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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page o1280
doi:10.1107/S1600536813019545

N,N-Di­ethyl-4-[(E)-(pyridin-3-yl)diazen­yl]aniline

Sergiu Draguta,a* Evgeniya Leonova,b Maria Fokina,c Igor Denisyukc and Tatiana V. Timofeevab

aD. Ghitu Institute of Electronic Engineering and Nanotechnologies, 3/3 Academy Street, MD-2028, Chisinau, Republic of Moldova, bDepartment of Chemistry and Biology, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA, and cSaint-Petersburg National Research University of Information Technologies, Mechanics and Optics, Kronverkskiy Prospekt 49, 197101 Saint Petersburg, Russian Federation
*Correspondence e-mail: sergiudraguta@gmail.com

(Received 30 June 2013; accepted 15 July 2013; online 20 July 2013)

The mol­ecule of the title compound, C15H18N4, adopts a trans conformation with respect to the diazo N=N bond. The dihedral angle between the benzene and pyridine rings in the mol­ecule is 8.03 (5)°. In the crystal, a weak C—H⋯π inter­action arranges the mol­ecules into a corrugated ribbon, with an anti­parallel orientation of neighboring mol­ecules propagating in the [100] direction.

Related literature

For details of the synthesis, see: Peor et al. (2008[Peor, N., Sfez, R. & Yitzchaik, Sh. (2008). J. Am. Chem. Soc. 130, 4158-4165.]). For nonlinear optical properties of stilbene derivatives, see: Forrest et al. (1996[Forrest, S., Burrows, P., Stroustrup, A., Strickland, D. & Ban, V. (1996). Appl. Phys. Lett. 68, 1326-1332.]). For the comparision of nonlinear optical properties of stilbene and diazo derivatives, see: Chemla & Zyss (1987[Chemla, D. S. & Zyss, J. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 1, pp. 232-277. New York: Academic Press.]); Morley (1995[Morley, J. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 731-738.]). For second-harmonic generation in the P212121 space group, see: Rivera et al. (2006[Rivera, J. M., Reyes, H., Cortés, A., Santillan, R., Lacroix, P. G., Lepetit, C., Nakatani, K. & Farfán, N. (2006). Chem. Mater. 18, 1174-1179.]). For the distribution of endocyclic angles in pyridine derivatives, see: Draguta et al. (2012[Draguta, S., Khrustalev, V. N., Fonari, M. S., Antipin, M. Y. & Timofeeva, T. V. (2012). Acta Cryst. E68, o3353.]).

[Scheme 1]

Experimental

Crystal data

  • C15H18N4

  • Mr = 254.33

  • Orthorhombic, P 21 21 21

  • a = 7.4332 (7) Å

  • b = 9.1093 (8) Å

  • c = 20.1946 (19) Å

  • V = 1367.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.985

  • 16318 measured reflections

  • 4195 independent reflections

  • 4012 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.113

  • S = 1.00

  • 4195 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of C6–C11 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯Cgi 0.95 2.60 3.483 (2) 158
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019545/cv5422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019545/cv5422Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019545/cv5422Isup3.cml

checkCIF report


Comment top

This molecule as a donor-acceptor substituted stilbene-like derivative supposed to show nonlinear optical response (Forrest et al., 1996). According to experimental data, such a response for molecules with a CH═CH bridge is higher than for molecules with an N═N bridge (Chemla & Zyss, 1987). On the other hand, theoretical calculations have predicted that azobenzenes can exhibit larger hyperpolarizabilities than stilbene analogues (Morley, 1995). The title compound has a noncentrosymmetric packing and therefore crystals of this material might demonstrate SHG. Usually because of antiparallel dipole positions in the P212121 space group the SHG is weak or undetectable. However there are some exceptions from such regularity, for instance, for molecules of coordination compounds described with two dipole moments (Rivera et al., 2006) SHG was experimentally observed. We tried to experimentally evaluate SHG of this crystal. SHG experiment on a single crystal was done; laser power was increased step by step without appearance of visible SHG. At the maximal laser power crystals were melted under femtosecond laser beam. The absence of SHG for tested sample is not surprising since orientation of neighboring molecules in crystal is antiparallel that prevents SHG.

