4-(4-Chloro-phen-yl)piperidin-4-ol.

In the title compound, C(11)H(14)ClNO, the piperidine ring adopts a chair conformation: the hydroxyl substituent and the N-bound H atom occupy the axial positions, while the benzene ring occupies the equatorial position. In the crystal, the mol-ecules are linked into a centrosymmetric tetra-mer through strong O-H⋯N and weak N-H⋯O hydrogen bonds; the N and O atoms act as both donor and acceptor for these inter-actions. The tetra-mers are further joined by hydrogen bonds into a layer parallel to (100).

Related literature

For related structures, see: De Camp & Ahmed (1972a ▶,b ▶); Friederich et al. (1993 ▶); Kimura & Okabayashi (1986 ▶). For details of the asymmetry parameters for chair conformations, see: Duax & Norton (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C11H14ClNO

M = 211.68

Monoclinic,

a = 11.3706 (10) Å

b = 9.5204 (8) Å

c = 10.6164 (9) Å

β = 108.458 (8)°

V = 1090.13 (16) Å3

Z = 4

Cu Kα radiation

μ = 2.83 mm−1

T = 295 K

0.3 × 0.2 × 0.15 mm

Data collection

Oxford Diffraction SuperNova, single source at offset, Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.401, T max = 0.654

4068 measured reflections

2190 independent reflections

2014 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.07

2190 reflections

183 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004216/is2520sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004216/is2520Isup2.hkl

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

C11H14ClNO	F(000) = 448
Mr = 211.68	Dx = 1.290 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3304 reflections
a = 11.3706 (10) Å	θ = 4.1–75.2°
b = 9.5204 (8) Å	µ = 2.83 mm−1
c = 10.6164 (9) Å	T = 295 K
β = 108.458 (8)°	Prism, yellow
V = 1090.13 (16) Å3	0.3 × 0.2 × 0.15 mm
Z = 4

Oxford Diffraction SuperNova, single source at offset, Atlas diffractometer	2190 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2014 reflections with I > 2σ(I)
mirror	Rint = 0.011
Detector resolution: 10.5357 pixels mm-1	θmax = 75.3°, θmin = 4.1°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→7
Tmin = 0.401, Tmax = 0.654	l = −12→13
4068 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.250P] where P = (Fo2 + 2Fc2)/3
2190 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.92832 (13)	0.42199 (14)	0.33836 (13)	0.0530 (3)
H1	0.8930 (19)	0.430 (2)	0.402 (2)	0.069 (5)*
C2	0.83116 (16)	0.40784 (17)	0.20917 (16)	0.0537 (4)
H21	0.8738 (17)	0.4069 (19)	0.1413 (18)	0.058 (5)*
H22	0.7767 (18)	0.491 (2)	0.1973 (18)	0.065 (5)*
C3	0.75467 (14)	0.27404 (16)	0.19461 (16)	0.0507 (3)
H31	0.7086 (19)	0.277 (2)	0.255 (2)	0.072 (6)*
H32	0.6977 (17)	0.2675 (19)	0.0997 (19)	0.061 (5)*
C4	0.83678 (12)	0.14272 (14)	0.22350 (12)	0.0414 (3)
O4	0.89540 (10)	0.13797 (11)	0.12224 (9)	0.0476 (3)
H4A	0.949 (2)	0.073 (2)	0.140 (2)	0.074 (6)*
C5	0.93538 (14)	0.16101 (17)	0.36010 (13)	0.0462 (3)
H51	0.9930 (16)	0.0777 (19)	0.3783 (16)	0.052 (4)*
H52	0.8963 (17)	0.1649 (19)	0.4293 (18)	0.058 (5)*
C6	1.00732 (15)	0.29679 (18)	0.36784 (15)	0.0534 (4)
H61	1.0557 (17)	0.2932 (19)	0.3036 (18)	0.059 (5)*
H62	1.0676 (18)	0.307 (2)	0.457 (2)	0.066 (5)*
C41	0.75873 (12)	0.01087 (15)	0.21490 (13)	0.0433 (3)
C42	0.76509 (17)	−0.0736 (2)	0.32296 (16)	0.0604 (4)
H42	0.818 (2)	−0.051 (2)	0.409 (2)	0.080 (6)*
C43	0.69364 (19)	−0.1934 (2)	0.3105 (2)	0.0715 (5)
H43	0.699 (2)	−0.251 (2)	0.384 (2)	0.084 (6)*
C44	0.61247 (15)	−0.22890 (18)	0.18927 (19)	0.0600 (4)
Cl44	0.52022 (5)	−0.37870 (6)	0.17414 (7)	0.0901 (2)
C45	0.60313 (16)	−0.14761 (19)	0.07924 (18)	0.0601 (4)
H45	0.550 (2)	−0.174 (2)	−0.007 (2)	0.081 (6)*
C46	0.67646 (14)	−0.02996 (18)	0.09244 (15)	0.0536 (4)
H46	0.6735 (18)	0.028 (2)	0.014 (2)	0.072 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0619 (8)	0.0540 (7)	0.0485 (7)	−0.0073 (6)	0.0250 (6)	−0.0050 (5)
C2	0.0587 (9)	0.0478 (8)	0.0548 (8)	0.0021 (7)	0.0181 (7)	0.0037 (6)
C3	0.0468 (7)	0.0509 (8)	0.0539 (8)	0.0038 (6)	0.0152 (6)	0.0030 (6)
C4	0.0446 (7)	0.0485 (7)	0.0339 (6)	0.0023 (5)	0.0163 (5)	0.0033 (5)
O4	0.0558 (6)	0.0550 (6)	0.0377 (5)	0.0044 (5)	0.0227 (4)	0.0064 (4)
C5	0.0492 (7)	0.0539 (8)	0.0356 (6)	−0.0010 (6)	0.0136 (5)	0.0032 (5)
C6	0.0508 (8)	0.0627 (9)	0.0451 (7)	−0.0073 (7)	0.0129 (6)	−0.0003 (7)
C41	0.0435 (6)	0.0479 (7)	0.0407 (6)	0.0032 (6)	0.0167 (5)	0.0004 (5)
C42	0.0649 (10)	0.0668 (10)	0.0459 (8)	−0.0133 (8)	0.0123 (7)	0.0086 (7)
C43	0.0746 (11)	0.0722 (12)	0.0672 (10)	−0.0159 (9)	0.0216 (9)	0.0162 (9)
C44	0.0495 (8)	0.0533 (9)	0.0805 (11)	−0.0037 (7)	0.0253 (8)	−0.0041 (8)
Cl44	0.0732 (3)	0.0695 (3)	0.1295 (5)	−0.0240 (2)	0.0349 (3)	−0.0071 (3)
C45	0.0515 (8)	0.0656 (10)	0.0609 (9)	−0.0039 (7)	0.0145 (7)	−0.0124 (8)
C46	0.0540 (8)	0.0600 (9)	0.0453 (7)	−0.0006 (7)	0.0138 (6)	−0.0004 (7)

N1—C6	1.465 (2)	C5—H52	0.972 (19)
N1—C2	1.470 (2)	C6—H61	1.003 (19)
N1—H1	0.89 (2)	C6—H62	0.99 (2)
C2—C3	1.522 (2)	C41—C42	1.384 (2)
C2—H21	0.987 (19)	C41—C46	1.395 (2)
C2—H22	0.99 (2)	C42—C43	1.382 (3)
C3—C4	1.5322 (19)	C42—H42	0.95 (2)
C3—H31	0.95 (2)	C43—C44	1.368 (3)
C3—H32	1.013 (18)	C43—H43	0.94 (2)
C4—O4	1.4337 (15)	C44—C45	1.377 (3)
C4—C41	1.5233 (19)	C44—Cl44	1.7473 (17)
C4—C5	1.5365 (18)	C45—C46	1.377 (2)
O4—H4A	0.84 (2)	C45—H45	0.96 (2)
C5—C6	1.518 (2)	C46—H46	0.99 (2)
C5—H51	1.008 (17)
C6—N1—C2	110.71 (12)	C4—C5—H52	110.2 (11)
C6—N1—H1	107.4 (13)	H51—C5—H52	108.1 (14)
C2—N1—H1	109.3 (13)	N1—C6—C5	113.44 (13)
N1—C2—C3	114.07 (13)	N1—C6—H61	108.3 (10)
N1—C2—H21	106.5 (10)	C5—C6—H61	109.6 (10)
C3—C2—H21	108.4 (11)	N1—C6—H62	108.6 (11)
N1—C2—H22	107.6 (11)	C5—C6—H62	109.5 (11)
C3—C2—H22	110.0 (11)	H61—C6—H62	107.2 (15)
H21—C2—H22	110.3 (15)	C42—C41—C46	117.02 (14)
C2—C3—C4	111.72 (12)	C42—C41—C4	123.54 (13)
C2—C3—H31	109.2 (13)	C46—C41—C4	119.44 (12)
C4—C3—H31	108.6 (12)	C43—C42—C41	121.70 (15)
C2—C3—H32	108.5 (10)	C43—C42—H42	117.1 (13)
C4—C3—H32	107.8 (10)	C41—C42—H42	121.2 (13)
H31—C3—H32	111.1 (15)	C44—C43—C42	119.67 (16)
O4—C4—C41	109.23 (10)	C44—C43—H43	119.2 (14)
O4—C4—C3	105.91 (11)	C42—C43—H43	121.1 (14)
C41—C4—C3	110.72 (11)	C43—C44—C45	120.47 (16)
O4—C4—C5	109.74 (11)	C43—C44—Cl44	119.66 (14)
C41—C4—C5	112.78 (11)	C45—C44—Cl44	119.87 (14)
C3—C4—C5	108.23 (12)	C46—C45—C44	119.30 (15)
C4—O4—H4A	109.3 (14)	C46—C45—H45	119.4 (13)
C6—C5—C4	111.55 (12)	C44—C45—H45	121.3 (13)
C6—C5—H51	110.7 (10)	C45—C46—C41	121.82 (15)
C4—C5—H51	109.1 (9)	C45—C46—H46	120.8 (12)
C6—C5—H52	107.1 (11)	C41—C46—H46	117.4 (12)
C6—N1—C2—C3	53.23 (17)	O4—C4—C41—C46	−49.35 (16)
N1—C2—C3—C4	−54.44 (18)	C3—C4—C41—C46	66.91 (16)
C2—C3—C4—O4	−64.46 (15)	C5—C4—C41—C46	−171.65 (13)
C2—C3—C4—C41	177.25 (12)	C46—C41—C42—C43	0.2 (3)
C2—C3—C4—C5	53.16 (15)	C4—C41—C42—C43	−179.21 (17)
O4—C4—C5—C6	60.81 (15)	C41—C42—C43—C44	−1.3 (3)
C41—C4—C5—C6	−177.17 (11)	C42—C43—C44—C45	1.2 (3)
C3—C4—C5—C6	−54.33 (15)	C42—C43—C44—Cl44	−178.91 (16)
C2—N1—C6—C5	−54.19 (16)	C43—C44—C45—C46	0.0 (3)
C4—C5—C6—N1	56.56 (16)	Cl44—C44—C45—C46	−179.90 (13)
O4—C4—C41—C42	130.07 (15)	C44—C45—C46—C41	−1.1 (3)
C3—C4—C41—C42	−113.68 (16)	C42—C41—C46—C45	1.0 (2)
C5—C4—C41—C42	7.76 (19)	C4—C41—C46—C45	−179.54 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.89 (2)	2.41 (2)	3.2036 (16)	147.2 (17)
O4—H4A···N1ii	0.84 (2)	1.97 (2)	2.8089 (17)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.89 (2)	2.41 (2)	3.2036 (16)	147.2 (17)
O4—H4A⋯N1ii	0.84 (2)	1.97 (2)	2.8089 (17)	174 (2)

Symmetry codes: (i) ; (ii) .