[μ-14,29-Di-tert-butyl-3,10,18,25-tetra­azatpenta­cyclo­[25.3.1.112,16.04,9.019,24]dotriaconta-1(31),4,6,8,12(32),14,16,19,21,23,27,29-dodeca­ene-31,32-diol­ato]bis­[(nitrato-κ2O,O′)zinc(II)]

Fan, L.-J.; Ma, J.-F.; Liu, B.

doi:10.1107/S1600536809028530

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m985

doi:10.1107/S1600536809028530

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[μ-14,29-Di-tert-butyl-3,10,18,25-tetraazatpentacyclo[25.3.1.1^12,16.0^4,9.0^19,24]dotriaconta-1(31),4,6,8,12(32),14,16,19,21,23,27,29-dodecaene-31,32-diolato]bis[(nitrato-κ²O,O′)zinc(II)]

Li-Jing Fan,^a Jian-Fang Ma ^a ^* and Bo Liu ^a

^aDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: majf247nenu@yahoo.com.cn

(Received 10 July 2009; accepted 20 July 2009; online 25 July 2009)

In the title centrosymmetric dinuclear zinc(II) complex, [Zn₂(C₃₆H₄₂N₄O₂)(NO₃)₂], the Zn^II atom has a distorted octahedral geometry, defined by two N atoms and two O atoms from the macrocyclic ligand and two O atoms from a chelating nitrate anion and are bridged by two phenolate O atoms, forming a four-membered Zn₂O₂ ring.

Related literature

For general background to the biochemistry of zinc(II) compounds, see: Bazzicalupi et al. (1997 ); Burley et al. (1990 ); Lipscomb & Straeter (1996 ); Roderick & Mathews (1993 ). For related structures, see: Dutta et al. (2005 ). For further synthetic details, see: Fan et al. (2009 ).

Experimental

Crystal data

[Zn₂(C₃₆H₄₂N₄O₂)(NO₃)₂]
M_r = 817.20
Monoclinic, P 2₁ /c
a = 13.7149 (8) Å
b = 18.0691 (10) Å
c = 7.3523 (3) Å
β = 101.110 (5)°
V = 1787.87 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 293 K
0.45 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.661, T_max = 0.752
15034 measured reflections
4340 independent reflections
1698 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.065
S = 0.91
4340 reflections
241 parameters
357 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N1	2.081 (4)
Zn1—N2	2.102 (3)
Zn1—O1	2.264 (3)
Zn1—O2	2.243 (3)
Zn1—O4	2.019 (2)
Zn1—O4ⁱ	2.043 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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/S1600536809028530/hy2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028530/hy2213Isup2.hkl

checkCIF report

Comment top

Dinuclear zinc(II) compounds have attracted much interest as a result of their significance in biological systems (Burley et al., 1990; Roderick & Mathews, 1993). In addition, some synthetic dinuclear zinc(II) compounds are found to have functions in dephosphorylation (Bazzicalupi et al., 1997). As part of our studies in this area, the title compound, a new dinuclear zinc(II) compound, has been synthesized and its structure is reported here (Fig. 1).

In the title centrosymmetric dinuclear zinc(II) compound, each of the two Zn^II atoms has a distorted octahedral geometry, defined by two N atoms and two O atoms from the macrocyclic (C₃₆H₄₂N₄O₂) ligand and two O atoms from a chelating nitrate anion. The two Zn atoms are bridged by two phenolate O atoms, forming a four-membered Zn₂O₂ ring. The Zn—O and Zn—N distances are normal (Table 1) (Dutta et al., 2005).

Related literature top

For general background to the biochemistry of zinc(II) compounds, see: Bazzicalupi et al. (1997); Burley et al. (1990); Lipscomb & Straeter (1996); Roderick & Mathews (1993). For related structures, see: Dutta et al. (2005). For further synthetic details, see: Fan et al. (2009).

