trans-Bis(N′-isopropyl­idene­benzo­hydrazidato-κ2N′,O)bis­(pyridine-κN)nickel(II)

Zheng, C.-Z.; Wang, L.; Liu, J.

doi:10.1107/S1600536811024214

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m978

doi:10.1107/S1600536811024214

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trans-Bis(N′-isopropylidenebenzohydrazidato-κ²N′,O)bis(pyridine-κN)nickel(II)

Chang-Zheng Zheng,^a Liang Wang ^a ^* and Juan Liu ^a

^aCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China
^*Correspondence e-mail: wllily315668256@yahoo.com.cn

(Received 10 June 2011; accepted 20 June 2011; online 25 June 2011)

The complex molecule of the title compound, [Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂], has a crystallographically imposed centre of symmetry. The Ni^II atom is coordinated in a distorted octahedral geometry by the O and N atoms of two trans arranged anionic bidentate hydrazone ligands forming the equatorial plane and by the N atoms of two pyridine molecules at the axial positions. In the crystal, intermolecular C—H⋯N hydrogen bonds link the molecules into columns parallel to the b axis.

Related literature

For the biological and coordination properties of aroylhydrazones, see: Ali et al. (2004 ); Carcelli et al. (1995 ); Cheng et al. (1996 ); Zhang et al. (2011 ).

Experimental

Crystal data

[Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂]
M_r = 567.33
Monoclinic, C 2/c
a = 15.419 (5) Å
b = 9.242 (3) Å
c = 21.295 (9) Å
β = 109.924 (5)°
V = 2853.1 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 298 K
0.23 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.852, T_max = 0.919
7093 measured reflections
2514 independent reflections
2285 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.078
S = 1.10
2514 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N1ⁱ	0.93	2.50	3.382 (3)	157
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT; 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/S1600536811024214/rz2613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024214/rz2613Isup2.hkl

checkCIF report

Comment top

Hydrazones are an important class of Schiff bases compounds which has attracted much attention because of their biological activities (Carcelli et al., 1995), chemical and industrial versatility, and strong tendency to chelate to transition metals (Zhang et al., 2011; Ali et al., 2004; Cheng et al., 1996). As an extension of our work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.

In the title compound, the complex molecule has crystallographically imposed centre of symmetry (Fig. 1). The coordination polyhedron about the nickel metal is distorted octahedral, with the N, O atoms of two trans-arranged anionic bidentate hydrazone ligands at the equatorial plane and by the N atoms of two pyridine molecules occupying the axial positions. In the crystal structure, complex molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1) into columns parallel to the b axis.

Related literature top

For the biological and coordination properties of aroylhydrazones, see: Ali et al. (2004); Carcelli et al. (1995); Cheng et al. (1996); Zhang et al. (2011).

Experimental top

Ethyl benzoate (6.00 g, 0.04 mol) was dissolved in ethnol (30 ml) at room temperature and heated at 363 K, followed by the addition of hydrazine hydrate (2.40 g, 0.048 mol). Subsequently, the mixture was refluxed for 9 h, and then cooled to room temperature. The crystals precipitated were collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to give benzoylhydrazine. Benzoylhydrazine (3.40 g, 0.025 mol) was dissolved in ethanol (20 ml) at room temperature and heated at 363 K, followed by the addition of dimethyl ketone (1.45 g, 0.025 mol). Subsequently, the mixture was refluxed for 10 h, and then cooled to room temperature. The solid phase precipitated was collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to give N'-[(E)- dimethylketone]-benzohydrazide. A mixture of N'-[(E)-dimethylketone]-benzohydrazide (0.018 g, 0.10 mmol), NiC_l2.6H₂O (0.024 g, 0.10 mmol), pyridine (0.0079 g, 0.10 mmol), H₂O (5.00 ml) and several drop of methanol was placed in a Parr Teflon-lined stainless steel vessel (25 ml), and then the vessel was sealed and heated at 393 K for 3 d. After the mixture was slowly cooled to room temperature, red crystals suitable for X-ray analysis were obtained (yield 37%).

