1-(Piperidin-1-ylmethyl)-2-naphthol

The title compound, C₁₆H₁₉NO, is a product of a Mannich reaction involving 2-naphthol, formaldehyde and piperidine. The piperidine ring has a chair conformation. The molecular structure is stabilized by an intra­molecular O—H...N hydrogen bond, linking the naphthol OH group and the piperidine N atom.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.159
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1     ...       1.04 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1-Piperidin-1-ylmethyl-2-naphthol

Crystal data

C16H19NO	F(000) = 520
Mr = 241.32	Dx = 1.205 Mg m^−3
Monoclinic, P21/c	Melting point: 368 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.3262 (19) Å	Cell parameters from 1065 reflections
b = 9.360 (3) Å	θ = 2.4–21.2°
c = 22.629 (7) Å	µ = 0.08 mm^−1
β = 96.924 (5)°	T = 294 K
V = 1330.2 (7) Å^3	Block, colorless
Z = 4	0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	1152 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
Tmin = 0.981, Tmax = 0.985	k = −11→9
7229 measured reflections	l = −27→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0743P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
2702 reflections	Δρmax = 0.21 e Å^−3
168 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2041 (3)	1.0657 (2)	0.12055 (8)	0.0680 (6)
H1	0.077 (6)	0.998 (4)	0.1077 (13)	0.130 (14)*
N1	−0.0834 (3)	0.8681 (2)	0.11831 (8)	0.0524 (6)
C1	0.2553 (4)	1.0383 (3)	0.17959 (11)	0.0512 (7)
C2	0.4422 (4)	1.1033 (3)	0.20659 (12)	0.0605 (7)
H2	0.5208	1.1621	0.1843	0.073*
C3	0.5087 (4)	1.0808 (3)	0.26473 (12)	0.0619 (8)
H3	0.6337	1.1238	0.2819	0.074*
C4	0.3927 (4)	0.9934 (3)	0.29997 (11)	0.0503 (7)
C5	0.4615 (4)	0.9676 (3)	0.36056 (11)	0.0642 (8)
H5	0.5899	1.0063	0.3777	0.077*
C6	0.3447 (5)	0.8876 (3)	0.39418 (12)	0.0692 (8)
H6	0.3926	0.8716	0.4341	0.083*
C7	0.1537 (5)	0.8296 (3)	0.36921 (12)	0.0663 (8)
H7	0.0731	0.7756	0.3928	0.080*
C8	0.0814 (4)	0.8502 (3)	0.31039 (11)	0.0557 (7)
H8	−0.0479	0.8104	0.2946	0.067*
C9	0.2002 (4)	0.9312 (2)	0.27310 (10)	0.0456 (6)
C10	0.1338 (4)	0.9526 (2)	0.21145 (10)	0.0457 (6)
C11	−0.0756 (4)	0.8906 (3)	0.18299 (10)	0.0671 (8)
H11A	−0.0996	0.7999	0.2018	0.081*
H11B	−0.1902	0.9545	0.1904	0.081*
C12	−0.3033 (4)	0.8600 (3)	0.09029 (11)	0.0687 (8)
H12A	−0.3784	0.9464	0.0990	0.082*
H12B	−0.3739	0.7797	0.1066	0.082*
C13	−0.3124 (5)	0.8424 (3)	0.02356 (11)	0.0725 (8)
H13A	−0.4596	0.8341	0.0061	0.087*
H13B	−0.2519	0.9262	0.0068	0.087*
C14	−0.1905 (4)	0.7111 (3)	0.00854 (11)	0.0695 (8)
H14A	−0.2608	0.6261	0.0210	0.083*
H14B	−0.1873	0.7058	−0.0342	0.083*
C15	0.0336 (4)	0.7180 (3)	0.03974 (11)	0.0717 (8)
H15A	0.1089	0.7963	0.0235	0.086*
H15B	0.1077	0.6301	0.0326	0.086*
C16	0.0344 (4)	0.7394 (3)	0.10596 (11)	0.0614 (7)
H16A	−0.0297	0.6570	0.1228	0.074*
H16B	0.1802	0.7473	0.1247	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0847 (14)	0.0650 (13)	0.0560 (12)	0.0002 (11)	0.0154 (10)	0.0157 (10)
N1	0.0450 (13)	0.0654 (15)	0.0469 (13)	0.0081 (11)	0.0057 (9)	−0.0030 (10)
C1	0.0608 (17)	0.0472 (16)	0.0476 (16)	0.0065 (13)	0.0140 (13)	0.0045 (13)
C2	0.0689 (19)	0.0479 (17)	0.0694 (19)	−0.0133 (14)	0.0273 (14)	−0.0021 (14)
C3	0.0603 (17)	0.0571 (18)	0.0695 (19)	−0.0146 (14)	0.0130 (15)	−0.0113 (15)
C4	0.0541 (16)	0.0457 (16)	0.0519 (16)	0.0001 (12)	0.0104 (12)	−0.0096 (12)
C5	0.0672 (19)	0.0622 (19)	0.0614 (19)	−0.0026 (15)	0.0002 (15)	−0.0108 (15)
C6	0.089 (2)	0.069 (2)	0.0496 (17)	0.0043 (17)	0.0066 (16)	−0.0068 (15)
C7	0.085 (2)	0.0624 (19)	0.0560 (18)	−0.0036 (16)	0.0257 (15)	0.0001 (14)
C8	0.0618 (17)	0.0549 (17)	0.0532 (17)	−0.0079 (13)	0.0186 (13)	−0.0051 (14)
C9	0.0509 (15)	0.0401 (14)	0.0482 (15)	0.0010 (12)	0.0155 (12)	−0.0070 (12)
C10	0.0466 (14)	0.0443 (15)	0.0477 (15)	0.0036 (12)	0.0125 (12)	−0.0013 (12)
C11	0.0549 (17)	0.093 (2)	0.0546 (17)	−0.0009 (15)	0.0128 (13)	−0.0070 (15)
C12	0.0536 (17)	0.087 (2)	0.0644 (19)	0.0124 (15)	0.0012 (13)	−0.0073 (16)
C13	0.0713 (19)	0.083 (2)	0.0603 (18)	0.0088 (16)	−0.0039 (14)	0.0043 (16)
C14	0.080 (2)	0.077 (2)	0.0514 (17)	−0.0035 (17)	0.0093 (15)	−0.0028 (15)
C15	0.074 (2)	0.074 (2)	0.069 (2)	0.0129 (15)	0.0139 (15)	−0.0117 (16)
C16	0.0561 (17)	0.0611 (18)	0.0662 (18)	0.0102 (13)	0.0039 (13)	0.0013 (14)

Geometric parameters (Å, º)

O1—C1	1.360 (3)	C8—H8	0.9300
O1—H1	1.04 (4)	C9—C10	1.422 (3)
N1—C12	1.460 (3)	C10—C11	1.517 (3)
N1—C16	1.462 (3)	C11—H11A	0.9700
N1—C11	1.474 (3)	C11—H11B	0.9700
C1—C10	1.374 (3)	C12—C13	1.513 (3)
C1—C2	1.403 (3)	C12—H12A	0.9700
C2—C3	1.348 (3)	C12—H12B	0.9700
C2—H2	0.9300	C13—C14	1.511 (3)
C3—C4	1.408 (3)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.409 (3)	C14—C15	1.507 (3)
C4—C9	1.419 (3)	C14—H14A	0.9700
C5—C6	1.350 (4)	C14—H14B	0.9700
C5—H5	0.9300	C15—C16	1.511 (3)
C6—C7	1.382 (4)	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C7—C8	1.368 (3)	C16—H16A	0.9700
C7—H7	0.9300	C16—H16B	0.9700
C8—C9	1.415 (3)
C1—O1—H1	104.2 (17)	N1—C11—H11A	108.9
C12—N1—C16	110.8 (2)	C10—C11—H11A	108.9
C12—N1—C11	110.80 (17)	N1—C11—H11B	108.9
C16—N1—C11	110.53 (19)	C10—C11—H11B	108.9
O1—C1—C10	122.9 (2)	H11A—C11—H11B	107.7
O1—C1—C2	115.8 (2)	N1—C12—C13	111.0 (2)
C10—C1—C2	121.3 (2)	N1—C12—H12A	109.4
C3—C2—C1	120.3 (2)	C13—C12—H12A	109.4
C3—C2—H2	119.8	N1—C12—H12B	109.4
C1—C2—H2	119.8	C13—C12—H12B	109.4
C2—C3—C4	121.4 (2)	H12A—C12—H12B	108.0
C2—C3—H3	119.3	C14—C13—C12	110.7 (2)
C4—C3—H3	119.3	C14—C13—H13A	109.5
C3—C4—C5	122.0 (2)	C12—C13—H13A	109.5
C3—C4—C9	118.3 (2)	C14—C13—H13B	109.5
C5—C4—C9	119.7 (2)	C12—C13—H13B	109.5
C6—C5—C4	121.2 (3)	H13A—C13—H13B	108.1
C6—C5—H5	119.4	C15—C14—C13	109.7 (2)
C4—C5—H5	119.4	C15—C14—H14A	109.7
C5—C6—C7	119.9 (3)	C13—C14—H14A	109.7
C5—C6—H6	120.0	C15—C14—H14B	109.7
C7—C6—H6	120.0	C13—C14—H14B	109.7
C8—C7—C6	121.0 (3)	H14A—C14—H14B	108.2
C8—C7—H7	119.5	C14—C15—C16	111.2 (2)
C6—C7—H7	119.5	C14—C15—H15A	109.4
C7—C8—C9	121.1 (2)	C16—C15—H15A	109.4
C7—C8—H8	119.4	C14—C15—H15B	109.4
C9—C8—H8	119.4	C16—C15—H15B	109.4
C8—C9—C4	117.0 (2)	H15A—C15—H15B	108.0
C8—C9—C10	123.0 (2)	N1—C16—C15	111.0 (2)
C4—C9—C10	119.9 (2)	N1—C16—H16A	109.4
C1—C10—C9	118.7 (2)	C15—C16—H16A	109.4
C1—C10—C11	121.0 (2)	N1—C16—H16B	109.4
C9—C10—C11	120.1 (2)	C15—C16—H16B	109.4
N1—C11—C10	113.5 (2)	H16A—C16—H16B	108.0
O1—C1—C2—C3	−178.8 (2)	O1—C1—C10—C11	−4.2 (4)
C10—C1—C2—C3	1.0 (4)	C2—C1—C10—C11	176.0 (2)
C1—C2—C3—C4	−0.6 (4)	C8—C9—C10—C1	177.0 (2)
C2—C3—C4—C5	179.2 (2)	C4—C9—C10—C1	−2.3 (3)
C2—C3—C4—C9	−1.2 (4)	C8—C9—C10—C11	1.5 (4)
C3—C4—C5—C6	177.7 (2)	C4—C9—C10—C11	−177.9 (2)
C9—C4—C5—C6	−1.9 (4)	C12—N1—C11—C10	−159.1 (2)
C4—C5—C6—C7	0.0 (4)	C16—N1—C11—C10	77.7 (3)
C5—C6—C7—C8	0.8 (4)	C1—C10—C11—N1	28.5 (3)
C6—C7—C8—C9	0.3 (4)	C9—C10—C11—N1	−156.0 (2)
C7—C8—C9—C4	−2.1 (3)	C16—N1—C12—C13	−59.0 (3)
C7—C8—C9—C10	178.5 (2)	C11—N1—C12—C13	177.9 (2)
C3—C4—C9—C8	−176.7 (2)	N1—C12—C13—C14	57.3 (3)
C5—C4—C9—C8	2.9 (3)	C12—C13—C14—C15	−54.5 (3)
C3—C4—C9—C10	2.7 (3)	C13—C14—C15—C16	54.4 (3)
C5—C4—C9—C10	−177.7 (2)	C12—N1—C16—C15	58.7 (3)
O1—C1—C10—C9	−179.7 (2)	C11—N1—C16—C15	−178.1 (2)
C2—C1—C10—C9	0.5 (4)	C14—C15—C16—N1	−56.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.04 (4)	1.62 (4)	2.590 (3)	153 (3)