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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1728.
Published online 2009 July 1. doi:  10.1107/S1600536809024623
PMCID: PMC2977232

N,N′-Bis(4-pyridylmethyl­ene)octane-1,8-diamine

Abstract

The complete molecule of the title compound, C20H26N4, is generated by a crystallographic centre of inversion and the central eight-carbon chain adopts a fully extended conformation. In the crystal, the molecules pack in layers parallel to (010).

Related literature

There are only few crystallographic reports of Schiff bases derived from 1,2-octa­nediamine; for details, see: Glidewell et al. (2005 [triangle]); Nathan et al. (2003 [triangle]); Viossat et al. (1997 [triangle]); Yamashita et al. (2003 [triangle]).

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Object name is e-65-o1728-scheme1.jpg

Experimental

Crystal data

  • C20H26N4
  • M r = 322.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1728-efi1.jpg
  • a = 11.6285 (4) Å
  • b = 9.3821 (3) Å
  • c = 8.8302 (3) Å
  • β = 111.143 (2)°
  • V = 898.52 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 140 K
  • 0.40 × 0.20 × 0.02 mm

Data collection

  • Bruker SMART APEX area-detector diffractometer
  • Absorption correction: none
  • 6110 measured reflections
  • 2065 independent reflections
  • 1588 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.138
  • S = 1.02
  • 2065 reflections
  • 109 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024623/ci2836sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024623/ci2836Isup2.hkl

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

Acknowledgments

The authors thank Vijaygarh Jyotish Ray College and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

1,8-Diaminooctane (0.145 g, 1 mmol) was dissolved in methanol (15 ml) and to this was added 4-pyridinecarboxaldehyde (0.215 g, 2 mmol). The mixture was heated for 4 h. The solid that formed was recrystallized from methanol in 70% yield; m.p. 393 K.

Refinement

H atoms were placed in calculated positions (C-H = 0.95-0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C20H26N2 at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.

Crystal data

C20H26N4F(000) = 348
Mr = 322.45Dx = 1.192 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1645 reflections
a = 11.6285 (4) Åθ = 2.2–27.3°
b = 9.3821 (3) ŵ = 0.07 mm1
c = 8.8302 (3) ÅT = 140 K
β = 111.143 (2)°Plate, light yellow
V = 898.52 (5) Å30.40 × 0.20 × 0.02 mm
Z = 2

Data collection

Bruker SMART APEX area-detector diffractometer1588 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
graphiteθmax = 27.5°, θmin = 1.9°
ω scansh = −15→15
6110 measured reflectionsk = −12→11
2065 independent reflectionsl = −11→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0697P)2 + 0.2588P] where P = (Fo2 + 2Fc2)/3
2065 reflections(Δ/σ)max = 0.001
109 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.23 e Å3

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

xyzUiso*/Ueq
N10.28339 (13)0.52618 (14)0.97725 (16)0.0353 (3)
N20.09040 (12)0.40434 (14)1.39134 (15)0.0326 (3)
C10.48329 (13)0.46639 (14)0.56773 (16)0.0248 (3)
H1A0.56010.43880.65730.030*
H1B0.43530.37840.52610.030*
C20.40867 (13)0.56437 (15)0.63471 (17)0.0264 (3)
H2A0.45840.65000.68180.032*
H2B0.33400.59610.54420.032*
C30.36981 (13)0.49380 (15)0.76402 (17)0.0265 (3)
H3A0.30860.41840.71250.032*
H3B0.44260.44760.84510.032*
C40.31509 (18)0.59651 (17)0.8495 (2)0.0413 (4)
H4A0.37480.67400.89790.050*
H4B0.24000.63970.76970.050*
C50.20006 (13)0.58108 (14)1.01734 (16)0.0250 (3)
H50.15980.66470.96310.030*
C60.16301 (12)0.51912 (15)1.14647 (15)0.0225 (3)
C70.07925 (13)0.58973 (15)1.19920 (17)0.0265 (3)
H70.04460.67821.15220.032*
C80.04704 (13)0.52910 (16)1.32146 (18)0.0303 (4)
H8−0.00920.57931.35760.036*
C90.17031 (14)0.33682 (16)1.33808 (18)0.0304 (3)
H90.20180.24731.38520.036*
C100.20944 (13)0.38956 (15)1.21893 (17)0.0263 (3)
H100.26730.33801.18690.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0532 (8)0.0291 (7)0.0383 (7)0.0066 (6)0.0343 (7)0.0070 (6)
N20.0390 (7)0.0354 (7)0.0306 (7)−0.0071 (5)0.0212 (6)−0.0029 (5)
C10.0282 (7)0.0273 (7)0.0236 (7)0.0019 (5)0.0148 (6)0.0008 (5)
C20.0339 (7)0.0257 (7)0.0274 (7)−0.0007 (6)0.0203 (6)0.0006 (6)
C30.0338 (7)0.0256 (7)0.0260 (7)0.0022 (6)0.0181 (6)0.0023 (6)
C40.0682 (11)0.0283 (8)0.0490 (10)0.0084 (7)0.0473 (9)0.0090 (7)
C50.0318 (7)0.0225 (7)0.0238 (7)0.0000 (5)0.0139 (6)0.0003 (5)
C60.0244 (7)0.0245 (7)0.0202 (6)−0.0037 (5)0.0101 (5)−0.0032 (5)
C70.0270 (7)0.0277 (7)0.0274 (7)0.0002 (5)0.0130 (6)−0.0023 (6)
C80.0304 (7)0.0348 (8)0.0323 (8)−0.0035 (6)0.0191 (6)−0.0066 (6)
C90.0387 (8)0.0270 (7)0.0297 (7)−0.0027 (6)0.0174 (6)0.0010 (6)
C100.0308 (7)0.0252 (7)0.0267 (7)0.0001 (5)0.0151 (6)−0.0017 (5)

Geometric parameters (Å, °)

N1—C51.2558 (18)C3—H3B0.99
N1—C41.4643 (18)C4—H4A0.99
N2—C81.334 (2)C4—H4B0.99
N2—C91.3421 (18)C5—C61.4758 (18)
C1—C1i1.522 (2)C5—H50.95
C1—C21.5225 (18)C6—C101.3889 (19)
C1—H1A0.99C6—C71.3898 (18)
C1—H1B0.99C7—C81.3860 (19)
C2—C31.5227 (18)C7—H70.95
C2—H2A0.99C8—H80.95
C2—H2B0.99C9—C101.3800 (19)
C3—C41.4998 (19)C9—H90.95
C3—H3A0.99C10—H100.95
C5—N1—C4117.82 (13)C3—C4—H4A109.3
C8—N2—C9116.48 (12)N1—C4—H4B109.3
C1i—C1—C2113.46 (14)C3—C4—H4B109.3
C1i—C1—H1A108.9H4A—C4—H4B108.0
C2—C1—H1A108.9N1—C5—C6121.75 (13)
C1i—C1—H1B108.9N1—C5—H5119.1
C2—C1—H1B108.9C6—C5—H5119.1
H1A—C1—H1B107.7C10—C6—C7117.76 (12)
C3—C2—C1113.18 (11)C10—C6—C5121.82 (12)
C3—C2—H2A108.9C7—C6—C5120.42 (12)
C1—C2—H2A108.9C8—C7—C6118.97 (13)
C3—C2—H2B108.9C8—C7—H7120.5
C1—C2—H2B108.9C6—C7—H7120.5
H2A—C2—H2B107.8N2—C8—C7123.85 (13)
C4—C3—C2113.11 (12)N2—C8—H8118.1
C4—C3—H3A109.0C7—C8—H8118.1
C2—C3—H3A109.0N2—C9—C10123.94 (14)
C4—C3—H3B109.0N2—C9—H9118.0
C2—C3—H3B109.0C10—C9—H9118.0
H3A—C3—H3B107.8C9—C10—C6119.00 (13)
N1—C4—C3111.63 (12)C9—C10—H10120.5
N1—C4—H4A109.3C6—C10—H10120.5
C1i—C1—C2—C3176.99 (14)C5—C6—C7—C8−179.57 (13)
C1—C2—C3—C4170.37 (14)C9—N2—C8—C70.5 (2)
C5—N1—C4—C3−154.80 (15)C6—C7—C8—N2−1.1 (2)
C2—C3—C4—N1−177.71 (14)C8—N2—C9—C100.6 (2)
C4—N1—C5—C6−179.09 (14)N2—C9—C10—C6−1.0 (2)
N1—C5—C6—C10−6.5 (2)C7—C6—C10—C90.4 (2)
N1—C5—C6—C7173.65 (13)C5—C6—C10—C9−179.46 (13)
C10—C6—C7—C80.6 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2836).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. E61, o3551–o3553.
  • Nathan, L. C., Koehne, J. E., Gilmore, J. M., Hannibal, K. A., Dewhirst, W. E. & Mai, T. D. (2003). Polyhedron, 22, 887–894.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Viossat, B., Dung, N. Y., Labouze, X., Morgant, G., Lancelot, J. C., Perrine, D. & Robba, M. (1997). J. Inorg. Biochem.65, 163–166.
  • Westrip, S. P. (2009). publCIF In preparation.
  • Yamashita, S., Nihei, M. & Oshio, H. (2003). Chem. Lett. pp. 808–809.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography