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Acta Cryst. (2009). E65, o1277    [ doi:10.1107/S1600536809017176 ]

1-[(3-Methylpiperidin-1-yl)(phenyl)methyl]-2-naphthol

W. X. Wang and H. Zhao

Abstract top

In the title compound, C23H25NO, the dihedral angle between the naphthylene ring system and the benzene ring is 78.17 (10)°. The molecular conformation is stabilized by a strong intramolecular O-H...N hydrogen bond.

Comment top

It is well known that many compounds derived from naphthalen-2-ol have received much attention in organic chemistry (Szatmari & Fulop, 2004; Zhao & Sun, 2005). Recently, we reported the synthesis and crystal structures of 1-[(dimethylamino)(phenyl)methyl]naphthalen-2-ol (Wang & Zhao, 2008) and 1-[pyrrolidin-1-yl(p-tolyl)methyl]naphthalen-2-ol (Wan & Zhao, 2008). We now report the crystal structure of the title compound.

Bond lengths and angles in the title compound have normal values. The dihedral angle between the naphthyl and phenyl rings is 78.17 (10)°. The molecular conformation is stabilized by a strong intramolecular O—H···N hydrogen bond (Table 1). The crystal packing is mainly stabilized by van der Waals interactions.

Related literature top

For the structures of related compounds, see: Szatmari & Fulop (2004); Zhao & Sun (2005); Wang & Zhao (2008); Wan & Zhao (2008).

Experimental top

A dry 50 ml flask was charged with benzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and 3-methylpiperidine (10 mmol). The mixture was stirred at 373 K for 10 h, then ethanol (15 ml) was added. After heating under reflux for 30 min, 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 top

All H 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 Y atoms.

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/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
1-[(3-methylpiperidin-1-yl)(phenyl)methyl]-2-naphthol top
Crystal data top
C23H25NOF000 = 712
Mr = 331.44Dx = 1.185 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2989 reflections
a = 9.2138 (13) Åθ = 2.6–27.9º
b = 10.9056 (13) ŵ = 0.07 mm−1
c = 18.635 (3) ÅT = 292 K
β = 97.007 (10)ºPrism, pale yellow
V = 1858.5 (5) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer		4422 independent reflections
Radiation source: fine-focus sealed tube2302 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.067
Detector resolution: 13.6612 pixels mm-1θmax = 27.9º
T = 292 Kθmin = 2.9º
ω scansh = −12→12
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −14→14
Tmin = 0.965, Tmax = 0.979l = −24→24
19217 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.155  w = 1/[σ2(Fo2) + (0.0693P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
4422 reflectionsΔρmax = 0.15 e Å−3
228 parametersΔρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C23H25NOV = 1858.5 (5) Å3
Mr = 331.44Z = 4
Monoclinic, P21/nMo Kα
a = 9.2138 (13) ŵ = 0.07 mm−1
b = 10.9056 (13) ÅT = 292 K
c = 18.635 (3) Å0.30 × 0.25 × 0.20 mm
β = 97.007 (10)º
Data collection top
Rigaku SCXmini
diffractometer		4422 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2302 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.979Rint = 0.067
19217 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.061228 parameters
wR(F2) = 0.155H-atom parameters constrained
S = 0.99Δρmax = 0.15 e Å−3
4422 reflectionsΔρmin = −0.16 e Å−3
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
C10.67985 (19)0.98342 (18)0.20764 (10)0.0429 (5)
H10.64431.06440.22030.051*
C20.78426 (19)0.93769 (17)0.27180 (10)0.0424 (5)
C30.9016 (2)0.86366 (18)0.26209 (11)0.0473 (5)
C40.9972 (2)0.8201 (2)0.32150 (13)0.0588 (6)
H41.07780.77280.31380.071*
C50.9718 (2)0.8470 (2)0.38980 (13)0.0640 (6)
H51.03490.81680.42850.077*
C60.8527 (2)0.9195 (2)0.40364 (11)0.0560 (6)
C70.7590 (2)0.96718 (17)0.34408 (10)0.0466 (5)
C80.6424 (2)1.04328 (19)0.36039 (12)0.0580 (6)
H80.57901.07640.32270.070*
C90.6211 (3)1.0690 (2)0.42986 (13)0.0739 (7)
H90.54451.12010.43880.089*
C100.7124 (3)1.0197 (3)0.48762 (14)0.0845 (9)
H100.69591.03670.53490.101*
C110.8255 (3)0.9467 (2)0.47479 (12)0.0724 (7)
H110.88630.91390.51360.087*
C120.5482 (2)0.89924 (19)0.19333 (10)0.0466 (5)
C130.4093 (2)0.9444 (2)0.19799 (11)0.0601 (6)
H130.39731.02670.20900.072*
C140.2885 (2)0.8692 (3)0.18655 (13)0.0719 (7)
H140.19590.90080.19010.086*
C150.3047 (3)0.7479 (3)0.16990 (13)0.0713 (7)
H150.22310.69720.16200.086*
C160.4413 (2)0.7016 (2)0.16489 (11)0.0655 (6)
H160.45240.61930.15360.079*
C170.5626 (2)0.7767 (2)0.17657 (11)0.0541 (5)
H170.65500.74440.17310.065*
C180.6619 (2)1.0167 (2)0.07506 (10)0.0580 (6)
H18A0.60421.09040.07840.070*
H18B0.59540.94770.06710.070*
C190.7514 (2)1.0277 (2)0.01231 (11)0.0680 (7)
H19A0.80240.95110.00680.082*
H19B0.68641.0421−0.03180.082*
C200.8616 (2)1.1307 (2)0.02313 (11)0.0634 (6)
H20A0.81061.20870.02160.076*
H20B0.92251.1298−0.01580.076*
C210.9571 (2)1.11783 (19)0.09503 (11)0.0531 (5)
H211.01521.04280.09350.064*
C220.8604 (2)1.10436 (19)0.15507 (11)0.0509 (5)
H22A0.92171.09400.20080.061*
H22B0.80381.17880.15800.061*
C231.0612 (3)1.2248 (2)0.11110 (14)0.0819 (8)
H23A1.00641.29960.11130.123*
H23B1.12621.22930.07460.123*
H23C1.11711.21320.15760.123*
N10.75966 (16)0.99877 (14)0.14314 (8)0.0455 (4)
O10.93357 (14)0.82835 (13)0.19587 (8)0.0575 (4)
H1A0.88510.86900.16460.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0391 (10)0.0487 (11)0.0419 (11)0.0029 (9)0.0094 (8)−0.0008 (9)
C20.0363 (10)0.0451 (10)0.0454 (11)−0.0067 (9)0.0030 (8)−0.0013 (9)
C30.0389 (11)0.0505 (12)0.0522 (13)−0.0056 (9)0.0047 (9)−0.0016 (10)
C40.0405 (11)0.0570 (13)0.0758 (17)−0.0008 (10)−0.0054 (11)0.0039 (12)
C50.0608 (15)0.0662 (15)0.0594 (16)−0.0155 (13)−0.0149 (11)0.0122 (12)
C60.0570 (13)0.0584 (14)0.0507 (13)−0.0203 (12)−0.0008 (10)0.0018 (11)
C70.0485 (12)0.0482 (11)0.0435 (12)−0.0139 (10)0.0070 (9)−0.0010 (9)
C80.0602 (14)0.0652 (14)0.0513 (13)−0.0089 (12)0.0177 (10)−0.0074 (11)
C90.0778 (17)0.0849 (18)0.0635 (17)−0.0153 (15)0.0265 (14)−0.0185 (14)
C100.100 (2)0.105 (2)0.0508 (16)−0.0353 (18)0.0194 (15)−0.0203 (15)
C110.0845 (18)0.0852 (18)0.0454 (14)−0.0310 (16)−0.0009 (12)0.0018 (13)
C120.0365 (10)0.0610 (13)0.0423 (11)0.0007 (10)0.0045 (8)0.0067 (10)
C130.0417 (12)0.0763 (15)0.0633 (14)0.0043 (12)0.0100 (10)0.0097 (12)
C140.0362 (12)0.109 (2)0.0708 (16)−0.0001 (14)0.0087 (11)0.0197 (15)
C150.0502 (14)0.095 (2)0.0660 (15)−0.0220 (14)−0.0047 (11)0.0137 (14)
C160.0624 (15)0.0728 (16)0.0578 (14)−0.0103 (13)−0.0066 (11)−0.0003 (12)
C170.0418 (11)0.0633 (13)0.0557 (13)−0.0011 (11)0.0001 (9)−0.0021 (11)
C180.0482 (12)0.0814 (16)0.0437 (12)0.0037 (11)0.0036 (10)0.0040 (11)
C190.0598 (14)0.1003 (19)0.0444 (13)−0.0009 (14)0.0082 (10)0.0022 (12)
C200.0637 (14)0.0794 (16)0.0503 (13)0.0048 (13)0.0201 (11)0.0082 (12)
C210.0520 (12)0.0551 (12)0.0551 (13)−0.0024 (10)0.0184 (10)−0.0001 (10)
C220.0498 (12)0.0539 (12)0.0500 (12)−0.0030 (10)0.0105 (9)−0.0017 (10)
C230.0856 (18)0.0819 (17)0.0834 (18)−0.0242 (15)0.0308 (14)−0.0037 (14)
N10.0394 (9)0.0572 (10)0.0403 (9)−0.0036 (8)0.0065 (7)−0.0003 (8)
O10.0443 (8)0.0662 (10)0.0620 (10)0.0069 (7)0.0062 (7)−0.0071 (8)
Geometric parameters (Å, °) top
C1—N11.493 (2)C14—H140.9300
C1—C121.518 (3)C15—C161.370 (3)
C1—C21.524 (3)C15—H150.9300
C1—H10.9800C16—C171.381 (3)
C2—C31.379 (3)C16—H160.9300
C2—C71.431 (3)C17—H170.9300
C3—O11.359 (2)C18—N11.477 (2)
C3—C41.411 (3)C18—C191.516 (3)
C4—C51.354 (3)C18—H18A0.9700
C4—H40.9300C18—H18B0.9700
C5—C61.402 (3)C19—C201.510 (3)
C5—H50.9300C19—H19A0.9700
C6—C111.410 (3)C19—H19B0.9700
C6—C71.419 (3)C20—C211.517 (3)
C7—C81.419 (3)C20—H20A0.9700
C8—C91.362 (3)C20—H20B0.9700
C8—H80.9300C21—C231.517 (3)
C9—C101.391 (4)C21—C221.520 (3)
C9—H90.9300C21—H210.9800
C10—C111.356 (4)C22—N11.479 (2)
C10—H100.9300C22—H22A0.9700
C11—H110.9300C22—H22B0.9700
C12—C171.383 (3)C23—H23A0.9600
C12—C131.384 (3)C23—H23B0.9600
C13—C141.378 (3)C23—H23C0.9600
C13—H130.9300O1—H1A0.8200
C14—C151.371 (3)
N1—C1—C12112.81 (15)C14—C15—H15120.1
N1—C1—C2110.03 (15)C15—C16—C17120.2 (2)
C12—C1—C2110.74 (15)C15—C16—H16119.9
N1—C1—H1107.7C17—C16—H16119.9
C12—C1—H1107.7C16—C17—C12120.7 (2)
C2—C1—H1107.7C16—C17—H17119.6
C3—C2—C7118.38 (18)C12—C17—H17119.6
C3—C2—C1121.25 (17)N1—C18—C19109.91 (16)
C7—C2—C1120.33 (17)N1—C18—H18A109.7
O1—C3—C2123.06 (18)C19—C18—H18A109.7
O1—C3—C4115.67 (18)N1—C18—H18B109.7
C2—C3—C4121.3 (2)C19—C18—H18B109.7
C5—C4—C3120.1 (2)H18A—C18—H18B108.2
C5—C4—H4120.0C20—C19—C18112.10 (19)
C3—C4—H4120.0C20—C19—H19A109.2
C4—C5—C6121.6 (2)C18—C19—H19A109.2
C4—C5—H5119.2C20—C19—H19B109.2
C6—C5—H5119.2C18—C19—H19B109.2
C5—C6—C11121.6 (2)H19A—C19—H19B107.9
C5—C6—C7118.5 (2)C19—C20—C21110.91 (17)
C11—C6—C7119.9 (2)C19—C20—H20A109.5
C6—C7—C8116.79 (19)C21—C20—H20A109.5
C6—C7—C2120.03 (19)C19—C20—H20B109.5
C8—C7—C2123.18 (19)C21—C20—H20B109.5
C9—C8—C7121.6 (2)H20A—C20—H20B108.0
C9—C8—H8119.2C20—C21—C23112.82 (18)
C7—C8—H8119.2C20—C21—C22109.29 (17)
C8—C9—C10120.8 (3)C23—C21—C22110.02 (17)
C8—C9—H9119.6C20—C21—H21108.2
C10—C9—H9119.6C23—C21—H21108.2
C11—C10—C9119.7 (2)C22—C21—H21108.2
C11—C10—H10120.1N1—C22—C21112.21 (16)
C9—C10—H10120.1N1—C22—H22A109.2
C10—C11—C6121.2 (2)C21—C22—H22A109.2
C10—C11—H11119.4N1—C22—H22B109.2
C6—C11—H11119.4C21—C22—H22B109.2
C17—C12—C13118.2 (2)H22A—C22—H22B107.9
C17—C12—C1121.84 (17)C21—C23—H23A109.5
C13—C12—C1119.93 (19)C21—C23—H23B109.5
C14—C13—C12121.0 (2)H23A—C23—H23B109.5
C14—C13—H13119.5C21—C23—H23C109.5
C12—C13—H13119.5H23A—C23—H23C109.5
C15—C14—C13120.1 (2)H23B—C23—H23C109.5
C15—C14—H14120.0C18—N1—C22109.40 (15)
C13—C14—H14120.0C18—N1—C1113.43 (14)
C16—C15—C14119.8 (2)C22—N1—C1109.15 (14)
C16—C15—H15120.1C3—O1—H1A109.5
N1—C1—C2—C3−31.0 (2)C7—C6—C11—C10−1.1 (3)
C12—C1—C2—C394.4 (2)N1—C1—C12—C1763.6 (2)
N1—C1—C2—C7151.44 (16)C2—C1—C12—C17−60.2 (2)
C12—C1—C2—C7−83.2 (2)N1—C1—C12—C13−117.4 (2)
C7—C2—C3—O1178.73 (17)C2—C1—C12—C13118.81 (19)
C1—C2—C3—O11.1 (3)C17—C12—C13—C140.3 (3)
C7—C2—C3—C4−1.6 (3)C1—C12—C13—C14−178.80 (18)
C1—C2—C3—C4−179.21 (17)C12—C13—C14—C15−0.3 (3)
O1—C3—C4—C5−177.90 (18)C13—C14—C15—C160.2 (4)
C2—C3—C4—C52.4 (3)C14—C15—C16—C170.0 (3)
C3—C4—C5—C6−0.9 (3)C15—C16—C17—C12−0.1 (3)
C4—C5—C6—C11179.4 (2)C13—C12—C17—C160.0 (3)
C4—C5—C6—C7−1.3 (3)C1—C12—C17—C16179.00 (18)
C5—C6—C7—C8−178.04 (18)N1—C18—C19—C20−57.0 (3)
C11—C6—C7—C81.2 (3)C18—C19—C20—C2153.8 (3)
C5—C6—C7—C22.0 (3)C19—C20—C21—C23−175.32 (19)
C11—C6—C7—C2−178.67 (17)C19—C20—C21—C22−52.6 (2)
C3—C2—C7—C6−0.6 (3)C20—C21—C22—N157.4 (2)
C1—C2—C7—C6177.01 (17)C23—C21—C22—N1−178.25 (18)
C3—C2—C7—C8179.47 (17)C19—C18—N1—C2259.5 (2)
C1—C2—C7—C8−2.9 (3)C19—C18—N1—C1−178.37 (18)
C6—C7—C8—C9−0.2 (3)C21—C22—N1—C18−61.3 (2)
C2—C7—C8—C9179.68 (19)C21—C22—N1—C1174.09 (16)
C7—C8—C9—C10−0.9 (3)C12—C1—N1—C1843.3 (2)
C8—C9—C10—C111.1 (4)C2—C1—N1—C18167.50 (16)
C9—C10—C11—C60.0 (4)C12—C1—N1—C22165.56 (15)
C5—C6—C11—C10178.1 (2)C2—C1—N1—C22−70.23 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.842.570 (2)148
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.842.570 (2)148
Acknowledgements top

This work was supported by Young Researcher funds from Southeast University (grant No. 4007041027).

references
References top

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Szatmari, I. & Fulop, F. (2004). Curr. Org. Synth. 1, 155–165.

Wan, C. & Zhao, H. (2008). Acta Cryst. E64, o1926.

Wang, W. & Zhao, H. (2008). Acta Cryst. E64, o1900.

Zhao, B. & Sun, Y.-X. (2005). Acta Cryst. E61, m652–m653.