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

Goutam Kumar Patra; Anindita Mukherjee; Partha Mitra; Seik Weng Ng

doi:10.1107/S1600536809024623

. 2009 Jul 1;65(Pt 8):o1728. doi: 10.1107/S1600536809024623

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

Goutam Kumar Patra ^a, Anindita Mukherjee ^a, Partha Mitra ^a, Seik Weng Ng ^b,^*

PMCID: PMC2977232 PMID: 21583445

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 ▶); Nathan et al. (2003 ▶); Viossat et al. (1997 ▶); Yamashita et al. (2003 ▶).

Experimental

Crystal data

C₂₀H₂₆N₄
M _r = 322.45
Monoclinic,
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
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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

Supplementary Material

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

e-65-o1728-sup1.cif^{(13.6KB, cif)}

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

e-65-o1728-Isup2.hkl^{(101.6KB, 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.

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

C₂₀H₂₆N₄	F(000) = 348
M_r = 322.45	D_x = 1.192 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1645 reflections
a = 11.6285 (4) Å	θ = 2.2–27.3°
b = 9.3821 (3) Å	µ = 0.07 mm⁻¹
c = 8.8302 (3) Å	T = 140 K
β = 111.143 (2)°	Plate, light yellow
V = 898.52 (5) Å³	0.40 × 0.20 × 0.02 mm
Z = 2

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Data collection

Bruker SMART APEX area-detector diffractometer	1588 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
graphite	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −15→15
6110 measured reflections	k = −12→11
2065 independent reflections	l = −11→11

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Refinement

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0697P)² + 0.2588P] where P = (F_o² + 2F_c²)/3
2065 reflections	(Δ/σ)_max = 0.001
109 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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

	x	y	z	U_iso*/U_eq
N1	0.28339 (13)	0.52618 (14)	0.97725 (16)	0.0353 (3)
N2	0.09040 (12)	0.40434 (14)	1.39134 (15)	0.0326 (3)
C1	0.48329 (13)	0.46639 (14)	0.56773 (16)	0.0248 (3)
H1A	0.5601	0.4388	0.6573	0.030*
H1B	0.4353	0.3784	0.5261	0.030*
C2	0.40867 (13)	0.56437 (15)	0.63471 (17)	0.0264 (3)
H2A	0.4584	0.6500	0.6818	0.032*
H2B	0.3340	0.5961	0.5442	0.032*
C3	0.36981 (13)	0.49380 (15)	0.76402 (17)	0.0265 (3)
H3A	0.3086	0.4184	0.7125	0.032*
H3B	0.4426	0.4476	0.8451	0.032*
C4	0.31509 (18)	0.59651 (17)	0.8495 (2)	0.0413 (4)
H4A	0.3748	0.6740	0.8979	0.050*
H4B	0.2400	0.6397	0.7697	0.050*
C5	0.20006 (13)	0.58108 (14)	1.01734 (16)	0.0250 (3)
H5	0.1598	0.6647	0.9631	0.030*
C6	0.16301 (12)	0.51912 (15)	1.14647 (15)	0.0225 (3)
C7	0.07925 (13)	0.58973 (15)	1.19920 (17)	0.0265 (3)
H7	0.0446	0.6782	1.1522	0.032*
C8	0.04704 (13)	0.52910 (16)	1.32146 (18)	0.0303 (4)
H8	−0.0092	0.5793	1.3576	0.036*
C9	0.17031 (14)	0.33682 (16)	1.33808 (18)	0.0304 (3)
H9	0.2018	0.2473	1.3852	0.036*
C10	0.20944 (13)	0.38956 (15)	1.21893 (17)	0.0263 (3)
H10	0.2673	0.3380	1.1869	0.032*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0532 (8)	0.0291 (7)	0.0383 (7)	0.0066 (6)	0.0343 (7)	0.0070 (6)
N2	0.0390 (7)	0.0354 (7)	0.0306 (7)	−0.0071 (5)	0.0212 (6)	−0.0029 (5)
C1	0.0282 (7)	0.0273 (7)	0.0236 (7)	0.0019 (5)	0.0148 (6)	0.0008 (5)
C2	0.0339 (7)	0.0257 (7)	0.0274 (7)	−0.0007 (6)	0.0203 (6)	0.0006 (6)
C3	0.0338 (7)	0.0256 (7)	0.0260 (7)	0.0022 (6)	0.0181 (6)	0.0023 (6)
C4	0.0682 (11)	0.0283 (8)	0.0490 (10)	0.0084 (7)	0.0473 (9)	0.0090 (7)
C5	0.0318 (7)	0.0225 (7)	0.0238 (7)	0.0000 (5)	0.0139 (6)	0.0003 (5)
C6	0.0244 (7)	0.0245 (7)	0.0202 (6)	−0.0037 (5)	0.0101 (5)	−0.0032 (5)
C7	0.0270 (7)	0.0277 (7)	0.0274 (7)	0.0002 (5)	0.0130 (6)	−0.0023 (6)
C8	0.0304 (7)	0.0348 (8)	0.0323 (8)	−0.0035 (6)	0.0191 (6)	−0.0066 (6)
C9	0.0387 (8)	0.0270 (7)	0.0297 (7)	−0.0027 (6)	0.0174 (6)	0.0010 (6)
C10	0.0308 (7)	0.0252 (7)	0.0267 (7)	0.0001 (5)	0.0151 (6)	−0.0017 (5)

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Geometric parameters (Å, °)

N1—C5	1.2558 (18)	C3—H3B	0.99
N1—C4	1.4643 (18)	C4—H4A	0.99
N2—C8	1.334 (2)	C4—H4B	0.99
N2—C9	1.3421 (18)	C5—C6	1.4758 (18)
C1—C1ⁱ	1.522 (2)	C5—H5	0.95
C1—C2	1.5225 (18)	C6—C10	1.3889 (19)
C1—H1A	0.99	C6—C7	1.3898 (18)
C1—H1B	0.99	C7—C8	1.3860 (19)
C2—C3	1.5227 (18)	C7—H7	0.95
C2—H2A	0.99	C8—H8	0.95
C2—H2B	0.99	C9—C10	1.3800 (19)
C3—C4	1.4998 (19)	C9—H9	0.95
C3—H3A	0.99	C10—H10	0.95

C5—N1—C4	117.82 (13)	C3—C4—H4A	109.3
C8—N2—C9	116.48 (12)	N1—C4—H4B	109.3
C1ⁱ—C1—C2	113.46 (14)	C3—C4—H4B	109.3
C1ⁱ—C1—H1A	108.9	H4A—C4—H4B	108.0
C2—C1—H1A	108.9	N1—C5—C6	121.75 (13)
C1ⁱ—C1—H1B	108.9	N1—C5—H5	119.1
C2—C1—H1B	108.9	C6—C5—H5	119.1
H1A—C1—H1B	107.7	C10—C6—C7	117.76 (12)
C3—C2—C1	113.18 (11)	C10—C6—C5	121.82 (12)
C3—C2—H2A	108.9	C7—C6—C5	120.42 (12)
C1—C2—H2A	108.9	C8—C7—C6	118.97 (13)
C3—C2—H2B	108.9	C8—C7—H7	120.5
C1—C2—H2B	108.9	C6—C7—H7	120.5
H2A—C2—H2B	107.8	N2—C8—C7	123.85 (13)
C4—C3—C2	113.11 (12)	N2—C8—H8	118.1
C4—C3—H3A	109.0	C7—C8—H8	118.1
C2—C3—H3A	109.0	N2—C9—C10	123.94 (14)
C4—C3—H3B	109.0	N2—C9—H9	118.0
C2—C3—H3B	109.0	C10—C9—H9	118.0
H3A—C3—H3B	107.8	C9—C10—C6	119.00 (13)
N1—C4—C3	111.63 (12)	C9—C10—H10	120.5
N1—C4—H4A	109.3	C6—C10—H10	120.5

C1ⁱ—C1—C2—C3	176.99 (14)	C5—C6—C7—C8	−179.57 (13)
C1—C2—C3—C4	170.37 (14)	C9—N2—C8—C7	0.5 (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—C10	0.6 (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—C9	0.4 (2)
N1—C5—C6—C7	173.65 (13)	C5—C6—C10—C9	−179.46 (13)
C10—C6—C7—C8	0.6 (2)

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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. [DOI] [PubMed]
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. [DOI] [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.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-o1728-sup1.cif^{(13.6KB, cif)}

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

e-65-o1728-Isup2.hkl^{(101.6KB, hkl)}

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

[bb1] Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.

[bb2] Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.

[bb3] Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. E61, o3551–o3553. [DOI] [PubMed]

[bb4] Nathan, L. C., Koehne, J. E., Gilmore, J. M., Hannibal, K. A., Dewhirst, W. E. & Mai, T. D. (2003). Polyhedron, 22, 887–894.

[bb5] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb6] Viossat, B., Dung, N. Y., Labouze, X., Morgant, G., Lancelot, J. C., Perrine, D. & Robba, M. (1997). J. Inorg. Biochem.65, 163–166.

[bb7] Westrip, S. P. (2009). publCIF In preparation.

[bb8] Yamashita, S., Nihei, M. & Oshio, H. (2003). Chem. Lett. pp. 808–809.

PERMALINK

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

Goutam Kumar Patra

Anindita Mukherjee

Partha Mitra

Seik Weng Ng

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

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

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Cite

Add to Collections

PERMALINK

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

Goutam Kumar Patra

Anindita Mukherjee

Partha Mitra

Seik Weng Ng

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Similar articles

Cited by other articles

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

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

Atomic displacement parameters (Å²)