Bis(μ2-pyridine-2-carboxamide oximato)bis­[(pyridine-2-carboxamide oxime)zinc] dinitrate

Deng, X.-H.; Ran, J.-W.

doi:10.1107/S1600536811034908

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1323-m1324

doi:10.1107/S1600536811034908

Open

access

Bis(μ₂-pyridine-2-carboxamide oximato)bis[(pyridine-2-carboxamide oxime)zinc] dinitrate

Xiao-Hui Deng ^a ^* and Jing-Wen Ran ^b

^aInstitute of Cash Crops, Hubei Academy of Agricultural Science, Wuhan 430064, People's Republic of China, and ^bKey Laboratory of Industrial Ecology and Environmental Engineering (MOE) and State Key Laboratory of Fine Chemical, School of Environmental Science and Technology, Dalian University of Technology, Dalian 116024, People's Republic of China
^*Correspondence e-mail: xhdengyy@yahoo.com.cn

(Received 20 August 2011; accepted 25 August 2011; online 31 August 2011)

In the title dinuclear compound, [Zn₂(C₆H₆N₃O)₂(C₆H₇N₃O)₂](NO₃)₂, the Zn^II cation is N,N′-chelated by one pyridine-2-carboxamide oximate anion and one pyridine-2-carboxamide oxime molecule, and is further bridged by an oxime O atom from the adjacent pyridine-2-carboxamide oximate anion, forming a distorted trigonal bipyramidal coordination. Two pyridine-2-carboxamide oximate anions bridge two Zn^II cations to form the centrosymmetric dinuclear molecule. Extensive O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds are present in the crystal structure.

Related literature

For similar metal complexes, see: Papatriantafyllopoulou et al. (2008 ); Stamatatos et al. (2006a ,b ). For the synthesis of the ligand, see: Bernasek (1957 ).

Experimental

Crystal data

[Zn₂(C₆H₆N₃O)₂(C₆H₇N₃O)₂](NO₃)₂
M_r = 801.33
Monoclinic, P 2₁ /n
a = 7.4125 (14) Å
b = 22.201 (4) Å
c = 9.4225 (17) Å
β = 106.794 (2)°
V = 1484.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.70 mm⁻¹
T = 293 K
0.51 × 0.48 × 0.39 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.478, T_max = 0.557
8302 measured reflections
2632 independent reflections
2297 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.117
S = 1.03
2632 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O2	1.981 (3)
Zn1—N1	2.148 (3)
Zn1—N3	2.064 (3)
Zn1—N4	2.128 (3)
Zn1—N6	2.099 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.98	2.767 (4)	162
O1—H1⋯N6	0.82	2.43	3.018 (4)	129
N2—H2A⋯O2ⁱⁱ	0.86	2.32	3.108 (5)	152
N2—H2B⋯O5ⁱⁱⁱ	0.86	2.35	3.180 (5)	162
N5—H5A⋯O4	0.86	2.18	2.900 (5)	142
N5—H5B⋯O5^iv	0.86	2.18	2.985 (5)	156
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z; (iii) -x+2, -y+1, -z+2; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034908/xu5304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034908/xu5304Isup2.hkl

checkCIF report

Comment top

Transition metal compounds have been of great interest for many years. They are very important in the development of coordination chemistry. As an extension of work on the structural characterization of Zn compounds, we report here the crystal structure of a new dinuclear zinc(II) compound(I) (Scheme). Compound (I) is a symmetric dinuclear ZnII complex (Fig. 1). The ZnII ion in the compound is five-coordinated by four N and an O atoms from ligands. Each of these ligands chelates one ZnII atom forming a five-membered ZnNCCN chelating ring, while its oximate oxygen atom is terminally bound to the other metal center. The Zn1—N1 and Zn1—N4 bond distances are longer than the Zn1—N3 and Zn1—N6 bond distances. The N3—Zn1—N6 angle is smaller than the N1—Zn1—N4 angle (Table 1). The molecules are stacked along the a axis and display N—H···O and O—H···O hydrogen-bonds interaction (Fig. 2).

Related literature top

For similar metal complexes, see: Papatriantafyllopoulou et al. (2008); Stamatatos et al. (2006a,b). For the synthesis of the ligand, see: Bernasek (1957).

Experimental top

The synthesis of pyridine-2-amidoxine was carried out according to literature (Bernasek, 1957). The title compound was synthesized by adding solid Zn(NO₃)₂.6H₂O (297 mg, 1 mmol) to a solution of ligands (274 mg, 2 mmol) and NaOH (40 mg, 1 mmol) in ethanol/water (3:1, 20 ml), then the mixture was stirred for 2 h at room temperature. The solution was filtered and the filtrate was allowed to stand in air for 3 d, and yellow crystals were formed at the bottom of the vessel on slow evaporation of the solvent at room temperature. Yield: 48%. Anal. Calcd for C₂₄H₂₆N₁₄Zn₂O₁₀: C 35.97, H 3.27, N 24.46. Found: C 35.94, H 3.29, N 23.93.

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

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packed diagram for the title compound, viewed down the a axis with hydrogen bonds drawn as dashed lines.

Bis(µ₂-pyridine-2-carboxamide oximato)bis[(pyridine-2-carboxamide oxime)zinc] dinitrate top

Crystal data top

[Zn₂(C₆H₆N₃O)₂(C₆H₇N₃O)₂](NO₃)₂	F(000) = 816
M_r = 801.33	D_x = 1.793 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2632 reflections
a = 7.4125 (14) Å	θ = 1.8–25.1°
b = 22.201 (4) Å	µ = 1.70 mm⁻¹
c = 9.4225 (17) Å	T = 293 K
β = 106.794 (2)°	Block, yellow
V = 1484.5 (5) Å³	0.51 × 0.48 × 0.39 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2632 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→6
T_min = 0.478, T_max = 0.557	k = −26→26
8302 measured reflections	l = −9→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0547P)² + 4.2299P] where P = (F_o² + 2F_c²)/3
2632 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 1.43 e Å⁻³
0 restraints	Δρ_min = −0.97 e Å⁻³

Crystal data top

[Zn₂(C₆H₆N₃O)₂(C₆H₇N₃O)₂](NO₃)₂	V = 1484.5 (5) Å³
M_r = 801.33	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4125 (14) Å	µ = 1.70 mm⁻¹
b = 22.201 (4) Å	T = 293 K
c = 9.4225 (17) Å	0.51 × 0.48 × 0.39 mm
β = 106.794 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2632 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2297 reflections with I > 2σ(I)
T_min = 0.478, T_max = 0.557	R_int = 0.023
8302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 1.43 e Å⁻³
2632 reflections	Δρ_min = −0.97 e Å⁻³
209 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	0.46944 (6)	0.437379 (19)	0.86499 (5)	0.02829 (17)
O2	0.3307 (4)	0.44030 (11)	1.0158 (3)	0.0305 (6)
N6	0.5478 (4)	0.52822 (14)	0.8642 (3)	0.0279 (7)
O1	0.8933 (4)	0.45773 (13)	1.0281 (4)	0.0412 (7)
H1	0.8498	0.4919	1.0208	0.062*
C12	0.4742 (5)	0.55977 (16)	0.7481 (4)	0.0290 (8)
N3	0.7493 (5)	0.41671 (15)	0.9631 (4)	0.0326 (7)
C11	0.3546 (5)	0.52544 (17)	0.6194 (4)	0.0302 (8)
N1	0.4877 (5)	0.34274 (15)	0.8238 (4)	0.0321 (7)
N4	0.3239 (5)	0.46677 (15)	0.6470 (4)	0.0311 (7)
N5	0.5021 (6)	0.61900 (15)	0.7361 (4)	0.0465 (10)
H5A	0.5739	0.6385	0.8099	0.056*
H5B	0.4482	0.6375	0.6547	0.056*
N7	0.6922 (6)	0.77875 (19)	0.9401 (5)	0.0590 (5)
N2	0.9964 (5)	0.35112 (17)	0.9759 (4)	0.0429 (9)
H2A	1.0797	0.3778	1.0161	0.051*
H2B	1.0309	0.3156	0.9583	0.051*
C5	0.6647 (5)	0.32001 (17)	0.8733 (4)	0.0298 (8)
C8	0.1400 (7)	0.4564 (2)	0.3942 (5)	0.0431 (11)
H8	0.0665	0.4321	0.3194	0.052*
C10	0.2807 (6)	0.55061 (19)	0.4812 (5)	0.0383 (10)
H10	0.3038	0.5908	0.4647	0.046*
C6	0.8138 (5)	0.36488 (17)	0.9409 (4)	0.0298 (8)
O5	0.8612 (5)	0.78443 (16)	1.0109 (4)	0.0590 (5)
O3	0.5941 (5)	0.82406 (15)	0.9079 (4)	0.0590 (5)
O4	0.6244 (5)	0.72889 (15)	0.9025 (4)	0.0590 (5)
C7	0.2194 (7)	0.43374 (19)	0.5347 (5)	0.0406 (10)
H7	0.1992	0.3934	0.5520	0.049*
C4	0.7013 (7)	0.25955 (19)	0.8636 (5)	0.0402 (10)
H4	0.8237	0.2449	0.8987	0.048*
C3	0.5540 (7)	0.22116 (19)	0.8011 (5)	0.0462 (11)
H3	0.5762	0.1803	0.7922	0.055*
C9	0.1715 (6)	0.5154 (2)	0.3668 (5)	0.0431 (11)
H9	0.1203	0.5317	0.2729	0.052*
C1	0.3466 (6)	0.30447 (19)	0.7682 (5)	0.0380 (10)
H1A	0.2242	0.3194	0.7389	0.046*
C2	0.3739 (7)	0.2436 (2)	0.7522 (5)	0.0428 (11)
H2	0.2727	0.2184	0.7092	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0276 (3)	0.0250 (3)	0.0300 (3)	0.00004 (17)	0.00468 (19)	−0.00044 (17)
O2	0.0287 (14)	0.0296 (14)	0.0315 (14)	−0.0055 (11)	0.0062 (12)	−0.0041 (11)
N6	0.0281 (16)	0.0260 (16)	0.0276 (17)	−0.0017 (13)	0.0049 (13)	−0.0021 (13)
O1	0.0293 (15)	0.0309 (15)	0.0560 (19)	−0.0054 (12)	0.0003 (14)	−0.0053 (14)
C12	0.030 (2)	0.0242 (18)	0.033 (2)	0.0029 (15)	0.0079 (17)	−0.0004 (15)
N3	0.0253 (17)	0.0295 (17)	0.0394 (19)	−0.0038 (14)	0.0039 (14)	−0.0009 (14)
C11	0.029 (2)	0.0298 (19)	0.032 (2)	0.0051 (16)	0.0094 (16)	0.0001 (16)
N1	0.0302 (17)	0.0287 (17)	0.0348 (18)	−0.0006 (14)	0.0053 (14)	−0.0003 (14)
N4	0.0341 (18)	0.0279 (16)	0.0286 (17)	0.0006 (14)	0.0048 (14)	−0.0003 (13)
N5	0.061 (3)	0.0255 (18)	0.042 (2)	−0.0020 (17)	−0.0027 (19)	0.0038 (15)
N7	0.0512 (11)	0.0453 (9)	0.0727 (13)	−0.0021 (8)	0.0056 (9)	−0.0090 (9)
N2	0.0279 (18)	0.0374 (19)	0.059 (2)	0.0032 (15)	0.0050 (17)	−0.0044 (17)
C5	0.033 (2)	0.0289 (19)	0.029 (2)	0.0016 (16)	0.0098 (16)	0.0010 (16)
C8	0.045 (3)	0.046 (3)	0.033 (2)	−0.002 (2)	0.0034 (19)	−0.0070 (19)
C10	0.043 (2)	0.035 (2)	0.037 (2)	0.0052 (18)	0.0099 (19)	0.0056 (18)
C6	0.029 (2)	0.030 (2)	0.029 (2)	0.0030 (16)	0.0057 (16)	0.0052 (16)
O5	0.0512 (11)	0.0453 (9)	0.0727 (13)	−0.0021 (8)	0.0056 (9)	−0.0090 (9)
O3	0.0512 (11)	0.0453 (9)	0.0727 (13)	−0.0021 (8)	0.0056 (9)	−0.0090 (9)
O4	0.0512 (11)	0.0453 (9)	0.0727 (13)	−0.0021 (8)	0.0056 (9)	−0.0090 (9)
C7	0.046 (3)	0.032 (2)	0.037 (2)	−0.0053 (18)	0.002 (2)	−0.0044 (18)
C4	0.044 (2)	0.033 (2)	0.043 (3)	0.0053 (18)	0.011 (2)	0.0009 (18)
C3	0.061 (3)	0.028 (2)	0.048 (3)	0.000 (2)	0.013 (2)	−0.0053 (19)
C9	0.043 (3)	0.051 (3)	0.032 (2)	0.006 (2)	0.0056 (19)	0.0050 (19)
C1	0.035 (2)	0.038 (2)	0.038 (2)	−0.0052 (18)	0.0059 (18)	0.0014 (18)
C2	0.050 (3)	0.039 (2)	0.038 (2)	−0.015 (2)	0.010 (2)	−0.0048 (19)

Geometric parameters (Å, º) top

Zn1—O2	1.981 (3)	N7—O4	1.225 (5)
Zn1—N1	2.148 (3)	N7—O5	1.244 (5)
Zn1—N3	2.064 (3)	N2—C6	1.333 (5)
Zn1—N4	2.128 (3)	N2—H2A	0.8600
Zn1—N6	2.099 (3)	N2—H2B	0.8600
O2—N6ⁱ	1.411 (4)	C5—C4	1.378 (6)
N6—C12	1.281 (5)	C5—C6	1.487 (5)
N6—O2ⁱ	1.411 (4)	C8—C9	1.368 (7)
O1—N3	1.402 (4)	C8—C7	1.379 (6)
O1—H1	0.8200	C8—H8	0.9300
C12—N5	1.341 (5)	C10—C9	1.386 (6)
C12—C11	1.489 (5)	C10—H10	0.9300
N3—C6	1.286 (5)	C7—H7	0.9300
C11—N4	1.361 (5)	C4—C3	1.376 (6)
C11—C10	1.377 (6)	C4—H4	0.9300
N1—C1	1.332 (5)	C3—C2	1.374 (7)
N1—C5	1.357 (5)	C3—H3	0.9300
N4—C7	1.336 (5)	C9—H9	0.9300
N5—H5A	0.8600	C1—C2	1.381 (6)
N5—H5B	0.8600	C1—H1A	0.9300
N7—O3	1.227 (5)	C2—H2	0.9300

O2—Zn1—N3	110.42 (13)	O4—N7—O5	120.8 (4)
O2—Zn1—N6	99.93 (12)	C6—N2—H2A	120.0
N3—Zn1—N6	88.39 (13)	C6—N2—H2B	120.0
O2—Zn1—N4	117.30 (12)	H2A—N2—H2B	120.0
N3—Zn1—N4	131.62 (14)	N1—C5—C4	121.9 (4)
N6—Zn1—N4	76.45 (12)	N1—C5—C6	115.0 (3)
O2—Zn1—N1	103.55 (12)	C4—C5—C6	123.0 (4)
N3—Zn1—N1	75.87 (13)	C9—C8—C7	118.8 (4)
N6—Zn1—N1	155.12 (13)	C9—C8—H8	120.6
N4—Zn1—N1	99.58 (13)	C7—C8—H8	120.6
N6ⁱ—O2—Zn1	104.3 (2)	C9—C10—C11	119.3 (4)
C12—N6—O2ⁱ	115.4 (3)	C9—C10—H10	120.3
C12—N6—Zn1	118.6 (3)	C11—C10—H10	120.3
O2ⁱ—N6—Zn1	125.9 (2)	N3—C6—N2	124.3 (4)
N3—O1—H1	109.5	N3—C6—C5	113.8 (3)
N6—C12—N5	124.8 (4)	N2—C6—C5	121.9 (4)
N6—C12—C11	115.0 (3)	N4—C7—C8	123.3 (4)
N5—C12—C11	120.2 (4)	N4—C7—H7	118.3
C6—N3—O1	112.4 (3)	C8—C7—H7	118.3
C6—N3—Zn1	119.9 (3)	C5—C4—C3	119.0 (4)
O1—N3—Zn1	126.2 (2)	C5—C4—H4	120.5
N4—C11—C10	121.8 (4)	C3—C4—H4	120.5
N4—C11—C12	115.3 (3)	C2—C3—C4	119.5 (4)
C10—C11—C12	122.9 (4)	C2—C3—H3	120.2
C1—N1—C5	118.0 (3)	C4—C3—H3	120.2
C1—N1—Zn1	127.7 (3)	C8—C9—C10	119.1 (4)
C5—N1—Zn1	114.0 (2)	C8—C9—H9	120.4
C7—N4—C11	117.7 (3)	C10—C9—H9	120.4
C7—N4—Zn1	127.8 (3)	N1—C1—C2	123.0 (4)
C11—N4—Zn1	114.3 (2)	N1—C1—H1A	118.5
C12—N5—H5A	120.0	C2—C1—H1A	118.5
C12—N5—H5B	120.0	C3—C2—C1	118.5 (4)
H5A—N5—H5B	120.0	C3—C2—H2	120.8
O3—N7—O4	120.3 (4)	C1—C2—H2	120.8
O3—N7—O5	118.9 (4)

N3—Zn1—O2—N6ⁱ	43.2 (2)	C12—C11—N4—C7	−179.2 (4)
N6—Zn1—O2—N6ⁱ	−48.8 (2)	C10—C11—N4—Zn1	175.9 (3)
N4—Zn1—O2—N6ⁱ	−128.6 (2)	C12—C11—N4—Zn1	−3.6 (4)
N1—Zn1—O2—N6ⁱ	123.0 (2)	O2—Zn1—N4—C7	−90.2 (4)
O2—Zn1—N6—C12	−112.5 (3)	N3—Zn1—N4—C7	100.1 (4)
N3—Zn1—N6—C12	137.0 (3)	N6—Zn1—N4—C7	175.4 (4)
N4—Zn1—N6—C12	3.4 (3)	N1—Zn1—N4—C7	20.5 (4)
N1—Zn1—N6—C12	86.9 (4)	O2—Zn1—N4—C11	94.8 (3)
O2—Zn1—N6—O2ⁱ	64.1 (3)	N3—Zn1—N4—C11	−74.9 (3)
N3—Zn1—N6—O2ⁱ	−46.3 (3)	N6—Zn1—N4—C11	0.4 (3)
N4—Zn1—N6—O2ⁱ	−180.0 (3)	N1—Zn1—N4—C11	−154.5 (3)
N1—Zn1—N6—O2ⁱ	−96.5 (4)	C1—N1—C5—C4	1.8 (6)
O2ⁱ—N6—C12—N5	−1.5 (6)	Zn1—N1—C5—C4	176.4 (3)
Zn1—N6—C12—N5	175.5 (3)	C1—N1—C5—C6	−177.0 (4)
O2ⁱ—N6—C12—C11	176.8 (3)	Zn1—N1—C5—C6	−2.4 (4)
Zn1—N6—C12—C11	−6.3 (5)	N4—C11—C10—C9	0.2 (7)
O2—Zn1—N3—C6	109.2 (3)	C12—C11—C10—C9	179.6 (4)
N6—Zn1—N3—C6	−150.8 (3)	O1—N3—C6—N2	0.3 (6)
N4—Zn1—N3—C6	−80.6 (3)	Zn1—N3—C6—N2	167.2 (3)
N1—Zn1—N3—C6	9.7 (3)	O1—N3—C6—C5	179.5 (3)
O2—Zn1—N3—O1	−86.0 (3)	Zn1—N3—C6—C5	−13.7 (5)
N6—Zn1—N3—O1	14.0 (3)	N1—C5—C6—N3	10.2 (5)
N4—Zn1—N3—O1	84.3 (3)	C4—C5—C6—N3	−168.6 (4)
N1—Zn1—N3—O1	174.6 (3)	N1—C5—C6—N2	−170.7 (4)
N6—C12—C11—N4	6.5 (5)	C4—C5—C6—N2	10.6 (6)
N5—C12—C11—N4	−175.1 (4)	C11—N4—C7—C8	−1.0 (7)
N6—C12—C11—C10	−173.0 (4)	Zn1—N4—C7—C8	−175.8 (4)
N5—C12—C11—C10	5.4 (6)	C9—C8—C7—N4	1.1 (8)
O2—Zn1—N1—C1	62.8 (4)	N1—C5—C4—C3	0.4 (7)
N3—Zn1—N1—C1	170.8 (4)	C6—C5—C4—C3	179.0 (4)
N6—Zn1—N1—C1	−136.9 (4)	C5—C4—C3—C2	−1.1 (7)
N4—Zn1—N1—C1	−58.5 (4)	C7—C8—C9—C10	−0.5 (7)
O2—Zn1—N1—C5	−111.2 (3)	C11—C10—C9—C8	−0.1 (7)
N3—Zn1—N1—C5	−3.2 (3)	C5—N1—C1—C2	−3.3 (6)
N6—Zn1—N1—C5	49.1 (5)	Zn1—N1—C1—C2	−177.1 (3)
N4—Zn1—N1—C5	127.5 (3)	C4—C3—C2—C1	−0.4 (7)
C10—C11—N4—C7	0.3 (6)	N1—C1—C2—C3	2.6 (7)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.98	2.767 (4)	162
O1—H1···N6	0.82	2.43	3.018 (4)	129
N2—H2A···O2ⁱⁱ	0.86	2.32	3.108 (5)	152
N2—H2B···O5ⁱⁱⁱ	0.86	2.35	3.180 (5)	162
N5—H5A···O4	0.86	2.18	2.900 (5)	142
N5—H5B···O5^iv	0.86	2.18	2.985 (5)	156

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₆H₆N₃O)₂(C₆H₇N₃O)₂](NO₃)₂
M_r	801.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.4125 (14), 22.201 (4), 9.4225 (17)
β (°)	106.794 (2)
V (Å³)	1484.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.70
Crystal size (mm)	0.51 × 0.48 × 0.39

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.478, 0.557
No. of measured, independent and observed [I > 2σ(I)] reflections	8302, 2632, 2297
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.117, 1.03
No. of reflections	2632
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −0.97

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

Selected bond lengths (Å) top

Zn1—O2	1.981 (3)	Zn1—N4	2.128 (3)
Zn1—N1	2.148 (3)	Zn1—N6	2.099 (3)
Zn1—N3	2.064 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.98	2.767 (4)	161.7
O1—H1···N6	0.82	2.43	3.018 (4)	128.9
N2—H2A···O2ⁱⁱ	0.86	2.32	3.108 (5)	152.1
N2—H2B···O5ⁱⁱⁱ	0.86	2.35	3.180 (5)	162.3
N5—H5A···O4	0.86	2.18	2.900 (5)	141.5
N5—H5B···O5^iv	0.86	2.18	2.985 (5)	155.7

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

Acknowledgements

The research was supported by the Natural Science Fund of Hubei Province (project ZRZ0140) and the National Natural Science Foundation of China (Nos. 20877013 and No.20837001). The authors thank Professor S.-M. Qiu of Hubei Academy of Agricultural Science for his valuable suggestions.

References

Bernasek, E. (1957). J. Org. Chem. 22, 1263–1264. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Papatriantafyllopoulou, C., Jones, L. F., Nguyen, T. D., Matamoros-Salvador, N., Cunha-Silva, L., Paz, F. A. A., Rocha, J., Evangelisti, M., Brechin, E. K. & Perlepes, S. P. (2008). Dalton Trans. pp. 3153–3155. 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
Stamatatos, T. C., Diamantopoulou, E., Tasiopoulos, A., Psycharis, V., Vicente, R., Raptopoulou, C. P., Nastopoulos, V., Escuer, A. & Perlepes, S. P. (2006a). Inorg. Chim. Acta, 359, 4149–4157. Google Scholar
Stamatatos, T. C., Pringouri, K. V., Raptopoulou, C. P., Vicente, R., Psycharis, V., Escuer, A. & Perlepes, S. P. (2006b). Inorg. Chem. Commun. 9, 1178–1182. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.