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Acta Cryst. (2009). E65, o93    [ doi:10.1107/S1600536808041160 ]

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

W. A. M. Wan Saffiee, A. Idris, Z. Aiyub, Z. Abdullah and S. W. Ng

Abstract top

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 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 m−3
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 mm−1
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
graphiteθmax = 27.5°, θmin = 1.2°
ω scansh = −15→15
26747 measured reflectionsk = −14→9
5592 independent reflectionsl = −45→45
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 Å−3
2 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C15H13N3V = 4872.5 (6) Å3
Mr = 235.28Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 12.2081 (9) ŵ = 0.08 mm−1
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 reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112Δρmax = 0.25 e Å−3
S = 1.03Δρmin = −0.25 e Å−3
5592 reflectionsAbsolute structure: ?
335 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
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, °) 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—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, °) 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 codes: (i) −x+3/2, y+1/2, z.
Table 1
Hydrogen-bond geometry (Å, °) 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 codes: (i) −x+3/2, y+1/2, z.
Acknowledgements top

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

references
References top

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Wan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2440.

Westrip, S. P. (2009). publCIF. In preparation.