μ-Actetato-1:2κ2O:O′-tribromido-2κ3Br-(5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-1,7-diene-1κ4N)dizinc(II)

Li, H.F.; Shi, F.F.; Rong, R.

doi:10.1107/S1600536810033702

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1338

doi:10.1107/S1600536810033702

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μ-Actetato-1:2κ²O:O′-tribromido-2κ³Br-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradeca-1,7-diene-1κ⁴N)dizinc(II)

HuaFeng Li,^a FeiFei Shi ^a ^* and Rong Rong ^b

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and ^bDepartment of Chemistry, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 5 June 2010; accepted 20 August 2010; online 30 September 2010)

In the title compound, [Zn₂Br₃(CH₃COO)(C₁₆H₃₂N₄)], one Zn^II atom has a distorted square-planar coordination formed by the four macrocyclic N atoms with an acetate O atom in the apical position and the other Zn^II atom has a tetrahedral coordination environment formed by three Br atoms and one O acetate atom. The two Zn^II atoms are linked by an acetate bridge. In the crystal, molecules are linked into centrosymmetric dimers with graph-set motifs R₂²(16) by an N—H⋯Br interaction. The molecular configuration is stabilized by an intramolecular N—H⋯Br hydrogen bond.

Related literature

For related macrocyclic complexes, see: Whimp et al. (1970 ); Yang (2005 ); Tebbe et al. (1985 ). The unsubstituted parent compound exists in the zwitterionic form, see: Spirlet et al. (1991 ); Maurya et al. (1991 ). For the preparation of the precursor complex C₁₆H₃₂N₄·2HBr·2H₂O, see: Hay et al. (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Zn₂Br₃(C₂H₃O₂)(C₁₆H₃₂N₄)]
M_r = 709.97
Monoclinic, P 2₁ /n
a = 10.2964 (8) Å
b = 13.6985 (13) Å
c = 18.5235 (18) Å
β = 92.280 (1)°
V = 2610.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 6.45 mm⁻¹
T = 298 K
0.43 × 0.42 × 0.22 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.240, T_max = 0.428
13032 measured reflections
4608 independent reflections
2923 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.067
S = 0.88
4608 reflections
269 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Br2ⁱ	0.91	2.80	3.549 (3)	140
N1—H1⋯Br1	0.91	2.74	3.641 (3)	171
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536810033702/bx2283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810033702/bx2283Isup2.hkl

checkCIF report

Comment top

The structures of several related macrocyclic complexes have been reported (Whimp et al., 1970; Yang, 2005; Tebbe et al., 1985). The unsubstituted parent compound exists in the zwitterionic form (Maurya et al., 1991; Spirlet et al., 1991). The zinc teraazamacrocyclic complex cation, [Zn(C₁₆H₃₂N₄)] ²⁺, can combine with different anions to form many kinds of structures.

We herein report the crystal structure of a new compound synthesized by reaction of Zn(CH₃COO)₂.2H₂O and the complex C₁₈H₃₂N₄.2HBr.2H₂O, Fig.1. The structural analysis reveals that the title complex is formed by a discrete neutral dinuclear C₁₈H₃₅N₄O₂Br₃Zn₂ molecule consisting of two Zn atoms bridged by an acetate with the distance of 6.512 (1) Å between the them. Zn(1) is five-coordinated by the four macrocyclic N atoms with acetate O atom as an apical ligand while that the other Zn atom is in a tetrahedron coordinate environment formed by three bromine atoms and one O acetate atom. The average Zn—N(amine) bond distance of 2.1546 (5)Å and Zn—N(imine) bond distance of 2.0582 (5) Å). The average Zn—Br bond distance of 2.4070 (6) Å, the Zn(1)—O(1) bond distance of` 2.0030 (1) Å and the Zn(2)—O(2) bond distance of` 1.9967 (1) Å). In the crystal the molecules are linked into centrosymmetric dimers with graph-set notation R²₂(16) motifs by a N—H···Br interaction, centred at [1/2,1/2,0] (Bernstein et al., 1995), Fig. 2. The molecular conformation is stabilized by one intramolecular N—H···Br hydrogen bond. Table 1.

