Bis{μ-2-[1-(2-Pyridylmethyl­imino)eth­yl]phenolato}bis­[azido­copper(II)]

Zhang, J.; Chen, X.-D.; Zhang, H.-H.; Sun, B.-W.

doi:10.1107/S1600536809030475

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1136

doi:10.1107/S1600536809030475

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Bis{μ-2-[1-(2-Pyridylmethylimino)ethyl]phenolato}bis[azidocopper(II)]

Jun Zhang,^a Xiao-Dan Chen,^a Huai-Hong Zhang ^a and Bai-Wang Sun ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 10 July 2009; accepted 31 July 2009; online 26 August 2009)

The title compound, [Cu₂(C₁₄H₁₃N₂O)₂(N₃)₂], was synthesized by the reaction of Cu(NO₃)₂·3H₂O with the Schiff base 2-[1-(2-pyridylmethylimino)ethyl]phenol (HL) in methanol–water solution, adding NaN₃ as the bridging ligand. The asymmetric unit contains one half-molecule, the other half being generated by the inversion center. Each Cu^II atom shows a slightly distorted trigonal-pyramidal geometry formed by two N atoms and one O atom from one Schiff base ligand, by another O atom of a second Schiff base ligand and by an azide N atom. The crystal structure is stabilized by intermolecular C—H⋯N hydrogen bonds.

Related literature

For the potential applications in catalysis and enzymatic reactions, magnetism and molecular architecture of transition metal compounds containing Schiff base ligands, see: Li & Zhang (2004 ); You & Zhu (2004 ). For the synthesis, see: Pointeau et al. (1986 ).

Experimental

Crystal data

[Cu₂(C₁₄H₁₃N₂O)₂(N₃)₂]
M_r = 661.67
Monoclinic, P 2₁ /n
a = 10.1066 (12) Å
b = 8.0545 (10) Å
c = 16.7027 (18) Å
β = 96.251 (1)°
V = 1351.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 298 K
0.20 × 0.12 × 0.09 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.737, T_max = 0.868
6641 measured reflections
2379 independent reflections
1720 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.062
S = 1.02
2379 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯N5ⁱ	0.97	2.55	3.399 (5)	147
C14—H14⋯N3	0.93	2.55	3.052 (4)	114
Symmetry code: (i) -x, -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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030475/at2842sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030475/at2842Isup2.hkl

checkCIF report

Comment top

Transition metal compounds containing Schiff base ligands have been of great interest since many years. These compounds play an important role in the development of coordination chemistry related to their potential applications in catalysis and enzymatic reactions, magnetism and molecular architecture (You & Zhu, 2004; Li & Zhang, 2004). We have focused on the synthesis of Schiff base complexes which is formed by 2-(pyridin-2-ylethyliminomethyl)phenol (HL1) and some metal salts. To enrich our studies on schiff bases, we used HL (Pointeau, et al., 1986) instead of HL1 and gained the title compound. So, we reported this dinuclear copper(II) complex here.

The structure analyses show that complex crystallizes in monoclinic space group P21/n. The asymmetric unit contains only half of the unique molecule, and the other half is related by the inversion center (Fig.1). The molecule of the title compound is composed of two Cu^II atoms, two schiff base ligand 2-[1-(pyridin-2-ylmethylimino)-ethyl]-phenol and two azidos. Each Cu^II atom shows a slightly distorted trigonal-bipyramidal geometry formed by two N atoms and one O atom from one schiff base ligand (You & Zhu, 2004), the another O atom of the second schiff base, together with another N atom from azido.

In the structure, there are intra and intermolecular C—H···N hydrogen bond interactions (Table 2).

Related literature top

For the potential applications in catalysis and enzymatic reactions, magnetism and molecular architecture of tTransition metal compounds containing Schiff base ligands, see: Li & Zhang (2004); You & Zhu (2004). Forthe synthesis, see: Pointeau et al. (1986).

