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

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

doi:10.1107/S1600536808041160

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o93

doi:10.1107/S1600536808041160

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

Wan Ainna Mardhiah Wan Saffiee,^a Azila Idris,^a Zaharah Aiyub,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^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 ); 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

Crystal data

C₁₅H₁₃N₃
M_r = 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)
R_int = 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
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

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.

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

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

C₁₅H₁₃N₃	F(000) = 1984
M_r = 235.28	D_x = 1.283 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3585 reflections
a = 12.2081 (9) Å	θ = 2.5–27.6°
b = 11.3720 (9) Å	µ = 0.08 mm⁻¹
c = 35.097 (3) Å	T = 100 K
V = 4872.5 (6) Å³	Block, yellow
Z = 16	0.40 × 0.15 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	4089 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 27.5°, θ_min = 1.2°
ω scans	h = −15→15
26747 measured reflections	k = −14→9
5592 independent reflections	l = −45→45

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0453P)² + 2.027P] where P = (F_o² + 2F_c²)/3
5592 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₃N₃	V = 4872.5 (6) Å³
M_r = 235.28	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 12.2081 (9) Å	µ = 0.08 mm⁻¹
b = 11.3720 (9) Å	T = 100 K
c = 35.097 (3) Å	0.40 × 0.15 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	4089 reflections with I > 2σ(I)
26747 measured reflections	R_int = 0.051
5592 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
5592 reflections	Δρ_min = −0.25 e Å⁻³
335 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.48774 (11)	0.63997 (12)	0.55869 (4)	0.0200 (3)
N2	0.54428 (10)	0.38803 (11)	0.61730 (3)	0.0183 (3)
N3	0.41112 (10)	0.45078 (11)	0.55410 (3)	0.0169 (3)
N4	0.78134 (10)	0.95678 (12)	0.67401 (4)	0.0194 (3)
N5	0.57078 (11)	0.78948 (12)	0.62719 (4)	0.0207 (3)
N6	0.59133 (10)	0.96931 (11)	0.68290 (3)	0.0183 (3)
C1	0.47718 (12)	0.52591 (13)	0.57059 (4)	0.0166 (3)
C2	0.54419 (12)	0.49311 (14)	0.60265 (4)	0.0188 (3)
H2	0.5906	0.5510	0.6136	0.023*
C3	0.47637 (12)	0.30629 (13)	0.60042 (4)	0.0164 (3)
C4	0.47172 (12)	0.19136 (14)	0.61498 (4)	0.0193 (3)
H4A	0.5162	0.1697	0.6361	0.023*
C5	0.40277 (13)	0.11048 (14)	0.59870 (4)	0.0217 (3)
H5	0.3993	0.0328	0.6086	0.026*
C6	0.33726 (13)	0.14250 (14)	0.56743 (4)	0.0220 (3)
H6	0.2897	0.0859	0.5563	0.026*
C7	0.34082 (12)	0.25413 (14)	0.55266 (4)	0.0204 (3)
H7	0.2964	0.2741	0.5314	0.024*
C8	0.41034 (12)	0.33894 (13)	0.56900 (4)	0.0166 (3)
C9	0.43642 (12)	0.69945 (14)	0.52834 (4)	0.0178 (3)
C10	0.38087 (12)	0.64377 (14)	0.49874 (4)	0.0182 (3)
H10	0.3741	0.5606	0.4983	0.022*
C11	0.33549 (13)	0.71156 (14)	0.46985 (4)	0.0205 (3)
H11	0.2981	0.6731	0.4497	0.025*
C12	0.34273 (12)	0.83326 (14)	0.46935 (4)	0.0194 (3)
C13	0.39785 (13)	0.88706 (14)	0.49930 (5)	0.0222 (3)
H13	0.4036	0.9704	0.4999	0.027*
C14	0.44450 (13)	0.82189 (14)	0.52828 (5)	0.0222 (3)
H14	0.4823	0.8607	0.5483	0.027*
C15	0.29166 (14)	0.90520 (15)	0.43798 (5)	0.0269 (4)
H15A	0.3407	0.9702	0.4312	0.040*
H15B	0.2213	0.9369	0.4467	0.040*
H15C	0.2797	0.8553	0.4156	0.040*
C16	0.67680 (13)	0.92171 (13)	0.66615 (4)	0.0174 (3)
C17	0.66505 (13)	0.83080 (14)	0.63794 (4)	0.0198 (3)
H17	0.7294	0.7994	0.6266	0.024*
C18	0.47952 (13)	0.83502 (14)	0.64525 (4)	0.0190 (3)
C19	0.37461 (14)	0.79237 (15)	0.63617 (5)	0.0247 (4)
H19	0.3666	0.7318	0.6177	0.030*
C20	0.28394 (14)	0.83771 (16)	0.65375 (5)	0.0274 (4)
H20	0.2133	0.8084	0.6475	0.033*
C21	0.29513 (13)	0.92756 (16)	0.68096 (5)	0.0265 (4)
H21	0.2317	0.9591	0.6929	0.032*
C22	0.39656 (13)	0.97021 (15)	0.69051 (4)	0.0226 (4)
H22	0.4032	1.0306	0.7091	0.027*
C23	0.49085 (12)	0.92445 (14)	0.67284 (4)	0.0178 (3)
C24	0.81936 (13)	1.04794 (13)	0.69774 (4)	0.0177 (3)
C25	0.75245 (13)	1.11936 (15)	0.72024 (4)	0.0233 (4)
H25	0.6753	1.1083	0.7203	0.028*
C26	0.79967 (13)	1.20656 (15)	0.74242 (5)	0.0242 (4)
H26	0.7535	1.2550	0.7575	0.029*
C27	0.91210 (13)	1.22577 (14)	0.74339 (4)	0.0202 (3)
C28	0.97681 (12)	1.15459 (14)	0.72058 (4)	0.0191 (3)
H28	1.0539	1.1662	0.7204	0.023*
C29	0.93207 (12)	1.06744 (14)	0.69819 (4)	0.0180 (3)
H29	0.9786	1.0200	0.6829	0.022*
C30	0.96087 (14)	1.31961 (15)	0.76827 (5)	0.0263 (4)
H30A	1.0407	1.3193	0.7654	0.040*
H30B	0.9417	1.3042	0.7949	0.040*
H30C	0.9320	1.3965	0.7607	0.040*
H1	0.5235 (14)	0.6854 (15)	0.5750 (5)	0.038 (6)*
H4	0.8327 (12)	0.9193 (14)	0.6617 (5)	0.027 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0240 (7)	0.0156 (7)	0.0204 (6)	−0.0025 (6)	−0.0051 (5)	0.0004 (5)
N2	0.0179 (6)	0.0195 (7)	0.0176 (6)	−0.0004 (5)	−0.0005 (5)	−0.0004 (5)
N3	0.0164 (6)	0.0162 (7)	0.0181 (6)	0.0003 (5)	0.0000 (5)	0.0003 (5)
N4	0.0166 (6)	0.0193 (7)	0.0223 (7)	−0.0015 (6)	0.0030 (5)	−0.0053 (5)
N5	0.0234 (7)	0.0180 (7)	0.0208 (6)	−0.0017 (6)	−0.0018 (5)	−0.0008 (5)
N6	0.0181 (6)	0.0189 (7)	0.0179 (6)	−0.0022 (5)	−0.0003 (5)	−0.0008 (5)
C1	0.0162 (7)	0.0163 (8)	0.0174 (7)	0.0000 (6)	0.0021 (6)	−0.0006 (6)
C2	0.0190 (7)	0.0195 (8)	0.0180 (7)	−0.0029 (6)	0.0000 (6)	−0.0020 (6)
C3	0.0147 (7)	0.0180 (8)	0.0164 (7)	0.0002 (6)	0.0024 (6)	−0.0010 (6)
C4	0.0198 (7)	0.0204 (8)	0.0177 (7)	0.0030 (6)	−0.0010 (6)	0.0023 (6)
C5	0.0244 (8)	0.0166 (8)	0.0240 (8)	0.0013 (7)	0.0004 (7)	0.0029 (7)
C6	0.0214 (8)	0.0187 (8)	0.0259 (8)	−0.0028 (7)	−0.0023 (6)	−0.0023 (7)
C7	0.0190 (8)	0.0210 (8)	0.0211 (7)	−0.0004 (7)	−0.0038 (6)	0.0001 (6)
C8	0.0152 (7)	0.0172 (8)	0.0174 (7)	0.0014 (6)	0.0015 (6)	0.0002 (6)
C9	0.0167 (7)	0.0184 (8)	0.0182 (7)	0.0003 (6)	0.0028 (6)	0.0011 (6)
C10	0.0205 (8)	0.0146 (8)	0.0194 (7)	0.0006 (6)	0.0032 (6)	−0.0017 (6)
C11	0.0219 (8)	0.0229 (9)	0.0167 (7)	0.0023 (7)	0.0009 (6)	−0.0016 (6)
C12	0.0183 (7)	0.0193 (8)	0.0206 (7)	0.0029 (6)	0.0045 (6)	0.0016 (6)
C13	0.0242 (8)	0.0151 (8)	0.0273 (8)	−0.0022 (6)	0.0021 (7)	0.0019 (7)
C14	0.0233 (8)	0.0197 (8)	0.0235 (8)	−0.0045 (7)	−0.0021 (6)	−0.0007 (7)
C15	0.0292 (9)	0.0241 (9)	0.0273 (9)	0.0034 (7)	−0.0026 (7)	0.0043 (7)
C16	0.0198 (7)	0.0155 (8)	0.0169 (7)	−0.0025 (6)	0.0003 (6)	0.0019 (6)
C17	0.0223 (8)	0.0177 (8)	0.0195 (7)	−0.0003 (7)	0.0012 (6)	−0.0019 (6)
C18	0.0225 (8)	0.0172 (8)	0.0175 (7)	−0.0023 (7)	−0.0026 (6)	0.0030 (6)
C19	0.0277 (9)	0.0235 (9)	0.0228 (8)	−0.0052 (7)	−0.0056 (7)	−0.0009 (7)
C20	0.0196 (8)	0.0334 (10)	0.0292 (9)	−0.0080 (7)	−0.0048 (7)	0.0012 (8)
C21	0.0199 (8)	0.0326 (10)	0.0270 (8)	−0.0012 (7)	0.0014 (7)	0.0003 (7)
C22	0.0218 (8)	0.0241 (9)	0.0219 (8)	−0.0012 (7)	0.0002 (6)	−0.0020 (7)
C23	0.0205 (8)	0.0171 (8)	0.0159 (7)	−0.0023 (6)	−0.0020 (6)	0.0027 (6)
C24	0.0211 (7)	0.0161 (8)	0.0159 (7)	−0.0018 (6)	−0.0009 (6)	0.0008 (6)
C25	0.0167 (7)	0.0251 (9)	0.0280 (8)	−0.0019 (7)	0.0019 (7)	−0.0059 (7)
C26	0.0220 (8)	0.0236 (9)	0.0269 (8)	−0.0008 (7)	0.0032 (7)	−0.0091 (7)
C27	0.0228 (8)	0.0184 (8)	0.0195 (7)	−0.0041 (6)	−0.0028 (6)	0.0009 (6)
C28	0.0169 (7)	0.0220 (8)	0.0184 (7)	−0.0028 (6)	−0.0018 (6)	0.0038 (6)
C29	0.0189 (7)	0.0183 (8)	0.0167 (7)	0.0029 (6)	0.0001 (6)	0.0011 (6)
C30	0.0252 (8)	0.0270 (9)	0.0269 (8)	−0.0060 (7)	−0.0014 (7)	−0.0060 (7)

Geometric parameters (Å, º) top

N1—C1	1.369 (2)	C12—C15	1.507 (2)
N1—C9	1.4090 (19)	C13—C14	1.381 (2)
N1—H1	0.886 (9)	C13—H13	0.9500
N2—C2	1.301 (2)	C14—H14	0.9500
N2—C3	1.3793 (19)	C15—H15A	0.9800
N3—C1	1.3096 (19)	C15—H15B	0.9800
N3—C8	1.3751 (19)	C15—H15C	0.9800
N4—C16	1.365 (2)	C16—C17	1.439 (2)
N4—C24	1.4084 (19)	C17—H17	0.9500
N4—H4	0.872 (9)	C18—C19	1.406 (2)
N5—C17	1.299 (2)	C18—C23	1.411 (2)
N5—C18	1.382 (2)	C19—C20	1.368 (2)
N6—C16	1.314 (2)	C19—H19	0.9500
N6—C23	1.3745 (19)	C20—C21	1.405 (2)
C1—C2	1.440 (2)	C20—H20	0.9500
C2—H2	0.9500	C21—C22	1.371 (2)
C3—C4	1.405 (2)	C21—H21	0.9500
C3—C8	1.415 (2)	C22—C23	1.407 (2)
C4—C5	1.372 (2)	C22—H22	0.9500
C4—H4A	0.9500	C24—C29	1.394 (2)
C5—C6	1.406 (2)	C24—C25	1.397 (2)
C5—H5	0.9500	C25—C26	1.386 (2)
C6—C7	1.372 (2)	C25—H25	0.9500
C6—H6	0.9500	C26—C27	1.390 (2)
C7—C8	1.407 (2)	C26—H26	0.9500
C7—H7	0.9500	C27—C28	1.386 (2)
C9—C10	1.393 (2)	C27—C30	1.502 (2)
C9—C14	1.396 (2)	C28—C29	1.378 (2)
C10—C11	1.389 (2)	C28—H28	0.9500
C10—H10	0.9500	C29—H29	0.9500
C11—C12	1.387 (2)	C30—H30A	0.9800
C11—H11	0.9500	C30—H30B	0.9800
C12—C13	1.390 (2)	C30—H30C	0.9800

C1—N1—C9	130.07 (13)	C12—C15—H15B	109.5
C1—N1—H1	113.7 (13)	H15A—C15—H15B	109.5
C9—N1—H1	115.3 (13)	C12—C15—H15C	109.5
C2—N2—C3	116.66 (13)	H15A—C15—H15C	109.5
C1—N3—C8	116.08 (13)	H15B—C15—H15C	109.5
C16—N4—C24	129.98 (13)	N6—C16—N4	122.10 (14)
C16—N4—H4	115.4 (12)	N6—C16—C17	121.65 (14)
C24—N4—H4	114.5 (12)	N4—C16—C17	116.24 (14)
C17—N5—C18	116.44 (13)	N5—C17—C16	123.24 (14)
C16—N6—C23	116.15 (13)	N5—C17—H17	118.4
N3—C1—N1	122.78 (14)	C16—C17—H17	118.4
N3—C1—C2	121.74 (14)	N5—C18—C19	120.06 (14)
N1—C1—C2	115.48 (13)	N5—C18—C23	120.37 (14)
N2—C2—C1	123.17 (14)	C19—C18—C23	119.57 (15)
N2—C2—H2	118.4	C20—C19—C18	120.31 (15)
C1—C2—H2	118.4	C20—C19—H19	119.8
N2—C3—C4	119.67 (13)	C18—C19—H19	119.8
N2—C3—C8	120.02 (14)	C19—C20—C21	120.13 (15)
C4—C3—C8	120.31 (14)	C19—C20—H20	119.9
C5—C4—C3	119.80 (14)	C21—C20—H20	119.9
C5—C4—H4A	120.1	C22—C21—C20	120.72 (16)
C3—C4—H4A	120.1	C22—C21—H21	119.6
C4—C5—C6	120.05 (15)	C20—C21—H21	119.6
C4—C5—H5	120.0	C21—C22—C23	120.01 (15)
C6—C5—H5	120.0	C21—C22—H22	120.0
C7—C6—C5	121.10 (15)	C23—C22—H22	120.0
C7—C6—H6	119.4	N6—C23—C22	118.66 (14)
C5—C6—H6	119.4	N6—C23—C18	122.09 (14)
C6—C7—C8	119.96 (14)	C22—C23—C18	119.25 (14)
C6—C7—H7	120.0	C29—C24—C25	118.58 (14)
C8—C7—H7	120.0	C29—C24—N4	116.69 (14)
N3—C8—C7	118.90 (13)	C25—C24—N4	124.72 (14)
N3—C8—C3	122.33 (14)	C26—C25—C24	119.36 (15)
C7—C8—C3	118.77 (14)	C26—C25—H25	120.3
C10—C9—C14	119.13 (14)	C24—C25—H25	120.3
C10—C9—N1	124.21 (14)	C25—C26—C27	122.46 (15)
C14—C9—N1	116.65 (14)	C25—C26—H26	118.8
C11—C10—C9	119.11 (14)	C27—C26—H26	118.8
C11—C10—H10	120.4	C28—C27—C26	117.18 (14)
C9—C10—H10	120.4	C28—C27—C30	121.66 (14)
C12—C11—C10	122.51 (15)	C26—C27—C30	121.15 (15)
C12—C11—H11	118.7	C29—C28—C27	121.58 (14)
C10—C11—H11	118.7	C29—C28—H28	119.2
C11—C12—C13	117.42 (14)	C27—C28—H28	119.2
C11—C12—C15	121.65 (15)	C28—C29—C24	120.82 (14)
C13—C12—C15	120.93 (15)	C28—C29—H29	119.6
C14—C13—C12	121.35 (15)	C24—C29—H29	119.6
C14—C13—H13	119.3	C27—C30—H30A	109.5
C12—C13—H13	119.3	C27—C30—H30B	109.5
C13—C14—C9	120.47 (15)	H30A—C30—H30B	109.5
C13—C14—H14	119.8	C27—C30—H30C	109.5
C9—C14—H14	119.8	H30A—C30—H30C	109.5
C12—C15—H15A	109.5	H30B—C30—H30C	109.5

C8—N3—C1—N1	179.27 (13)	C23—N6—C16—N4	−178.95 (14)
C8—N3—C1—C2	−0.5 (2)	C23—N6—C16—C17	2.1 (2)
C9—N1—C1—N3	−0.9 (2)	C24—N4—C16—N6	−4.0 (3)
C9—N1—C1—C2	178.94 (14)	C24—N4—C16—C17	174.97 (14)
C3—N2—C2—C1	0.4 (2)	C18—N5—C17—C16	−1.9 (2)
N3—C1—C2—N2	0.2 (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—C23	2.1 (2)
N2—C3—C4—C5	178.80 (14)	N5—C18—C19—C20	−179.52 (15)
C8—C3—C4—C5	−0.1 (2)	C23—C18—C19—C20	0.5 (2)
C3—C4—C5—C6	0.2 (2)	C18—C19—C20—C21	0.1 (3)
C4—C5—C6—C7	0.0 (2)	C19—C20—C21—C22	−0.6 (3)
C5—C6—C7—C8	−0.4 (2)	C20—C21—C22—C23	0.4 (3)
C1—N3—C8—C7	179.76 (13)	C16—N6—C23—C22	178.58 (14)
C1—N3—C8—C3	0.3 (2)	C16—N6—C23—C18	−1.9 (2)
C6—C7—C8—N3	−178.90 (14)	C21—C22—C23—N6	179.75 (15)
C6—C7—C8—C3	0.6 (2)	C21—C22—C23—C18	0.3 (2)
N2—C3—C8—N3	0.3 (2)	N5—C18—C23—N6	−0.2 (2)
C4—C3—C8—N3	179.13 (14)	C19—C18—C23—N6	179.87 (14)
N2—C3—C8—C7	−179.19 (13)	N5—C18—C23—C22	179.32 (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—C14	166.00 (15)	C16—N4—C24—C25	3.4 (3)
C14—C9—C10—C11	0.3 (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—C28	0.9 (2)
C10—C11—C12—C15	−179.21 (14)	C25—C26—C27—C30	−178.90 (15)
C11—C12—C13—C14	0.6 (2)	C26—C27—C28—C29	−0.8 (2)
C15—C12—C13—C14	179.69 (15)	C30—C27—C28—C29	179.05 (14)
C12—C13—C14—C9	−0.6 (2)	C27—C28—C29—C24	0.1 (2)
C10—C9—C14—C13	0.1 (2)	C25—C24—C29—C28	0.5 (2)
N1—C9—C14—C13	179.11 (14)	N4—C24—C29—C28	−179.91 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃
M_r	235.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	12.2081 (9), 11.3720 (9), 35.097 (3)
V (Å³)	4872.5 (6)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26747, 5592, 4089
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.03
No. of reflections	5592
No. of parameters	335
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+3/2, y+1/2, z.

Acknowledgements

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

References

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