Diaqua­bis­(4-carb­oxy-2-propyl-1H-imidazole-5-carboxyl­ato-κ2N3,O4)zinc(II) N,N-dimethyl­formamide disolvate

Hao, C.-J.; Zhao, X.-J.

doi:10.1107/S1600536810022282

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m810

doi:10.1107/S1600536810022282

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Diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ²N³,O⁴)zinc(II) N,N-dimethylformamide disolvate

Cheng-Jun Hao ^a ^* and Xiao-Jun Zhao ^a

^aCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
^*Correspondence e-mail: haochengjun2008@163.com

(Received 5 May 2010; accepted 10 June 2010; online 16 June 2010)

In the crystal structure of the title compound, [Zn(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the Zn^II atom is coordinated by two N,O-bidentate 2-propyl-1H-imidazole-4,5-dicarboxylate anions and two water molecules in a distorted octahedral environment. The asymmetric unit consists of one Zn^II atom located on a center of inversion as well as one anion, one water molecule and one additional dimethylformamide molecule that occupy general positions. Between the carboxyl and the carboxylate group an intramolecular hydrogen bond is found in which the hydroxy H atom is disordered. Disorder is also found for the H atoms of one of the three methyl groups. In the crystal structure, additional intermolecular N—H⋯O and O—H⋯O hydrogen bonding is found.

Related literature

For imidazole-4,5-dicarboxylic complexes, see: Maji et al. (2005 ); Yang & Zhang (2006 ).

Experimental

Crystal data

[Zn(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r = 641.94
Triclinic, $[P \overline 1]$
a = 7.3619 (9) Å
b = 9.3194 (13) Å
c = 11.2301 (15) Å
α = 76.281 (1)°
β = 87.621 (2)°
γ = 68.888 (1)°
V = 697.44 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 298 K
0.43 × 0.28 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.685, T_max = 0.797
3640 measured reflections
2425 independent reflections
2205 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.06
2425 reflections
179 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H2O6⋯O4ⁱ	0.82	2.16	2.9594 (14)	167
O6—H1O6⋯O4ⁱⁱ	0.82	1.98	2.796	175
O3—H1O3⋯O2	0.82	1.67	2.478	169
O2—H1O2⋯O3	0.82	1.66	2.478	177
N2—H1N1⋯O5ⁱⁱⁱ	0.86	1.84	2.6789 (17)	166
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y+1, z; (iii) x+1, y-1, z.

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022282/nc2185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022282/nc2185Isup2.hkl

checkCIF report

Comment top

Imidazole-4,5-dicarboxylic acid (H₃Imda) can be deprotonated to generate three types of anions, namely Imda^3-, HImda^2- and H₂Imda^-and react with metal ions to form fascinating structures with different structures and useful properties (Maji et al., 2005; Yang & Zhang, 2006). We have therefore reacted the 2-propyl-1H -imidazole-4,5-dicarboxylic acid with Zn(NO₃)₂ under hydrothermal conditions to obtain a new Zn^II complex and its structure is reported here. As illustrated in figure 1, the title complex molecule is a discrete complex, consisting of one Zn^II ion, two mono-deprotonated 2-Propyl-1H-imidazole-4,5-dicarboxy anions and two water molecules. The Zn ^II atom resides on a crystallographic inversion centre and is trans-coordinated by two N,O-bidentate 2-Propyl-1H-imidazole-4,5-dicarboxylate anions [Zn—O = 2.2052 (14) Å and Zn—N = 2.0643 (15) Å] and two water molecules [Zn—O = 2.1612 (15) Å], within a slightly distorted octahedral environment, with adjacent cis angles of [78.59 (6) °-101.41 (6) °]. The carboxyl and carboxylate group are via an intramolecular hydrogen bond in which the H atom is disordered. (Table 1). The crystal structure contain additional dimethylfromamide molecules that are linked to the complexes via N—H···O hydrogen bonding (Fig. 2). The complexes are additionally connected by intermolecular O—H···O hydrogen bonding between the carboxyl O atoms and the water H atoms (Table 1 and Fig. 2).

Related literature top

For the excellent qualities of imidazole-4,5-dicarboxylic complexes, see: Maji et al. (2005); Yang & Zhang (2006).

Experimental top

A mixture of Zn(NO₃)₂ (0.2 mmol, 0.03 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid(0.5 mmol, 0.99 g) and 10 ml of C₃H₇NO was loaded in a 25 ml Telflon-lined stainless steel vessel and heated at 373k for 3 days. White crystals were obtained when the sample was cooled to room temperature slowly.

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids (H atoms are represented by arbitrary spheres). Disordered H atoms are shown with full and open bonds. Symmetry codes: (i) 1-x, 1-y, 1-z.
	Fig. 2. View of the three-dimensional network constructed by O—H···O and N—H···O hydrogen bonding interactions (the disordering is not shown for clarity and h<drogen bonding is shown as dashed lines)

Diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato- κ²N³,O⁴)zinc(II) N,N-dimethylformamide disolvate top

Crystal data top

[Zn(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO	Z = 1
M_r = 641.94	F(000) = 336
Triclinic, P1	D_x = 1.528 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3619 (9) Å	Cell parameters from 2051 reflections
b = 9.3194 (13) Å	θ = 2.5–23.9°
c = 11.2301 (15) Å	µ = 0.95 mm⁻¹
α = 76.281 (1)°	T = 298 K
β = 87.621 (2)°	Block, colorless
γ = 68.888 (1)°	0.43 × 0.28 × 0.25 mm
V = 697.44 (16) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2425 independent reflections
Radiation source: fine-focus sealed tube	2205 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.685, T_max = 0.797	k = −10→11
3640 measured reflections	l = −13→10

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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0389P)² + 0.2536P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2425 reflections	Δρ_max = 0.26 e Å⁻³
179 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.067 (4)

