15.5798 (8) Å	T = 293 K
V = 2608.2 (2) Å³	Block, colorless
Z = 4	0.22 × 0.21 × 0.20 mm
F(000) = 1008

Data collection top

Bruker SMART APEX CCD diffractometer	4717 independent reflections
Radiation source: fine-focus sealed tube	3753 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
φ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→21
T_min = 0.807, T_max = 0.823	k = −11→11
14228 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.1192P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.042
4717 reflections	Δρ_max = 0.67 e Å⁻³
315 parameters	Δρ_min = −0.64 e Å⁻³
36 restraints	Absolute structure: Flack (1983), 2186 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (2)

Crystal data top

[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O	V = 2608.2 (2) Å³
M_r = 484.82	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 17.8088 (12) Å	µ = 0.98 mm⁻¹
b = 9.4003 (4) Å	T = 293 K
c = 15.5798 (8) Å	0.22 × 0.21 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4717 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3753 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.823	R_int = 0.087
14228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.175	Δρ_max = 0.67 e Å⁻³
S = 1.03	Δρ_min = −0.64 e Å⁻³
4717 reflections	Absolute structure: Flack (1983), 2186 Friedel pairs
315 parameters	Absolute structure parameter: 0.03 (2)
36 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.73885 (3)	0.97189 (5)	0.87767 (6)	0.0381 (2)
O1	0.6630 (2)	0.8258 (4)	0.8567 (3)	0.0560 (12)
O2	0.7521 (2)	0.6656 (5)	0.8691 (6)	0.0684 (15)
O3	0.5991 (3)	0.1007 (5)	0.9535 (4)	0.0695 (14)
O4	0.6934 (2)	0.1619 (3)	0.8694 (3)	0.0467 (9)
C3	0.6499 (2)	0.4454 (4)	0.8818 (5)	0.0351 (10)
H3	0.7012	0.4269	0.8817	0.080*
N2	0.8088 (3)	0.9860 (6)	0.7781 (4)	0.0429 (13)
N3	0.8753 (3)	0.9276 (6)	0.6618 (4)	0.0522 (13)
N4	1.2098 (4)	1.0326 (6)	0.4941 (4)	0.0477 (15)
N5	1.1556 (4)	0.9499 (7)	0.6067 (3)	0.0527 (16)
C2	0.6262 (3)	0.5836 (5)	0.8704 (4)	0.0362 (10)
C1	0.5488 (2)	0.6115 (5)	0.8722 (4)	0.0362 (10)
N1	0.5019 (2)	0.4987 (4)	0.8838 (6)	0.0395 (10)
C5	0.5237 (3)	0.3608 (6)	0.8968 (3)	0.0381 (13)
C4	0.5999 (3)	0.3304 (5)	0.8935 (3)	0.0363 (13)
C6	0.6854 (3)	0.6980 (5)	0.8651 (4)	0.0383 (12)
C7	0.6308 (3)	0.1830 (5)	0.9067 (3)	0.0372 (12)
C8	0.5117 (3)	0.7510 (6)	0.8585 (5)	0.0523 (16)
H8A	0.5160	0.7777	0.7992	0.080*
H8B	0.5354	0.8218	0.8937	0.080*
H8C	0.4596	0.7439	0.8738	0.080*
C9	0.4619 (4)	0.2569 (7)	0.9113 (5)	0.0599 (18)
H9A	0.4456	0.2623	0.9700	0.080*
H9B	0.4796	0.1625	0.8993	0.080*
H9C	0.4206	0.2789	0.8740	0.080*
C10	0.8374 (4)	0.8823 (7)	0.7308 (4)	0.0470 (15)
H10	0.8318	0.7865	0.7444	0.080*
C11	0.8304 (5)	1.1069 (9)	0.7376 (5)	0.065 (2)
H11	0.8187	1.1980	0.7567	0.080*
C12	0.8718 (5)	1.0785 (10)	0.6648 (6)	0.073 (2)
H12	0.8927	1.1432	0.6264	0.080*
C13	0.9116 (4)	0.8468 (8)	0.5972 (4)	0.0553 (16)
H13A	0.8888	0.8685	0.5422	0.080*
H13B	0.9035	0.7465	0.6086	0.080*
C14	0.9961 (4)	0.8745 (8)	0.5913 (4)	0.0560 (16)
H14A	1.0183	0.8045	0.5532	0.080*
H14B	1.0041	0.9675	0.5659	0.080*
C15	1.0364 (4)	0.8687 (9)	0.6769 (4)	0.0663 (19)
H15A	1.0157	0.7917	0.7109	0.080*
H15B	1.0277	0.9569	0.7076	0.080*
C16	1.1211 (4)	0.8462 (11)	0.6664 (5)	0.080 (3)
H16A	1.1451	0.8545	0.7221	0.080*
H16B	1.1301	0.7507	0.6452	0.080*
C17	1.1862 (5)	0.9177 (9)	0.5306 (5)	0.060 (2)
H17	1.1900	0.8266	0.5077	0.080*
C18	1.1924 (4)	1.1407 (8)	0.5463 (4)	0.0531 (16)
H18	1.2017	1.2365	0.5358	0.080*
C19	1.1601 (4)	1.0882 (12)	0.6143 (5)	0.069 (2)
H19	1.1429	1.1408	0.6609	0.080*
O1W	0.3529 (5)	0.5563 (7)	0.9086 (4)	0.0930 (19)
O3W	0.7170 (19)	0.455 (3)	1.0985 (19)	0.094 (7)	0.25
O3W'	0.670 (3)	0.304 (5)	1.064 (3)	0.166 (14)	0.25
O2W'	0.9930 (11)	0.4765 (19)	1.0714 (12)	0.053 (4)	0.25
O2W	0.9724 (18)	0.538 (3)	1.1357 (19)	0.091 (7)	0.25
H1B	0.320 (2)	0.488 (4)	0.910 (3)	0.080*
H1A	0.3963 (11)	0.515 (6)	0.916 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0316 (3)	0.0328 (3)	0.0500 (3)	−0.0002 (2)	0.0009 (4)	0.0007 (5)
O1	0.044 (2)	0.0301 (18)	0.094 (4)	−0.0058 (15)	−0.003 (2)	0.003 (2)
O2	0.037 (2)	0.042 (2)	0.126 (5)	−0.0053 (15)	0.003 (3)	0.012 (4)
O3	0.070 (3)	0.048 (3)	0.091 (3)	0.011 (2)	0.024 (3)	0.023 (3)
O4	0.0391 (19)	0.0318 (16)	0.069 (2)	0.0063 (13)	0.002 (2)	0.005 (2)
C3	0.032 (2)	0.033 (2)	0.040 (2)	−0.0028 (17)	0.009 (3)	0.005 (3)
N2	0.034 (3)	0.045 (3)	0.050 (3)	0.003 (2)	−0.002 (2)	0.001 (2)
N3	0.029 (3)	0.062 (3)	0.066 (3)	0.002 (3)	0.004 (2)	0.012 (3)
N4	0.037 (3)	0.054 (3)	0.052 (3)	0.000 (2)	0.001 (2)	0.002 (3)
N5	0.046 (3)	0.072 (4)	0.041 (3)	0.002 (3)	0.002 (2)	0.008 (3)
C2	0.036 (2)	0.034 (2)	0.039 (3)	−0.0024 (19)	0.005 (3)	0.004 (3)
C1	0.031 (2)	0.037 (2)	0.041 (2)	0.0024 (18)	0.006 (3)	0.009 (3)
N1	0.035 (2)	0.036 (2)	0.047 (3)	−0.0004 (15)	−0.007 (3)	−0.004 (2)
C5	0.028 (2)	0.042 (3)	0.045 (4)	−0.008 (2)	−0.001 (2)	0.002 (2)
C4	0.035 (3)	0.028 (2)	0.046 (4)	0.0025 (19)	0.005 (2)	0.003 (2)
C6	0.038 (3)	0.030 (2)	0.048 (3)	−0.0060 (19)	0.004 (2)	−0.001 (2)
C7	0.040 (3)	0.030 (3)	0.042 (3)	−0.002 (2)	0.004 (2)	0.004 (2)
C8	0.039 (3)	0.038 (3)	0.080 (5)	0.003 (2)	−0.002 (3)	0.001 (3)
C9	0.040 (3)	0.047 (3)	0.092 (5)	−0.014 (3)	0.002 (3)	0.008 (3)
C10	0.040 (4)	0.046 (3)	0.055 (3)	−0.001 (3)	−0.004 (3)	0.008 (3)
C11	0.068 (5)	0.050 (4)	0.076 (5)	0.001 (4)	0.035 (4)	0.012 (4)
C12	0.076 (6)	0.063 (5)	0.081 (5)	−0.005 (5)	0.015 (4)	0.002 (4)
C13	0.048 (4)	0.071 (4)	0.047 (3)	0.000 (3)	0.007 (3)	−0.002 (3)
C14	0.040 (3)	0.078 (5)	0.050 (3)	0.004 (3)	0.009 (3)	0.010 (3)
C15	0.051 (4)	0.099 (6)	0.049 (4)	−0.002 (4)	0.004 (3)	0.014 (4)
C16	0.048 (4)	0.125 (8)	0.066 (4)	0.001 (4)	0.005 (3)	0.038 (5)
C17	0.056 (4)	0.062 (5)	0.063 (4)	0.022 (4)	0.006 (3)	0.007 (4)
C18	0.048 (4)	0.059 (4)	0.052 (3)	0.009 (3)	0.005 (3)	−0.013 (3)
C19	0.041 (4)	0.102 (7)	0.063 (5)	−0.002 (5)	0.008 (3)	−0.012 (4)
O1W	0.090 (2)	0.092 (2)	0.097 (2)	−0.0007 (10)	0.0000 (10)	−0.0017 (10)
O3W	0.094 (7)	0.094 (7)	0.093 (7)	0.0002 (10)	−0.0002 (10)	0.0003 (10)
O3W'	0.166 (14)	0.166 (14)	0.166 (14)	0.0000 (10)	0.0000 (10)	0.0001 (10)
O2W'	0.053 (4)	0.053 (4)	0.053 (4)	0.0006 (10)	0.0003 (10)	−0.0006 (10)
O2W	0.092 (7)	0.091 (7)	0.092 (7)	0.0001 (10)	0.0002 (10)	0.0001 (10)

