2-(Naphthalen-1-yl-amino)-cyclo-hexa-nol.

The title compound, C(16)H(19)NO, was synthesized under solvent-free conditions by reaction of 7-oxa-bicyclo-[4.1.0]heptane and naphthalen-1-amine in the presence of Ca(CF(3)COO)(2) as catalyst. The cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions into chains parallel to the c axis.

Related literature

For background to applications of β-amino­alcohols in organic synthesis, see: Rogers et al. (1989 ▶); O’Brien (1999 ▶); Ager et al. (1996 ▶). For the synthesis of β-amino­alcohols, see: Deyrup & Moyer (1969 ▶); Kamal, Ramu et al. (2005 ▶); Yarapathy et al. (2006 ▶); Yadav et al. (2003 ▶); Rafiee et al. (2004 ▶); Robin et al. (2007 ▶); Das et al. (2000 ▶); Kamal, Adil & Arifuddin (2005 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H19NO

M = 241.32

Orthorhombic,

a = 12.0278 (4) Å

b = 11.5910 (3) Å

c = 9.5566 (3) Å

V = 1332.33 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.58 mm−1

T = 294 K

0.18 × 0.15 × 0.10 mm

Data collection

Siemens AED diffractometer

4933 measured reflections

1353 independent reflections

1326 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections every 100 reflections intensity decay: 0.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.087

S = 1.08

1353 reflections

169 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: AED (Belletti et al., 1993 ▶); cell refinement: AED; data reduction: AED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and SCHAKAL97 (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021714/zl2377sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021714/zl2377Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021714/zl2377Isup3.cml

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

C16H19NO	F(000) = 520
Mr = 241.32	Dx = 1.203 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 48 reflections
a = 12.0278 (4) Å	θ = 16.7–36.3°
b = 11.5910 (3) Å	µ = 0.58 mm−1
c = 9.5566 (3) Å	T = 294 K
V = 1332.33 (7) Å3	Block, pale-blue
Z = 4	0.18 × 0.15 × 0.10 mm

Siemens AED diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 69.9°, θmin = 3.8°
graphite	h = −14→13
θ/2θ scans	k = −14→13
4933 measured reflections	l = −11→5
1353 independent reflections	3 standard reflections every 100 reflections
1326 reflections with I > 2σ(I)	intensity decay: 0.0%

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.0897P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1353 reflections	Δρmax = 0.14 e Å−3
169 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (11)

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	0.27577 (13)	−0.01165 (12)	0.00639 (19)	0.0690 (4)
H1O	0.2788	0.0522	0.0431	0.104*
N1	0.14586 (12)	0.08201 (12)	0.21600 (17)	0.0491 (3)
H1N	0.1730 (16)	0.0622 (17)	0.292 (3)	0.054 (5)*
C1	0.20467 (14)	−0.08488 (14)	0.08667 (19)	0.0471 (4)
H1	0.2464	−0.1137	0.1675	0.057*
C2	0.16883 (16)	−0.18640 (16)	−0.0013 (2)	0.0572 (4)
H2A	0.2339	−0.2284	−0.0331	0.069*
H2B	0.1288	−0.1591	−0.0829	0.069*
C3	0.09482 (17)	−0.26593 (17)	0.0831 (3)	0.0661 (6)
H3A	0.1366	−0.2976	0.1609	0.079*
H3B	0.0706	−0.3296	0.0246	0.079*
C4	−0.00636 (18)	−0.20139 (19)	0.1385 (3)	0.0747 (7)
H4A	−0.0500	−0.2527	0.1969	0.090*
H4B	−0.0525	−0.1774	0.0605	0.090*
C5	0.02757 (15)	−0.09561 (16)	0.2233 (2)	0.0577 (5)
H5A	−0.0384	−0.0529	0.2503	0.069*
H5B	0.0651	−0.1202	0.3081	0.069*
C6	0.10412 (13)	−0.01752 (13)	0.13964 (18)	0.0458 (4)
H6	0.0628	0.0107	0.0582	0.055*
C7	0.08882 (12)	0.18703 (14)	0.22162 (18)	0.0431 (3)
C8	−0.01028 (14)	0.20562 (15)	0.1532 (2)	0.0500 (4)
H8	−0.0435	0.1456	0.1040	0.060*
C9	−0.06185 (15)	0.31447 (17)	0.1569 (2)	0.0583 (5)
H9	−0.1284	0.3253	0.1091	0.070*
C10	−0.01684 (16)	0.40383 (17)	0.2286 (3)	0.0609 (5)
H10	−0.0527	0.4749	0.2303	0.073*
C11	0.08457 (15)	0.38906 (15)	0.3007 (2)	0.0530 (4)
C12	0.1337 (2)	0.47978 (17)	0.3771 (3)	0.0687 (6)
H12	0.0984	0.5511	0.3805	0.082*
C13	0.2316 (2)	0.46537 (17)	0.4458 (3)	0.0744 (6)
H13	0.2618	0.5261	0.4968	0.089*
C14	0.28733 (17)	0.35946 (17)	0.4400 (3)	0.0630 (5)
H14	0.3550	0.3504	0.4859	0.076*
C15	0.24238 (16)	0.26941 (14)	0.3671 (2)	0.0508 (4)
H15	0.2803	0.1995	0.3636	0.061*
C16	0.13946 (13)	0.28016 (13)	0.29679 (17)	0.0443 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0746 (9)	0.0685 (8)	0.0640 (9)	−0.0070 (7)	0.0230 (8)	0.0016 (8)
N1	0.0558 (8)	0.0455 (7)	0.0460 (8)	0.0049 (6)	−0.0107 (7)	−0.0054 (7)
C1	0.0484 (8)	0.0510 (8)	0.0419 (8)	0.0012 (7)	0.0005 (7)	0.0008 (7)
C2	0.0614 (10)	0.0588 (9)	0.0513 (10)	0.0102 (8)	−0.0018 (8)	−0.0113 (9)
C3	0.0658 (11)	0.0534 (10)	0.0793 (14)	−0.0043 (8)	0.0012 (11)	−0.0181 (10)
C4	0.0556 (10)	0.0691 (13)	0.0995 (19)	−0.0144 (9)	0.0103 (12)	−0.0260 (13)
C5	0.0532 (9)	0.0604 (10)	0.0595 (11)	−0.0051 (8)	0.0087 (9)	−0.0113 (9)
C6	0.0478 (7)	0.0490 (8)	0.0407 (9)	0.0029 (6)	−0.0057 (7)	−0.0039 (7)
C7	0.0445 (7)	0.0460 (8)	0.0389 (8)	0.0010 (6)	0.0033 (7)	0.0017 (7)
C8	0.0462 (8)	0.0537 (9)	0.0501 (10)	−0.0019 (7)	−0.0029 (7)	0.0006 (8)
C9	0.0486 (9)	0.0647 (10)	0.0616 (11)	0.0069 (8)	−0.0053 (9)	0.0068 (10)
C10	0.0596 (10)	0.0545 (10)	0.0684 (12)	0.0133 (8)	0.0016 (10)	0.0020 (9)
C11	0.0580 (9)	0.0501 (8)	0.0508 (10)	0.0029 (7)	0.0059 (8)	−0.0026 (8)
C12	0.0814 (13)	0.0501 (9)	0.0747 (15)	0.0058 (9)	−0.0010 (12)	−0.0125 (10)
C13	0.0828 (15)	0.0594 (10)	0.0811 (15)	−0.0082 (10)	−0.0099 (13)	−0.0226 (12)
C14	0.0622 (10)	0.0653 (10)	0.0616 (11)	−0.0076 (9)	−0.0105 (9)	−0.0066 (10)
C15	0.0516 (8)	0.0516 (8)	0.0491 (9)	−0.0001 (8)	−0.0023 (8)	−0.0023 (8)
C16	0.0478 (8)	0.0466 (8)	0.0385 (8)	−0.0007 (6)	0.0044 (7)	−0.0003 (7)

O1—C1	1.428 (2)	C6—H6	0.9800
O1—H1O	0.8200	C7—C8	1.377 (2)
N1—C7	1.398 (2)	C7—C16	1.433 (2)
N1—C6	1.454 (2)	C8—C9	1.406 (2)
N1—H1N	0.83 (3)	C8—H8	0.9300
C1—C2	1.509 (2)	C9—C10	1.355 (3)
C1—C6	1.526 (2)	C9—H9	0.9300
C1—H1	0.9800	C10—C11	1.411 (3)
C2—C3	1.514 (3)	C10—H10	0.9300
C2—H2A	0.9700	C11—C12	1.410 (3)
C2—H2B	0.9700	C11—C16	1.425 (2)
C3—C4	1.523 (3)	C12—C13	1.359 (4)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.399 (3)
C4—C5	1.526 (3)	C13—H13	0.9300
C4—H4A	0.9700	C14—C15	1.367 (3)
C4—H4B	0.9700	C14—H14	0.9300
C5—C6	1.519 (3)	C15—C16	1.414 (3)
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700
C1—O1—H1O	109.5	N1—C6—C1	107.38 (13)
C7—N1—C6	122.71 (14)	C5—C6—C1	110.50 (13)
C7—N1—H1N	113.6 (15)	N1—C6—H6	108.0
C6—N1—H1N	110.9 (14)	C5—C6—H6	108.0
O1—C1—C2	109.60 (16)	C1—C6—H6	108.0
O1—C1—C6	110.40 (13)	C8—C7—N1	122.87 (15)
C2—C1—C6	110.94 (14)	C8—C7—C16	119.24 (15)
O1—C1—H1	108.6	N1—C7—C16	117.81 (14)
C2—C1—H1	108.6	C7—C8—C9	120.67 (17)
C6—C1—H1	108.6	C7—C8—H8	119.7
C1—C2—C3	110.28 (17)	C9—C8—H8	119.7
C1—C2—H2A	109.6	C10—C9—C8	121.51 (17)
C3—C2—H2A	109.6	C10—C9—H9	119.2
C1—C2—H2B	109.6	C8—C9—H9	119.2
C3—C2—H2B	109.6	C9—C10—C11	119.97 (17)
H2A—C2—H2B	108.1	C9—C10—H10	120.0
C2—C3—C4	110.83 (17)	C11—C10—H10	120.0
C2—C3—H3A	109.5	C12—C11—C10	121.65 (17)
C4—C3—H3A	109.5	C12—C11—C16	118.67 (18)
C2—C3—H3B	109.5	C10—C11—C16	119.68 (16)
C4—C3—H3B	109.5	C13—C12—C11	121.47 (19)
H3A—C3—H3B	108.1	C13—C12—H12	119.3
C3—C4—C5	111.45 (16)	C11—C12—H12	119.3
C3—C4—H4A	109.3	C12—C13—C14	120.24 (19)
C5—C4—H4A	109.3	C12—C13—H13	119.9
C3—C4—H4B	109.3	C14—C13—H13	119.9
C5—C4—H4B	109.3	C15—C14—C13	120.04 (19)
H4A—C4—H4B	108.0	C15—C14—H14	120.0
C6—C5—C4	111.16 (18)	C13—C14—H14	120.0
C6—C5—H5A	109.4	C14—C15—C16	121.42 (17)
C4—C5—H5A	109.4	C14—C15—H15	119.3
C6—C5—H5B	109.4	C16—C15—H15	119.3
C4—C5—H5B	109.4	C15—C16—C11	118.12 (15)
H5A—C5—H5B	108.0	C15—C16—C7	122.96 (14)
N1—C6—C5	114.69 (15)	C11—C16—C7	118.92 (15)

Cg1 is the centroid of the C7–C11/C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (3)	2.30 (3)	3.125 (2)	171 (2)
C14—H14···Cg1i	0.93	2.71	3.530 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C11/C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (3)	2.30 (3)	3.125 (2)	171 (2)
C14—H14⋯Cg1i	0.93	2.71	3.530 (3)	148

Symmetry code: (i) .