{3,14-Dimethyl-2,6,13,17-tetra­aza­tricyclo­[16.4.0.07,12]docosane-κ4N,N′,N′′,N′′′)bis­(nitrato-κO)copper(II)

Choi, J.-H.; Subhan, M.A.; Ng, S.W.

doi:10.1107/S1600536812001845

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m190

doi:10.1107/S1600536812001845

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{3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane-κ⁴N,N′,N′′,N′′′)bis(nitrato-κO)copper(II)

Jong-Ha Choi,^a Md Abdus Subhan ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Andong National University, Andong 760-749, Republic of Korea, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 3 January 2012; accepted 15 January 2012; online 21 January 2012)

The Cu^II atom in the title compound, [Cu(NO₃)₂(C₂₀H₄₀N₄)], is N,N′,N′′,N′′′-chelated by the macrocyclic ligand: the four N atoms form a square, above and below which are located the O atoms of the nitrate ions. The metal atom exists in a tetragonally distorted octahedron, on a special position of $[\overline{1}]$ site symmetry. One of the amino groups is hydrogen bonded to an O atom of the nitrate ion. The other amino group is hydrogen bonded to O atom of an adjacent molecule, generating a supramolecular dimeric hydrogen-bonded dinuclear aggregate.

Related literature

For the synthesis of the cyclam, see: Choi et al. (2012 ). For similar copper nitrate–cyclam adducts, see: Amadei et al. (1999 ); Choi et al. (2001 , 2006 ); Dong et al. (1999 ); Liu & Chu (2010 ).

Experimental

Crystal data

[Cu(NO₃)₂(C₂₀H₄₀N₄)]
M_r = 524.12
Triclinic, $[P \overline 1]$
a = 8.2552 (10) Å
b = 8.8074 (11) Å
c = 9.1399 (10) Å
α = 67.879 (12)°
β = 68.780 (11)°
γ = 75.096 (11)°
V = 568.23 (12) Å³
Z = 1
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.751, T_max = 0.906
4122 measured reflections
2332 independent reflections
1963 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.132
S = 1.02
2332 reflections
159 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88 (1)	2.15 (2)	2.992 (3)	160 (3)
N2—H2⋯O3ⁱⁱ	0.88 (1)	2.23 (2)	2.961 (3)	140 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 10.1107/S1600536812001845/xu5440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001845/xu5440Isup2.hkl

checkCIF report

Comment top

The macrocycle, cyclam (1,4,8,11-tetraazacyclotetradecane), forms a large number of complexes with copper(II) salts in which the macrocle chelates in a tetradentate matter. In same cases, the counterion bonded to the metal atoms and in other cases, the metal atom exists in square-pyramidal geometry as the counterion is far away. The crystal structure of copper nitrate–cyclam has not been reported; the crystal structures of other substituted cyclams have the metal atom in a tetragonally elongated octahedral geometry (Amadei et al., 1999; Choi et al., 2006; Choi et al., 2001; Dong et al., 1999; Liu & Chu, 2010). The Cu^II atom in the title compound (Scheme I) is similarly chelated by the macrocyclic ligand in a tetragonally distorted octahedron (Fig.1). The atom lies on a special position of –1 site symmetry. One of the amino groups is hydrogen-bonded to an O atom of the nitrate ion. The other amino group is hydrogen-bonded to O atom of an adjacent molecule to generate a hydrogen-bonded dinuclear molecule (Table 1).

Related literature top

For the synthesis of the cyclam, see: Choi et al. (2012). For similar copper nitrate–cyclam adducts, see: Amadei et al. (1999); Choi et al. (2001, 2006); Dong et al. (1999); Liu & Chu (2010).

