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

Wang, W.; Zhao, H.

doi:10.1107/S1600536808027967

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1900

doi:10.1107/S1600536808027967

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

Wenxiang Wang ^a and Hong Zhao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 29 August 2008; accepted 2 September 2008; online 6 September 2008)

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.

Related literature

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

Experimental

Crystal data

C₁₉H₁₉NO
M_r = 277.35
Monoclinic, P 2₁ /n
a = 9.3297 (10) Å
b = 9.2042 (10) Å
c = 18.072 (2) Å
β = 103.66 (2)°
V = 1508.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.934, T_max = 0.992
14941 measured reflections
3440 independent reflections
1835 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.151
S = 0.99
3440 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.87	2.593 (3)	147

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027967/bx2176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027967/bx2176Isup2.hkl

checkCIF report

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.

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

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

C₁₉H₁₉NO	F(000) = 592
M_r = 277.35	D_x = 1.222 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2352 reflections
a = 9.3297 (10) Å	θ = 2.8–27.5°
b = 9.2042 (10) Å	µ = 0.08 mm⁻¹
c = 18.072 (2) Å	T = 293 K
β = 103.66 (2)°	Prism, colourless
V = 1508.0 (3) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	3440 independent reflections
Radiation source: fine-focus sealed tube	1835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −11→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.934, T_max = 0.992	l = −23→23
14941 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.061P)²] where P = (F_o² + 2F_c²)/3
3440 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₁₉NO	V = 1508.0 (3) Å³
M_r = 277.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3297 (10) Å	µ = 0.08 mm⁻¹
b = 9.2042 (10) Å	T = 293 K
c = 18.072 (2) Å	0.20 × 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)
T_min = 0.934, T_max = 0.992	R_int = 0.083
14941 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 0.99	Δρ_max = 0.13 e Å⁻³
3440 reflections	Δρ_min = −0.18 e Å⁻³
193 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.9601 (2)	0.1887 (2)	0.19972 (12)	0.0402 (5)
H1	1.0000	0.2728	0.2312	0.048*
C2	0.8401 (2)	0.2439 (2)	0.13328 (12)	0.0376 (5)
C3	0.7170 (2)	0.1608 (2)	0.10134 (13)	0.0431 (5)
C4	0.6082 (2)	0.2123 (3)	0.03982 (13)	0.0486 (6)
H4	0.5253	0.1558	0.0202	0.058*
C5	0.6229 (3)	0.3438 (3)	0.00864 (12)	0.0490 (6)
H5	0.5498	0.3759	−0.0325	0.059*
C6	0.7468 (2)	0.4334 (2)	0.03727 (12)	0.0428 (5)
C7	0.8563 (2)	0.3830 (2)	0.09998 (12)	0.0379 (5)
C8	0.9798 (3)	0.4747 (2)	0.12697 (13)	0.0489 (6)
H8	1.0547	0.4442	0.1677	0.059*
C9	0.9911 (3)	0.6069 (3)	0.09435 (15)	0.0597 (7)
H9	1.0730	0.6651	0.1135	0.072*
C10	0.8826 (3)	0.6557 (3)	0.03331 (15)	0.0624 (7)
H10	0.8914	0.7458	0.0116	0.075*
C11	0.7632 (3)	0.5708 (3)	0.00549 (14)	0.0542 (6)
H11	0.6904	0.6038	−0.0355	0.065*
C12	1.0864 (2)	0.1206 (2)	0.17158 (12)	0.0396 (5)
C13	1.2301 (2)	0.1639 (3)	0.20272 (14)	0.0540 (6)
H13	1.2489	0.2341	0.2408	0.065*
C14	1.3465 (3)	0.1033 (3)	0.17760 (16)	0.0653 (8)
H14	1.4427	0.1328	0.1992	0.078*
C15	1.3208 (3)	0.0005 (3)	0.12133 (16)	0.0593 (7)
H15	1.3990	−0.0397	0.1046	0.071*
C16	1.1786 (3)	−0.0430 (3)	0.08969 (14)	0.0540 (6)
H16	1.1604	−0.1129	0.0515	0.065*
C17	1.0626 (2)	0.0171 (2)	0.11468 (13)	0.0462 (6)
H17	0.9667	−0.0128	0.0928	0.055*
C18	1.0071 (3)	0.0025 (3)	0.30073 (15)	0.0662 (8)
H18A	1.0796	0.0664	0.3305	0.099*
H18B	1.0540	−0.0629	0.2724	0.099*
H18C	0.9609	−0.0523	0.3339	0.099*
C19	0.8097 (3)	0.1744 (3)	0.29155 (15)	0.0677 (8)
H19A	0.7613	0.1103	0.3198	0.102*
H19B	0.7372	0.2311	0.2569	0.102*
H19C	0.8749	0.2378	0.3261	0.102*
N1	0.8956 (2)	0.0879 (2)	0.24811 (10)	0.0481 (5)
O1	0.69398 (18)	0.02542 (17)	0.12688 (10)	0.0592 (5)
H1A	0.7539	0.0097	0.1672	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0412 (12)	0.0364 (12)	0.0438 (13)	−0.0011 (10)	0.0117 (10)	0.0019 (10)
C2	0.0360 (12)	0.0381 (12)	0.0410 (13)	0.0018 (10)	0.0135 (10)	0.0014 (9)
C3	0.0402 (13)	0.0405 (12)	0.0503 (15)	0.0013 (11)	0.0141 (11)	0.0035 (10)
C4	0.0397 (13)	0.0556 (15)	0.0491 (15)	−0.0006 (11)	0.0073 (11)	−0.0021 (12)
C5	0.0462 (14)	0.0590 (15)	0.0405 (14)	0.0094 (12)	0.0073 (11)	0.0010 (11)
C6	0.0464 (13)	0.0427 (13)	0.0423 (13)	0.0039 (11)	0.0166 (11)	0.0019 (10)
C7	0.0370 (12)	0.0399 (12)	0.0397 (13)	0.0043 (10)	0.0148 (10)	0.0011 (10)
C8	0.0486 (14)	0.0448 (13)	0.0536 (15)	−0.0018 (11)	0.0125 (11)	0.0029 (11)
C9	0.0646 (17)	0.0475 (15)	0.0683 (18)	−0.0114 (13)	0.0183 (14)	0.0011 (13)
C10	0.085 (2)	0.0431 (14)	0.0640 (18)	−0.0012 (14)	0.0260 (16)	0.0130 (13)
C11	0.0666 (17)	0.0503 (15)	0.0475 (15)	0.0100 (13)	0.0168 (13)	0.0092 (12)
C12	0.0361 (12)	0.0408 (12)	0.0418 (13)	0.0009 (10)	0.0086 (10)	0.0067 (10)
C13	0.0412 (14)	0.0561 (15)	0.0619 (16)	−0.0012 (12)	0.0065 (12)	−0.0048 (12)
C14	0.0363 (13)	0.0688 (18)	0.089 (2)	−0.0012 (13)	0.0103 (13)	−0.0003 (16)
C15	0.0493 (15)	0.0571 (16)	0.0778 (19)	0.0072 (13)	0.0276 (14)	0.0082 (14)
C16	0.0569 (16)	0.0489 (14)	0.0606 (16)	0.0015 (12)	0.0223 (13)	−0.0007 (12)
C17	0.0400 (13)	0.0470 (13)	0.0521 (15)	−0.0034 (11)	0.0122 (11)	−0.0014 (11)
C18	0.0735 (18)	0.0670 (17)	0.0590 (17)	0.0127 (15)	0.0176 (14)	0.0236 (14)
C19	0.0742 (19)	0.0733 (19)	0.0667 (18)	0.0143 (15)	0.0389 (15)	0.0139 (14)
N1	0.0520 (12)	0.0487 (12)	0.0467 (11)	0.0042 (9)	0.0175 (9)	0.0115 (9)
O1	0.0501 (10)	0.0480 (10)	0.0767 (13)	−0.0078 (8)	0.0093 (9)	0.0119 (9)

Geometric parameters (Å, º) top

C1—N1	1.496 (3)	C11—H11	0.9300
C1—C2	1.523 (3)	C12—C17	1.381 (3)
C1—C12	1.524 (3)	C12—C13	1.385 (3)
C1—H1	0.9800	C13—C14	1.389 (3)
C2—C3	1.387 (3)	C13—H13	0.9300
C2—C7	1.438 (3)	C14—C15	1.368 (4)
C3—O1	1.364 (2)	C14—H14	0.9300
C3—C4	1.399 (3)	C15—C16	1.374 (3)
C4—C5	1.356 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.383 (3)
C5—C6	1.415 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—C11	1.412 (3)	C18—N1	1.462 (3)
C6—C7	1.413 (3)	C18—H18A	0.9600
C7—C8	1.419 (3)	C18—H18B	0.9600
C8—C9	1.367 (3)	C18—H18C	0.9600
C8—H8	0.9300	C19—N1	1.480 (3)
C9—C10	1.384 (3)	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—C11	1.356 (3)	C19—H19C	0.9600
C10—H10	0.9300	O1—H1A	0.8200

N1—C1—C2	110.19 (17)	C6—C11—H11	119.2
N1—C1—C12	112.93 (17)	C17—C12—C13	118.1 (2)
C2—C1—C12	110.88 (17)	C17—C12—C1	122.09 (19)
N1—C1—H1	107.5	C13—C12—C1	119.8 (2)
C2—C1—H1	107.5	C12—C13—C14	120.6 (2)
C12—C1—H1	107.5	C12—C13—H13	119.7
C3—C2—C7	118.36 (19)	C14—C13—H13	119.7
C3—C2—C1	121.80 (18)	C15—C14—C13	120.5 (2)
C7—C2—C1	119.78 (18)	C15—C14—H14	119.8
O1—C3—C2	123.0 (2)	C13—C14—H14	119.8
O1—C3—C4	115.8 (2)	C14—C15—C16	119.6 (2)
C2—C3—C4	121.2 (2)	C14—C15—H15	120.2
C5—C4—C3	120.5 (2)	C16—C15—H15	120.2
C5—C4—H4	119.8	C15—C16—C17	120.0 (2)
C3—C4—H4	119.8	C15—C16—H16	120.0
C4—C5—C6	121.5 (2)	C17—C16—H16	120.0
C4—C5—H5	119.3	C12—C17—C16	121.2 (2)
C6—C5—H5	119.3	C12—C17—H17	119.4
C11—C6—C7	119.5 (2)	C16—C17—H17	119.4
C11—C6—C5	122.1 (2)	N1—C18—H18A	109.5
C7—C6—C5	118.4 (2)	N1—C18—H18B	109.5
C6—C7—C8	117.06 (19)	H18A—C18—H18B	109.5
C6—C7—C2	120.06 (19)	N1—C18—H18C	109.5
C8—C7—C2	122.9 (2)	H18A—C18—H18C	109.5
C9—C8—C7	121.4 (2)	H18B—C18—H18C	109.5
C9—C8—H8	119.3	N1—C19—H19A	109.5
C7—C8—H8	119.3	N1—C19—H19B	109.5
C8—C9—C10	121.1 (2)	H19A—C19—H19B	109.5
C8—C9—H9	119.5	N1—C19—H19C	109.5
C10—C9—H9	119.5	H19A—C19—H19C	109.5
C11—C10—C9	119.4 (2)	H19B—C19—H19C	109.5
C11—C10—H10	120.3	C18—N1—C19	109.61 (19)
C9—C10—H10	120.3	C18—N1—C1	113.02 (18)
C10—C11—C6	121.6 (2)	C19—N1—C1	108.65 (18)
C10—C11—H11	119.2	C3—O1—H1A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.87	2.593 (3)	147

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO
M_r	277.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.3297 (10), 9.2042 (10), 18.072 (2)
β (°)	103.66 (2)
V (Å³)	1508.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.934, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	14941, 3440, 1835
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.151, 0.99
No. of reflections	3440
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.87	2.593 (3)	147

Acknowledgements

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

References

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szatmari, I. & Fulop, F. (2004). Curr. Org. Synth. 1, 155-165. Web of Science CrossRef CAS Google Scholar
Zhao, B. & Sun, Y.-X. (2005). Acta Cryst. E61, m652–m653. CSD CrossRef IUCr Journals Google Scholar