4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium 2-(2-phenyl-eth-yl)benzoate.

In the title compound, C(11)H(15)ClNO(+)·C(15)H(13)O(2) (-), the piperidinium ring adopts a chair conformation. In the crystal, cations and anions are connected by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming two-dimensional networks parallel to the bc plane. Furthermore, the crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For related structures, see: Cygler et al. (1980 ▶); Cygler & Ahmed, (1984 ▶); Dutkiewicz et al. (2010 ▶); Jasinski et al. (2009 ▶, 2010 ▶); Tomlin et al. (1996 ▶). For the synthesis and biological activity of uncondensed cyclic derivatives of piperidine, see: Vartanyan (1984 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H15ClNO+·C15H13O2 −

M = 437.94

Monoclinic,

a = 13.1016 (2) Å

b = 10.2963 (2) Å

c = 16.8015 (3) Å

β = 98.234 (1)°

V = 2243.12 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.45 × 0.43 × 0.33 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.916, T max = 0.938

27219 measured reflections

8207 independent reflections

6646 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.03

8207 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023051/rz2607sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023051/rz2607Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023051/rz2607Isup3.cml

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

C11H15ClNO+·C15H13O2−	F(000) = 928
Mr = 437.94	Dx = 1.297 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9967 reflections
a = 13.1016 (2) Å	θ = 2.5–32.7°
b = 10.2963 (2) Å	µ = 0.20 mm−1
c = 16.8015 (3) Å	T = 100 K
β = 98.234 (1)°	Block, colourless
V = 2243.12 (7) Å3	0.45 × 0.43 × 0.33 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	8207 independent reflections
Radiation source: fine-focus sealed tube	6646 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 32.7°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.916, Tmax = 0.938	k = −15→15
27219 measured reflections	l = −25→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.5497P] where P = (Fo2 + 2Fc2)/3
8207 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.31506 (2)	0.35787 (3)	0.13139 (2)	0.03391 (8)
O1	0.00926 (5)	−0.14140 (7)	0.20489 (5)	0.02077 (15)
N1	0.03580 (6)	−0.41264 (8)	0.08973 (5)	0.01795 (15)
C1	0.20108 (7)	0.00102 (10)	0.08361 (6)	0.01995 (18)
