Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page o2838
doi:10.1107/S1600536811040177

6-Bromo­imidazo[1,2-a]pyridin-8-amine

Siham Dahmani,a Youssef Kandri Rodi,a Frederic Capet,b El Mokhtar Essassic and Seik Weng Ngd,e*

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bUnité de Catalyse et de Chimie du Solide, Ecole Nationale Supérieure de Chimie de Lille, Lille, France, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and eChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 29 September 2011; accepted 29 September 2011; online 5 October 2011)

The title compound, C7H6BrN3, crystallizes with three independent mol­ecules in the asymmetric unit. The mol­ecules are approximately planar (r.m.s. deviations for all non-H atoms = 0.016, 0.023 and 0.024 Å). The primary amine groups show pyramidal coordination. In the crystal, adjacent mol­ecules are linked by N—H⋯N hydrogen bonds. For two independent mol­ecules, the amine groups are hydrogen-bond donors via one H atom to one acceptor atom, whereas for the third independent mol­ecule, the amine group is a hydrogen-bond donor to two acceptor atoms.

Related literature

For background information on 8-amino-6-bromo-imidazo[1,2-a]pyridine, see: Dwyer et al. (2007[Dwyer, M. P., Paruch, K., Alvarez, C., Doll, R. J., Keertikar, K., Duca, J., Fischmann, T. O., Hruza, A., Madison, V., Lees, E., Parry, D., Seghezzi, W., Sgambellone, N., Shanahan, F., Wiswell, D. & Guzi, T. J. (2007). Bioorg. Med. Chem. Lett. 17, 6216-6219.]).

[Scheme 1]

Experimental

Crystal data

  • C7H6BrN3

  • Mr = 212.06

  • Monoclinic, P 21 /c

  • a = 15.1378 (5) Å

  • b = 21.2006 (8) Å

  • c = 6.9744 (3) Å

  • β = 92.6106 (7)°

  • V = 2235.97 (15) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 5.44 mm−1

  • T = 100 K

  • 0.13 × 0.04 × 0.02 mm
Data collection

  • Bruker APEX DUO diffractometer

  • Absorption correction: multi-scan SADABS (Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])' Tmin = 0.538, Tmax = 0.899

  • 44729 measured reflections

  • 5538 independent reflections

  • 4675 reflections with I > 2σ(I)

  • Rint = 0.048
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.078

  • S = 1.08

  • 5538 reflections

  • 322 parameters

  • 6 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.15 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H31⋯N5 0.88 (1) 2.16 (1) 3.034 (3) 169 (4)
N6—H61⋯N2 0.88 (1) 2.23 (1) 3.094 (3) 168 (3)
N9—H91⋯N8i 0.87 (1) 2.27 (2) 3.091 (3) 158 (3)
N9—H92⋯N6ii 0.88 (1) 2.27 (1) 3.143 (3) 177 (3)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y, z-1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811040177/bt5659sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040177/bt5659Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040177/bt5659Isup3.cml

checkCIF report


Comment top

8-Amino-6-bromo-imidazo[1,2-a]pyridine (Scheme I) was recently evaluated for its as a cyclin-dependent kinase-2 (CDK2) inhibitor (Dwyer et al., 2007). We have synthesized the compound for use in a similar study. The non-H atoms of the three independent molecules of C7H6BrN3 are planar (Fig. 1). Their primary amino groups show pyramidal coordination, and adjacent molecules are linked by N–H···N hydrogen bonds to form a layer structure. For two independent molecules, their amino groups are each a hydrogen-bond donor to one acceptor atom whereas for the third independent molecule, its amino group is hydrogen-bond bond to two acceptor atoms (Table 1).

Related literature top

For background information on 8-amino-6-bromo-imidazo[1,2-a]pyridine, see: Dwyer et al. (2007).

Experimental top

A mixture of chloroacetaldehyde (0.68 ml, 10.6 mmol), 5-bromo-2,3-diaminopyridine (1 g, 5.32 mmol) and sodium bicarbonate (0.44 g, 5.32 mmol) in ethanol (10 ml) was heated. The reaction was monitored by TLC. On completion of the reaction, the solution was extracted with dichloromethane and the organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent followed by recrystallization from hexane gave yellow crystals of the title compound.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C– 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

The amino H-atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of N–H 0.88±0.01 Å.

The final difference Fourier map had a peak in the vicinity of Br1 and a hole in the vicinity of Br2.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the three independent molecules at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
6-Bromoimidazo[1,2-a]pyridin-8-amine top
Crystal data top
C7H6BrN3F(000) = 1248
Mr = 212.06Dx = 1.890 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9878 reflections
a = 15.1378 (5) Åθ = 2.4–28.2°
b = 21.2006 (8) ŵ = 5.44 mm−1
c = 6.9744 (3) ÅT = 100 K
β = 92.6106 (7)°Prism, yellow
V = 2235.97 (15) Å30.13 × 0.04 × 0.02 mm
Z = 12
Data collection top
Bruker APEX DUO
diffractometer		5538 independent reflections
Radiation source: fine-focus sealed tube4675 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)'		h = −20→20
Tmin = 0.538, Tmax = 0.899k = −28→28
44729 measured reflectionsl = −9→9
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) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0398P)2 + 2.2806P]
where P = (Fo2 + 2Fc2)/3
5538 reflections(Δ/σ)max = 0.001
322 parametersΔρmax = 1.15 e Å−3
6 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C7H6BrN3V = 2235.97 (15) Å3
Mr = 212.06Z = 12
Monoclinic, P21/cMo Kα radiation
a = 15.1378 (5) ŵ = 5.44 mm−1
b = 21.2006 (8) ÅT = 100 K
c = 6.9744 (3) Å0.13 × 0.04 × 0.02 mm
β = 92.6106 (7)°
Data collection top
Bruker APEX DUO
diffractometer		5538 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)'		4675 reflections with I > 2σ(I)
Tmin = 0.538, Tmax = 0.899Rint = 0.048
44729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0316 restraints
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 1.15 e Å−3
5538 reflectionsΔρmin = −0.46 e Å−3
322 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.107067 (18)0.309517 (13)0.81184 (4)0.02396 (8)
Br20.248212 (17)0.345125 (13)0.22269 (4)0.02332 (8)
Br30.930771 (17)0.485358 (12)−0.30860 (4)0.01955 (7)
N10.93022 (14)0.35309 (10)0.3739 (3)0.0147 (4)
N20.78304 (15)0.35253 (10)0.3158 (3)0.0170 (4)
N30.76115 (15)0.29900 (11)0.6916 (3)0.0179 (4)
N40.46555 (13)0.23784 (10)0.3560 (3)0.0131 (4)
N50.61032 (14)0.25193 (10)0.4281 (3)0.0153 (4)
N60.58767 (15)0.38763 (10)0.3737 (3)0.0167 (4)
N70.75458 (14)0.52802 (10)0.0966 (3)0.0144 (4)
N80.60864 (14)0.52091 (10)0.1372 (3)0.0165 (4)
N90.58646 (14)0.46594 (10)−0.2438 (3)0.0164 (4)
C11.00873 (17)0.34402 (11)0.4792 (4)0.0174 (5)
H11.06430.35400.42900.021*
C21.00202 (17)0.32018 (12)0.6573 (4)0.0168 (5)
C30.92127 (17)0.30293 (11)0.7364 (4)0.0167 (5)
H30.92070.28500.86120.020*
C40.84294 (17)0.31237 (11)0.6302 (4)0.0145 (5)
C50.84843 (16)0.33958 (11)0.4443 (4)0.0142 (5)
C60.82481 (18)0.37419 (12)0.1590 (4)0.0196 (5)
H60.79490.38700.04270.023*
C70.91483 (18)0.37524 (13)0.1893 (4)0.0194 (5)
H70.95750.38840.10200.023*
C80.37957 (17)0.25553 (12)0.3112 (4)0.0158 (5)
H80.33330.22540.29610.019*
C90.36455 (17)0.31802 (12)0.2898 (4)0.0162 (5)
C100.43202 (17)0.36433 (12)0.3074 (4)0.0157 (5)
H100.41830.40760.28700.019*
C110.51705 (17)0.34614 (11)0.3540 (3)0.0144 (5)
C120.53420 (16)0.28070 (11)0.3834 (3)0.0134 (5)
C130.58955 (18)0.18878 (12)0.4262 (4)0.0173 (5)
H130.63120.15600.45280.021*
C140.50220 (18)0.17886 (12)0.3818 (4)0.0171 (5)
H140.47260.13940.37080.021*
C150.83221 (16)0.52183 (11)0.0020 (4)0.0154 (5)
H150.88730.53580.05740.018*
C160.82568 (16)0.49497 (11)−0.1733 (4)0.0152 (5)
C170.74557 (16)0.47370 (11)−0.2611 (4)0.0142 (5)
H170.74500.4540−0.38350.017*
C180.66754 (16)0.48172 (11)−0.1679 (4)0.0135 (5)
C190.67320 (16)0.50949 (11)0.0182 (4)0.0131 (5)
C200.65091 (18)0.54752 (13)0.2963 (4)0.0206 (5)
H200.62170.56100.40690.025*
C210.73987 (18)0.55214 (13)0.2758 (4)0.0183 (5)
H210.78270.56860.36620.022*
H310.7175 (18)0.2903 (18)0.608 (4)0.045 (11)*
H320.755 (3)0.2726 (15)0.787 (4)0.047 (12)*
H610.6413 (10)0.3726 (14)0.367 (4)0.021 (8)*
H620.581 (2)0.4227 (9)0.307 (4)0.019 (8)*
H910.5382 (13)0.4706 (14)−0.181 (4)0.018 (8)*
H920.586 (2)0.4427 (14)−0.348 (3)0.033 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01367 (13)0.02313 (14)0.03436 (16)−0.00028 (10)−0.00679 (11)0.00462 (11)
Br20.01282 (13)0.02352 (14)0.03321 (16)0.00291 (10)−0.00335 (10)0.00457 (11)
Br30.01248 (12)0.02091 (13)0.02567 (14)−0.00039 (9)0.00531 (9)−0.00224 (10)
N10.0135 (10)0.0149 (10)0.0158 (10)−0.0029 (8)0.0020 (8)−0.0011 (8)
N20.0168 (10)0.0159 (10)0.0182 (11)−0.0023 (8)−0.0023 (8)0.0018 (8)