Crystal data top

[Zn(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO	γ = 68.888 (1)°
M_r = 641.94	V = 697.44 (16) Å³
Triclinic, P1	Z = 1
a = 7.3619 (9) Å	Mo Kα radiation
b = 9.3194 (13) Å	µ = 0.95 mm⁻¹
c = 11.2301 (15) Å	T = 298 K
α = 76.281 (1)°	0.43 × 0.28 × 0.25 mm
β = 87.621 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2425 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2205 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.797	R_int = 0.015
3640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	Δρ_max = 0.26 e Å⁻³
2425 reflections	Δρ_min = −0.33 e Å⁻³
179 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5000	0.5000	0.5000	0.02921 (14)
N1	0.6351 (2)	0.25671 (17)	0.54820 (14)	0.0248 (3)
N2	0.8023 (2)	0.00172 (18)	0.60587 (15)	0.0287 (4)
H1N1	0.8740	−0.0885	0.6506	0.034*
N3	0.1215 (3)	0.4911 (2)	0.86419 (18)	0.0419 (4)
O1	0.4380 (2)	0.43510 (15)	0.33379 (12)	0.0342 (3)
O2	0.49486 (10)	0.22669 (8)	0.25454 (6)	0.0384 (4)
H1O2	0.5591	0.1315	0.2727	0.058*	0.60
O3	0.68632 (10)	−0.06116 (8)	0.31714 (6)	0.0423 (4)
H1O3	0.6132	0.0311	0.2920	0.063*	0.40
O4	0.86310 (10)	−0.23869 (8)	0.47855 (6)	0.0412 (4)
O5	0.03879 (10)	0.74901 (8)	0.76828 (6)	0.0575 (5)
O6	0.77394 (10)	0.51222 (8)	0.43114 (6)	0.0381 (4)
H1O6	0.7938	0.5887	0.4435	0.057*
H2O6	0.8631	0.4310	0.4647	0.057*
C1	0.5133 (3)	0.2910 (2)	0.34026 (17)	0.0275 (4)
C2	0.6268 (3)	0.1875 (2)	0.45418 (17)	0.0240 (4)
C3	0.7305 (3)	0.0277 (2)	0.48902 (17)	0.0251 (4)
C4	0.7647 (3)	−0.1017 (2)	0.42490 (19)	0.0306 (4)
C5	0.7424 (3)	0.1403 (2)	0.63940 (17)	0.0272 (4)
C6	0.7850 (3)	0.1559 (2)	0.76285 (18)	0.0357 (5)
H6C	0.7435	0.2675	0.7620	0.043*
H6D	0.9247	0.1093	0.7807	0.043*
C7	0.6844 (4)	0.0768 (3)	0.8641 (2)	0.0553 (7)
H7A	0.5456	0.1187	0.8432	0.066*
H7B	0.7320	−0.0358	0.8679	0.066*
C8	0.7156 (4)	0.0996 (3)	0.9888 (2)	0.0571 (7)
H8B	0.7054	0.2071	0.9815	0.086*	0.60
H8C	0.8429	0.0289	1.0226	0.086*	0.60
H8A	0.6186	0.0775	1.0420	0.086*	0.60
H8E	0.8356	0.1177	0.9921	0.086*	0.40
H8D	0.7220	0.0065	1.0504	0.086*	0.40
H8F	0.6094	0.1893	1.0037	0.086*	0.40
C9	0.0112 (3)	0.6238 (3)	0.7883 (2)	0.0442 (6)
H9	−0.0947	0.6218	0.7473	0.053*
C10	0.2943 (4)	0.4853 (3)	0.9244 (3)	0.0616 (7)
H10A	0.4070	0.4350	0.8825	0.092*
H10B	0.3051	0.4261	1.0080	0.092*
H10C	0.2858	0.5910	0.9226	0.092*
C11	0.0897 (6)	0.3442 (3)	0.8741 (3)	0.0793 (10)
H11A	−0.0320	0.3659	0.8325	0.119*
H11B	0.0863	0.2947	0.9590	0.119*
H11C	0.1939	0.2747	0.8372	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0353 (2)	0.01589 (19)	0.0328 (2)	−0.00545 (13)	−0.00206 (13)	−0.00454 (13)
N1	0.0288 (8)	0.0178 (8)	0.0263 (8)	−0.0071 (6)	−0.0014 (6)	−0.0037 (6)
N2	0.0310 (8)	0.0161 (8)	0.0325 (9)	−0.0048 (7)	−0.0042 (7)	0.0012 (7)
N3	0.0475 (11)	0.0272 (10)	0.0455 (11)	−0.0102 (8)	0.0006 (9)	−0.0037 (8)
O1	0.0437 (8)	0.0194 (7)	0.0312 (8)	−0.0033 (6)	−0.0080 (6)	−0.0020 (6)
O2	0.0494 (9)	0.0298 (8)	0.0317 (8)	−0.0069 (7)	−0.0092 (6)	−0.0090 (6)
O3	0.0549 (9)	0.0284 (8)	0.0421 (9)	−0.0081 (7)	−0.0025 (7)	−0.0156 (7)
O4	0.0415 (8)	0.0192 (7)	0.0586 (10)	−0.0040 (6)	−0.0032 (7)	−0.0113 (7)
O5	0.0633 (11)	0.0276 (9)	0.0651 (12)	−0.0046 (8)	−0.0201 (9)	0.0046 (8)
O6	0.0358 (8)	0.0230 (7)	0.0548 (10)	−0.0097 (6)	0.0027 (7)	−0.0097 (7)
C1	0.0283 (10)	0.0239 (10)	0.0281 (10)	−0.0075 (8)	0.0003 (8)	−0.0050 (8)
C2	0.0248 (9)	0.0205 (9)	0.0264 (10)	−0.0081 (7)	0.0016 (7)	−0.0051 (7)
C3	0.0245 (9)	0.0199 (9)	0.0300 (10)	−0.0077 (7)	0.0017 (7)	−0.0045 (8)
C4	0.0285 (10)	0.0229 (10)	0.0410 (12)	−0.0089 (8)	0.0050 (9)	−0.0100 (9)
C5	0.0291 (10)	0.0199 (9)	0.0296 (10)	−0.0079 (8)	−0.0023 (8)	−0.0011 (7)
C6	0.0445 (12)	0.0277 (11)	0.0320 (11)	−0.0117 (9)	−0.0089 (9)	−0.0020 (8)
C7	0.0699 (17)	0.0634 (17)	0.0420 (14)	−0.0321 (14)	0.0123 (12)	−0.0188 (12)
C8	0.0653 (17)	0.0591 (17)	0.0402 (14)	−0.0146 (14)	0.0039 (12)	−0.0123 (12)
C9	0.0379 (12)	0.0437 (14)	0.0437 (13)	−0.0057 (10)	−0.0053 (10)	−0.0099 (11)
C10	0.0469 (14)	0.0528 (16)	0.0639 (18)	−0.0051 (12)	−0.0138 (13)	0.0076 (13)
C11	0.113 (3)	0.0437 (17)	0.089 (2)	−0.0384 (18)	0.014 (2)	−0.0156 (16)