H1A	0.2080	−0.0661	0.0460	0.024*
C2	0.25545 (8)	0.11629 (10)	0.07964 (6)	0.02206 (19)
H2A	0.2990	0.1280	0.0396	0.026*
C3	0.24543 (8)	0.21405 (10)	0.13489 (7)	0.02213 (19)
C4	0.18101 (8)	0.19870 (10)	0.19279 (7)	0.0250 (2)
H4A	0.1737	0.2665	0.2299	0.030*
C5	0.12706 (8)	0.08269 (10)	0.19592 (6)	0.02169 (19)
H5A	0.0830	0.0720	0.2357	0.026*
C6	0.13625 (7)	−0.01800 (9)	0.14203 (6)	0.01690 (16)
C7	0.07888 (7)	−0.14634 (9)	0.14699 (6)	0.01646 (16)
C8	0.15729 (7)	−0.25735 (9)	0.16651 (6)	0.01683 (16)
H8A	0.2050	−0.2586	0.1259	0.020*
H8B	0.1985	−0.2414	0.2197	0.020*
C9	0.10419 (7)	−0.38846 (10)	0.16734 (6)	0.01883 (17)
H9A	0.1569	−0.4579	0.1765	0.023*
H9B	0.0627	−0.3910	0.2121	0.023*
C10	−0.04213 (7)	−0.30767 (10)	0.06881 (6)	0.02007 (18)
H10A	−0.0903	−0.3059	0.1091	0.024*
H10B	−0.0825	−0.3260	0.0156	0.024*
C11	0.01043 (7)	−0.17595 (9)	0.06675 (6)	0.01840 (17)
H11A	−0.0427	−0.1074	0.0555	0.022*
H11B	0.0532	−0.1751	0.0227	0.022*
O2	0.17229 (6)	−0.09424 (8)	0.48194 (4)	0.02185 (15)
O3	0.06394 (5)	−0.12510 (7)	0.36821 (5)	0.02150 (15)
C12	0.40341 (9)	0.18559 (11)	0.42461 (7)	0.0259 (2)
H12A	0.3526	0.1706	0.4586	0.031*
C13	0.47129 (9)	0.28931 (11)	0.44020 (8)	0.0308 (2)
H13A	0.4669	0.3443	0.4850	0.037*
C14	0.54514 (9)	0.31271 (12)	0.39082 (9)	0.0347 (3)
H14A	0.5915	0.3836	0.4016	0.042*
C15	0.55121 (10)	0.23302 (15)	0.32602 (10)	0.0405 (3)
H15A	0.6015	0.2494	0.2918	0.049*
C16	0.48372 (9)	0.12813 (13)	0.31033 (8)	0.0332 (3)
H16A	0.4888	0.0732	0.2656	0.040*
C17	0.40923 (7)	0.10336 (10)	0.35948 (6)	0.02131 (18)
C18	0.34031 (8)	−0.01409 (10)	0.34599 (7)	0.02296 (19)
H18A	0.3426	−0.0488	0.2913	0.028*
H18B	0.2683	0.0115	0.3497	0.028*
C19	0.37437 (7)	−0.12055 (10)	0.40862 (7)	0.02103 (18)
H19A	0.4493	−0.1358	0.4107	0.025*
H19B	0.3623	−0.0897	0.4623	0.025*
C20	0.31783 (7)	−0.24719 (9)	0.39020 (6)	0.01833 (17)
C21	0.37025 (8)	−0.35504 (11)	0.36547 (7)	0.0240 (2)
H21A	0.4418	−0.3476	0.3622	0.029*
C22	0.32102 (9)	−0.47260 (10)	0.34553 (7)	0.0254 (2)
H22A	0.3588	−0.5441	0.3291	0.031*
C23	0.21641 (8)	−0.48510 (10)	0.34974 (6)	0.02224 (19)
H23A	0.1825	−0.5658	0.3377	0.027*
C24	0.16174 (8)	−0.37824 (9)	0.37178 (6)	0.01810 (17)
H24A	0.0897	−0.3858	0.3730	0.022*
C25	0.21110 (7)	−0.26014 (9)	0.39210 (5)	0.01569 (16)
C26	0.14577 (7)	−0.15046 (9)	0.41621 (6)	0.01634 (16)
H1O1	0.0426 (13)	−0.1412 (16)	0.2549 (11)	0.040 (4)*
H1N1	−0.0007 (12)	−0.4910 (15)	0.0969 (10)	0.032 (4)*
H2N1	0.0777 (12)	−0.4202 (16)	0.0507 (10)	0.033 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.04360 (17)	0.02108 (12)	0.04013 (17)	−0.00762 (10)	0.01656 (13)	−0.00582 (10)
O1	0.0165 (3)	0.0312 (4)	0.0156 (3)	−0.0001 (3)	0.0057 (3)	−0.0022 (3)
N1	0.0182 (3)	0.0205 (4)	0.0155 (4)	−0.0027 (3)	0.0033 (3)	0.0009 (3)
C1	0.0230 (4)	0.0201 (4)	0.0178 (4)	0.0008 (3)	0.0066 (3)	−0.0022 (3)
C2	0.0258 (4)	0.0206 (4)	0.0214 (5)	−0.0005 (3)	0.0089 (4)	−0.0008 (3)
C3	0.0239 (4)	0.0183 (4)	0.0246 (5)	0.0001 (3)	0.0050 (4)	−0.0016 (3)
C4	0.0281 (5)	0.0227 (4)	0.0255 (5)	0.0008 (4)	0.0085 (4)	−0.0078 (4)
C5	0.0211 (4)	0.0248 (4)	0.0206 (5)	0.0004 (3)	0.0079 (4)	−0.0059 (4)
C6	0.0155 (4)	0.0201 (4)	0.0151 (4)	0.0015 (3)	0.0022 (3)	−0.0012 (3)
C7	0.0153 (4)	0.0209 (4)	0.0136 (4)	0.0004 (3)	0.0035 (3)	−0.0013 (3)
C8	0.0149 (3)	0.0208 (4)	0.0149 (4)	−0.0007 (3)	0.0026 (3)	0.0006 (3)
C9	0.0188 (4)	0.0227 (4)	0.0148 (4)	−0.0016 (3)	0.0018 (3)	0.0030 (3)
C10	0.0168 (4)	0.0243 (4)	0.0186 (4)	−0.0008 (3)	0.0006 (3)	−0.0005 (3)
C11	0.0183 (4)	0.0208 (4)	0.0157 (4)	0.0011 (3)	0.0010 (3)	−0.0006 (3)
O2	0.0217 (3)	0.0268 (3)	0.0178 (3)	−0.0008 (3)	0.0056 (3)	−0.0061 (3)
O3	0.0197 (3)	0.0251 (3)	0.0195 (3)	0.0051 (3)	0.0021 (3)	−0.0039 (3)
C12	0.0264 (5)	0.0253 (5)	0.0263 (5)	−0.0002 (4)	0.0050 (4)	0.0022 (4)
C13	0.0326 (5)	0.0245 (5)	0.0331 (6)	−0.0002 (4)	−0.0027 (5)	0.0002 (4)
C14	0.0249 (5)	0.0297 (5)	0.0469 (8)	−0.0076 (4)	−0.0040 (5)	0.0058 (5)
C15	0.0284 (5)	0.0478 (7)	0.0478 (8)	−0.0146 (5)	0.0141 (5)	0.0033 (6)
C16	0.0292 (5)	0.0400 (6)	0.0333 (6)	−0.0091 (5)	0.0148 (5)	−0.0026 (5)
C17	0.0174 (4)	0.0240 (4)	0.0225 (5)	−0.0015 (3)	0.0029 (3)	0.0044 (4)
C18	0.0214 (4)	0.0247 (4)	0.0227 (5)	−0.0035 (3)	0.0029 (4)	0.0030 (4)
C19	0.0163 (4)	0.0233 (4)	0.0234 (5)	−0.0012 (3)	0.0025 (3)	0.0023 (4)
C20	0.0163 (4)	0.0209 (4)	0.0178 (4)	0.0021 (3)	0.0026 (3)	0.0017 (3)
C21	0.0191 (4)	0.0285 (5)	0.0245 (5)	0.0070 (4)	0.0040 (4)	−0.0010 (4)
C22	0.0286 (5)	0.0239 (5)	0.0234 (5)	0.0095 (4)	0.0025 (4)	−0.0021 (4)
C23	0.0303 (5)	0.0182 (4)	0.0179 (4)	0.0023 (4)	0.0023 (4)	−0.0008 (3)
C24	0.0210 (4)	0.0191 (4)	0.0144 (4)	−0.0008 (3)	0.0034 (3)	0.0003 (3)
C25	0.0172 (4)	0.0177 (4)	0.0125 (4)	0.0011 (3)	0.0030 (3)	0.0008 (3)
C26	0.0165 (4)	0.0175 (4)	0.0162 (4)	−0.0008 (3)	0.0064 (3)	0.0003 (3)

Cl1—C3	1.7447 (10)	O3—C26	1.2728 (12)
O1—C7	1.4265 (11)	C12—C13	1.3905 (16)
O1—H1O1	0.890 (18)	C12—C17	1.3943 (16)
N1—C9	1.4934 (13)	C12—H12A	0.9500
N1—C10	1.4938 (13)	C13—C14	1.3829 (19)
N1—H1N1	0.954 (16)	C13—H13A	0.9500
N1—H2N1	0.917 (16)	C14—C15	1.375 (2)
C1—C2	1.3908 (14)	C14—H14A	0.9500
C1—C6	1.4008 (13)	C15—C16	1.3967 (18)
C1—H1A	0.9500	C15—H15A	0.9500
C2—C3	1.3881 (14)	C16—C17	1.3893 (15)
C2—H2A	0.9500	C16—H16A	0.9500
C3—C4	1.3852 (15)	C17—C18	1.5068 (14)
C4—C5	1.3928 (15)	C18—C19	1.5406 (15)
C4—H4A	0.9500	C18—H18A	0.9900
C5—C6	1.3929 (13)	C18—H18B	0.9900
C5—H5A	0.9500	C19—C20	1.5097 (14)
C6—C7	1.5284 (13)	C19—H19A	0.9900
C7—C11	1.5390 (13)	C19—H19B	0.9900
C7—C8	1.5404 (13)	C20—C21	1.3996 (13)
C8—C9	1.5196 (13)	C20—C25	1.4096 (12)
C8—H8A	0.9900	C21—C22	1.3898 (16)
C8—H8B	0.9900	C21—H21A	0.9500
C9—H9A	0.9900	C22—C23	1.3885 (16)
C9—H9B	0.9900	C22—H22A	0.9500
C10—C11	1.5237 (14)	C23—C24	1.3916 (13)
C10—H10A	0.9900	C23—H23A	0.9500
C10—H10B	0.9900	C24—C25	1.3966 (13)
C11—H11A	0.9900	C24—H24A	0.9500
C11—H11B	0.9900	C25—C26	1.5071 (12)
O2—C26	1.2513 (12)
C7—O1—H1O1	111.7 (11)	C7—C11—H11B	109.3
C9—N1—C10	112.91 (8)	H11A—C11—H11B	108.0
C9—N1—H1N1	106.3 (10)	C13—C12—C17	120.59 (10)
C10—N1—H1N1	107.7 (9)	C13—C12—H12A	119.7
C9—N1—H2N1	107.0 (10)	C17—C12—H12A	119.7
C10—N1—H2N1	110.6 (10)	C14—C13—C12	120.29 (12)
H1N1—N1—H2N1	112.3 (14)	C14—C13—H13A	119.9
C2—C1—C6	121.27 (9)	C12—C13—H13A	119.9
C2—C1—H1A	119.4	C15—C14—C13	119.73 (11)
C6—C1—H1A	119.4	C15—C14—H14A	120.1
C3—C2—C1	119.24 (9)	C13—C14—H14A	120.1
C3—C2—H2A	120.4	C14—C15—C16	120.27 (12)
C1—C2—H2A	120.4	C14—C15—H15A	119.9
C4—C3—C2	120.83 (9)	C16—C15—H15A	119.9
C4—C3—Cl1	119.64 (8)	C17—C16—C15	120.62 (12)
C2—C3—Cl1	119.53 (8)	C17—C16—H16A	119.7
C3—C4—C5	119.20 (9)	C15—C16—H16A	119.7
C3—C4—H4A	120.4	C16—C17—C12	118.49 (10)
C5—C4—H4A	120.4	C16—C17—C18	120.98 (10)
C4—C5—C6	121.48 (9)	C12—C17—C18	120.43 (9)
C4—C5—H5A	119.3	C17—C18—C19	111.07 (9)
C6—C5—H5A	119.3	C17—C18—H18A	109.4
C5—C6—C1	117.96 (9)	C19—C18—H18A	109.4
C5—C6—C7	121.28 (8)	C17—C18—H18B	109.4
C1—C6—C7	120.75 (8)	C19—C18—H18B	109.4
O1—C7—C6	111.95 (7)	H18A—C18—H18B	108.0
O1—C7—C11	104.79 (7)	C20—C19—C18	112.89 (8)
C6—C7—C11	110.66 (8)	C20—C19—H19A	109.0
O1—C7—C8	110.69 (7)	C18—C19—H19A	109.0
C6—C7—C8	109.57 (7)	C20—C19—H19B	109.0
C11—C7—C8	109.07 (7)	C18—C19—H19B	109.0
C9—C8—C7	111.65 (7)	H19A—C19—H19B	107.8
C9—C8—H8A	109.3	C21—C20—C25	117.53 (9)
C7—C8—H8A	109.3	C21—C20—C19	119.93 (8)
C9—C8—H8B	109.3	C25—C20—C19	122.43 (8)
C7—C8—H8B	109.3	C22—C21—C20	122.15 (9)
H8A—C8—H8B	108.0	C22—C21—H21A	118.9
N1—C9—C8	111.00 (8)	C20—C21—H21A	118.9
N1—C9—H9A	109.4	C23—C22—C21	119.73 (9)
C8—C9—H9A	109.4	C23—C22—H22A	120.1
N1—C9—H9B	109.4	C21—C22—H22A	120.1
C8—C9—H9B	109.4	C22—C23—C24	119.32 (9)
H9A—C9—H9B	108.0	C22—C23—H23A	120.3
N1—C10—C11	110.70 (7)	C24—C23—H23A	120.3
N1—C10—H10A	109.5	C23—C24—C25	121.03 (9)
C11—C10—H10A	109.5	C23—C24—H24A	119.5
N1—C10—H10B	109.5	C25—C24—H24A	119.5
C11—C10—H10B	109.5	C24—C25—C20	120.20 (8)
H10A—C10—H10B	108.1	C24—C25—C26	117.20 (8)
C10—C11—C7	111.40 (8)	C20—C25—C26	122.60 (8)
C10—C11—H11A	109.3	O2—C26—O3	124.51 (9)
C7—C11—H11A	109.3	O2—C26—C25	119.16 (8)
C10—C11—H11B	109.3	O3—C26—C25	116.28 (8)
C6—C1—C2—C3	0.23 (16)	C12—C13—C14—C15	0.08 (19)
C1—C2—C3—C4	−0.97 (16)	C13—C14—C15—C16	−0.5 (2)
C1—C2—C3—Cl1	178.92 (8)	C14—C15—C16—C17	0.5 (2)
C2—C3—C4—C5	0.93 (17)	C15—C16—C17—C12	0.07 (19)
Cl1—C3—C4—C5	−178.95 (9)	C15—C16—C17—C18	−176.32 (12)
C3—C4—C5—C6	−0.16 (17)	C13—C12—C17—C16	−0.52 (17)
C4—C5—C6—C1	−0.55 (15)	C13—C12—C17—C18	175.89 (10)
C4—C5—C6—C7	178.51 (10)	C16—C17—C18—C19	103.89 (12)
C2—C1—C6—C5	0.52 (15)	C12—C17—C18—C19	−72.43 (12)
C2—C1—C6—C7	−178.55 (9)	C17—C18—C19—C20	−171.43 (8)
C5—C6—C7—O1	6.88 (12)	C18—C19—C20—C21	110.08 (11)
C1—C6—C7—O1	−174.08 (8)	C18—C19—C20—C25	−65.94 (12)
C5—C6—C7—C11	123.37 (10)	C25—C20—C21—C22	−1.84 (16)
C1—C6—C7—C11	−57.59 (11)	C19—C20—C21—C22	−178.06 (10)
C5—C6—C7—C8	−116.32 (10)	C20—C21—C22—C23	0.16 (17)
C1—C6—C7—C8	62.72 (11)	C21—C22—C23—C24	1.79 (16)
O1—C7—C8—C9	59.36 (10)	C22—C23—C24—C25	−2.03 (15)
C6—C7—C8—C9	−176.70 (8)	C23—C24—C25—C20	0.30 (14)
C11—C7—C8—C9	−55.42 (10)	C23—C24—C25—C26	−179.23 (9)
C10—N1—C9—C8	−55.59 (10)	C21—C20—C25—C24	1.59 (14)
C7—C8—C9—N1	55.39 (10)	C19—C20—C25—C24	177.71 (9)
C9—N1—C10—C11	55.93 (10)	C21—C20—C25—C26	−178.90 (9)
N1—C10—C11—C7	−56.19 (10)	C19—C20—C25—C26	−2.79 (14)
O1—C7—C11—C10	−62.75 (9)	C24—C25—C26—O2	125.98 (10)
C6—C7—C11—C10	176.40 (7)	C20—C25—C26—O2	−53.54 (13)
C8—C7—C11—C10	55.79 (10)	C24—C25—C26—O3	−51.43 (12)
C17—C12—C13—C14	0.45 (17)	C20—C25—C26—O3	129.05 (10)

Cg2 is the centroid of the C20–C25 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O3	0.890 (18)	1.891 (18)	2.7401 (12)	158.8 (16)
N1—H1N1···O3i	0.954 (16)	1.754 (16)	2.6939 (11)	167.7 (15)
N1—H2N1···O2ii	0.917 (16)	1.818 (16)	2.7223 (11)	168.6 (15)
C8—H8B···Cg2	0.99	2.85	3.6743 (11)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C20–C25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O3	0.890 (18)	1.891 (18)	2.7401 (12)	158.8 (16)
N1—H1N1⋯O3i	0.954 (16)	1.754 (16)	2.6939 (11)	167.7 (15)
N1—H2N1⋯O2ii	0.917 (16)	1.818 (16)	2.7223 (11)	168.6 (15)
C8—H8B⋯Cg2	0.99	2.85	3.6743 (11)	141

Symmetry codes: (i) ; (ii) .