4-(4-Chloro­phen­yl)-4-hy­droxy­piperidinium benzoate

Jasinski, J.P.; Golen, J.A.; Siddaraju, B.P.; Dayananda, A.S.; Yathirajan, H.S.

doi:10.1107/S1600536811017855

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1436

doi:10.1107/S1600536811017855

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4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate

Jerry P. Jasinski,^a ^* James A. Golen,^a B. P. Siddaraju,^b A. S. Dayananda ^b and H. S. Yathirajan ^b

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 5 May 2011; accepted 11 May 2011; online 20 May 2011)

In the title salt, C₁₁H₁₅ClNO⁺·C₇H₅O₂⁻, the dihedral angle between the mean planes of the chlorophenyl ring of the cation and the benzene ring of the anion is 74.4 (1)°. In the cation, the six-membered piperazine ring adopts a chair conformation. The crystal packing is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, and weak intermolecular C—H⋯O, C—H⋯Cl and C—H⋯π interactions.

Related literature

For the synthesis and biological activity of uncondensed cyclic derivatives of piperidine, see: Vartanyan (1984 ). For puckering parameters, see: Cremer & Pople (1975 ) For related structures, see: Jasinski et al. (2009 ). For ring-motif pattterns, see: Bernstein et al. (1994 ).

Experimental

Crystal data

C₁₁H₁₅ClNO⁺·C₇H₅O₂⁻
M_r = 333.80
Triclinic, $[P \overline 1]$
a = 9.6235 (12) Å
b = 10.0971 (16) Å
c = 10.2251 (14) Å
α = 99.608 (12)°
β = 108.748 (13)°
γ = 113.357 (14)°
V = 812.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.34 × 0.30 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.920, T_max = 0.968
7857 measured reflections
4184 independent reflections
3222 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.125
S = 1.05
4184 reflections
217 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O3ⁱ	0.87 (1)	1.84 (1)	2.6964 (17)	166 (2)
O1—H1O⋯O3	0.82 (2)	2.05 (2)	2.7780 (16)	147 (2)
N1—H1NB⋯O2ⁱⁱ	0.86 (1)	1.92 (1)	2.7609 (18)	166 (2)
C16—H16A⋯Cl1ⁱⁱⁱ	0.95	2.78	3.5268 (17)	136
C9—H9B⋯O1ⁱ	0.99	2.46	3.3008 (19)	143
C1—H1A⋯Cg3^iv	0.95	2.70	3.554 (2)	150
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y-1, z; (iii) -x, -y+1, -z; (iv) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017855/pv2415sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017855/pv2415Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017855/pv2415Isup3.cml

checkCIF report

Comment top

4-(4-Chlorophenyl)-4-hydroxypiperidine is used as an intermediate for the synthesis of pharmaceuticals such as haloperidol (a neuroleptic drug used to treat patients with psychotic illnesses, extreme agitation, or Tourette's syndrome) and loperamide (a synthetic piperidine derivative, effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease). A review on the synthesis and biological activities of uncondensed cyclic derivatives of piperidine is reported (Vartanyan, 1984). The crystal structure of a related compound, 4-[(E)-(2,4-difluorophenyl) (hydroxyimino)methyl]piperidinium picrate (Jasinski et al., 2009) has been reported. In this paperwe report the crystal structure of C₁₁H₁₅ONCl⁺ . C₁₅H₁₂O₂^-.

In the title salt (Fig. 1), the 6-membered piperazine ring in the cation adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q, θ and ϕ, 0.568 (2) Å, 0.00 (19)° and 278 (9)°, respectively . The dihedral angle between the mean planes of the chlorophenyl ring of the cation and the benzene ring of the anion is 74.4 (1)°. The crystal structure is stabilized by N1—H1NA···O3 and N1—H1NB···O2, hydrogen bonds forming R₄⁴(12) ring-motif patttern (Bernstein et al., 1994) and N1—H1NA···O3, O1—H10···O3 hydrogen bonds resulting in R₂⁴(16) ring-motif, generating one dimensional chains along the c axis (Fig. 2). The structure is further consolidated by weak C9—H9B···O1, C16—H16A···Cl1 and C1—H1A···Cg3 π-ring intermolecular interactions.

Related literature top

For the synthesis and biological activity of uncondensed cyclic derivatives of piperidine, see: Vartanyan (1984). For puckering parameters, see: Cremer & Pople (1975) For related structures, see: Jasinski et al. (2009). For ring-motif pattterns, see: Bernstein et al. (1994).