Related literature top

For related macrocyclic complexes, see: Whimp et al. (1970); Yang (2005); Tebbe et al. (1985). The unsubstituted parent compound exists in the zwitterionic form, see: Spirlet et al. (1991); Maurya et al. (1991). The precursor complex C₁₈H₃₂N₄.2HBr.2H₂O was prepared by the literature method, see: Hay et al. (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

All chemicals were of reagent grade and were used as received without further purification. The precursor complex C₁₈H₃₂N₄.2HBr.2H₂O was prepared by the literature method (Hay et al.,1975). To a 10 ml me thanol solution of Zn(CH₃COO)₂.2H₂O(0.2 mmol,0.039 g), a 5 ml methanol solution of C₁₈H₃₂N₄.2HBr.2H₂O (0.2 mmol,0.0957 g) was added dropwise with stirring. The resulting solution was continuously stirred for about 30 min. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature over several days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 asymmetric structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

µ-Actetato-1:2κ²O:O'-tribromido-2κ³Br- (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradeca-1,7-diene- 1κ⁴N)dizinc(II) top

Crystal data top

[Zn₂Br₃(C₂H₃O₂)(C₁₆H₃₂N₄)]	F(000) = 1408
M_r = 709.97	D_x = 1.806 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3476 reflections
a = 10.2964 (8) Å	θ = 2.3–27.5°
b = 13.6985 (13) Å	µ = 6.45 mm⁻¹
c = 18.5235 (18) Å	T = 298 K
β = 92.280 (1)°	Prism, purple
V = 2610.6 (4) Å³	0.43 × 0.42 × 0.22 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	4608 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
thin–slice ω scans	h = −12→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→14
T_min = 0.240, T_max = 0.428	l = −22→17
13032 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0294P)²] where P = (F_o² + 2F_c²)/3
4608 reflections	(Δ/σ)_max = 0.001
269 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Zn₂Br₃(C₂H₃O₂)(C₁₆H₃₂N₄)]	V = 2610.6 (4) Å³
M_r = 709.97	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2964 (8) Å	µ = 6.45 mm⁻¹
b = 13.6985 (13) Å	T = 298 K
c = 18.5235 (18) Å	0.43 × 0.42 × 0.22 mm
β = 92.280 (1)°