Geometric parameters (Å, º) top

Zn1—O1	1.954 (4)	C4—C7	1.505 (7)
Zn1—O4ⁱ	1.965 (3)	C8—H8A	0.9600
Zn1—N2	1.994 (6)	C8—H8B	0.9600
Zn1—N4ⁱⁱ	2.032 (6)	C8—H8C	0.9600
O1—C6	1.272 (6)	C9—H9A	0.9600
O2—C6	1.228 (7)	C9—H9B	0.9600
O3—C7	1.204 (7)	C9—H9C	0.9600
O4—C7	1.273 (7)	C10—H10	0.9300
O4—Zn1ⁱⁱⁱ	1.965 (3)	C11—C12	1.380 (12)
C3—C2	1.377 (7)	C11—H11	0.9300
C3—C4	1.412 (6)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.530 (9)
N2—C10	1.324 (9)	C13—H13A	0.9700
N2—C11	1.355 (10)	C13—H13B	0.9700
N3—C10	1.339 (8)	C14—C15	1.515 (9)
N3—C13	1.418 (9)	C14—H14A	0.9700
N3—C12	1.420 (11)	C14—H14B	0.9700
N4—C17	1.291 (11)	C15—C16	1.533 (11)
N4—C18	1.337 (9)	C15—H15A	0.9700
N4—Zn1^iv	2.032 (6)	C15—H15B	0.9700
N5—C19	1.308 (12)	C16—H16A	0.9700
N5—C17	1.340 (9)	C16—H16B	0.9700
N5—C16	1.480 (9)	C17—H17	0.9300
C2—C1	1.403 (6)	C18—C19	1.303 (10)
C2—C6	1.509 (7)	C18—H18	0.9300
C1—N1	1.362 (6)	C19—H19	0.9300
C1—C8	1.484 (7)	O1W—H1B	0.870 (10)
N1—C5	1.368 (7)	O1W—H1A	0.871 (10)
C5—C4	1.388 (7)	O3W—O3W'	1.73 (6)
C5—C9	1.489 (8)	O2W'—O2W	1.21 (3)

