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

Patra, G.K.; Mukherjee, A.; Mitra, P.; Ng, S.W.

doi:10.1107/S1600536809024623

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1728

doi:10.1107/S1600536809024623

Open

access

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

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

^aDepartment of Chemistry, Vijaygarh Jyotish Ray College, 8/2 Vijaygarh, Jadavpur, Kolkata 700 032, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 June 2009; accepted 26 June 2009; online 1 July 2009)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 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 ).

Supporting information

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

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

checkCIF report

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

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

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

Crystal data top

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

Data collection top

Bruker SMART APEX area-detector diffractometer	1588 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	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

Refinement top

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

Crystal data top

C₂₀H₂₆N₄	V = 898.52 (5) Å³
M_r = 322.45	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6285 (4) Å	µ = 0.07 mm⁻¹
b = 9.3821 (3) Å	T = 140 K
c = 8.8302 (3) Å	0.40 × 0.20 × 0.02 mm
β = 111.143 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	1588 reflections with I > 2σ(I)
6110 measured reflections	R_int = 0.023
2065 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
2065 reflections	Δρ_min = −0.23 e Å⁻³
109 parameters

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

	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆N₄
M_r	322.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	140
a, b, c (Å)	11.6285 (4), 9.3821 (3), 8.8302 (3)
β (°)	111.143 (2)
V (Å³)	898.52 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.20 × 0.02

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6110, 2065, 1588
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.138, 1.02
No. of reflections	2065
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

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

References

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