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The title compound, C18H12N2O, crystallizes in a phenol–imine tautomeric form with a Z conformation for the imine functionality. The dihedral angle between the aromatic rings is 8.98 (9)°. A strong intra­molecular O—H...N hydrogen-bond inter­action between the hydroxyl group and imine N atom occurs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809023708/bh2232sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809023708/bh2232Isup2.hkl
Contains datablock I

CCDC reference: 741695

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.066
  • wR factor = 0.159
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C13 - C18 ... 1.44 Ang.
Alert level G PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1 -C10 1.41 Ang. PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 = 4 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff base compounds have received considerable attention for many years because these compounds play an important role in coordination chemistry related to magnetism (Weber et al., 2007) and catalysis (Chen et al., 2008).Our group is interested in the synthesis and preparation of Schiff bases. Here, we report the synthesis and crystal structure of the title compound.

Figure 1 shows an ORTEP plot of the title compound. The molecule adopts the phenol–imine tautomeric form with a strong intramolecular O—H···N hydrogen bond. The C11N1 and C2—O1 bond lengths [1.296 (3) and 1.324 (3) Å, respectively] are comparable to corresponding values observed in a similar phenol–imine tautomeric structures (e.g. Petek et al., 2007), while different geometry is observed in the case of zwitterionic molecules (Elmali et al., 2001; Yüce et al., 2006). Phenyl and naphthalyl rings, A (C12···C17) and B (C1···C10), are, of course, planar, and the dihedral angle between them is 8.98 (9)°. The molecule displays a trans configuration about the central CN imine bond. Molecules are packed in the crystal at van der Waals distances.

Related literature top

For general properties of Schiff base compounds, see: Weber et al. (2007); Chen et al. (2008). For related structures, see: Elmali et al. (2001); Yüce et al. (2006); Petek et al. (2007).

Experimental top

2-Aminobenzonitrile (0.59 g, 5 mmol) and 2-hydroxynaphthalene-1-carbaldehyde (0.861 g, 5 mmol) were dissolved in ethanol (25 ml). The resulting mixture was refluxed for 5 h and cooled to room temperature. The solid product was collected by filtration. Crystals suitable for X-ray diffraction studies were obtained on slow evaporation at room temperature.

Refinement top

The H atoms were placed geometrically and treated as riding atoms with O—H = 0.82 Å and C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(Carrier C) and Uiso(H1A) = 1.5Ueq(O1).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
(Z)-2-[(2-Hydroxy-1-naphthyl)methyleneamino]benzonitrile top
Crystal data top
C18H12N2OF(000) = 568
Mr = 272.30Dx = 1.310 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2198 reflections
a = 13.4640 (13) Åθ = 2.7–27.5°
b = 7.4450 (6) ŵ = 0.08 mm1
c = 15.4090 (11) ÅT = 293 K
β = 116.660 (6)°Block, pale yellow
V = 1380.4 (2) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer
2706 independent reflections
Radiation source: fine-focus sealed tube1803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = 1616
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 99
Tmin = 0.973, Tmax = 0.979l = 1818
12133 measured reflections
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0672P)2 + 0.1372P]
where P = (Fo2 + 2Fc2)/3
2706 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.18 e Å3
0 constraints
Crystal data top
C18H12N2OV = 1380.4 (2) Å3
Mr = 272.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.4640 (13) ŵ = 0.08 mm1
b = 7.4450 (6) ÅT = 293 K
c = 15.4090 (11) Å0.20 × 0.20 × 0.20 mm
β = 116.660 (6)°
Data collection top
Rigaku SCXmini
diffractometer
2706 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1803 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.979Rint = 0.056
12133 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.10Δρmax = 0.20 e Å3
2706 reflectionsΔρmin = 0.18 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.22890 (15)0.5907 (3)0.07648 (12)0.0792 (6)
H1A0.17180.64360.08520.119*
N10.07487 (14)0.7038 (2)0.03712 (12)0.0490 (5)
N20.0188 (2)0.7966 (4)0.27347 (16)0.0894 (8)
C10.24373 (17)0.5812 (3)0.08450 (16)0.0465 (5)
C110.13677 (17)0.6610 (3)0.05282 (16)0.0459 (5)
H11A0.11050.68310.09830.055*
C120.03185 (17)0.7809 (3)0.07090 (15)0.0439 (5)
C130.08320 (18)0.8360 (3)0.16755 (16)0.0500 (6)
C100.30954 (17)0.5267 (3)0.18411 (16)0.0477 (6)
C60.4729 (2)0.3710 (3)0.3064 (2)0.0674 (7)
H6A0.53810.30680.32280.081*
C50.41020 (19)0.4302 (3)0.21022 (18)0.0550 (6)
C90.2793 (2)0.5638 (3)0.25909 (17)0.0582 (6)
H9A0.21500.62900.24510.070*
C20.2839 (2)0.5440 (3)0.01600 (18)0.0569 (6)
C170.08801 (19)0.8058 (3)0.01468 (16)0.0528 (6)
H17A0.05520.77090.05020.063*
C160.1922 (2)0.8823 (3)0.05539 (18)0.0579 (6)
H16A0.22920.89830.01750.069*
C140.1883 (2)0.9135 (3)0.20763 (18)0.0596 (7)
H14A0.22160.95020.27220.072*
C150.2426 (2)0.9355 (3)0.15123 (19)0.0605 (7)
H15A0.31330.98620.17760.073*
C40.4449 (2)0.3949 (3)0.1372 (2)0.0664 (7)
H4A0.51050.33160.15370.080*
C30.3859 (2)0.4500 (4)0.0453 (2)0.0684 (8)
H3A0.41210.42640.00010.082*
C180.0262 (2)0.8130 (4)0.22658 (17)0.0624 (7)
C80.3432 (2)0.5053 (4)0.35194 (19)0.0716 (8)
H8A0.32180.53220.40010.086*
C70.4394 (2)0.4064 (4)0.3755 (2)0.0749 (8)
H7A0.48080.36470.43860.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0708 (12)0.1177 (17)0.0570 (11)0.0071 (11)0.0359 (10)0.0072 (11)
N10.0484 (11)0.0551 (12)0.0439 (11)0.0048 (9)0.0211 (9)0.0043 (9)
N20.0851 (17)0.134 (2)0.0598 (15)0.0022 (16)0.0421 (14)0.0019 (14)
C10.0461 (12)0.0447 (12)0.0530 (14)0.0078 (10)0.0259 (11)0.0084 (10)
C110.0498 (13)0.0447 (12)0.0473 (13)0.0059 (10)0.0256 (11)0.0057 (10)
C120.0428 (12)0.0450 (12)0.0449 (12)0.0070 (10)0.0205 (10)0.0072 (10)
C130.0498 (13)0.0542 (14)0.0475 (13)0.0075 (11)0.0232 (11)0.0025 (11)
C100.0461 (12)0.0406 (12)0.0559 (14)0.0069 (10)0.0224 (11)0.0025 (10)
C60.0505 (14)0.0529 (15)0.083 (2)0.0003 (12)0.0163 (15)0.0074 (14)
C50.0471 (13)0.0417 (12)0.0716 (17)0.0036 (11)0.0227 (13)0.0049 (12)
C90.0552 (14)0.0652 (16)0.0542 (15)0.0035 (12)0.0244 (12)0.0035 (12)
C20.0525 (14)0.0638 (16)0.0570 (15)0.0058 (12)0.0269 (12)0.0093 (12)
C170.0563 (14)0.0571 (15)0.0495 (13)0.0069 (12)0.0278 (11)0.0025 (11)
C160.0577 (15)0.0566 (15)0.0701 (17)0.0052 (12)0.0383 (13)0.0092 (13)
C140.0609 (15)0.0595 (15)0.0537 (15)0.0002 (12)0.0214 (13)0.0031 (12)
C150.0502 (14)0.0540 (15)0.0726 (18)0.0010 (11)0.0233 (13)0.0023 (13)
C40.0489 (14)0.0572 (16)0.092 (2)0.0015 (12)0.0304 (15)0.0130 (14)
C30.0612 (16)0.0731 (19)0.084 (2)0.0025 (14)0.0443 (15)0.0200 (15)
C180.0610 (15)0.0807 (19)0.0448 (14)0.0019 (14)0.0231 (12)0.0029 (13)
C80.0692 (17)0.085 (2)0.0578 (16)0.0000 (16)0.0261 (14)0.0081 (14)
C70.0678 (18)0.0729 (19)0.0686 (18)0.0019 (14)0.0169 (15)0.0185 (15)
Geometric parameters (Å, º) top
O1—C21.324 (3)C5—C41.423 (3)
O1—H1A0.8200C9—C81.368 (3)
N1—C111.296 (3)C9—H9A0.9300
N1—C121.412 (3)C2—C31.423 (3)
N2—C181.139 (3)C17—C161.377 (3)
C1—C21.412 (3)C17—H17A0.9300
C1—C111.426 (3)C16—C151.378 (3)
C1—C101.444 (3)C16—H16A0.9300
C11—H11A0.9300C14—C151.374 (3)
C12—C171.394 (3)C14—H14A0.9300
C12—C131.393 (3)C15—H15A0.9300
C13—C141.390 (3)C4—C31.340 (4)
C13—C181.439 (3)C4—H4A0.9300
C10—C91.414 (3)C3—H3A0.9300
C10—C51.423 (3)C8—C71.390 (4)
C6—C71.355 (4)C8—H8A0.9300
C6—C51.408 (3)C7—H7A0.9300
C6—H6A0.9300
C2—O1—H1A109.5O1—C2—C3117.6 (2)
C11—N1—C12123.63 (18)C1—C2—C3119.9 (2)
C2—C1—C11119.5 (2)C16—C17—C12119.8 (2)
C2—C1—C10118.8 (2)C16—C17—H17A120.1
C11—C1—C10121.64 (19)C12—C17—H17A120.1
N1—C11—C1122.3 (2)C15—C16—C17121.3 (2)
N1—C11—H11A118.8C15—C16—H16A119.4
C1—C11—H11A118.8C17—C16—H16A119.4
C17—C12—C13118.5 (2)C15—C14—C13119.6 (2)
C17—C12—N1124.8 (2)C15—C14—H14A120.2
C13—C12—N1116.66 (19)C13—C14—H14A120.2
C14—C13—C12121.0 (2)C14—C15—C16119.8 (2)
C14—C13—C18119.6 (2)C14—C15—H15A120.1
C12—C13—C18119.4 (2)C16—C15—H15A120.1
C9—C10—C5117.0 (2)C3—C4—C5122.0 (2)
C9—C10—C1123.3 (2)C3—C4—H4A119.0
C5—C10—C1119.6 (2)C5—C4—H4A119.0
C7—C6—C5120.9 (3)C4—C3—C2121.0 (2)
C7—C6—H6A119.6C4—C3—H3A119.5
C5—C6—H6A119.6C2—C3—H3A119.5
C6—C5—C4121.4 (2)N2—C18—C13179.3 (3)
C6—C5—C10120.0 (2)C9—C8—C7121.1 (3)
C4—C5—C10118.6 (2)C9—C8—H8A119.4
C8—C9—C10121.1 (2)C7—C8—H8A119.4
C8—C9—H9A119.5C6—C7—C8119.8 (3)
C10—C9—H9A119.5C6—C7—H7A120.1
O1—C2—C1122.4 (2)C8—C7—H7A120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.822.551 (2)147

Experimental details

Crystal data
Chemical formulaC18H12N2O
Mr272.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.4640 (13), 7.4450 (6), 15.4090 (11)
β (°) 116.660 (6)
V3)1380.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.973, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
12133, 2706, 1803
Rint0.056
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.159, 1.10
No. of reflections2706
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.822.551 (2)147.3
 

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