(μ-Ethane-1,2-diamine-κ2N:N′)bis­[bis­(ethane-1,2-diamine-κ2N,N′)zinc(II)] tetra­kis­(perchlorate)

Ding, M.-H.; Ng, S.W.

doi:10.1107/S1600536810038730

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1356

https://doi.org/10.1107/S1600536810038730

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(μ-Ethane-1,2-diamine-κ²N:N′)bis[bis(ethane-1,2-diamine-κ²N,N′)zinc(II)] tetrakis(perchlorate)

Man-Hua Ding ^a and Seik Weng Ng ^b ^*

^aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 September 2010; accepted 28 September 2010; online 2 October 2010)

In the title salt, [Zn₂(C₂H₈N₂)₅](ClO₄)₄, an ethylenediamine molecule bridges two bis(ethylenediamine)zinc units; the five-coordinate Zn atoms show a trigonal–bipyramidal coordination geometry that is distorted towards square-pyramidal (that of one Zn atom is distorted by 12% and that of the other by 34%). The perchlorate ions are all disordered over two positions in a 1:1 ratio. The cation interacts weakly with the anion by N—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For other μ-(ethylenediamine)bis[bis(ethylenediamine)zinc(II)] salts, see: Khan et al. (2003 ); Natarajan et al. (2006 ); Qi et al. (2007 ).

Experimental

Crystal data

[Zn₂(C₂H₈N₂)₅](ClO₄)₄
M_r = 829.06
Monoclinic, P 2₁ /n
a = 15.6297 (8) Å
b = 14.3133 (7) Å
c = 15.6811 (8) Å
β = 119.636 (1)°
V = 3049.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.01 mm⁻¹
T = 248 K
0.45 × 0.40 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.711, T_max = 1.000
14146 measured reflections
6543 independent reflections
4259 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.186
S = 1.05
6543 reflections
535 parameters
293 restraints
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H12⋯O1	0.86	1.93	2.790 (9)	174
N1—H13⋯O8′	0.86	2.22	3.066 (12)	169
N3—H32⋯O12	0.86	2.34	3.018 (7)	136
N3—H32⋯O12′	0.86	2.29	3.070 (10)	152
N4—H41⋯O7ⁱ	0.86	2.35	3.157 (12)	156
N4—H41⋯O7′ⁱ	0.86	2.08	2.885 (9)	156
N4—H42⋯O16′	0.86	2.12	2.973 (8)	175
N5—H51⋯O1	0.86	2.30	3.120 (15)	159
N6—H62⋯O2	0.86	2.29	3.034 (11)	146
N7—H71⋯O2	0.86	2.32	3.163 (10)	168
N7—H71⋯O2′	0.86	2.22	3.018 (10)	154
N7—H74⋯O6ⁱⁱ	0.86	2.35	3.143 (11)	154
N7—H74⋯O6′ⁱⁱ	0.86	2.36	3.210 (9)	172
N8—H81⋯O11ⁱⁱ	0.86	2.26	3.075 (8)	157
N8—H81⋯O11′ⁱⁱ	0.86	2.29	3.148 (12)	177
N10—H102⋯O3ⁱ	0.86	2.17	2.929 (9)	146
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810038730/hg2718sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038730/hg2718Isup2.hkl

checkCIF report

Comment top

The zinc(II) cation furnishes a number of compounds with ethylenediamine, and there are serveral salts having the atom chelated by either two or three of the ligands. There is a much smaller number of compounds having the ligand behaving in a bridging mode, and the title zinc perchlorate complex (Scheme I) is an unusual example of a 1:1.5 adduct. µ-(Ethane-1,2-diamine)-bis[bis(ethane-1,2-diamine)zinc(II)] tetrakisperchlorate (Fig. 1) which is a dinuclear compound with the metal atoms in a five-coordinate environment. The geometries are both trigonal bipyramidal,but one is distorted towards a square pyramid 12% and whereas the other is distorted by 34% (along the Berry pseudorotation pathway). The perchlorate anions are only weakly linked to the dinuclear unit by hydrogen bonds; the anions are all disordered in their oxygen atoms.

Other µ-(ethylenediamine)-bis[bis(ethylenediamine)zinc(II)] tetracations have been reported, but the counterions are the extremely large polyoxometallate counterions (Khan et al., 2003; Natarajan et al., 2006; Qi et al., 2007).

Related literature top

For other µ-(ethylenediamine)bis[bis(ethylenediamine)zinc(II)] salts, see: Khan et al. (2003); Natarajan et al. (2006); Qi et al. (2007).

Experimental top

A methanol solution (10 ml) of diaminoethane (1.20 g, 0.02 mol) was added to a methanol solution (50 ml) of zinc acetate (2.48 g, 0.01 mol). The mixture was filtered, and to the solution was added an aqueous solution of sodium perchlorate (2.44 g, 0.02 mol). After several days, colorless crystals were separated from solution.

Structure description top

For other µ-(ethylenediamine)bis[bis(ethylenediamine)zinc(II)] salts, see: Khan et al. (2003); Natarajan et al. (2006); Qi et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Zn₂(C₂H₈N₂)₅] 4[ClO₄] the 50% probability level; hydrogen atoms are shown as spheres of arbitrary radius. The disorder in the ethylenediamine perchlorate parts is not shown.

(µ-Ethane-1,2-diamine-κ²N:N')bis[bis(ethane-1,2-diamine-κ²N,N')zinc(II)] tetrakis(perchlorate) top

Crystal data top

[Zn₂(C₂H₈N₂)₅](ClO₄)₄	F(000) = 1704
M_r = 829.06	D_x = 1.806 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4985 reflections
a = 15.6297 (8) Å	θ = 2.6–26.9°
b = 14.3133 (7) Å	µ = 2.01 mm⁻¹
c = 15.6811 (8) Å	T = 248 K
β = 119.636 (1)°	Prism, colorless
V = 3049.1 (3) Å³	0.45 × 0.40 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	6543 independent reflections
Radiation source: fine-focus sealed tube	4259 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 27.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→17
T_min = 0.711, T_max = 1.000	k = −18→17
14146 measured reflections	l = −20→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1053P)² + 3.3033P] where P = (F_o² + 2F_c²)/3
6543 reflections	(Δ/σ)_max = 0.001
535 parameters	Δρ_max = 1.06 e Å⁻³
293 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Zn₂(C₂H₈N₂)₅](ClO₄)₄	V = 3049.1 (3) Å³
M_r = 829.06	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.6297 (8) Å	µ = 2.01 mm⁻¹
b = 14.3133 (7) Å	T = 248 K
c = 15.6811 (8) Å	0.45 × 0.40 × 0.10 mm
β = 119.636 (1)°