Data collection top

Rigaku SCXmini diffractometer	4608 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2923 reflections with I > 2σ(I)
T_min = 0.240, T_max = 0.428	R_int = 0.038
13032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 0.88	Δρ_max = 0.57 e Å⁻³
4608 reflections	Δρ_min = −0.55 e Å⁻³
269 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	0.41999 (5)	0.72812 (3)	0.14536 (3)	0.03733 (14)
Zn2	0.62870 (5)	0.70274 (3)	−0.07545 (3)	0.04247 (15)
Br1	0.76873 (5)	0.82052 (4)	−0.01332 (3)	0.05506 (16)
Br2	0.72235 (6)	0.62875 (4)	−0.18003 (3)	0.06807 (19)
Br3	0.43184 (6)	0.78165 (4)	−0.11309 (3)	0.07402 (19)
N1	0.5700 (3)	0.8386 (2)	0.14436 (19)	0.0423 (9)
H1	0.6128	0.8291	0.1029	0.051*
N2	0.4572 (4)	0.6965 (3)	0.25310 (19)	0.0469 (10)
N3	0.2615 (3)	0.6280 (2)	0.15567 (17)	0.0368 (9)
H3	0.2904	0.5687	0.1411	0.044*
N4	0.3048 (4)	0.8384 (2)	0.10354 (19)	0.0432 (10)
O1	0.5078 (3)	0.6609 (2)	0.06459 (16)	0.0492 (8)
O2	0.6337 (3)	0.58620 (19)	−0.01065 (15)	0.0505 (9)
C1	0.6712 (5)	0.8346 (4)	0.2045 (3)	0.0527 (13)
C2	0.6081 (5)	0.8285 (4)	0.2784 (2)	0.0676 (16)
H2A	0.6758	0.8394	0.3154	0.081*
H2B	0.5472	0.8823	0.2811	0.081*
C3	0.5369 (5)	0.7362 (4)	0.2978 (3)	0.0594 (14)
C4	0.5646 (5)	0.6981 (5)	0.3728 (3)	0.096 (2)
H4A	0.4887	0.7057	0.4008	0.144*
H4B	0.6355	0.7341	0.3951	0.144*
H4C	0.5873	0.6303	0.3705	0.144*
C5	0.7534 (5)	0.7430 (4)	0.1919 (3)	0.0635 (15)
H5A	0.6994	0.6861	0.1941	0.095*
H5B	0.8218	0.7389	0.2285	0.095*
H5C	0.7904	0.7468	0.1452	0.095*
C6	0.7621 (5)	0.9236 (4)	0.2029 (3)	0.0804 (18)
H6A	0.7923	0.9320	0.1550	0.121*
H6B	0.8351	0.9134	0.2360	0.121*
H6C	0.7157	0.9809	0.2168	0.121*
C7	0.3741 (5)	0.6141 (3)	0.2740 (2)	0.0548 (14)
H7A	0.3624	0.6157	0.3257	0.066*
H7B	0.4157	0.5528	0.2624	0.066*
C8	0.2441 (5)	0.6206 (3)	0.2345 (2)	0.0477 (12)
H8A	0.1930	0.5631	0.2448	0.057*
H8B	0.1976	0.6775	0.2510	0.057*
C9	0.1416 (4)	0.6503 (3)	0.1099 (3)	0.0465 (12)
C10	0.0989 (4)	0.7575 (3)	0.1209 (3)	0.0515 (13)
H10A	0.0130	0.7649	0.0981	0.062*
H10B	0.0899	0.7674	0.1723	0.062*
C11	0.1824 (5)	0.8391 (3)	0.0939 (2)	0.0453 (12)
C12	0.1073 (5)	0.9219 (3)	0.0586 (3)	0.0803 (19)
H12A	0.1603	0.9795	0.0590	0.121*
H12B	0.0302	0.9342	0.0847	0.121*
H12C	0.0834	0.9047	0.0096	0.121*
C13	0.1742 (5)	0.6312 (3)	0.0316 (2)	0.0619 (15)
H13A	0.2465	0.6711	0.0191	0.093*
H13B	0.1003	0.6467	0.0005	0.093*
H13C	0.1963	0.5636	0.0259	0.093*
C14	0.0265 (5)	0.5847 (3)	0.1298 (3)	0.0669 (15)
H14A	0.0518	0.5174	0.1268	0.100*
H14B	−0.0460	0.5967	0.0969	0.100*
H14C	0.0023	0.5991	0.1782	0.100*
C15	0.3888 (5)	0.9187 (3)	0.0800 (3)	0.0567 (14)
H15A	0.3389	0.9786	0.0756	0.068*
H15B	0.4227	0.9036	0.0332	0.068*
C16	0.4994 (5)	0.9317 (3)	0.1349 (3)	0.0626 (15)
H16A	0.5581	0.9818	0.1188	0.075*
H16B	0.4657	0.9522	0.1807	0.075*
C17	0.5813 (5)	0.5924 (3)	0.0502 (2)	0.0380 (11)
C18	0.6139 (5)	0.5127 (3)	0.1038 (2)	0.0585 (14)
H18A	0.5482	0.5100	0.1391	0.088*
H18B	0.6966	0.5262	0.1274	0.088*
H18C	0.6177	0.4513	0.0790	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0313 (3)	0.0354 (3)	0.0452 (3)	0.0023 (2)	0.0018 (2)	−0.0006 (2)
Zn2	0.0463 (4)	0.0369 (3)	0.0442 (3)	−0.0020 (3)	0.0017 (3)	0.0035 (2)
Br1	0.0495 (4)	0.0584 (3)	0.0572 (3)	−0.0164 (3)	0.0010 (2)	−0.0022 (3)
Br2	0.1039 (5)	0.0423 (3)	0.0601 (3)	0.0021 (3)	0.0300 (3)	0.0018 (3)
Br3	0.0596 (4)	0.0683 (4)	0.0919 (4)	0.0104 (3)	−0.0254 (3)	0.0014 (3)
N1	0.032 (2)	0.045 (2)	0.050 (2)	−0.0014 (18)	0.0042 (19)	−0.0088 (18)
N2	0.043 (3)	0.055 (3)	0.042 (2)	0.000 (2)	0.001 (2)	−0.006 (2)
N3	0.038 (2)	0.0321 (19)	0.040 (2)	0.0040 (17)	0.0038 (18)	−0.0003 (17)
N4	0.033 (3)	0.036 (2)	0.060 (3)	0.0012 (18)	0.004 (2)	0.0044 (18)
O1	0.043 (2)	0.0449 (19)	0.060 (2)	0.0045 (16)	0.0063 (16)	−0.0063 (16)
O2	0.067 (3)	0.0379 (18)	0.048 (2)	0.0049 (16)	0.0190 (18)	0.0034 (15)
C1	0.032 (3)	0.067 (3)	0.058 (3)	−0.012 (3)	0.001 (3)	−0.020 (3)
C2	0.054 (4)	0.093 (4)	0.056 (3)	−0.008 (3)	−0.001 (3)	−0.029 (3)
C3	0.039 (3)	0.092 (4)	0.048 (3)	0.003 (3)	0.009 (3)	−0.022 (3)
C4	0.069 (5)	0.181 (7)	0.038 (3)	−0.027 (4)	−0.007 (3)	0.004 (4)
C5	0.040 (3)	0.094 (4)	0.056 (3)	0.012 (3)	−0.005 (3)	−0.007 (3)
C6	0.052 (4)	0.099 (4)	0.089 (4)	−0.032 (3)	0.000 (3)	−0.024 (4)
C7	0.067 (4)	0.055 (3)	0.043 (3)	−0.003 (3)	0.002 (3)	0.000 (2)
C8	0.051 (4)	0.045 (3)	0.048 (3)	−0.003 (2)	0.016 (3)	−0.003 (2)
C9	0.033 (3)	0.036 (3)	0.071 (4)	−0.002 (2)	0.000 (3)	0.003 (2)
C10	0.032 (3)	0.044 (3)	0.079 (4)	0.009 (2)	0.002 (3)	0.006 (2)
C11	0.040 (3)	0.036 (3)	0.060 (3)	0.001 (2)	−0.001 (3)	−0.004 (2)
C12	0.056 (4)	0.043 (3)	0.139 (5)	0.003 (3)	−0.042 (4)	0.017 (3)
C13	0.069 (4)	0.055 (3)	0.061 (4)	0.002 (3)	−0.016 (3)	−0.004 (3)
C14	0.042 (4)	0.052 (3)	0.107 (4)	−0.010 (3)	−0.001 (3)	0.008 (3)
C15	0.045 (4)	0.037 (3)	0.088 (4)	0.000 (2)	0.002 (3)	0.016 (3)
C16	0.049 (4)	0.039 (3)	0.100 (4)	−0.006 (3)	0.009 (3)	−0.004 (3)
C17	0.042 (3)	0.033 (3)	0.039 (3)	−0.011 (2)	0.000 (2)	−0.001 (2)
C18	0.079 (4)	0.046 (3)	0.051 (3)	0.000 (3)	0.004 (3)	0.008 (2)

Geometric parameters (Å, º) top

Zn1—O1	2.003 (3)	C6—H6A	0.9600
Zn1—N4	2.053 (3)	C6—H6B	0.9600
Zn1—N2	2.063 (4)	C6—H6C	0.9600
Zn1—N3	2.146 (3)	C7—C8	1.502 (6)
Zn1—N1	2.163 (3)	C7—H7A	0.9700
Zn2—O2	1.997 (3)	C7—H7B	0.9700
Zn2—Br3	2.3772 (8)	C8—H8A	0.9700
Zn2—Br2	2.4204 (7)	C8—H8B	0.9700
Zn2—Br1	2.4236 (7)	C9—C13	1.524 (6)
N1—C16	1.474 (5)	C9—C14	1.543 (6)
N1—C1	1.497 (5)	C9—C10	1.548 (6)
N1—H1	0.9100	C10—C11	1.508 (6)
N2—C3	1.264 (6)	C10—H10A	0.9700
N2—C7	1.479 (5)	C10—H10B	0.9700
N3—C8	1.482 (5)	C11—C12	1.508 (6)
N3—C9	1.501 (5)	C12—H12A	0.9600
N3—H3	0.9100	C12—H12B	0.9600
N4—C11	1.266 (5)	C12—H12C	0.9600
N4—C15	1.476 (5)	C13—H13A	0.9600
O1—C17	1.241 (5)	C13—H13B	0.9600
O2—C17	1.272 (5)	C13—H13C	0.9600
C1—C5	1.537 (6)	C14—H14A	0.9600
C1—C6	1.538 (6)	C14—H14B	0.9600
C1—C2	1.539 (6)	C14—H14C	0.9600
C2—C3	1.512 (7)	C15—C16	1.507 (6)
C2—H2A	0.9700	C15—H15A	0.9700
C2—H2B	0.9700	C15—H15B	0.9700
C3—C4	1.501 (7)	C16—H16A	0.9700
C4—H4A	0.9600	C16—H16B	0.9700
C4—H4B	0.9600	C17—C18	1.504 (5)
C4—H4C	0.9600	C18—H18A	0.9600
C5—H5A	0.9600	C18—H18B	0.9600
C5—H5B	0.9600	C18—H18C	0.9600
C5—H5C	0.9600

