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Acta Cryst. (2008). E64, o1900    [ doi:10.1107/S1600536808027967 ]

1-[(Dimethylamino)(phenyl)methyl]naphthalen-2-ol

W. Wang and H. Zhao

Abstract top

In the title compound, C19H19NO, the dihedral angle between the naphthyl ring system and the phenyl ring is 79.83 (6)°. An intramolecular O-H...N hydrogen bond, together with van der Waals interactions, stabilizes the molecular conformation.

Comment top

Compounds derived from naphthalen-2-ol have been of great interest in organic chemistry (Szatmari & Fulop, 2004; Zhao & Sun, 2005). We report herein the crystal structure of the title compound (Fig. 1). The dihedral angle between the naphthyl ring and phenyl ring is 79.83 (6)°. Strong intramolecular O—H···N hydrogen bond [O1—H1A = 0.82 Å, H1A···N1 = 1.87 Å, O1···N1 = 2.593 (3) Å, O1—H1A···N1 = 147°] together with van der Waals interactions stabilize the molecular conformation.

Related literature top

For related literature, see: Szatmari & Fulop (2004); Zhao & Sun (2005).

Experimental top

A dry 50 ml flask was charged with benzaldehyde (10 mmol), naphthalen-2-ol (10 mmol), dimethylamine (10 mmol) (33% aq). The mixture was stirred at 100°C for 10 h and then added ethanol (15 ml), after heated under reflux for 30 minutes, the precipitate was filtrated out and washed with ethanol for 2–3 times and purified by recrystallization from dichloromethane to give the target material.

Refinement top

All the hydrogen atoms were calculated geometrically and with C—H distances ranging from 0.93 to 0.98 Å. Caryl—H = 0.93 Å, with Uiso(H) = 1.2Ueq(C). Cmethyl—H = 0.96 Å, with Uiso(H) = 1.5Ueq(C). O—H = 0.82 Å with Uiso(H) = 1.5Ueq(O).

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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular hydrogen bond is indicated by a dashed line.
1-[(Dimethylamino)(phenyl)methyl]naphthalen-2-ol top
Crystal data top
C19H19NOF(000) = 592
Mr = 277.35Dx = 1.222 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2352 reflections
a = 9.3297 (10) Åθ = 2.8–27.5°
b = 9.2042 (10) ŵ = 0.08 mm−1
c = 18.072 (2) ÅT = 293 K
β = 103.66 (2)°Prism, colourless
V = 1508.0 (3) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer		3440 independent reflections
Radiation source: fine-focus sealed tube1835 reflections with I > 2σ(I)
graphiteRint = 0.083
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −11→12
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −11→11
Tmin = 0.934, Tmax = 0.992l = −23→23
14941 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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.061P)2]
where P = (Fo2 + 2Fc2)/3
3440 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C19H19NOV = 1508.0 (3) Å3
Mr = 277.35Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.3297 (10) ŵ = 0.08 mm−1
b = 9.2042 (10) ÅT = 293 K
c = 18.072 (2) Å0.20 × 0.20 × 0.20 mm
β = 103.66 (2)°
Data collection top
Rigaku SCXmini
diffractometer		3440 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		1835 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.992Rint = 0.083
14941 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.151Δρmax = 0.13 e Å−3
S = 0.99Δρmin = −0.18 e Å−3
3440 reflectionsAbsolute structure: ?
193 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C10.9601 (2)0.1887 (2)0.19972 (12)0.0402 (5)
H11.00000.27280.23120.048*
C20.8401 (2)0.2439 (2)0.13328 (12)0.0376 (5)
C30.7170 (2)0.1608 (2)0.10134 (13)0.0431 (5)
C40.6082 (2)0.2123 (3)0.03982 (13)0.0486 (6)
H40.52530.15580.02020.058*
C50.6229 (3)0.3438 (3)0.00864 (12)0.0490 (6)
H50.54980.3759−0.03250.059*
C60.7468 (2)0.4334 (2)0.03727 (12)0.0428 (5)
C70.8563 (2)0.3830 (2)0.09998 (12)0.0379 (5)
C80.9798 (3)0.4747 (2)0.12697 (13)0.0489 (6)
H81.05470.44420.16770.059*
C90.9911 (3)0.6069 (3)0.09435 (15)0.0597 (7)
H91.07300.66510.11350.072*
C100.8826 (3)0.6557 (3)0.03331 (15)0.0624 (7)
H100.89140.74580.01160.075*
C110.7632 (3)0.5708 (3)0.00549 (14)0.0542 (6)
H110.69040.6038−0.03550.065*
C121.0864 (2)0.1206 (2)0.17158 (12)0.0396 (5)
C131.2301 (2)0.1639 (3)0.20272 (14)0.0540 (6)
H131.24890.23410.24080.065*
C141.3465 (3)0.1033 (3)0.17760 (16)0.0653 (8)
H141.44270.13280.19920.078*
C151.3208 (3)0.0005 (3)0.12133 (16)0.0593 (7)
H151.3990−0.03970.10460.071*
C161.1786 (3)−0.0430 (3)0.08969 (14)0.0540 (6)
H161.1604−0.11290.05150.065*
C171.0626 (2)0.0171 (2)0.11468 (13)0.0462 (6)
H170.9667−0.01280.09280.055*
C181.0071 (3)0.0025 (3)0.30073 (15)0.0662 (8)
H18A1.07960.06640.33050.099*
H18B1.0540−0.06290.27240.099*
H18C0.9609−0.05230.33390.099*
C190.8097 (3)0.1744 (3)0.29155 (15)0.0677 (8)
H19A0.76130.11030.31980.102*
H19B0.73720.23110.25690.102*
H19C0.87490.23780.32610.102*
N10.8956 (2)0.0879 (2)0.24811 (10)0.0481 (5)
O10.69398 (18)0.02542 (17)0.12688 (10)0.0592 (5)
H1A0.75390.00970.16720.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0412 (12)0.0364 (12)0.0438 (13)−0.0011 (10)0.0117 (10)0.0019 (10)
C20.0360 (12)0.0381 (12)0.0410 (13)0.0018 (10)0.0135 (10)0.0014 (9)
C30.0402 (13)0.0405 (12)0.0503 (15)0.0013 (11)0.0141 (11)0.0035 (10)
C40.0397 (13)0.0556 (15)0.0491 (15)−0.0006 (11)0.0073 (11)−0.0021 (12)
C50.0462 (14)0.0590 (15)0.0405 (14)0.0094 (12)0.0073 (11)0.0010 (11)
C60.0464 (13)0.0427 (13)0.0423 (13)0.0039 (11)0.0166 (11)0.0019 (10)
C70.0370 (12)0.0399 (12)0.0397 (13)0.0043 (10)0.0148 (10)0.0011 (10)
C80.0486 (14)0.0448 (13)0.0536 (15)−0.0018 (11)0.0125 (11)0.0029 (11)
C90.0646 (17)0.0475 (15)0.0683 (18)−0.0114 (13)0.0183 (14)0.0011 (13)
C100.085 (2)0.0431 (14)0.0640 (18)−0.0012 (14)0.0260 (16)0.0130 (13)
C110.0666 (17)0.0503 (15)0.0475 (15)0.0100 (13)0.0168 (13)0.0092 (12)
C120.0361 (12)0.0408 (12)0.0418 (13)0.0009 (10)0.0086 (10)0.0067 (10)
C130.0412 (14)0.0561 (15)0.0619 (16)−0.0012 (12)0.0065 (12)−0.0048 (12)
C140.0363 (13)0.0688 (18)0.089 (2)−0.0012 (13)0.0103 (13)−0.0003 (16)
C150.0493 (15)0.0571 (16)0.0778 (19)0.0072 (13)0.0276 (14)0.0082 (14)
C160.0569 (16)0.0489 (14)0.0606 (16)0.0015 (12)0.0223 (13)−0.0007 (12)
C170.0400 (13)0.0470 (13)0.0521 (15)−0.0034 (11)0.0122 (11)−0.0014 (11)
C180.0735 (18)0.0670 (17)0.0590 (17)0.0127 (15)0.0176 (14)0.0236 (14)
C190.0742 (19)0.0733 (19)0.0667 (18)0.0143 (15)0.0389 (15)0.0139 (14)
N10.0520 (12)0.0487 (12)0.0467 (11)0.0042 (9)0.0175 (9)0.0115 (9)
O10.0501 (10)0.0480 (10)0.0767 (13)−0.0078 (8)0.0093 (9)0.0119 (9)
Geometric parameters (Å, °) top
C1—N11.496 (3)C11—H110.9300
C1—C21.523 (3)C12—C171.381 (3)
C1—C121.524 (3)C12—C131.385 (3)
C1—H10.9800C13—C141.389 (3)
C2—C31.387 (3)C13—H130.9300
C2—C71.438 (3)C14—C151.368 (4)
C3—O11.364 (2)C14—H140.9300
C3—C41.399 (3)C15—C161.374 (3)
C4—C51.356 (3)C15—H150.9300
C4—H40.9300C16—C171.383 (3)
C5—C61.415 (3)C16—H160.9300
C5—H50.9300C17—H170.9300
C6—C111.412 (3)C18—N11.462 (3)
C6—C71.413 (3)C18—H18A0.9600
C7—C81.419 (3)C18—H18B0.9600
C8—C91.367 (3)C18—H18C0.9600
C8—H80.9300C19—N11.480 (3)
C9—C101.384 (3)C19—H19A0.9600
C9—H90.9300C19—H19B0.9600
C10—C111.356 (3)C19—H19C0.9600
C10—H100.9300O1—H1A0.8200
N1—C1—C2110.19 (17)C6—C11—H11119.2
N1—C1—C12112.93 (17)C17—C12—C13118.1 (2)
C2—C1—C12110.88 (17)C17—C12—C1122.09 (19)
N1—C1—H1107.5C13—C12—C1119.8 (2)
C2—C1—H1107.5C12—C13—C14120.6 (2)
C12—C1—H1107.5C12—C13—H13119.7
C3—C2—C7118.36 (19)C14—C13—H13119.7
C3—C2—C1121.80 (18)C15—C14—C13120.5 (2)
C7—C2—C1119.78 (18)C15—C14—H14119.8
O1—C3—C2123.0 (2)C13—C14—H14119.8
O1—C3—C4115.8 (2)C14—C15—C16119.6 (2)
C2—C3—C4121.2 (2)C14—C15—H15120.2
C5—C4—C3120.5 (2)C16—C15—H15120.2
C5—C4—H4119.8C15—C16—C17120.0 (2)
C3—C4—H4119.8C15—C16—H16120.0
C4—C5—C6121.5 (2)C17—C16—H16120.0
C4—C5—H5119.3C12—C17—C16121.2 (2)
C6—C5—H5119.3C12—C17—H17119.4
C11—C6—C7119.5 (2)C16—C17—H17119.4
C11—C6—C5122.1 (2)N1—C18—H18A109.5
C7—C6—C5118.4 (2)N1—C18—H18B109.5
C6—C7—C8117.06 (19)H18A—C18—H18B109.5
C6—C7—C2120.06 (19)N1—C18—H18C109.5
C8—C7—C2122.9 (2)H18A—C18—H18C109.5
C9—C8—C7121.4 (2)H18B—C18—H18C109.5
C9—C8—H8119.3N1—C19—H19A109.5
C7—C8—H8119.3N1—C19—H19B109.5
C8—C9—C10121.1 (2)H19A—C19—H19B109.5
C8—C9—H9119.5N1—C19—H19C109.5
C10—C9—H9119.5H19A—C19—H19C109.5
C11—C10—C9119.4 (2)H19B—C19—H19C109.5
C11—C10—H10120.3C18—N1—C19109.61 (19)
C9—C10—H10120.3C18—N1—C1113.02 (18)
C10—C11—C6121.6 (2)C19—N1—C1108.65 (18)
C10—C11—H11119.2C3—O1—H1A109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.872.593 (3)147
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.872.593 (3)147
Acknowledgements top

This work was supported by a Start-up Grant from Southeast University to HZ.

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.

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