The molecular structure of the title compound (I) (Fig. 1) shows the presence of an N═N [1.2856 (2) A] double bond; the molecule adopts almost planar Z-configuration with the dihedral angle between the two aromatic rings equal to 8.03 (5)°. The endocyclic angles of pyridine ring cover the range 116.64 (5)–124.09 (5)°. The endocyclic angles at the C1 and C5 atoms adjacent to the N1 heteroatom are larger than 120°, and those at the other atoms of the ring are smaller than 120°. Same distribution of endocyclic angles was observed in the other pyridine compounds reported by us earlier (Draguta et al., 2012). The C9—N4, C6—N3 and C4—N2 bond lengths are 1.3666 (15), 1.4213 (17) and 1.4284 (17) Å, respectively, consistent with the single and double bonds between related C and N atoms.

In the absence of hydrogen bonds and stacking, crystal packing of title compound is determined by weak C—H···π (Table 1, Fig. 2) interactions which stabilize herringbone motif into antiparallel molecular orientation, with the angle between molecular vectors connecting C1 and N4 atoms equal to 178.00 (2)°.

Related literature top

For details of the synthesis, see: Peor et al. (2008). For nonlinear optical properties of stilbene derivatives, see: Forrest et al. (1996). For the comparision of nonlinear optical properties of stilbene and diazo derivatives, see: Chemla & Zyss (1987); Morley (1995). For second-harmonic generation in the P212121 space group, see: Rivera et al. (2006). For the distribution of endocyclic angles in pyridine derivatives, see: Draguta et al. (2012).

Experimental top

Title compound was synthesized according to the published procedure (Peor et al., 2008). After purification red plate-like crystals with melting point of 114°C were obtained from slow evaporation from ethanol solution. Second harmonic generation (SHG) in single-crystal of the compound under investigation was tested using irradiation by laser beam with diameter 2 mm, wavelength 1.04 µm, power 700 mW, duration 150 fs at 75 MHz repetition. Initial power density was 2 × 10 6 W cm-2; it was increased step by step up to melting of the sample. UV–Vis: 385 nm; fluorescence: 480 nm.

Refinement top

H atoms attached to C atoms were found in difference Fourier maps and subsequently placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (sp3 C atom). Isotropic displacement parameters for these H atoms were calculated as Uiso(H) = 1.5Ueq(carrier C) in the case of the methyl group, and Uiso(H) = 1.2Ueq(carrier C) otherwise. Since this is a light-atom structure determined with Mo Kα radiation, there is no anomalous signal with which to refine a meaningful Flack parameter. For this reason, 895 Friedel pairs were merged for the final rounds of refinement.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of I. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A portion of the crystal packing, showing the weak C—H···π interactions by dashed lines.
N,N-Diethyl-4-[(E)-(pyridin-3-yl)diazenyl]aniline top
Crystal data top
C15H18N4F(000) = 544
Mr = 254.33Dx = 1.235 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8453 reflections
a = 7.4332 (7) Åθ = 4.5–30.6°
b = 9.1093 (8) ŵ = 0.08 mm−1
c = 20.1946 (19) ÅT = 100 K
V = 1367.4 (2) Å3Plate, red
Z = 40.30 × 0.25 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		4195 independent reflections
Radiation source: fine-focus sealed tube4012 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 30.7°, θmin = 4.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −10→10
Tmin = 0.977, Tmax = 0.985k = −13→13
16318 measured reflectionsl = −28→28
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.050P)2 + 0.7002P]
where P = (Fo2 + 2Fc2)/3
4195 reflections(Δ/σ)max = 0.001
174 parametersΔρmax = 0.62 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C15H18N4V = 1367.4 (2) Å3
Mr = 254.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.4332 (7) ŵ = 0.08 mm−1
b = 9.1093 (8) ÅT = 100 K
c = 20.1946 (19) Å0.30 × 0.25 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		4195 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		4012 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.985Rint = 0.022
16318 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.00Δρmax = 0.62 e Å−3
4195 reflectionsΔρmin = −0.30 e Å−3
174 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N40.00601 (15)0.19116 (12)0.62882 (5)0.0171 (2)
C90.00202 (16)0.29808 (13)0.58137 (6)0.0156 (2)
C40.02116 (18)0.83461 (14)0.38104 (7)0.0203 (2)
C8−0.10014 (18)0.27948 (14)0.52266 (6)0.0188 (2)
H8−0.16620.19140.51610.023*
C100.09862 (17)0.43213 (14)0.58851 (6)0.0190 (2)
H100.16950.44790.62700.023*
N3−0.03161 (16)0.61944 (13)0.42929 (6)0.0214 (2)
C7−0.10486 (19)0.38750 (15)0.47499 (7)0.0214 (2)
H7−0.17360.37200.43600.026*
N20.04908 (15)0.73981 (13)0.43644 (6)0.0216 (2)
N1−0.12281 (17)0.90062 (14)0.27805 (6)0.0252 (2)
C6−0.01126 (18)0.51897 (14)0.48261 (7)0.0202 (2)
C15−0.03051 (19)−0.06308 (14)0.58509 (7)0.0232 (3)
H15A−0.0141−0.03170.53910.035*
H15B−0.1116−0.14790.58650.035*
H15C0.0862−0.09040.60400.035*
C14−0.11139 (17)0.06233 (14)0.62505 (6)0.0182 (2)
H14A−0.22720.09150.60470.022*
H14B−0.13690.02720.67050.022*
C30.1248 (2)0.96131 (17)0.37904 (8)0.0271 (3)
H30.20760.98290.41350.032*
C110.09094 (18)0.54000 (14)0.54022 (7)0.0202 (2)
H110.15550.62900.54620.024*
C1−0.0180 (2)1.02026 (16)0.27692 (7)0.0263 (3)
H1−0.02881.08490.24020.032*
C5−0.10281 (19)0.81021 (15)0.32994 (7)0.0217 (2)
H5−0.17660.72520.33220.026*
C120.13549 (18)0.19273 (15)0.68329 (6)0.0201 (2)
H12A0.24400.24740.66920.024*
H12B0.17240.09060.69310.024*
C20.1047 (2)1.05542 (16)0.32577 (8)0.0292 (3)
H20.17411.14270.32290.035*
C130.0618 (2)0.2623 (2)0.74616 (7)0.0303 (3)
H13A0.03750.36660.73820.045*
H13B0.15040.25250.78180.045*
H13C−0.05000.21280.75900.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N40.0193 (5)0.0161 (4)0.0160 (4)−0.0027 (4)−0.0034 (4)0.0008 (4)
C90.0150 (5)0.0145 (5)0.0173 (5)0.0002 (4)0.0011 (4)−0.0009 (4)
C40.0194 (6)0.0191 (5)0.0224 (6)0.0049 (5)0.0038 (5)0.0017 (4)
C80.0185 (5)0.0175 (5)0.0205 (5)−0.0005 (4)−0.0030 (5)0.0011 (4)
C100.0178 (5)0.0164 (5)0.0228 (5)−0.0006 (5)−0.0006 (5)−0.0031 (4)
N30.0187 (5)0.0212 (5)0.0241 (5)−0.0001 (4)−0.0010 (4)−0.0014 (4)
C70.0207 (6)0.0224 (6)0.0211 (5)0.0028 (5)−0.0025 (5)0.0023 (5)
N20.0196 (5)0.0210 (5)0.0241 (5)0.0008 (4)−0.0007 (4)−0.0009 (4)
N10.0250 (6)0.0263 (6)0.0241 (5)−0.0002 (5)−0.0011 (5)0.0021 (5)
C60.0187 (6)0.0176 (5)0.0242 (6)0.0022 (5)0.0026 (5)0.0028 (4)
C150.0217 (6)0.0174 (5)0.0305 (6)−0.0012 (5)−0.0006 (5)−0.0037 (5)
C140.0181 (5)0.0157 (5)0.0208 (5)−0.0028 (4)−0.0003 (4)0.0016 (4)
C30.0237 (6)0.0271 (7)0.0305 (7)−0.0012 (6)−0.0042 (6)0.0011 (6)
C110.0188 (6)0.0156 (5)0.0262 (6)−0.0004 (5)0.0021 (5)−0.0004 (4)
C10.0253 (6)0.0242 (6)0.0295 (7)0.0016 (5)0.0042 (6)0.0097 (5)
C50.0217 (6)0.0169 (5)0.0266 (6)−0.0001 (5)0.0020 (5)0.0004 (5)
C120.0209 (6)0.0220 (6)0.0174 (5)−0.0008 (5)−0.0050 (4)0.0003 (4)
C20.0240 (6)0.0221 (6)0.0414 (8)−0.0046 (5)0.0011 (6)0.0038 (6)
C130.0338 (8)0.0389 (8)0.0183 (6)−0.0062 (7)−0.0009 (5)−0.0064 (6)
Geometric parameters (Å, º) top
N4—C91.3665 (15)C15—C141.5224 (18)
N4—C141.4645 (16)C15—H15A0.9800
N4—C121.4616 (16)C15—H15B0.9800
C9—C81.4182 (17)C15—H15C0.9800
C9—C101.4239 (17)C14—H14A0.9900
C4—C31.388 (2)C14—H14B0.9900
C4—C51.4012 (19)C3—C21.384 (2)
C4—N21.4285 (17)C3—H30.9500
C8—C71.3770 (18)C11—H110.9500
C8—H80.9500C1—C21.381 (2)
C10—C111.3856 (18)C1—H10.9500
C10—H100.9500C5—H50.9500
N3—N21.2581 (16)C12—C131.5212 (19)
N3—C61.4213 (17)C12—H12A0.9900
C7—C61.3936 (19)C12—H12B0.9900
C7—H70.9500C2—H20.9500
N1—C11.3398 (19)C13—H13A0.9800
N1—C51.3411 (18)C13—H13B0.9800
C6—C111.4027 (19)C13—H13C0.9800
C9—N4—C14121.45 (10)C15—C14—H14A108.9
C9—N4—C12122.34 (11)N4—C14—H14B108.9
C14—N4—C12116.06 (10)C15—C14—H14B108.9
N4—C9—C8120.84 (11)H14A—C14—H14B107.8
N4—C9—C10121.95 (11)C4—C3—C2118.55 (14)
C8—C9—C10117.20 (11)C4—C3—H3120.7
C3—C4—C5118.38 (12)C2—C3—H3120.7
C3—C4—N2116.42 (12)C10—C11—C6120.61 (12)
C5—C4—N2125.20 (12)C10—C11—H11119.7
C7—C8—C9120.85 (12)C6—C11—H11119.7
C7—C8—H8119.6N1—C1—C2124.08 (13)
C9—C8—H8119.6N1—C1—H1118.0
C11—C10—C9121.08 (12)C2—C1—H1118.0
C11—C10—H10119.5N1—C5—C4123.43 (13)
C9—C10—H10119.5N1—C5—H5118.3
N2—N3—C6115.05 (11)C4—C5—H5118.3
C8—C7—C6121.61 (12)N4—C12—C13113.27 (12)
C8—C7—H7119.2N4—C12—H12A108.9
C6—C7—H7119.2C13—C12—H12A108.9
N3—N2—C4111.57 (11)N4—C12—H12B108.9
C1—N1—C5116.64 (13)C13—C12—H12B108.9
C7—C6—C11118.64 (12)H12A—C12—H12B107.7
C7—C6—N3114.62 (12)C1—C2—C3118.88 (14)
C11—C6—N3126.74 (12)C1—C2—H2120.6
C14—C15—H15A109.5C3—C2—H2120.6
C14—C15—H15B109.5C12—C13—H13A109.5
H15A—C15—H15B109.5C12—C13—H13B109.5
C14—C15—H15C109.5H13A—C13—H13B109.5
H15A—C15—H15C109.5C12—C13—H13C109.5
H15B—C15—H15C109.5H13A—C13—H13C109.5
N4—C14—C15113.18 (11)H13B—C13—H13C109.5
N4—C14—H14A108.9
C14—N4—C9—C8−7.75 (18)C9—N4—C14—C1587.55 (14)
C12—N4—C9—C8167.67 (12)C12—N4—C14—C15−88.15 (14)
C14—N4—C9—C10172.05 (11)C5—C4—C3—C2−1.9 (2)
C12—N4—C9—C10−12.53 (18)N2—C4—C3—C2178.95 (13)
N4—C9—C8—C7179.69 (12)C9—C10—C11—C6−0.63 (19)
C10—C9—C8—C7−0.12 (18)C7—C6—C11—C100.04 (19)
N4—C9—C10—C11−179.14 (12)N3—C6—C11—C10179.91 (12)
C8—C9—C10—C110.66 (18)C5—N1—C1—C2−1.0 (2)
C9—C8—C7—C6−0.5 (2)C1—N1—C5—C4−0.7 (2)
C6—N3—N2—C4−179.69 (11)C3—C4—C5—N12.1 (2)
C3—C4—N2—N3−170.84 (12)N2—C4—C5—N1−178.75 (13)
C5—C4—N2—N310.04 (18)C9—N4—C12—C1395.10 (15)
C8—C7—C6—C110.5 (2)C14—N4—C12—C13−89.25 (14)
C8—C7—C6—N3−179.38 (12)N1—C1—C2—C31.2 (2)
N2—N3—C6—C7178.43 (12)C4—C3—C2—C10.3 (2)
N2—N3—C6—C11−1.45 (19)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cgi0.952.603.483 (2)158
Symmetry code: (i) x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cgi0.9502.6033.483 (2)158
Symmetry code: (i) x+1/2, −y+3/2, −z+1.
 

Acknowledgements

The authors are grateful for NSF support via DMR grant Nos. 0934212 (PREM) and CHE 0832622.

References

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ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page o1280
doi:10.1107/S1600536813019545
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