O1—Zn1—N4	109.13 (13)	H6B—C6—H6C	109.5
O1—Zn1—N2	123.65 (13)	N2—C7—C8	109.9 (4)
N4—Zn1—N2	126.98 (14)	N2—C7—H7A	109.7
O1—Zn1—N3	98.04 (12)	C8—C7—H7A	109.7
N4—Zn1—N3	94.26 (14)	N2—C7—H7B	109.7
N2—Zn1—N3	83.84 (14)	C8—C7—H7B	109.7
O1—Zn1—N1	88.39 (12)	H7A—C7—H7B	108.2
N4—Zn1—N1	83.31 (14)	N3—C8—C7	110.1 (4)
N2—Zn1—N1	92.85 (14)	N3—C8—H8A	109.6
N3—Zn1—N1	173.56 (13)	C7—C8—H8A	109.6
O2—Zn2—Br3	122.76 (10)	N3—C8—H8B	109.6
O2—Zn2—Br2	98.32 (8)	C7—C8—H8B	109.6
Br3—Zn2—Br2	108.54 (3)	H8A—C8—H8B	108.2
O2—Zn2—Br1	104.25 (9)	N3—C9—C13	107.2 (4)
Br3—Zn2—Br1	108.71 (3)	N3—C9—C14	111.6 (4)
Br2—Zn2—Br1	114.23 (3)	C13—C9—C14	109.1 (4)
C16—N1—C1	116.5 (4)	N3—C9—C10	110.5 (4)
C16—N1—Zn1	104.9 (3)	C13—C9—C10	111.3 (4)
C1—N1—Zn1	116.4 (3)	C14—C9—C10	107.2 (4)
C16—N1—H1	106.1	C11—C10—C9	119.4 (4)
C1—N1—H1	106.1	C11—C10—H10A	107.5
Zn1—N1—H1	106.1	C9—C10—H10A	107.5
C3—N2—C7	121.6 (4)	C11—C10—H10B	107.5
C3—N2—Zn1	129.4 (4)	C9—C10—H10B	107.5
C7—N2—Zn1	109.1 (3)	H10A—C10—H10B	107.0
C8—N3—C9	116.2 (4)	N4—C11—C10	121.7 (4)
C8—N3—Zn1	104.7 (2)	N4—C11—C12	123.9 (4)
C9—N3—Zn1	115.5 (2)	C10—C11—C12	114.3 (4)
C8—N3—H3	106.6	C11—C12—H12A	109.5
C9—N3—H3	106.6	C11—C12—H12B	109.5
Zn1—N3—H3	106.6	H12A—C12—H12B	109.5
C11—N4—C15	123.0 (4)	C11—C12—H12C	109.5
C11—N4—Zn1	127.9 (3)	H12A—C12—H12C	109.5
C15—N4—Zn1	108.9 (3)	H12B—C12—H12C	109.5
C17—O1—Zn1	143.7 (3)	C9—C13—H13A	109.5
C17—O2—Zn2	118.5 (3)	C9—C13—H13B	109.5
N1—C1—C5	106.7 (3)	H13A—C13—H13B	109.5
N1—C1—C6	111.3 (4)	C9—C13—H13C	109.5
C5—C1—C6	107.8 (4)	H13A—C13—H13C	109.5
N1—C1—C2	110.9 (4)	H13B—C13—H13C	109.5
C5—C1—C2	110.2 (4)	C9—C14—H14A	109.5
C6—C1—C2	109.8 (4)	C9—C14—H14B	109.5
C3—C2—C1	118.8 (4)	H14A—C14—H14B	109.5
C3—C2—H2A	107.6	C9—C14—H14C	109.5
C1—C2—H2A	107.6	H14A—C14—H14C	109.5
C3—C2—H2B	107.6	H14B—C14—H14C	109.5
C1—C2—H2B	107.6	N4—C15—C16	108.9 (4)
H2A—C2—H2B	107.0	N4—C15—H15A	109.9
N2—C3—C4	123.5 (5)	C16—C15—H15A	109.9
N2—C3—C2	120.8 (5)	N4—C15—H15B	109.9
C4—C3—C2	115.7 (4)	C16—C15—H15B	109.9
C3—C4—H4A	109.5	H15A—C15—H15B	108.3
C3—C4—H4B	109.5	N1—C16—C15	109.5 (4)
H4A—C4—H4B	109.5	N1—C16—H16A	109.8
C3—C4—H4C	109.5	C15—C16—H16A	109.8
H4A—C4—H4C	109.5	N1—C16—H16B	109.8
H4B—C4—H4C	109.5	C15—C16—H16B	109.8
C1—C5—H5A	109.5	H16A—C16—H16B	108.2
C1—C5—H5B	109.5	O1—C17—O2	121.7 (4)
H5A—C5—H5B	109.5	O1—C17—C18	121.9 (4)
C1—C5—H5C	109.5	O2—C17—C18	116.4 (4)
H5A—C5—H5C	109.5	C17—C18—H18A	109.5
H5B—C5—H5C	109.5	C17—C18—H18B	109.5
C1—C6—H6A	109.5	H18A—C18—H18B	109.5
C1—C6—H6B	109.5	C17—C18—H18C	109.5
H6A—C6—H6B	109.5	H18A—C18—H18C	109.5
C1—C6—H6C	109.5	H18B—C18—H18C	109.5
H6A—C6—H6C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Br2ⁱ	0.91	2.80	3.549 (3)	140
N1—H1···Br1	0.91	2.74	3.641 (3)	171