Experimental top

The macrocycle co-crystal, 3,14-dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.0^7,12)docosane (naphthalen-1-yl)methanol prepared as described (Choi et al., 2012). Copper nitrate trihydrate (0.242 g, 1 mmol) dissolved in methanol (10 ml) was mixed with a suspension of the macrocycle co-crystal (0.163 g, 2.5 mmol) dissolved in methanol (10 ml). The mixture was heated for 30 minutes and then set aside for the growth of purple crystals.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 Cu(NO₃)₂(C₂₀H₄₀N₄) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane- κ⁴N,N',N'',N''')bis(nitrato-κO)copper(II) top

Crystal data top

[Cu(NO₃)₂(C₂₀H₄₀N₄)]	Z = 1
M_r = 524.12	F(000) = 279
Triclinic, P1	D_x = 1.532 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2552 (10) Å	Cell parameters from 1668 reflections
b = 8.8074 (11) Å	θ = 2.5–27.5°
c = 9.1399 (10) Å	µ = 1.01 mm⁻¹
α = 67.879 (12)°	T = 100 K
β = 68.780 (11)°	Prism, purple
γ = 75.096 (11)°	0.30 × 0.20 × 0.10 mm
V = 568.23 (12) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2332 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1963 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.064
Detector resolution: 10.4041 pixels mm^-1	θ_max = 26.5°, θ_min = 2.5°
ω scan	h = −7→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→11
T_min = 0.751, T_max = 0.906	l = −11→10
4122 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0874P)²] where P = (F_o² + 2F_c²)/3
2332 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 0.96 e Å⁻³
2 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Cu(NO₃)₂(C₂₀H₄₀N₄)]	γ = 75.096 (11)°
M_r = 524.12	V = 568.23 (12) Å³
Triclinic, P1	Z = 1
a = 8.2552 (10) Å	Mo Kα radiation
b = 8.8074 (11) Å	µ = 1.01 mm⁻¹
c = 9.1399 (10) Å	T = 100 K
α = 67.879 (12)°	0.30 × 0.20 × 0.10 mm
β = 68.780 (11)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2332 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1963 reflections with I > 2σ(I)
T_min = 0.751, T_max = 0.906	R_int = 0.064
4122 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	2 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.96 e Å⁻³
2332 reflections	Δρ_min = −0.68 e Å⁻³
159 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.5000	0.5000	0.0158 (2)
N1	0.5570 (3)	0.5225 (3)	0.2605 (3)	0.0152 (5)
H1	0.473 (3)	0.481 (4)	0.257 (4)	0.022 (9)*
N2	0.6852 (3)	0.2945 (3)	0.5073 (3)	0.0154 (5)
H2	0.777 (3)	0.342 (3)	0.484 (4)	0.014 (8)*
N3	0.8305 (3)	0.6621 (3)	0.5099 (3)	0.0193 (6)
O1	0.7574 (3)	0.6375 (3)	0.4223 (3)	0.0228 (5)
O2	0.7518 (3)	0.6441 (3)	0.6596 (3)	0.0280 (5)
O3	0.9780 (3)	0.7070 (3)	0.4452 (3)	0.0260 (5)
C1	0.5512 (4)	0.6927 (4)	0.1448 (4)	0.0201 (6)
H1A	0.5787	0.6891	0.0312	0.024*
H1B	0.6413	0.7475	0.1460	0.024*
C2	0.7261 (4)	0.4161 (4)	0.2131 (4)	0.0171 (6)
H2A	0.8227	0.4708	0.2045	0.020*
C3	0.7647 (4)	0.3870 (4)	0.0493 (4)	0.0203 (6)
H3A	0.7728	0.4940	−0.0408	0.024*
H3B	0.6675	0.3379	0.0528	0.024*
C4	0.9369 (4)	0.2708 (4)	0.0141 (4)	0.0207 (6)
H4A	0.9581	0.2509	−0.0913	0.025*
H4B	1.0353	0.3236	0.0023	0.025*
C5	0.9308 (4)	0.1064 (4)	0.1531 (4)	0.0206 (6)
H5A	1.0448	0.0348	0.1299	0.025*
H5B	0.8386	0.0494	0.1593	0.025*
C6	0.8921 (4)	0.1347 (4)	0.3181 (4)	0.0196 (6)
H6A	0.9906	0.1813	0.3155	0.024*
H6B	0.8821	0.0275	0.4079	0.024*
C7	0.7216 (4)	0.2533 (4)	0.3538 (4)	0.0169 (6)
H7	0.6221	0.2001	0.3659	0.020*
C8	0.6715 (4)	0.1477 (4)	0.6603 (4)	0.0177 (6)
H8	0.7896	0.0787	0.6487	0.021*
C9	0.6290 (4)	0.2073 (4)	0.8083 (4)	0.0192 (6)
H9A	0.6398	0.1093	0.9053	0.023*
H9B	0.7189	0.2758	0.7851	0.023*
C10	0.5417 (4)	0.0404 (4)	0.6826 (4)	0.0206 (6)
H10A	0.5752	0.0052	0.5846	0.031*
H10B	0.4238	0.1039	0.6971	0.031*
H10C	0.5422	−0.0573	0.7804	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0102 (3)	0.0195 (3)	0.0187 (3)	−0.00213 (18)	−0.0034 (2)	−0.0080 (2)
N1	0.0079 (11)	0.0190 (13)	0.0199 (13)	−0.0024 (9)	−0.0025 (10)	−0.0087 (10)
N2	0.0119 (12)	0.0181 (13)	0.0187 (12)	−0.0057 (9)	−0.0030 (10)	−0.0077 (10)
N3	0.0125 (12)	0.0193 (13)	0.0287 (15)	−0.0028 (9)	−0.0085 (11)	−0.0076 (11)
O1	0.0175 (11)	0.0303 (12)	0.0264 (11)	−0.0086 (9)	−0.0087 (9)	−0.0097 (10)
O2	0.0239 (12)	0.0397 (14)	0.0253 (12)	−0.0131 (10)	−0.0032 (10)	−0.0138 (10)
O3	0.0137 (11)	0.0310 (13)	0.0362 (13)	−0.0103 (9)	−0.0086 (10)	−0.0078 (10)
C1	0.0147 (14)	0.0264 (17)	0.0190 (15)	−0.0034 (12)	−0.0033 (12)	−0.0084 (13)
C2	0.0079 (13)	0.0242 (16)	0.0223 (15)	−0.0026 (11)	−0.0026 (11)	−0.0122 (13)
C3	0.0184 (15)	0.0252 (17)	0.0207 (15)	−0.0028 (12)	−0.0053 (12)	−0.0115 (13)
C4	0.0163 (15)	0.0252 (16)	0.0216 (15)	−0.0010 (12)	−0.0021 (12)	−0.0131 (13)
C5	0.0155 (15)	0.0241 (16)	0.0258 (16)	−0.0010 (12)	−0.0039 (12)	−0.0151 (13)
C6	0.0146 (14)	0.0233 (16)	0.0224 (15)	−0.0003 (11)	−0.0047 (12)	−0.0110 (13)
C7	0.0123 (14)	0.0232 (15)	0.0197 (15)	−0.0042 (11)	−0.0033 (11)	−0.0120 (12)
C8	0.0117 (14)	0.0210 (15)	0.0196 (15)	−0.0015 (11)	−0.0049 (11)	−0.0057 (12)
C9	0.0174 (15)	0.0215 (15)	0.0198 (15)	−0.0012 (11)	−0.0067 (12)	−0.0077 (12)
C10	0.0163 (15)	0.0216 (16)	0.0253 (16)	−0.0057 (11)	−0.0048 (12)	−0.0081 (13)

Geometric parameters (Å, º) top

Cu1—N1	2.007 (2)	C3—H3A	0.9900
Cu1—N1ⁱ	2.007 (2)	C3—H3B	0.9900
Cu1—N2ⁱ	2.044 (2)	C4—C5	1.523 (4)
Cu1—N2	2.044 (2)	C4—H4A	0.9900
Cu1—O1	2.463 (2)	C4—H4B	0.9900
N1—C1	1.475 (4)	C5—C6	1.527 (4)
N1—C2	1.486 (3)	C5—H5A	0.9900
N1—H1	0.879 (10)	C5—H5B	0.9900
N2—C7	1.487 (4)	C6—C7	1.532 (4)
N2—C8	1.496 (4)	C6—H6A	0.9900
N2—H2	0.878 (10)	C6—H6B	0.9900
N3—O3	1.241 (3)	C7—H7	1.0000
N3—O2	1.251 (3)	C8—C10	1.517 (4)
N3—O1	1.265 (3)	C8—C9	1.525 (4)
C1—C9ⁱ	1.524 (4)	C8—H8	1.0000
C1—H1A	0.9900	C9—C1ⁱ	1.524 (4)
C1—H1B	0.9900	C9—H9A	0.9900
C2—C3	1.520 (4)	C9—H9B	0.9900
C2—C7	1.521 (4)	C10—H10A	0.9800
C2—H2A	1.0000	C10—H10B	0.9800
C3—C4	1.530 (4)	C10—H10C	0.9800

N1—Cu1—N1ⁱ	180.0	H3A—C3—H3B	108.1
N1—Cu1—N2ⁱ	95.20 (9)	C5—C4—C3	110.9 (2)
N1ⁱ—Cu1—N2ⁱ	84.80 (9)	C5—C4—H4A	109.5
N1—Cu1—N2	84.80 (9)	C3—C4—H4A	109.5
N1ⁱ—Cu1—N2	95.20 (9)	C5—C4—H4B	109.5
N2ⁱ—Cu1—N2	180.000 (1)	C3—C4—H4B	109.5
N1—Cu1—O1	87.75 (8)	H4A—C4—H4B	108.1
N1ⁱ—Cu1—O1	92.25 (8)	C4—C5—C6	110.4 (2)
N2ⁱ—Cu1—O1	97.63 (8)	C4—C5—H5A	109.6
N2—Cu1—O1	82.37 (8)	C6—C5—H5A	109.6
C1—N1—C2	113.1 (2)	C4—C5—H5B	109.6
C1—N1—Cu1	116.33 (18)	C6—C5—H5B	109.6
C2—N1—Cu1	108.35 (17)	H5A—C5—H5B	108.1
C1—N1—H1	106 (2)	C5—C6—C7	111.2 (2)
C2—N1—H1	108 (2)	C5—C6—H6A	109.4
Cu1—N1—H1	104 (2)	C7—C6—H6A	109.4
C7—N2—C8	114.3 (2)	C5—C6—H6B	109.4
C7—N2—Cu1	107.58 (17)	C7—C6—H6B	109.4
C8—N2—Cu1	121.32 (18)	H6A—C6—H6B	108.0
C7—N2—H2	102 (2)	N2—C7—C2	107.0 (2)
C8—N2—H2	111 (2)	N2—C7—C6	113.1 (2)
Cu1—N2—H2	98 (2)	C2—C7—C6	111.3 (2)
O3—N3—O2	120.9 (2)	N2—C7—H7	108.4
O3—N3—O1	119.5 (2)	C2—C7—H7	108.4
O2—N3—O1	119.6 (2)	C6—C7—H7	108.4
N3—O1—Cu1	131.16 (18)	N2—C8—C10	112.4 (2)
N1—C1—C9ⁱ	111.0 (2)	N2—C8—C9	108.9 (2)
N1—C1—H1A	109.4	C10—C8—C9	112.8 (3)
C9ⁱ—C1—H1A	109.4	N2—C8—H8	107.5
N1—C1—H1B	109.4	C10—C8—H8	107.5
C9ⁱ—C1—H1B	109.4	C9—C8—H8	107.5
H1A—C1—H1B	108.0	C1ⁱ—C9—C8	116.4 (2)
N1—C2—C3	114.3 (2)	C1ⁱ—C9—H9A	108.2
N1—C2—C7	107.1 (2)	C8—C9—H9A	108.2
C3—C2—C7	111.1 (2)	C1ⁱ—C9—H9B	108.2
N1—C2—H2A	108.0	C8—C9—H9B	108.2
C3—C2—H2A	108.0	H9A—C9—H9B	107.3
C7—C2—H2A	108.0	C8—C10—H10A	109.5
C2—C3—C4	110.7 (2)	C8—C10—H10B	109.5
C2—C3—H3A	109.5	H10A—C10—H10B	109.5
C4—C3—H3A	109.5	C8—C10—H10C	109.5
C2—C3—H3B	109.5	H10A—C10—H10C	109.5
C4—C3—H3B	109.5	H10B—C10—H10C	109.5

N2ⁱ—Cu1—N1—C1	35.3 (2)	Cu1—N1—C2—C7	42.3 (2)
N2—Cu1—N1—C1	−144.7 (2)	N1—C2—C3—C4	−177.7 (2)
O1—Cu1—N1—C1	−62.11 (19)	C7—C2—C3—C4	−56.3 (3)
N2ⁱ—Cu1—N1—C2	164.12 (17)	C2—C3—C4—C5	57.5 (3)
N2—Cu1—N1—C2	−15.88 (17)	C3—C4—C5—C6	−57.2 (3)
O1—Cu1—N1—C2	66.66 (18)	C4—C5—C6—C7	56.0 (3)
N1—Cu1—N2—C7	−14.16 (18)	C8—N2—C7—C2	178.5 (2)
N1ⁱ—Cu1—N2—C7	165.84 (18)	Cu1—N2—C7—C2	40.6 (2)
O1—Cu1—N2—C7	−102.58 (18)	C8—N2—C7—C6	−58.6 (3)
N1—Cu1—N2—C8	−148.4 (2)	Cu1—N2—C7—C6	163.59 (19)
N1ⁱ—Cu1—N2—C8	31.6 (2)	N1—C2—C7—N2	−55.2 (3)
O1—Cu1—N2—C8	123.1 (2)	C3—C2—C7—N2	179.4 (2)
O3—N3—O1—Cu1	166.62 (19)	N1—C2—C7—C6	−179.2 (2)
O2—N3—O1—Cu1	−14.8 (4)	C3—C2—C7—C6	55.3 (3)
N1—Cu1—O1—N3	−172.7 (2)	C5—C6—C7—N2	−175.7 (2)
N1ⁱ—Cu1—O1—N3	7.3 (2)	C5—C6—C7—C2	−55.2 (3)
N2ⁱ—Cu1—O1—N3	92.4 (2)	C7—N2—C8—C10	−52.7 (3)
N2—Cu1—O1—N3	−87.6 (2)	Cu1—N2—C8—C10	78.8 (3)
C2—N1—C1—C9ⁱ	175.8 (2)	C7—N2—C8—C9	−178.4 (2)
Cu1—N1—C1—C9ⁱ	−57.8 (3)	Cu1—N2—C8—C9	−46.9 (3)
C1—N1—C2—C3	−63.6 (3)	N2—C8—C9—C1ⁱ	67.3 (3)
Cu1—N1—C2—C3	165.83 (19)	C10—C8—C9—C1ⁱ	−58.2 (3)
C1—N1—C2—C7	172.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88 (1)	2.15 (2)	2.992 (3)	160 (3)
N2—H2···O3ⁱⁱ	0.88 (1)	2.23 (2)	2.961 (3)	140 (3)

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

Experimental details

Crystal data
Chemical formula	[Cu(NO₃)₂(C₂₀H₄₀N₄)]
M_r	524.12
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.2552 (10), 8.8074 (11), 9.1399 (10)
α, β, γ (°)	67.879 (12), 68.780 (11), 75.096 (11)
V (Å³)	568.23 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.751, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	4122, 2332, 1963
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.132, 1.02
No. of reflections	2332
No. of parameters	159
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.68

Computer programs: CrysAlis PRO (Agilent, 2011), 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—H1···O2ⁱ	0.88 (1)	2.15 (2)	2.992 (3)	160 (3)
N2—H2···O3ⁱⁱ	0.88 (1)	2.23 (2)	2.961 (3)	140 (3)

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

Acknowledgements

We thank Andong National University and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Amadei, G. A., Dickman, M. H., Wazzeh, R. A., Dimmock, P. & Earley, J. E. (1999). Inorg. Chim. Acta, 288, 40–46. Web of Science CSD CrossRef CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Choi, M.-H., Kim, B. J., Kim, I.-C., Kim, S.-Y., Kim, Y., Harrowfield, J. M., Lee, M. K., Mocerino, M., Rukmini, E., Skelton, B. W. & White, A. H. (2001). J. Chem. Soc. Dalton Trans. pp. 707–722. Web of Science CSD CrossRef Google Scholar
Choi, J.-H., Subhan, M. A., Ryoo, K. S. & Ng, S. W. (2012). Acta Cryst. E68, o102. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, J.-H., Suzuki, T. & Kaizaki, S. (2006). Acta Cryst. E62, m2383–m2385. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, Y., Lawrence, G. A., Lindoy, L. F. & Turner, P. (1999). J. Chem. Soc. Dalton Trans. pp. 1567–1576. Google Scholar
Liu, X.-Y. & Chu, H.-Y. (2010). Acta Cryst. E66, m837. Web of Science CSD CrossRef IUCr Journals 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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