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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o93.
Published online 2008 December 10. doi:  10.1107/S1600536808041160
PMCID: PMC2968000

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

Abstract

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 [triangle]); for that of N-(pyrazin-2-yl)-4-toluidine, see: Wan Saffiee et al. (2008 [triangle]). The title compound is isostructural with N-(quinoxalin-2-yl)-4-chloro­aniline; see: Idris et al. (2008 [triangle]).

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Object name is e-65-00o93-scheme1.jpg

Experimental

Crystal data

  • C15H13N3
  • M r = 235.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o93-efi1.jpg
  • 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)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041160/tk2339sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041160/tk2339Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

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

Bruker SMART APEX diffractometer4089 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
graphiteθmax = 27.5°, θmin = 1.2°
ω scansh = −15→15
26747 measured reflectionsk = −14→9
5592 independent reflectionsl = −45→45

Refinement

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 = 1.03w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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—N4−178.95 (14)
C8—N3—C1—C2−0.5 (2)C23—N6—C16—C172.1 (2)
C9—N1—C1—N3−0.9 (2)C24—N4—C16—N6−4.0 (3)
C9—N1—C1—C2178.94 (14)C24—N4—C16—C17174.97 (14)
C3—N2—C2—C10.4 (2)C18—N5—C17—C16−1.9 (2)
N3—C1—C2—N20.2 (2)N6—C16—C17—N5−0.2 (2)
N1—C1—C2—N2−179.62 (14)N4—C16—C17—N5−179.18 (14)
C2—N2—C3—C4−179.47 (14)C17—N5—C18—C19−177.95 (15)
C2—N2—C3—C8−0.6 (2)C17—N5—C18—C232.1 (2)
N2—C3—C4—C5178.80 (14)N5—C18—C19—C20−179.52 (15)
C8—C3—C4—C5−0.1 (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—C22−0.6 (3)
C5—C6—C7—C8−0.4 (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—C18−1.9 (2)
C6—C7—C8—N3−178.90 (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—N6−0.2 (2)
C4—C3—C8—N3179.13 (14)C19—C18—C23—N6179.87 (14)
N2—C3—C8—C7−179.19 (13)N5—C18—C23—C22179.32 (14)
C4—C3—C8—C7−0.3 (2)C19—C18—C23—C22−0.7 (2)
C1—N1—C9—C10−15.1 (2)C16—N4—C24—C29−176.07 (15)
C1—N1—C9—C14166.00 (15)C16—N4—C24—C253.4 (3)
C14—C9—C10—C110.3 (2)C29—C24—C25—C26−0.4 (2)
N1—C9—C10—C11−178.57 (14)N4—C24—C25—C26−179.90 (15)
C9—C10—C11—C12−0.4 (2)C24—C25—C26—C27−0.3 (3)
C10—C11—C12—C13−0.1 (2)C25—C26—C27—C280.9 (2)
C10—C11—C12—C15−179.21 (14)C25—C26—C27—C30−178.90 (15)
C11—C12—C13—C140.6 (2)C26—C27—C28—C29−0.8 (2)
C15—C12—C13—C14179.69 (15)C30—C27—C28—C29179.05 (14)
C12—C13—C14—C9−0.6 (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—C28−179.91 (13)

Hydrogen-bond geometry (Å, °)

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 codes: (i) −x+3/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2339).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fairuz, Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2441. [PMC free article] [PubMed]
  • Idris, A., Wan Saffiee, W. A. M., Abdullah, Z., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o2443. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2440. [PMC free article] [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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