organic compounds
2,2′-[Nonane-1,9-diylbis(nitrilomethylidyne)]diphenol
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S1600536808039858/hb2862sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808039858/hb2862Isup2.hkl
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.
The C-bound hydrogen atoms were placed at calculated positions (C–H = 0.95—0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The hydroxy H-atom was located in a difference Fourier map and was refined with a distance restraint of O–H = 0.84±0.01 Å.
Data collection: APEX2 (Bruker, 2007); cell
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).C23H30N2O2 | F(000) = 792 |
Mr = 366.49 | Dx = 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 |
Bruker SMART APEX CCD diffractometer | 1573 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 27.5°, θmin = 0.9° |
ω scans | h = −56→56 |
8930 measured reflections | k = −6→6 |
2317 independent reflections | l = −12→12 |
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(Fo2) + (0.1065P)2] where P = (Fo2 + 2Fc2)/3 |
2317 reflections | (Δ/σ)max = 0.001 |
127 parameters | Δρmax = 0.25 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C23H30N2O2 | V = 2027.65 (8) Å3 |
Mr = 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)° |
Bruker SMART APEX CCD diffractometer | 1573 reflections with I > 2σ(I) |
8930 measured reflections | Rint = 0.038 |
2317 independent reflections |
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 | Δρmax = 0.25 e Å−3 |
2317 reflections | Δρmin = −0.23 e Å−3 |
127 parameters |
x | y | z | Uiso*/Ueq | 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 |
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 |
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. |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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For more details, see the Abstract. For the molecular structure, see Fig. 1. and for details of hydrogen bonding, see Table 1.