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ISSN: 2056-9890

N-(Quinoxalin-2-yl)-4-toluidine

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 4 December 2008; accepted 5 December 2008; online 10 December 2008)

The aromatic and the aromatic fused-rings in the title compound, C15H13N3, open the angle at the planar N atom to 130.07 (13) and 129.98 (13)° in the two independent mol­ecules in the asymmetric unit. The amino N atom of one mol­ecule forms a hydrogen bond to the 4-N atom of an adjacent quinoxalinyl ring, generating a supra­molecular chain.

Related literature

For the structure of N-(2-pyrid­yl)-4-toluidine, see: Fairuz et al. (2008[Fairuz, Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2441.]); for that of N-(pyrazin-2-yl)-4-toluidine, see: Wan Saffiee et al. (2008[Wan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2440.]). The title compound is isostructural with N-(quinoxalin-2-yl)-4-chloro­aniline; see: Idris et al. (2008[Idris, A., Wan Saffiee, W. A. M., Abdullah, Z., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o2443.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13N3

  • Mr = 235.28

  • Orthorhombic, P b c a

  • a = 12.2081 (9) Å

  • b = 11.3720 (9) Å

  • c = 35.097 (3) Å

  • V = 4872.5 (6) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 (2) K

  • 0.40 × 0.15 × 0.05 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 26747 measured reflections

  • 5592 independent reflections

  • 4089 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.112

  • S = 1.03

  • 5592 reflections

  • 335 parameters

  • 2 restraints

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

  • Δρmax = 0.25 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
N1—H1⋯N5 0.89 (1) 2.26 (1) 3.114 (2) 163 (2)
N4—H4⋯N2i 0.87 (1) 2.19 (1) 3.017 (2) 157 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the structure of N-(2-pyridyl)-4-toluidine, see: Fairuz et al. (2008); for that of N-(pyrazin-2-yl)-4-toluidine, see: Wan Saffiee et al. (2008). The title compound is isostructural with N-(quinoxalin-2-yl)-4-chloroaniline; see: Idris et al. (2008).

Experimental top

2-Chloroquinoxaline (1.64 g, 10 mmol) and 4-toluidine (1.07 g, 10 mmol) were mixed with ethanol (2 ml) and the mixture was heated at 423–433 K for 3 h. The product was dissolved in water and the solution extracted with ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped crystals along with some unidentified brown material.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5eqU(C). The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å; their temperature factors were freely refined.

