2-tert-Butyl-4-methyl-6-(4-piperidyl­methyl)­phenol

In the title compound, C₁₇H₂₇NO, the piperidine ring is folded into the normal chair conformation. There exists an intramolecular O—H...N hydrogen bond involving the N-donor of the piperidine ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.155
• Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

2-tert-Butyl-4-methyl-6-(4-piperidylmethyl)phenol

Crystal data

C17H27NO	Z = 2
Mr = 261.40	F(000) = 288
Triclinic, P1	Dx = 1.086 Mg m^−3
a = 6.2854 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.626 (3) Å	Cell parameters from 3312 reflections
c = 15.318 (5) Å	θ = 1.4–25.0°
α = 97.391 (6)°	µ = 0.07 mm^−1
β = 97.498 (6)°	T = 293 K
γ = 100.559 (7)°	Prism, colorless
V = 799.5 (4) Å^3	0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 diffractometer	1219 reflections with I > 2σ(I)
ω scans	Rint = 0.040
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]	θmax = 25.0°
Tmin = 0.984, Tmax = 0.987	h = −6→7
3376 measured reflections	k = −7→10
2818 independent reflections	l = −18→18

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.0223P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.155	(Δ/σ)max = 0.022
S = 0.99	Δρmax = 0.16 e Å^−3
2818 reflections	Δρmin = −0.18 e Å^−3
172 parameters

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. Full-MATRIX

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.0386 (4)	0.3200 (3)	0.16721 (17)	0.0448 (7)
O1	0.2393 (3)	0.5997 (2)	0.21525 (14)	0.0541 (7)
H1A	0.1197	0.5412	0.1958	0.081*
C1	0.0702 (5)	0.2173 (4)	0.1130 (2)	0.0519 (9)
H1B	0.0198	0.1071	0.1202	0.062*
H1C	0.2270	0.2456	0.1333	0.062*
C2	0.0232 (5)	0.2334 (4)	0.0156 (2)	0.0619 (10)
H2A	0.0923	0.1605	−0.0191	0.074*
H2B	0.0857	0.3412	0.0078	0.074*
C3	−0.2215 (5)	0.1971 (5)	−0.0183 (2)	0.0692 (11)
H3A	−0.2479	0.2208	−0.0785	0.083*
H3B	−0.2809	0.0847	−0.0195	0.083*
C4	−0.3338 (5)	0.2974 (5)	0.0424 (2)	0.0692 (11)
H4A	−0.2904	0.4088	0.0361	0.083*
H4B	−0.4913	0.2658	0.0243	0.083*
C5	−0.2765 (5)	0.2791 (4)	0.1390 (2)	0.0589 (10)
H5A	−0.3457	0.3485	0.1761	0.071*
H5B	−0.3316	0.1699	0.1466	0.071*
C6	0.0165 (5)	0.3119 (4)	0.2623 (2)	0.0502 (9)
H6A	−0.0109	0.2009	0.2707	0.060*
H6B	−0.0792	0.3650	0.2949	0.060*
C7	0.2521 (5)	0.3879 (4)	0.3008 (2)	0.0400 (8)
C8	0.3497 (5)	0.5335 (4)	0.2794 (2)	0.0412 (8)
C9	0.5594 (5)	0.6144 (4)	0.32101 (19)	0.0410 (8)
C10	0.6646 (5)	0.5395 (4)	0.3834 (2)	0.0448 (9)
H10A	0.8031	0.5914	0.4129	0.054*
C11	0.5767 (5)	0.3919 (4)	0.40477 (19)	0.0424 (8)
C12	0.3690 (5)	0.3189 (4)	0.3625 (2)	0.0470 (9)
H12A	0.3054	0.2204	0.3758	0.056*
C13	0.7032 (5)	0.3160 (4)	0.4718 (2)	0.0651 (11)
H13A	0.6169	0.2151	0.4779	0.098*
H13B	0.7364	0.3848	0.5283	0.098*
H13C	0.8372	0.2996	0.4518	0.098*
C14	0.6678 (5)	0.7764 (4)	0.2997 (2)	0.0471 (9)
C15	0.8877 (6)	0.8454 (4)	0.3604 (2)	0.0823 (13)
H15A	0.9841	0.7717	0.3540	0.123*
H15B	0.8642	0.8628	0.4213	0.123*
H15C	0.9525	0.9450	0.3440	0.123*
C16	0.7130 (5)	0.7574 (4)	0.2037 (2)	0.0677 (11)
H16A	0.5778	0.7155	0.1638	0.102*
H16B	0.8113	0.6852	0.1967	0.102*
H16C	0.7783	0.8595	0.1904	0.102*
C17	0.5191 (5)	0.8979 (4)	0.3124 (2)	0.0701 (11)
H17A	0.3806	0.8586	0.2743	0.105*
H17B	0.5876	0.9978	0.2974	0.105*
H17C	0.4962	0.9132	0.3734	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0307 (16)	0.0490 (18)	0.0523 (18)	0.0066 (13)	0.0065 (12)	0.0013 (13)
O1	0.0441 (14)	0.0503 (15)	0.0651 (16)	0.0051 (12)	−0.0010 (11)	0.0152 (12)
C1	0.044 (2)	0.061 (2)	0.050 (2)	0.0112 (19)	0.0068 (16)	0.0048 (18)
C2	0.050 (2)	0.075 (3)	0.057 (2)	0.008 (2)	0.0091 (18)	0.0027 (19)
C3	0.053 (2)	0.092 (3)	0.055 (2)	0.004 (2)	−0.0031 (19)	0.013 (2)
C4	0.043 (2)	0.081 (3)	0.082 (3)	0.012 (2)	0.000 (2)	0.017 (2)
C5	0.038 (2)	0.071 (3)	0.065 (3)	0.0091 (19)	0.0048 (17)	0.009 (2)
C6	0.049 (2)	0.056 (2)	0.043 (2)	0.0032 (18)	0.0107 (16)	0.0027 (17)
C7	0.041 (2)	0.036 (2)	0.040 (2)	0.0015 (17)	0.0099 (16)	0.0009 (16)
C8	0.042 (2)	0.044 (2)	0.038 (2)	0.0163 (18)	0.0016 (16)	0.0060 (16)
C9	0.042 (2)	0.039 (2)	0.039 (2)	0.0054 (17)	0.0051 (16)	0.0008 (16)
C10	0.041 (2)	0.050 (2)	0.040 (2)	0.0076 (18)	0.0016 (16)	0.0017 (17)
C11	0.049 (2)	0.043 (2)	0.0346 (19)	0.0128 (18)	0.0046 (16)	0.0027 (16)
C12	0.060 (2)	0.040 (2)	0.043 (2)	0.0096 (19)	0.0145 (18)	0.0077 (17)
C13	0.078 (3)	0.071 (3)	0.050 (2)	0.025 (2)	0.0013 (19)	0.018 (2)
C14	0.043 (2)	0.043 (2)	0.054 (2)	0.0051 (18)	0.0054 (17)	0.0107 (17)
C15	0.069 (3)	0.063 (3)	0.096 (3)	−0.017 (2)	−0.014 (2)	0.017 (2)
C16	0.062 (2)	0.069 (3)	0.077 (3)	0.011 (2)	0.018 (2)	0.029 (2)
C17	0.076 (3)	0.043 (2)	0.092 (3)	0.011 (2)	0.019 (2)	0.008 (2)