Data collection top

Bruker SMART APEX diffractometer	6543 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4259 reflections with I > 2σ(I)
T_min = 0.711, T_max = 1.000	R_int = 0.029
14146 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	293 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.05	Δρ_max = 1.06 e Å⁻³
6543 reflections	Δρ_min = −0.83 e Å⁻³
535 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.30084 (4)	0.63583 (4)	0.51082 (4)	0.03254 (19)
Zn2	0.33807 (4)	0.63741 (4)	0.06722 (4)	0.0331 (2)
Cl1	0.60325 (9)	0.61482 (11)	0.44862 (11)	0.0460 (4)
Cl2	0.56091 (10)	0.60846 (13)	0.89575 (12)	0.0568 (4)
Cl3	0.31237 (11)	0.85357 (11)	0.78206 (11)	0.0503 (4)
Cl4	0.12173 (11)	0.43344 (11)	0.18233 (13)	0.0558 (4)
O1	0.5436 (10)	0.6079 (13)	0.4913 (11)	0.166 (8)	0.50
O2	0.5520 (8)	0.5753 (7)	0.3528 (5)	0.096 (4)	0.50
O3	0.6263 (10)	0.7073 (5)	0.4396 (12)	0.134 (6)	0.50
O4	0.6906 (7)	0.5627 (9)	0.5042 (10)	0.064 (5)	0.50
O5	0.6386 (7)	0.5439 (7)	0.9279 (10)	0.067 (4)	0.50
O6	0.5554 (11)	0.6492 (11)	0.9740 (8)	0.147 (7)	0.50
O7	0.5853 (8)	0.6838 (6)	0.8500 (9)	0.101 (4)	0.50
O8	0.4708 (6)	0.5706 (8)	0.8249 (7)	0.058 (4)	0.50
O9	0.3829 (8)	0.9031 (9)	0.7681 (10)	0.072 (5)	0.50
O10	0.2323 (5)	0.9136 (6)	0.7589 (8)	0.073 (3)	0.50
O11	0.3578 (8)	0.8256 (8)	0.8813 (4)	0.083 (3)	0.50
O12	0.2798 (7)	0.7759 (6)	0.7193 (7)	0.059 (3)	0.50
O13	0.0504 (7)	0.3625 (6)	0.1359 (8)	0.061 (3)	0.50
O14	0.1800 (7)	0.4358 (7)	0.1363 (7)	0.070 (3)	0.50
O15	0.0743 (7)	0.5201 (5)	0.1690 (11)	0.102 (4)	0.50
O16	0.1829 (8)	0.4167 (9)	0.2828 (4)	0.102 (4)	0.50
O1'	0.6889 (7)	0.5608 (9)	0.4831 (11)	0.066 (5)	0.50
O2'	0.5760 (11)	0.6527 (11)	0.3559 (6)	0.131 (5)	0.50
O3'	0.5263 (6)	0.5629 (6)	0.4472 (10)	0.087 (4)	0.50
O4'	0.6187 (8)	0.6913 (6)	0.5127 (7)	0.091 (4)	0.50
O5'	0.6431 (7)	0.5608 (8)	0.9030 (10)	0.068 (4)	0.50
O6'	0.5437 (8)	0.5684 (7)	0.9710 (6)	0.091 (4)	0.50
O7'	0.5763 (9)	0.7031 (4)	0.9143 (10)	0.111 (5)	0.50
O8'	0.4770 (8)	0.5879 (10)	0.8053 (6)	0.077 (5)	0.50
O9'	0.3966 (7)	0.9009 (10)	0.7969 (11)	0.079 (5)	0.50
O10'	0.2289 (8)	0.8949 (12)	0.7013 (10)	0.205 (10)	0.50
O11'	0.2965 (13)	0.8605 (11)	0.8627 (9)	0.133 (6)	0.50
O12'	0.3136 (12)	0.7583 (5)	0.7605 (12)	0.123 (7)	0.50
O13'	0.0736 (10)	0.3482 (6)	0.1748 (12)	0.121 (7)	0.50
O14'	0.2207 (5)	0.4184 (11)	0.2095 (14)	0.153 (7)	0.50
O15'	0.0743 (12)	0.4832 (12)	0.0934 (8)	0.187 (8)	0.50
O16'	0.1178 (12)	0.4898 (11)	0.2541 (11)	0.132 (5)	0.50
N1	0.4573 (3)	0.6420 (3)	0.6072 (4)	0.0443 (12)
H11	0.4756	0.5997	0.6518	0.053*	0.50
H12	0.4877	0.6332	0.5748	0.053*	0.50
H13	0.4718	0.6273	0.6660	0.053*	0.50
H14	0.4868	0.6040	0.5879	0.053*	0.50
N2	0.3132 (3)	0.7821 (3)	0.5284 (4)	0.0449 (11)
H21	0.2768	0.8101	0.4736	0.054*	0.50
H22	0.2970	0.8004	0.5707	0.054*	0.50
H23	0.2933	0.8076	0.4720	0.054*	0.50
H24	0.2752	0.8008	0.5500	0.054*	0.50
N3	0.2715 (3)	0.5914 (3)	0.6223 (3)	0.0409 (11)
H31	0.2914	0.5348	0.6389	0.049*
H32	0.3022	0.6264	0.6731	0.049*
N4	0.1433 (3)	0.6078 (4)	0.4212 (3)	0.0460 (12)
H41	0.1113	0.6595	0.4016	0.055*
H42	0.1321	0.5754	0.3705	0.055*
N5	0.3141 (4)	0.6054 (4)	0.3861 (3)	0.0468 (12)
H51	0.3748	0.5941	0.4041	0.056*
H52	0.2805	0.5562	0.3578	0.056*
N6	0.3390 (4)	0.6155 (4)	0.2026 (4)	0.0585 (15)
H61	0.3295	0.5571	0.2075	0.070*
H62	0.3966	0.6294	0.2500	0.070*
N7	0.4950 (3)	0.6368 (3)	0.1374 (3)	0.0377 (10)
H71	0.5199	0.6217	0.1982	0.045*	0.50
H72	0.5146	0.5971	0.1095	0.045*	0.50
H73	0.5194	0.5987	0.1862	0.045*	0.50
H74	0.5142	0.6202	0.0968	0.045*	0.50
N8	0.3566 (3)	0.7837 (3)	0.0730 (3)	0.0438 (11)
H81	0.3424	0.8051	0.0163	0.053*	0.50
H82	0.3189	0.8102	0.0913	0.053*	0.50
H83	0.3149	0.8081	0.0178	0.053*	0.50
H84	0.3464	0.8068	0.1179	0.053*	0.50
N9	0.3228 (3)	0.6115 (4)	−0.0745 (3)	0.0506 (13)
H91	0.3526	0.6543	−0.0884	0.061*
H92	0.3486	0.5585	−0.0746	0.061*
N10	0.1871 (3)	0.5977 (4)	−0.0105 (3)	0.0461 (12)
H101	0.1754	0.5579	0.0235	0.055*
H102	0.1507	0.6459	−0.0200	0.055*
C1	0.4788 (10)	0.7355 (6)	0.6515 (10)	0.058 (3)	0.50
H1A	0.5492	0.7498	0.6821	0.070*	0.50
H1B	0.4580	0.7412	0.7009	0.070*	0.50
C2	0.4179 (5)	0.7996 (11)	0.5634 (10)	0.055 (4)	0.50
H2A	0.4337	0.8652	0.5830	0.066*	0.50
H2B	0.4331	0.7867	0.5110	0.066*	0.50
C3	0.1651 (3)	0.5971 (5)	0.5848 (4)	0.0490 (15)
H3A	0.1455	0.6624	0.5831	0.059*
H3B	0.1477	0.5622	0.6278	0.059*
C4	0.1117 (4)	0.5559 (4)	0.4816 (3)	0.0460 (14)
H4A	0.1282	0.4895	0.4836	0.055*
H4B	0.0404	0.5615	0.4539	0.055*
C5	0.2795 (6)	0.6828 (4)	0.3168 (4)	0.0618 (19)
H5A	0.3255	0.7348	0.3474	0.074*
H5B	0.2159	0.7030	0.3087	0.074*
C6	0.2663 (5)	0.6687 (5)	0.2151 (4)	0.0585 (17)
H6A	0.2024	0.6383	0.1751	0.070*
H6B	0.2618	0.7307	0.1868	0.070*
C7	0.5257 (10)	0.7313 (5)	0.1286 (10)	0.043 (3)	0.50
H7A	0.5182	0.7402	0.0632	0.052*	0.50
H7B	0.5951	0.7409	0.1775	0.052*	0.50
C8	0.4610 (5)	0.8015 (9)	0.1450 (8)	0.046 (3)	0.50
H8A	0.4716	0.7950	0.2117	0.056*	0.50
H8B	0.4787	0.8654	0.1371	0.056*	0.50
C9	0.2178 (4)	0.6113 (5)	−0.1472 (4)	0.0574 (17)
H9A	0.2074	0.5823	−0.2083	0.069*
H9B	0.1928	0.6755	−0.1617	0.069*
C10	0.1636 (4)	0.5561 (5)	−0.1053 (4)	0.0563 (17)
H10A	0.0925	0.5586	−0.1505	0.068*
H10B	0.1844	0.4906	−0.0963	0.068*
C1'	0.4867 (9)	0.7386 (5)	0.6036 (12)	0.058 (3)	0.50
H1'A	0.4973	0.7448	0.5473	0.070*	0.50
H1'B	0.5499	0.7505	0.6629	0.070*	0.50
C2'	0.4137 (5)	0.8140 (11)	0.5957 (12)	0.055 (4)	0.50
H2'A	0.4213	0.8262	0.6606	0.066*	0.50
H2'B	0.4268	0.8722	0.5713	0.066*	0.50
C7'	0.5261 (10)	0.7331 (5)	0.1712 (8)	0.043 (3)	0.50
H7'A	0.5935	0.7424	0.1839	0.052*	0.50
H7'B	0.5258	0.7431	0.2329	0.052*	0.50
C8'	0.4578 (5)	0.8049 (9)	0.0949 (10)	0.046 (3)	0.50
H8'A	0.4762	0.8684	0.1211	0.056*	0.50
H8'B	0.4628	0.8003	0.0352	0.056*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0298 (3)	0.0409 (4)	0.0276 (3)	0.0003 (2)	0.0147 (3)	−0.0005 (2)
Zn2	0.0274 (3)	0.0432 (4)	0.0292 (3)	−0.0020 (2)	0.0144 (3)	0.0004 (2)
Cl1	0.0314 (7)	0.0538 (9)	0.0481 (8)	−0.0001 (6)	0.0161 (6)	0.0014 (7)
Cl2	0.0403 (8)	0.0667 (11)	0.0506 (9)	0.0023 (7)	0.0127 (7)	−0.0126 (8)
Cl3	0.0601 (9)	0.0463 (9)	0.0515 (9)	−0.0122 (7)	0.0330 (8)	−0.0077 (7)
Cl4	0.0544 (9)	0.0410 (8)	0.0751 (11)	−0.0058 (6)	0.0345 (8)	−0.0049 (8)
O1	0.159 (11)	0.238 (14)	0.172 (11)	0.013 (9)	0.136 (10)	−0.005 (9)
O2	0.095 (7)	0.076 (7)	0.060 (6)	0.013 (6)	−0.006 (5)	0.010 (5)
O3	0.128 (9)	0.074 (8)	0.158 (10)	−0.005 (7)	0.039 (8)	0.024 (7)
O4	0.049 (7)	0.066 (8)	0.059 (7)	0.008 (6)	0.012 (5)	0.012 (5)
O5	0.056 (6)	0.049 (6)	0.086 (8)	0.004 (5)	0.027 (5)	0.025 (5)
O6	0.160 (10)	0.167 (11)	0.134 (10)	0.010 (8)	0.088 (8)	−0.068 (8)
O7	0.106 (8)	0.069 (7)	0.116 (8)	−0.021 (6)	0.046 (6)	0.002 (6)
O8	0.041 (5)	0.054 (6)	0.058 (6)	−0.004 (4)	0.007 (4)	0.021 (5)
O9	0.059 (7)	0.084 (8)	0.060 (7)	−0.014 (6)	0.019 (5)	0.023 (6)
O10	0.056 (5)	0.066 (6)	0.101 (7)	0.002 (4)	0.043 (5)	−0.042 (5)
O11	0.108 (7)	0.095 (7)	0.063 (6)	−0.003 (6)	0.056 (6)	0.007 (5)
O12	0.044 (5)	0.051 (5)	0.070 (6)	−0.007 (4)	0.020 (5)	−0.034 (5)
O13	0.044 (5)	0.053 (6)	0.072 (6)	−0.020 (4)	0.017 (5)	−0.021 (5)
O14	0.081 (6)	0.080 (6)	0.083 (6)	−0.017 (5)	0.067 (5)	−0.012 (5)
O15	0.080 (7)	0.047 (5)	0.165 (10)	0.018 (5)	0.051 (6)	−0.001 (6)
O16	0.129 (8)	0.108 (8)	0.052 (5)	−0.039 (7)	0.032 (6)	0.008 (6)
O1'	0.054 (8)	0.067 (9)	0.079 (8)	0.006 (6)	0.034 (6)	−0.008 (6)
O2'	0.148 (10)	0.155 (10)	0.096 (8)	0.020 (8)	0.065 (7)	0.035 (7)
O3'	0.054 (5)	0.065 (6)	0.162 (9)	−0.007 (4)	0.068 (6)	−0.029 (6)
O4'	0.101 (7)	0.055 (6)	0.094 (7)	0.018 (5)	0.031 (6)	−0.020 (5)
O5'	0.062 (6)	0.079 (8)	0.086 (8)	−0.003 (5)	0.053 (6)	0.015 (6)
O6'	0.105 (7)	0.097 (7)	0.075 (6)	0.031 (6)	0.048 (5)	−0.020 (6)
O7'	0.117 (8)	0.063 (7)	0.113 (8)	0.003 (6)	0.026 (7)	−0.035 (6)
O8'	0.073 (7)	0.077 (8)	0.056 (7)	−0.028 (5)	0.013 (5)	0.027 (6)
O9'	0.053 (7)	0.091 (9)	0.067 (8)	−0.018 (6)	0.011 (5)	0.008 (6)
O10'	0.181 (13)	0.208 (14)	0.213 (14)	−0.029 (9)	0.088 (10)	0.059 (10)
O11'	0.176 (11)	0.146 (11)	0.125 (10)	−0.019 (8)	0.110 (9)	−0.022 (7)
O12'	0.119 (11)	0.101 (10)	0.148 (11)	−0.004 (7)	0.064 (8)	−0.039 (8)
O13'	0.111 (10)	0.082 (9)	0.168 (12)	−0.012 (7)	0.067 (8)	0.007 (7)
O14'	0.120 (9)	0.144 (11)	0.207 (12)	0.008 (8)	0.091 (9)	−0.003 (9)
O15'	0.207 (12)	0.197 (13)	0.152 (11)	−0.019 (9)	0.084 (9)	0.033 (9)
O16'	0.135 (9)	0.156 (10)	0.133 (9)	−0.029 (8)	0.089 (7)	−0.053 (8)
N1	0.033 (2)	0.059 (3)	0.038 (3)	0.008 (2)	0.016 (2)	0.002 (2)
N2	0.042 (3)	0.041 (3)	0.051 (3)	0.001 (2)	0.022 (2)	−0.001 (2)
N3	0.039 (2)	0.048 (3)	0.035 (2)	0.002 (2)	0.017 (2)	0.006 (2)
N4	0.034 (2)	0.066 (3)	0.033 (2)	−0.006 (2)	0.013 (2)	−0.001 (2)
N5	0.049 (3)	0.063 (3)	0.033 (2)	0.012 (2)	0.024 (2)	0.005 (2)
N6	0.051 (3)	0.094 (4)	0.040 (3)	0.018 (3)	0.029 (2)	0.020 (3)
N7	0.026 (2)	0.044 (3)	0.042 (2)	0.0059 (18)	0.0162 (19)	0.005 (2)
N8	0.033 (2)	0.045 (3)	0.051 (3)	0.006 (2)	0.019 (2)	0.008 (2)
N9	0.049 (3)	0.069 (4)	0.041 (3)	−0.001 (2)	0.028 (2)	−0.008 (3)
N10	0.036 (2)	0.064 (3)	0.042 (3)	−0.013 (2)	0.022 (2)	−0.011 (2)
C1	0.031 (4)	0.068 (6)	0.061 (9)	−0.010 (4)	0.012 (6)	−0.013 (6)
C2	0.050 (4)	0.038 (6)	0.082 (10)	−0.012 (4)	0.036 (5)	−0.031 (6)
C3	0.042 (3)	0.062 (4)	0.052 (3)	0.001 (3)	0.030 (3)	0.005 (3)
C4	0.035 (3)	0.051 (4)	0.047 (3)	−0.001 (2)	0.016 (3)	0.007 (3)
C5	0.093 (5)	0.055 (4)	0.061 (4)	0.018 (4)	0.056 (4)	0.019 (3)
C6	0.072 (5)	0.060 (4)	0.050 (4)	0.021 (3)	0.035 (3)	0.012 (3)
C7	0.029 (3)	0.052 (4)	0.048 (8)	0.000 (3)	0.019 (6)	0.014 (5)
C8	0.038 (4)	0.042 (4)	0.059 (7)	−0.007 (3)	0.024 (5)	−0.002 (6)
C9	0.059 (4)	0.071 (4)	0.031 (3)	−0.007 (3)	0.014 (3)	−0.004 (3)
C10	0.050 (4)	0.072 (5)	0.043 (3)	−0.015 (3)	0.021 (3)	−0.020 (3)
C1'	0.031 (4)	0.068 (6)	0.061 (9)	−0.010 (4)	0.012 (6)	−0.013 (6)
C2'	0.050 (4)	0.038 (6)	0.082 (10)	−0.012 (4)	0.036 (5)	−0.031 (6)
C7'	0.029 (3)	0.052 (4)	0.048 (8)	0.000 (3)	0.019 (6)	0.014 (5)
C8'	0.038 (4)	0.042 (4)	0.059 (7)	−0.007 (3)	0.024 (5)	−0.002 (6)

Geometric parameters (Å, º) top

Zn1—N2	2.108 (5)	N5—C5	1.455 (5)
Zn1—N5	2.111 (4)	N5—H51	0.8600
Zn1—N3	2.112 (4)	N5—H52	0.8600
Zn1—N1	2.148 (5)	N6—C6	1.459 (5)
Zn1—N4	2.185 (4)	N6—H61	0.8600
Zn2—N8	2.110 (5)	N6—H62	0.8600
Zn2—N10	2.129 (4)	N7—C7	1.465 (5)
Zn2—N7	2.135 (4)	N7—C7'	1.470 (5)
Zn2—N6	2.139 (5)	N7—H71	0.8600
Zn2—N9	2.147 (5)	N7—H72	0.8600
Cl1—O1	1.394 (5)	N7—H73	0.8600
Cl1—O3	1.397 (5)	N7—H74	0.8600
Cl1—O1'	1.403 (5)	N8—C8'	1.475 (5)
Cl1—O3'	1.404 (5)	N8—C8	1.477 (5)
Cl1—O2'	1.405 (5)	N8—H81	0.8600
Cl1—O4	1.415 (5)	N8—H82	0.8600
Cl1—O2	1.424 (5)	N8—H83	0.8600
Cl1—O4'	1.424 (5)	N8—H84	0.8600
Cl2—O7'	1.382 (5)	N9—C9	1.464 (5)
Cl2—O6	1.399 (5)	N9—H91	0.8600
Cl2—O8	1.401 (5)	N9—H92	0.8600
Cl2—O5	1.406 (5)	N10—C10	1.469 (4)
Cl2—O8'	1.407 (5)	N10—H101	0.8600
Cl2—O5'	1.408 (5)	N10—H102	0.8600
Cl2—O7	1.446 (5)	C1—C2	1.535 (6)
Cl2—O6'	1.452 (5)	C1—H1A	0.9800
Cl3—O9'	1.395 (5)	C1—H1B	0.9800
Cl3—O12	1.404 (4)	C2—H2A	0.9800
Cl3—O11'	1.407 (5)	C2—H2B	0.9800
Cl3—O12'	1.408 (5)	C3—C4	1.524 (5)
Cl3—O10	1.409 (4)	C3—H3A	0.9800
Cl3—O11	1.412 (5)	C3—H3B	0.9800
Cl3—O9	1.415 (5)	C4—H4A	0.9800
Cl3—O10'	1.422 (5)	C4—H4B	0.9800
Cl4—O16	1.402 (5)	C5—C6	1.518 (5)
Cl4—O14'	1.404 (5)	C5—H5A	0.9800
Cl4—O15	1.406 (5)	C5—H5B	0.9800
Cl4—O15'	1.407 (5)	C6—H6A	0.9800
Cl4—O13'	1.407 (5)	C6—H6B	0.9800
Cl4—O16'	1.411 (5)	C7—C8	1.536 (5)
Cl4—O14	1.415 (4)	C7—H7A	0.9800
Cl4—O13	1.415 (4)	C7—H7B	0.9800
N1—C1'	1.467 (5)	C8—H8A	0.9800
N1—C1	1.469 (5)	C8—H8B	0.9800
N1—H11	0.8600	C9—C10	1.524 (5)
N1—H12	0.8600	C9—H9A	0.9800
N1—H13	0.8600	C9—H9B	0.9800
N1—H14	0.8600	C10—H10A	0.9800
N2—C2'	1.466 (5)	C10—H10B	0.9800
N2—C2	1.467 (5)	C1'—C2'	1.530 (5)
N2—H21	0.8600	C1'—H1'A	0.9800
N2—H22	0.8600	C1'—H1'B	0.9800
N2—H23	0.8600	C2'—H2'A	0.9800
N2—H24	0.8600	C2'—H2'B	0.9800
N3—C3	1.467 (4)	C7'—C8'	1.537 (5)
N3—H31	0.8600	C7'—H7'A	0.9800
N3—H32	0.8600	C7'—H7'B	0.9800
N4—C4	1.469 (4)	C8'—H8'A	0.9800
N4—H41	0.8600	C8'—H8'B	0.9800
N4—H42	0.8600

N2—Zn1—N5	106.3 (2)	C7—N7—Zn2	107.1 (6)
N2—Zn1—N3	103.55 (19)	C7'—N7—Zn2	105.8 (6)
N5—Zn1—N3	149.9 (2)	C7—N7—H71	110.3
N2—Zn1—N1	82.44 (17)	Zn2—N7—H71	110.3
N5—Zn1—N1	93.49 (19)	C7—N7—H72	110.3
N3—Zn1—N1	93.88 (17)	Zn2—N7—H72	110.3
N2—Zn1—N4	105.53 (18)	H71—N7—H72	108.5
N5—Zn1—N4	87.83 (19)	C7'—N7—H73	110.6
N3—Zn1—N4	80.81 (16)	Zn2—N7—H73	110.6
N1—Zn1—N4	171.23 (18)	C7'—N7—H74	110.6
N8—Zn2—N10	112.30 (19)	Zn2—N7—H74	110.6
N8—Zn2—N7	83.33 (15)	H73—N7—H74	108.7
N10—Zn2—N7	163.64 (19)	C8'—N8—Zn2	108.8 (6)
N8—Zn2—N6	99.7 (2)	C8—N8—Zn2	106.3 (6)
N10—Zn2—N6	89.49 (19)	C8—N8—H81	110.5
N7—Zn2—N6	92.61 (19)	Zn2—N8—H81	110.5
N8—Zn2—N9	99.1 (2)	C8—N8—H82	110.5
N10—Zn2—N9	80.59 (17)	Zn2—N8—H82	110.5
N7—Zn2—N9	92.53 (18)	H81—N8—H82	108.7
N6—Zn2—N9	160.9 (2)	C8'—N8—H83	109.9
O1—Cl1—O3	112.5 (7)	Zn2—N8—H83	109.9
O3—Cl1—O1'	108.4 (10)	C8'—N8—H84	109.9
O1'—Cl1—O3'	111.2 (6)	Zn2—N8—H84	109.9
O1'—Cl1—O2'	110.8 (7)	H83—N8—H84	108.3
O3'—Cl1—O2'	111.6 (6)	C9—N9—Zn2	108.3 (3)
O1—Cl1—O4	109.7 (7)	C9—N9—H91	110.0
O3—Cl1—O4	110.0 (6)	Zn2—N9—H91	110.0
O3'—Cl1—O4	106.8 (9)	C9—N9—H92	110.0
O1—Cl1—O2	108.5 (7)	Zn2—N9—H92	110.0
O3—Cl1—O2	107.9 (6)	H91—N9—H92	108.4
O4—Cl1—O2	108.0 (6)	C10—N10—Zn2	109.9 (3)
O1'—Cl1—O4'	110.8 (6)	C10—N10—H101	109.7
O3'—Cl1—O4'	105.3 (5)	Zn2—N10—H101	109.7
O2'—Cl1—O4'	107.0 (6)	C10—N10—H102	109.7
O4—Cl1—O4'	101.2 (8)	Zn2—N10—H102	109.7
O6—Cl2—O8	112.5 (7)	H101—N10—H102	108.2
O6—Cl2—O5	112.1 (6)	N1—C1—C2	102.9 (10)
O8—Cl2—O5	112.4 (6)	N1—C1—H1A	111.2
O7'—Cl2—O8'	113.3 (6)	C2—C1—H1A	111.2
O7'—Cl2—O5'	113.7 (6)	N1—C1—H1B	111.2
O8'—Cl2—O5'	109.8 (6)	C2—C1—H1B	111.2
O6—Cl2—O7	105.6 (6)	H1A—C1—H1B	109.1
O8—Cl2—O7	107.6 (6)	N2—C2—C1	108.4 (10)
O5—Cl2—O7	106.0 (6)	N2—C2—H2A	110.0
O7'—Cl2—O6'	107.4 (6)	C1—C2—H2A	110.0
O8'—Cl2—O6'	106.4 (6)	N2—C2—H2B	110.0
O5'—Cl2—O6'	105.7 (5)	C1—C2—H2B	110.0
O9'—Cl3—O11'	112.8 (7)	H2A—C2—H2B	108.4
O9'—Cl3—O12'	112.7 (7)	N3—C3—C4	108.7 (4)
O11'—Cl3—O12'	108.3 (7)	N3—C3—H3A	109.9
O12—Cl3—O10	109.5 (5)	C4—C3—H3A	109.9
O11'—Cl3—O10	70.1 (8)	N3—C3—H3B	109.9
O12'—Cl3—O10	130.2 (8)	C4—C3—H3B	109.9
O12—Cl3—O11	111.0 (6)	H3A—C3—H3B	108.3
O10—Cl3—O11	110.8 (5)	N4—C4—C3	107.8 (4)
O12—Cl3—O9	109.2 (6)	N4—C4—H4A	110.1
O10—Cl3—O9	108.4 (6)	C3—C4—H4A	110.1
O11—Cl3—O9	107.9 (6)	N4—C4—H4B	110.1
O9'—Cl3—O10'	108.8 (7)	C3—C4—H4B	110.1
O11'—Cl3—O10'	106.2 (7)	H4A—C4—H4B	108.5
O12'—Cl3—O10'	107.7 (7)	N5—C5—C6	119.4 (5)
O16—Cl4—O15	109.5 (6)	N5—C5—H5A	107.5
O14'—Cl4—O15'	109.9 (7)	C6—C5—H5A	107.5
O14'—Cl4—O13'	110.9 (7)	N5—C5—H5B	107.5
O15'—Cl4—O13'	110.9 (7)	C6—C5—H5B	107.5
O14'—Cl4—O16'	108.8 (6)	H5A—C5—H5B	107.0
O15'—Cl4—O16'	107.0 (7)	N6—C6—C5	120.1 (5)
O13'—Cl4—O16'	109.3 (7)	N6—C6—H6A	107.3
O16—Cl4—O14	108.9 (6)	C5—C6—H6A	107.3
O15—Cl4—O14	109.2 (6)	N6—C6—H6B	107.3
O16—Cl4—O13	112.5 (6)	C5—C6—H6B	107.3
O15—Cl4—O13	109.5 (5)	H6A—C6—H6B	106.9
O16'—Cl4—O13	119.2 (8)	N7—C7—C8	108.3 (9)
O14—Cl4—O13	107.2 (5)	N7—C7—H7A	110.0
C1'—N1—Zn1	106.3 (6)	C8—C7—H7A	110.0
C1—N1—Zn1	106.6 (6)	N7—C7—H7B	110.0
C1—N1—H11	110.4	C8—C7—H7B	110.0
Zn1—N1—H11	110.4	H7A—C7—H7B	108.4
C1—N1—H12	110.4	N8—C8—C7	109.3 (9)
Zn1—N1—H12	110.4	N8—C8—H8A	109.8
H11—N1—H12	108.6	C7—C8—H8A	109.8
C1'—N1—H13	110.5	N8—C8—H8B	109.8
Zn1—N1—H13	110.5	C7—C8—H8B	109.8
C1'—N1—H14	110.5	H8A—C8—H8B	108.3
Zn1—N1—H14	110.5	N9—C9—C10	108.2 (5)
H13—N1—H14	108.7	N9—C9—H9A	110.0
C2—N2—Zn1	103.4 (7)	C10—C9—H9A	110.0
C2—N2—H21	111.1	N9—C9—H9B	110.0
Zn1—N2—H21	111.1	C10—C9—H9B	110.0
C2—N2—H22	111.1	H9A—C9—H9B	108.4
Zn1—N2—H22	111.1	N10—C10—C9	108.2 (5)
H21—N2—H22	109.0	N10—C10—H10A	110.1
C2'—N2—H23	108.9	C9—C10—H10A	110.1
Zn1—N2—H23	108.9	N10—C10—H10B	110.1
C2'—N2—H24	108.9	C9—C10—H10B	110.1
Zn1—N2—H24	108.9	H10A—C10—H10B	108.4
H23—N2—H24	107.7	N1—C1'—C2'	115.6 (11)
C3—N3—Zn1	108.6 (3)	N1—C1'—H1'A	108.4
C3—N3—H31	110.0	C2'—C1'—H1'A	108.4
Zn1—N3—H31	110.0	N1—C1'—H1'B	108.4
C3—N3—H32	110.0	C2'—C1'—H1'B	108.4
Zn1—N3—H32	110.0	H1'A—C1'—H1'B	107.4
H31—N3—H32	108.4	N2—C2'—C1'	109.2 (9)
C4—N4—Zn1	108.0 (3)	N2—C2'—H2'A	109.8
C4—N4—H41	110.1	C1'—C2'—H2'A	109.8
Zn1—N4—H41	110.1	N2—C2'—H2'B	109.8
C4—N4—H42	110.1	C1'—C2'—H2'B	109.8
Zn1—N4—H42	110.1	H2'A—C2'—H2'B	108.3
H41—N4—H42	108.4	N7—C7'—C8'	111.6 (9)
C5—N5—Zn1	111.4 (3)	N7—C7'—H7'A	109.3
C5—N5—H51	109.4	C8'—C7'—H7'A	109.3
Zn1—N5—H51	109.4	N7—C7'—H7'B	109.3
C5—N5—H52	109.4	C8'—C7'—H7'B	109.3
Zn1—N5—H52	109.4	H7'A—C7'—H7'B	108.0
H51—N5—H52	108.0	N8—C8'—C7'	107.2 (9)
C6—N6—Zn2	115.7 (4)	N8—C8'—H8'A	110.3
C6—N6—H61	108.4	C7'—C8'—H8'A	110.3
Zn2—N6—H61	108.4	N8—C8'—H8'B	110.3
C6—N6—H62	108.4	C7'—C8'—H8'B	110.3
Zn2—N6—H62	108.4	H8'A—C8'—H8'B	108.5
H61—N6—H62	107.4

N2—Zn1—N1—C1'	−18.1 (7)	N10—Zn2—N8—C8	168.6 (6)
N5—Zn1—N1—C1'	87.9 (7)	N7—Zn2—N8—C8	−16.4 (6)
N3—Zn1—N1—C1'	−121.3 (7)	N6—Zn2—N8—C8	75.1 (6)
N2—Zn1—N1—C1	15.8 (7)	N9—Zn2—N8—C8	−107.9 (6)
N5—Zn1—N1—C1	121.8 (7)	N8—Zn2—N9—C9	−93.8 (4)
N3—Zn1—N1—C1	−87.4 (7)	N10—Zn2—N9—C9	17.4 (4)
N5—Zn1—N2—C2'	−93.8 (9)	N7—Zn2—N9—C9	−177.5 (4)
N3—Zn1—N2—C2'	89.9 (9)	N6—Zn2—N9—C9	77.0 (7)
N1—Zn1—N2—C2'	−2.3 (9)	N8—Zn2—N10—C10	108.6 (4)
N4—Zn1—N2—C2'	173.9 (8)	N7—Zn2—N10—C10	−53.6 (8)
N5—Zn1—N2—C2	−72.2 (6)	N6—Zn2—N10—C10	−151.1 (4)
N3—Zn1—N2—C2	111.4 (6)	N9—Zn2—N10—C10	12.5 (4)
N1—Zn1—N2—C2	19.3 (6)	C1'—N1—C1—C2	49.1 (13)
N4—Zn1—N2—C2	−164.5 (6)	Zn1—N1—C1—C2	−45.4 (10)
N2—Zn1—N3—C3	86.0 (4)	C2'—N2—C2—C1	68 (3)
N5—Zn1—N3—C3	−87.1 (5)	Zn1—N2—C2—C1	−51.6 (10)
N1—Zn1—N3—C3	169.1 (4)	N1—C1—C2—N2	67.4 (12)
N4—Zn1—N3—C3	−17.9 (4)	Zn1—N3—C3—C4	45.0 (5)
N2—Zn1—N4—C4	−114.1 (4)	Zn1—N4—C4—C3	39.4 (5)
N5—Zn1—N4—C4	139.6 (4)	N3—C3—C4—N4	−57.2 (6)
N3—Zn1—N4—C4	−12.5 (4)	Zn1—N5—C5—C6	−169.5 (5)
N2—Zn1—N5—C5	−28.7 (5)	Zn2—N6—C6—C5	−161.0 (5)
N3—Zn1—N5—C5	144.3 (4)	N5—C5—C6—N6	−41.0 (10)
N1—Zn1—N5—C5	−111.8 (5)	C7'—N7—C7—C8	−51.0 (16)
N4—Zn1—N5—C5	76.9 (5)	Zn2—N7—C7—C8	40.2 (10)
N8—Zn2—N6—C6	56.0 (5)	C8'—N8—C8—C7	−56.4 (14)
N10—Zn2—N6—C6	−56.6 (5)	Zn2—N8—C8—C7	43.1 (10)
N7—Zn2—N6—C6	139.6 (5)	N7—C7—C8—N8	−57.5 (13)
N9—Zn2—N6—C6	−114.9 (6)	Zn2—N9—C9—C10	−43.4 (6)
N8—Zn2—N7—C7	−13.6 (6)	Zn2—N10—C10—C9	−39.2 (6)
N10—Zn2—N7—C7	149.8 (7)	N9—C9—C10—N10	55.6 (7)
N6—Zn2—N7—C7	−113.1 (6)	C1—N1—C1'—C2'	−58.6 (18)
N9—Zn2—N7—C7	85.3 (6)	Zn1—N1—C1'—C2'	36.8 (14)
N8—Zn2—N7—C7'	13.8 (6)	C2—N2—C2'—C1'	−46 (2)
N10—Zn2—N7—C7'	177.2 (7)	Zn1—N2—C2'—C1'	21.6 (16)
N6—Zn2—N7—C7'	−85.7 (6)	N1—C1'—C2'—N2	−39.9 (19)
N9—Zn2—N7—C7'	112.7 (6)	C7—N7—C7'—C8'	56.5 (16)
N10—Zn2—N8—C8'	−160.0 (6)	Zn2—N7—C7'—C8'	−40.3 (10)
N7—Zn2—N8—C8'	15.0 (6)	C8—N8—C8'—C7'	50.7 (13)
N6—Zn2—N8—C8'	106.5 (6)	Zn2—N8—C8'—C7'	−39.5 (11)
N9—Zn2—N8—C8'	−76.5 (6)	N7—C7'—C8'—N8	55.0 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O1	0.86	1.93	2.790 (9)	174
N1—H13···O8′	0.86	2.22	3.066 (12)	169
N3—H32···O12	0.86	2.34	3.018 (7)	136
N3—H32···O12′	0.86	2.29	3.070 (10)	152
N4—H41···O7ⁱ	0.86	2.35	3.157 (12)	156
N4—H41···O7′ⁱ	0.86	2.08	2.885 (9)	156
N4—H42···O16′	0.86	2.12	2.973 (8)	175
N5—H51···O1	0.86	2.30	3.120 (15)	159
N6—H62···O2	0.86	2.29	3.034 (11)	146
N7—H71···O2	0.86	2.32	3.163 (10)	168
N7—H71···O2′	0.86	2.22	3.018 (10)	154
N7—H74···O6ⁱⁱ	0.86	2.35	3.143 (11)	154
N7—H74···O6′ⁱⁱ	0.86	2.36	3.210 (9)	172
N8—H81···O11ⁱⁱ	0.86	2.26	3.075 (8)	157
N8—H81···O11′ⁱⁱ	0.86	2.29	3.148 (12)	177
N10—H102···O3ⁱ	0.86	2.17	2.929 (9)	146

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₂H₈N₂)₅](ClO₄)₄
M_r	829.06
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	248
a, b, c (Å)	15.6297 (8), 14.3133 (7), 15.6811 (8)
β (°)	119.636 (1)
V (Å³)	3049.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.45 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.711, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14146, 6543, 4259
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.186, 1.05
No. of reflections	6543
No. of parameters	535
No. of restraints	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.83

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O1	0.86	1.93	2.790 (9)	174.0
N1—H13···O8'	0.86	2.22	3.066 (12)	168.5
N3—H32···O12	0.86	2.34	3.018 (7)	136.0
N3—H32···O12'	0.86	2.29	3.070 (10)	151.6
N4—H41···O7ⁱ	0.86	2.35	3.157 (12)	156.1
N4—H41···O7'ⁱ	0.86	2.08	2.885 (9)	156.1
N4—H42···O16'	0.86	2.12	2.973 (8)	174.5
N5—H51···O1	0.86	2.30	3.120 (15)	158.8
N6—H62···O2	0.86	2.29	3.034 (11)	145.5
N7—H71···O2	0.86	2.32	3.163 (10)	167.7
N7—H71···O2'	0.86	2.22	3.018 (10)	153.7
N7—H74···O6ⁱⁱ	0.86	2.35	3.143 (11)	153.5
N7—H74···O6'ⁱⁱ	0.86	2.36	3.210 (9)	172.0
N8—H81···O11ⁱⁱ	0.86	2.26	3.075 (8)	157.1
N8—H81···O11'ⁱⁱ	0.86	2.29	3.148 (12)	177.1
N10—H102···O3ⁱ	0.86	2.17	2.929 (9)	146.3

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

Acknowledgements

We thank Hunan University of Science and Engineering and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2003). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khan, M. K., Yohannes, E. & Doedens, R. J. (2003). Inorg. Chem. 42, 3125–3129. Web of Science CSD CrossRef PubMed CAS Google Scholar
Natarajan, S., Narayan, K. S. & Pati, S. K. (2006). J. Chem. Sci. (Bangalore, India), 118, 57–65. Google Scholar
Qi, Q.-F., Li, Y.-G., Qin, C., Wang, E.-B., Xiao, D.-R., Wang, X.-L. & Chang, S. (2007). Inorg. Chem. 46, 3217–3230. Web of Science CSD CrossRef PubMed CAS 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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