3,4-Bis(2-pyrid­yl)-5-(3-pyrid­yl)-4H-1,2,4-triazole

Wu, J.-M.; Guo, W.; Li, C.-P.

doi:10.1107/S1600536811014140

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1189

doi:10.1107/S1600536811014140

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3,4-Bis(2-pyridyl)-5-(3-pyridyl)-4H-1,2,4-triazole

Jing-Min Wu,^a Wei Guo ^a and Cheng-Peng Li ^a ^*

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: tjnulicp@gmail.com

(Received 13 April 2011; accepted 15 April 2011; online 22 April 2011)

In the title molecule, C₁₇H₁₂N₆, the 2-pyridyl rings in the 3- and 4-positions and the 3-pyridyl ring in the 5-position make dihedral angles of 29.78 (16), 67.06 (16) and 32.97 (16)°, respectively, with the triazole group. The dihedral angle between the two 2-pyridyl rings is 65.72 (15)°. The dihedral angles between the 3-pyridyl ring and the two 2-pyridyl rings in the 3- and 4-positions are 61.28 (15) and 63.11 (15)°, respectively. In the crystal, C—H⋯π and π–π interactions [centroid-centroid distance = 3.6248 (19) Å] link the molecules, forming a two-dimensional network.

Related literature

For the synthesis of the title compound, see: Klingele & Brooker (2004 ). For related structures and background references, see: Guo et al. (2010 ); Yang et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₂N₆
M_r = 300.33
Monoclinic, P 2₁ /c
a = 5.7621 (9) Å
b = 15.250 (3) Å
c = 16.640 (3) Å
β = 105.023 (5)°
V = 1412.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.982
6865 measured reflections
2496 independent reflections
1407 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.129
S = 1.08
2496 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the N1/C8–C12 and N6/C13–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2ⁱ	0.93	2.94	3.765 (4)	149
C4—H4⋯Cg4	0.93	2.92	3.616 (3)	133
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014140/su2269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014140/su2269Isup2.hkl

checkCIF report

Comment top

In continuation of our work on tripyridine-substituted triazole derivatives (Guo et al., 2010; Yang et al., 2010), we now describe the synthesis and crystal structure of the title compound. It consists of two 2-pyridyl groups and one 3-pyridyl ring attached to a triazole ring (Fig. 1).

The three pyridyl rings in the 3-, 4-, and 5-positions deviate from the triazole ring by 29.78 (16)°, 67.06 (16)°, and 32.97 (16)°, respectively. The dihedral angle between the two 2-pyridyl groups is 65.72 (15)°. In addition, the dihedral angles between the 3-pyridyl ring and the two 2-pyridyl rings in the 3- and 4-positions are 61.28 (15)° and 63.11 (15)°, respectively.

In the crystal, there exists a π–π interaction involving the 2-pyridyl rings in 3-positions of molecules related by an inversion center [centroid-centroid distance = 3.6248 (19) Å]. The molecular packing is also stabilized by two types of C—H···π interactions; the intramolecular C4—H4···Cg4 [Cg4 is the centroid of pyridine ring (N6/C13-C17)] and the intermolecular C3—H3···Cg2ⁱ [Cg2 is the centroid of pyridine ring (N1/C8-C12)] interactions (see Table 1 and Fig. 2 for details). This leads to the formation of a two-dimensional network.

Related literature top

For the synthesis of the title compound, see: Klingele & Brooker (2004). For related structures and background references, see: Guo et al. (2010); Yang et al. (2010).

Experimental top

The title compound was prepared from a mixture of N-(pyridin-2-yl)pyridine-2-carbothioamide and pyridine-3-carbohydrazide using the method described by Klingele et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title molecule showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view along the a axis of the C—H···π (red dashed lines) and π–π (green dashed lines) interactions in the crystal packing of the title compound (see Table 1 for details).

3,4-Bis(2-pyridyl)-5-(3-pyridyl)-4H-1,2,4-triazole top

Crystal data top

C₁₇H₁₂N₆	F(000) = 624
M_r = 300.33	D_x = 1.413 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1374 reflections
a = 5.7621 (9) Å	θ = 2.5–22.0°
b = 15.250 (3) Å	µ = 0.09 mm⁻¹
c = 16.640 (3) Å	T = 296 K
β = 105.023 (5)°	Block, colourless
V = 1412.2 (4) Å³	0.28 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2496 independent reflections
Radiation source: fine-focus sealed tube	1407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
T_min = 0.975, T_max = 0.982	k = −18→18
6865 measured reflections	l = −19→17

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0385P)² + 0.6358P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2496 reflections	Δρ_max = 0.15 e Å⁻³
209 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (17)

Crystal data top

C₁₇H₁₂N₆	V = 1412.2 (4) Å³
M_r = 300.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7621 (9) Å	µ = 0.09 mm⁻¹
b = 15.250 (3) Å	T = 296 K
c = 16.640 (3) Å	0.28 × 0.22 × 0.20 mm
β = 105.023 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2496 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1407 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.046
6865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.08	Δρ_max = 0.15 e Å⁻³
2496 reflections	Δρ_min = −0.16 e Å⁻³
209 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	0.8676 (5)	0.8964 (2)	0.69324 (16)	0.0620 (8)
N2	0.6880 (5)	0.68510 (18)	0.75149 (15)	0.0531 (7)
N3	0.4816 (5)	0.63917 (17)	0.71292 (16)	0.0525 (7)
N4	0.5220 (4)	0.74876 (16)	0.63138 (13)	0.0402 (6)
N5	−0.2135 (5)	0.57144 (18)	0.56487 (19)	0.0646 (8)
N6	0.6492 (4)	0.79687 (17)	0.51665 (15)	0.0527 (7)
C1	−0.0072 (6)	0.6053 (2)	0.6135 (2)	0.0524 (8)
H1	0.0195	0.6012	0.6710	0.063*
C2	−0.2431 (6)	0.5784 (2)	0.4816 (2)	0.0572 (9)
H2	−0.3822	0.5557	0.4463	0.069*
C3	−0.0776 (6)	0.6174 (2)	0.4471 (2)	0.0585 (9)
H3	−0.1055	0.6206	0.3896	0.070*
C4	0.1285 (5)	0.6514 (2)	0.49739 (19)	0.0479 (8)
H4	0.2420	0.6781	0.4746	0.057*
C5	0.1657 (5)	0.64570 (19)	0.58214 (19)	0.0436 (8)
C6	0.3855 (5)	0.6773 (2)	0.64142 (17)	0.0418 (7)
C7	0.7095 (5)	0.7501 (2)	0.70183 (18)	0.0438 (8)
C8	0.9078 (5)	0.8133 (2)	0.72220 (17)	0.0449 (8)
C9	1.0537 (7)	0.9537 (2)	0.7146 (2)	0.0653 (10)
H9	1.0303	1.0110	0.6951	0.078*
C10	1.2745 (6)	0.9304 (3)	0.7638 (2)	0.0680 (10)
H10	1.3979	0.9715	0.7771	0.082*
C11	1.3130 (6)	0.8464 (3)	0.7933 (2)	0.0639 (10)
H11	1.4620	0.8297	0.8268	0.077*
C12	1.1283 (5)	0.7875 (2)	0.77272 (19)	0.0547 (9)
H12	1.1503	0.7303	0.7925	0.066*
C13	0.4854 (5)	0.80537 (19)	0.55974 (17)	0.0395 (7)
C14	0.2895 (6)	0.8593 (2)	0.5398 (2)	0.0525 (9)
H14	0.1811	0.8621	0.5726	0.063*
C15	0.2599 (7)	0.9094 (2)	0.4689 (2)	0.0685 (11)
H15	0.1300	0.9475	0.4529	0.082*
C16	0.4233 (7)	0.9027 (2)	0.4218 (2)	0.0689 (11)
H16	0.4053	0.9358	0.3737	0.083*
C17	0.6135 (6)	0.8462 (2)	0.4475 (2)	0.0625 (10)
H17	0.7234	0.8417	0.4154	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0686 (19)	0.064 (2)	0.0505 (18)	0.0029 (17)	0.0101 (14)	−0.0032 (15)
N2	0.0565 (17)	0.0589 (18)	0.0425 (15)	0.0064 (15)	0.0106 (13)	0.0061 (14)
N3	0.0548 (17)	0.0546 (18)	0.0482 (17)	0.0043 (14)	0.0133 (14)	0.0059 (14)
N4	0.0393 (14)	0.0462 (15)	0.0344 (14)	0.0038 (12)	0.0082 (11)	0.0007 (12)
N5	0.0652 (19)	0.0567 (19)	0.072 (2)	−0.0041 (15)	0.0186 (17)	−0.0024 (16)
N6	0.0512 (16)	0.0626 (19)	0.0468 (16)	0.0017 (13)	0.0174 (13)	0.0008 (14)
C1	0.059 (2)	0.049 (2)	0.053 (2)	−0.0062 (17)	0.0216 (18)	−0.0058 (16)
C2	0.049 (2)	0.058 (2)	0.060 (2)	0.0030 (17)	0.0076 (18)	−0.0059 (18)
C3	0.054 (2)	0.073 (3)	0.049 (2)	0.0043 (18)	0.0135 (18)	0.0028 (17)
C4	0.0454 (19)	0.054 (2)	0.0474 (19)	−0.0025 (16)	0.0183 (16)	0.0041 (15)
C5	0.0412 (18)	0.0410 (19)	0.0516 (19)	0.0034 (15)	0.0175 (16)	−0.0033 (15)
C6	0.0460 (18)	0.0450 (19)	0.0377 (17)	0.0049 (16)	0.0166 (14)	0.0034 (15)
C7	0.0448 (18)	0.0488 (19)	0.0374 (17)	0.0069 (16)	0.0103 (14)	−0.0016 (16)
C8	0.0463 (18)	0.051 (2)	0.0362 (17)	0.0074 (16)	0.0092 (14)	−0.0033 (15)
C9	0.074 (3)	0.060 (2)	0.057 (2)	−0.011 (2)	0.008 (2)	−0.0068 (18)
C10	0.061 (2)	0.079 (3)	0.064 (2)	−0.018 (2)	0.016 (2)	−0.024 (2)
C11	0.050 (2)	0.074 (3)	0.062 (2)	0.003 (2)	0.0043 (18)	−0.019 (2)
C12	0.052 (2)	0.058 (2)	0.050 (2)	0.0095 (18)	0.0043 (16)	−0.0075 (16)
C13	0.0370 (16)	0.0458 (19)	0.0362 (16)	−0.0002 (15)	0.0105 (14)	−0.0012 (14)
C14	0.0479 (19)	0.059 (2)	0.053 (2)	0.0133 (17)	0.0176 (16)	0.0079 (17)
C15	0.065 (2)	0.068 (3)	0.067 (2)	0.019 (2)	0.008 (2)	0.020 (2)
C16	0.072 (3)	0.081 (3)	0.050 (2)	−0.005 (2)	0.010 (2)	0.022 (2)
C17	0.065 (2)	0.081 (3)	0.047 (2)	−0.014 (2)	0.0237 (18)	0.0002 (19)

Geometric parameters (Å, º) top

N1—C8	1.354 (4)	C4—H4	0.9300
N1—C9	1.357 (4)	C5—C6	1.470 (4)
N2—C7	1.316 (4)	C7—C8	1.467 (4)
N2—N3	1.386 (3)	C8—C12	1.386 (4)
N3—C6	1.311 (3)	C9—C10	1.369 (5)
N4—C7	1.373 (3)	C9—H9	0.9300
N4—C6	1.379 (4)	C10—C11	1.371 (5)
N4—C13	1.442 (3)	C10—H10	0.9300
N5—C2	1.355 (4)	C11—C12	1.366 (4)
N5—C1	1.355 (4)	C11—H11	0.9300
N6—C13	1.331 (3)	C12—H12	0.9300
N6—C17	1.345 (4)	C13—C14	1.367 (4)
C1—C5	1.384 (4)	C14—C15	1.378 (4)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.370 (4)	C15—C16	1.376 (5)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.366 (4)	C16—C17	1.373 (5)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.373 (4)	C17—H17	0.9300

C8—N1—C9	117.3 (3)	N1—C8—C7	118.8 (3)
C7—N2—N3	107.4 (2)	C12—C8—C7	119.3 (3)
C6—N3—N2	107.8 (2)	N1—C9—C10	122.6 (3)
C7—N4—C6	104.8 (2)	N1—C9—H9	118.7
C7—N4—C13	127.7 (2)	C10—C9—H9	118.7
C6—N4—C13	127.4 (2)	C9—C10—C11	119.7 (3)
C2—N5—C1	116.1 (3)	C9—C10—H10	120.2
C13—N6—C17	115.7 (3)	C11—C10—H10	120.2
N5—C1—C5	123.3 (3)	C12—C11—C10	118.8 (3)
N5—C1—H1	118.3	C12—C11—H11	120.6
C5—C1—H1	118.3	C10—C11—H11	120.6
N5—C2—C3	123.1 (3)	C11—C12—C8	119.8 (3)
N5—C2—H2	118.5	C11—C12—H12	120.1
C3—C2—H2	118.5	C8—C12—H12	120.1
C4—C3—C2	119.8 (3)	N6—C13—C14	125.8 (3)
C4—C3—H3	120.1	N6—C13—N4	114.5 (2)
C2—C3—H3	120.1	C14—C13—N4	119.7 (3)
C3—C4—C5	118.9 (3)	C13—C14—C15	116.9 (3)
C3—C4—H4	120.5	C13—C14—H14	121.6
C5—C4—H4	120.5	C15—C14—H14	121.6
C4—C5—C1	118.7 (3)	C16—C15—C14	119.7 (3)
C4—C5—C6	123.1 (3)	C16—C15—H15	120.1
C1—C5—C6	118.2 (3)	C14—C15—H15	120.1
N3—C6—N4	109.9 (3)	C17—C16—C15	118.6 (3)
N3—C6—C5	123.5 (3)	C17—C16—H16	120.7
N4—C6—C5	126.6 (3)	C15—C16—H16	120.7
N2—C7—N4	110.1 (3)	N6—C17—C16	123.4 (3)
N2—C7—C8	123.0 (3)	N6—C17—H17	118.3
N4—C7—C8	126.9 (3)	C16—C17—H17	118.3
N1—C8—C12	121.8 (3)

C7—N2—N3—C6	0.2 (3)	C9—N1—C8—C12	1.0 (4)
C2—N5—C1—C5	0.5 (5)	C9—N1—C8—C7	178.7 (3)
C1—N5—C2—C3	−0.3 (5)	N2—C7—C8—N1	−149.0 (3)
N5—C2—C3—C4	0.0 (5)	N4—C7—C8—N1	30.4 (4)
C2—C3—C4—C5	0.1 (5)	N2—C7—C8—C12	28.8 (4)
C3—C4—C5—C1	0.2 (4)	N4—C7—C8—C12	−151.7 (3)
C3—C4—C5—C6	177.6 (3)	C8—N1—C9—C10	−0.4 (5)
N5—C1—C5—C4	−0.5 (5)	N1—C9—C10—C11	−0.1 (5)
N5—C1—C5—C6	−178.0 (3)	C9—C10—C11—C12	0.0 (5)
N2—N3—C6—N4	−0.7 (3)	C10—C11—C12—C8	0.5 (5)
N2—N3—C6—C5	178.8 (3)	N1—C8—C12—C11	−1.1 (5)
C7—N4—C6—N3	0.8 (3)	C7—C8—C12—C11	−178.8 (3)
C13—N4—C6—N3	176.5 (3)	C17—N6—C13—C14	−0.3 (4)
C7—N4—C6—C5	−178.6 (3)	C17—N6—C13—N4	177.2 (3)
C13—N4—C6—C5	−3.0 (4)	C7—N4—C13—N6	65.1 (4)
C4—C5—C6—N3	−145.5 (3)	C6—N4—C13—N6	−109.6 (3)
C1—C5—C6—N3	31.9 (4)	C7—N4—C13—C14	−117.1 (3)
C4—C5—C6—N4	33.9 (5)	C6—N4—C13—C14	68.2 (4)
C1—C5—C6—N4	−148.7 (3)	N6—C13—C14—C15	−0.2 (5)
N3—N2—C7—N4	0.3 (3)	N4—C13—C14—C15	−177.6 (3)
N3—N2—C7—C8	179.8 (3)	C13—C14—C15—C16	0.5 (5)
C6—N4—C7—N2	−0.7 (3)	C14—C15—C16—C17	−0.4 (5)
C13—N4—C7—N2	−176.3 (3)	C13—N6—C17—C16	0.5 (5)
C6—N4—C7—C8	179.8 (3)	C15—C16—C17—N6	−0.2 (5)
C13—N4—C7—C8	4.2 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the N1/C8–C12 and N6/C13–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2ⁱ	0.93	2.94	3.765 (4)	149
C4—H4···Cg4	0.93	2.92	3.616 (3)	133

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₆
M_r	300.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.7621 (9), 15.250 (3), 16.640 (3)
β (°)	105.023 (5)
V (Å³)	1412.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	6865, 2496, 1407
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.129, 1.08
No. of reflections	2496
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the N1/C8–C12 and N6/C13–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2ⁱ	0.93	2.94	3.765 (4)	149
C4—H4···Cg4	0.93	2.92	3.616 (3)	133

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

Acknowledgements

This work was supported financially by Tianjin Normal University (52X09004).

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, W., Yang, Y.-Y. & Du, M. (2010). Inorg. Chem. Commun. 13 863–866. Web of Science CSD CrossRef CAS Google Scholar
Klingele, M. H. & Brooker, S. (2004). Eur. J. Org. Chem. pp. 3422–3434. Web of Science CSD CrossRef Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, Y.-Y., Guo, W. & Du, M. (2010). Inorg. Chem. Commun. 13 1195–1198. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 5| May 2011| Page o1189

doi:10.1107/S1600536811014140

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