Geometric parameters (Å, º)

N1—C1	1.457 (4)	C8—C9	1.400 (4)
N1—C5	1.464 (3)	C9—C10	1.385 (4)
N1—C6	1.466 (4)	C9—C14	1.532 (4)
O1—C8	1.372 (3)	C10—C11	1.389 (4)
O1—H1A	0.8200	C10—H10A	0.9300
C1—C2	1.512 (4)	C11—C12	1.376 (4)
C1—H1B	0.9700	C11—C13	1.505 (4)
C1—H1C	0.9700	C12—H12A	0.9300
C2—C3	1.519 (4)	C13—H13A	0.9600
C2—H2A	0.9700	C13—H13B	0.9600
C2—H2B	0.9700	C13—H13C	0.9600
C3—C4	1.516 (5)	C14—C16	1.527 (4)
C3—H3A	0.9700	C14—C15	1.533 (4)
C3—H3B	0.9700	C14—C17	1.538 (4)
C4—C5	1.513 (4)	C15—H15A	0.9600
C4—H4A	0.9700	C15—H15B	0.9600
C4—H4B	0.9700	C15—H15C	0.9600
C5—H5A	0.9700	C16—H16A	0.9600
C5—H5B	0.9700	C16—H16B	0.9600
C6—C7	1.513 (4)	C16—H16C	0.9600
C6—H6A	0.9700	C17—H17A	0.9600
C6—H6B	0.9700	C17—H17B	0.9600
C7—C12	1.382 (4)	C17—H17C	0.9600
C7—C8	1.392 (4)
C1—N1—C5	110.9 (2)	O1—C8—C9	118.7 (3)
C1—N1—C6	111.4 (2)	C7—C8—C9	121.7 (3)
C5—N1—C6	110.5 (2)	C10—C9—C8	116.0 (3)
C8—O1—H1A	109.5	C10—C9—C14	121.5 (3)
N1—C1—C2	111.1 (3)	C8—C9—C14	122.5 (3)
N1—C1—H1B	109.4	C9—C10—C11	124.3 (3)
C2—C1—H1B	109.4	C9—C10—H10A	117.9
N1—C1—H1C	109.4	C11—C10—H10A	117.9
C2—C1—H1C	109.4	C12—C11—C10	117.1 (3)
H1B—C1—H1C	108.0	C12—C11—C13	121.6 (3)
C1—C2—C3	111.4 (3)	C10—C11—C13	121.3 (3)
C1—C2—H2A	109.4	C11—C12—C7	121.9 (3)
C3—C2—H2A	109.4	C11—C12—H12A	119.1
C1—C2—H2B	109.4	C7—C12—H12A	119.1
C3—C2—H2B	109.4	C11—C13—H13A	109.5
H2A—C2—H2B	108.0	C11—C13—H13B	109.5
C4—C3—C2	109.5 (3)	H13A—C13—H13B	109.5
C4—C3—H3A	109.8	C11—C13—H13C	109.5
C2—C3—H3A	109.8	H13A—C13—H13C	109.5
C4—C3—H3B	109.8	H13B—C13—H13C	109.5
C2—C3—H3B	109.8	C16—C14—C9	109.8 (3)
H3A—C3—H3B	108.2	C16—C14—C15	107.4 (3)
C5—C4—C3	111.9 (3)	C9—C14—C15	111.9 (3)
C5—C4—H4A	109.2	C16—C14—C17	109.6 (3)
C3—C4—H4A	109.2	C9—C14—C17	110.5 (3)
C5—C4—H4B	109.2	C15—C14—C17	107.6 (3)
C3—C4—H4B	109.2	C14—C15—H15A	109.5
H4A—C4—H4B	107.9	C14—C15—H15B	109.5
N1—C5—C4	110.5 (3)	H15A—C15—H15B	109.5
N1—C5—H5A	109.6	C14—C15—H15C	109.5
C4—C5—H5A	109.6	H15A—C15—H15C	109.5
N1—C5—H5B	109.6	H15B—C15—H15C	109.5
C4—C5—H5B	109.6	C14—C16—H16A	109.5
H5A—C5—H5B	108.1	C14—C16—H16B	109.5
N1—C6—C7	113.4 (2)	H16A—C16—H16B	109.5
N1—C6—H6A	108.9	C14—C16—H16C	109.5
C7—C6—H6A	108.9	H16A—C16—H16C	109.5
N1—C6—H6B	108.9	H16B—C16—H16C	109.5
C7—C6—H6B	108.9	C14—C17—H17A	109.5
H6A—C6—H6B	107.7	C14—C17—H17B	109.5
C12—C7—C8	119.0 (3)	H17A—C17—H17B	109.5
C12—C7—C6	120.3 (3)	C14—C17—H17C	109.5
C8—C7—C6	120.6 (3)	H17A—C17—H17C	109.5
O1—C8—C7	119.5 (3)	H17B—C17—H17C	109.5
C5—N1—C1—C2	59.8 (3)	C7—C8—C9—C10	1.1 (4)
C6—N1—C1—C2	−176.7 (3)	O1—C8—C9—C14	1.8 (4)
N1—C1—C2—C3	−56.6 (4)	C7—C8—C9—C14	−178.7 (3)
C1—C2—C3—C4	52.5 (4)	C8—C9—C10—C11	1.1 (4)
C2—C3—C4—C5	−52.9 (4)	C14—C9—C10—C11	−179.1 (3)
C1—N1—C5—C4	−59.5 (4)	C9—C10—C11—C12	−1.9 (5)
C6—N1—C5—C4	176.5 (3)	C9—C10—C11—C13	178.5 (3)
C3—C4—C5—N1	56.6 (4)	C10—C11—C12—C7	0.5 (4)
C1—N1—C6—C7	69.3 (3)	C13—C11—C12—C7	−179.9 (3)
C5—N1—C6—C7	−166.9 (3)	C8—C7—C12—C11	1.6 (4)
N1—C6—C7—C12	−141.2 (3)	C6—C7—C12—C11	−174.2 (3)
N1—C6—C7—C8	43.1 (4)	C10—C9—C14—C16	114.1 (3)
C12—C7—C8—O1	177.0 (3)	C8—C9—C14—C16	−66.0 (4)
C6—C7—C8—O1	−7.2 (4)	C10—C9—C14—C15	−5.0 (4)
C12—C7—C8—C9	−2.4 (4)	C8—C9—C14—C15	174.9 (3)
C6—C7—C8—C9	173.3 (3)	C10—C9—C14—C17	−124.8 (3)
O1—C8—C9—C10	−178.4 (3)	C8—C9—C14—C17	55.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1a···N1	0.82	1.95	2.660 (3)	145