N30.0138 (11)0.0231 (12)0.0167 (11)−0.0022 (9)0.0012 (8)0.0053 (9)
N40.0119 (10)0.0138 (10)0.0135 (10)0.0000 (8)−0.0009 (8)0.0002 (8)
N50.0155 (10)0.0162 (10)0.0142 (10)0.0002 (8)−0.0006 (8)0.0010 (8)
N60.0151 (11)0.0132 (10)0.0215 (11)−0.0021 (8)−0.0002 (9)−0.0003 (8)
N70.0110 (10)0.0150 (10)0.0171 (10)−0.0012 (8)−0.0015 (8)−0.0009 (8)
N80.0155 (10)0.0158 (10)0.0183 (11)0.0003 (8)0.0021 (8)−0.0005 (8)
N90.0117 (10)0.0190 (11)0.0184 (11)−0.0017 (8)−0.0014 (8)−0.0056 (9)
C10.0107 (11)0.0159 (12)0.0255 (14)−0.0003 (9)0.0009 (10)−0.0034 (10)
C20.0121 (11)0.0141 (11)0.0240 (13)0.0007 (9)−0.0028 (10)−0.0009 (10)
C30.0178 (13)0.0122 (11)0.0201 (13)−0.0009 (9)−0.0005 (10)0.0007 (9)
C40.0140 (12)0.0105 (10)0.0190 (12)−0.0007 (9)0.0018 (9)−0.0007 (9)
C50.0122 (11)0.0119 (11)0.0187 (12)−0.0014 (9)0.0021 (9)−0.0018 (9)
C60.0210 (13)0.0185 (12)0.0188 (13)−0.0054 (10)−0.0037 (10)0.0033 (10)
C70.0224 (13)0.0198 (12)0.0162 (12)−0.0052 (10)0.0022 (10)0.0023 (10)
C80.0140 (12)0.0176 (12)0.0156 (12)−0.0023 (9)−0.0016 (9)0.0005 (9)
C90.0123 (11)0.0184 (12)0.0177 (12)0.0028 (9)−0.0007 (9)0.0000 (10)
C100.0183 (12)0.0136 (11)0.0153 (12)0.0021 (9)0.0008 (9)−0.0009 (9)
C110.0166 (12)0.0153 (11)0.0113 (11)0.0000 (9)−0.0001 (9)−0.0019 (9)
C120.0129 (11)0.0159 (11)0.0113 (11)−0.0019 (9)−0.0002 (9)−0.0014 (9)
C130.0195 (13)0.0156 (12)0.0169 (12)0.0023 (10)0.0018 (10)0.0028 (9)
C140.0220 (13)0.0119 (11)0.0177 (12)0.0017 (10)0.0030 (10)0.0008 (9)
C150.0104 (11)0.0152 (11)0.0204 (12)−0.0015 (9)−0.0002 (9)0.0014 (10)
C160.0118 (11)0.0125 (11)0.0215 (13)0.0010 (9)0.0023 (9)0.0024 (9)
C170.0141 (12)0.0136 (11)0.0149 (12)0.0002 (9)−0.0001 (9)0.0003 (9)
C180.0133 (11)0.0106 (10)0.0164 (12)0.0001 (9)−0.0005 (9)0.0022 (9)
C190.0113 (11)0.0112 (11)0.0168 (12)0.0001 (9)0.0009 (9)0.0021 (9)
C200.0232 (14)0.0213 (13)0.0174 (13)0.0005 (11)0.0038 (10)−0.0026 (10)
C210.0204 (13)0.0207 (13)0.0138 (12)−0.0024 (10)−0.0012 (10)−0.0024 (10)
Geometric parameters (Å, º) top
Br1—C21.893 (3)C1—C21.350 (4)
Br2—C91.891 (3)C1—H10.9500
Br3—C161.897 (3)C2—C31.412 (4)
N1—C71.380 (3)C3—C41.384 (4)
N1—C11.382 (3)C3—H30.9500
N1—C51.383 (3)C4—C51.425 (3)
N2—C51.333 (3)C6—C71.370 (4)
N2—C61.367 (3)C6—H60.9500
N3—C41.358 (3)C7—H70.9500
N3—H310.883 (10)C8—C91.351 (4)
N3—H320.880 (10)C8—H80.9500
N4—C141.377 (3)C9—C101.418 (4)
N4—C81.377 (3)C10—C111.369 (4)
N4—C121.387 (3)C10—H100.9500
N5—C121.328 (3)C11—C121.425 (3)
N5—C131.375 (3)C13—C141.361 (4)
N6—C111.386 (3)C13—H130.9500
N6—H610.875 (10)C14—H140.9500
N6—H620.881 (10)C15—C161.348 (4)
N7—C211.378 (3)C15—H150.9500
N7—C151.380 (3)C16—C171.408 (3)
N7—C191.382 (3)C17—C181.385 (3)
N8—C191.333 (3)C17—H170.9500
N8—C201.377 (3)C18—C191.424 (3)
N9—C181.356 (3)C20—C211.364 (4)
N9—H910.874 (10)C20—H200.9500
N9—H920.876 (10)C21—H210.9500
C7—N1—C1130.4 (2)C9—C8—N4116.4 (2)
C7—N1—C5106.6 (2)C9—C8—H8121.8
C1—N1—C5123.0 (2)N4—C8—H8121.8
C5—N2—C6104.5 (2)C8—C9—C10123.5 (2)
C4—N3—H31120 (3)C8—C9—Br2118.4 (2)
C4—N3—H32121 (3)C10—C9—Br2118.03 (18)
H31—N3—H32105 (4)C11—C10—C9119.4 (2)
C14—N4—C8130.4 (2)C11—C10—H10120.3
C14—N4—C12106.4 (2)C9—C10—H10120.3
C8—N4—C12123.2 (2)C10—C11—N6123.9 (2)
C12—N5—C13104.4 (2)C10—C11—C12118.2 (2)
C11—N6—H61118 (2)N6—C11—C12118.0 (2)
C11—N6—H62114 (2)N5—C12—N4111.6 (2)
H61—N6—H62112 (3)N5—C12—C11129.2 (2)
C21—N7—C15130.2 (2)N4—C12—C11119.2 (2)
C21—N7—C19106.6 (2)C14—C13—N5111.8 (2)
C15—N7—C19123.2 (2)C14—C13—H13124.1
C19—N8—C20104.4 (2)N5—C13—H13124.1
C18—N9—H91123 (2)C13—C14—N4105.7 (2)
C18—N9—H92116 (2)C13—C14—H14127.1
H91—N9—H92120 (3)N4—C14—H14127.1
C2—C1—N1116.3 (2)C16—C15—N7116.4 (2)
C2—C1—H1121.9C16—C15—H15121.8
N1—C1—H1121.9N7—C15—H15121.8
C1—C2—C3124.0 (2)C15—C16—C17123.8 (2)
C1—C2—Br1118.2 (2)C15—C16—Br3117.90 (19)
C3—C2—Br1117.8 (2)C17—C16—Br3118.32 (19)
C4—C3—C2119.3 (2)C18—C17—C16119.5 (2)
C4—C3—H3120.3C18—C17—H17120.2
C2—C3—H3120.3C16—C17—H17120.2
N3—C4—C3124.9 (2)N9—C18—C17124.2 (2)
N3—C4—C5117.6 (2)N9—C18—C19118.3 (2)
C3—C4—C5117.5 (2)C17—C18—C19117.5 (2)
N2—C5—N1111.6 (2)N8—C19—N7111.6 (2)
N2—C5—C4128.5 (2)N8—C19—C18128.8 (2)
N1—C5—C4119.8 (2)N7—C19—C18119.6 (2)
N2—C6—C7112.0 (2)C21—C20—N8111.7 (2)
N2—C6—H6124.0C21—C20—H20124.2
C7—C6—H6124.0N8—C20—H20124.2
C6—C7—N1105.3 (2)C20—C21—N7105.6 (2)
C6—C7—H7127.4C20—C21—H21127.2
N1—C7—H7127.4N7—C21—H21127.2
C7—N1—C1—C2−178.7 (2)C8—N4—C12—N5179.0 (2)
C5—N1—C1—C20.7 (4)C14—N4—C12—C11176.1 (2)
N1—C1—C2—C31.9 (4)C8—N4—C12—C11−3.6 (4)
N1—C1—C2—Br1−177.80 (17)C10—C11—C12—N5179.6 (2)
C1—C2—C3—C4−2.1 (4)N6—C11—C12—N5−0.2 (4)
Br1—C2—C3—C4177.53 (18)C10—C11—C12—N42.7 (3)
C2—C3—C4—N3−178.6 (2)N6—C11—C12—N4−177.1 (2)
C2—C3—C4—C5−0.2 (4)C12—N5—C13—C14−0.2 (3)
C6—N2—C5—N10.7 (3)N5—C13—C14—N4−0.6 (3)
C6—N2—C5—C4−176.3 (2)C8—N4—C14—C13−179.2 (2)
C7—N1—C5—N2−0.6 (3)C12—N4—C14—C131.1 (3)
C1—N1—C5—N2179.8 (2)C21—N7—C15—C16178.8 (2)
C7—N1—C5—C4176.6 (2)C19—N7—C15—C16−1.5 (4)
C1—N1—C5—C4−3.0 (4)N7—C15—C16—C170.1 (4)
N3—C4—C5—N2−2.2 (4)N7—C15—C16—Br3−179.89 (17)
C3—C4—C5—N2179.3 (2)C15—C16—C17—C181.8 (4)
N3—C4—C5—N1−178.9 (2)Br3—C16—C17—C18−178.21 (18)
C3—C4—C5—N12.6 (3)C16—C17—C18—N9176.5 (2)
C5—N2—C6—C7−0.5 (3)C16—C17—C18—C19−2.3 (3)
N2—C6—C7—N10.1 (3)C20—N8—C19—N7−0.1 (3)
C1—N1—C7—C6179.8 (2)C20—N8—C19—C18179.5 (2)
C5—N1—C7—C60.3 (3)C21—N7—C19—N80.3 (3)
C14—N4—C8—C9−178.1 (2)C15—N7—C19—N8−179.5 (2)
C12—N4—C8—C91.6 (4)C21—N7—C19—C18−179.3 (2)
N4—C8—C9—C101.3 (4)C15—N7—C19—C180.9 (4)
N4—C8—C9—Br2178.65 (17)N9—C18—C19—N82.6 (4)
C8—C9—C10—C11−2.0 (4)C17—C18—C19—N8−178.5 (2)
Br2—C9—C10—C11−179.38 (19)N9—C18—C19—N7−177.8 (2)
C9—C10—C11—N6179.7 (2)C17—C18—C19—N71.0 (3)
C9—C10—C11—C12−0.1 (4)C19—N8—C20—C21−0.2 (3)
C13—N5—C12—N40.9 (3)N8—C20—C21—N70.4 (3)
C13—N5—C12—C11−176.2 (2)C15—N7—C21—C20179.3 (2)
C14—N4—C12—N5−1.3 (3)C19—N7—C21—C20−0.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N50.88 (1)2.16 (1)3.034 (3)169 (4)
N6—H61···N20.88 (1)2.23 (1)3.094 (3)168 (3)
N9—H91···N8i0.87 (1)2.27 (2)3.091 (3)158 (3)
N9—H92···N6ii0.88 (1)2.27 (1)3.143 (3)177 (3)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formulaC7H6BrN3
Mr212.06
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)15.1378 (5), 21.2006 (8), 6.9744 (3)
β (°) 92.6106 (7)
V (Å3)2235.97 (15)
Z12
Radiation typeMo Kα
µ (mm−1)5.44
Crystal size (mm)0.13 × 0.04 × 0.02
Data collection
DiffractometerBruker APEX DUO
diffractometer
Absorption correctionMulti-scan
SADABS (Sheldrick, 1996)'
Tmin, Tmax0.538, 0.899
No. of measured, independent and
observed [I > 2σ(I)] reflections		44729, 5538, 4675
Rint0.048
(sin θ/λ)max (Å−1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.078, 1.08
No. of reflections5538
No. of parameters322
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.15, −0.46

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N50.88 (1)2.16 (1)3.034 (3)169 (4)
N6—H61···N20.88 (1)2.23 (1)3.094 (3)168 (3)
N9—H91···N8i0.87 (1)2.27 (2)3.091 (3)158 (3)
N9—H92···N6ii0.88 (1)2.27 (1)3.143 (3)177 (3)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z−1.
 

Acknowledgements

We thank Université MohammedV-Agdal, Université Sidi Mohammed Ben Abdallah and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDwyer, M. P., Paruch, K., Alvarez, C., Doll, R. J., Keertikar, K., Duca, J., Fischmann, T. O., Hruza, A., Madison, V., Lees, E., Parry, D., Seghezzi, W., Sgambellone, N., Shanahan, F., Wiswell, D. & Guzi, T. J. (2007). Bioorg. Med. Chem. Lett. 17, 6216–6219.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page o2838
doi:10.1107/S1600536811040177
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS