organic compounds
2-[(E)-(Naphthalen-2-yl)iminomethyl]phenol
aDepartment of Chemistry, Forman Christian College (A Chartered University), Lahore, Pakistan, and bH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com
In the title compound, C17H13NO, the azomethine double bond adopts an E conformation. The naphthyl ring system and the benzene ring form a dihedral angle of 8.09 (10)°. The near-planar conformation of the molecule is consolidated by an intramolecular O—H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, molecules are arranged in a zigzag fashion parallel to the c axis.
Related literature
For the biological activity of et al. (2009). For the of a closely related Schiff base, see: Aslam et al. (2012).
see: KhanExperimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812033843/pv2571sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812033843/pv2571Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812033843/pv2571Isup3.cml
4-Chloroaniline (1 ml, 7.29 mmol) was dissolved in analytical grade methanol (10 ml) by continuous stirring followed by the addition of sSalicylaldehyde (0.76 ml, 0.7 mmol) and glacial acetic acid (0.5 ml). The reaction mixture was refluxed at 330–353 K on a hot plate for 2 h with continuous stirring. The progress of the reaction was monitored by TLC. On the completion of the reaction, the product was obtained as dark orange precipitates, which were filtered, washed with distilled water and dried to obtained 1.43 g (77% yield) title compound. The product was dissolved and slow evaporation of a methanol solution affording light yellow crystals suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.
H atoms on carbon atoms were positioned geometrically with C—H = 0.93 Å, and constrained to ride on their parent atoms with Uiso(H)= 1.2Ueq(C). The H atoms on the oxygen (O–H = 0.858 (10) Å) was located in difference Fourier maps and refined isotropically. Due to lack of sufficient anamolous effects, an
was not determined and the Friedle pairs (1082) were not merged.Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).C17H13NO | F(000) = 520 |
Mr = 247.28 | Dx = 1.292 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 1294 reflections |
a = 13.6348 (17) Å | θ = 2.6–27.8° |
b = 5.8768 (7) Å | µ = 0.08 mm−1 |
c = 15.869 (2) Å | T = 273 K |
V = 1271.5 (3) Å3 | Block, yellow |
Z = 4 | 0.15 × 0.13 × 0.10 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2300 independent reflections |
Radiation source: fine-focus sealed tube | 1655 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scan | θmax = 25.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→16 |
Tmin = 0.988, Tmax = 0.992 | k = −7→6 |
6852 measured reflections | l = −19→19 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0383P)2] where P = (Fo2 + 2Fc2)/3 |
2300 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.08 e Å−3 |
2 restraints | Δρmin = −0.09 e Å−3 |
C17H13NO | V = 1271.5 (3) Å3 |
Mr = 247.28 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 13.6348 (17) Å | µ = 0.08 mm−1 |
b = 5.8768 (7) Å | T = 273 K |
c = 15.869 (2) Å | 0.15 × 0.13 × 0.10 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2300 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1655 reflections with I > 2σ(I) |
Tmin = 0.988, Tmax = 0.992 | Rint = 0.031 |
6852 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 2 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.08 e Å−3 |
2300 reflections | Δρmin = −0.09 e Å−3 |
176 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.51540 (13) | 1.1177 (3) | 0.40612 (13) | 0.0846 (6) | |
N1 | 0.58509 (13) | 0.7914 (3) | 0.50171 (12) | 0.0592 (5) | |
C1 | 0.73882 (15) | 0.8452 (4) | 0.56875 (14) | 0.0542 (5) | |
H1B | 0.7413 | 0.9851 | 0.5415 | 0.065* | |
C2 | 0.81650 (15) | 0.7835 (4) | 0.62265 (13) | 0.0519 (5) | |
C3 | 0.89755 (15) | 0.9265 (4) | 0.63756 (14) | 0.0626 (6) | |
H3A | 0.9012 | 1.0662 | 0.6103 | 0.075* | |
C4 | 0.97028 (19) | 0.8641 (4) | 0.69100 (17) | 0.0718 (7) | |
H4A | 1.0229 | 0.9616 | 0.7001 | 0.086* | |
C5 | 0.96686 (19) | 0.6547 (5) | 0.73249 (15) | 0.0707 (7) | |
H5A | 1.0167 | 0.6140 | 0.7695 | 0.085* | |
C6 | 0.89085 (18) | 0.5111 (4) | 0.71880 (14) | 0.0664 (7) | |
H6A | 0.8901 | 0.3702 | 0.7455 | 0.080* | |
C7 | 0.81231 (16) | 0.5715 (4) | 0.66451 (13) | 0.0552 (6) | |
C8 | 0.73097 (17) | 0.4295 (4) | 0.64880 (16) | 0.0662 (7) | |
H8A | 0.7274 | 0.2883 | 0.6750 | 0.079* | |
C9 | 0.65784 (16) | 0.4950 (4) | 0.59615 (17) | 0.0694 (7) | |
H9A | 0.6051 | 0.3977 | 0.5869 | 0.083* | |
C10 | 0.66026 (15) | 0.7071 (3) | 0.55524 (14) | 0.0527 (5) | |
C11 | 0.50538 (16) | 0.6824 (4) | 0.49001 (14) | 0.0591 (6) | |
H11A | 0.4976 | 0.5400 | 0.5147 | 0.071* | |
C12 | 0.42625 (15) | 0.7755 (4) | 0.43905 (13) | 0.0538 (6) | |
C13 | 0.33980 (16) | 0.6545 (4) | 0.43146 (16) | 0.0676 (6) | |
H13A | 0.3340 | 0.5137 | 0.4577 | 0.081* | |
C14 | 0.26177 (19) | 0.7392 (5) | 0.38553 (15) | 0.0753 (7) | |
H14A | 0.2040 | 0.6559 | 0.3808 | 0.090* | |
C15 | 0.27038 (18) | 0.9489 (5) | 0.34667 (16) | 0.0738 (7) | |
H15A | 0.2179 | 1.0067 | 0.3159 | 0.089* | |
C16 | 0.35529 (17) | 1.0725 (5) | 0.35294 (16) | 0.0709 (7) | |
H16A | 0.3606 | 1.2121 | 0.3257 | 0.085* | |
C17 | 0.43405 (15) | 0.9890 (4) | 0.40022 (15) | 0.0596 (6) | |
H1C | 0.5580 (15) | 1.045 (4) | 0.4354 (15) | 0.085 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0667 (11) | 0.0733 (12) | 0.1138 (16) | −0.0103 (10) | −0.0150 (11) | 0.0200 (12) |
N1 | 0.0481 (10) | 0.0643 (12) | 0.0652 (12) | 0.0001 (9) | −0.0006 (9) | 0.0003 (10) |
C1 | 0.0549 (12) | 0.0528 (13) | 0.0549 (13) | 0.0019 (10) | 0.0028 (11) | 0.0091 (11) |
C2 | 0.0526 (12) | 0.0541 (13) | 0.0490 (13) | 0.0030 (10) | 0.0050 (10) | 0.0028 (12) |
C3 | 0.0625 (14) | 0.0623 (15) | 0.0628 (15) | −0.0067 (12) | −0.0046 (12) | 0.0083 (13) |
C4 | 0.0656 (16) | 0.080 (2) | 0.0693 (15) | −0.0074 (13) | −0.0103 (14) | −0.0022 (15) |
C5 | 0.0682 (16) | 0.0849 (19) | 0.0589 (14) | 0.0102 (14) | −0.0107 (12) | 0.0035 (15) |
C6 | 0.0729 (17) | 0.0688 (15) | 0.0576 (16) | 0.0126 (14) | 0.0048 (14) | 0.0094 (13) |
C7 | 0.0581 (13) | 0.0592 (14) | 0.0484 (13) | 0.0059 (11) | 0.0069 (11) | 0.0063 (12) |
C8 | 0.0656 (16) | 0.0570 (14) | 0.0759 (17) | −0.0038 (12) | 0.0015 (14) | 0.0200 (13) |
C9 | 0.0588 (14) | 0.0648 (16) | 0.0847 (17) | −0.0092 (12) | 0.0021 (14) | 0.0113 (15) |
C10 | 0.0483 (12) | 0.0548 (14) | 0.0551 (13) | 0.0041 (10) | 0.0036 (12) | 0.0051 (12) |
C11 | 0.0591 (14) | 0.0567 (13) | 0.0616 (15) | 0.0047 (11) | 0.0037 (12) | −0.0055 (12) |
C12 | 0.0506 (12) | 0.0585 (14) | 0.0523 (13) | 0.0013 (11) | 0.0029 (10) | −0.0084 (12) |
C13 | 0.0669 (14) | 0.0712 (16) | 0.0649 (15) | −0.0051 (13) | −0.0020 (13) | −0.0112 (14) |
C14 | 0.0649 (15) | 0.095 (2) | 0.0659 (17) | −0.0086 (14) | −0.0118 (13) | −0.0116 (16) |
C15 | 0.0617 (15) | 0.096 (2) | 0.0642 (16) | 0.0132 (14) | −0.0109 (13) | −0.0180 (16) |
C16 | 0.0726 (16) | 0.0752 (18) | 0.0649 (16) | 0.0103 (14) | −0.0071 (15) | −0.0064 (14) |
C17 | 0.0521 (13) | 0.0641 (15) | 0.0627 (15) | 0.0007 (11) | 0.0031 (12) | −0.0067 (13) |
O1—C17 | 1.346 (3) | C7—C8 | 1.410 (3) |
O1—H1C | 0.86 (2) | C8—C9 | 1.356 (3) |
N1—C11 | 1.275 (2) | C8—H8A | 0.9300 |
N1—C10 | 1.421 (2) | C9—C10 | 1.406 (3) |
C1—C10 | 1.361 (3) | C9—H9A | 0.9300 |
C1—C2 | 1.409 (3) | C11—C12 | 1.455 (3) |
C1—H1B | 0.9300 | C11—H11A | 0.9300 |
C2—C3 | 1.408 (3) | C12—C13 | 1.382 (3) |
C2—C7 | 1.413 (3) | C12—C17 | 1.402 (3) |
C3—C4 | 1.355 (3) | C13—C14 | 1.382 (3) |
C3—H3A | 0.9300 | C13—H13A | 0.9300 |
C4—C5 | 1.396 (3) | C14—C15 | 1.383 (3) |
C4—H4A | 0.9300 | C14—H14A | 0.9300 |
C5—C6 | 1.354 (3) | C15—C16 | 1.370 (3) |
C5—H5A | 0.9300 | C15—H15A | 0.9300 |
C6—C7 | 1.419 (3) | C16—C17 | 1.399 (3) |
C6—H6A | 0.9300 | C16—H16A | 0.9300 |
C17—O1—H1C | 108.4 (18) | C8—C9—H9A | 119.4 |
C11—N1—C10 | 121.78 (19) | C10—C9—H9A | 119.4 |
C10—C1—C2 | 122.3 (2) | C1—C10—C9 | 118.3 (2) |
C10—C1—H1B | 118.9 | C1—C10—N1 | 116.99 (18) |
C2—C1—H1B | 118.9 | C9—C10—N1 | 124.66 (19) |
C3—C2—C1 | 122.6 (2) | N1—C11—C12 | 121.6 (2) |
C3—C2—C7 | 118.60 (19) | N1—C11—H11A | 119.2 |
C1—C2—C7 | 118.80 (19) | C12—C11—H11A | 119.2 |
C4—C3—C2 | 121.2 (2) | C13—C12—C17 | 119.1 (2) |
C4—C3—H3A | 119.4 | C13—C12—C11 | 119.2 (2) |
C2—C3—H3A | 119.4 | C17—C12—C11 | 121.6 (2) |
C3—C4—C5 | 120.6 (2) | C12—C13—C14 | 121.2 (2) |
C3—C4—H4A | 119.7 | C12—C13—H13A | 119.4 |
C5—C4—H4A | 119.7 | C14—C13—H13A | 119.4 |
C6—C5—C4 | 119.9 (2) | C13—C14—C15 | 119.4 (2) |
C6—C5—H5A | 120.0 | C13—C14—H14A | 120.3 |
C4—C5—H5A | 120.0 | C15—C14—H14A | 120.3 |
C5—C6—C7 | 121.3 (2) | C16—C15—C14 | 120.8 (2) |
C5—C6—H6A | 119.4 | C16—C15—H15A | 119.6 |
C7—C6—H6A | 119.4 | C14—C15—H15A | 119.6 |
C8—C7—C2 | 118.1 (2) | C15—C16—C17 | 120.1 (3) |
C8—C7—C6 | 123.5 (2) | C15—C16—H16A | 120.0 |
C2—C7—C6 | 118.4 (2) | C17—C16—H16A | 120.0 |
C9—C8—C7 | 121.3 (2) | O1—C17—C16 | 118.2 (2) |
C9—C8—H8A | 119.4 | O1—C17—C12 | 122.3 (2) |
C7—C8—H8A | 119.4 | C16—C17—C12 | 119.4 (2) |
C8—C9—C10 | 121.2 (2) | ||
C10—C1—C2—C3 | −179.4 (2) | C8—C9—C10—C1 | 0.9 (3) |
C10—C1—C2—C7 | −0.4 (3) | C8—C9—C10—N1 | −177.6 (2) |
C1—C2—C3—C4 | 178.8 (2) | C11—N1—C10—C1 | −174.8 (2) |
C7—C2—C3—C4 | −0.2 (3) | C11—N1—C10—C9 | 3.8 (3) |
C2—C3—C4—C5 | 0.3 (4) | C10—N1—C11—C12 | 176.38 (18) |
C3—C4—C5—C6 | 0.7 (4) | N1—C11—C12—C13 | −177.2 (2) |
C4—C5—C6—C7 | −1.8 (4) | N1—C11—C12—C17 | 0.2 (3) |
C3—C2—C7—C8 | −179.76 (19) | C17—C12—C13—C14 | 0.8 (3) |
C1—C2—C7—C8 | 1.2 (3) | C11—C12—C13—C14 | 178.27 (19) |
C3—C2—C7—C6 | −0.9 (3) | C12—C13—C14—C15 | −0.1 (3) |
C1—C2—C7—C6 | −179.89 (19) | C13—C14—C15—C16 | 0.3 (4) |
C5—C6—C7—C8 | −179.3 (2) | C14—C15—C16—C17 | −1.1 (4) |
C5—C6—C7—C2 | 1.9 (3) | C15—C16—C17—O1 | −178.7 (2) |
C2—C7—C8—C9 | −1.0 (3) | C15—C16—C17—C12 | 1.7 (3) |
C6—C7—C8—C9 | −179.8 (2) | C13—C12—C17—O1 | 178.9 (2) |
C7—C8—C9—C10 | −0.1 (4) | C11—C12—C17—O1 | 1.5 (3) |
C2—C1—C10—C9 | −0.7 (3) | C13—C12—C17—C16 | −1.6 (3) |
C2—C1—C10—N1 | 177.97 (18) | C11—C12—C17—C16 | −179.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···N1 | 0.86 (2) | 1.86 (2) | 2.623 (3) | 147 (2) |
Experimental details
Crystal data | |
Chemical formula | C17H13NO |
Mr | 247.28 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 273 |
a, b, c (Å) | 13.6348 (17), 5.8768 (7), 15.869 (2) |
V (Å3) | 1271.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.15 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.988, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6852, 2300, 1655 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.089, 1.00 |
No. of reflections | 2300 |
No. of parameters | 176 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.08, −0.09 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···N1 | 0.86 (2) | 1.86 (2) | 2.623 (3) | 147 (2) |
References
Aslam, M., Anis, I., Afza, N., Hussain, M. T. & Yousuf, S. (2012). Acta Cryst. E68, o1447. CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795–7801. Web of Science CrossRef PubMed CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Schiff bases represent a broad class of organic compounds that are reported to have a wide range of biological activities (Khan et al., 2009). The title compound was synthesized as a part of our ongoing research to study the biological activities of structurally diverse Schiff bases. The title compound (Fig. 1) is composed of a naphthyl (C1–C10) and a benzene rings (C12–C17) linked through an azomethine (C═N = 1.275 (2) Å) double bond which adopts an E configuration. The dihedral angle between the naphthyl and the benzene rings is 8.09 (10)° with maximum deviation of 0.013 (3) Å for C5 atom from the root mean square plane of the naphthyl ring. The bond lengths and angle in the title molecule are similar to the corresponding bond lengths and angles in a closely related Schiff base (Aslam et al. 2012). The molecular structure is stabilized by an intramolecular O1—H1C···N1 hydrogen bond to form S(6) graph set ring motif. In the crystal structure the molecules are arranged in a zig zag fashion to form sheets parallel to the c-axis (Fig.2).