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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1926.
Published online 2008 September 13. doi:  10.1107/S1600536808028493
PMCID: PMC2959236

1-[(Pyrrolidin-1-yl)(p-tol­yl)meth­yl]naphthalen-2-ol

Abstract

In the title compound, C22H23NO, the dihedral angle between the naphthyl ring system and the benzene ring is 73.32 (6)°. An intra­molecular O—H(...)N hydrogen bond stabilizes the mol­ecular conformation. In the crystal structure, mol­ecules are linked by C—H(...)π inter­actions, resulting in zigzag chains parallel to the [10An external file that holds a picture, illustration, etc.
Object name is e-64-o1926-efi1.jpg] direction.

Related literature

For general background on the chemistry of naphthalen-2-ol derivatives, see: Szatmari & Fulop (2004 [triangle]); Zhao & Sun (2005 [triangle]). For puckering and asymmetry parameters, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1926-scheme1.jpg

Experimental

Crystal data

  • C22H23NO
  • M r = 317.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1926-efi2.jpg
  • a = 10.3467 (18) Å
  • b = 16.055 (3) Å
  • c = 11.252 (2) Å
  • β = 106.810 (8)°
  • V = 1789.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 (2) K
  • 0.25 × 0.22 × 0.20 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.963, T max = 0.989
  • 18171 measured reflections
  • 4086 independent reflections
  • 2547 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.190
  • S = 1.06
  • 4086 reflections
  • 219 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.20 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/S1600536808028493/rz2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028493/rz2244Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Southeast University to HZ.

supplementary crystallographic information

Comment

Compounds derived from naphthalen-2-ol have been of great interest in organic chemistry (Szatmari & Fulop, 2004; Zhao & Sun, 2005). We report here the crystal structure of the title compound (Fig. 1).

Bond lengths and angles in the title compound have normal values. The dihedral angle between the naphthyl and phenyl rings is 73.32 (6)°. The pyrrolidine ring adopts a twist conformation, as indicated by the puckering parameters (q2 = 0.401 (2) Å and [var phi] = 169.2 (4)°; Cremer & Pople, 1975) and the small value of the displacement asymmetry parameter (ΔC2(C14) = 0.0301 (10)°; Nardelli, 1983). The molecular conformation is stabilized by a strong intramolecular O—H···N hydrogen bond (Table 1). In the crystal packing, molecules are linked through C—H···π interactions (Table 1) to form zig zag chains running along the [1 0 -1] direction.

Experimental

A dry 50 ml flask was charged with benzaldehyde (10 mmol), naphthalen-2-ol (10 mmol), and pyrrolidine (10 mmol). The mixture was stirred at 100°C for 10 h then ethanol (15 ml) was added. After heating under reflux for 30 minutes, the precipitate was filtrated off and washed 3 times with ethanol to give the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane solution.

Refinement

All hydrogen atoms were calculated geometrically, with C—H = 0.93-0.98 Å, O—H= 0.82 Å, and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.2Ueq(C, O) for methyl and hydroxy hydrogen atoms.

Figures

Fig. 1.
The structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular O—H···N hydrogen bond is indicated by a dashed line.

Crystal data

C22H23NOF(000) = 680
Mr = 317.41Dx = 1.178 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3280 reflections
a = 10.3467 (18) Åθ = 2.3–27.4°
b = 16.055 (3) ŵ = 0.07 mm1
c = 11.252 (2) ÅT = 293 K
β = 106.810 (8)°Prism, colourless
V = 1789.2 (6) Å30.25 × 0.22 × 0.20 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer4086 independent reflections
Radiation source: fine-focus sealed tube2547 reflections with I > 2σ(I)
graphiteRint = 0.058
Detector resolution: 13.6612 pixels mm-1θmax = 27.4°, θmin = 2.3°
ω scansh = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −20→20
Tmin = 0.963, Tmax = 0.989l = −14→14
18171 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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0911P)2 + 0.1709P] where P = (Fo2 + 2Fc2)/3
4086 reflections(Δ/σ)max = 0.005
219 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

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)

xyzUiso*/Ueq
C10.2106 (2)0.17738 (14)0.94453 (19)0.0419 (5)
C20.2318 (2)0.10314 (14)1.0087 (2)0.0484 (6)
C30.3641 (2)0.07349 (17)1.0645 (2)0.0593 (7)
H30.37620.02251.10560.071*
C40.4730 (2)0.11799 (18)1.0592 (2)0.0603 (7)
H40.55910.09701.09590.072*
C50.4578 (2)0.19606 (16)0.9986 (2)0.0511 (6)
C60.3253 (2)0.22609 (14)0.9413 (2)0.0437 (5)
C70.3143 (2)0.30541 (15)0.8828 (2)0.0526 (6)
H70.22920.32760.84550.063*
C80.4263 (3)0.34974 (18)0.8801 (3)0.0680 (8)
H80.41610.40140.84100.082*
C90.5550 (3)0.3189 (2)0.9349 (3)0.0713 (8)
H90.63020.34950.93170.086*
C100.5714 (2)0.2439 (2)0.9932 (3)0.0654 (8)
H100.65790.22361.02990.078*
C110.0689 (2)0.20844 (12)0.87783 (19)0.0396 (5)
H110.07380.23880.80370.048*
C120.0091 (2)0.08850 (15)0.7372 (2)0.0512 (6)
H12A0.08860.05440.77100.061*
H12B0.02480.12490.67400.061*
C13−0.1145 (2)0.03501 (16)0.6848 (2)0.0603 (7)
H13A−0.1071−0.01710.72980.072*
H13B−0.12690.02310.59770.072*
C14−0.2303 (2)0.08716 (16)0.7016 (3)0.0617 (7)
H14A−0.28310.05550.74450.074*
H14B−0.28900.10480.62180.074*
C15−0.1655 (2)0.16206 (16)0.7785 (2)0.0563 (7)
H15A−0.17040.21070.72630.068*
H15B−0.20980.17450.84150.068*
C160.01458 (19)0.26802 (13)0.95666 (19)0.0395 (5)
C170.0117 (2)0.24824 (14)1.0757 (2)0.0477 (5)
H170.04540.19721.11000.057*
C18−0.0407 (2)0.30347 (15)1.1441 (2)0.0528 (6)
H18−0.04280.28841.22330.063*
C19−0.0899 (2)0.38058 (15)1.0975 (2)0.0479 (6)
C20−0.0865 (2)0.39997 (14)0.9788 (2)0.0493 (6)
H20−0.11890.45140.94500.059*
C21−0.0361 (2)0.34482 (14)0.9096 (2)0.0458 (5)
H21−0.03620.35950.82960.055*
C22−0.1439 (3)0.44099 (18)1.1736 (3)0.0712 (8)
H22A−0.12900.41931.25600.107*
H22B−0.23890.44881.13580.107*
H22C−0.09820.49341.17760.107*
N1−0.02391 (16)0.13698 (11)0.83579 (16)0.0414 (4)
O10.13049 (17)0.05359 (11)1.02090 (17)0.0641 (5)
H10.05850.07000.97440.096*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0345 (11)0.0496 (13)0.0407 (12)−0.0007 (9)0.0094 (9)−0.0015 (9)
C20.0431 (12)0.0535 (14)0.0463 (13)−0.0024 (10)0.0091 (10)0.0064 (10)
C30.0518 (14)0.0671 (17)0.0532 (15)0.0093 (13)0.0057 (12)0.0106 (12)
C40.0392 (12)0.0837 (19)0.0513 (15)0.0098 (12)0.0024 (11)−0.0049 (13)
C50.0368 (11)0.0684 (16)0.0465 (13)−0.0041 (11)0.0097 (10)−0.0150 (11)
C60.0373 (11)0.0525 (13)0.0425 (12)−0.0048 (9)0.0135 (9)−0.0096 (10)
C70.0464 (13)0.0510 (14)0.0629 (16)−0.0094 (11)0.0197 (11)−0.0057 (11)
C80.0629 (17)0.0617 (17)0.086 (2)−0.0203 (13)0.0317 (15)−0.0078 (14)
C90.0527 (16)0.085 (2)0.081 (2)−0.0297 (15)0.0271 (15)−0.0208 (16)
C100.0368 (12)0.094 (2)0.0635 (17)−0.0096 (13)0.0123 (12)−0.0234 (15)
C110.0361 (10)0.0415 (12)0.0407 (12)−0.0038 (9)0.0103 (9)0.0045 (9)
C120.0431 (12)0.0561 (15)0.0543 (14)−0.0004 (10)0.0143 (11)−0.0072 (11)
C130.0517 (14)0.0602 (16)0.0629 (16)−0.0037 (12)0.0070 (12)−0.0137 (12)
C140.0407 (12)0.0626 (16)0.0748 (18)−0.0043 (11)0.0055 (12)−0.0118 (13)
C150.0343 (12)0.0621 (16)0.0671 (16)0.0008 (10)0.0062 (11)−0.0113 (12)
C160.0313 (10)0.0451 (12)0.0409 (12)−0.0050 (9)0.0086 (9)0.0021 (9)
C170.0527 (13)0.0446 (13)0.0473 (13)0.0006 (10)0.0168 (11)0.0070 (10)
C180.0560 (14)0.0626 (16)0.0433 (13)−0.0062 (12)0.0198 (11)0.0010 (11)
C190.0335 (11)0.0544 (14)0.0543 (15)−0.0033 (10)0.0105 (10)−0.0063 (11)
C200.0415 (12)0.0446 (13)0.0584 (15)0.0059 (10)0.0088 (11)0.0044 (10)
C210.0411 (11)0.0499 (14)0.0440 (13)0.0009 (10)0.0085 (10)0.0067 (10)
C220.0627 (17)0.077 (2)0.0782 (19)0.0021 (14)0.0275 (15)−0.0171 (15)
N10.0309 (9)0.0458 (10)0.0463 (11)−0.0024 (7)0.0093 (8)−0.0028 (8)
O10.0508 (10)0.0634 (12)0.0733 (13)−0.0053 (8)0.0102 (9)0.0243 (9)

Geometric parameters (Å, °)

C1—C21.378 (3)C12—H12B0.9700
C1—C61.430 (3)C13—C141.518 (3)
C1—C111.525 (3)C13—H13A0.9700
C2—O11.354 (3)C13—H13B0.9700
C2—C31.413 (3)C14—C151.519 (3)
C3—C41.351 (4)C14—H14A0.9700
C3—H30.9300C14—H14B0.9700
C4—C51.414 (4)C15—N11.476 (3)
C4—H40.9300C15—H15A0.9700
C5—C101.420 (3)C15—H15B0.9700
C5—C61.420 (3)C16—C211.384 (3)
C6—C71.423 (3)C16—C171.385 (3)
C7—C81.367 (3)C17—C181.383 (3)
C7—H70.9300C17—H170.9300
C8—C91.387 (4)C18—C191.383 (3)
C8—H80.9300C18—H180.9300
C9—C101.357 (4)C19—C201.381 (3)
C9—H90.9300C19—C221.504 (3)
C10—H100.9300C20—C211.378 (3)
C11—N11.483 (2)C20—H200.9300
C11—C161.518 (3)C21—H210.9300
C11—H110.9800C22—H22A0.9600
C12—N11.474 (3)C22—H22B0.9600
C12—C131.511 (3)C22—H22C0.9600
C12—H12A0.9700O1—H10.8200
C2—C1—C6118.6 (2)C14—C13—H13A110.9
C2—C1—C11121.71 (19)C12—C13—H13B110.9
C6—C1—C11119.71 (19)C14—C13—H13B110.9
O1—C2—C1123.4 (2)H13A—C13—H13B108.9
O1—C2—C3115.8 (2)C13—C14—C15105.88 (19)
C1—C2—C3120.8 (2)C13—C14—H14A110.6
C4—C3—C2121.0 (2)C15—C14—H14A110.6
C4—C3—H3119.5C13—C14—H14B110.6
C2—C3—H3119.5C15—C14—H14B110.6
C3—C4—C5120.8 (2)H14A—C14—H14B108.7
C3—C4—H4119.6N1—C15—C14104.57 (18)
C5—C4—H4119.6N1—C15—H15A110.8
C4—C5—C10121.5 (2)C14—C15—H15A110.8
C4—C5—C6118.6 (2)N1—C15—H15B110.8
C10—C5—C6120.0 (3)C14—C15—H15B110.8
C5—C6—C7116.8 (2)H15A—C15—H15B108.9
C5—C6—C1120.2 (2)C21—C16—C17117.6 (2)
C7—C6—C1123.0 (2)C21—C16—C11120.06 (19)
C8—C7—C6121.4 (2)C17—C16—C11122.37 (19)
C8—C7—H7119.3C18—C17—C16120.8 (2)
C6—C7—H7119.3C18—C17—H17119.6
C7—C8—C9121.0 (3)C16—C17—H17119.6
C7—C8—H8119.5C19—C18—C17121.6 (2)
C9—C8—H8119.5C19—C18—H18119.2
C10—C9—C8120.1 (2)C17—C18—H18119.2
C10—C9—H9120.0C20—C19—C18117.3 (2)
C8—C9—H9120.0C20—C19—C22121.5 (2)
C9—C10—C5120.7 (3)C18—C19—C22121.2 (2)
C9—C10—H10119.6C21—C20—C19121.4 (2)
C5—C10—H10119.6C21—C20—H20119.3
N1—C11—C16111.04 (16)C19—C20—H20119.3
N1—C11—C1110.22 (16)C20—C21—C16121.3 (2)
C16—C11—C1112.58 (17)C20—C21—H21119.4
N1—C11—H11107.6C16—C21—H21119.4
C16—C11—H11107.6C19—C22—H22A109.5
C1—C11—H11107.6C19—C22—H22B109.5
N1—C12—C13103.87 (18)H22A—C22—H22B109.5
N1—C12—H12A111.0C19—C22—H22C109.5
C13—C12—H12A111.0H22A—C22—H22C109.5
N1—C12—H12B111.0H22B—C22—H22C109.5
C13—C12—H12B111.0C12—N1—C15103.41 (17)
H12A—C12—H12B109.0C12—N1—C11112.27 (16)
C12—C13—C14104.3 (2)C15—N1—C11113.43 (17)
C12—C13—H13A110.9C2—O1—H1109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.600 (3)145
C18—H18···Cg1i0.932.663.588 (8)173

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2244).

References

  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Nardelli, M. (1983). Acta Cryst. C39, 1141–1142.
  • 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.
  • Zhao, B. & Sun, Y.-X. (2005). Acta Cryst. E61, m652–m653.

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