1,3,5-Tris(pyridin-3-yl)-2,4-diaza­penta-1,4-diene

Quiroa-Montalván, C.M.; Aguirre, G.; Parra-Hake, M.

doi:10.1107/S1600536812005909

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o746

doi:10.1107/S1600536812005909

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1,3,5-Tris(pyridin-3-yl)-2,4-diazapenta-1,4-diene

Claudia M. Quiroa-Montalván,^a Gerardo Aguirre ^a and Miguel Parra-Hake ^a ^*

^aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500, Tijuana, B.C., Mexico
^*Correspondence e-mail: miguelhake@yahoo.com

(Received 5 December 2011; accepted 10 February 2012; online 17 February 2012)

In the solid state, the structure of the title compound, C₁₈H₁₅N₅, is stabilized by weak C—H⋯N interactions. Molecules are arranged in layers parallel to the bc plane forming an interesting supramolecular structure.

Related literature

For coordination polymers and supramolecular structures, see: Itoh et al. (2005 ); Albrechet (2001 ); Leininger et al. (2000 ). For potential applications in catalysis, gas storage, chirality, optics, magnetism, nanotechnology and luminescence, see: James (2003 ); Kitagawa et al. (2004 ); Masaoka et al. (2001 ); Rarig et al. (2002 ); Yaghi et al. (2003 ); Wang et al. (2009 ). For the preparation of this class of compound, see: Larter et al. (1998 ); Lozinskaya et al. (2003 ); Bessonov et al. (2005 ); Fernandes et al. (2007 ).

Experimental

Crystal data

C₁₈H₁₅N₅
M_r = 301.35
Monoclinic, P c
a = 5.7174 (11) Å
b = 8.0934 (10) Å
c = 16.972 (4) Å
β = 99.690 (18)°
V = 774.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.42 × 0.18 × 0.12 mm

Data collection

Bruker P4 diffractometer
3235 measured reflections
2874 independent reflections
1159 reflections with I > 2σ(I)
R_int = 0.061
3 standard reflections every 97 reflections intensity decay: 11.5%

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.135
S = 0.98
2874 reflections
209 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯N1ⁱ	0.93	2.74	3.552 (7)	146
C17—H17A⋯N3ⁱⁱ	0.93	2.66	3.456 (7)	144
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXS97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005909/rk2325sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005909/rk2325Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005909/rk2325Isup3.cml

checkCIF report

Comment top

The coordination chemistry of transition metals with polypyridyl ligands has progressed considerably during the last decades, and has been widely used for the construction of coordination polymers and other supramolecular structures (Itoh et al., 2005; Albrechet, 2001; Leininger et al., 2000). Such supramolecular architectures have attracted considerable attention due to potential applications in catalysis, gas storage, chirality, optical, magnetism, nanotechnology and luminescence (James, 2003; Kitagawa et al., 2004; Masaoka et al., 2001; Rarig et al., 2002; Yaghi et al., 2003; Wang et al., 2009). Also, there exists an increasing interest in the design and synthesis of luminescent compounds due to their potential applications as chemical sensors, photochemistry and electroluminescence. The development of chemosensors, is one of the main goals of supramolecular chemistry and an important area of vigorous investigation.

We are interested on the coordination chemistry of polypyridine ligands, which have fluorescent properties and could act as sensors for transition metals ions, and which can be used to construct different coordination polymers. Some of the ligands under study are: cis-(±)-2,4,5-tri(2-pyridyl)imidazoline, 2,4,6-tri(2-pyridyl)-1,3,5-triazinane, 2,4,5-tri(2-pyridyl)imidazole, trans-(±)-2,4,5-tri(4-pyridyl)imidazoline and 2,4,5-tri(4-pyridyl)imidazole.

As part of our ongoing research on the chemistry of polypyridine ligands, in our attempts to synthesize the ligand cis-(±)-3-(2,5-di(pyridin-3-yl)-4,5-dihydro-1H-imidazol-4-yl) pyridine, we have isolated the title compound, 1,3,5-tri(pyridin-3-yl)-2,4-diazapenta-1,4-diene. The 1,3,5-triaryl-2,4-diazapentadienes are known to form by the reaction of aromatic benzaldehydes with ammonia (Larter et al., 1998; Lozinskaya et al., 2003; Bessonov et al., 2005; Fernandes et al., 2007), which are analogues of the title compound. In the crystal structure adjacent networks are linked together via intermolecular hydrogen bond interactions (Table 1) (C18–H18···N1ⁱ (2.741Å), symmetry code: (i) x, 1-y, -1/2+z) in an array along the [0 0 1] and [C17–H17···N3ⁱⁱ (2.660Å), symmetry codes: (ii) x, 1+y, z] in an array along the [0 1 0]. The molecules are forming a layer structure parallel to the bc plane (Fig. 2).

Related literature top

For coordination polymers and supramolecular structures, see: Itoh et al. (2005); Albrechet (2001); Leininger et al. (2000). For potential applications in catalysis, gas storage, chirality, optics, magnetism, nanotechnology and luminescence, see: James (2003); Kitagawa et al. (2004); Masaoka et al. (2001); Rarig et al. (2002); Yaghi et al. (2003); Wang et al. (2009). For the preparation of this class of compound, see: Larter et al. (1998); Lozinskaya et al. (2003); Bessonov et al. (2005); Fernandes et al. (2007).

Experimental top

The synthesis of the title compound included reagent grade starting materials and solvents. A mixture of pyridine-3-carboxaldehyde (5 mL, 0.0531 mol) and ammonium hydroxide (15 mL, 0.3843 mol) was stirred at room temperature for 24 h. The mixture was filtered off and washed with water, then recrystallized by gas phase diffusion of diethyl ether into a concentrated solution of the product in dichloromethane, providing colorless crystals. Yield (3.5 g, 22%). M.p. = 388-390 K, (KBr) 3270, 3226, 3040, 2887, 1575, 1471, 1417, 1082, 1023, 868, 863, 808, 705 cm^-1. ¹H NMR (CDCl₃): 8.98 (d, J = 1.8 Hz, 2H), 8.79 (d, J = 1.8 Hz, 1H), 8.69 (dd, J = 4.8, 1.8 Hz, 2H), 8.66 (s, 2H), 8.59 (dd, J = 4.8, 2.1 Hz, 1H), 8.26 (ddd, J = 7.8, 1.8, 1.8 Hz, 2H), 7.87 (ddd, J = 8.2, 2.1, 1.8 Hz, 1H), 7.39 (dd, J = 7.8, 4.8 Hz, 2H), 7.33 (dd, J = 8.2, 4.8 Hz, 1H), 6.08 (s, 1H). ¹³C NMR (CDCl₃): 158.94, 152.21, 150.75, 149.53, 148.89, 136.61, 134.98, 134.83, 131.01, 123,73, 123.64, 90.28. EIMS (70 eV) m/e (int. rel.): M⁺ 301 (1%), M⁺-Py-CH═N 196 (100%), 168 (13%), 122 (3%), 92 (10%).

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXS97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of title compound with the atom numbering scheme. The displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The diagram showing the H-bonds. The molecules are forming an array along the [0 0 1] direction. H-bonds are indicated by broken lines.

1,3,5-Tris(pyridin-3-yl)-2,4-diazapenta-1,4-diene top

Crystal data top

C₁₈H₁₅N₅	F(000) = 316
M_r = 301.35	D_x = 1.293 Mg m⁻³
Monoclinic, Pc	Melting point = 388–390 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7174 (11) Å	Cell parameters from 33 reflections
b = 8.0934 (10) Å	θ = 4.7–11.6°
c = 16.972 (4) Å	µ = 0.08 mm⁻¹
β = 99.690 (18)°	T = 298 K
V = 774.1 (3) Å³	Neele, colourless
Z = 2	0.42 × 0.18 × 0.12 mm

Data collection top

Bruker P4 diffractometer	R_int = 0.061
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.4°
Graphite monochromator	h = −1→8
2θ/ω–scans	k = −1→11
3235 measured reflections	l = −23→23
2874 independent reflections	3 standard reflections every 97 reflections
1159 reflections with I > 2σ(I)	intensity decay: 11.5%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.070	w = 1/[σ²(F_o²) + (0.0352P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.135	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.17 e Å⁻³
2874 reflections	Δρ_min = −0.17 e Å⁻³
209 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.019 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map

Crystal data top

C₁₈H₁₅N₅	V = 774.1 (3) Å³
M_r = 301.35	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 5.7174 (11) Å	µ = 0.08 mm⁻¹
b = 8.0934 (10) Å	T = 298 K
c = 16.972 (4) Å	0.42 × 0.18 × 0.12 mm
β = 99.690 (18)°

Data collection top

Bruker P4 diffractometer	R_int = 0.061
3235 measured reflections	3 standard reflections every 97 reflections
2874 independent reflections	intensity decay: 11.5%
1159 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.070	2 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 0.98	Δρ_max = 0.17 e Å⁻³
2874 reflections	Δρ_min = −0.17 e Å⁻³
209 parameters	Absolute structure: Flack (1983)

Special details top

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

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

	x	y	z	U_iso*/U_eq
N3	0.3294 (7)	0.4546 (5)	0.0999 (2)	0.0434 (11)
C4	1.0463 (12)	0.2145 (8)	0.4651 (3)	0.0578 (18)
H4A	1.0947	0.1666	0.5150	0.069*
N2	0.6027 (8)	0.4678 (5)	0.2201 (2)	0.0408 (11)
C3	1.1993 (11)	0.2058 (7)	0.4105 (3)	0.0588 (18)
H3B	1.3474	0.1561	0.4235	0.071*
C7	0.5371 (9)	0.5446 (6)	0.1421 (3)	0.0413 (14)
H7A	0.6689	0.5367	0.1120	0.050*
C8	0.3369 (10)	0.4143 (6)	0.0281 (3)	0.0436 (14)
H8A	0.4684	0.4440	0.0057	0.052*
C16	0.2483 (11)	0.9366 (7)	0.1982 (3)	0.0486 (15)
H16A	0.1265	0.9714	0.2243	0.058*
N4	−0.0186 (9)	0.2211 (7)	−0.1527 (2)	0.0604 (15)
C2	1.1242 (10)	0.2739 (7)	0.3358 (3)	0.0481 (15)
H2B	1.2222	0.2715	0.2973	0.058*
C13	0.1481 (10)	0.2988 (7)	−0.1022 (3)	0.0497 (16)
H13A	0.2775	0.3410	−0.1223	0.060*
C14	0.4741 (10)	0.7230 (6)	0.1524 (3)	0.0402 (13)
C1	0.9022 (9)	0.3453 (7)	0.3190 (3)	0.0404 (14)
C12	−0.1994 (11)	0.1565 (7)	−0.1222 (3)	0.0587 (18)
H12A	−0.3174	0.1006	−0.1564	0.070*
C6	0.8136 (10)	0.4183 (7)	0.2402 (3)	0.0443 (15)
H6A	0.9172	0.4283	0.2037	0.053*
N1	0.8360 (8)	0.2859 (7)	0.4515 (2)	0.0638 (16)
C9	0.1421 (10)	0.3216 (7)	−0.0208 (3)	0.0411 (14)
C11	−0.2194 (10)	0.1688 (7)	−0.0427 (3)	0.0555 (17)
H11A	−0.3465	0.1201	−0.0238	0.067*
C10	−0.0493 (10)	0.2540 (7)	0.0083 (3)	0.0476 (15)
H10A	−0.0625	0.2662	0.0619	0.057*
C15	0.2938 (10)	0.7702 (7)	0.1923 (3)	0.0482 (15)
H15A	0.2052	0.6919	0.2145	0.058*
C18	0.5982 (12)	0.8483 (7)	0.1210 (3)	0.0558 (16)
H18A	0.7196	0.8174	0.0938	0.067*
C5	0.7697 (10)	0.3477 (7)	0.3793 (3)	0.0495 (15)
H5A	0.6207	0.3969	0.3683	0.059*
C17	0.3808 (11)	1.0503 (8)	0.1661 (3)	0.0627 (18)
H17A	0.3474	1.1617	0.1718	0.075*
N5	0.5548 (11)	1.0099 (6)	0.1272 (3)	0.0731 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.051 (3)	0.040 (3)	0.039 (2)	0.001 (3)	0.008 (2)	−0.001 (2)
C4	0.063 (5)	0.062 (5)	0.042 (3)	−0.010 (4)	−0.008 (3)	0.019 (3)
N2	0.050 (3)	0.039 (3)	0.033 (2)	0.000 (3)	0.005 (2)	0.001 (2)
C3	0.046 (4)	0.055 (4)	0.069 (4)	0.001 (4)	−0.008 (3)	0.007 (3)
C7	0.043 (4)	0.044 (3)	0.038 (3)	0.002 (3)	0.010 (3)	0.002 (3)
C8	0.049 (4)	0.041 (3)	0.041 (3)	−0.001 (3)	0.010 (3)	0.003 (3)
C16	0.060 (4)	0.041 (4)	0.049 (3)	0.002 (4)	0.019 (3)	−0.006 (3)
N4	0.061 (4)	0.073 (4)	0.044 (3)	0.011 (4)	0.000 (3)	−0.013 (3)
C2	0.042 (4)	0.057 (4)	0.046 (3)	0.002 (4)	0.010 (3)	−0.006 (3)
C13	0.050 (4)	0.060 (4)	0.038 (3)	0.014 (4)	0.006 (3)	0.000 (3)
C14	0.048 (4)	0.040 (3)	0.032 (3)	0.006 (4)	0.004 (3)	0.004 (3)
C1	0.039 (4)	0.043 (3)	0.037 (3)	−0.003 (3)	0.002 (3)	0.001 (3)
C12	0.059 (5)	0.054 (4)	0.057 (4)	0.006 (4)	−0.006 (3)	−0.016 (3)
C6	0.050 (4)	0.042 (3)	0.043 (3)	0.002 (3)	0.012 (3)	−0.005 (3)
N1	0.050 (4)	0.089 (4)	0.049 (3)	−0.004 (4)	−0.001 (3)	0.015 (3)
C9	0.048 (4)	0.037 (3)	0.038 (3)	0.009 (3)	0.007 (3)	−0.001 (3)
C11	0.051 (4)	0.057 (4)	0.058 (4)	0.002 (4)	0.009 (3)	−0.009 (3)
C10	0.057 (4)	0.047 (4)	0.039 (3)	0.008 (4)	0.007 (3)	−0.003 (3)
C15	0.056 (4)	0.048 (4)	0.042 (3)	−0.017 (4)	0.014 (3)	−0.002 (3)
C18	0.058 (4)	0.054 (4)	0.061 (3)	−0.001 (4)	0.028 (3)	−0.005 (3)
C5	0.041 (4)	0.059 (4)	0.048 (3)	0.000 (4)	0.007 (3)	0.004 (3)
C17	0.089 (6)	0.043 (4)	0.061 (3)	−0.001 (4)	0.026 (4)	−0.002 (3)
N5	0.101 (5)	0.050 (4)	0.080 (3)	−0.001 (4)	0.051 (4)	0.010 (3)

Geometric parameters (Å, º) top

N3—C8	1.269 (5)	C13—C9	1.401 (6)
N3—C7	1.472 (6)	C13—H13A	0.9300
C4—N1	1.319 (7)	C14—C15	1.378 (7)
C4—C3	1.380 (8)	C14—C18	1.394 (7)
C4—H4A	0.9300	C1—C5	1.372 (7)
N2—C6	1.262 (6)	C1—C6	1.473 (7)
N2—C7	1.454 (6)	C12—C11	1.376 (7)
C3—C2	1.383 (7)	C12—H12A	0.9300
C3—H3B	0.9300	C6—H6A	0.9300
C7—C14	1.506 (6)	N1—C5	1.319 (6)
C7—H7A	0.9800	C9—C10	1.387 (7)
C8—C9	1.476 (7)	C11—C10	1.374 (7)
C8—H8A	0.9300	C11—H11A	0.9300
C16—C17	1.363 (7)	C10—H10A	0.9300
C16—C15	1.378 (7)	C15—H15A	0.9300
C16—H16A	0.9300	C18—N5	1.339 (7)
N4—C13	1.327 (7)	C18—H18A	0.9300
N4—C12	1.338 (8)	C5—H5A	0.9300
C2—C1	1.380 (7)	C17—N5	1.324 (7)
C2—H2B	0.9300	C17—H17A	0.9300

C8—N3—C7	116.0 (4)	C5—C1—C6	121.5 (5)
N1—C4—C3	124.5 (5)	C2—C1—C6	121.3 (5)
N1—C4—H4A	117.7	N4—C12—C11	123.2 (6)
C3—C4—H4A	117.7	N4—C12—H12A	118.4
C6—N2—C7	118.0 (4)	C11—C12—H12A	118.4
C4—C3—C2	117.5 (6)	N2—C6—C1	122.6 (5)
C4—C3—H3B	121.2	N2—C6—H6A	118.7
C2—C3—H3B	121.2	C1—C6—H6A	118.7
N2—C7—N3	107.1 (4)	C5—N1—C4	116.1 (5)
N2—C7—C14	109.5 (4)	C10—C9—C13	116.8 (5)
N3—C7—C14	110.0 (4)	C10—C9—C8	124.5 (5)
N2—C7—H7A	110.1	C13—C9—C8	118.7 (5)
N3—C7—H7A	110.1	C12—C11—C10	119.2 (6)
C14—C7—H7A	110.1	C12—C11—H11A	120.4
N3—C8—C9	121.7 (5)	C10—C11—H11A	120.4
N3—C8—H8A	119.1	C11—C10—C9	119.4 (5)
C9—C8—H8A	119.1	C11—C10—H10A	120.3
C17—C16—C15	120.4 (6)	C9—C10—H10A	120.3
C17—C16—H16A	119.8	C16—C15—C14	118.2 (5)
C15—C16—H16A	119.8	C16—C15—H15A	120.9
C13—N4—C12	117.0 (5)	C14—C15—H15A	120.9
C1—C2—C3	119.2 (5)	N5—C18—C14	124.5 (6)
C1—C2—H2B	120.4	N5—C18—H18A	117.7
C3—C2—H2B	120.4	C14—C18—H18A	117.7
N4—C13—C9	124.4 (5)	N1—C5—C1	125.4 (6)
N4—C13—H13A	117.8	N1—C5—H5A	117.3
C9—C13—H13A	117.8	C1—C5—H5A	117.3
C15—C14—C18	117.2 (5)	N5—C17—C16	123.2 (6)
C15—C14—C7	122.4 (5)	N5—C17—H17A	118.4
C18—C14—C7	120.3 (5)	C16—C17—H17A	118.4
C5—C1—C2	117.2 (5)	C17—N5—C18	116.4 (6)

N1—C4—C3—C2	−1.4 (9)	N4—C13—C9—C10	1.6 (8)
C6—N2—C7—N3	125.7 (5)	N4—C13—C9—C8	−178.4 (5)
C6—N2—C7—C14	−115.1 (5)	N3—C8—C9—C10	−7.8 (8)
C8—N3—C7—N2	−133.5 (5)	N3—C8—C9—C13	172.3 (5)
C8—N3—C7—C14	107.6 (5)	N4—C12—C11—C10	1.3 (9)
C7—N3—C8—C9	179.1 (4)	C12—C11—C10—C9	−1.8 (8)
C4—C3—C2—C1	−0.5 (8)	C13—C9—C10—C11	0.4 (7)
C12—N4—C13—C9	−2.2 (8)	C8—C9—C10—C11	−179.5 (5)
N2—C7—C14—C15	−59.2 (6)	C17—C16—C15—C14	−0.7 (8)
N3—C7—C14—C15	58.3 (6)	C18—C14—C15—C16	0.1 (7)
N2—C7—C14—C18	121.2 (5)	C7—C14—C15—C16	−179.6 (5)
N3—C7—C14—C18	−121.4 (5)	C15—C14—C18—N5	0.3 (9)
C3—C2—C1—C5	1.5 (8)	C7—C14—C18—N5	180.0 (6)
C3—C2—C1—C6	−179.6 (5)	C4—N1—C5—C1	−1.1 (9)
C13—N4—C12—C11	0.6 (9)	C2—C1—C5—N1	−0.7 (9)
C7—N2—C6—C1	177.3 (4)	C6—C1—C5—N1	−179.7 (6)
C5—C1—C6—N2	−9.1 (8)	C15—C16—C17—N5	0.9 (9)
C2—C1—C6—N2	171.9 (6)	C16—C17—N5—C18	−0.5 (9)
C3—C4—N1—C5	2.2 (9)	C14—C18—N5—C17	−0.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N1ⁱ	0.93	2.74	3.552 (7)	146
C17—H17A···N3ⁱⁱ	0.93	2.66	3.456 (7)	144

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₅
M_r	301.35
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	5.7174 (11), 8.0934 (10), 16.972 (4)
β (°)	99.690 (18)
V (Å³)	774.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.18 × 0.12

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3235, 2874, 1159
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.135, 0.98
No. of reflections	2874
No. of parameters	209
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17
Absolute structure	Flack (1983)

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N1ⁱ	0.93	2.74	3.552 (7)	146.2
C17—H17A···N3ⁱⁱ	0.93	2.66	3.456 (7)	144.0

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z.

Acknowledgements

This work was supported by Dirección General de Educación Superior Tecnológica (DGEST) (grant No. 2785.09-P). Support from Consejo Nacional de Ciencia y Tecnología (CONACyT) in the form of a graduate scholarship for CMQM is gratefully acknowledged.

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