2-[1-(9-Anthrylmeth­yl)-1H-pyrazol-3-yl]pyridine

Zhang, S.-L.; Xie, B.-Y.; Qin, D.-B.

doi:10.1107/S1600536809039427

organic compounds

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Volume 65| Part 11| November 2009| Page o2624

https://doi.org/10.1107/S1600536809039427

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2-[1-(9-Anthrylmethyl)-1H-pyrazol-3-yl]pyridine

Shi-Lu Zhang,^a Bo-Yan Xie ^a and Da-Bin Qin ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 31 August 2009; accepted 28 September 2009; online 3 October 2009)

The title compound, C₂₃H₁₇N₃, can be used in coordination chemistry. The anthracene ring makes dihedral angles of 86.08 (5) and 76.63 (6)°, respectively, with the pyridine and pyrazole rings. The dihedral angle between the pyrazole and pyrimidine rings is 11.79 (7)°. In the structure, weak intermolecular C—H⋯N hydrogen bonds are observed.

Related literature

For the synthesis, see: Amoroso et al. (1994 ); Amir et al. (2008 ); Stell (2005 ); Ward et al. (2001 ). For related structures, see: Liu et al. (2008 ).

Experimental

Crystal data

C₂₃H₁₇N₃
M_r = 335.40
Monoclinic, P 2₁ /c
a = 13.736 (3) Å
b = 13.679 (3) Å
c = 8.913 (2) Å
β = 98.496 (3)°
V = 1656.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.40 × 0.33 × 0.20 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
13094 measured reflections
3777 independent reflections
3156 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.122
S = 1.00
3777 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2ⁱ	0.95	2.55	3.312 (2)	138
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039427/at2873sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039427/at2873Isup2.hkl

checkCIF report

Comment top

In recent years, scientists have paid much attention to the synthetic approach and the structural control of coordination architectures with ligands based on pyrazolyl-pyridine chelating units. (Stell, 2005; Ward et al., 2001). In addition, some pyrazole-derived ligands are useful in medication. (Amir et al., 2008). We report herein the synthesis and crystal structure of the title compound (I). Bond lengths and angles in (I) (Fig. 1) are normal.

The dihedral angles formed by the anthracene ring between pyridine and the pyrazole rings are 86.08 (5)° and 76.63 (6)°, respectively. Pyrazole makes a dihedral angle of 11.79 (7)° with pyridine ring .

Weak intermolecular C—H···N hydrogen bonds between molecules are observed.

Related literature top

For the synthesis, see: Amoroso et al. (1994); Amir et al. (2008); Stell (2005); Ward et al. (2001). For related structures, see: Liu et al. (2008).

Experimental top

The title compound was prepared according to the reported procedure of Amoroso et al. (1994). Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane and pPetroleum ether.

Structure description top

Weak intermolecular C—H···N hydrogen bonds between molecules are observed.

For the synthesis, see: Amoroso et al. (1994); Amir et al. (2008); Stell (2005); Ward et al. (2001). For related structures, see: Liu et al. (2008).

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

2-[1-(9-Anthrylmethyl)-1H-pyrazol-3-yl]pyridine top

Crystal data top

C₂₃H₁₇N₃	F(000) = 704
M_r = 335.40	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4717 reflections
a = 13.736 (3) Å	θ = 3.3–27.5°
b = 13.679 (3) Å	µ = 0.08 mm⁻¹
c = 8.913 (2) Å	T = 93 K
β = 98.496 (3)°	Prism, yellow
V = 1656.2 (7) Å³	0.40 × 0.33 × 0.20 mm
Z = 4

Data collection top

Rigaku SPIDER diffractometer	3156 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −17→17
13094 measured reflections	k = −17→15
3777 independent reflections	l = −11→11

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0596P)² + 0.333P] where P = (F_o² + 2F_c²)/3
3777 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₃H₁₇N₃	V = 1656.2 (7) Å³
M_r = 335.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.736 (3) Å	µ = 0.08 mm⁻¹
b = 13.679 (3) Å	T = 93 K
c = 8.913 (2) Å	0.40 × 0.33 × 0.20 mm
β = 98.496 (3)°

Data collection top

Rigaku SPIDER diffractometer	3156 reflections with I > 2σ(I)
13094 measured reflections	R_int = 0.034
3777 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
3777 reflections	Δρ_min = −0.22 e Å⁻³
235 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
N1	0.25794 (8)	0.55924 (8)	0.72942 (13)	0.0216 (3)
N2	0.22498 (8)	0.64246 (8)	0.78636 (13)	0.0219 (3)
N3	0.02717 (8)	0.65643 (9)	1.01184 (13)	0.0264 (3)
C1	0.46616 (10)	0.43366 (9)	0.66749 (15)	0.0216 (3)
C2	0.51916 (10)	0.47480 (11)	0.80358 (16)	0.0280 (3)
H2	0.4936	0.5309	0.8469	0.034*
C3	0.60559 (11)	0.43505 (11)	0.87224 (17)	0.0313 (4)
H3	0.6392	0.4640	0.9621	0.038*
C4	0.64588 (11)	0.35107 (11)	0.81111 (17)	0.0308 (3)
H4	0.7064	0.3245	0.8595	0.037*
C5	0.59810 (10)	0.30887 (11)	0.68378 (16)	0.0270 (3)
H5	0.6256	0.2526	0.6437	0.032*
C6	0.50709 (10)	0.34731 (10)	0.60844 (15)	0.0229 (3)
C7	0.45791 (10)	0.30295 (10)	0.47849 (16)	0.0241 (3)
H7	0.4848	0.2453	0.4414	0.029*
C8	0.37068 (10)	0.34050 (10)	0.40140 (15)	0.0235 (3)
C9	0.32166 (11)	0.29600 (11)	0.26587 (17)	0.0311 (3)
H9	0.3473	0.2373	0.2304	0.037*
C10	0.23940 (12)	0.33579 (13)	0.18707 (18)	0.0375 (4)
H10	0.2084	0.3053	0.0967	0.045*
C11	0.19940 (11)	0.42289 (12)	0.23918 (17)	0.0341 (4)
H11	0.1421	0.4510	0.1828	0.041*
C12	0.24260 (10)	0.46640 (11)	0.36920 (16)	0.0282 (3)
H12	0.2138	0.5238	0.4034	0.034*
C13	0.33022 (10)	0.42817 (10)	0.45598 (15)	0.0221 (3)
C14	0.37813 (10)	0.47367 (10)	0.58909 (15)	0.0219 (3)
C15	0.33882 (10)	0.56910 (10)	0.63969 (17)	0.0255 (3)
H15A	0.3934	0.6050	0.7008	0.031*
H15B	0.3157	0.6090	0.5488	0.031*
C16	0.20496 (10)	0.48050 (10)	0.76085 (16)	0.0247 (3)
H16	0.2146	0.4149	0.7314	0.030*
C17	0.13437 (10)	0.51320 (10)	0.84353 (16)	0.0251 (3)
H17	0.0859	0.4755	0.8832	0.030*
C18	0.14980 (9)	0.61436 (10)	0.85633 (14)	0.0209 (3)
C19	0.09372 (9)	0.68884 (10)	0.92693 (15)	0.0217 (3)
