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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Pages o999-o1000
doi:10.1107/S1600536809012148

1-(3-Bromo­prop­yl)-4-(2-pyrid­yl)-1H-1,2,3-triazole

James D. Crowley,a* Pauline H. Bandeena and Lyall R. Hantona

aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
*Correspondence e-mail: jcrowley@chemistry.otago.ac.nz

(Received 20 March 2009; accepted 1 April 2009; online 8 April 2009)

In the structure of the title compound, C10H11BrN4, the plane of the substituted 1,2,3-triazole ring is tilted by 14.84 (10)° with respect to the mean plane of the pyridine ring. The pyridine and closest triazole N atoms adopt an anti arrangement which removes any lone pair–lone pair repulsions between the N atoms. This conformation is further stabilized by weak intermolecular C—H⋯N inter­actions. There are two mol­ecules in the unit cell, which form a centrosymmetric head-to-tail dimer. The dimers are stabilized through π–π inter­actions [centroid–centroid distance = 3.733 (4) Å and mean inter­planar distance = 3.806 (12) Å] between the substituted 1,2,3-triazole ring and the pyridine rings in adjacent mol­ecules. Each dimer inter­acts with two neighbouring dimers above and below, forming a slipped stack of dimers through the crystal. The 3-bromo­propyl chain sits over the pyridine ring of a neighbouring mol­ecule and the triazole rings of nearby mol­ecules are adjacent.

Related literature

For details of the Cu(I)-catalysed 1,3-cyclo­addition of organic azides with terminal alkynes, see: Rostovtsev et al. (2002[Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. (2002). Angew. Chem. Int. Ed. 41, 2596-2599.]); Tornoe et al. (2002[Tornoe, C. W., Christensen, C. & Meldal, M. (2002). J. Org. Chem. 67, 3057-3064.]); Meldal & Tornoe (2008[Meldal, M. & Tornoe, C. W. (2008). Chem. Rev. 108, 2952-3015.]). For applications of pyridyl-functionalized 1,2,3-triazoles, see: Li & Flood (2008[Li, Y. & Flood, A. H. (2008). Angew. Chem. Int. Ed. 47, 2649-2652.]); Meudtner & Hecht (2008[Meudtner, R. M. & Hecht, S. (2008). Angew. Chem. Int. Ed. 47, 4926-4930.]); Krivopalov & Shkurko (2005[Krivopalov, V. P. & Shkurko, O. P. (2005). Russ. Chem. Rev. 74, 339-379.]); Li et al. (2007[Li, Y., Huffman, J. C. & Flood, A. H. (2007). Chem. Commun. pp. 2692-2694.]); Richardson et al. (2008[Richardson, C., Fitchett, C. M., Keene, F. R. & Steel, P. J. (2008). Dalton Trans. pp. 2534-2537.]). For related structures, see Schweinfurth et al. (2008[Schweinfurth, D., Hardcastle, K. I. & Bunz, U. H. F. (2008). Chem. Commun. pp. 2203-2205.]); Obata et al. (2008[Obata, M., Kitamura, A., Mori, A., Kameyama, C., Czaplewska, J. A., Tanaka, R., Kinoshita, I., Kusumoto, T., Hashimoto, H., Harada, M., Mikata, Y., Funabikig, T. & Yano, S. (2008). Dalton Trans. pp. 3292-3300.]).

[Scheme 1]

Experimental

Crystal data

  • C10H11BrN4

  • Mr = 267.14

  • Triclinic, [P \overline 1]

  • a = 5.658 (2) Å

  • b = 9.688 (4) Å

  • c = 10.191 (4) Å

  • α = 84.498 (3)°

  • β = 85.663 (2)°

  • γ = 83.854 (2)°

  • V = 551.6 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.70 mm−1

  • T = 90 K

  • 0.53 × 0.23 × 0.11 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.358, Tmax = 0.66

  • 8776 measured reflections

  • 1879 independent reflections

  • 1759 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.071

  • S = 0.97

  • 1879 reflections

  • 136 parameters

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7⋯N2i 0.93 2.62 3.449 (4) 149
C10—H10B⋯N1ii 0.97 2.51 3.450 (4) 164
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Bruno et al., 2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012148/fj2204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012148/fj2204Isup2.hkl

checkCIF report


Comment top

The Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes (the CuAAC reaction) (Rostovtsev et al. 2002; Tornoe et al. 2002) has quickly become an indispensable tool for functional molecule synthesis and renewed interest in the chemistry of functionalized 1,2,3-triazoles (Meldal & Tornoe, 2008). Because they are readily synthesized using the CuAAC reaction, pyridyl functionalized 1,2,3-triazoles have begun attracting significant attention in a range of areas including anion recognition (Li & Flood, 2008), stimuli responsive foldamers (Meudtner & Hecht, 2008), drug discovery (Krivopalov & Shkurko, 2005) and coordination chemistry (Li et al. 2007; Richardson et al., 2008; Schweinfurth et al., 2008; Obata et al., 2008)

The molecular structure of the new triazole compound 1 is shown in Fig. 1. The molecule consists of an essentially co-planar (2-pyridyl) and 1,2,3-triazole units attached to a 3-bromopropyl chain, the plane of the substituted 1,2,3-triazole ring is tilted by 14.84 (10)° with respect to the mean plane of the pyridine ring system. As is commonly observed (Obata et al., 2008; Schweinfurth et al., 2008) N1 in the pyridine ring and N2 of the triazole ring adopt an anti arrangement which removes any lone pair-lone pair repulsions between the nitrogen atoms. Additionally, the anti conformation is stabilized by weak C—H···N interactions. There are two molecules of 1 in the unit cell which form a centrosymmetric head to tail dimer that is stabilized through a π-π interaction [centroid-centroid distance = 3.733 (4) Å, mean interplanar distance 3.806 (12) Å] between the substituted 1,2,3-triazole and the pyridine rings in adjacent molecules. In the extended crystal each dimer interacts with two neighbouring dimers above and below to form slipped stacks of dimers through the crystal. The 3-bromopropyl chain sits over the pyridine ring of the neighbouring molecule and the triazole rings of nearby molecules are adjacent [centroid-centroid distance = 4.691 (4) Å]. Unlike the dimer units, the extended stacks appear not to be stabilized by π-π interactions, the mean interplanar distance between dimers of 1 is 4.060 Å are outside the range normally expected for a π-π interaction. A steric interaction between the bromopropyl chain on one molecule of 1 and the pyridine ring on the adjacent molecule in the next dimer prevents a closer face to face interaction of the aromatic rings in the different dimer units.

Related literature top

For details of the Cu(I)-catalysed 1,3-cycloaddition of organic azides with terminal alkynes, see: Rostovtsev et al. (2002); Tornoe et al. (2002); Meldal & Tornoe (2008). For applications of pyridyl-functionalized 1,2,3-triazoles, see: Li & Flood (2008); Meudtner & Hecht (2008); Krivopalov & Shkurko (2005); Li et al. (2007); Richardson et al. (2008). For related structures, see Schweinfurth et al. (2008); Obata et al. (2008).

Experimental top

The title compound, C10H11BrN4 (1) was obtained as a by-product during the attempted synthesis of a ditopic propyl bridged bis((2-pyridyl)-1,2,3-triazole) ligand. X-ray quality colourless crystals were obtained by slow evaporation of a petroleum ether solution of 1 but were weakly diffracting.

To a stirred solution of 1,3-dibromopropane (0.301 g, 1.5 mmol, 1.00 eq.) in DMF/H2O (15 ml, 4:1) was added NaN3 (0.205 g, 3.1 mmol, 2.05 eq.), Na2CO3 (0.13 g, 1.2 mmol, 0.8 eq.), CuSO4.5H2O (0.150 g, 0.6 mmol, 0.40 eq.), ascorbic acid (0.210 g, 1.2 mmol, 0.80 eq). 2-Ethynylpyridine (0.323 g, 3.1 mmol, 2.05 eq.) was added and the reaction mixture was stirred at room temperature for 20 h. The resulting suspension was then partitioned between aqueous NH4OH/edta (1 M, 100 ml) and CH2Cl2 (50 ml) and the layers separated. The organic phase was washed with H2O (100 ml) and brine (100 ml), dried (MgSO4) and the solvent removed under reduced pressure. Chromatography (gradient CH2Cl2/acetone to a ratio 9:1) gave the product as a white solid. Yield: 0.190 g, 47%. Mp 89–91 °C; 1H NMR (300 MHz, CDCl3) δ 8.58 (ddd, J = 0.9, J = 1.7, J = 4.9, 1H, H1), 8.23–8.12 (m, 2H, H4,5), 7.78 (td, J = 1.8, J = 7.8, 1H, H3), 7.26–7.21 (m, 1H, H2), 4.62 (t, J = 6.5, 2H, H10), 3.40 (t, J = 6.2, 2H, H8), 2.52 (p, J = 6.4, 2H, H9); 13C NMR (75 MHz, CDCl3) δ: 150.2, 149.5, 148.5, 136.9, 122.9, 122.6, 120.3, 48.3, 32.7, 29.3; I.R. (KBr): ν(cm-1) 3400–3200 (br), 3116, 3087, 2924, 1701, 1617, 1607, 1598, 1572, 1548, 1473, 1466, 1447, 1421, 1358, 1317, 1287, 1250, 1224, 1204, 1144, 1080, 1048, 983, 969, 891, 855, 844, 826, 786, 744, 708; HRESI-MS (MeOH): m/z = 289.0066 [M+Na]+ (calc. for C10H1179BrN4Na 289.0065 [M+Na]+), 291.0040 [M+Na]+ (calc. for C10H1181BrN4Na 291.0044 [M+Na]+; Anal. calcd for C10H11BrN4(H2O): C, 44.96; H, 4.15; N, 20.97; Found: C, 45.36; H, 4.24; N, 21.03.

