organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 21 July 2012; accepted 28 July 2012; online 4 August 2012)

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 Schiff bases, see: Khan et al. (2009[Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.]). For the crystal structure of a closely related Schiff base, see: Aslam et al. (2012[Aslam, M., Anis, I., Afza, N., Hussain, M. T. & Yousuf, S. (2012). Acta Cryst. E68, o1447.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13NO

  • Mr = 247.28

  • Orthorhombic, P c a 21

  • a = 13.6348 (17) Å

  • b = 5.8768 (7) Å

  • c = 15.869 (2) Å

  • V = 1271.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 273 K

  • 0.15 × 0.13 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.988, Tmax = 0.992

  • 6852 measured reflections

  • 2300 independent reflections

  • 1655 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.089

  • S = 1.00

  • 2300 reflections

  • 176 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.08 e Å−3

  • Δρmin = −0.09 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1C⋯N1 0.86 (2) 1.86 (2) 2.623 (3) 147 (2)

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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 (CN = 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).

Related literature top

For the biological activity of Schiff bases, see: Khan et al. (2009). For the crystal structure of a closely related Schiff base, see: Aslam et al. (2012).

Experimental top

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.

Refinement top

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 absolute structure was not determined and the Friedle pairs (1082) were not merged.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the unit cell of the title compound showing molecular packing. H atoms were omitted for clarity.
2-[(E)-(Naphthalen-2-yl)iminomethyl]phenol top
Crystal data top
C17H13NOF(000) = 520
Mr = 247.28Dx = 1.292 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1294 reflections
a = 13.6348 (17) Åθ = 2.6–27.8°
b = 5.8768 (7) ŵ = 0.08 mm1
c = 15.869 (2) ÅT = 273 K
V = 1271.5 (3) Å3Block, yellow
Z = 40.15 × 0.13 × 0.10 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2300 independent reflections
Radiation source: fine-focus sealed tube1655 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scanθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1616
Tmin = 0.988, Tmax = 0.992k = 76
6852 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H 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 parametersΔρmax = 0.08 e Å3
2 restraintsΔρmin = 0.09 e Å3
Crystal data top
C17H13NOV = 1271.5 (3) Å3
Mr = 247.28Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 13.6348 (17) ŵ = 0.08 mm1
b = 5.8768 (7) ÅT = 273 K
c = 15.869 (2) Å0.15 × 0.13 × 0.10 mm
Data collection top
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 = 0.992Rint = 0.031
6852 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0382 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.08 e Å3
2300 reflectionsΔρmin = 0.09 e Å3
176 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.51540 (13)1.1177 (3)0.40612 (13)0.0846 (6)
N10.58509 (13)0.7914 (3)0.50171 (12)0.0592 (5)
C10.73882 (15)0.8452 (4)0.56875 (14)0.0542 (5)
H1B0.74130.98510.54150.065*
C20.81650 (15)0.7835 (4)0.62265 (13)0.0519 (5)
C30.89755 (15)0.9265 (4)0.63756 (14)0.0626 (6)
H3A0.90121.06620.61030.075*
C40.97028 (19)0.8641 (4)0.69100 (17)0.0718 (7)
H4A1.02290.96160.70010.086*
C50.96686 (19)0.6547 (5)0.73249 (15)0.0707 (7)
H5A1.01670.61400.76950.085*
C60.89085 (18)0.5111 (4)0.71880 (14)0.0664 (7)
H6A0.89010.37020.74550.080*
C70.81231 (16)0.5715 (4)0.66451 (13)0.0552 (6)
C80.73097 (17)0.4295 (4)0.64880 (16)0.0662 (7)
H8A0.72740.28830.67500.079*
C90.65784 (16)0.4950 (4)0.59615 (17)0.0694 (7)
H9A0.60510.39770.58690.083*
C100.66026 (15)0.7071 (3)0.55524 (14)0.0527 (5)
C110.50538 (16)0.6824 (4)0.49001 (14)0.0591 (6)
H11A0.49760.54000.51470.071*
C120.42625 (15)0.7755 (4)0.43905 (13)0.0538 (6)
C130.33980 (16)0.6545 (4)0.43146 (16)0.0676 (6)
H13A0.33400.51370.45770.081*
C140.26177 (19)0.7392 (5)0.38553 (15)0.0753 (7)
H14A0.20400.65590.38080.090*
C150.27038 (18)0.9489 (5)0.34667 (16)0.0738 (7)
H15A0.21791.00670.31590.089*
C160.35529 (17)1.0725 (5)0.35294 (16)0.0709 (7)
H16A0.36061.21210.32570.085*
C170.43405 (15)0.9890 (4)0.40022 (15)0.0596 (6)
H1C0.5580 (15)1.045 (4)0.4354 (15)0.085 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0667 (11)0.0733 (12)0.1138 (16)0.0103 (10)0.0150 (11)0.0200 (12)
N10.0481 (10)0.0643 (12)0.0652 (12)0.0001 (9)0.0006 (9)0.0003 (10)
C10.0549 (12)0.0528 (13)0.0549 (13)0.0019 (10)0.0028 (11)0.0091 (11)
C20.0526 (12)0.0541 (13)0.0490 (13)0.0030 (10)0.0050 (10)0.0028 (12)
C30.0625 (14)0.0623 (15)0.0628 (15)0.0067 (12)0.0046 (12)0.0083 (13)
C40.0656 (16)0.080 (2)0.0693 (15)0.0074 (13)0.0103 (14)0.0022 (15)
C50.0682 (16)0.0849 (19)0.0589 (14)0.0102 (14)0.0107 (12)0.0035 (15)
C60.0729 (17)0.0688 (15)0.0576 (16)0.0126 (14)0.0048 (14)0.0094 (13)
C70.0581 (13)0.0592 (14)0.0484 (13)0.0059 (11)0.0069 (11)0.0063 (12)
C80.0656 (16)0.0570 (14)0.0759 (17)0.0038 (12)0.0015 (14)0.0200 (13)
C90.0588 (14)0.0648 (16)0.0847 (17)0.0092 (12)0.0021 (14)0.0113 (15)
C100.0483 (12)0.0548 (14)0.0551 (13)0.0041 (10)0.0036 (12)0.0051 (12)
C110.0591 (14)0.0567 (13)0.0616 (15)0.0047 (11)0.0037 (12)0.0055 (12)
C120.0506 (12)0.0585 (14)0.0523 (13)0.0013 (11)0.0029 (10)0.0084 (12)
C130.0669 (14)0.0712 (16)0.0649 (15)0.0051 (13)0.0020 (13)0.0112 (14)
C140.0649 (15)0.095 (2)0.0659 (17)0.0086 (14)0.0118 (13)0.0116 (16)
C150.0617 (15)0.096 (2)0.0642 (16)0.0132 (14)0.0109 (13)0.0180 (16)
C160.0726 (16)0.0752 (18)0.0649 (16)0.0103 (14)0.0071 (15)0.0064 (14)
C170.0521 (13)0.0641 (15)0.0627 (15)0.0007 (11)0.0031 (12)0.0067 (13)
Geometric parameters (Å, º) top
O1—C171.346 (3)C7—C81.410 (3)
O1—H1C0.86 (2)C8—C91.356 (3)
N1—C111.275 (2)C8—H8A0.9300
N1—C101.421 (2)C9—C101.406 (3)
C1—C101.361 (3)C9—H9A0.9300
C1—C21.409 (3)C11—C121.455 (3)
C1—H1B0.9300C11—H11A0.9300
C2—C31.408 (3)C12—C131.382 (3)
C2—C71.413 (3)C12—C171.402 (3)
C3—C41.355 (3)C13—C141.382 (3)
C3—H3A0.9300C13—H13A0.9300
C4—C51.396 (3)C14—C151.383 (3)
C4—H4A0.9300C14—H14A0.9300
C5—C61.354 (3)C15—C161.370 (3)
C5—H5A0.9300C15—H15A0.9300
C6—C71.419 (3)C16—C171.399 (3)
C6—H6A0.9300C16—H16A0.9300
C17—O1—H1C108.4 (18)C8—C9—H9A119.4
C11—N1—C10121.78 (19)C10—C9—H9A119.4
C10—C1—C2122.3 (2)C1—C10—C9118.3 (2)
C10—C1—H1B118.9C1—C10—N1116.99 (18)
C2—C1—H1B118.9C9—C10—N1124.66 (19)
C3—C2—C1122.6 (2)N1—C11—C12121.6 (2)
C3—C2—C7118.60 (19)N1—C11—H11A119.2
C1—C2—C7118.80 (19)C12—C11—H11A119.2
C4—C3—C2121.2 (2)C13—C12—C17119.1 (2)
C4—C3—H3A119.4C13—C12—C11119.2 (2)
C2—C3—H3A119.4C17—C12—C11121.6 (2)
C3—C4—C5120.6 (2)C12—C13—C14121.2 (2)
C3—C4—H4A119.7C12—C13—H13A119.4
C5—C4—H4A119.7C14—C13—H13A119.4
C6—C5—C4119.9 (2)C13—C14—C15119.4 (2)
C6—C5—H5A120.0C13—C14—H14A120.3
C4—C5—H5A120.0C15—C14—H14A120.3
C5—C6—C7121.3 (2)C16—C15—C14120.8 (2)
C5—C6—H6A119.4C16—C15—H15A119.6
C7—C6—H6A119.4C14—C15—H15A119.6
C8—C7—C2118.1 (2)C15—C16—C17120.1 (3)
C8—C7—C6123.5 (2)C15—C16—H16A120.0
C2—C7—C6118.4 (2)C17—C16—H16A120.0
C9—C8—C7121.3 (2)O1—C17—C16118.2 (2)
C9—C8—H8A119.4O1—C17—C12122.3 (2)
C7—C8—H8A119.4C16—C17—C12119.4 (2)
C8—C9—C10121.2 (2)
C10—C1—C2—C3179.4 (2)C8—C9—C10—C10.9 (3)
C10—C1—C2—C70.4 (3)C8—C9—C10—N1177.6 (2)
C1—C2—C3—C4178.8 (2)C11—N1—C10—C1174.8 (2)
C7—C2—C3—C40.2 (3)C11—N1—C10—C93.8 (3)
C2—C3—C4—C50.3 (4)C10—N1—C11—C12176.38 (18)
C3—C4—C5—C60.7 (4)N1—C11—C12—C13177.2 (2)
C4—C5—C6—C71.8 (4)N1—C11—C12—C170.2 (3)
C3—C2—C7—C8179.76 (19)C17—C12—C13—C140.8 (3)
C1—C2—C7—C81.2 (3)C11—C12—C13—C14178.27 (19)
C3—C2—C7—C60.9 (3)C12—C13—C14—C150.1 (3)
C1—C2—C7—C6179.89 (19)C13—C14—C15—C160.3 (4)
C5—C6—C7—C8179.3 (2)C14—C15—C16—C171.1 (4)
C5—C6—C7—C21.9 (3)C15—C16—C17—O1178.7 (2)
C2—C7—C8—C91.0 (3)C15—C16—C17—C121.7 (3)
C6—C7—C8—C9179.8 (2)C13—C12—C17—O1178.9 (2)
C7—C8—C9—C100.1 (4)C11—C12—C17—O11.5 (3)
C2—C1—C10—C90.7 (3)C13—C12—C17—C161.6 (3)
C2—C1—C10—N1177.97 (18)C11—C12—C17—C16179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N10.86 (2)1.86 (2)2.623 (3)147 (2)

Experimental details

Crystal data
Chemical formulaC17H13NO
Mr247.28
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)273
a, b, c (Å)13.6348 (17), 5.8768 (7), 15.869 (2)
V3)1271.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.15 × 0.13 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.988, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
6852, 2300, 1655
Rint0.031
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.089, 1.00
No. of reflections2300
No. of parameters176
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N10.86 (2)1.86 (2)2.623 (3)147 (2)
 

References

First citationAslam, M., Anis, I., Afza, N., Hussain, M. T. & Yousuf, S. (2012). Acta Cryst. E68, o1447.  CSD CrossRef IUCr Journals
First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKhan, 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
First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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