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ISSN: 2056-9890

N-(5-Bromo­pyridin-2-yl)acetamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel
*Correspondence e-mail: hkfun@usm.my

(Received 25 June 2011; accepted 9 July 2011; online 16 July 2011)

The asymmetric unit of the title compound, C7H7BrN2O, contains two mol­ecules, in one of which the methyl H atoms are disorderd over two orientations in a 0.57 (3):0.43 (3) ratio. The dihedral angles between the pyridine rings and the acetamide groups are 7.27 (11) and 8.46 (11)°. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds generating bifurcated R21(5) ring motifs, which in turn lead to [110] chains.

Related literature

For background to the acetyl­ation of amines, see: Greene & Wuts (1999[Greene, T. W. & Wuts, P. G. M. (1999). Protective Groups in Organic Chemistry, 3rd ed., ch. 7, pp. 552-555. New York: Wiley and Sons.]); Moore et al. (1940[Moore, M. L., Miller, C. S. & Miller, E. (1940). J. Am. Chem. Soc. 62, 2097-2099.]); Suyama & Gerwick (2006[Suyama, T. L. & Gerwick, W. H. (2006). Org. Lett. 8, 4541-4543.]). For a related structure, see: Loureiro et al. (2008[Loureiro, R. M. S., Johnstone, R. A. W. & Labat, G. (2008). Acta Cryst. C64, o306-o308.]). For further synthetic information, see: Augustine et al. (2011[Augustine, J. K., Kumar, R., Bombrun, A. & Mandal, A. B. (2011). Tetrahedron Lett. 52, 1074-1077.]); Sollogoub et al. (2002[Sollogoub, M., Fox, K. R., Powers, V. E. C. & Brown, T. (2002). Tetrahedron Lett. 43, 3121-3123.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7BrN2O

  • Mr = 215.06

  • Triclinic, [P \overline 1]

  • a = 4.0014 (3) Å

  • b = 8.7232 (6) Å

  • c = 23.0626 (18) Å

  • α = 82.127 (1)°

  • β = 86.897 (1)°

  • γ = 85.932 (1)°

  • V = 794.60 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.11 mm−1

  • T = 296 K

  • 0.77 × 0.15 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.111, Tmax = 0.665

  • 13194 measured reflections

  • 5134 independent reflections

  • 3193 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.00

  • 5134 reflections

  • 201 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H1NA⋯O1Bi 0.85 2.16 3.001 (2) 169
N2B—H1NB⋯O1Aii 0.83 2.20 2.985 (2) 159
C7A—H7AA⋯O1Bi 1.10 2.54 3.476 (3) 142
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The acetylation of amines is an important method for protection (Greene & Wuts, 1999) of this basic functionality that is an important part of many natural products and medicinally important compounds such as sulphanilamide (Moore et al., 1940). In addition, certain natural products and medicinal compounds contain the acetamide functionality as part of the native compound or drug. Examples include epiquinamide, a compound isolated from a poison frog (Suyama et al., 2006) and Tylenol a common analgesic compound. Prompted by these, we synthesized the title compound, (I), and determined its crystal structure.

The asymmetric unit of (I) consists of two independent molecules of N-(5-bromopyridin-2-yl)acetamide (A & B) as shown in Fig. 1. In molecule A, the methyl hydrogen atoms are disordered over two sets of sites, with occupancy ratio of 0.57 (3):0.43 (3). The pyridine (N1A/C1A–C5A)/(N1B/C1B–C5B) rings are essentially planar, with maximum deviations of 0.006 (2) Å for atom C4A and 0.004 (2) Å for atom N1B, respectively. The dihedral angle between the pyridine (N1A/C1A–C5A)/(N1B/C1B–C5B) rings and acetamide (N2A/O1A/C5A–C7A)/ (N2B/O1B/C5B–C7B) groups are 7.27 (11)° and 8.46 (11)° respectively. The bond lengths and angles are normal and comparable to those in a related structure (Loureiro et al., 2008).

In the crystal (Fig. 2), the molecules are linked by intermolecular N2A—H1NA···O1B, N2B—H1NB···O1A and C7A—H7AA···O1B hydrogen bonds (Table 1) generating a bifurcated R12(5) ring motif, resulting in supramolecular [1 1 0] chains.

Related literature top

For background to the acetylation of amines, see: Greene & Wuts (1999); Moore et al. (1940); Suyama et al. (2006). For a related structure, see: Loureiro et al. (2008). For further synthetic information, see: Augustine et al. (2011); Sollogoub et al. (2002).

Experimental top

(1E)-1-(5-Bromopyridin-2-yl)-N-hydroxyethanimine (2 g, 0.0093 mol) was taken in N,N dimethyl formamide (20 ml) at 25–26°C under a nitrogen atmosphere. Propylphosphonic anhydride (0.6 g, 0.00093 mol, 50% solution in ethylacetate) was added at the same temperature (Augustine et al., 2011). The reaction mixture was heated to 100°C for 5 hrs. The reaction mixture was cooled to 25–26°C and quenched onto ice-cold water. The precipitated white solid was filtered and dried under vacuum to get the desired product as a white solid which was then recrystallized from ethanol (Sollogoub et al., 2002) to yield colourless needles of (I). Yield 1.89 g (94.5%) Mp. 447–449 K.

Refinement top

All the H atoms were positioned geometrically [C–H = 0.9300 to 1.1046 Å, N–H = 0.8514 to 0.9600 Å] and were refined using a riding model, with Uiso(H) =1.2 or 1.5Uiso(C). One set of the methyl hydrogen atoms are disordered over two sets of sites, with occupancy ratio of 0.57 (3):0.43 (3).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound, showing chains along the [110] direction. Only the major component is shown.
N-(5-Bromopyridin-2-yl)acetamide top
Crystal data top
C7H7BrN2OZ = 4
Mr = 215.06F(000) = 424
Triclinic, P1Dx = 1.798 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.0014 (3) ÅCell parameters from 3316 reflections
b = 8.7232 (6) Åθ = 2.8–30.5°
c = 23.0626 (18) ŵ = 5.11 mm1
α = 82.127 (1)°T = 296 K
β = 86.897 (1)°Needle, colourless
γ = 85.932 (1)°0.77 × 0.15 × 0.09 mm
V = 794.60 (10) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
5134 independent reflections
Radiation source: fine-focus sealed tube3193 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 31.2°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 55
Tmin = 0.111, Tmax = 0.665k = 1212
13194 measured reflectionsl = 3333
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.036P)2 + 0.0264P]
where P = (Fo2 + 2Fc2)/3
5134 reflections(Δ/σ)max = 0.006
201 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C7H7BrN2Oγ = 85.932 (1)°
Mr = 215.06V = 794.60 (10) Å3
Triclinic, P1Z = 4
a = 4.0014 (3) ÅMo Kα radiation
b = 8.7232 (6) ŵ = 5.11 mm1
c = 23.0626 (18) ÅT = 296 K
α = 82.127 (1)°0.77 × 0.15 × 0.09 mm
β = 86.897 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
5134 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3193 reflections with I > 2σ(I)
Tmin = 0.111, Tmax = 0.665Rint = 0.025
13194 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.081H-atom parameters constrained
S = 1.00Δρmax = 0.35 e Å3
5134 reflectionsΔρmin = 0.25 e Å3
201 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*/UeqOcc. (<1)
Br1A0.84865 (6)0.73249 (2)0.465121 (9)0.05565 (9)
O1A0.4679 (4)0.97838 (16)0.73640 (6)0.0613 (5)
N1A0.4235 (5)0.63040 (18)0.63081 (7)0.0492 (4)
N2A0.3137 (4)0.75247 (17)0.71180 (6)0.0433 (4)
H1NA0.22210.66740.72260.052*
C1A0.5431 (6)0.6264 (2)0.57599 (9)0.0509 (5)
H1AA0.53030.53560.55950.061*
C2A0.6845 (5)0.7499 (2)0.54257 (8)0.0433 (4)
C3A0.7046 (6)0.8840 (2)0.56632 (9)0.0517 (5)
H3AA0.79670.96950.54440.062*
C4A0.5868 (6)0.8907 (2)0.62322 (9)0.0515 (5)
H4AA0.60180.98010.64050.062*
C5A0.4449 (5)0.7612 (2)0.65427 (8)0.0397 (4)
C6A0.3318 (5)0.8566 (2)0.74991 (8)0.0427 (4)
C7A0.1744 (6)0.8125 (3)0.80974 (9)0.0568 (6)
H7AA0.08490.69420.81670.085*0.57 (3)
H7AB0.01540.90510.81880.085*0.57 (3)
H7AC0.32100.81170.84270.085*0.57 (3)
H7AD0.20030.89290.83340.085*0.43 (3)
H7AE0.28260.71720.82750.085*0.43 (3)
H7AF0.05980.79920.80670.085*0.43 (3)
Br1B0.14559 (6)0.24850 (3)1.034407 (9)0.05895 (9)
O1B0.9318 (4)0.47747 (16)0.76218 (6)0.0586 (4)
N1B0.4457 (5)0.13387 (19)0.87208 (7)0.0566 (5)
N2B0.6803 (4)0.25146 (17)0.78696 (6)0.0464 (4)
H1NB0.65980.16340.77850.056*
C1B0.3245 (7)0.1341 (2)0.92681 (10)0.0594 (6)
H1BA0.23650.04410.94610.071*
C2B0.3226 (5)0.2599 (2)0.95615 (8)0.0443 (5)
C3B0.4515 (6)0.3934 (2)0.92795 (9)0.0513 (5)
H3BA0.45490.48040.94710.062*
C4B0.5752 (6)0.3965 (2)0.87127 (9)0.0506 (5)
H4BA0.66210.48570.85110.061*
C5B0.5681 (5)0.2635 (2)0.84446 (8)0.0403 (4)
C6B0.8508 (5)0.3553 (2)0.74883 (8)0.0430 (4)
C7B0.9337 (6)0.3063 (2)0.68947 (8)0.0535 (5)
H7BA1.07110.38040.66670.080*
H7BB0.73020.30090.66980.080*
H7BC1.05280.20620.69390.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.06525 (17)0.05384 (14)0.05063 (13)0.01839 (11)0.01455 (10)0.01617 (9)
O1A0.0935 (13)0.0446 (8)0.0504 (8)0.0284 (8)0.0052 (8)0.0140 (6)
N1A0.0661 (12)0.0349 (8)0.0487 (9)0.0178 (8)0.0068 (8)0.0091 (7)
N2A0.0546 (11)0.0322 (8)0.0439 (9)0.0118 (7)0.0042 (8)0.0063 (6)
C1A0.0665 (15)0.0360 (9)0.0532 (11)0.0158 (10)0.0074 (10)0.0145 (8)
C2A0.0470 (12)0.0400 (10)0.0445 (10)0.0104 (9)0.0036 (9)0.0099 (8)
C3A0.0658 (15)0.0391 (10)0.0520 (11)0.0220 (10)0.0111 (10)0.0080 (8)
C4A0.0726 (16)0.0332 (9)0.0519 (11)0.0193 (10)0.0085 (10)0.0128 (8)
C5A0.0407 (11)0.0332 (9)0.0463 (10)0.0064 (8)0.0009 (8)0.0074 (7)
C6A0.0502 (12)0.0378 (9)0.0413 (9)0.0058 (9)0.0029 (8)0.0076 (7)
C7A0.0728 (16)0.0567 (12)0.0427 (11)0.0150 (12)0.0061 (10)0.0107 (9)
Br1B0.06627 (17)0.06192 (15)0.05093 (13)0.02114 (12)0.01604 (11)0.01425 (10)
O1B0.0785 (11)0.0464 (8)0.0529 (8)0.0275 (8)0.0091 (7)0.0069 (6)
N1B0.0841 (14)0.0414 (9)0.0473 (9)0.0249 (9)0.0121 (9)0.0120 (7)
N2B0.0627 (12)0.0340 (8)0.0443 (9)0.0145 (8)0.0051 (8)0.0087 (6)
C1B0.0811 (17)0.0427 (11)0.0564 (12)0.0266 (11)0.0164 (12)0.0103 (9)
C2B0.0432 (12)0.0468 (10)0.0444 (10)0.0127 (9)0.0056 (8)0.0088 (8)
C3B0.0667 (15)0.0384 (10)0.0517 (11)0.0149 (10)0.0071 (10)0.0141 (8)
C4B0.0701 (15)0.0328 (9)0.0500 (11)0.0175 (9)0.0070 (10)0.0063 (8)
C5B0.0452 (12)0.0333 (9)0.0438 (10)0.0093 (8)0.0007 (8)0.0073 (7)
C6B0.0466 (12)0.0375 (9)0.0448 (10)0.0068 (9)0.0016 (8)0.0031 (8)
C7B0.0610 (15)0.0532 (12)0.0471 (11)0.0127 (11)0.0065 (10)0.0081 (9)
Geometric parameters (Å, º) top
Br1A—C2A1.8914 (18)C7A—H7AF0.9600
O1A—C6A1.223 (2)Br1B—C2B1.8951 (18)
N1A—C1A1.331 (3)O1B—C6B1.218 (2)
N1A—C5A1.338 (2)N1B—C1B1.328 (3)
N2A—C6A1.356 (2)N1B—C5B1.331 (2)
N2A—C5A1.395 (2)N2B—C6B1.365 (2)
N2A—H1NA0.8514N2B—C5B1.392 (2)
C1A—C2A1.374 (3)N2B—H1NB0.8288
C1A—H1AA0.9300C1B—C2B1.365 (3)
C2A—C3A1.367 (3)C1B—H1BA0.9300
C3A—C4A1.378 (3)C2B—C3B1.373 (3)
C3A—H3AA0.9300C3B—C4B1.370 (3)
C4A—C5A1.391 (3)C3B—H3BA0.9300
C4A—H4AA0.9300C4B—C5B1.390 (3)
C6A—C7A1.498 (3)C4B—H4BA0.9300
C7A—H7AA1.1046C6B—C7B1.503 (3)
C7A—H7AB1.1020C7B—H7BA0.9600
C7A—H7AC0.9834C7B—H7BB0.9600
C7A—H7AD0.9601C7B—H7BC0.9600
C7A—H7AE0.9601
C1A—N1A—C5A117.99 (17)H7AD—C7A—H7AE109.5
C6A—N2A—C5A127.87 (16)C6A—C7A—H7AF109.7
C6A—N2A—H1NA120.4H7AA—C7A—H7AF60.9
C5A—N2A—H1NA111.7H7AB—C7A—H7AF59.5
N1A—C1A—C2A123.21 (18)H7AC—C7A—H7AF134.3
N1A—C1A—H1AA118.4H7AD—C7A—H7AF109.5
C2A—C1A—H1AA118.4H7AE—C7A—H7AF109.5
C3A—C2A—C1A118.88 (18)C1B—N1B—C5B118.10 (17)
C3A—C2A—Br1A121.10 (14)C6B—N2B—C5B128.33 (16)
C1A—C2A—Br1A120.01 (14)C6B—N2B—H1NB119.6
C2A—C3A—C4A119.17 (18)C5B—N2B—H1NB111.5
C2A—C3A—H3AA120.4N1B—C1B—C2B123.26 (19)
C4A—C3A—H3AA120.4N1B—C1B—H1BA118.4
C3A—C4A—C5A118.69 (17)C2B—C1B—H1BA118.4
C3A—C4A—H4AA120.7C1B—C2B—C3B118.78 (18)
C5A—C4A—H4AA120.7C1B—C2B—Br1B120.11 (15)
N1A—C5A—C4A122.06 (18)C3B—C2B—Br1B121.12 (15)
N1A—C5A—N2A113.20 (16)C4B—C3B—C2B119.06 (18)
C4A—C5A—N2A124.74 (16)C4B—C3B—H3BA120.5
O1A—C6A—N2A122.27 (17)C2B—C3B—H3BA120.5
O1A—C6A—C7A122.17 (17)C3B—C4B—C5B118.65 (18)
N2A—C6A—C7A115.57 (17)C3B—C4B—H4BA120.7
C6A—C7A—H7AA113.6C5B—C4B—H4BA120.7
C6A—C7A—H7AB108.3N1B—C5B—C4B122.15 (18)
H7AA—C7A—H7AB115.1N1B—C5B—N2B113.26 (16)
C6A—C7A—H7AC115.8C4B—C5B—N2B124.59 (17)
H7AA—C7A—H7AC102.8O1B—C6B—N2B122.50 (17)
H7AB—C7A—H7AC100.6O1B—C6B—C7B122.78 (17)
C6A—C7A—H7AD109.4N2B—C6B—C7B114.71 (16)
H7AA—C7A—H7AD136.6C6B—C7B—H7BA109.5
H7AB—C7A—H7AD53.5C6B—C7B—H7BB109.5
H7AC—C7A—H7AD51.1H7BA—C7B—H7BB109.5
C6A—C7A—H7AE109.4C6B—C7B—H7BC109.5
H7AA—C7A—H7AE50.3H7BA—C7B—H7BC109.5
H7AB—C7A—H7AE142.2H7BB—C7B—H7BC109.5
H7AC—C7A—H7AE59.4
C5A—N1A—C1A—C2A0.4 (4)C5B—N1B—C1B—C2B0.7 (4)
N1A—C1A—C2A—C3A0.0 (4)N1B—C1B—C2B—C3B0.1 (4)
N1A—C1A—C2A—Br1A179.81 (18)N1B—C1B—C2B—Br1B179.7 (2)
C1A—C2A—C3A—C4A0.8 (4)C1B—C2B—C3B—C4B0.5 (4)
Br1A—C2A—C3A—C4A178.97 (18)Br1B—C2B—C3B—C4B179.66 (18)
C2A—C3A—C4A—C5A1.2 (4)C2B—C3B—C4B—C5B0.5 (4)
C1A—N1A—C5A—C4A0.0 (3)C1B—N1B—C5B—C4B0.7 (4)
C1A—N1A—C5A—N2A179.75 (19)C1B—N1B—C5B—N2B178.4 (2)
C3A—C4A—C5A—N1A0.8 (3)C3B—C4B—C5B—N1B0.1 (4)
C3A—C4A—C5A—N2A179.5 (2)C3B—C4B—C5B—N2B179.0 (2)
C6A—N2A—C5A—N1A171.58 (19)C6B—N2B—C5B—N1B172.3 (2)
C6A—N2A—C5A—C4A8.2 (3)C6B—N2B—C5B—C4B8.6 (4)
C5A—N2A—C6A—O1A1.7 (3)C5B—N2B—C6B—O1B0.9 (3)
C5A—N2A—C6A—C7A178.2 (2)C5B—N2B—C6B—C7B179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O1Bi0.852.163.001 (2)169
N2B—H1NB···O1Aii0.832.202.985 (2)159
C7A—H7AA···O1Bi1.102.543.476 (3)142
Symmetry codes: (i) x1, y, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC7H7BrN2O
Mr215.06
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)4.0014 (3), 8.7232 (6), 23.0626 (18)
α, β, γ (°)82.127 (1), 86.897 (1), 85.932 (1)
V3)794.60 (10)
Z4
Radiation typeMo Kα
µ (mm1)5.11
Crystal size (mm)0.77 × 0.15 × 0.09
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.111, 0.665
No. of measured, independent and
observed [I > 2σ(I)] reflections
13194, 5134, 3193
Rint0.025
(sin θ/λ)max1)0.729
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.081, 1.00
No. of reflections5134
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O1Bi0.852.163.001 (2)169
N2B—H1NB···O1Aii0.832.202.985 (2)159
C7A—H7AA···O1Bi1.102.543.476 (3)142
Symmetry codes: (i) x1, y, z; (ii) x, y1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship. AMI thanks Professor Sandeep Sanchethi, Director, National Institute of Technology–Karnataka, India, for his encouragement, and also the Defence Research and Development Organization, Government of India, for financial support.

References

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First citationSuyama, T. L. & Gerwick, W. H. (2006). Org. Lett. 8, 4541-4543.  Web of Science CrossRef PubMed CAS

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