Refinement top

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for the CH H atoms and d(C—H) = 0.97 Å, Uiso = 1.2Ueq (C) for CH2 H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound 1, showing the atom numbering scheme. The thermal displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A spacefilling representation of the unit cell of 1 showing the head-to-tail stacking of the molecules.
[Figure 3] Fig. 3. A spacefilling representation of the crystal packing present in 1, showing the slipped stacks of the dimers.
1-(3-Bromopropyl)-4-(2-pyridyl)-1H-1,2,3-triazole top
Crystal data top
C10H11BrN4Z = 2
Mr = 267.14F(000) = 268
Triclinic, P1Dx = 1.608 Mg m−3
Hall symbol: -P 1Melting point: 362 K
a = 5.658 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.688 (4) ÅCell parameters from 5048 reflections
c = 10.191 (4) Åθ = 3.1–33.3°
α = 84.498 (3)°µ = 3.70 mm−1
β = 85.663 (2)°T = 90 K
γ = 83.854 (2)°Irregular, colourless
V = 551.6 (4) Å30.53 × 0.23 × 0.11 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1879 independent reflections
Radiation source: fine-focus sealed tube1759 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 25.0°, θmin = 4.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −6→6
Tmin = 0.358, Tmax = 0.66k = −11→11
8776 measured reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0372P)2 + 0.5592P]
where P = (Fo2 + 2Fc2)/3
1879 reflections(Δ/σ)max = 0.001
136 parametersΔρmax = 0.64 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Crystal data top
C10H11BrN4γ = 83.854 (2)°
Mr = 267.14V = 551.6 (4) Å3
Triclinic, P1Z = 2
a = 5.658 (2) ÅMo Kα radiation
b = 9.688 (4) ŵ = 3.70 mm−1
c = 10.191 (4) ÅT = 90 K
α = 84.498 (3)°0.53 × 0.23 × 0.11 mm
β = 85.663 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1879 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		1759 reflections with I > 2σ(I)
Tmin = 0.358, Tmax = 0.66Rint = 0.043
8776 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 0.97Δρmax = 0.64 e Å−3
1879 reflectionsΔρmin = −0.61 e Å−3
136 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
xyzUiso*/Ueq
Br10.84285 (5)−0.19395 (3)0.97535 (3)0.03839 (13)
N30.3211 (3)0.1602 (2)0.6731 (2)0.0243 (4)
C60.4287 (4)0.2879 (2)0.4946 (2)0.0177 (5)
N20.2396 (4)0.2401 (2)0.5713 (2)0.0236 (4)
N10.6005 (4)0.4000 (2)0.2965 (2)0.0230 (4)
N40.5611 (3)0.15753 (19)0.66118 (19)0.0188 (4)
C50.3999 (4)0.3838 (2)0.3747 (2)0.0179 (5)
C70.6350 (4)0.2341 (2)0.5518 (2)0.0185 (5)
H70.79080.24760.52150.022*
C40.1805 (4)0.4545 (2)0.3468 (2)0.0216 (5)
H40.04470.43850.40100.026*
C80.7073 (4)0.0790 (2)0.7608 (2)0.0212 (5)
H8A0.60750.05760.84030.025*
H8B0.82670.13600.78320.025*
C20.3717 (5)0.5674 (2)0.1552 (2)0.0244 (5)
H20.36770.63020.08020.029*
C10.5814 (4)0.4892 (2)0.1884 (2)0.0249 (5)
H10.71700.49930.13220.030*
C90.8298 (5)−0.0555 (3)0.7124 (2)0.0291 (6)
H9A0.7101−0.11680.70020.035*
H9B0.9133−0.03490.62730.035*
C30.1681 (4)0.5495 (2)0.2364 (2)0.0242 (5)
H30.02450.60080.21720.029*
C101.0035 (5)−0.1294 (3)0.8062 (3)0.0309 (6)
H10A1.1188−0.06670.82220.037*
H10B1.0890−0.20870.76630.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04089 (19)0.03674 (19)0.03195 (18)0.00206 (12)0.00069 (13)0.01657 (12)
N30.0180 (10)0.0273 (11)0.0260 (11)−0.0011 (8)−0.0002 (9)0.0033 (9)
C60.0187 (11)0.0154 (10)0.0191 (11)−0.0011 (9)−0.0003 (9)−0.0032 (9)
N20.0191 (10)0.0265 (10)0.0241 (11)−0.0024 (8)−0.0010 (8)0.0032 (9)
N10.0214 (10)0.0240 (10)0.0227 (10)−0.0008 (8)0.0001 (9)−0.0013 (8)
N40.0171 (9)0.0191 (9)0.0194 (10)0.0001 (8)−0.0017 (8)0.0001 (8)
C50.0187 (11)0.0152 (10)0.0200 (11)−0.0024 (9)−0.0012 (9)−0.0028 (9)
C70.0159 (11)0.0181 (10)0.0212 (11)−0.0013 (9)−0.0002 (9)−0.0014 (9)
C40.0170 (11)0.0229 (11)0.0246 (12)−0.0011 (9)−0.0006 (10)−0.0021 (10)
C80.0240 (12)0.0200 (11)0.0187 (11)0.0020 (9)−0.0037 (10)−0.0007 (9)
C20.0344 (14)0.0183 (11)0.0208 (12)−0.0028 (10)−0.0075 (11)0.0015 (9)
C10.0251 (12)0.0266 (12)0.0220 (12)−0.0039 (10)0.0024 (10)0.0015 (10)
C90.0424 (15)0.0230 (12)0.0198 (12)0.0072 (11)−0.0026 (11)−0.0027 (10)
C30.0239 (12)0.0204 (11)0.0281 (13)0.0029 (10)−0.0067 (11)−0.0030 (10)
C100.0357 (15)0.0261 (13)0.0264 (13)0.0093 (11)0.0030 (12)0.0028 (10)
Geometric parameters (Å, º) top
Br1—C101.966 (3)C8—C91.516 (3)
N3—N21.315 (3)C8—H8A0.9700
N3—N41.352 (3)C8—H8B0.9700
C6—N21.371 (3)C2—C31.383 (4)
C6—C71.373 (3)C2—C11.384 (4)
C6—C51.471 (3)C2—H20.9300
N1—C11.337 (3)C1—H10.9300
N1—C51.351 (3)C9—C101.501 (4)
N4—C71.344 (3)C9—H9A0.9700
N4—C81.463 (3)C9—H9B0.9700
C5—C41.388 (3)C3—H30.9300
C7—H70.9300C10—H10A0.9700
C4—C31.384 (3)C10—H10B0.9700
C4—H40.9300
N2—N3—N4106.83 (18)H8A—C8—H8B107.9
N2—C6—C7108.4 (2)C3—C2—C1118.2 (2)
N2—C6—C5122.9 (2)C3—C2—H2120.9
C7—C6—C5128.7 (2)C1—C2—H2120.9
N3—N2—C6108.78 (19)N1—C1—C2123.8 (2)
C1—N1—C5117.1 (2)N1—C1—H1118.1
C7—N4—N3111.53 (18)C2—C1—H1118.1
C7—N4—C8127.7 (2)C10—C9—C8112.8 (2)
N3—N4—C8120.73 (19)C10—C9—H9A109.0
N1—C5—C4122.9 (2)C8—C9—H9A109.0
N1—C5—C6115.7 (2)C10—C9—H9B109.0
C4—C5—C6121.4 (2)C8—C9—H9B109.0
N4—C7—C6104.5 (2)H9A—C9—H9B107.8
N4—C7—H7127.8C2—C3—C4119.3 (2)
C6—C7—H7127.8C2—C3—H3120.4
C3—C4—C5118.6 (2)C4—C3—H3120.4
C3—C4—H4120.7C9—C10—Br1111.7 (2)
C5—C4—H4120.7C9—C10—H10A109.3
N4—C8—C9111.80 (19)Br1—C10—H10A109.3
N4—C8—H8A109.3C9—C10—H10B109.3
C9—C8—H8A109.3Br1—C10—H10B109.3
N4—C8—H8B109.3H10A—C10—H10B107.9
C9—C8—H8B109.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N2i0.932.623.449 (4)149
C10—H10B···N1ii0.972.513.450 (4)164
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC10H11BrN4
Mr267.14
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)5.658 (2), 9.688 (4), 10.191 (4)
α, β, γ (°)84.498 (3), 85.663 (2), 83.854 (2)
V (Å3)551.6 (4)
Z2
Radiation typeMo Kα
µ (mm−1)3.70
Crystal size (mm)0.53 × 0.23 × 0.11
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.358, 0.66
No. of measured, independent and
observed [I > 2σ(I)] reflections		8776, 1879, 1759
Rint0.043
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.071, 0.97
No. of reflections1879
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.64, −0.61

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N2i0.932.623.449 (4)149
C10—H10B···N1ii0.972.513.450 (4)164
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z+1.
 

Acknowledgements

We thank the Chemistry Department, University of Otago, for financial assistance.

References

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ISSN: 2056-9890
Volume 65| Part 5| May 2009| Pages o999-o1000
doi:10.1107/S1600536809012148
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