O1—Zn1—O4ⁱ	110.09 (16)	C5—C9—H9B	109.5
O1—Zn1—N2	110.4 (2)	H9A—C9—H9B	109.5
O4ⁱ—Zn1—N2	98.4 (2)	C5—C9—H9C	109.5
O1—Zn1—N4ⁱⁱ	116.5 (2)	H9A—C9—H9C	109.5
O4ⁱ—Zn1—N4ⁱⁱ	105.2 (2)	H9B—C9—H9C	109.5
N2—Zn1—N4ⁱⁱ	114.5 (3)	N2—C10—N3	114.0 (6)
C6—O1—Zn1	115.4 (4)	N2—C10—H10	123.0
C7—O4—Zn1ⁱⁱⁱ	118.2 (3)	N3—C10—H10	123.0
C2—C3—C4	123.0 (4)	N2—C11—C12	111.8 (7)
C2—C3—H3	118.5	N2—C11—H11	124.1
C4—C3—H3	118.5	C12—C11—H11	124.1
C10—N2—C11	104.4 (6)	C11—C12—N3	104.1 (7)
C10—N2—Zn1	128.6 (5)	C11—C12—H12	128.0
C11—N2—Zn1	126.5 (5)	N3—C12—H12	128.0
C10—N3—C13	129.0 (6)	N3—C13—C14	113.7 (6)
C10—N3—C12	105.7 (5)	N3—C13—H13A	108.8
C13—N3—C12	125.3 (6)	C14—C13—H13A	108.8
C17—N4—C18	107.0 (7)	N3—C13—H13B	108.8
C17—N4—Zn1^iv	121.5 (5)	C14—C13—H13B	108.8
C18—N4—Zn1^iv	131.5 (5)	H13A—C13—H13B	107.7
C19—N5—C17	106.3 (6)	C15—C14—C13	114.0 (5)
C19—N5—C16	128.5 (6)	C15—C14—H14A	108.8
C17—N5—C16	125.2 (7)	C13—C14—H14A	108.8
C3—C2—C1	118.4 (4)	C15—C14—H14B	108.8
C3—C2—C6	117.7 (4)	C13—C14—H14B	108.8
C1—C2—C6	123.6 (4)	H14A—C14—H14B	107.7
N1—C1—C2	117.3 (4)	C14—C15—C16	112.2 (5)
N1—C1—C8	115.7 (4)	C14—C15—H15A	109.2
C2—C1—C8	126.9 (4)	C16—C15—H15A	109.2
C1—N1—C5	125.7 (4)	C14—C15—H15B	109.2
N1—C5—C4	117.8 (4)	C16—C15—H15B	109.2
N1—C5—C9	115.8 (5)	H15A—C15—H15B	107.9
C4—C5—C9	126.4 (5)	N5—C16—C15	112.6 (6)
C5—C4—C3	117.6 (4)	N5—C16—H16A	109.1
C5—C4—C7	122.8 (5)	C15—C16—H16A	109.1
C3—C4—C7	119.4 (4)	N5—C16—H16B	109.1
O2—C6—O1	122.9 (5)	C15—C16—H16B	109.1
O2—C6—C2	119.7 (4)	H16A—C16—H16B	107.8
O1—C6—C2	117.4 (5)	N4—C17—N5	109.5 (7)
O3—C7—O4	126.0 (5)	N4—C17—H17	125.3
O3—C7—C4	120.2 (5)	N5—C17—H17	125.3
O4—C7—C4	113.7 (4)	C19—C18—N4	108.0 (8)
C1—C8—H8A	109.5	C19—C18—H18	126.0
C1—C8—H8B	109.5	N4—C18—H18	126.0
H8A—C8—H8B	109.5	C18—C19—N5	109.2 (7)
C1—C8—H8C	109.5	C18—C19—H19	125.4
H8A—C8—H8C	109.5	N5—C19—H19	125.4
H8B—C8—H8C	109.5	H1B—O1W—H1A	105 (4)
C5—C9—H9A	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1B···O2^v	0.87 (4)	1.99 (4)	2.820 (9)	160 (4)
O1W—H1A···N1	0.87 (3)	1.95 (3)	2.736 (10)	149 (5)

Symmetry code: (v) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O
M_r	484.82
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	17.8088 (12), 9.4003 (4), 15.5798 (8)
V (Å³)	2608.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.22 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.807, 0.823
No. of measured, independent and observed [I > 2σ(I)] reflections	14228, 4717, 3753
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.175, 1.03
No. of reflections	4717
No. of parameters	315
No. of restraints	36
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.64
Absolute structure	Flack (1983), 2186 Friedel pairs
Absolute structure parameter	0.03 (2)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).

Selected bond lengths (Å) top

Zn1—O1	1.954 (4)	Zn1—N2	1.994 (6)
Zn1—O4ⁱ	1.965 (3)	Zn1—N4ⁱⁱ	2.032 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1B···O2ⁱⁱⁱ	0.87 (4)	1.99 (4)	2.820 (9)	160 (4)
O1W—H1A···N1	0.87 (3)	1.95 (3)	2.736 (10)	149 (5)

Symmetry code: (iii) x−1/2, −y+1, z.

Acknowledgements

The authors gratefully acknowledge financial support from the Education Department of Heilongjiang Province (grant Nos. 11551335, 11551334 and 11551339) and Heilongjiang University.

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