Geometric parameters (Å, º) top

Zn1—N1	2.0643 (15)	C1—C2	1.479 (3)
Zn1—N1ⁱ	2.0643 (15)	C2—C3	1.372 (3)
Zn1—O6ⁱ	2.1616	C3—C4	1.488 (3)
Zn1—O6	2.1616	C5—C6	1.485 (3)
Zn1—O1	2.2053 (14)	C6—C7	1.520 (3)
Zn1—O1ⁱ	2.2053 (14)	C6—H6C	0.9700
N1—C5	1.331 (2)	C6—H6D	0.9700
N1—C2	1.375 (2)	C7—C8	1.505 (3)
N2—C5	1.346 (2)	C7—H7A	0.9700
N2—C3	1.369 (2)	C7—H7B	0.9700
N2—H1N1	0.8600	C8—H8B	0.9600
N3—C9	1.322 (3)	C8—H8C	0.9600
N3—C10	1.443 (3)	C8—H8A	0.9600
N3—C11	1.448 (3)	C8—H8E	0.9602
O1—C1	1.240 (2)	C8—H8D	0.9601
O2—C1	1.284 (2)	C8—H8F	0.9602
O2—H1O2	0.8200	C9—H9	0.9300
O3—C4	1.274 (2)	C10—H10A	0.9600
O3—H1O3	0.8200	C10—H10B	0.9600
O4—C4	1.234 (2)	C10—H10C	0.9600
O5—C9	1.223 (3)	C11—H11A	0.9600
O6—H1O6	0.8201	C11—H11B	0.9600
O6—H2O6	0.8200	C11—H11C	0.9600

N1—Zn1—N1ⁱ	180.0	O3—C4—C3	116.34 (16)
N1—Zn1—O6ⁱ	92.14 (5)	N1—C5—N2	110.03 (17)
N1ⁱ—Zn1—O6ⁱ	87.86 (5)	N1—C5—C6	126.12 (17)
N1—Zn1—O6	87.86 (5)	N2—C5—C6	123.80 (17)
N1ⁱ—Zn1—O6	92.14 (5)	C5—C6—C7	113.04 (18)
O6ⁱ—Zn1—O6	180.0	C5—C6—H6C	109.0
N1—Zn1—O1	78.58 (5)	C7—C6—H6C	109.0
N1ⁱ—Zn1—O1	101.43 (5)	C5—C6—H6D	109.0
O6ⁱ—Zn1—O1	88.98 (4)	C7—C6—H6D	109.0
O6—Zn1—O1	91.02 (4)	H6C—C6—H6D	107.8
N1—Zn1—O1ⁱ	101.43 (5)	C8—C7—C6	113.9 (2)
N1ⁱ—Zn1—O1ⁱ	78.57 (5)	C8—C7—H7A	108.8
O6ⁱ—Zn1—O1ⁱ	91.02 (4)	C6—C7—H7A	108.8
O6—Zn1—O1ⁱ	88.98 (4)	C8—C7—H7B	108.8
O1—Zn1—O1ⁱ	180.0	C6—C7—H7B	108.8
C5—N1—C2	106.21 (15)	H7A—C7—H7B	107.7
C5—N1—Zn1	141.02 (13)	C7—C8—H8B	109.5
C2—N1—Zn1	112.56 (12)	C7—C8—H8C	109.5
C5—N2—C3	108.91 (16)	C7—C8—H8A	109.5
C5—N2—H1N1	125.5	C7—C8—H8E	109.5
C3—N2—H1N1	125.5	C7—C8—H8D	109.5
C9—N3—C10	119.9 (2)	H8E—C8—H8D	109.5
C9—N3—C11	121.1 (2)	C7—C8—H8F	109.5
C10—N3—C11	118.4 (2)	H8E—C8—H8F	109.5
C1—O1—Zn1	112.88 (12)	H8D—C8—H8F	109.5
C1—O2—H1O2	110.3	O5—C9—N3	124.6 (2)
C4—O3—H1O3	117.8	O5—C9—H9	117.7
Zn1—O6—H1O6	112.3	N3—C9—H9	117.7
Zn1—O6—H2O6	109.2	N3—C10—H10A	109.5
H1O6—O6—H2O6	108.9	N3—C10—H10B	109.5
O1—C1—O2	123.54 (16)	H10A—C10—H10B	109.5
O1—C1—C2	118.08 (17)	N3—C10—H10C	109.5
O2—C1—C2	118.37 (16)	H10A—C10—H10C	109.5
C3—C2—N1	109.67 (16)	H10B—C10—H10C	109.5
C3—C2—C1	132.62 (17)	N3—C11—H11A	109.5
N1—C2—C1	117.71 (16)	N3—C11—H11B	109.5
N2—C3—C2	105.17 (16)	H11A—C11—H11B	109.5
N2—C3—C4	122.91 (17)	N3—C11—H11C	109.5
C2—C3—C4	131.90 (18)	H11A—C11—H11C	109.5
O4—C4—O3	124.73 (17)	H11B—C11—H11C	109.5
O4—C4—C3	118.93 (18)

N1ⁱ—Zn1—N1—C5	23 (100)	O1—C1—C2—N1	2.6 (3)
O6ⁱ—Zn1—N1—C5	−94.0 (2)	O2—C1—C2—N1	−175.99 (15)
O6—Zn1—N1—C5	86.0 (2)	C5—N2—C3—C2	0.5 (2)
O1—Zn1—N1—C5	177.5 (2)	C5—N2—C3—C4	−178.27 (17)
O1ⁱ—Zn1—N1—C5	−2.5 (2)	N1—C2—C3—N2	−0.2 (2)
N1ⁱ—Zn1—N1—C2	−151 (100)	C1—C2—C3—N2	−179.58 (19)
O6ⁱ—Zn1—N1—C2	92.28 (12)	N1—C2—C3—C4	178.35 (18)
O6—Zn1—N1—C2	−87.72 (12)	C1—C2—C3—C4	−1.0 (4)
O1—Zn1—N1—C2	3.76 (12)	N2—C3—C4—O4	−0.5 (3)
O1ⁱ—Zn1—N1—C2	−176.24 (12)	C2—C3—C4—O4	−178.83 (17)
N1—Zn1—O1—C1	−2.53 (13)	N2—C3—C4—O3	178.75 (15)
N1ⁱ—Zn1—O1—C1	177.47 (13)	C2—C3—C4—O3	0.4 (3)
O6ⁱ—Zn1—O1—C1	−94.92 (13)	C2—N1—C5—N2	0.4 (2)
O6—Zn1—O1—C1	85.08 (13)	Zn1—N1—C5—N2	−173.60 (14)
O1ⁱ—Zn1—O1—C1	168 (100)	C2—N1—C5—C6	−177.05 (18)
Zn1—O1—C1—O2	179.33 (13)	Zn1—N1—C5—C6	8.9 (3)
Zn1—O1—C1—C2	0.8 (2)	C3—N2—C5—N1	−0.6 (2)
C5—N1—C2—C3	−0.1 (2)	C3—N2—C5—C6	176.97 (17)
Zn1—N1—C2—C3	175.82 (12)	N1—C5—C6—C7	110.5 (2)
C5—N1—C2—C1	179.37 (16)	N2—C5—C6—C7	−66.6 (3)
Zn1—N1—C2—C1	−4.7 (2)	C5—C6—C7—C8	−176.5 (2)
O1—C1—C2—C3	−178.04 (19)	C10—N3—C9—O5	−3.7 (4)
O2—C1—C2—C3	3.3 (3)	C11—N3—C9—O5	−174.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H2O6···O4ⁱⁱ	0.82	2.16	2.9594 (14)	167
O6—H1O6···O4ⁱⁱⁱ	0.82	1.98	2.796	175
O3—H1O3···O2	0.82	1.67	2.478	169
O2—H1O2···O3	0.82	1.66	2.478	177
N2—H1N1···O5^iv	0.86	1.84	2.6789 (17)	166

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r	641.94
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.3619 (9), 9.3194 (13), 11.2301 (15)
α, β, γ (°)	76.281 (1), 87.621 (2), 68.888 (1)
V (Å³)	697.44 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.43 × 0.28 × 0.25

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.685, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	3640, 2425, 2205
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.06
No. of reflections	2425
No. of parameters	179
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H2O6···O4ⁱ	0.82	2.16	2.9594 (14)	166.8
O6—H1O6···O4ⁱⁱ	0.82	1.98	2.796	175.3
O3—H1O3···O2	0.82	1.67	2.478	169.1
O2—H1O2···O3	0.82	1.66	2.478	177.0
N2—H1N1···O5ⁱⁱⁱ	0.86	1.84	2.6789 (17)	166.0

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

Acknowledgements

The authors acknowledge Pingdingshan University for support of this work.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Maji, T. K., Mostafa, G., Chang, H. C. & Kitagawa, S. (2005). Chem. Commun. pp. 2436–2438 CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, R. Q. & Zhang, X. M. (2006). Inorg. Chem. 45, 4801–4810. Web of Science PubMed Google Scholar

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