Experimental top

The title compound was prepared by a reaction between the macrocyclic ligand C₃₆H₄₄N₄O₂ (H₂L), which was synthesized according to the published procedure (Fan et al., 2009), and zinc nitrate. A mixture of H₂L (0.135 g, 0.25 mmol) and Zn(NO₃)₂.6H₂O (0.149 g, 0.5 mmol) in ethanol (20 ml) was heated with stirring to yield a clear pale yellow solution. Filtration and cooling to room temperature resulted in the formation of a crystalline precipitate. Recrystallization by slow evaporation of an ethanol solution of the compound resulted in well formed yellow blocks of the title compound (yield 52%).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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. Molecular structure of the title compound. Displaceement ellipsoids are draw at the 30% probability level. H atoms have been omitted for clarity.

[µ-14,29-Di-tert-butyl-3,10,18,25- tetraazatpentacyclo[25.3.1.1^12,16.0^4,9.0^19,24]dotriaconta- 1(31),4,6,8,12 (32),14,16,19,21,23,27,29-dodecaene-31,32-diolato]bis[(nitrato- κ²O,O')zinc(II)] top

Crystal data top

[Zn₂(C₃₆H₄₂N₄O₂)(NO₃)₂]	F(000) = 848
M_r = 817.20	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2682 reflections
a = 13.7149 (8) Å	θ = 1.9–29.2°
b = 18.0691 (10) Å	µ = 1.40 mm⁻¹
c = 7.3523 (3) Å	T = 293 K
β = 101.110 (5)°	Block, yellow
V = 1787.87 (16) Å³	0.45 × 0.25 × 0.20 mm
Z = 2

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	4340 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
Detector resolution: 10.0 pixels mm^-1	θ_max = 29.3°, θ_min = 1.9°
ω scans	h = −16→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −24→24
T_min = 0.661, T_max = 0.752	l = −8→10
15034 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ²(F_o²) + (0.01P)²] where P = (F_o² + 2F_c²)/3
4340 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.66 e Å⁻³
357 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Zn₂(C₃₆H₄₂N₄O₂)(NO₃)₂]	V = 1787.87 (16) Å³
M_r = 817.20	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7149 (8) Å	µ = 1.40 mm⁻¹
b = 18.0691 (10) Å	T = 293 K
c = 7.3523 (3) Å	0.45 × 0.25 × 0.20 mm
β = 101.110 (5)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	4340 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1698 reflections with I > 2σ(I)
T_min = 0.661, T_max = 0.752	R_int = 0.099
15034 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	357 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.66 e Å⁻³
4340 reflections	Δρ_min = −0.45 e Å⁻³
241 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.2727 (3)	0.6078 (2)	0.1435 (5)	0.0401 (11)
C2	0.1724 (3)	0.6150 (2)	0.1476 (5)	0.0486 (12)
H2	0.1254	0.5897	0.0621	0.058*
C3	0.1424 (3)	0.6598 (2)	0.2783 (5)	0.0506 (12)
H3	0.0753	0.6651	0.2807	0.061*
C4	0.2122 (4)	0.6965 (2)	0.4047 (5)	0.0469 (12)
H4	0.1920	0.7266	0.4931	0.056*
C5	0.3108 (3)	0.6893 (2)	0.4022 (5)	0.0404 (11)
H5	0.3572	0.7141	0.4900	0.048*
C6	0.3426 (3)	0.6460 (2)	0.2723 (5)	0.0332 (10)
C7	0.5006 (3)	0.4041 (2)	−0.4386 (4)	0.0334 (11)
H7A	0.4997	0.3731	−0.5467	0.040*
H7B	0.5382	0.4484	−0.4537	0.040*
C8	0.3954 (3)	0.4258 (2)	−0.4294 (4)	0.0296 (9)
C9	0.3152 (3)	0.3961 (2)	−0.5486 (5)	0.0386 (10)
H9	0.3268	0.3600	−0.6320	0.046*
C10	0.2177 (3)	0.4175 (3)	−0.5504 (5)	0.0427 (10)
C11	0.2043 (3)	0.4716 (2)	−0.4249 (5)	0.0464 (11)
H11	0.1400	0.4879	−0.4243	0.056*
C12	0.2823 (3)	0.5029 (2)	−0.2995 (5)	0.0375 (11)
C13	0.3800 (3)	0.4796 (2)	−0.3002 (5)	0.0322 (10)
C14	0.2598 (3)	0.5610 (3)	−0.1703 (5)	0.0584 (12)
H14A	0.2707	0.6085	−0.2244	0.070*
H14B	0.1894	0.5578	−0.1684	0.070*
C15	0.1319 (3)	0.3808 (3)	−0.6848 (6)	0.0525 (12)
C16	0.1355 (4)	0.2980 (3)	−0.6507 (6)	0.0896 (16)
H16A	0.1987	0.2791	−0.6668	0.134*
H16B	0.0835	0.2744	−0.7372	0.134*
H16C	0.1267	0.2882	−0.5266	0.134*
C17	0.1414 (3)	0.3929 (2)	−0.8848 (5)	0.0749 (14)
H17A	0.2044	0.3745	−0.9031	0.112*
H17B	0.1367	0.4448	−0.9128	0.112*
H17C	0.0889	0.3670	−0.9653	0.112*
C18	0.0325 (3)	0.4077 (3)	−0.6600 (6)	0.0918 (16)
H18A	0.0253	0.3993	−0.5344	0.138*
H18B	−0.0185	0.3813	−0.7427	0.138*
H18C	0.0268	0.4596	−0.6869	0.138*
N1	0.3096 (3)	0.5622 (2)	0.0108 (5)	0.0479 (11)
N2	0.4476 (3)	0.63682 (17)	0.2695 (4)	0.0315 (9)
N3	0.5574 (4)	0.6847 (2)	−0.1030 (5)	0.0470 (12)
O1	0.6025 (2)	0.63223 (18)	−0.0177 (4)	0.0545 (8)
O2	0.4639 (3)	0.68288 (18)	−0.1261 (4)	0.0575 (10)
O3	0.5992 (3)	0.73463 (18)	−0.1672 (4)	0.0714 (11)
O4	0.4592 (2)	0.50597 (14)	−0.1821 (3)	0.0309 (7)
Zn1	0.46177 (4)	0.57671 (3)	0.03129 (6)	0.03462 (15)
H1N	0.296 (3)	0.5176 (13)	0.031 (5)	0.052*
H2N	0.475 (3)	0.6800 (13)	0.282 (5)	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.034 (3)	0.050 (3)	0.040 (2)	0.006 (2)	0.017 (2)	−0.011 (2)
C2	0.037 (3)	0.065 (3)	0.045 (2)	0.003 (2)	0.012 (2)	−0.008 (2)
C3	0.038 (3)	0.063 (3)	0.055 (3)	0.006 (2)	0.019 (2)	−0.010 (2)
C4	0.046 (3)	0.052 (3)	0.045 (2)	0.011 (3)	0.014 (2)	−0.014 (2)
C5	0.038 (3)	0.045 (3)	0.039 (2)	0.003 (2)	0.010 (2)	−0.010 (2)
C6	0.029 (3)	0.041 (3)	0.032 (2)	0.009 (2)	0.012 (2)	0.0007 (19)
C7	0.036 (3)	0.039 (3)	0.026 (2)	0.004 (2)	0.0078 (19)	−0.0020 (19)
C8	0.030 (2)	0.033 (2)	0.0254 (19)	−0.003 (2)	0.0060 (18)	−0.003 (2)
C9	0.041 (2)	0.044 (2)	0.0300 (19)	0.001 (2)	0.0052 (19)	−0.0112 (18)
C10	0.033 (2)	0.052 (2)	0.041 (2)	−0.005 (2)	0.0022 (18)	−0.013 (2)
C11	0.031 (2)	0.063 (3)	0.043 (2)	0.003 (2)	0.004 (2)	−0.010 (2)
C12	0.035 (2)	0.042 (2)	0.034 (2)	0.004 (2)	0.003 (2)	−0.0104 (19)
C13	0.031 (2)	0.038 (2)	0.028 (2)	0.001 (2)	0.007 (2)	−0.0019 (19)
C14	0.043 (3)	0.078 (3)	0.051 (2)	0.020 (2)	0.001 (2)	−0.018 (2)
C15	0.034 (3)	0.061 (3)	0.061 (2)	0.001 (2)	0.006 (2)	−0.019 (2)
C16	0.083 (3)	0.087 (3)	0.088 (3)	−0.027 (3)	−0.011 (3)	−0.007 (3)
C17	0.064 (3)	0.089 (3)	0.062 (3)	−0.011 (3)	−0.013 (2)	−0.013 (3)
C18	0.048 (3)	0.120 (4)	0.101 (3)	−0.012 (3)	−0.002 (3)	−0.055 (3)
N1	0.032 (2)	0.065 (3)	0.046 (2)	0.000 (3)	0.0058 (19)	−0.017 (3)
N2	0.037 (3)	0.028 (2)	0.0292 (18)	0.004 (2)	0.0064 (18)	−0.0054 (17)
N3	0.071 (4)	0.031 (3)	0.041 (2)	0.005 (3)	0.018 (3)	−0.005 (2)
O1	0.058 (2)	0.046 (2)	0.062 (2)	−0.0080 (17)	0.0188 (18)	0.0047 (17)
O2	0.055 (3)	0.063 (3)	0.0534 (19)	0.003 (2)	0.007 (2)	−0.0025 (17)
O3	0.098 (3)	0.038 (2)	0.090 (2)	−0.012 (2)	0.046 (2)	0.0090 (19)
O4	0.032 (2)	0.0326 (18)	0.0283 (15)	0.0044 (15)	0.0067 (14)	−0.0065 (13)
Zn1	0.0343 (3)	0.0372 (3)	0.0319 (2)	0.0038 (4)	0.0052 (2)	−0.0047 (3)

Geometric parameters (Å, º) top

C1—C2	1.388 (5)	C14—H14A	0.9700
C1—C6	1.393 (5)	C14—H14B	0.9700
C1—N1	1.441 (5)	C15—C18	1.490 (5)
C2—C3	1.378 (5)	C15—C16	1.516 (6)
C2—H2	0.9300	C15—C17	1.517 (5)
C3—C4	1.369 (5)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.363 (5)	C16—H16C	0.9600
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.368 (5)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—N2	1.453 (5)	C18—H18A	0.9600
C7—N2ⁱ	1.502 (4)	C18—H18B	0.9600
C7—C8	1.510 (5)	C18—H18C	0.9600
C7—H7A	0.9700	Zn1—N1	2.081 (4)
C7—H7B	0.9700	N1—H1N	0.845 (19)
C8—C9	1.376 (5)	N2—C7ⁱ	1.502 (4)
C8—C13	1.404 (5)	Zn1—N2	2.102 (3)
C9—C10	1.390 (5)	N2—H2N	0.863 (19)
C9—H9	0.9300	N3—O3	1.212 (4)
C10—C11	1.380 (5)	N3—O1	1.234 (4)
C10—C15	1.534 (5)	N3—O2	1.262 (5)
C11—C12	1.391 (5)	Zn1—O1	2.264 (3)
C11—H11	0.9300	Zn1—O2	2.243 (3)
C12—C13	1.405 (5)	Zn1—O4	2.019 (2)
C12—C14	1.487 (5)	Zn1—O4ⁱ	2.043 (2)
C13—O4	1.341 (4)	Zn1—Zn1ⁱ	3.0302 (10)
C14—N1	1.375 (4)

C2—C1—C6	119.6 (4)	C15—C16—H16C	109.5
C2—C1—N1	123.1 (4)	H16A—C16—H16C	109.5
C6—C1—N1	117.3 (4)	H16B—C16—H16C	109.5
C3—C2—C1	120.0 (4)	C15—C17—H17A	109.5
C3—C2—H2	120.0	C15—C17—H17B	109.5
C1—C2—H2	120.0	H17A—C17—H17B	109.5
C4—C3—C2	119.6 (4)	C15—C17—H17C	109.5
C4—C3—H3	120.2	H17A—C17—H17C	109.5
C2—C3—H3	120.2	H17B—C17—H17C	109.5
C3—C4—C5	120.7 (4)	C15—C18—H18A	109.5
C3—C4—H4	119.7	C15—C18—H18B	109.5
C5—C4—H4	119.7	H18A—C18—H18B	109.5
C4—C5—C6	120.9 (4)	C15—C18—H18C	109.5
C4—C5—H5	119.5	H18A—C18—H18C	109.5
C6—C5—H5	119.5	H18B—C18—H18C	109.5
C5—C6—C1	119.2 (4)	C14—N1—C1	119.5 (4)
C5—C6—N2	121.6 (4)	C14—N1—Zn1	112.1 (3)
C1—C6—N2	119.1 (4)	C1—N1—Zn1	110.9 (3)
N2ⁱ—C7—C8	113.3 (3)	C14—N1—H1N	94 (3)
N2ⁱ—C7—H7A	108.9	C1—N1—H1N	108 (3)
C8—C7—H7A	108.9	Zn1—N1—H1N	111 (3)
N2ⁱ—C7—H7B	108.9	C6—N2—C7ⁱ	110.9 (3)
C8—C7—H7B	108.9	C6—N2—Zn1	108.8 (2)
H7A—C7—H7B	107.7	C7ⁱ—N2—Zn1	109.3 (2)
C9—C8—C13	119.6 (4)	C6—N2—H2N	108 (3)
C9—C8—C7	121.6 (4)	C7ⁱ—N2—H2N	103 (3)
C13—C8—C7	118.7 (4)	Zn1—N2—H2N	116 (3)
C8—C9—C10	123.2 (4)	O3—N3—O1	122.8 (5)
C8—C9—H9	118.4	O3—N3—O2	120.7 (5)
C10—C9—H9	118.4	O1—N3—O2	116.4 (5)
C11—C10—C9	116.3 (4)	N3—O1—Zn1	93.6 (3)
C11—C10—C15	123.5 (4)	N3—O2—Zn1	93.8 (3)
C9—C10—C15	120.2 (4)	C13—O4—Zn1	128.2 (2)
C10—C11—C12	123.1 (4)	C13—O4—Zn1ⁱ	111.8 (2)
C10—C11—H11	118.5	Zn1—O4—Zn1ⁱ	96.50 (9)
C12—C11—H11	118.5	O4—Zn1—O4ⁱ	83.50 (9)
C11—C12—C13	119.2 (4)	O4—Zn1—N1	89.82 (13)
C11—C12—C14	118.9 (4)	O4ⁱ—Zn1—N1	111.54 (13)
C13—C12—C14	121.9 (4)	O4—Zn1—N2	169.86 (13)
O4—C13—C12	123.1 (4)	O4ⁱ—Zn1—N2	92.88 (11)
O4—C13—C8	118.4 (4)	N1—Zn1—N2	82.68 (14)
C12—C13—C8	118.6 (4)	O4—Zn1—O2	98.08 (11)
N1—C14—C12	120.3 (4)	O4ⁱ—Zn1—O2	147.90 (13)
N1—C14—H14A	107.2	N1—Zn1—O2	100.54 (14)
C12—C14—H14A	107.2	N2—Zn1—O2	90.02 (12)
N1—C14—H14B	107.2	O4—Zn1—O1	92.56 (11)
C12—C14—H14B	107.2	O4ⁱ—Zn1—O1	91.78 (11)
H14A—C14—H14B	106.9	N1—Zn1—O1	156.68 (13)
C18—C15—C16	107.6 (4)	N2—Zn1—O1	97.03 (12)
C18—C15—C17	108.8 (4)	O2—Zn1—O1	56.16 (11)
C16—C15—C17	107.2 (4)	O4—Zn1—Zn1ⁱ	42.06 (7)
C18—C15—C10	112.8 (4)	O4ⁱ—Zn1—Zn1ⁱ	41.45 (6)
C16—C15—C10	108.9 (4)	N1—Zn1—Zn1ⁱ	104.20 (11)
C17—C15—C10	111.4 (4)	N2—Zn1—Zn1ⁱ	133.61 (9)
C15—C16—H16A	109.5	O2—Zn1—Zn1ⁱ	131.67 (9)
C15—C16—H16B	109.5	O1—Zn1—Zn1ⁱ	92.91 (9)
H16A—C16—H16B	109.5

C6—C1—C2—C3	0.1 (6)	C12—C13—O4—Zn1	4.7 (5)
N1—C1—C2—C3	−179.9 (4)	C8—C13—O4—Zn1	−174.7 (2)
C1—C2—C3—C4	−0.6 (6)	C12—C13—O4—Zn1ⁱ	122.7 (4)
C2—C3—C4—C5	0.2 (7)	C8—C13—O4—Zn1ⁱ	−56.6 (4)
C3—C4—C5—C6	0.8 (7)	C13—O4—Zn1—O4ⁱ	124.4 (3)
C4—C5—C6—C1	−1.2 (6)	Zn1ⁱ—O4—Zn1—O4ⁱ	0.0
C4—C5—C6—N2	−179.0 (4)	C13—O4—Zn1—N1	12.7 (3)
C2—C1—C6—C5	0.8 (6)	Zn1ⁱ—O4—Zn1—N1	−111.71 (13)
N1—C1—C6—C5	−179.2 (4)	C13—O4—Zn1—N2	54.8 (8)
C2—C1—C6—N2	178.7 (4)	Zn1ⁱ—O4—Zn1—N2	−69.6 (7)
N1—C1—C6—N2	−1.4 (6)	C13—O4—Zn1—O2	−87.9 (3)
N2ⁱ—C7—C8—C9	−114.2 (4)	Zn1ⁱ—O4—Zn1—O2	147.67 (13)
N2ⁱ—C7—C8—C13	68.2 (5)	C13—O4—Zn1—O1	−144.1 (3)
C13—C8—C9—C10	0.9 (6)	Zn1ⁱ—O4—Zn1—O1	91.50 (12)
C7—C8—C9—C10	−176.7 (4)	C13—O4—Zn1—Zn1ⁱ	124.4 (3)
C8—C9—C10—C11	0.4 (6)	C14—N1—Zn1—O4	−41.6 (3)
C8—C9—C10—C15	−178.8 (4)	C1—N1—Zn1—O4	−177.9 (3)
C9—C10—C11—C12	−1.3 (6)	C14—N1—Zn1—O4ⁱ	−124.5 (3)
C15—C10—C11—C12	177.8 (4)	C1—N1—Zn1—O4ⁱ	99.2 (3)
C10—C11—C12—C13	0.9 (6)	C14—N1—Zn1—N2	145.2 (3)
C10—C11—C12—C14	179.8 (4)	C1—N1—Zn1—N2	8.9 (3)
C11—C12—C13—O4	−178.9 (3)	C14—N1—Zn1—O2	56.6 (3)
C14—C12—C13—O4	2.2 (6)	C1—N1—Zn1—O2	−79.7 (3)
C11—C12—C13—C8	0.5 (6)	C14—N1—Zn1—O1	54.5 (5)
C14—C12—C13—C8	−178.4 (4)	C1—N1—Zn1—O1	−81.8 (4)
C9—C8—C13—O4	178.1 (3)	C14—N1—Zn1—Zn1ⁱ	−81.5 (3)
C7—C8—C13—O4	−4.3 (5)	C1—N1—Zn1—Zn1ⁱ	142.2 (2)
C9—C8—C13—C12	−1.3 (6)	C6—N2—Zn1—O4	−51.9 (8)
C7—C8—C13—C12	176.3 (3)	C7ⁱ—N2—Zn1—O4	69.3 (8)
C11—C12—C14—N1	140.1 (4)	C6—N2—Zn1—O4ⁱ	−120.7 (2)
C13—C12—C14—N1	−40.9 (7)	C7ⁱ—N2—Zn1—O4ⁱ	0.5 (2)
C11—C10—C15—C18	−2.3 (6)	C6—N2—Zn1—N1	−9.4 (2)
C9—C10—C15—C18	176.8 (4)	C7ⁱ—N2—Zn1—N1	111.8 (3)
C11—C10—C15—C16	−121.6 (5)	C6—N2—Zn1—O2	91.3 (3)
C9—C10—C15—C16	57.5 (5)	C7ⁱ—N2—Zn1—O2	−147.6 (2)
C11—C10—C15—C17	120.4 (4)	C6—N2—Zn1—O1	147.1 (2)
C9—C10—C15—C17	−60.5 (6)	C7ⁱ—N2—Zn1—O1	−91.7 (2)
C12—C14—N1—C1	−166.4 (4)	C6—N2—Zn1—Zn1ⁱ	−112.0 (2)
C12—C14—N1—Zn1	61.4 (5)	C7ⁱ—N2—Zn1—Zn1ⁱ	9.2 (3)
C2—C1—N1—C14	40.4 (6)	N3—O2—Zn1—O4	−88.6 (2)
C6—C1—N1—C14	−139.5 (4)	N3—O2—Zn1—O4ⁱ	2.0 (3)
C2—C1—N1—Zn1	173.0 (3)	N3—O2—Zn1—N1	−180.0 (2)
C6—C1—N1—Zn1	−6.9 (5)	N3—O2—Zn1—N2	97.5 (2)
C5—C6—N2—C7ⁱ	66.3 (5)	N3—O2—Zn1—O1	−1.0 (2)
C1—C6—N2—C7ⁱ	−111.5 (4)	N3—O2—Zn1—Zn1ⁱ	−60.0 (3)
C5—C6—N2—Zn1	−173.5 (3)	N3—O1—Zn1—O4	99.0 (2)
C1—C6—N2—Zn1	8.7 (4)	N3—O1—Zn1—O4ⁱ	−177.4 (2)
O3—N3—O1—Zn1	−179.5 (4)	N3—O1—Zn1—N1	3.5 (5)
O2—N3—O1—Zn1	−1.7 (4)	N3—O1—Zn1—N2	−84.3 (2)
O3—N3—O2—Zn1	179.5 (3)	N3—O1—Zn1—O2	1.0 (2)
O1—N3—O2—Zn1	1.7 (4)	N3—O1—Zn1—Zn1ⁱ	141.1 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₃₆H₄₂N₄O₂)(NO₃)₂]
M_r	817.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.7149 (8), 18.0691 (10), 7.3523 (3)
β (°)	101.110 (5)
V (Å³)	1787.87 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.40
Crystal size (mm)	0.45 × 0.25 × 0.20

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.661, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	15034, 4340, 1698
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.065, 0.91
No. of reflections	4340
No. of parameters	241
No. of restraints	357
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.45

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—N1	2.081 (4)	Zn1—O2	2.243 (3)
Zn1—N2	2.102 (3)	Zn1—O4	2.019 (2)
Zn1—O1	2.264 (3)	Zn1—O4ⁱ	2.043 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05–0320), the Fok Ying Tung Education Foundation and the Analysis and Testing Foundation of Northeast Normal University for support.

References

Bazzicalupi, C., Bencini, A., Bianchi, A., Fusi, V., Giorgi, C., Paoletti, P., Valtancoli, B. & Zanchi, D. (1997). Inorg. Chem. 36, 2784–2790. CSD CrossRef PubMed CAS Web of Science Google Scholar
Burley, S. K., David, P. R., Taylor, A. & Lipscomb, W. N. (1990). Proc. Natl. Acad. Sci. USA, 87, 6878–6882. CrossRef CAS PubMed Web of Science Google Scholar
Dutta, B., Bag, P., Flörke, U. & Nag, K. (2005). Inorg. Chem. 44,147–157. Web of Science CSD CrossRef PubMed CAS Google Scholar
Fan, L.-J., Ma, J.-F. & Liu, J. (2009). Acta Cryst. E65, m777–m778. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lipscomb, W. N. & Straeter, N. (1996). Chem. Rev. 96, 2375–2434. CrossRef PubMed CAS Web of Science Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Roderick, S. & Mathews, B. W. (1993). Biochemistry, 32, 3907–3912. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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