2,2′-[Nonane-1,9-diylbis(nitrilo­methyl­idyne)]diphenol

Abdullah, N.; Lo, K.M.; Tajuddin, H.A.; Tee, J.T.; Ng, S.W.

doi:10.1107/S1600536808039858

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2494

doi:10.1107/S1600536808039858

Open

access

2,2′-[Nonane-1,9-diylbis(nitrilomethylidyne)]diphenol

Norbani Abdullah,^a Kong Mun Lo,^a Hairul Anuar Tajuddin,^a Jia Ti Tee ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 November 2008; accepted 26 November 2008; online 29 November 2008)

In the title Schiff base compound, C₂₃H₃₀N₂O₂, the complete molecule is generated by crystallographic twofold symmetry, with one C atom lying on the rotation axis. The nonane chain adopts a linear conformation and the hydroxy group forms an intramolecular O—H⋯N hydrogen bond to the imine group.

Related literature

For the effect of alkyl length on the optical properties of 2,2′-[alkyl-1,9-diylbis(nitrilomethylidyne)]diphenols, see: Kawasaki et al. (1996 , 1999 ). For the reduction of the Schiff base to the secondary diamine, see: Csaszar (1984 ). For the structure of 2,2′-[hexane-1,6-diylbis(nitrilomethylidyne)]diphenol, see: Sheikhshoaie & Sharif (2006 ).

Experimental

Crystal data

C₂₃H₃₀N₂O₂
M_r = 366.49
Monoclinic, C 2/c
a = 43.6905 (10) Å
b = 4.7258 (1) Å
c = 9.8928 (2) Å
β = 96.935 (2)°
V = 2027.65 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.40 × 0.03 × 0.02 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: none
8930 measured reflections
2317 independent reflections
1573 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.177
S = 1.10
2317 reflections
127 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.86 (1)	1.81 (2)	2.5755 (19)	148 (3)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039858/hb2862sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039858/hb2862Isup2.hkl

checkCIF report

Comment top

For more details, see the Abstract. For the molecular structure, see Fig. 1. and for details of hydrogen bonding, see Table 1.

Related literature top

For the effect of alkyl length on the optical properties of 2,2'-[alkyl-1,9-diylbis(nitrilomethylidyne)]diphenols, see: Kawasaki et al. (1996, 1999). For the reduction of the Schiff base to the secondary diamine, see: Csaszar (1984). For the structure of 2,2'-[hexane-1,6-diylbis(nitrilomethylidyne)]diphenol, see: Sheikhshoaie & Sharif (2006).

Experimental top

Salicylaldehyde (0.050 mol, 6.1 g) and sodium hydroxide (0.05 mol, 2.0 g) in methanol (125 ml) was added to 1,9-diaminononane (0.025 mol, 3.9 g) in methanol (125 ml). The solution was heated for 1 h. The solvent was evaporated and the product recrystallized from ethanol to yield yellow plates of (I). The rod used for data collection was cut from a plate.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top

Fig. 1. View of the molecular structure of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The unlabelled atoms are generated by the symmetry operation (1–x, y, 1/2–z).