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); 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 molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. Symmetry code: (A) -x, 1-y, -z.

trans-Bis(N'-isopropylidenebenzohydrazidato- κ²N',O)bis(pyridine-κN)nickel(II) top

Crystal data top

[Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂]	F(000) = 1192
M_r = 567.33	D_x = 1.321 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5423 reflections
a = 15.419 (5) Å	θ = 2.6–28.5°
b = 9.242 (3) Å	µ = 0.72 mm⁻¹
c = 21.295 (9) Å	T = 298 K
β = 109.924 (5)°	Block, red
V = 2853.1 (18) Å³	0.23 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2514 independent reflections
Radiation source: fine-focus sealed tube	2285 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→16
T_min = 0.852, T_max = 0.919	k = −10→8
7093 measured reflections	l = −24→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0334P)² + 2.5175P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2514 reflections	Δρ_max = 0.24 e Å⁻³
178 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (15)

Crystal data top

[Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂]	V = 2853.1 (18) Å³
M_r = 567.33	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.419 (5) Å	µ = 0.72 mm⁻¹
b = 9.242 (3) Å	T = 298 K
c = 21.295 (9) Å	0.23 × 0.14 × 0.12 mm
β = 109.924 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2514 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2285 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.919	R_int = 0.019
7093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.10	Δρ_max = 0.24 e Å⁻³
2514 reflections	Δρ_min = −0.32 e Å⁻³
178 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
Ni1	0.0000	0.5000	0.0000	0.03337 (12)
O1	0.12440 (8)	0.44811 (14)	0.06671 (6)	0.0385 (3)
N1	0.04126 (10)	0.34430 (16)	0.12653 (8)	0.0393 (4)
N2	−0.03583 (10)	0.40836 (16)	0.07882 (7)	0.0375 (3)
N3	0.00804 (10)	0.71169 (16)	0.04278 (7)	0.0383 (3)
C1	0.28411 (15)	0.3172 (3)	0.14883 (12)	0.0636 (6)
H1	0.2865	0.3759	0.1140	0.076*
C2	0.36373 (18)	0.2488 (4)	0.18906 (15)	0.0871 (9)
H2	0.4190	0.2619	0.1812	0.104*
C3	0.36080 (19)	0.1624 (3)	0.23998 (14)	0.0788 (8)
H3	0.4138	0.1154	0.2668	0.095*
C4	0.27956 (18)	0.1450 (3)	0.25151 (12)	0.0665 (7)
H4	0.2775	0.0861	0.2864	0.080*
C5	0.20085 (15)	0.2138 (2)	0.21199 (10)	0.0504 (5)
H5	0.1462	0.2020	0.2208	0.061*
C6	0.20201 (13)	0.2999 (2)	0.15964 (9)	0.0397 (4)
C7	0.11672 (12)	0.37097 (18)	0.11420 (9)	0.0348 (4)
C8	−0.11104 (14)	0.3927 (2)	0.09097 (10)	0.0474 (5)
C9	−0.11699 (18)	0.3144 (3)	0.15068 (13)	0.0741 (8)
H9A	−0.1454	0.2217	0.1373	0.111*
H9B	−0.1534	0.3699	0.1707	0.111*
H9C	−0.0561	0.3012	0.1825	0.111*
C10	−0.19837 (15)	0.4545 (3)	0.04456 (13)	0.0654 (6)
H10A	−0.1871	0.4978	0.0071	0.098*
H10B	−0.2210	0.5267	0.0675	0.098*
H10C	−0.2434	0.3790	0.0291	0.098*
C11	0.08853 (14)	0.7625 (2)	0.08221 (11)	0.0529 (5)
H11	0.1406	0.7046	0.0902	0.063*
C12	0.09888 (16)	0.8958 (2)	0.11177 (13)	0.0646 (6)
H12	0.1566	0.9265	0.1397	0.078*
C13	0.02369 (17)	0.9830 (2)	0.09987 (12)	0.0551 (6)
H13	0.0289	1.0742	0.1193	0.066*
C14	−0.05893 (15)	0.9331 (2)	0.05897 (12)	0.0554 (5)
H14	−0.1115	0.9902	0.0496	0.066*
C15	−0.06440 (14)	0.7977 (2)	0.03149 (11)	0.0497 (5)
H15	−0.1216	0.7648	0.0037	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02844 (18)	0.03087 (18)	0.03696 (19)	0.00162 (12)	0.00618 (13)	0.00258 (13)
O1	0.0330 (6)	0.0372 (7)	0.0409 (7)	0.0014 (5)	0.0068 (5)	0.0065 (6)
N1	0.0378 (8)	0.0370 (8)	0.0406 (8)	0.0051 (7)	0.0101 (7)	0.0043 (7)
N2	0.0345 (8)	0.0331 (8)	0.0427 (8)	0.0019 (6)	0.0106 (7)	0.0009 (6)
N3	0.0373 (8)	0.0346 (8)	0.0404 (8)	−0.0003 (7)	0.0099 (7)	0.0009 (6)
C1	0.0458 (12)	0.0827 (17)	0.0591 (14)	0.0196 (12)	0.0138 (10)	0.0214 (12)
C2	0.0473 (14)	0.126 (3)	0.0819 (19)	0.0321 (16)	0.0147 (13)	0.0277 (19)
C3	0.0627 (16)	0.0872 (19)	0.0689 (17)	0.0342 (14)	−0.0003 (13)	0.0178 (14)
C4	0.0732 (17)	0.0562 (14)	0.0525 (13)	0.0089 (12)	−0.0014 (12)	0.0165 (11)
C5	0.0527 (12)	0.0444 (11)	0.0458 (11)	0.0008 (10)	0.0061 (9)	0.0033 (9)
C6	0.0409 (10)	0.0333 (9)	0.0375 (10)	0.0046 (8)	0.0039 (8)	−0.0028 (7)
C7	0.0371 (9)	0.0268 (9)	0.0354 (9)	0.0020 (7)	0.0059 (7)	−0.0035 (7)
C8	0.0410 (10)	0.0492 (11)	0.0549 (12)	0.0033 (9)	0.0201 (9)	0.0051 (9)
C9	0.0614 (15)	0.094 (2)	0.0782 (17)	0.0140 (14)	0.0386 (13)	0.0308 (15)
C10	0.0394 (11)	0.0851 (17)	0.0734 (16)	0.0077 (12)	0.0213 (11)	0.0201 (14)
C11	0.0404 (11)	0.0412 (11)	0.0693 (14)	0.0015 (9)	0.0087 (10)	−0.0077 (10)
C12	0.0497 (13)	0.0499 (13)	0.0834 (17)	−0.0085 (10)	0.0086 (12)	−0.0191 (12)
C13	0.0625 (14)	0.0358 (11)	0.0698 (15)	−0.0047 (10)	0.0261 (12)	−0.0104 (10)
C14	0.0507 (12)	0.0463 (12)	0.0691 (14)	0.0106 (10)	0.0204 (11)	−0.0057 (11)
C15	0.0387 (10)	0.0480 (11)	0.0577 (12)	0.0028 (9)	0.0104 (9)	−0.0089 (10)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	2.0175 (13)	C5—C6	1.374 (3)
Ni1—O1	2.0175 (13)	C5—H5	0.9300
Ni1—N2	2.1148 (16)	C6—C7	1.493 (2)
Ni1—N2ⁱ	2.1148 (16)	C8—C10	1.486 (3)
Ni1—N3	2.1439 (16)	C8—C9	1.493 (3)
Ni1—N3ⁱ	2.1439 (16)	C9—H9A	0.9600
O1—C7	1.275 (2)	C9—H9B	0.9600
N1—C7	1.301 (2)	C9—H9C	0.9600
N1—N2	1.404 (2)	C10—H10A	0.9600
N2—C8	1.279 (2)	C10—H10B	0.9600
N3—C15	1.325 (2)	C10—H10C	0.9600
N3—C11	1.325 (2)	C11—C12	1.368 (3)
C1—C6	1.371 (3)	C11—H11	0.9300
C1—C2	1.387 (3)	C12—C13	1.363 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.360 (4)	C13—C14	1.356 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.366 (4)	C14—C15	1.372 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.375 (3)	C15—H15	0.9300
C4—H4	0.9300

O1ⁱ—Ni1—O1	180.00 (9)	C4—C5—H5	119.6
O1ⁱ—Ni1—N2	102.19 (6)	C1—C6—C5	118.16 (19)
O1—Ni1—N2	77.81 (6)	C1—C6—C7	119.95 (18)
O1ⁱ—Ni1—N2ⁱ	77.81 (6)	C5—C6—C7	121.87 (18)
O1—Ni1—N2ⁱ	102.19 (6)	O1—C7—N1	126.67 (16)
N2—Ni1—N2ⁱ	180.00 (8)	O1—C7—C6	117.41 (16)
O1ⁱ—Ni1—N3	89.18 (6)	N1—C7—C6	115.89 (16)
O1—Ni1—N3	90.82 (6)	N2—C8—C10	120.02 (18)
N2—Ni1—N3	91.21 (6)	N2—C8—C9	123.37 (19)
N2ⁱ—Ni1—N3	88.79 (6)	C10—C8—C9	116.61 (18)
O1ⁱ—Ni1—N3ⁱ	90.82 (6)	C8—C9—H9A	109.5
O1—Ni1—N3ⁱ	89.18 (6)	C8—C9—H9B	109.5
N2—Ni1—N3ⁱ	88.79 (6)	H9A—C9—H9B	109.5
N2ⁱ—Ni1—N3ⁱ	91.21 (6)	C8—C9—H9C	109.5
N3—Ni1—N3ⁱ	180.00 (8)	H9A—C9—H9C	109.5
C7—O1—Ni1	111.61 (11)	H9B—C9—H9C	109.5
C7—N1—N2	111.65 (14)	C8—C10—H10A	109.5
C8—N2—N1	114.09 (16)	C8—C10—H10B	109.5
C8—N2—Ni1	134.88 (14)	H10A—C10—H10B	109.5
N1—N2—Ni1	110.93 (11)	C8—C10—H10C	109.5
C15—N3—C11	116.89 (17)	H10A—C10—H10C	109.5
C15—N3—Ni1	123.21 (13)	H10B—C10—H10C	109.5
C11—N3—Ni1	119.90 (13)	N3—C11—C12	123.2 (2)
C6—C1—C2	121.1 (2)	N3—C11—H11	118.4
C6—C1—H1	119.5	C12—C11—H11	118.4
C2—C1—H1	119.5	C13—C12—C11	119.3 (2)
C3—C2—C1	119.8 (3)	C13—C12—H12	120.4
C3—C2—H2	120.1	C11—C12—H12	120.4
C1—C2—H2	120.1	C14—C13—C12	118.2 (2)
C2—C3—C4	119.6 (2)	C14—C13—H13	120.9
C2—C3—H3	120.2	C12—C13—H13	120.9
C4—C3—H3	120.2	C13—C14—C15	119.5 (2)
C3—C4—C5	120.5 (2)	C13—C14—H14	120.3
C3—C4—H4	119.7	C15—C14—H14	120.3
C5—C4—H4	119.7	N3—C15—C14	123.00 (19)
C6—C5—C4	120.8 (2)	N3—C15—H15	118.5
C6—C5—H5	119.6	C14—C15—H15	118.5