Experimental top

The title compound was synthesized by Cu(NO₃)₂.3H₂O, schiff base ligand 2-[1-(pyridin-2'-ylmethylimino)-ethyl]-phenol and sodium azide. All chemicals used (reagent grade) were commercially available. 2'-hydroxyacetophenone(0.136 g, 1 mmol) was dissolved in ethanol (5 mL) and ethanol solution (5 ml) containing 2-aminoethylpyri dine (0.108 g, 1 mmol) was added slowly with stirring. The resulting yellow solution was continuously stirred for about 30 min. at room temperature, and then Cu(NO₃)₂.3H₂O (0.241 g, 1 mmol) and sodium azide (0.13 g, 2 mmol) in aqueous solution (5 ml) was added with stirring homogeneously. Brown 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Bis{µ-2-[1-(2-Pyridylmethylimino)ethyl]phenolato}bis[azidocopper(II)] top

Crystal data top

[Cu₂(C₁₄H₁₃N₂O)₂(N₃)₂]	F(000) = 676
M_r = 661.67	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13380 reflections
a = 10.1066 (12) Å	θ = 3.0–27.6°
b = 8.0545 (10) Å	µ = 1.62 mm⁻¹
c = 16.7027 (18) Å	T = 298 K
β = 96.251 (1)°	Prism, dark green
V = 1351.6 (3) Å³	0.20 × 0.12 × 0.09 mm
Z = 2

Data collection top

Rigaku SCXmini diffractometer	2379 independent reflections
Radiation source: fine-focus sealed tube	1720 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 2.3°
Thin–slice ω scans	h = −12→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.737, T_max = 0.868	l = −19→19
6641 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0192P)²] where P = (F_o² + 2F_c²)/3
2379 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Cu₂(C₁₄H₁₃N₂O)₂(N₃)₂]	V = 1351.6 (3) Å³
M_r = 661.67	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1066 (12) Å	µ = 1.62 mm⁻¹
b = 8.0545 (10) Å	T = 298 K
c = 16.7027 (18) Å	0.20 × 0.12 × 0.09 mm
β = 96.251 (1)°

Data collection top

Rigaku SCXmini diffractometer	2379 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1720 reflections with I > 2σ(I)
T_min = 0.737, T_max = 0.868	R_int = 0.042
6641 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.02	Δρ_max = 0.35 e Å⁻³
2379 reflections	Δρ_min = −0.33 e Å⁻³
190 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
Cu1	0.00744 (4)	0.69734 (4)	0.00638 (2)	0.03343 (13)
N1	−0.0002 (2)	0.6887 (3)	0.12413 (13)	0.0349 (6)
N2	−0.1427 (2)	0.8584 (3)	0.01237 (14)	0.0324 (6)
N3	0.0263 (3)	0.7564 (3)	−0.10588 (15)	0.0448 (7)
N4	0.1145 (3)	0.7080 (3)	−0.14292 (14)	0.0391 (7)
N5	0.1975 (3)	0.6669 (4)	−0.18111 (16)	0.0579 (9)
O1	0.14375 (17)	0.5289 (2)	0.01510 (10)	0.0333 (5)
C1	0.0637 (3)	0.6042 (5)	0.26461 (17)	0.0594 (10)
H1A	0.1024	0.6932	0.2975	0.089*
H1B	0.1029	0.5008	0.2834	0.089*
H1C	−0.0305	0.6009	0.2678	0.089*
C2	0.0898 (3)	0.6322 (4)	0.17764 (17)	0.0374 (8)
C3	0.2216 (3)	0.5861 (4)	0.15511 (17)	0.0359 (8)
C4	0.2396 (3)	0.5298 (4)	0.07618 (17)	0.0347 (8)
C5	0.3666 (3)	0.4732 (4)	0.06349 (19)	0.0417 (8)
H5	0.3788	0.4258	0.0141	0.050*
C6	0.4741 (3)	0.4850 (4)	0.1214 (2)	0.0530 (9)
H6	0.5573	0.4477	0.1104	0.064*
C7	0.4584 (4)	0.5521 (4)	0.1957 (2)	0.0583 (11)
H7	0.5314	0.5661	0.2340	0.070*
C8	0.3338 (4)	0.5977 (4)	0.21236 (19)	0.0482 (9)
H8	0.3230	0.6379	0.2634	0.058*
C9	−0.1311 (3)	0.7385 (4)	0.14550 (18)	0.0443 (9)
H9A	−0.1217	0.7914	0.1980	0.053*
H9B	−0.1871	0.6413	0.1483	0.053*
C10	−0.1947 (3)	0.8571 (4)	0.08326 (18)	0.0366 (8)
C11	−0.2990 (3)	0.9584 (4)	0.0981 (2)	0.0496 (10)
H11	−0.3332	0.9548	0.1475	0.060*
C12	−0.3517 (3)	1.0650 (4)	0.0388 (2)	0.0528 (10)
H12	−0.4217	1.1350	0.0478	0.063*
C13	−0.3000 (3)	1.0671 (4)	−0.0340 (2)	0.0473 (9)
H13	−0.3352	1.1373	−0.0752	0.057*
C14	−0.1951 (3)	0.9631 (4)	−0.04483 (19)	0.0421 (8)
H14	−0.1593	0.9658	−0.0938	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0379 (2)	0.0380 (2)	0.0248 (2)	0.0016 (2)	0.00541 (15)	−0.00083 (19)
N1	0.0380 (16)	0.0401 (16)	0.0275 (14)	−0.0004 (13)	0.0078 (11)	−0.0019 (13)
N2	0.0352 (16)	0.0305 (15)	0.0317 (15)	−0.0032 (11)	0.0049 (12)	−0.0038 (11)
N3	0.0442 (18)	0.061 (2)	0.0314 (15)	0.0104 (14)	0.0125 (13)	0.0084 (13)
N4	0.0471 (19)	0.0414 (17)	0.0282 (15)	−0.0024 (15)	0.0017 (13)	0.0035 (13)
N5	0.063 (2)	0.066 (2)	0.0480 (18)	0.0109 (17)	0.0234 (16)	−0.0012 (16)
O1	0.0343 (12)	0.0404 (14)	0.0245 (11)	0.0027 (10)	0.0009 (9)	−0.0022 (9)
C1	0.075 (3)	0.076 (3)	0.029 (2)	0.009 (2)	0.0094 (17)	0.0074 (18)
C2	0.053 (2)	0.0332 (19)	0.0261 (18)	−0.0024 (16)	0.0044 (16)	−0.0019 (14)
C3	0.042 (2)	0.0366 (19)	0.0282 (18)	−0.0008 (16)	−0.0008 (15)	0.0049 (14)
C4	0.0376 (19)	0.032 (2)	0.0349 (19)	−0.0034 (14)	0.0051 (15)	0.0039 (14)
C5	0.039 (2)	0.047 (2)	0.0389 (19)	0.0029 (17)	0.0041 (15)	0.0007 (16)
C6	0.039 (2)	0.060 (2)	0.058 (2)	0.0060 (19)	−0.0008 (17)	0.006 (2)
C7	0.047 (2)	0.069 (3)	0.053 (3)	−0.0019 (19)	−0.0188 (18)	0.004 (2)
C8	0.061 (3)	0.049 (2)	0.033 (2)	−0.0034 (19)	−0.0043 (17)	0.0018 (16)
C9	0.049 (2)	0.053 (2)	0.0342 (19)	0.0045 (17)	0.0166 (16)	0.0016 (16)
C10	0.038 (2)	0.035 (2)	0.037 (2)	−0.0054 (15)	0.0083 (15)	−0.0065 (15)
C11	0.048 (2)	0.051 (3)	0.051 (2)	0.0052 (18)	0.0162 (18)	−0.0071 (18)
C12	0.042 (2)	0.052 (2)	0.065 (3)	0.0054 (18)	0.0059 (19)	−0.016 (2)
C13	0.044 (2)	0.039 (2)	0.056 (2)	−0.0018 (17)	−0.0072 (17)	0.0015 (17)
C14	0.046 (2)	0.042 (2)	0.038 (2)	−0.0022 (16)	0.0022 (15)	−0.0026 (16)

Geometric parameters (Å, º) top

Cu1—O1	1.9278 (18)	C4—C5	1.399 (4)
Cu1—N3	1.964 (2)	C5—C6	1.377 (4)
Cu1—N1	1.978 (2)	C5—H5	0.9300
Cu1—N2	2.007 (2)	C6—C7	1.379 (4)
Cu1—O1ⁱ	2.3799 (19)	C6—H6	0.9300
N1—C2	1.287 (4)	C7—C8	1.369 (4)
N1—C9	1.463 (3)	C7—H7	0.9300
N2—C14	1.340 (4)	C8—H8	0.9300
N2—C10	1.347 (3)	C9—C10	1.503 (4)
N3—N4	1.204 (3)	C9—H9A	0.9700
N4—N5	1.156 (3)	C9—H9B	0.9700
O1—C4	1.328 (3)	C10—C11	1.377 (4)
O1—Cu1ⁱ	2.3799 (19)	C11—C12	1.373 (4)
C1—C2	1.521 (4)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.375 (4)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.378 (4)
C2—C3	1.471 (4)	C13—H13	0.9300
C3—C8	1.404 (4)	C14—H14	0.9300
C3—C4	1.424 (4)

O1—Cu1—N3	95.73 (9)	C5—C4—C3	117.1 (3)
O1—Cu1—N1	90.30 (9)	C6—C5—C4	122.5 (3)
N3—Cu1—N1	167.49 (11)	C6—C5—H5	118.7
O1—Cu1—N2	171.51 (8)	C4—C5—H5	118.7
N3—Cu1—N2	92.50 (10)	C5—C6—C7	120.0 (3)
N1—Cu1—N2	82.03 (10)	C5—C6—H6	120.0
O1—Cu1—O1ⁱ	85.08 (7)	C7—C6—H6	120.0
N3—Cu1—O1ⁱ	99.74 (9)	C8—C7—C6	119.1 (3)
N1—Cu1—O1ⁱ	91.66 (8)	C8—C7—H7	120.4
N2—Cu1—O1ⁱ	91.47 (8)	C6—C7—H7	120.4
C2—N1—C9	121.1 (2)	C7—C8—C3	122.4 (3)
C2—N1—Cu1	127.0 (2)	C7—C8—H8	118.8
C9—N1—Cu1	111.55 (18)	C3—C8—H8	118.8
C14—N2—C10	118.1 (3)	N1—C9—C10	109.6 (2)
C14—N2—Cu1	127.9 (2)	N1—C9—H9A	109.8
C10—N2—Cu1	114.1 (2)	C10—C9—H9A	109.8
N4—N3—Cu1	124.5 (2)	N1—C9—H9B	109.8
N5—N4—N3	176.9 (3)	C10—C9—H9B	109.8
C4—O1—Cu1	120.63 (17)	H9A—C9—H9B	108.2
C4—O1—Cu1ⁱ	121.52 (17)	N2—C10—C11	122.2 (3)
Cu1—O1—Cu1ⁱ	94.91 (7)	N2—C10—C9	115.8 (3)
C2—C1—H1A	109.5	C11—C10—C9	122.0 (3)
C2—C1—H1B	109.5	C12—C11—C10	119.1 (3)
H1A—C1—H1B	109.5	C12—C11—H11	120.5
C2—C1—H1C	109.5	C10—C11—H11	120.5
H1A—C1—H1C	109.5	C11—C12—C13	119.4 (3)
H1B—C1—H1C	109.5	C11—C12—H12	120.3
N1—C2—C3	120.2 (3)	C13—C12—H12	120.3
N1—C2—C1	122.2 (3)	C12—C13—C14	118.7 (3)
C3—C2—C1	117.6 (3)	C12—C13—H13	120.7
C8—C3—C4	118.5 (3)	C14—C13—H13	120.7
C8—C3—C2	119.7 (3)	N2—C14—C13	122.6 (3)
C4—C3—C2	121.9 (3)	N2—C14—H14	118.7
O1—C4—C5	119.1 (3)	C13—C14—H14	118.7
O1—C4—C3	123.8 (3)

O1—Cu1—N1—C2	20.2 (3)	C1—C2—C3—C4	149.0 (3)
N3—Cu1—N1—C2	−98.8 (6)	Cu1—O1—C4—C5	−146.9 (2)
N2—Cu1—N1—C2	−163.5 (3)	Cu1ⁱ—O1—C4—C5	94.4 (3)
O1ⁱ—Cu1—N1—C2	105.2 (3)	Cu1—O1—C4—C3	32.9 (4)
O1—Cu1—N1—C9	−153.2 (2)	Cu1ⁱ—O1—C4—C3	−85.7 (3)
N3—Cu1—N1—C9	87.8 (5)	C8—C3—C4—O1	−173.3 (3)
N2—Cu1—N1—C9	23.2 (2)	C2—C3—C4—O1	6.6 (5)
O1ⁱ—Cu1—N1—C9	−68.1 (2)	C8—C3—C4—C5	6.5 (4)
N3—Cu1—N2—C14	−2.0 (3)	C2—C3—C4—C5	−173.6 (3)
N1—Cu1—N2—C14	166.7 (3)	O1—C4—C5—C6	173.6 (3)
O1ⁱ—Cu1—N2—C14	−101.8 (2)	C3—C4—C5—C6	−6.2 (5)
N3—Cu1—N2—C10	177.8 (2)	C4—C5—C6—C7	1.1 (5)
N1—Cu1—N2—C10	−13.5 (2)	C5—C6—C7—C8	3.6 (5)
O1ⁱ—Cu1—N2—C10	78.0 (2)	C6—C7—C8—C3	−3.1 (5)
O1—Cu1—N3—N4	−9.5 (3)	C4—C3—C8—C7	−2.1 (5)
N1—Cu1—N3—N4	109.0 (5)	C2—C3—C8—C7	178.0 (3)
N2—Cu1—N3—N4	172.6 (3)	C2—N1—C9—C10	158.1 (3)
O1ⁱ—Cu1—N3—N4	−95.5 (3)	Cu1—N1—C9—C10	−28.1 (3)
N3—Cu1—O1—C4	129.3 (2)	C14—N2—C10—C11	0.3 (4)
N1—Cu1—O1—C4	−39.7 (2)	Cu1—N2—C10—C11	−179.6 (2)
O1ⁱ—Cu1—O1—C4	−131.4 (2)	C14—N2—C10—C9	−179.4 (3)
N3—Cu1—O1—Cu1ⁱ	−99.33 (9)	Cu1—N2—C10—C9	0.8 (3)
N1—Cu1—O1—Cu1ⁱ	91.64 (8)	N1—C9—C10—N2	17.9 (4)
O1ⁱ—Cu1—O1—Cu1ⁱ	0.0	N1—C9—C10—C11	−161.8 (3)
C9—N1—C2—C3	−178.8 (3)	N2—C10—C11—C12	−0.2 (5)
Cu1—N1—C2—C3	8.5 (4)	C9—C10—C11—C12	179.4 (3)
C9—N1—C2—C1	3.6 (5)	C10—C11—C12—C13	0.5 (5)
Cu1—N1—C2—C1	−169.1 (2)	C11—C12—C13—C14	−0.9 (5)
N1—C2—C3—C8	151.1 (3)	C10—N2—C14—C13	−0.7 (4)
C1—C2—C3—C8	−31.2 (4)	Cu1—N2—C14—C13	179.1 (2)
N1—C2—C3—C4	−28.7 (4)	C12—C13—C14—N2	1.0 (5)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N5ⁱ	0.97	2.55	3.399 (5)	147
C14—H14···N3	0.93	2.55	3.052 (4)	114

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₄H₁₃N₂O)₂(N₃)₂]
M_r	661.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.1066 (12), 8.0545 (10), 16.7027 (18)
β (°)	96.251 (1)
V (Å³)	1351.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.20 × 0.12 × 0.09

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.737, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	6641, 2379, 1720
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.062, 1.02
No. of reflections	2379
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.33

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
C9—H9B···N5ⁱ	0.97	2.55	3.399 (5)	147
C14—H14···N3	0.93	2.55	3.052 (4)	114

Symmetry code: (i) −x, −y+1, −z.

References

Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, m1017–m1019. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pointeau, P., Patin, H., Mousser, A. & le Marouile, J.-Y. (1986). J. Organomet. Chem. 312, 263–276. 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
You, Z.-L. & Zhu, H.-L. (2004). Z. Anorg. Allg. Chem. 630, 2754–2760. Web of Science CSD CrossRef CAS Google Scholar

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Volume 65| Part 9| September 2009| Page m1136

doi:10.1107/S1600536809030475

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