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Zn₂Br₃(C₂H₃O₂)(C₁₆H₃₂N₄)]
M_r	709.97
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.2964 (8), 13.6985 (13), 18.5235 (18)
β (°)	92.280 (1)
V (Å³)	2610.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.45
Crystal size (mm)	0.43 × 0.42 × 0.22

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.240, 0.428
No. of measured, independent and observed [I > 2σ(I)] reflections	13032, 4608, 2923
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.067, 0.88
No. of reflections	4608
No. of parameters	269
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.55

Computer programs: CrystalClear (Rigaku, 2005), 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
N3—H3···Br2ⁱ	0.91	2.80	3.549 (3)	140.0
N1—H1···Br1	0.91	2.74	3.641 (3)	171.2

Symmetry code: (i) −x+1, −y+1, −z.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573 CrossRef CAS Web of Science Google Scholar
Hay, R. W., Lawrance, A. G. & Curtis, N. F. (1975). J. Chem. Soc. Perkin Trans. pp. 591–593. CrossRef Web of Science Google Scholar
Maurya, M. R., Zaluzec, E. J. & Pavkovic, S. F. (1991). Inorg. Chem. 30, 3657–3662. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spirlet, M. R., Rebizant, J. & Barthelemy, P. P. (1991). J. Chem. Soc. Dalton Trans. pp. 2477–2481. CSD CrossRef Web of Science Google Scholar
Tebbe, K.-F., Heinlein, T. & Fehér, M. (1985). Z. Kristallogr. 172 89–95. CrossRef CAS Web of Science Google Scholar
Whimp, P. O., Bailey, M. F. & Curtis, N. F. (1970). J. Chem. Soc. A, pp. 1956–1963. CSD CrossRef Google Scholar
Yang, Y.-M. (2005). Acta Cryst. E61, m1618–m1619. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page m1338

doi:10.1107/S1600536810033702

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