[μ-14,29-Di-tert-butyl-3,10,18,25-tetra-azatpenta-cyclo-[25.3.1.1.0.0]dotriaconta-1(31),4,6,8,12(32),14,16,19,21,23,27,29-dodeca-ene-31,32-diol-ato]bis-[(nitrato-κO,O')zinc(II)].

In the title centrosymmetric dinuclear zinc(II) complex, [Zn(2)(C(36)H(42)N(4)O(2))(NO(3))(2)], the Zn(II) atom has a distorted octa-hedral 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 Zn(2)O(2) 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 = 817.20

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.065

S = 0.91

4340 reflections

241 parameters

357 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028530/hy2213sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn2(C36H42N4O2)(NO3)2]	F(000) = 848
Mr = 817.20	Dx = 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

Oxford Diffraction Gemini R Ultra diffractometer	4340 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
graphite	Rint = 0.099
Detector resolution: 10.0 pixels mm-1	θmax = 29.3°, θmin = 1.9°
ω scans	h = −16→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −24→24
Tmin = 0.661, Tmax = 0.752	l = −8→10
15034 measured reflections

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(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3
4340 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.66 e Å−3
357 restraints	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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) .