Literature DB >> 21754814

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

Jerry P Jasinski, James A Golen, B P Siddaraju, A S Dayananda, H S Yathirajan.

Abstract

In the title salt, C(11)H(15)ClNO(+)·C(7)H(5)O(2) (-), the dihedral angle between the mean planes of the chloro-phenyl 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 inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, and weak inter-molecular C-H⋯O, C-H⋯Cl and C-H⋯π inter-actions.

Entities: Chemical Disease Gene Species

Year: 2011 PMID： 21754814 PMCID： PMC3120431 DOI： 10.1107/S1600536811017855

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 333.80 Triclinic, 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 ▶) 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[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.125 S = 1.05 4184 reflections 217 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.29 e Å−3 Δρmin = −0.34 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017855/pv2415sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017855/pv2415Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811017855/pv2415Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4184 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3222 reflections with I > 2σ(I)
graphite	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 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

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.

	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*

	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)

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)

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

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) ; (ii) ; (iii) ; (iv) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 4-[(E)-(2,4-Difluoro-phen-yl)(hydroxy-imino)meth-yl]piperidinium picrate.

Authors: Jerry P Jasinski; Ray J Butcher; H S Yathirajan; L Mallesha; K N Mohana
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-05

2 in total