Computing details top

Data collection: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) for the two independent molecules of C15H13N3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
N-(Quinoxalin-2-yl)-4-toluidine top
Crystal data top
C15H13N3F(000) = 1984
Mr = 235.28Dx = 1.283 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3585 reflections
a = 12.2081 (9) Åθ = 2.5–27.6°
b = 11.3720 (9) ŵ = 0.08 mm1
c = 35.097 (3) ÅT = 100 K
V = 4872.5 (6) Å3Block, yellow
Z = 160.40 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer
4089 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Graphite monochromatorθmax = 27.5°, θmin = 1.2°
ω scansh = 1515
26747 measured reflectionsk = 149
5592 independent reflectionsl = 4545
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0453P)2 + 2.027P]
where P = (Fo2 + 2Fc2)/3
5592 reflections(Δ/σ)max = 0.001
335 parametersΔρmax = 0.25 e Å3
2 restraintsΔρmin = 0.25 e Å3
Crystal data top
C15H13N3V = 4872.5 (6) Å3
Mr = 235.28Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 12.2081 (9) ŵ = 0.08 mm1
b = 11.3720 (9) ÅT = 100 K
c = 35.097 (3) Å0.40 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer
4089 reflections with I > 2σ(I)
26747 measured reflectionsRint = 0.051
5592 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0412 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.25 e Å3
5592 reflectionsΔρmin = 0.25 e Å3
335 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.48774 (11)0.63997 (12)0.55869 (4)0.0200 (3)
N20.54428 (10)0.38803 (11)0.61730 (3)0.0183 (3)
N30.41112 (10)0.45078 (11)0.55410 (3)0.0169 (3)
N40.78134 (10)0.95678 (12)0.67401 (4)0.0194 (3)
N50.57078 (11)0.78948 (12)0.62719 (4)0.0207 (3)
N60.59133 (10)0.96931 (11)0.68290 (3)0.0183 (3)
C10.47718 (12)0.52591 (13)0.57059 (4)0.0166 (3)
C20.54419 (12)0.49311 (14)0.60265 (4)0.0188 (3)
H20.59060.55100.61360.023*
C30.47637 (12)0.30629 (13)0.60042 (4)0.0164 (3)
C40.47172 (12)0.19136 (14)0.61498 (4)0.0193 (3)
H4A0.51620.16970.63610.023*
C50.40277 (13)0.11048 (14)0.59870 (4)0.0217 (3)
H50.39930.03280.60860.026*
C60.33726 (13)0.14250 (14)0.56743 (4)0.0220 (3)
H60.28970.08590.55630.026*
C70.34082 (12)0.25413 (14)0.55266 (4)0.0204 (3)
H70.29640.27410.53140.024*
C80.41034 (12)0.33894 (13)0.56900 (4)0.0166 (3)
C90.43642 (12)0.69945 (14)0.52834 (4)0.0178 (3)
C100.38087 (12)0.64377 (14)0.49874 (4)0.0182 (3)
H100.37410.56060.49830.022*
C110.33549 (13)0.71156 (14)0.46985 (4)0.0205 (3)
H110.29810.67310.44970.025*
C120.34273 (12)0.83326 (14)0.46935 (4)0.0194 (3)
C130.39785 (13)0.88706 (14)0.49930 (5)0.0222 (3)
H130.40360.97040.49990.027*
C140.44450 (13)0.82189 (14)0.52828 (5)0.0222 (3)
H140.48230.86070.54830.027*
C150.29166 (14)0.90520 (15)0.43798 (5)0.0269 (4)
H15A0.34070.97020.43120.040*
H15B0.22130.93690.44670.040*
H15C0.27970.85530.41560.040*
C160.67680 (13)0.92171 (13)0.66615 (4)0.0174 (3)
C170.66505 (13)0.83080 (14)0.63794 (4)0.0198 (3)
H170.72940.79940.62660.024*
C180.47952 (13)0.83502 (14)0.64525 (4)0.0190 (3)
C190.37461 (14)0.79237 (15)0.63617 (5)0.0247 (4)
H190.36660.73180.61770.030*
C200.28394 (14)0.83771 (16)0.65375 (5)0.0274 (4)
H200.21330.80840.64750.033*
C210.29513 (13)0.92756 (16)0.68096 (5)0.0265 (4)
H210.23170.95910.69290.032*
C220.39656 (13)0.97021 (15)0.69051 (4)0.0226 (4)
H220.40321.03060.70910.027*
C230.49085 (12)0.92445 (14)0.67284 (4)0.0178 (3)
C240.81936 (13)1.04794 (13)0.69774 (4)0.0177 (3)
C250.75245 (13)1.11936 (15)0.72024 (4)0.0233 (4)
H250.67531.10830.72030.028*
C260.79967 (13)1.20656 (15)0.74242 (5)0.0242 (4)
H260.75351.25500.75750.029*
C270.91210 (13)1.22577 (14)0.74339 (4)0.0202 (3)
C280.97681 (12)1.15459 (14)0.72058 (4)0.0191 (3)
H281.05391.16620.72040.023*
C290.93207 (12)1.06744 (14)0.69819 (4)0.0180 (3)
H290.97861.02000.68290.022*
C300.96087 (14)1.31961 (15)0.76827 (5)0.0263 (4)
H30A1.04071.31930.76540.040*
H30B0.94171.30420.79490.040*
H30C0.93201.39650.76070.040*
H10.5235 (14)0.6854 (15)0.5750 (5)0.038 (6)*
H40.8327 (12)0.9193 (14)0.6617 (5)0.027 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0240 (7)0.0156 (7)0.0204 (6)0.0025 (6)0.0051 (5)0.0004 (5)
N20.0179 (6)0.0195 (7)0.0176 (6)0.0004 (5)0.0005 (5)0.0004 (5)
N30.0164 (6)0.0162 (7)0.0181 (6)0.0003 (5)0.0000 (5)0.0003 (5)
N40.0166 (6)0.0193 (7)0.0223 (7)0.0015 (6)0.0030 (5)0.0053 (5)
N50.0234 (7)0.0180 (7)0.0208 (6)0.0017 (6)0.0018 (5)0.0008 (5)
N60.0181 (6)0.0189 (7)0.0179 (6)0.0022 (5)0.0003 (5)0.0008 (5)
C10.0162 (7)0.0163 (8)0.0174 (7)0.0000 (6)0.0021 (6)0.0006 (6)
C20.0190 (7)0.0195 (8)0.0180 (7)0.0029 (6)0.0000 (6)0.0020 (6)
C30.0147 (7)0.0180 (8)0.0164 (7)0.0002 (6)0.0024 (6)0.0010 (6)
C40.0198 (7)0.0204 (8)0.0177 (7)0.0030 (6)0.0010 (6)0.0023 (6)
C50.0244 (8)0.0166 (8)0.0240 (8)0.0013 (7)0.0004 (7)0.0029 (7)
C60.0214 (8)0.0187 (8)0.0259 (8)0.0028 (7)0.0023 (6)0.0023 (7)
C70.0190 (8)0.0210 (8)0.0211 (7)0.0004 (7)0.0038 (6)0.0001 (6)
C80.0152 (7)0.0172 (8)0.0174 (7)0.0014 (6)0.0015 (6)0.0002 (6)
C90.0167 (7)0.0184 (8)0.0182 (7)0.0003 (6)0.0028 (6)0.0011 (6)
C100.0205 (8)0.0146 (8)0.0194 (7)0.0006 (6)0.0032 (6)0.0017 (6)
C110.0219 (8)0.0229 (9)0.0167 (7)0.0023 (7)0.0009 (6)0.0016 (6)
C120.0183 (7)0.0193 (8)0.0206 (7)0.0029 (6)0.0045 (6)0.0016 (6)
C130.0242 (8)0.0151 (8)0.0273 (8)0.0022 (6)0.0021 (7)0.0019 (7)
C140.0233 (8)0.0197 (8)0.0235 (8)0.0045 (7)0.0021 (6)0.0007 (7)
C150.0292 (9)0.0241 (9)0.0273 (9)0.0034 (7)0.0026 (7)0.0043 (7)
C160.0198 (7)0.0155 (8)0.0169 (7)0.0025 (6)0.0003 (6)0.0019 (6)
C170.0223 (8)0.0177 (8)0.0195 (7)0.0003 (7)0.0012 (6)0.0019 (6)
C180.0225 (8)0.0172 (8)0.0175 (7)0.0023 (7)0.0026 (6)0.0030 (6)
C190.0277 (9)0.0235 (9)0.0228 (8)0.0052 (7)0.0056 (7)0.0009 (7)
C200.0196 (8)0.0334 (10)0.0292 (9)0.0080 (7)0.0048 (7)0.0012 (8)
C210.0199 (8)0.0326 (10)0.0270 (8)0.0012 (7)0.0014 (7)0.0003 (7)
C220.0218 (8)0.0241 (9)0.0219 (8)0.0012 (7)0.0002 (6)0.0020 (7)
C230.0205 (8)0.0171 (8)0.0159 (7)0.0023 (6)0.0020 (6)0.0027 (6)
C240.0211 (7)0.0161 (8)0.0159 (7)0.0018 (6)0.0009 (6)0.0008 (6)
C250.0167 (7)0.0251 (9)0.0280 (8)0.0019 (7)0.0019 (7)0.0059 (7)
C260.0220 (8)0.0236 (9)0.0269 (8)0.0008 (7)0.0032 (7)0.0091 (7)
C270.0228 (8)0.0184 (8)0.0195 (7)0.0041 (6)0.0028 (6)0.0009 (6)
C280.0169 (7)0.0220 (8)0.0184 (7)0.0028 (6)0.0018 (6)0.0038 (6)
C290.0189 (7)0.0183 (8)0.0167 (7)0.0029 (6)0.0001 (6)0.0011 (6)
C300.0252 (8)0.0270 (9)0.0269 (8)0.0060 (7)0.0014 (7)0.0060 (7)
Geometric parameters (Å, º) top
N1—C11.369 (2)C12—C151.507 (2)
N1—C91.4090 (19)C13—C141.381 (2)
N1—H10.886 (9)C13—H130.9500
N2—C21.301 (2)C14—H140.9500
N2—C31.3793 (19)C15—H15A0.9800
N3—C11.3096 (19)C15—H15B0.9800
N3—C81.3751 (19)C15—H15C0.9800
N4—C161.365 (2)C16—C171.439 (2)
N4—C241.4084 (19)C17—H170.9500
N4—H40.872 (9)C18—C191.406 (2)
N5—C171.299 (2)C18—C231.411 (2)
N5—C181.382 (2)C19—C201.368 (2)
N6—C161.314 (2)C19—H190.9500
N6—C231.3745 (19)C20—C211.405 (2)
C1—C21.440 (2)C20—H200.9500
C2—H20.9500C21—C221.371 (2)
C3—C41.405 (2)C21—H210.9500
C3—C81.415 (2)C22—C231.407 (2)
C4—C51.372 (2)C22—H220.9500
C4—H4A0.9500C24—C291.394 (2)
C5—C61.406 (2)C24—C251.397 (2)
C5—H50.9500C25—C261.386 (2)
C6—C71.372 (2)C25—H250.9500
C6—H60.9500C26—C271.390 (2)
C7—C81.407 (2)C26—H260.9500
C7—H70.9500C27—C281.386 (2)
C9—C101.393 (2)C27—C301.502 (2)
C9—C141.396 (2)C28—C291.378 (2)
C10—C111.389 (2)C28—H280.9500
C10—H100.9500C29—H290.9500
C11—C121.387 (2)C30—H30A0.9800
C11—H110.9500C30—H30B0.9800
C12—C131.390 (2)C30—H30C0.9800
C1—N1—C9130.07 (13)C12—C15—H15B109.5
C1—N1—H1113.7 (13)H15A—C15—H15B109.5
C9—N1—H1115.3 (13)C12—C15—H15C109.5
C2—N2—C3116.66 (13)H15A—C15—H15C109.5
C1—N3—C8116.08 (13)H15B—C15—H15C109.5
C16—N4—C24129.98 (13)N6—C16—N4122.10 (14)
C16—N4—H4115.4 (12)N6—C16—C17121.65 (14)
C24—N4—H4114.5 (12)N4—C16—C17116.24 (14)
C17—N5—C18116.44 (13)N5—C17—C16123.24 (14)
C16—N6—C23116.15 (13)N5—C17—H17118.4
N3—C1—N1122.78 (14)C16—C17—H17118.4
N3—C1—C2121.74 (14)N5—C18—C19120.06 (14)
N1—C1—C2115.48 (13)N5—C18—C23120.37 (14)
N2—C2—C1123.17 (14)C19—C18—C23119.57 (15)
N2—C2—H2118.4C20—C19—C18120.31 (15)
C1—C2—H2118.4C20—C19—H19119.8
N2—C3—C4119.67 (13)C18—C19—H19119.8
N2—C3—C8120.02 (14)C19—C20—C21120.13 (15)
C4—C3—C8120.31 (14)C19—C20—H20119.9
C5—C4—C3119.80 (14)C21—C20—H20119.9
C5—C4—H4A120.1C22—C21—C20120.72 (16)
C3—C4—H4A120.1C22—C21—H21119.6
C4—C5—C6120.05 (15)C20—C21—H21119.6
C4—C5—H5120.0C21—C22—C23120.01 (15)
C6—C5—H5120.0C21—C22—H22120.0
C7—C6—C5121.10 (15)C23—C22—H22120.0
C7—C6—H6119.4N6—C23—C22118.66 (14)
C5—C6—H6119.4N6—C23—C18122.09 (14)
C6—C7—C8119.96 (14)C22—C23—C18119.25 (14)
C6—C7—H7120.0C29—C24—C25118.58 (14)
C8—C7—H7120.0C29—C24—N4116.69 (14)
N3—C8—C7118.90 (13)C25—C24—N4124.72 (14)
N3—C8—C3122.33 (14)C26—C25—C24119.36 (15)
C7—C8—C3118.77 (14)C26—C25—H25120.3
C10—C9—C14119.13 (14)C24—C25—H25120.3
C10—C9—N1124.21 (14)C25—C26—C27122.46 (15)
C14—C9—N1116.65 (14)C25—C26—H26118.8
C11—C10—C9119.11 (14)C27—C26—H26118.8
C11—C10—H10120.4C28—C27—C26117.18 (14)
C9—C10—H10120.4C28—C27—C30121.66 (14)
C12—C11—C10122.51 (15)C26—C27—C30121.15 (15)
C12—C11—H11118.7C29—C28—C27121.58 (14)
C10—C11—H11118.7C29—C28—H28119.2
C11—C12—C13117.42 (14)C27—C28—H28119.2
C11—C12—C15121.65 (15)C28—C29—C24120.82 (14)
C13—C12—C15120.93 (15)C28—C29—H29119.6
C14—C13—C12121.35 (15)C24—C29—H29119.6
C14—C13—H13119.3C27—C30—H30A109.5
C12—C13—H13119.3C27—C30—H30B109.5
C13—C14—C9120.47 (15)H30A—C30—H30B109.5
C13—C14—H14119.8C27—C30—H30C109.5
C9—C14—H14119.8H30A—C30—H30C109.5
C12—C15—H15A109.5H30B—C30—H30C109.5
C8—N3—C1—N1179.27 (13)C23—N6—C16—N4178.95 (14)
C8—N3—C1—C20.5 (2)C23—N6—C16—C172.1 (2)
C9—N1—C1—N30.9 (2)C24—N4—C16—N64.0 (3)
C9—N1—C1—C2178.94 (14)C24—N4—C16—C17174.97 (14)
C3—N2—C2—C10.4 (2)C18—N5—C17—C161.9 (2)
N3—C1—C2—N20.2 (2)N6—C16—C17—N50.2 (2)
N1—C1—C2—N2179.62 (14)N4—C16—C17—N5179.18 (14)
C2—N2—C3—C4179.47 (14)C17—N5—C18—C19177.95 (15)
C2—N2—C3—C80.6 (2)C17—N5—C18—C232.1 (2)
N2—C3—C4—C5178.80 (14)N5—C18—C19—C20179.52 (15)
C8—C3—C4—C50.1 (2)C23—C18—C19—C200.5 (2)
C3—C4—C5—C60.2 (2)C18—C19—C20—C210.1 (3)
C4—C5—C6—C70.0 (2)C19—C20—C21—C220.6 (3)
C5—C6—C7—C80.4 (2)C20—C21—C22—C230.4 (3)
C1—N3—C8—C7179.76 (13)C16—N6—C23—C22178.58 (14)
C1—N3—C8—C30.3 (2)C16—N6—C23—C181.9 (2)
C6—C7—C8—N3178.90 (14)C21—C22—C23—N6179.75 (15)
C6—C7—C8—C30.6 (2)C21—C22—C23—C180.3 (2)
N2—C3—C8—N30.3 (2)N5—C18—C23—N60.2 (2)
C4—C3—C8—N3179.13 (14)C19—C18—C23—N6179.87 (14)
N2—C3—C8—C7179.19 (13)N5—C18—C23—C22179.32 (14)
C4—C3—C8—C70.3 (2)C19—C18—C23—C220.7 (2)
C1—N1—C9—C1015.1 (2)C16—N4—C24—C29176.07 (15)
C1—N1—C9—C14166.00 (15)C16—N4—C24—C253.4 (3)
C14—C9—C10—C110.3 (2)C29—C24—C25—C260.4 (2)
N1—C9—C10—C11178.57 (14)N4—C24—C25—C26179.90 (15)
C9—C10—C11—C120.4 (2)C24—C25—C26—C270.3 (3)
C10—C11—C12—C130.1 (2)C25—C26—C27—C280.9 (2)
C10—C11—C12—C15179.21 (14)C25—C26—C27—C30178.90 (15)
C11—C12—C13—C140.6 (2)C26—C27—C28—C290.8 (2)
C15—C12—C13—C14179.69 (15)C30—C27—C28—C29179.05 (14)
C12—C13—C14—C90.6 (2)C27—C28—C29—C240.1 (2)
C10—C9—C14—C130.1 (2)C25—C24—C29—C280.5 (2)
N1—C9—C14—C13179.11 (14)N4—C24—C29—C28179.91 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.89 (1)2.26 (1)3.114 (2)163 (2)
N4—H4···N2i0.87 (1)2.19 (1)3.017 (2)157 (2)
Symmetry code: (i) x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H13N3
Mr235.28
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)100
a, b, c (Å)12.2081 (9), 11.3720 (9), 35.097 (3)
V3)4872.5 (6)
Z16
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.15 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
26747, 5592, 4089
Rint0.051
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.112, 1.03
No. of reflections5592
No. of parameters335
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.89 (1)2.26 (1)3.114 (2)163 (2)
N4—H4···N2i0.87 (1)2.19 (1)3.017 (2)157 (2)
Symmetry code: (i) x+3/2, y+1/2, z.
 

Acknowledgements

We thank the University of Malaya for supporting this study (FS358/2008 A).

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFairuz, Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2441.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationIdris, A., Wan Saffiee, W. A. M., Abdullah, Z., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o2443.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2440.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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