N2—Ni1—O1—C7	9.82 (11)	C3—C4—C5—C6	0.8 (4)
N2ⁱ—Ni1—O1—C7	−170.18 (11)	C2—C1—C6—C5	0.7 (4)
N3—Ni1—O1—C7	100.88 (12)	C2—C1—C6—C7	−178.0 (2)
N3ⁱ—Ni1—O1—C7	−79.12 (12)	C4—C5—C6—C1	−1.2 (3)
C7—N1—N2—C8	−175.97 (16)	C4—C5—C6—C7	177.42 (19)
C7—N1—N2—Ni1	7.01 (17)	Ni1—O1—C7—N1	−10.2 (2)
O1ⁱ—Ni1—N2—C8	−5.3 (2)	Ni1—O1—C7—C6	168.00 (12)
O1—Ni1—N2—C8	174.7 (2)	N2—N1—C7—O1	1.9 (2)
N3—Ni1—N2—C8	84.12 (19)	N2—N1—C7—C6	−176.30 (14)
N3ⁱ—Ni1—N2—C8	−95.88 (19)	C1—C6—C7—O1	−0.9 (3)
O1ⁱ—Ni1—N2—N1	170.85 (10)	C5—C6—C7—O1	−179.55 (17)
O1—Ni1—N2—N1	−9.15 (10)	C1—C6—C7—N1	177.46 (19)
N3—Ni1—N2—N1	−99.72 (11)	C5—C6—C7—N1	−1.2 (3)
N3ⁱ—Ni1—N2—N1	80.28 (11)	N1—N2—C8—C10	−179.78 (19)
O1ⁱ—Ni1—N3—C15	16.25 (16)	Ni1—N2—C8—C10	−3.7 (3)
O1—Ni1—N3—C15	−163.75 (16)	N1—N2—C8—C9	0.4 (3)
N2—Ni1—N3—C15	−85.93 (16)	Ni1—N2—C8—C9	176.48 (18)
N2ⁱ—Ni1—N3—C15	94.07 (16)	C15—N3—C11—C12	1.2 (3)
O1ⁱ—Ni1—N3—C11	−163.18 (16)	Ni1—N3—C11—C12	−179.37 (19)
O1—Ni1—N3—C11	16.82 (16)	N3—C11—C12—C13	−1.0 (4)
N2—Ni1—N3—C11	94.64 (16)	C11—C12—C13—C14	0.2 (4)
N2ⁱ—Ni1—N3—C11	−85.36 (16)	C12—C13—C14—C15	0.4 (4)
C6—C1—C2—C3	0.3 (5)	C11—N3—C15—C14	−0.5 (3)
C1—C2—C3—C4	−0.7 (5)	Ni1—N3—C15—C14	−179.99 (17)
C2—C3—C4—C5	0.1 (4)	C13—C14—C15—N3	−0.2 (4)

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
C13—H13···N1ⁱⁱ	0.93	2.50	3.382 (3)	157

Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂]
M_r	567.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	15.419 (5), 9.242 (3), 21.295 (9)
β (°)	109.924 (5)
V (Å³)	2853.1 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.23 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.852, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	7093, 2514, 2285
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.078, 1.10
No. of reflections	2514
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.32

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), 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
C13—H13···N1ⁱ	0.93	2.50	3.382 (3)	157

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors thank the National Natural Science Foundation of Shaanxi Province, China (2009JM2012) for financial support.

References

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