2,2'-[Nonane-1,9-diylbis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₃H₃₀N₂O₂	F(000) = 792
M_r = 366.49	D_x = 1.201 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2058 reflections
a = 43.6905 (10) Å	θ = 2.8–27.9°
b = 4.7258 (1) Å	µ = 0.08 mm⁻¹
c = 9.8928 (2) Å	T = 100 K
β = 96.935 (2)°	Rod, yellow
V = 2027.65 (8) Å³	0.40 × 0.03 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	1573 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 27.5°, θ_min = 0.9°
ω scans	h = −56→56
8930 measured reflections	k = −6→6
2317 independent reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.1065P)²] where P = (F_o² + 2F_c²)/3
2317 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₃₀N₂O₂	V = 2027.65 (8) Å³
M_r = 366.49	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 43.6905 (10) Å	µ = 0.08 mm⁻¹
b = 4.7258 (1) Å	T = 100 K
c = 9.8928 (2) Å	0.40 × 0.03 × 0.02 mm
β = 96.935 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	1573 reflections with I > 2σ(I)
8930 measured reflections	R_int = 0.038
2317 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.25 e Å⁻³
2317 reflections	Δρ_min = −0.23 e Å⁻³
127 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.63065 (3)	0.8920 (3)	0.86876 (12)	0.0364 (4)
H1	0.6186 (5)	0.787 (5)	0.816 (2)	0.075 (8)*
N1	0.61425 (3)	0.4953 (3)	0.69663 (13)	0.0283 (4)
C1	0.66008 (4)	0.8348 (4)	0.84965 (15)	0.0300 (4)
C2	0.68388 (4)	0.9845 (4)	0.92417 (17)	0.0382 (5)
H2	0.6793	1.1251	0.9874	0.046*
C3	0.71405 (4)	0.9284 (4)	0.90596 (19)	0.0410 (5)
H3	0.7302	1.0303	0.9577	0.049*
C4	0.72134 (4)	0.7262 (4)	0.81367 (19)	0.0388 (5)
H4	0.7422	0.6916	0.8009	0.047*
C5	0.69785 (4)	0.5759 (4)	0.74073 (18)	0.0344 (4)
H5	0.7027	0.4358	0.6779	0.041*
C6	0.66712 (4)	0.6252 (3)	0.75711 (15)	0.0281 (4)
C7	0.64264 (4)	0.4541 (4)	0.68374 (15)	0.0282 (4)
H7	0.6480	0.3082	0.6249	0.034*
C8	0.59137 (4)	0.3110 (4)	0.62109 (16)	0.0295 (4)
H8A	0.5792	0.2140	0.6854	0.035*
H8B	0.6020	0.1649	0.5720	0.035*
C9	0.56994 (4)	0.4833 (4)	0.51955 (16)	0.0290 (4)
H9A	0.5590	0.6250	0.5696	0.035*
H9B	0.5824	0.5867	0.4584	0.035*
C10	0.54637 (4)	0.2996 (4)	0.43422 (16)	0.0295 (4)
H10A	0.5351	0.1845	0.4957	0.035*
H10B	0.5573	0.1683	0.3786	0.035*
C11	0.52325 (3)	0.4723 (4)	0.34047 (16)	0.0278 (4)
H11A	0.5347	0.5929	0.2818	0.033*
H11B	0.5119	0.5990	0.3968	0.033*
C12	0.5000	0.2941 (5)	0.2500	0.0291 (5)
H12A	0.4888	0.1707	0.3082	0.035*	0.50
H12B	0.5112	0.1707	0.1918	0.035*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0363 (8)	0.0429 (8)	0.0299 (7)	0.0016 (6)	0.0041 (5)	−0.0045 (5)
N1	0.0256 (8)	0.0366 (8)	0.0213 (7)	0.0014 (6)	−0.0026 (5)	0.0018 (6)
C1	0.0343 (10)	0.0354 (9)	0.0194 (7)	0.0001 (7)	−0.0007 (7)	0.0058 (7)
C2	0.0489 (12)	0.0379 (10)	0.0259 (8)	−0.0070 (8)	−0.0036 (8)	0.0002 (8)
C3	0.0395 (11)	0.0436 (11)	0.0361 (10)	−0.0118 (8)	−0.0115 (8)	0.0069 (8)
C4	0.0286 (10)	0.0441 (11)	0.0415 (10)	−0.0031 (8)	−0.0053 (8)	0.0083 (8)
C5	0.0307 (10)	0.0396 (10)	0.0318 (9)	0.0013 (7)	−0.0006 (7)	0.0039 (7)
C6	0.0298 (9)	0.0331 (9)	0.0204 (7)	0.0006 (7)	−0.0018 (6)	0.0055 (6)
C7	0.0281 (9)	0.0352 (9)	0.0204 (7)	0.0029 (7)	−0.0008 (6)	0.0019 (6)
C8	0.0251 (9)	0.0352 (9)	0.0269 (8)	0.0007 (7)	−0.0017 (7)	0.0005 (7)
C9	0.0238 (9)	0.0354 (9)	0.0266 (8)	0.0014 (7)	−0.0018 (7)	0.0002 (7)
C10	0.0238 (9)	0.0334 (9)	0.0302 (8)	0.0020 (6)	−0.0012 (7)	−0.0005 (7)
C11	0.0231 (8)	0.0332 (9)	0.0265 (8)	0.0013 (6)	0.0005 (6)	−0.0006 (6)
C12	0.0230 (12)	0.0327 (12)	0.0306 (11)	0.000	−0.0010 (9)	0.000

Geometric parameters (Å, º) top

O1—C1	1.349 (2)	C8—C9	1.524 (2)
O1—H1	0.86 (1)	C8—H8A	0.9900
N1—C7	1.277 (2)	C8—H8B	0.9900
N1—C8	1.461 (2)	C9—C10	1.522 (2)
C1—C2	1.393 (2)	C9—H9A	0.9900
C1—C6	1.408 (2)	C9—H9B	0.9900
C2—C3	1.377 (3)	C10—C11	1.523 (2)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.385 (3)	C10—H10B	0.9900
C3—H3	0.9500	C11—C12	1.524 (2)
C4—C5	1.378 (2)	C11—H11A	0.9900
C4—H4	0.9500	C11—H11B	0.9900
C5—C6	1.391 (2)	C12—C11ⁱ	1.524 (2)
C5—H5	0.9500	C12—H12A	0.9900
C6—C7	1.462 (2)	C12—H12B	0.9900
C7—H7	0.9500

