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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2938.
Published online 2010 October 23. doi:  10.1107/S1600536810042327
PMCID: PMC3009335

1-[Phen­yl(pyridin-2-yl­amino)­meth­yl]-2-naphthol

Abstract

The title compound, C22H18N2O, was synthesized from naphthalen-2-ol, benzaldehyde and pyridin-2-amine. In the crystal, mol­ecules are linked into centrosymmetric R 2 2(16) dimers by pairs of O—H(...)N hydrogen bonds. The mol­ecular conformation is stabilized by an N—H(...)O hydrogen bond. The dihedral angle between the naphthylene ring system and the phenyl ring is 72.86 (12)°.

Related literature

For the application of compounds derived from naphthalen-2-ol in catalytic asymmetric synthesis, see: Szatmari & Fulop (2004 [triangle]). For related structures, see: Wang & Zhao (2009 [triangle]); Zhao & Sun (2005 [triangle]). For graph-set motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-66-o2938-scheme1.jpg

Experimental

Crystal data

  • C22H18N2O
  • M r = 326.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2938-efi1.jpg
  • a = 7.5841 (10) Å
  • b = 10.1890 (15) Å
  • c = 11.9745 (15) Å
  • α = 111.00 (3)°
  • β = 98.64 (5)°
  • γ = 90.83 (3)°
  • V = 851.7 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.18 × 0.15 × 0.12 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.982, T max = 0.990
  • 8701 measured reflections
  • 3841 independent reflections
  • 1655 reflections with I > 2σ(I)
  • R int = 0.078

Refinement

  • R[F 2 > 2σ(F 2)] = 0.097
  • wR(F 2) = 0.218
  • S = 1.10
  • 3841 reflections
  • 230 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL/PC (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL/PC.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042327/bx2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042327/bx2316Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported financially by Southeast University for Young Researchers (4007041027).

supplementary crystallographic information

Comment

Compounds derived from naphthalen-2-ol have been of great interest in organic chemistry due to their application in catalytic asymmetric synthesis (Szatmari & Fulop, 2004; Zhao & Sun, 2005). As an extension of our work on the structural characterization of naphthol compounds (Wang & Zhao, 2009), we report here the structure of the title compound. In the title compound (Fig. 1) bond lengths and angles have normal values. The dihedral angle between the naphthylene ring system and the benzene ring is 72.86 (12)°, and the pyridine ring is 72.61 (11)° respectively. The dihedral angle between benzene ring and the pyridine ring is 74.80 (13)°. In the solid state the molecules are linked into centrosymmetric R22 (16) dimers by a simple O—H···N interaction, (Bernstein et al., 1995), (Fig. 2). The molecular conformation is stabilized by one N—H···O hydrogen bonding, Table 1.

Experimental

A dry 50 ml flask was charged with benzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and pyridin-2-amine (10 mmol). The mixture was stirred at 100°C for 12 h and then added ethanol (15 ml), after heated under reflux for 1 h, the precipitate was filtrated out and washed with ethanol for 3 times to give the title compound. Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution.

Refinement

All H atoms were detected in a difference map, the H-atom bonded to C1 was refined freely, but all other H-atoms were placed in calculated positions and refined using a riding motion approxmation, with C—H = 0.93–0.98 Å, with Uiso(H) = 1.2Ueq(C); O—H = 0.82 Å, with Uiso(H) = 1.5Ueq(O); N—H = 0.86 Å, with Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Diagram of the molecules linked into centrosymmetric R22 (16) dimers by a simple O—H···N interaction .The H atoms not involved in hydrogen bonding have been omitted. The atoms no-labelled are related with labelled atoms ...

Crystal data

C22H18N2OZ = 2
Mr = 326.38F(000) = 344
Triclinic, P1Dx = 1.273 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5841 (10) ÅCell parameters from 1326 reflections
b = 10.1890 (15) Åθ = 2.7–27.4°
c = 11.9745 (15) ŵ = 0.08 mm1
α = 111.00 (3)°T = 295 K
β = 98.64 (5)°Prism, colourless
γ = 90.83 (3)°0.18 × 0.15 × 0.12 mm
V = 851.7 (2) Å3

Data collection

Rigaku SCXmini diffractometer3841 independent reflections
Radiation source: fine-focus sealed tube1655 reflections with I > 2σ(I)
graphiteRint = 0.078
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.7°
CCD_Profile_fitting scansh = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −13→13
Tmin = 0.982, Tmax = 0.990l = −15→15
8701 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.097Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218H atoms treated by a mixture of independent and constrained refinement
S = 1.10w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
3841 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
O11.0666 (3)0.3873 (3)0.8523 (2)0.0617 (8)
H1A1.14140.45230.86580.093*
N10.7935 (4)0.2729 (3)0.9263 (3)0.0566 (9)
H1B0.89640.30930.96820.068*
N20.6664 (4)0.4120 (3)1.0857 (3)0.0530 (8)
C10.7861 (5)0.1892 (4)0.7972 (3)0.0485 (9)
C20.7985 (5)0.2805 (4)0.7231 (3)0.0470 (9)
C30.9439 (5)0.3761 (4)0.7531 (3)0.0520 (10)
C40.9660 (6)0.4595 (4)0.6832 (4)0.0642 (11)
H41.06590.52280.70410.077*
C50.8400 (6)0.4467 (5)0.5847 (4)0.0700 (12)
H50.85590.50090.53840.084*
C60.6862 (6)0.3526 (4)0.5520 (3)0.0604 (11)
C70.6633 (5)0.2706 (4)0.6231 (3)0.0545 (10)
C80.5032 (6)0.1824 (4)0.5882 (4)0.0720 (13)
H80.48220.12760.63310.086*
C90.3793 (7)0.1749 (5)0.4913 (5)0.0960 (17)
H90.27510.11650.47180.115*
C100.4070 (8)0.2538 (6)0.4213 (5)0.0990 (19)
H100.32220.24670.35420.119*
C110.5562 (7)0.3408 (5)0.4499 (4)0.0817 (14)
H110.57400.39320.40240.098*
C120.9204 (5)0.0761 (4)0.7796 (3)0.0488 (9)
C130.9214 (6)−0.0125 (4)0.8453 (3)0.0650 (11)
H130.84390.00070.90100.078*
C141.0357 (7)−0.1196 (5)0.8290 (4)0.0769 (13)
H141.0342−0.17830.87320.092*
C151.1510 (6)−0.1395 (5)0.7479 (4)0.0793 (13)
H151.2311−0.20940.73880.095*
C161.1481 (6)−0.0558 (4)0.6801 (4)0.0739 (13)
H161.2231−0.07180.62260.089*
C171.0346 (5)0.0526 (4)0.6962 (3)0.0607 (11)
H171.03550.10960.65060.073*
C180.6481 (5)0.2977 (4)0.9857 (3)0.0476 (9)
C190.4937 (5)0.2068 (4)0.9475 (4)0.0648 (12)
H190.48290.12540.87840.078*
C200.3584 (6)0.2405 (5)1.0143 (4)0.0775 (13)
H200.25350.18200.98900.093*
C210.3736 (6)0.3571 (5)1.1164 (4)0.0780 (13)
H210.28240.38021.16250.094*
C220.5309 (6)0.4390 (5)1.1480 (4)0.0689 (12)
H220.54430.51951.21810.083*
H660.668 (4)0.142 (3)0.776 (3)0.041 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0546 (17)0.0668 (18)0.0604 (17)−0.0142 (13)−0.0016 (13)0.0244 (15)
N10.0449 (19)0.068 (2)0.0469 (18)−0.0050 (15)0.0048 (14)0.0102 (17)
N20.054 (2)0.053 (2)0.0499 (18)0.0025 (15)0.0178 (15)0.0124 (17)
C10.043 (2)0.050 (2)0.046 (2)−0.0056 (18)0.0043 (17)0.0101 (19)
C20.054 (2)0.042 (2)0.043 (2)0.0036 (18)0.0096 (17)0.0126 (18)
C30.050 (2)0.056 (2)0.050 (2)0.0035 (19)0.0076 (19)0.019 (2)
C40.068 (3)0.061 (3)0.070 (3)0.006 (2)0.021 (2)0.028 (2)
C50.087 (3)0.074 (3)0.063 (3)0.027 (3)0.021 (2)0.038 (3)
C60.066 (3)0.054 (3)0.052 (2)0.018 (2)0.007 (2)0.010 (2)
C70.062 (3)0.047 (2)0.048 (2)0.0171 (19)0.0106 (19)0.009 (2)
C80.062 (3)0.061 (3)0.077 (3)0.000 (2)−0.012 (2)0.016 (2)
C90.085 (4)0.076 (3)0.102 (4)−0.002 (3)−0.030 (3)0.020 (3)
C100.110 (5)0.081 (4)0.072 (3)0.024 (3)−0.030 (3)0.005 (3)
C110.102 (4)0.080 (3)0.058 (3)0.037 (3)0.003 (3)0.022 (3)
C120.050 (2)0.050 (2)0.041 (2)−0.0084 (17)0.0033 (17)0.0112 (19)
C130.078 (3)0.060 (3)0.058 (3)−0.003 (2)0.012 (2)0.023 (2)
C140.106 (4)0.056 (3)0.075 (3)0.015 (3)0.015 (3)0.032 (3)
C150.085 (4)0.064 (3)0.089 (3)0.017 (2)0.022 (3)0.024 (3)
C160.086 (3)0.053 (3)0.085 (3)0.011 (2)0.033 (3)0.019 (3)
C170.070 (3)0.054 (3)0.060 (2)0.006 (2)0.019 (2)0.020 (2)
C180.046 (2)0.051 (2)0.048 (2)−0.0019 (17)0.0073 (17)0.020 (2)
C190.060 (3)0.064 (3)0.057 (2)−0.010 (2)0.013 (2)0.006 (2)
C200.054 (3)0.096 (4)0.083 (3)−0.010 (2)0.017 (2)0.032 (3)
C210.063 (3)0.096 (4)0.078 (3)0.009 (3)0.033 (2)0.027 (3)
C220.072 (3)0.066 (3)0.064 (3)0.009 (2)0.024 (2)0.013 (2)

Geometric parameters (Å, °)

O1—C31.363 (4)C9—H90.9300
O1—H1A0.8194C10—C111.349 (7)
N1—C181.378 (4)C10—H100.9300
N1—C11.466 (4)C11—H110.9300
N1—H1B0.8596C12—C171.378 (5)
N2—C181.325 (4)C12—C131.393 (5)
N2—C221.335 (5)C13—C141.381 (6)
C1—C21.508 (5)C13—H130.9300
C1—C121.528 (5)C14—C151.366 (6)
C1—H660.97 (3)C14—H140.9300
C2—C31.376 (5)C15—C161.371 (6)
C2—C71.427 (5)C15—H150.9300
C3—C41.415 (5)C16—C171.386 (5)
C4—C51.367 (5)C16—H160.9300
C4—H40.9300C17—H170.9300
C5—C61.413 (6)C18—C191.394 (5)
C5—H50.9300C19—C201.368 (5)
C6—C71.416 (5)C19—H190.9300
C6—C111.418 (5)C20—C211.354 (6)
C7—C81.415 (5)C20—H200.9300
C8—C91.357 (6)C21—C221.368 (6)
C8—H80.9300C21—H210.9300
C9—C101.388 (7)C22—H220.9300
C3—O1—H1A109.5C9—C10—H10119.8
C18—N1—C1125.0 (3)C10—C11—C6120.3 (5)
C18—N1—H1B117.5C10—C11—H11119.9
C1—N1—H1B117.5C6—C11—H11119.9
C18—N2—C22117.9 (3)C17—C12—C13118.2 (4)
N1—C1—C2112.2 (3)C17—C12—C1122.6 (3)
N1—C1—C12110.8 (3)C13—C12—C1119.0 (3)
C2—C1—C12114.6 (3)C14—C13—C12121.1 (4)
N1—C1—H66102.0 (18)C14—C13—H13119.5
C2—C1—H66109.0 (18)C12—C13—H13119.5
C12—C1—H66107.4 (19)C15—C14—C13120.0 (4)
C3—C2—C7119.2 (3)C15—C14—H14120.0
C3—C2—C1119.0 (3)C13—C14—H14120.0
C7—C2—C1121.7 (3)C14—C15—C16119.6 (4)
O1—C3—C2117.8 (3)C14—C15—H15120.2
O1—C3—C4121.0 (3)C16—C15—H15120.2
C2—C3—C4121.2 (4)C15—C16—C17120.8 (4)
C5—C4—C3119.7 (4)C15—C16—H16119.6
C5—C4—H4120.2C17—C16—H16119.6
C3—C4—H4120.2C12—C17—C16120.2 (4)
C4—C5—C6121.2 (4)C12—C17—H17119.9
C4—C5—H5119.4C16—C17—H17119.9
C6—C5—H5119.4N2—C18—N1115.6 (3)
C5—C6—C7119.0 (4)N2—C18—C19121.3 (3)
C5—C6—C11120.6 (4)N1—C18—C19123.1 (4)
C7—C6—C11120.4 (4)C20—C19—C18118.2 (4)
C8—C7—C6116.1 (4)C20—C19—H19120.9
C8—C7—C2124.3 (4)C18—C19—H19120.9
C6—C7—C2119.6 (4)C21—C20—C19121.5 (4)
C9—C8—C7122.3 (5)C21—C20—H20119.2
C9—C8—H8118.9C19—C20—H20119.2
C7—C8—H8118.9C20—C21—C22116.2 (4)
C8—C9—C10120.5 (5)C20—C21—H21121.9
C8—C9—H9119.8C22—C21—H21121.9
C10—C9—H9119.8N2—C22—C21124.8 (4)
C11—C10—C9120.4 (5)N2—C22—H22117.6
C11—C10—H10119.8C21—C22—H22117.6
C18—N1—C1—C2102.8 (4)C8—C9—C10—C11−1.1 (8)
C18—N1—C1—C12−127.8 (4)C9—C10—C11—C6−0.1 (8)
N1—C1—C2—C356.8 (4)C5—C6—C11—C10−178.0 (5)
C12—C1—C2—C3−70.6 (4)C7—C6—C11—C101.7 (6)
N1—C1—C2—C7−122.9 (4)N1—C1—C12—C17−132.7 (4)
C12—C1—C2—C7109.6 (4)C2—C1—C12—C17−4.6 (5)
C7—C2—C3—O1177.1 (3)N1—C1—C12—C1351.0 (4)
C1—C2—C3—O1−2.7 (5)C2—C1—C12—C13179.1 (3)
C7—C2—C3—C4−3.2 (5)C17—C12—C13—C141.1 (6)
C1—C2—C3—C4177.1 (3)C1—C12—C13—C14177.5 (4)
O1—C3—C4—C5−179.5 (3)C12—C13—C14—C150.4 (7)
C2—C3—C4—C50.8 (6)C13—C14—C15—C16−2.3 (7)
C3—C4—C5—C60.8 (6)C14—C15—C16—C172.6 (7)
C4—C5—C6—C70.1 (6)C13—C12—C17—C16−0.7 (6)
C4—C5—C6—C11179.8 (4)C1—C12—C17—C16−177.0 (3)
C5—C6—C7—C8177.7 (4)C15—C16—C17—C12−1.1 (6)
C11—C6—C7—C8−2.0 (5)C22—N2—C18—N1−178.6 (3)
C5—C6—C7—C2−2.4 (5)C22—N2—C18—C19−1.1 (5)
C11—C6—C7—C2177.9 (4)C1—N1—C18—N2−156.4 (3)
C3—C2—C7—C8−176.2 (4)C1—N1—C18—C1926.2 (6)
C1—C2—C7—C83.6 (6)N2—C18—C19—C201.7 (6)
C3—C2—C7—C64.0 (5)N1—C18—C19—C20179.0 (4)
C1—C2—C7—C6−176.3 (3)C18—C19—C20—C21−1.4 (7)
C6—C7—C8—C90.8 (6)C19—C20—C21—C220.4 (7)
C2—C7—C8—C9−179.1 (4)C18—N2—C22—C210.1 (6)
C7—C8—C9—C100.7 (7)C20—C21—C22—N20.3 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N2i0.821.872.677 (4)170
N1—H1B···O10.862.352.767 (4)110

Symmetry codes: (i) −x+2, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2316).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555-1573.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Szatmari, I. & Fulop, F. (2004). Curr. Org. Synth.1, 155–165.
  • Wang, W. X. & Zhao, H. (2009). Acta Cryst. E65, o1277. [PMC free article] [PubMed]
  • Zhao, B. & Sun, Y.-X. (2005). Acta Cryst. E61, m652–m653.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography