1-[(Dimethyl-amino)(phen-yl)meth-yl]naphthalen-2-ol.

In the title compound, C(19)H(19)NO, the dihedral angle between the naphthyl ring system and the phenyl ring is 79.83 (6)°. An intra-molecular O-H⋯N hydrogen bond, together with van der Waals inter-actions, stabilizes the mol-ecular conformation.

Related literature

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

Experimental

Crystal data

C19H19NO

M = 277.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.151

S = 0.99

3440 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

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.

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

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

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

C19H19NO	F(000) = 592
Mr = 277.35	Dx = 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

Rigaku SCXmini diffractometer	3440 independent reflections
Radiation source: fine-focus sealed tube	1835 reflections with I > 2σ(I)
graphite	Rint = 0.083
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −11→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.934, Tmax = 0.992	l = −23→23
14941 measured reflections

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(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3
3440 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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