C20	0.10796 (10)	0.78813 (11)	0.90066 (17)	0.0282 (3)
H20	0.1565	0.8087	0.8419	0.034*
C21	0.05025 (11)	0.85594 (11)	0.96156 (18)	0.0322 (4)
H21	0.0578	0.9238	0.9439	0.039*
C22	−0.01841 (10)	0.82348 (11)	1.04831 (17)	0.0299 (3)
H22	−0.0592	0.8684	1.0914	0.036*
C23	−0.02639 (10)	0.72459 (11)	1.07094 (17)	0.0289 (3)
H23	−0.0730	0.7030	1.1326	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0219 (6)	0.0206 (6)	0.0242 (6)	0.0015 (4)	0.0092 (5)	−0.0014 (5)
N2	0.0204 (6)	0.0214 (6)	0.0252 (6)	0.0009 (4)	0.0069 (5)	−0.0031 (4)
N3	0.0232 (6)	0.0312 (7)	0.0264 (6)	0.0013 (5)	0.0092 (5)	−0.0025 (5)
C1	0.0219 (7)	0.0223 (7)	0.0229 (7)	−0.0025 (5)	0.0104 (5)	0.0026 (5)
C2	0.0295 (8)	0.0317 (8)	0.0247 (7)	−0.0045 (6)	0.0107 (6)	−0.0008 (6)
C3	0.0284 (7)	0.0422 (9)	0.0239 (7)	−0.0092 (6)	0.0056 (6)	0.0022 (6)
C4	0.0225 (7)	0.0422 (9)	0.0285 (8)	0.0003 (6)	0.0066 (6)	0.0119 (6)
C5	0.0240 (7)	0.0290 (8)	0.0299 (8)	0.0032 (6)	0.0106 (6)	0.0086 (6)
C6	0.0226 (7)	0.0238 (7)	0.0248 (7)	0.0013 (5)	0.0117 (6)	0.0055 (5)
C7	0.0255 (7)	0.0208 (7)	0.0285 (7)	0.0009 (5)	0.0122 (6)	−0.0005 (5)
C8	0.0238 (7)	0.0246 (7)	0.0246 (7)	−0.0030 (5)	0.0114 (6)	−0.0013 (6)
C9	0.0298 (8)	0.0344 (8)	0.0314 (8)	−0.0049 (6)	0.0121 (6)	−0.0075 (6)
C10	0.0301 (8)	0.0536 (11)	0.0292 (8)	−0.0096 (7)	0.0059 (7)	−0.0061 (7)
C11	0.0218 (7)	0.0521 (10)	0.0289 (8)	−0.0026 (7)	0.0052 (6)	0.0086 (7)
C12	0.0223 (7)	0.0332 (8)	0.0308 (8)	0.0006 (6)	0.0094 (6)	0.0065 (6)
C13	0.0207 (6)	0.0237 (7)	0.0241 (7)	−0.0012 (5)	0.0105 (5)	0.0034 (5)
C14	0.0219 (6)	0.0212 (7)	0.0250 (7)	0.0000 (5)	0.0114 (5)	0.0019 (5)
C15	0.0254 (7)	0.0234 (7)	0.0312 (7)	0.0010 (5)	0.0153 (6)	0.0006 (6)
C16	0.0270 (7)	0.0203 (7)	0.0286 (7)	−0.0011 (5)	0.0100 (6)	−0.0002 (6)
C17	0.0238 (7)	0.0253 (7)	0.0279 (7)	−0.0007 (5)	0.0094 (6)	0.0015 (6)
C18	0.0194 (6)	0.0250 (7)	0.0185 (6)	0.0008 (5)	0.0035 (5)	−0.0004 (5)
C19	0.0179 (6)	0.0266 (7)	0.0205 (6)	0.0010 (5)	0.0021 (5)	−0.0033 (5)
C20	0.0226 (7)	0.0282 (8)	0.0350 (8)	−0.0020 (6)	0.0082 (6)	−0.0058 (6)
C21	0.0279 (8)	0.0271 (8)	0.0429 (9)	−0.0007 (6)	0.0092 (7)	−0.0080 (6)
C22	0.0224 (7)	0.0318 (8)	0.0362 (8)	0.0033 (6)	0.0072 (6)	−0.0096 (7)
C23	0.0233 (7)	0.0368 (9)	0.0281 (7)	0.0014 (6)	0.0090 (6)	−0.0061 (6)

Geometric parameters (Å, º) top

N1—N2	1.3513 (15)	C10—C11	1.419 (2)
N1—C16	1.3522 (17)	C10—H10	0.9500
N1—C15	1.4678 (17)	C11—C12	1.359 (2)
N2—C18	1.3391 (17)	C11—H11	0.9500
N3—C23	1.3425 (18)	C12—C13	1.4301 (19)
N3—C19	1.3451 (17)	C12—H12	0.9500
C1—C14	1.4144 (19)	C13—C14	1.4132 (19)
C1—C2	1.4342 (19)	C14—C15	1.5069 (19)
C1—C6	1.4407 (19)	C15—H15A	0.9900
C2—C3	1.366 (2)	C15—H15B	0.9900
C2—H2	0.9500	C16—C17	1.3764 (18)
C3—C4	1.418 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.402 (2)
C4—C5	1.353 (2)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.4733 (18)
C5—C6	1.4290 (19)	C19—C20	1.397 (2)
C5—H5	0.9500	C20—C21	1.382 (2)
C6—C7	1.391 (2)	C20—H20	0.9500
C7—C8	1.389 (2)	C21—C22	1.378 (2)
C7—H7	0.9500	C21—H21	0.9500
C8—C9	1.429 (2)	C22—C23	1.374 (2)
C8—C13	1.4365 (19)	C22—H22	0.9500
C9—C10	1.353 (2)	C23—H23	0.9500
C9—H9	0.9500

N2—N1—C16	111.88 (11)	C11—C12—H12	119.1
N2—N1—C15	116.73 (11)	C13—C12—H12	119.1
C16—N1—C15	131.29 (11)	C14—C13—C12	122.90 (13)
C18—N2—N1	104.91 (11)	C14—C13—C8	119.77 (12)
C23—N3—C19	116.69 (13)	C12—C13—C8	117.32 (13)
C14—C1—C2	123.78 (13)	C13—C14—C1	120.16 (12)
C14—C1—C6	119.21 (12)	C13—C14—C15	119.33 (12)
C2—C1—C6	117.00 (12)	C1—C14—C15	120.35 (12)
C3—C2—C1	121.45 (14)	N1—C15—C14	114.65 (11)
C3—C2—H2	119.3	N1—C15—H15A	108.6
C1—C2—H2	119.3	C14—C15—H15A	108.6
C2—C3—C4	120.87 (14)	N1—C15—H15B	108.6
C2—C3—H3	119.6	C14—C15—H15B	108.6
C4—C3—H3	119.6	H15A—C15—H15B	107.6
C5—C4—C3	119.94 (14)	N1—C16—C17	107.18 (12)
C5—C4—H4	120.0	N1—C16—H16	126.4
C3—C4—H4	120.0	C17—C16—H16	126.4
C4—C5—C6	121.28 (14)	C16—C17—C18	104.73 (12)
C4—C5—H5	119.4	C16—C17—H17	127.6
C6—C5—H5	119.4	C18—C17—H17	127.6
C7—C6—C5	120.94 (13)	N2—C18—C17	111.30 (11)
C7—C6—C1	119.61 (12)	N2—C18—C19	119.23 (12)
C5—C6—C1	119.44 (13)	C17—C18—C19	129.41 (12)
C8—C7—C6	121.87 (13)	N3—C19—C20	122.57 (12)
C8—C7—H7	119.1	N3—C19—C18	117.01 (12)
C6—C7—H7	119.1	C20—C19—C18	120.38 (12)
C7—C8—C9	121.67 (13)	C21—C20—C19	118.95 (13)
C7—C8—C13	119.34 (13)	C21—C20—H20	120.5
C9—C8—C13	118.95 (13)	C19—C20—H20	120.5
C10—C9—C8	121.36 (14)	C22—C21—C20	118.93 (14)
C10—C9—H9	119.3	C22—C21—H21	120.5
C8—C9—H9	119.3	C20—C21—H21	120.5
C9—C10—C11	120.12 (14)	C23—C22—C21	118.39 (13)
C9—C10—H10	119.9	C23—C22—H22	120.8
C11—C10—H10	119.9	C21—C22—H22	120.8
C12—C11—C10	120.38 (14)	N3—C23—C22	124.45 (14)
C12—C11—H11	119.8	N3—C23—H23	117.8
C10—C11—H11	119.8	C22—C23—H23	117.8
C11—C12—C13	121.85 (14)

C16—N1—N2—C18	0.52 (15)	C12—C13—C14—C15	−2.84 (19)
C15—N1—N2—C18	177.37 (11)	C8—C13—C14—C15	176.04 (11)
C14—C1—C2—C3	−177.87 (13)	C2—C1—C14—C13	−179.68 (12)
C6—C1—C2—C3	1.33 (19)	C6—C1—C14—C13	1.14 (19)
C1—C2—C3—C4	−0.2 (2)	C2—C1—C14—C15	5.00 (19)
C2—C3—C4—C5	−0.6 (2)	C6—C1—C14—C15	−174.18 (11)
C3—C4—C5—C6	0.1 (2)	N2—N1—C15—C14	175.47 (11)
C4—C5—C6—C7	−179.35 (13)	C16—N1—C15—C14	−8.4 (2)
C4—C5—C6—C1	1.1 (2)	C13—C14—C15—N1	83.96 (15)
C14—C1—C6—C7	−2.08 (19)	C1—C14—C15—N1	−100.67 (15)
C2—C1—C6—C7	178.69 (12)	N2—N1—C16—C17	−0.56 (16)
C14—C1—C6—C5	177.49 (11)	C15—N1—C16—C17	−176.82 (13)
C2—C1—C6—C5	−1.75 (18)	N1—C16—C17—C18	0.35 (15)
C5—C6—C7—C8	−178.37 (12)	N1—N2—C18—C17	−0.28 (15)
C1—C6—C7—C8	1.2 (2)	N1—N2—C18—C19	−177.62 (11)
C6—C7—C8—C9	178.47 (12)	C16—C17—C18—N2	−0.04 (15)
C6—C7—C8—C13	0.6 (2)	C16—C17—C18—C19	176.95 (13)
C7—C8—C9—C10	−176.59 (14)	C23—N3—C19—C20	0.30 (19)
C13—C8—C9—C10	1.3 (2)	C23—N3—C19—C18	−177.46 (12)
C8—C9—C10—C11	−0.6 (2)	N2—C18—C19—N3	−171.91 (12)
C9—C10—C11—C12	−0.7 (2)	C17—C18—C19—N3	11.3 (2)
C10—C11—C12—C13	1.5 (2)	N2—C18—C19—C20	10.27 (19)
C11—C12—C13—C14	178.08 (13)	C17—C18—C19—C20	−166.52 (14)
C11—C12—C13—C8	−0.8 (2)	N3—C19—C20—C21	−1.3 (2)
C7—C8—C13—C14	−1.57 (19)	C18—C19—C20—C21	176.38 (13)
C9—C8—C13—C14	−179.47 (12)	C19—C20—C21—C22	1.0 (2)
C7—C8—C13—C12	177.37 (12)	C20—C21—C22—C23	0.2 (2)
C9—C8—C13—C12	−0.53 (18)	C19—N3—C23—C22	1.0 (2)
C12—C13—C14—C1	−178.22 (12)	C21—C22—C23—N3	−1.3 (2)
C8—C13—C14—C1	0.66 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.95	2.55	3.312 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃
M_r	335.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	13.736 (3), 13.679 (3), 8.913 (2)
β (°)	98.496 (3)
V (Å³)	1656.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.33 × 0.20

Data collection
Diffractometer	Rigaku SPIDER
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13094, 3777, 3156
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.122, 1.00
No. of reflections	3777
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.9500	2.5500	3.312 (2)	138.00

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

Acknowledgements

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of the Sichuan Education Department (grant No. 2006B039).

References

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