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

In the title compound, C(21)H(23)NO, obtained via a one-pot synthesis, an intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. The dihedral angle between the fused ring system and the phenyl ring is 78.27 (5)°. The crystal packing is characterized by helical chains of mol-ecules linked by C-H⋯O hydrogen bonds.

Related literature

For applications of Betti-type reactions, see: Zhao et al. (2004 ▶); Lu et al. (2002 ▶); Xu et al. (2004 ▶); Wang et al. (2005 ▶)

Experimental

Crystal data

C21H23NO

M = 305.40

Orthorhombic,

a = 10.842 (7) Å

b = 16.651 (7) Å

c = 9.787 (6) Å

V = 1766.9 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.856, T max = 1.000

14129 measured reflections

3121 independent reflections

1998 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.134

S = 1.02

3121 reflections

211 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.13 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/S1600536811000067/gw2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000067/gw2088Isup2.hkl

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

C21H23NO	F(000) = 656
Mr = 305.40	Dx = 1.148 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2229 reflections
a = 10.842 (7) Å	θ = 2.4–27.4°
b = 16.651 (7) Å	µ = 0.07 mm−1
c = 9.787 (6) Å	T = 293 K
V = 1766.9 (17) Å3	Prism, colorless
Z = 4	0.30 × 0.25 × 0.15 mm

Rigaku Mercury2 diffractometer	3121 independent reflections
Radiation source: fine-focus sealed tube	1998 reflections with I > 2σ(I)
graphite	Rint = 0.078
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 2.4°
CCD_Profile_fitting scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.856, Tmax = 1.000	l = −11→11
14129 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.087	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0007P)2 + 1.9999P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3121 reflections	Δρmax = 0.25 e Å−3
211 parameters	Δρmin = −0.13 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (9)

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
O1	0.2175 (3)	0.0230 (2)	0.4209 (4)	0.0825 (11)
H1A	0.2786	0.0483	0.3966	0.124*
N1	0.4017 (4)	0.1176 (2)	0.4649 (5)	0.0718 (12)
H1D	0.4572	0.1535	0.4201	0.086*
C1	0.1998 (4)	0.1346 (3)	0.5773 (5)	0.0551 (12)
C2	0.1594 (4)	0.0636 (3)	0.5250 (5)	0.0657 (14)
C3	0.0511 (5)	0.0240 (3)	0.5748 (5)	0.0717 (16)
H3A	0.0260	−0.0245	0.5368	0.086*
C4	−0.0136 (5)	0.0574 (4)	0.6767 (6)	0.0748 (16)
H4A	−0.0832	0.0311	0.7097	0.090*
C5	−0.0463 (5)	0.1666 (4)	0.8420 (6)	0.0822 (18)
H5A	−0.1145	0.1397	0.8769	0.099*
C6	−0.0147 (6)	0.2386 (5)	0.8958 (6)	0.093 (2)
H6A	−0.0610	0.2609	0.9662	0.111*
C7	0.0874 (6)	0.2788 (4)	0.8448 (6)	0.0899 (19)
H7A	0.1090	0.3282	0.8822	0.108*
C8	0.1585 (5)	0.2473 (4)	0.7391 (5)	0.0739 (16)
H8A	0.2257	0.2758	0.7055	0.089*
C9	0.1277 (4)	0.1714 (3)	0.6832 (5)	0.0601 (13)
C10	0.0212 (4)	0.1313 (3)	0.7350 (5)	0.0646 (14)
C11	0.3145 (4)	0.1767 (3)	0.5238 (5)	0.0566 (12)
H11A	0.3552	0.2032	0.6009	0.068*
C12	0.2873 (4)	0.2400 (3)	0.4156 (5)	0.0603 (12)
C13	0.1947 (6)	0.2301 (4)	0.3193 (6)	0.094 (2)
H13A	0.1443	0.1849	0.3231	0.113*
C14	0.1761 (6)	0.2872 (5)	0.2161 (7)	0.113 (2)
H14A	0.1128	0.2807	0.1530	0.136*
C15	0.2523 (6)	0.3530 (4)	0.2093 (7)	0.098 (2)
H15A	0.2425	0.3901	0.1390	0.118*
C16	0.3415 (6)	0.3644 (4)	0.3043 (6)	0.097 (2)
H16A	0.3908	0.4100	0.3015	0.116*
C17	0.3588 (5)	0.3071 (3)	0.4058 (6)	0.0789 (16)
H17A	0.4215	0.3148	0.4694	0.095*
C18	0.4708 (5)	0.0719 (4)	0.5698 (7)	0.0921 (19)
H18A	0.4145	0.0401	0.6248	0.111*
H18B	0.5153	0.1083	0.6294	0.111*
C19	0.5652 (6)	0.0146 (5)	0.4899 (8)	0.127 (3)
H19A	0.5187	−0.0218	0.4321	0.152*
H19B	0.6169	0.0472	0.4312	0.152*
C20	0.6390 (7)	−0.0296 (5)	0.5756 (10)	0.162 (4)
H20A	0.5881	−0.0654	0.6297	0.194*
H20B	0.6816	0.0064	0.6377	0.194*
C21	0.7336 (6)	−0.0788 (5)	0.4962 (9)	0.153 (4)
H21A	0.7833	−0.1090	0.5589	0.230*
H21B	0.7854	−0.0434	0.4441	0.230*
H21C	0.6916	−0.1149	0.4355	0.230*

	U11	U22	U33	U12	U13	U23
O1	0.079 (2)	0.084 (2)	0.085 (3)	−0.017 (2)	0.006 (2)	−0.019 (2)
N1	0.053 (2)	0.076 (3)	0.086 (3)	−0.001 (2)	0.009 (2)	−0.003 (3)
C1	0.045 (3)	0.070 (3)	0.050 (3)	−0.004 (2)	−0.003 (2)	0.003 (3)
C2	0.057 (3)	0.075 (4)	0.065 (4)	−0.001 (3)	−0.002 (3)	−0.001 (3)
C3	0.060 (3)	0.075 (4)	0.080 (4)	−0.010 (3)	−0.002 (3)	0.009 (3)
C4	0.053 (3)	0.091 (4)	0.080 (4)	−0.007 (3)	0.000 (3)	0.028 (3)
C5	0.065 (4)	0.110 (5)	0.072 (4)	0.021 (4)	−0.002 (3)	0.022 (4)
C6	0.075 (4)	0.128 (6)	0.075 (5)	0.031 (4)	0.010 (4)	−0.002 (4)
C7	0.100 (5)	0.095 (5)	0.074 (4)	0.024 (4)	−0.016 (4)	−0.013 (4)
C8	0.073 (4)	0.090 (4)	0.058 (4)	0.008 (3)	−0.014 (3)	−0.002 (3)
C9	0.050 (3)	0.074 (4)	0.057 (3)	0.001 (3)	−0.014 (2)	0.013 (3)
C10	0.053 (3)	0.087 (4)	0.054 (3)	0.016 (3)	−0.004 (3)	0.006 (3)
C11	0.047 (3)	0.064 (3)	0.059 (3)	−0.003 (2)	−0.004 (2)	−0.010 (3)
C12	0.059 (3)	0.067 (3)	0.055 (3)	−0.008 (3)	−0.002 (3)	−0.013 (3)
C13	0.108 (5)	0.103 (5)	0.072 (4)	−0.042 (4)	−0.023 (4)	0.017 (4)
C14	0.109 (5)	0.146 (7)	0.085 (5)	−0.022 (5)	−0.038 (4)	0.034 (5)
C15	0.125 (6)	0.104 (5)	0.066 (4)	−0.002 (5)	0.003 (4)	0.028 (4)
C16	0.119 (6)	0.084 (5)	0.088 (5)	−0.025 (4)	0.000 (4)	0.008 (4)
C17	0.080 (4)	0.075 (4)	0.082 (4)	−0.021 (3)	−0.012 (3)	0.010 (4)
C18	0.076 (4)	0.086 (4)	0.115 (5)	0.009 (3)	−0.012 (4)	−0.005 (4)
C19	0.077 (5)	0.151 (7)	0.152 (8)	0.026 (4)	−0.008 (5)	0.026 (6)
C20	0.136 (8)	0.188 (10)	0.161 (9)	0.033 (7)	−0.001 (7)	−0.012 (8)
C21	0.105 (6)	0.109 (6)	0.245 (11)	0.032 (5)	0.032 (6)	−0.047 (6)

O1—C2	1.375 (6)	C11—H11A	0.9800
O1—H1A	0.8200	C12—C17	1.363 (6)
N1—C18	1.481 (6)	C12—C13	1.387 (6)
N1—C11	1.483 (5)	C13—C14	1.402 (8)
N1—H1D	0.9548	C13—H13A	0.9300
C1—C2	1.362 (6)	C14—C15	1.374 (8)
C1—C9	1.435 (7)	C14—H14A	0.9300
C1—C11	1.520 (6)	C15—C16	1.355 (8)
C2—C3	1.431 (6)	C15—H15A	0.9300
C3—C4	1.340 (7)	C16—C17	1.390 (8)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C10	1.409 (7)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.603 (8)
C5—C6	1.353 (8)	C18—H18A	0.9700
C5—C10	1.406 (8)	C18—H18B	0.9700
C5—H5A	0.9300	C19—C20	1.373 (9)
C6—C7	1.386 (8)	C19—H19A	0.9700
C6—H6A	0.9300	C19—H19B	0.9700
C7—C8	1.393 (7)	C20—C21	1.526 (9)
C7—H7A	0.9300	C20—H20A	0.9700
C8—C9	1.417 (7)	C20—H20B	0.9700
C8—H8A	0.9300	C21—H21A	0.9600
C9—C10	1.427 (6)	C21—H21B	0.9600
C11—C12	1.523 (6)	C21—H21C	0.9600
C2—O1—H1A	109.5	C17—C12—C11	120.4 (5)
C18—N1—C11	113.2 (4)	C13—C12—C11	122.0 (5)
C18—N1—H1D	108.8	C12—C13—C14	120.8 (6)
C11—N1—H1D	99.4	C12—C13—H13A	119.6
C2—C1—C9	117.8 (5)	C14—C13—H13A	119.6
C2—C1—C11	122.3 (4)	C15—C14—C13	119.4 (6)
C9—C1—C11	119.8 (4)	C15—C14—H14A	120.3
C1—C2—O1	123.9 (5)	C13—C14—H14A	120.3
C1—C2—C3	122.4 (5)	C16—C15—C14	120.4 (6)
O1—C2—C3	113.7 (5)	C16—C15—H15A	119.8
C4—C3—C2	119.5 (5)	C14—C15—H15A	119.8
C4—C3—H3A	120.2	C15—C16—C17	119.4 (6)
C2—C3—H3A	120.2	C15—C16—H16A	120.3
C3—C4—C10	121.6 (5)	C17—C16—H16A	120.3
C3—C4—H4A	119.2	C12—C17—C16	122.3 (6)
C10—C4—H4A	119.2	C12—C17—H17A	118.8
C6—C5—C10	121.9 (6)	C16—C17—H17A	118.8
C6—C5—H5A	119.1	N1—C18—C19	106.9 (5)
C10—C5—H5A	119.1	N1—C18—H18A	110.3
C5—C6—C7	119.3 (6)	C19—C18—H18A	110.3
C5—C6—H6A	120.3	N1—C18—H18B	110.3
C7—C6—H6A	120.3	C19—C18—H18B	110.3
C6—C7—C8	121.8 (6)	H18A—C18—H18B	108.6
C6—C7—H7A	119.1	C20—C19—C18	113.2 (7)
C8—C7—H7A	119.1	C20—C19—H19A	108.9
C7—C8—C9	119.5 (6)	C18—C19—H19A	108.9
C7—C8—H8A	120.2	C20—C19—H19B	108.9
C9—C8—H8A	120.2	C18—C19—H19B	108.9
C8—C9—C10	118.0 (5)	H19A—C19—H19B	107.8
C8—C9—C1	122.1 (5)	C19—C20—C21	111.6 (8)
C10—C9—C1	119.9 (5)	C19—C20—H20A	109.3
C5—C10—C4	121.9 (6)	C21—C20—H20A	109.3
C5—C10—C9	119.4 (6)	C19—C20—H20B	109.3
C4—C10—C9	118.8 (5)	C21—C20—H20B	109.3
N1—C11—C1	110.4 (4)	H20A—C20—H20B	108.0
N1—C11—C12	108.2 (4)	C20—C21—H21A	109.5
C1—C11—C12	113.6 (4)	C20—C21—H21B	109.5
N1—C11—H11A	108.1	H21A—C21—H21B	109.5
C1—C11—H11A	108.1	C20—C21—H21C	109.5
C12—C11—H11A	108.1	H21A—C21—H21C	109.5
C17—C12—C13	117.5 (5)	H21B—C21—H21C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.89	2.580 (5)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.89	2.580 (5)	142