Experimental top

Solutions of 4-(4-chlorophenyl)-piperidin-4-ol (2.12 g, 0.01 mol) in methanol (10 ml) and benzoic acid (1.226 g, 0.01 mol) in methanol (10 ml) were mixed and stirred in a beaker at 333 K for 30 minutes. The mixture was kept aside for three days at room temperature. The salt thus obtained was filtered and dried in a vaccum desiccator over phosphorous pentoxide. The compound was recrystallized from N,N-dimethylformamide by slow evaporation (m.p: 498 - 501 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram for the title compound viewed down the a axis. Dashed lines indicate N—H···O and O—H···O hydrogen bonds generating one dimensional chains along the c axis.

4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate top

Crystal data top

C₁₁H₁₅ClNO⁺·C₇H₅O₂⁻	Z = 2
M_r = 333.80	F(000) = 352
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6235 (12) Å	Cell parameters from 3721 reflections
b = 10.0971 (16) Å	θ = 3.7–32.3°
c = 10.2251 (14) Å	µ = 0.25 mm⁻¹
α = 99.608 (12)°	T = 173 K
β = 108.748 (13)°	Block, colorless
γ = 113.357 (14)°	0.34 × 0.30 × 0.13 mm
V = 812.7 (2) Å³

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4184 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3222 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.7°, θ_min = 3.7°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.920, T_max = 0.968	l = −13→13
7857 measured reflections