C1—O1—H1	109.1 (19)	C9—C8—H8B	109.6
C7—N1—C8	118.06 (14)	H8A—C8—H8B	108.1
O1—C1—C2	119.15 (16)	C10—C9—C8	112.43 (14)
O1—C1—C6	121.25 (15)	C10—C9—H9A	109.1
C2—C1—C6	119.60 (16)	C8—C9—H9A	109.1
C3—C2—C1	119.86 (17)	C10—C9—H9B	109.1
C3—C2—H2	120.1	C8—C9—H9B	109.1
C1—C2—H2	120.1	H9A—C9—H9B	107.9
C2—C3—C4	121.26 (17)	C9—C10—C11	112.75 (14)
C2—C3—H3	119.4	C9—C10—H10A	109.0
C4—C3—H3	119.4	C11—C10—H10A	109.0
C5—C4—C3	118.99 (18)	C9—C10—H10B	109.0
C5—C4—H4	120.5	C11—C10—H10B	109.0
C3—C4—H4	120.5	H10A—C10—H10B	107.8
C4—C5—C6	121.38 (17)	C10—C11—C12	114.05 (15)
C4—C5—H5	119.3	C10—C11—H11A	108.7
C6—C5—H5	119.3	C12—C11—H11A	108.7
C5—C6—C1	118.89 (15)	C10—C11—H11B	108.7
C5—C6—C7	120.52 (15)	C12—C11—H11B	108.7
C1—C6—C7	120.54 (15)	H11A—C11—H11B	107.6
N1—C7—C6	121.81 (15)	C11—C12—C11ⁱ	112.9 (2)
N1—C7—H7	119.1	C11—C12—H12A	109.0
C6—C7—H7	119.1	C11ⁱ—C12—H12A	109.0
N1—C8—C9	110.26 (14)	C11—C12—H12B	109.0
N1—C8—H8A	109.6	C11ⁱ—C12—H12B	109.0
C9—C8—H8A	109.6	H12A—C12—H12B	107.8
N1—C8—H8B	109.6

O1—C1—C2—C3	179.92 (15)	C2—C1—C6—C7	176.40 (14)
C6—C1—C2—C3	0.6 (2)	C8—N1—C7—C6	−179.01 (14)
C1—C2—C3—C4	0.5 (3)	C5—C6—C7—N1	−179.81 (16)
C2—C3—C4—C5	−1.1 (3)	C1—C6—C7—N1	2.8 (2)
C3—C4—C5—C6	0.6 (3)	C7—N1—C8—C9	−117.30 (16)
C4—C5—C6—C1	0.5 (2)	N1—C8—C9—C10	177.84 (13)
C4—C5—C6—C7	−176.97 (15)	C8—C9—C10—C11	175.42 (14)
O1—C1—C6—C5	179.62 (14)	C9—C10—C11—C12	177.98 (12)
C2—C1—C6—C5	−1.0 (2)	C10—C11—C12—C11ⁱ	178.76 (15)
O1—C1—C6—C7	−3.0 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (1)	1.81 (2)	2.5755 (19)	148 (3)

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀N₂O₂
M_r	366.49
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	43.6905 (10), 4.7258 (1), 9.8928 (2)
β (°)	96.935 (2)
V (Å³)	2027.65 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.03 × 0.02

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8930, 2317, 1573
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.177, 1.10
No. of reflections	2317
No. of parameters	127
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (1)	1.81 (2)	2.5755 (19)	148 (3)

Acknowledgements

We thank the Fundamental Research Grant Scheme of the Ministry of Higher Education for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Csaszar, J. (1984). Acta Phys. Chem. 30, 61. Google Scholar
Kawasaki, T., Kamata, T., Ushijima, H., Kanakubo, M., Murata, S., Mizukami, F., Fujii, Y. & Usui, Y. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 193–198. CrossRef Google Scholar
Kawasaki, T., Kamata, T., Ushijima, H., Murata, S., Mizukami, F., Fujii, Y. & Usui, Y. (1996). Mol. Cryst. Liq. Cryst. 286, 579–584. CrossRef CAS Google Scholar
Sheikhshoaie, I. & Sharif, M. A. (2006). Acta Cryst. E62, o3563–o3565. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar