N-(2-Hydroxy­ethyl)-2-[3-(p-tol­yl)triazen-1-yl]benzamide

Rocha-Alonzo, F.; Aguirre, G.; Parra-Hake, M.

doi:10.1107/S1600536809011908

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o990-o991

doi:10.1107/S1600536809011908

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N-(2-Hydroxyethyl)-2-[3-(p-tolyl)triazen-1-yl]benzamide

Fernando Rocha-Alonzo,^a Gerardo Aguirre ^a ^* and Miguel Parra-Hake ^a

^aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500, Tijuana, BC, Mexico
^*Correspondence e-mail: gaguirre@tectijuana.mx

(Received 9 March 2009; accepted 31 March 2009; online 8 April 2009)

In the solid state, the structure of the title compound, C₁₆H₁₈N₄O₂, is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds. These hydrogen bonds arrange the molecules into a double-layer supramolecular structure. The molecular conformation is is consolidated by an intramolecular N—H⋯N hydrogen bond. The dihedral angle between the aromatic rings is 8.01 (10)°

Related literature

For the synthesis of new ligands to stabilize dinuclear complexes and control their reactivity, see: Das et al. (2008 ); Estevan et al. (2006 ); Jie et al. (2007 ); Müller & Vogt (2007 ); Schilling et al. (2008 ). For the synthesis of 1,3-bis(aryl)triazenes as precursors for triazenido ligands bearing Lewis basic ortho substituents such as ester, methoxy and methylmercapto groups, see: Nuricumbo-Escobar et al.(2007 ); Ríos-Moreno et al. (2003 ); Rodríguez et al. (1999 ); Tejel et al. (2004 ). The starting material 2-[4,5-dihydro-1,3-oxazol-2-yl]aniline was synthesized by a modification of the literature method of Gómez et al. (2005 ). For bond-length data, see: Allen et al. (1987 ); Orpen et al. (1989 ).

Experimental

Crystal data

C₁₆H₁₈N₄O₂
M_r = 298.34
Monoclinic, P 2₁ /c
a = 16.846 (2) Å
b = 12.2053 (17) Å
c = 7.4302 (11) Å
β = 93.212 (13)°
V = 1525.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.22 × 0.14 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
4153 measured reflections
3067 independent reflections
1778 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections every 97 reflections intensity decay: 2.8%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.188
S = 1.04
3067 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N1	0.86	2.05	2.696 (3)	132
O2—H2B⋯O1ⁱ	0.82	1.92	2.729 (2)	169
N3—H3A⋯O2ⁱⁱ	0.86	2.00	2.851 (2)	170
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -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: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011908/kp2210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011908/kp2210Isup2.hkl

checkCIF report

Comment top

The synthesis of alternative ligands to stabilize dinuclear complexes and control their reactivity is an area of great importance in coordination and organometallic chemistry (for recent literature see: Das et al., 2008; Estevan et al., 2006; Jie et al., 2007; Müller & Vogt, 2007; Schilling et al., 2008). In this context, we have focused our attention to the synthesis of 1,3-bis(aryl)triazenes as precursors for triazenido ligands bearing Lewis basic ortho substituents such as ester, methoxy and methylmercapto groups (Nuricumbo-Escobar et al., 2007; Ríos-Moreno et al., 2003; Rodríguez et al., 1999; Tejel et al., 2004); it has been found that the nature of the substituent produces a dramatic impact on their coordination chemistry and reactivity. As part of our ongoing research, we have synthesized the title compound (I, Fig. 1) using the diazonium salt N-coupling methodology.

The molecular structure of (I) shows the characteristic trans stereochemistry about N═N of the diazoamino group of free triazenes. The N1═N2 bond [1.264 (3) Å] is longer than the typical value for N═N bond (1.222 Å), whereas the N2—N3 bond [1.320 (3) Å] is shorter than typical value for a Nsp³—Nsp² single bond (1.420 Å) (Allen et al., 1987). In addition, the C7—N3 bond [1.395 (3) Å] is shorter than the characteristic C_aryl—NH single bonds for secondary aromatic amines (1.419 Å) (Orpen, et al., 1989). An intramolecular N1—H···N4 hydrogen bond is observed (Fig. 1 and Table 1).

In the crystal structure, adjacent units are arranged into a two-dimensional network along the (100) plane via intermolecular N— H···O and O—H···O hydrogen bond interactions (Fig. 2 and Table 1). These layers are linked together via intermolecular N—H···O and O—H···O hydrogen bonds forming a zig-zag bilayered array along the [001] direction (Fig. 3).

Related literature top

The synthesis of alternative ligands to stabilize dinuclear complexes and control their reactivity is an area of great importance in coordination and organometallic chemistry, see: Das et al. (2008); Estevan et al. (2006); Jie et al. (2007); Müller & Vogt (2007); Schilling et al. (2008). For the synthesis of 1,3-bis(aryl)triazenes as precursors for triazenido ligands bearing Lewis basic ortho substituents such as ester, methoxy and methylmercapto groups, see: Nuricumbo-Escobar et al.(2007); Ríos-Moreno et al. (2003); Rodríguez et al. (1999); Tejel et al. (2004). The starting material 2-[4,5-dihydro-1,3-oxazol-2-yl]aniline was synthesized by a modification of the literature method of Gómez et al. (2005). For bond-length data, see: Allen et al. (1987); Orpen et al. (1989).

Experimental top

The synthesis of the title compound included reagents and solvents of reagent grade, which were used without further purification. As a starting material we synthesized 2-[4,5-dihydro-1,3-oxazol-2-yl]aniline by a modification of the Gómez and coworkers methodology (Gómez et al., 2005). 2-[4,5-Dihydro-1,3-oxazol-2-yl]aniline (1.00 g, 6.17 mmol) was dissolved in aqueous HCl 2 M (9.25 ml, 18.50 mmol) and cooled to 268 K. A sodium nitrite solution (0.51 g, 7.40 mmol) in water (6 ml) was slowly added with continuous stirring. A solution of p-toluidine (0.66 g, 6.17 mmol) in methanol (10 ml) was added slowly to the reaction mixture, and stirred for 30 m at 268 K. The resulting mixture was neutralised with a saturated aqueous solution of NaHCO₃. A crude yellow-orange was separated by filtration and washed with small portions of water. The product was purified by flash chromatography on neutral alumina (hexane/ethyl acetate, 1:9), and recrystallized from an ethyl acetate/hexane mixture (9 : 1). Orange bar-shaped crystals of (I), suitable for X-ray analysis, were obtained by slow evaporation of the solvent mixture. Yield 47% (0.87 g, 2.90 mmol), based on 2-[4,5-dihydro-1,3-oxazol-2-yl]aniline; m.p., 111–113 °C. IR (KBr pellet, cm^-1), 3278, 3233, 1625, 1538, 1269.¹H NMR [(CD₃)₂CO, 200 MHz] δ 12.89 (s), 8.10 (s), 7.93–7.02 (m, 8H), 4.10 (s), 3.74 (dd J = 5.4, 11.0 Hz, 2H), 3.54 (dd, J = 5.4, 11.0 Hz, 2H), 2.35 (s, 3H).¹³C NMR [(C D₃)₂CO, 50 MHz] δ 135.4, 133.0, 130.1, 128.4, 121.7,114.9, 61.2, 43.2, 21.0. Anal. Calcd. for C₁₆H₁₈N₄O₂: C, 64.41; H, 6.08;N, 18.78%. Found C, 64.11; H, 6.44; N, 18.93%. HRESIMS Calcd. for [M+H]⁺299.1503. Found 299.1519.

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: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title compound (I) with displacement ellipsoids drawn at the 30% probability level. Intramolecular H-bond is indicated by dashed lines.
	Fig. 2. Packing of I showing the H-bonds. The molecules are forming a two dimensional network in the (100) plane. H-bonds are indicated by dashed lines.
	Fig. 3. Packing of I showing the bilayer. The molecules are forming a zig-zag array along the [001] direction.

N-(2-Hydroxyethyl)-2-[3-(p-tolyl)triazen-1-yl]benzamide top

Crystal data top

C₁₆H₁₈N₄O₂	F(000) = 632
M_r = 298.34	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 76 reflections
a = 16.846 (2) Å	θ = 4.7–12.0°
b = 12.2053 (17) Å	µ = 0.09 mm⁻¹
c = 7.4302 (11) Å	T = 298 K
β = 93.212 (13)°	Neele, yellow
V = 1525.3 (4) Å³	0.40 × 0.22 × 0.14 mm
Z = 4

Data collection top

Bruker P4 diffractometer	R_int = 0.044
Radiation source: fine-focus sealed tube	θ_max = 26.3°, θ_min = 2.1°
Graphite monochromator	h = −20→20
2θ/ω scans	k = −15→1
4153 measured reflections	l = −9→1
3067 independent reflections	3 standard reflections every 97 reflections
1778 reflections with I > 2σ(I)	intensity decay: 2.8%

Refinement top

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.1035P)² + 0.0651P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3067 reflections	Δρ_max = 0.57 e Å⁻³
201 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (3)

Crystal data top

C₁₆H₁₈N₄O₂	V = 1525.3 (4) Å³
M_r = 298.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.846 (2) Å	µ = 0.09 mm⁻¹
b = 12.2053 (17) Å	T = 298 K
c = 7.4302 (11) Å	0.40 × 0.22 × 0.14 mm
β = 93.212 (13)°

Data collection top

Bruker P4 diffractometer	R_int = 0.044
4153 measured reflections	3 standard reflections every 97 reflections
3067 independent reflections	intensity decay: 2.8%
1778 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.04	Δρ_max = 0.57 e Å⁻³
3067 reflections	Δρ_min = −0.22 e Å⁻³
201 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.69940 (11)	0.33793 (15)	−0.0017 (3)	0.0484 (5)
N2	0.76320 (11)	0.39013 (16)	0.0332 (3)	0.0481 (5)
N4	0.54570 (10)	0.30472 (15)	−0.1084 (3)	0.0456 (5)
H4A	0.5790	0.3480	−0.0525	0.055*
O1	0.51316 (10)	0.13062 (14)	−0.1750 (2)	0.0574 (5)
O2	0.39653 (10)	0.39859 (16)	0.0593 (3)	0.0651 (6)
H2B	0.4341	0.3834	0.1299	0.098*
N3	0.75322 (11)	0.49670 (16)	0.0124 (3)	0.0521 (6)
H3A	0.7066	0.5219	−0.0175	0.063*
C1	0.70741 (13)	0.22274 (19)	0.0146 (3)	0.0434 (6)
C2	0.64042 (13)	0.15801 (18)	−0.0313 (3)	0.0424 (6)
C3	0.64717 (15)	0.0445 (2)	−0.0087 (4)	0.0550 (7)
H3B	0.6029	0.0006	−0.0346	0.066*
C4	0.71719 (17)	−0.0036 (2)	0.0504 (4)	0.0646 (8)
H4B	0.7200	−0.0792	0.0651	0.078*
C5	0.78345 (15)	0.0601 (2)	0.0881 (4)	0.0654 (8)
H5A	0.8317	0.0275	0.1237	0.078*
C6	0.77816 (14)	0.1716 (2)	0.0729 (4)	0.0577 (7)
H6A	0.8228	0.2141	0.1022	0.069*
C7	0.81680 (13)	0.56925 (19)	0.0379 (3)	0.0472 (6)
C8	0.80588 (14)	0.6767 (2)	−0.0132 (4)	0.0552 (7)
H8A	0.7569	0.6993	−0.0642	0.066*
C9	0.86733 (16)	0.7513 (2)	0.0109 (4)	0.0608 (7)
H9A	0.8588	0.8240	−0.0227	0.073*
C10	0.94103 (16)	0.7200 (3)	0.0839 (4)	0.0622 (8)
C11	0.95105 (16)	0.6126 (3)	0.1297 (4)	0.0682 (8)
H11A	1.0006	0.5896	0.1771	0.082*
C12	0.89054 (14)	0.5364 (2)	0.1086 (4)	0.0608 (7)
H12A	0.8994	0.4637	0.1416	0.073*
C13	0.56158 (13)	0.19811 (19)	−0.1101 (3)	0.0420 (5)
C14	0.47468 (13)	0.3509 (2)	−0.1968 (3)	0.0495 (6)
H14A	0.4671	0.3186	−0.3157	0.059*
H14B	0.4829	0.4289	−0.2126	0.059*
C15	0.40087 (15)	0.3347 (2)	−0.0995 (4)	0.0617 (8)
H15A	0.3555	0.3523	−0.1806	0.074*
H15B	0.3968	0.2580	−0.0676	0.074*
C16	1.0073 (2)	0.8027 (3)	0.1157 (5)	0.0921 (11)
H16A	1.0569	0.7649	0.1374	0.138*
H16B	0.9968	0.8470	0.2184	0.138*
H16C	1.0101	0.8486	0.0113	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0424 (10)	0.0407 (11)	0.0617 (13)	−0.0019 (9)	0.0007 (9)	−0.0026 (9)
N2	0.0432 (11)	0.0418 (11)	0.0585 (13)	−0.0002 (9)	−0.0026 (9)	−0.0039 (9)
N4	0.0368 (10)	0.0412 (11)	0.0581 (13)	0.0021 (8)	−0.0039 (9)	−0.0023 (9)
O1	0.0554 (10)	0.0464 (10)	0.0678 (12)	−0.0062 (8)	−0.0189 (9)	−0.0037 (8)
O2	0.0477 (10)	0.0882 (14)	0.0579 (12)	0.0226 (9)	−0.0101 (8)	−0.0129 (10)
N3	0.0373 (10)	0.0382 (11)	0.0796 (15)	0.0020 (8)	−0.0072 (10)	−0.0020 (10)
C1	0.0409 (12)	0.0430 (13)	0.0461 (13)	0.0018 (10)	0.0015 (10)	0.0002 (10)
C2	0.0438 (12)	0.0405 (13)	0.0428 (13)	0.0027 (10)	0.0001 (10)	−0.0001 (10)
C3	0.0560 (15)	0.0425 (14)	0.0654 (17)	−0.0017 (11)	−0.0071 (12)	−0.0009 (12)
C4	0.0697 (18)	0.0407 (14)	0.082 (2)	0.0094 (13)	−0.0100 (15)	0.0012 (14)
C5	0.0509 (15)	0.0536 (16)	0.090 (2)	0.0143 (12)	−0.0097 (14)	0.0021 (15)
C6	0.0426 (13)	0.0525 (16)	0.0771 (19)	0.0020 (11)	−0.0053 (12)	0.0019 (13)
C7	0.0385 (12)	0.0428 (13)	0.0603 (15)	−0.0017 (10)	0.0020 (11)	−0.0070 (11)
C8	0.0420 (13)	0.0508 (15)	0.0726 (18)	0.0000 (11)	0.0029 (12)	0.0010 (13)
C9	0.0587 (16)	0.0510 (16)	0.0737 (18)	−0.0109 (12)	0.0113 (14)	−0.0017 (13)
C10	0.0525 (15)	0.0679 (18)	0.0669 (18)	−0.0196 (13)	0.0083 (13)	−0.0146 (15)
C11	0.0412 (14)	0.078 (2)	0.084 (2)	−0.0023 (13)	−0.0095 (13)	−0.0153 (17)
C12	0.0469 (14)	0.0481 (14)	0.086 (2)	0.0037 (12)	−0.0122 (13)	−0.0078 (14)
C13	0.0422 (12)	0.0436 (13)	0.0398 (12)	−0.0002 (10)	−0.0004 (10)	0.0004 (10)
C14	0.0487 (14)	0.0481 (14)	0.0508 (15)	0.0031 (11)	−0.0051 (11)	0.0011 (11)
C15	0.0456 (14)	0.0737 (19)	0.0643 (18)	0.0056 (13)	−0.0097 (12)	0.0006 (15)
C16	0.073 (2)	0.103 (3)	0.100 (3)	−0.043 (2)	0.0043 (18)	−0.016 (2)

Geometric parameters (Å, º) top

N1—N2	1.264 (3)	C6—H6A	0.9300
N1—C1	1.417 (3)	C7—C8	1.375 (4)
N2—N3	1.319 (3)	C7—C12	1.381 (3)
N4—C13	1.329 (3)	C8—C9	1.383 (3)
N4—C14	1.447 (3)	C8—H8A	0.9300
N4—H4A	0.8600	C9—C10	1.381 (4)
O1—C13	1.238 (3)	C9—H9A	0.9300
O2—C15	1.420 (3)	C10—C11	1.363 (4)
O2—H2B	0.8200	C10—C16	1.513 (4)
N3—C7	1.395 (3)	C11—C12	1.382 (4)
N3—H3A	0.8600	C11—H11A	0.9300
C1—C6	1.393 (3)	C12—H12A	0.9300
C1—C2	1.404 (3)	C14—C15	1.486 (4)
C2—C3	1.400 (3)	C14—H14A	0.9700
C2—C13	1.503 (3)	C14—H14B	0.9700
C3—C4	1.368 (3)	C15—H15A	0.9700
C3—H3B	0.9300	C15—H15B	0.9700
C4—C5	1.376 (4)	C16—H16A	0.9600
C4—H4B	0.9300	C16—H16B	0.9600
C5—C6	1.367 (4)	C16—H16C	0.9600
C5—H5A	0.9300

N2—N1—C1	114.01 (19)	C10—C9—C8	121.2 (3)
N1—N2—N3	111.82 (19)	C10—C9—H9A	119.4
C13—N4—C14	122.64 (19)	C8—C9—H9A	119.4
C13—N4—H4A	118.7	C11—C10—C9	117.4 (2)
C14—N4—H4A	118.7	C11—C10—C16	121.5 (3)
C15—O2—H2B	109.5	C9—C10—C16	121.0 (3)
N2—N3—C7	121.21 (19)	C10—C11—C12	122.6 (3)
N2—N3—H3A	119.4	C10—C11—H11A	118.7
C7—N3—H3A	119.4	C12—C11—H11A	118.7
C6—C1—C2	119.0 (2)	C7—C12—C11	119.3 (3)
C6—C1—N1	123.2 (2)	C7—C12—H12A	120.3
C2—C1—N1	117.79 (19)	C11—C12—H12A	120.3
C3—C2—C1	118.0 (2)	O1—C13—N4	121.8 (2)
C3—C2—C13	115.7 (2)	O1—C13—C2	118.9 (2)
C1—C2—C13	126.3 (2)	N4—C13—C2	119.3 (2)
C4—C3—C2	121.7 (2)	N4—C14—C15	114.9 (2)
C4—C3—H3B	119.1	N4—C14—H14A	108.5
C2—C3—H3B	119.1	C15—C14—H14A	108.5
C3—C4—C5	119.9 (3)	N4—C14—H14B	108.5
C3—C4—H4B	120.1	C15—C14—H14B	108.5
C5—C4—H4B	120.1	H14A—C14—H14B	107.5
C6—C5—C4	119.8 (2)	O2—C15—C14	114.5 (2)
C6—C5—H5A	120.1	O2—C15—H15A	108.6
C4—C5—H5A	120.1	C14—C15—H15A	108.6
C5—C6—C1	121.5 (2)	O2—C15—H15B	108.6
C5—C6—H6A	119.3	C14—C15—H15B	108.6
C1—C6—H6A	119.3	H15A—C15—H15B	107.6
C8—C7—C12	119.1 (2)	C10—C16—H16A	109.5
C8—C7—N3	118.6 (2)	C10—C16—H16B	109.5
C12—C7—N3	122.3 (2)	H16A—C16—H16B	109.5
C7—C8—C9	120.3 (2)	C10—C16—H16C	109.5
C7—C8—H8A	119.8	H16A—C16—H16C	109.5
C9—C8—H8A	119.8	H16B—C16—H16C	109.5

C1—N1—N2—N3	178.6 (2)	N3—C7—C8—C9	179.6 (2)
N1—N2—N3—C7	−177.7 (2)	C7—C8—C9—C10	0.9 (4)
N2—N1—C1—C6	3.2 (3)	C8—C9—C10—C11	0.6 (4)
N2—N1—C1—C2	−176.6 (2)	C8—C9—C10—C16	−178.0 (3)
C6—C1—C2—C3	2.7 (3)	C9—C10—C11—C12	−1.2 (4)
N1—C1—C2—C3	−177.6 (2)	C16—C10—C11—C12	177.4 (3)
C6—C1—C2—C13	−174.8 (2)	C8—C7—C12—C11	1.3 (4)
N1—C1—C2—C13	5.0 (3)	N3—C7—C12—C11	179.8 (2)
C1—C2—C3—C4	−2.1 (4)	C10—C11—C12—C7	0.2 (5)
C13—C2—C3—C4	175.6 (2)	C14—N4—C13—O1	−6.1 (4)
C2—C3—C4—C5	−0.5 (4)	C14—N4—C13—C2	173.9 (2)
C3—C4—C5—C6	2.5 (5)	C3—C2—C13—O1	−11.0 (3)
C4—C5—C6—C1	−2.0 (5)	C1—C2—C13—O1	166.5 (2)
C2—C1—C6—C5	−0.7 (4)	C3—C2—C13—N4	169.0 (2)
N1—C1—C6—C5	179.5 (3)	C1—C2—C13—N4	−13.5 (3)
N2—N3—C7—C8	169.7 (2)	C13—N4—C14—C15	76.5 (3)
N2—N3—C7—C12	−8.8 (4)	N4—C14—C15—O2	71.8 (3)
C12—C7—C8—C9	−1.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N1	0.86	2.05	2.696 (3)	132
O2—H2B···O1ⁱ	0.82	1.92	2.729 (2)	169
N3—H3A···O2ⁱⁱ	0.86	2.00	2.851 (2)	170

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₄O₂
M_r	298.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.846 (2), 12.2053 (17), 7.4302 (11)
β (°)	93.212 (13)
V (Å³)	1525.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.22 × 0.14

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4153, 3067, 1778
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.188, 1.04
No. of reflections	3067
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.22

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N1	0.86	2.05	2.696 (3)	131.7
O2—H2B···O1ⁱ	0.82	1.92	2.729 (2)	168.6
N3—H3A···O2ⁱⁱ	0.86	2.00	2.851 (2)	170.4

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

Acknowledgements

We gratefully acknowledge support for this project by Consejo Nacional de Ciencia y Tecnología (CONACyT grant 60467), Consejo del Sistema Nacional de EducaciónTecnológica (COSNET grant 486–02-P) and a graduate scholarship from CONACyT for F. Rocha-Alonzo. The authors are indebted to Adrián Ochoa Terán and Ignacio Rivero Espejel for their support in this work. We acknowledge Universidad Autónoma de Nuevo-León (Monterrey, México) for diffractometer time.

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