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0558P)² + 0.1776P] where P = (F_o² + 2F_c²)/3
4184 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₁H₁₅ClNO⁺·C₇H₅O₂⁻	γ = 113.357 (14)°
M_r = 333.80	V = 812.7 (2) Å³
Triclinic, P1	Z = 2
a = 9.6235 (12) Å	Mo Kα radiation
b = 10.0971 (16) Å	µ = 0.25 mm⁻¹
c = 10.2251 (14) Å	T = 173 K
α = 99.608 (12)°	0.34 × 0.30 × 0.13 mm
β = 108.748 (13)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4184 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	3222 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.968	R_int = 0.018
7857 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.29 e Å⁻³
4184 reflections	Δρ_min = −0.34 e Å⁻³
217 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.01350 (8)	0.19249 (7)	0.06335 (5)	0.06605 (19)
O1	0.37436 (18)	0.44147 (14)	0.79300 (12)	0.0470 (3)
H1O	0.360 (3)	0.498 (2)	0.746 (2)	0.056*
O2	0.46446 (18)	0.94763 (13)	0.77613 (13)	0.0553 (4)
O3	0.36182 (17)	0.70222 (13)	0.75160 (12)	0.0504 (3)
N1	0.51659 (18)	0.21683 (15)	0.95370 (13)	0.0372 (3)
H1NB	0.514 (2)	0.1342 (16)	0.9106 (18)	0.045*
H1NA	0.561 (2)	0.231 (2)	1.0473 (12)	0.045*
C1	0.1141 (2)	0.24120 (18)	0.48209 (16)	0.0351 (3)
H1A	0.0551	0.2344	0.5416	0.042*
C2	0.0314 (2)	0.21412 (19)	0.33410 (17)	0.0393 (4)
H2A	−0.0832	0.1888	0.2920	0.047*
C3	0.1181 (2)	0.22451 (18)	0.24891 (16)	0.0387 (4)
C4	0.2839 (2)	0.2611 (2)	0.30731 (18)	0.0474 (4)
H4A	0.3419	0.2678	0.2470	0.057*
C5	0.3653 (2)	0.2881 (2)	0.45636 (17)	0.0404 (4)
H5A	0.4802	0.3140	0.4978	0.048*
C6	0.28210 (18)	0.27817 (15)	0.54568 (14)	0.0278 (3)
C7	0.36689 (18)	0.30769 (15)	0.70961 (14)	0.0282 (3)
C8	0.54504 (19)	0.32943 (17)	0.76015 (15)	0.0331 (3)
H8A	0.5421	0.2395	0.7006	0.040*
H8B	0.6156	0.4212	0.7432	0.040*
C9	0.6232 (2)	0.34823 (18)	0.92121 (16)	0.0373 (3)
H9A	0.7351	0.3556	0.9474	0.045*
H9B	0.6383	0.4445	0.9818	0.045*
C10	0.3447 (2)	0.19647 (19)	0.91069 (16)	0.0388 (4)
H10A	0.3496	0.2880	0.9697	0.047*
H10B	0.2763	0.1064	0.9310	0.047*
C11	0.26339 (19)	0.17363 (18)	0.74911 (16)	0.0346 (3)
H11A	0.1503	0.1632	0.7235	0.042*
H11B	0.2503	0.0774	0.6904	0.042*
C12	0.37590 (19)	0.80987 (17)	0.70139 (15)	0.0324 (3)
C13	0.27602 (18)	0.76646 (16)	0.53903 (15)	0.0283 (3)
C14	0.1622 (2)	0.61404 (17)	0.45411 (16)	0.0363 (3)
H14A	0.1524	0.5367	0.4977	0.044*
C15	0.0633 (2)	0.5739 (2)	0.30681 (18)	0.0447 (4)
H15A	−0.0151	0.4695	0.2498	0.054*
C16	0.0782 (2)	0.6857 (2)	0.24240 (18)	0.0463 (4)
H16A	0.0093	0.6580	0.1413	0.056*
C17	0.1924 (2)	0.8366 (2)	0.32407 (19)	0.0452 (4)
H17A	0.2042	0.9130	0.2790	0.054*
C18	0.2902 (2)	0.87754 (17)	0.47237 (17)	0.0360 (3)
H18A	0.3677	0.9823	0.5289	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0874 (4)	0.0854 (4)	0.0294 (2)	0.0485 (3)	0.0179 (2)	0.0257 (2)
O1	0.0826 (9)	0.0447 (7)	0.0316 (6)	0.0468 (7)	0.0235 (6)	0.0149 (5)
O2	0.0710 (9)	0.0364 (6)	0.0391 (6)	0.0248 (6)	0.0082 (6)	0.0014 (5)
O3	0.0727 (9)	0.0397 (6)	0.0299 (5)	0.0272 (6)	0.0101 (6)	0.0147 (5)
N1	0.0512 (8)	0.0349 (7)	0.0253 (6)	0.0256 (6)	0.0101 (6)	0.0098 (5)
C1	0.0360 (8)	0.0427 (8)	0.0311 (7)	0.0198 (7)	0.0169 (6)	0.0158 (6)
C2	0.0362 (8)	0.0442 (9)	0.0344 (7)	0.0189 (7)	0.0109 (7)	0.0159 (7)
C3	0.0526 (10)	0.0401 (8)	0.0270 (7)	0.0256 (8)	0.0151 (7)	0.0155 (6)
C4	0.0594 (11)	0.0691 (12)	0.0375 (8)	0.0397 (10)	0.0314 (8)	0.0291 (8)
C5	0.0406 (9)	0.0589 (10)	0.0371 (8)	0.0300 (8)	0.0225 (7)	0.0243 (7)
C6	0.0346 (8)	0.0273 (6)	0.0269 (6)	0.0175 (6)	0.0146 (6)	0.0119 (5)
C7	0.0360 (8)	0.0289 (7)	0.0260 (6)	0.0192 (6)	0.0153 (6)	0.0109 (5)
C8	0.0326 (8)	0.0347 (7)	0.0294 (7)	0.0152 (6)	0.0119 (6)	0.0102 (6)
C9	0.0364 (8)	0.0387 (8)	0.0287 (7)	0.0172 (7)	0.0075 (6)	0.0080 (6)
C10	0.0466 (9)	0.0422 (8)	0.0329 (7)	0.0217 (7)	0.0192 (7)	0.0192 (6)
C11	0.0342 (8)	0.0379 (8)	0.0320 (7)	0.0159 (7)	0.0142 (6)	0.0164 (6)
C12	0.0366 (8)	0.0331 (7)	0.0290 (7)	0.0210 (6)	0.0116 (6)	0.0083 (6)
C13	0.0298 (7)	0.0322 (7)	0.0300 (7)	0.0187 (6)	0.0150 (6)	0.0129 (5)
C14	0.0387 (8)	0.0330 (7)	0.0326 (7)	0.0155 (7)	0.0110 (6)	0.0139 (6)
C15	0.0445 (10)	0.0408 (9)	0.0335 (8)	0.0149 (8)	0.0079 (7)	0.0089 (7)
C16	0.0498 (10)	0.0602 (11)	0.0316 (8)	0.0290 (9)	0.0141 (7)	0.0216 (8)
C17	0.0557 (11)	0.0527 (10)	0.0442 (9)	0.0311 (9)	0.0271 (8)	0.0316 (8)
C18	0.0406 (9)	0.0327 (7)	0.0407 (8)	0.0191 (7)	0.0205 (7)	0.0166 (6)

Geometric parameters (Å, º) top

Cl1—C3	1.7400 (15)	C8—C9	1.5167 (19)
O1—C7	1.4338 (17)	C8—H8A	0.9900
O1—H1O	0.823 (15)	C8—H8B	0.9900
O2—C12	1.2376 (19)	C9—H9A	0.9900
O3—C12	1.2560 (18)	C9—H9B	0.9900
N1—C10	1.485 (2)	C10—C11	1.514 (2)
N1—C9	1.487 (2)	C10—H10A	0.9900
N1—H1NB	0.861 (10)	C10—H10B	0.9900
N1—H1NA	0.873 (10)	C11—H11A	0.9900
C1—C2	1.383 (2)	C11—H11B	0.9900
C1—C6	1.393 (2)	C12—C13	1.5064 (19)
C1—H1A	0.9500	C13—C14	1.389 (2)
C2—C3	1.376 (2)	C13—C18	1.391 (2)
C2—H2A	0.9500	C14—C15	1.381 (2)
C3—C4	1.373 (3)	C14—H14A	0.9500
C4—C5	1.391 (2)	C15—C16	1.381 (2)
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.387 (2)	C16—C17	1.373 (3)
C5—H5A	0.9500	C16—H16A	0.9500
C6—C7	1.5250 (18)	C17—C18	1.386 (2)
C7—C8	1.533 (2)	C17—H17A	0.9500
C7—C11	1.536 (2)	C18—H18A	0.9500

C7—O1—H1O	114.0 (15)	N1—C9—H9A	109.4
C10—N1—C9	111.70 (12)	C8—C9—H9A	109.4
C10—N1—H1NB	110.7 (13)	N1—C9—H9B	109.4
C9—N1—H1NB	110.2 (13)	C8—C9—H9B	109.4
C10—N1—H1NA	108.5 (13)	H9A—C9—H9B	108.0
C9—N1—H1NA	110.3 (13)	N1—C10—C11	110.57 (13)
H1NB—N1—H1NA	105.3 (16)	N1—C10—H10A	109.5
C2—C1—C6	121.38 (14)	C11—C10—H10A	109.5
C2—C1—H1A	119.3	N1—C10—H10B	109.5
C6—C1—H1A	119.3	C11—C10—H10B	109.5
C3—C2—C1	118.85 (15)	H10A—C10—H10B	108.1
C3—C2—H2A	120.6	C10—C11—C7	112.01 (13)
C1—C2—H2A	120.6	C10—C11—H11A	109.2
C4—C3—C2	121.62 (14)	C7—C11—H11A	109.2
C4—C3—Cl1	119.92 (13)	C10—C11—H11B	109.2
C2—C3—Cl1	118.46 (13)	C7—C11—H11B	109.2
C3—C4—C5	118.82 (15)	H11A—C11—H11B	107.9
C3—C4—H4A	120.6	O2—C12—O3	124.52 (14)
C5—C4—H4A	120.6	O2—C12—C13	118.42 (13)
C6—C5—C4	121.26 (15)	O3—C12—C13	117.06 (13)
C6—C5—H5A	119.4	C14—C13—C18	118.72 (13)
C4—C5—H5A	119.4	C14—C13—C12	120.11 (13)
C5—C6—C1	118.06 (13)	C18—C13—C12	121.12 (13)
C5—C6—C7	122.92 (13)	C15—C14—C13	120.57 (14)
C1—C6—C7	119.01 (12)	C15—C14—H14A	119.7
O1—C7—C6	110.41 (11)	C13—C14—H14A	119.7
O1—C7—C8	108.40 (12)	C16—C15—C14	120.02 (16)
C6—C7—C8	112.93 (11)	C16—C15—H15A	120.0
O1—C7—C11	106.31 (12)	C14—C15—H15A	120.0
C6—C7—C11	110.12 (12)	C17—C16—C15	120.19 (15)
C8—C7—C11	108.43 (11)	C17—C16—H16A	119.9
C9—C8—C7	112.22 (12)	C15—C16—H16A	119.9
C9—C8—H8A	109.2	C16—C17—C18	119.94 (14)
C7—C8—H8A	109.2	C16—C17—H17A	120.0
C9—C8—H8B	109.2	C18—C17—H17A	120.0
C7—C8—H8B	109.2	C17—C18—C13	120.54 (15)
H8A—C8—H8B	107.9	C17—C18—H18A	119.7
N1—C9—C8	111.13 (12)	C13—C18—H18A	119.7

C6—C1—C2—C3	−0.1 (2)	C10—N1—C9—C8	−56.75 (16)
C1—C2—C3—C4	−0.1 (2)	C7—C8—C9—N1	55.69 (16)
C1—C2—C3—Cl1	−179.23 (12)	C9—N1—C10—C11	57.50 (16)
C2—C3—C4—C5	0.0 (3)	N1—C10—C11—C7	−57.35 (17)
Cl1—C3—C4—C5	179.15 (13)	O1—C7—C11—C10	−61.50 (15)
C3—C4—C5—C6	0.3 (3)	C6—C7—C11—C10	178.89 (12)
C4—C5—C6—C1	−0.5 (2)	C8—C7—C11—C10	54.87 (16)
C4—C5—C6—C7	−179.69 (14)	O2—C12—C13—C14	−173.36 (15)
C2—C1—C6—C5	0.4 (2)	O3—C12—C13—C14	6.1 (2)
C2—C1—C6—C7	179.65 (13)	O2—C12—C13—C18	3.9 (2)
C5—C6—C7—O1	114.43 (16)	O3—C12—C13—C18	−176.65 (15)
C1—C6—C7—O1	−64.80 (17)	C18—C13—C14—C15	−1.0 (2)
C5—C6—C7—C8	−7.11 (19)	C12—C13—C14—C15	176.34 (15)
C1—C6—C7—C8	173.66 (13)	C13—C14—C15—C16	0.7 (3)
C5—C6—C7—C11	−128.48 (15)	C14—C15—C16—C17	0.6 (3)
C1—C6—C7—C11	52.29 (16)	C15—C16—C17—C18	−1.5 (3)
O1—C7—C8—C9	61.09 (15)	C16—C17—C18—C13	1.1 (3)
C6—C7—C8—C9	−176.24 (11)	C14—C13—C18—C17	0.1 (2)
C11—C7—C8—C9	−53.92 (15)	C12—C13—C18—C17	−177.21 (14)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O3ⁱ	0.87 (1)	1.84 (1)	2.6964 (17)	166 (2)
O1—H1O···O3	0.82 (2)	2.05 (2)	2.7780 (16)	147 (2)
N1—H1NB···O2ⁱⁱ	0.86 (1)	1.92 (1)	2.7609 (18)	166 (2)
C16—H16A···Cl1ⁱⁱⁱ	0.95	2.78	3.5268 (17)	136
C9—H9B···O1ⁱ	0.99	2.46	3.3008 (19)	143
C1—H1A···Cg3^iv	0.95	2.70	3.554 (2)	150

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y−1, z; (iii) −x, −y+1, −z; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅ClNO⁺·C₇H₅O₂⁻
M_r	333.80
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.6235 (12), 10.0971 (16), 10.2251 (14)
α, β, γ (°)	99.608 (12), 108.748 (13), 113.357 (14)
V (Å³)	812.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.34 × 0.30 × 0.13

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.920, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	7857, 4184, 3222
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.05
No. of reflections	4184
No. of parameters	217
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O3ⁱ	0.873 (10)	1.842 (11)	2.6964 (17)	165.8 (17)
O1—H1O···O3	0.823 (15)	2.052 (17)	2.7780 (16)	146.9 (19)
N1—H1NB···O2ⁱⁱ	0.861 (10)	1.916 (11)	2.7609 (18)	166.3 (17)
C16—H16A···Cl1ⁱⁱⁱ	0.95	2.78	3.5268 (17)	136
C9—H9B···O1ⁱ	0.99	2.46	3.3008 (19)	143
C1—H1A···Cg3^iv	0.95	2.70	3.554 (2)	150

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y−1, z; (iii) −x, −y+1, −z; (iv) −x, −y+1, −z+1.

Acknowledgements

BPS thanks the University of Mysore for the research facilities. HSY is grateful to RL Fine Chem., Bengaluru, India, for a pure sample of 4-(4-chlorophynyl)-piperidin-4-ol. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, Vol. 2, edited by H.-B. Bürgi & J. D. Dunitz, pp. 431–507. New York: VCH. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mallesha, L. & Mohana, K. N. (2009). Acta Cryst. E65, o2365–o2366. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vartanyan, R. S. (1984). Pharm. Chem. J. 18, 736–749. CrossRef Google Scholar

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