4-[4-(Diethyl-amino)benzyl-ideneamino]-4H-1,2,4-triazole.

The title compound, C(13)H(17)N(5), is a Schiff base synthesized by the reaction of 4-amino-4H-1,2,4-triazole and 4-(diethyl-amino)benzaldehyde. The triazole ring forms a dihedral angle of 5.77 (16)° with the benzene ring. The crystal structure is stabilized by an inter-molecular C-H⋯N hydrogen bond.

Related literature

For related literature, see: Zhu et al. (2000 ▶), Atalay et al. (2003 ▶); Petek et al. (2004 ▶); Brasselet et al. (1999 ▶); Cornelissen et al. (1992 ▶); Demirbs & Ugurluoglu Demirbas (2002 ▶); Fujigaya et al. (2003 ▶); Garcia et al. (1997 ▶); Kahn & Martinez (1998 ▶); Moliner et al. (2001 ▶); Tozkoparan et al. (2000 ▶); Turan-Zitouni et al. (1999 ▶).

Experimental

Crystal data

C13H17N5

M = 243.32

Orthorhombic,

a = 7.740 (3) Å

b = 9.238 (4) Å

c = 18.497 (7) Å

V = 1322.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.37 × 0.35 × 0.11 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.992

6650 measured reflections

1359 independent reflections

895 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.131

S = 1.09

1359 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009100/rz2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009100/rz2200Isup2.hkl

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

C13H17N5	F000 = 520
Mr = 243.32	Dx = 1.222 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 870 reflections
a = 7.740 (3) Å	θ = 2.5–20.5º
b = 9.238 (4) Å	µ = 0.08 mm−1
c = 18.497 (7) Å	T = 293 (2) K
V = 1322.5 (9) Å3	Block, yellow
Z = 4	0.37 × 0.35 × 0.11 mm

Bruker APEX2 CCD area-detector diffractometer	1359 independent reflections
Radiation source: fine-focus sealed tube	895 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.075
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.972, Tmax = 0.992	k = −10→10
6650 measured reflections	l = −21→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0187P)2 + 0.429P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1359 reflections	Δρmax = 0.19 e Å−3
165 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	1.0028 (7)	0.8829 (5)	−0.2061 (3)	0.0777 (15)
H1	1.0615	0.8029	−0.2241	0.093*
C2	0.8502 (7)	1.0221 (5)	−0.1387 (3)	0.0888 (17)
H2	0.7824	1.0569	−0.1010	0.107*
C3	0.9580 (6)	0.6644 (4)	−0.0936 (2)	0.0632 (12)
H3	1.0140	0.6437	−0.1368	0.076*
C4	0.9482 (6)	0.5533 (4)	−0.0388 (2)	0.0562 (11)
C5	0.8680 (7)	0.5730 (4)	0.0283 (2)	0.0667 (13)
H5	0.8150	0.6611	0.0384	0.080*
C6	0.8654 (6)	0.4652 (4)	0.0798 (2)	0.0629 (13)
H6	0.8085	0.4815	0.1234	0.076*
C7	0.9468 (6)	0.3314 (4)	0.0680 (2)	0.0582 (11)
C8	1.0235 (6)	0.3114 (4)	−0.0006 (2)	0.0635 (12)
H8	1.0746	0.2231	−0.0117	0.076*
C9	1.0236 (6)	0.4195 (4)	−0.0505 (2)	0.0642 (12)
H9	1.0770	0.4026	−0.0948	0.077*
C10	1.0615 (7)	0.0993 (4)	0.1119 (2)	0.0684 (13)
H10A	1.1077	0.0746	0.1591	0.082*
H10B	1.1583	0.1240	0.0810	0.082*
C11	0.9734 (7)	−0.0308 (4)	0.0814 (3)	0.0824 (15)
H11A	0.8749	−0.0546	0.1106	0.124*
H11B	1.0523	−0.1110	0.0809	0.124*
H11C	0.9362	−0.0106	0.0329	0.124*
C12	0.8512 (7)	0.2348 (5)	0.1858 (2)	0.0754 (14)
H12A	0.8145	0.1383	0.1997	0.091*
H12B	0.7483	0.2917	0.1765	0.091*
C13	0.9488 (9)	0.3017 (6)	0.2477 (3)	0.112 (2)
H13A	1.0464	0.2421	0.2596	0.168*
H13B	0.8742	0.3094	0.2890	0.168*
H13C	0.9882	0.3964	0.2341	0.168*
N1	0.8934 (7)	1.0979 (5)	−0.1959 (3)	0.1007 (15)
N2	0.9902 (7)	1.0065 (5)	−0.2379 (2)	0.0907 (14)
N3	0.9164 (5)	0.8878 (4)	−0.1417 (2)	0.0651 (10)
N4	0.8933 (5)	0.7886 (4)	−0.08490 (19)	0.0679 (11)
N5	0.9521 (5)	0.2252 (3)	0.11934 (19)	0.0654 (10)

	U11	U22	U33	U12	U13	U23
C1	0.109 (5)	0.067 (3)	0.057 (3)	−0.009 (3)	−0.003 (3)	−0.004 (2)
C2	0.103 (5)	0.079 (3)	0.084 (4)	0.022 (3)	0.012 (3)	0.010 (3)
C3	0.077 (3)	0.069 (3)	0.044 (3)	−0.002 (3)	0.002 (2)	−0.001 (2)
C4	0.065 (3)	0.057 (2)	0.047 (2)	−0.003 (2)	0.001 (2)	−0.0034 (19)
C5	0.085 (4)	0.056 (2)	0.059 (3)	0.005 (2)	0.006 (2)	−0.008 (2)
C6	0.081 (4)	0.062 (3)	0.045 (3)	0.005 (2)	0.012 (2)	−0.004 (2)
C7	0.064 (3)	0.061 (2)	0.049 (3)	−0.006 (2)	0.002 (2)	−0.005 (2)
C8	0.075 (3)	0.060 (2)	0.056 (3)	0.007 (2)	0.006 (2)	−0.004 (2)
C9	0.068 (3)	0.069 (3)	0.055 (3)	0.001 (2)	0.010 (2)	−0.003 (2)
C10	0.079 (3)	0.069 (3)	0.057 (3)	0.010 (3)	0.001 (2)	0.010 (2)
C11	0.097 (4)	0.073 (3)	0.077 (4)	0.008 (3)	−0.006 (3)	−0.003 (3)
C12	0.092 (4)	0.077 (3)	0.058 (3)	−0.008 (3)	0.011 (3)	−0.001 (2)
C13	0.143 (6)	0.140 (4)	0.053 (3)	−0.027 (5)	0.005 (4)	−0.024 (3)
N1	0.117 (4)	0.082 (3)	0.104 (4)	0.009 (3)	0.003 (3)	0.025 (3)
N2	0.125 (4)	0.078 (3)	0.070 (3)	−0.016 (3)	−0.002 (3)	0.012 (2)
N3	0.081 (3)	0.061 (2)	0.054 (2)	−0.002 (2)	0.000 (2)	0.0043 (18)
N4	0.087 (3)	0.061 (2)	0.056 (2)	0.002 (2)	0.002 (2)	0.0061 (19)
N5	0.081 (3)	0.067 (2)	0.049 (2)	0.005 (2)	0.009 (2)	0.0040 (18)

C1—N2	1.288 (6)	C8—H8	0.9300
C1—N3	1.366 (6)	C9—H9	0.9300
C1—H1	0.9300	C10—N5	1.445 (5)
C2—N1	1.313 (6)	C10—C11	1.493 (6)
C2—N3	1.344 (5)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—N4	1.262 (5)	C11—H11A	0.9600
C3—C4	1.444 (5)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C9	1.384 (6)	C12—N5	1.459 (6)
C4—C5	1.400 (6)	C12—C13	1.505 (7)
C5—C6	1.378 (6)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—C7	1.405 (5)	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—N5	1.366 (5)	C13—H13C	0.9600
C7—C8	1.412 (6)	N1—N2	1.369 (6)
C8—C9	1.361 (5)	N3—N4	1.406 (4)
N2—C1—N3	109.4 (5)	N5—C10—H10B	108.6
N2—C1—H1	125.3	C11—C10—H10B	108.6
N3—C1—H1	125.3	H10A—C10—H10B	107.6
N1—C2—N3	111.2 (5)	C10—C11—H11A	109.5
N1—C2—H2	124.4	C10—C11—H11B	109.5
N3—C2—H2	124.4	H11A—C11—H11B	109.5
N4—C3—C4	122.4 (4)	C10—C11—H11C	109.5
N4—C3—H3	118.8	H11A—C11—H11C	109.5
C4—C3—H3	118.8	H11B—C11—H11C	109.5
C9—C4—C5	116.2 (4)	N5—C12—C13	113.4 (4)
C9—C4—C3	120.2 (4)	N5—C12—H12A	108.9
C5—C4—C3	123.6 (4)	C13—C12—H12A	108.9
C6—C5—C4	121.7 (4)	N5—C12—H12B	108.9
C6—C5—H5	119.1	C13—C12—H12B	108.9
C4—C5—H5	119.1	H12A—C12—H12B	107.7
C5—C6—C7	121.4 (4)	C12—C13—H13A	109.5
C5—C6—H6	119.3	C12—C13—H13B	109.5
C7—C6—H6	119.3	H13A—C13—H13B	109.5
N5—C7—C6	122.5 (4)	C12—C13—H13C	109.5
N5—C7—C8	121.2 (4)	H13A—C13—H13C	109.5
C6—C7—C8	116.3 (4)	H13B—C13—H13C	109.5
C9—C8—C7	121.0 (4)	C2—N1—N2	105.5 (4)
C9—C8—H8	119.5	C1—N2—N1	109.2 (5)
C7—C8—H8	119.5	C2—N3—C1	104.7 (4)
C8—C9—C4	123.3 (4)	C2—N3—N4	121.5 (4)
C8—C9—H9	118.4	C1—N3—N4	133.8 (4)
C4—C9—H9	118.4	C3—N4—N3	116.6 (4)
N5—C10—C11	114.6 (4)	C7—N5—C10	121.9 (3)
N5—C10—H10A	108.6	C7—N5—C12	121.8 (4)
C11—C10—H10A	108.6	C10—N5—C12	116.3 (3)
N4—C3—C4—C9	−179.0 (5)	N1—C2—N3—C1	−1.1 (6)
N4—C3—C4—C5	−0.4 (7)	N1—C2—N3—N4	177.3 (4)
C9—C4—C5—C6	0.4 (7)	N2—C1—N3—C2	1.0 (6)
C3—C4—C5—C6	−178.3 (4)	N2—C1—N3—N4	−177.2 (4)
C4—C5—C6—C7	1.5 (7)	C4—C3—N4—N3	178.2 (4)
C5—C6—C7—N5	177.2 (4)	C2—N3—N4—C3	178.8 (5)
C5—C6—C7—C8	−3.0 (7)	C1—N3—N4—C3	−3.3 (7)
N5—C7—C8—C9	−177.5 (4)	C6—C7—N5—C10	−168.6 (4)
C6—C7—C8—C9	2.7 (7)	C8—C7—N5—C10	11.6 (6)
C7—C8—C9—C4	−1.0 (7)	C6—C7—N5—C12	9.5 (6)
C5—C4—C9—C8	−0.6 (7)	C8—C7—N5—C12	−170.2 (4)
C3—C4—C9—C8	178.1 (4)	C11—C10—N5—C7	−96.1 (5)
N3—C2—N1—N2	0.8 (7)	C11—C10—N5—C12	85.7 (5)
N3—C1—N2—N1	−0.5 (6)	C13—C12—N5—C7	−92.9 (5)
C2—N1—N2—C1	−0.2 (7)	C13—C12—N5—C10	85.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1i	0.93	2.43	3.296 (7)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1i	0.93	2.43	3.296 (7)	155

Symmetry code: (i) .