4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium maleate maleic acid solvate.

In the cation of the title compound, C(11)H(15)ClNO(+)·C(4)H(3)O(4) (-)·C(4)H(4)O(4), the dihedral angle between the mean planes of the chlorine-substituted aromatic ring and the 4-hy-droxy-piperidinium ring (C-C-C-C-C-N) is 61.9 (8)°. Intra-molecular O-H⋯O and inter-molecular O-H⋯O and N-H⋯O hydrogen bonding, as well as weak π-stacking inter-actions [centroid-centroid distance = 3.646 (5) Å] help to establish the packing.

Related literature

For the synthesis and biological activity of uncondensed cyclic derivatives of piperidine, see: Vartanyan (1984 ▶). For related structures, see: James & Williams (1974 ▶); Bertolasi et al. (1980 ▶); Dawson et al. (1986 ▶); Vyas et al. (1999 ▶); Kiang et al. (2003 ▶); Trask et al. (2005 ▶); Mohamed et al. (2009 ▶); Dutkiewicz et al. (2010 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C11H15ClNO+·C4H3O4 −·C4H4O4

M = 443.83

Monoclinic,

a = 19.282 (7) Å

b = 7.867 (3) Å

c = 25.115 (9) Å

β = 91.545 (5)°

V = 3808 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.52 × 0.41 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.878, T max = 0.907

18187 measured reflections

5841 independent reflections

5194 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.03

5841 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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/S1600536810026917/wm2372sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026917/wm2372Isup2.hkl

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

C11H15ClNO+·C4H3O4−·C4H4O4	F(000) = 1856
Mr = 443.83	Dx = 1.548 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8484 reflections
a = 19.282 (7) Å	θ = 2.6–31.3°
b = 7.867 (3) Å	µ = 0.26 mm−1
c = 25.115 (9) Å	T = 100 K
β = 91.545 (5)°	Block, yellow
V = 3808 (2) Å3	0.52 × 0.41 × 0.39 mm
Z = 8

Bruker APEXII CCD diffractometer	5841 independent reflections
Radiation source: fine-focus sealed tube	5194 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 31.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −27→27
Tmin = 0.878, Tmax = 0.907	k = −11→11
18187 measured reflections	l = −35→35

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0463P)2 + 3.2429P] where P = (Fo2 + 2Fc2)/3
5841 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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. 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	Uiso*/Ueq
Cl1	0.480203 (14)	0.66435 (4)	0.161617 (11)	0.02088 (7)
O4B	0.16691 (4)	0.58804 (10)	0.50337 (3)	0.01619 (15)
O3B	0.22900 (4)	0.66101 (10)	0.42453 (3)	0.01604 (15)
C5B	0.20779 (5)	0.56565 (13)	0.38519 (4)	0.01359 (18)
C4B	0.14848 (6)	0.44620 (14)	0.39300 (4)	0.01543 (19)
H4B	0.1353	0.3844	0.3628	0.019*
C2B	0.11909 (5)	0.47937 (13)	0.49149 (4)	0.01414 (19)
C3B	0.11113 (6)	0.41304 (14)	0.43602 (4)	0.01520 (19)
H3B	0.0747	0.3371	0.4304	0.018*
O3A	0.46151 (4)	0.35880 (11)	0.96021 (3)	0.01793 (16)
C2A	0.44308 (6)	0.35385 (13)	1.00654 (4)	0.01452 (19)
C3A	0.38419 (6)	0.45056 (14)	1.02827 (4)	0.0163 (2)
H3A	0.3766	0.4349	1.0644	0.020*
C5A	0.33654 (6)	0.61984 (14)	0.94690 (4)	0.01610 (19)
C4A	0.34039 (6)	0.55740 (14)	1.00297 (4)	0.0162 (2)
H4A	0.3060	0.6007	1.0244	0.019*
O1A	0.47414 (4)	0.26101 (10)	1.04317 (3)	0.01712 (16)
O2A	0.29197 (4)	0.72438 (11)	0.93499 (3)	0.02023 (17)
O1B	0.07936 (4)	0.42630 (10)	0.52580 (3)	0.01788 (16)
O2B	0.23403 (4)	0.57247 (10)	0.34108 (3)	0.01693 (16)
C4C	0.37887 (5)	0.24201 (13)	0.25343 (4)	0.01180 (18)
C1C	0.44091 (5)	0.50191 (14)	0.19706 (4)	0.01430 (19)
C6C	0.39980 (5)	0.54258 (13)	0.23944 (4)	0.01428 (19)
H6C	0.3928	0.6554	0.2490	0.017*
C5C	0.36902 (5)	0.41155 (13)	0.26767 (4)	0.01336 (18)
H5C	0.3415	0.4374	0.2964	0.016*
C3C	0.42116 (5)	0.20613 (14)	0.21058 (4)	0.01490 (19)
H3C	0.4287	0.0936	0.2010	0.018*
C2C	0.45221 (6)	0.33510 (14)	0.18203 (4)	0.0161 (2)
H2C	0.4800	0.3100	0.1534	0.019*
O1C	0.33643 (4)	−0.04881 (10)	0.24944 (3)	0.01551 (15)
H1C	0.3122	−0.0211	0.2235	0.023*
C10C	0.39685 (5)	0.03445 (13)	0.32796 (4)	0.01363 (18)
H10A	0.4395	−0.0037	0.3123	0.016*
H10B	0.4080	0.1291	0.3514	0.016*
C8C	0.27733 (5)	0.14407 (13)	0.30800 (4)	0.01358 (18)
H8C1	0.2841	0.2427	0.3307	0.016*
H8C2	0.2444	0.1744	0.2797	0.016*
C7C	0.34665 (5)	0.09495 (13)	0.28369 (4)	0.01154 (17)
C9C	0.36671 (5)	−0.10930 (14)	0.36035 (4)	0.01464 (19)
H9C1	0.3594	−0.2083	0.3379	0.018*
H9C2	0.3989	−0.1401	0.3891	0.018*
C11C	0.24805 (5)	−0.00126 (14)	0.34043 (4)	0.01492 (19)
H11A	0.2054	0.0348	0.3566	0.018*
H11B	0.2374	−0.0968	0.3172	0.018*
N1C	0.29935 (5)	−0.05450 (12)	0.38279 (3)	0.01394 (17)
O4A	0.38012 (5)	0.56565 (12)	0.91126 (3)	0.02079 (17)
H13C	0.2810 (9)	−0.142 (2)	0.3999 (7)	0.026 (4)*
H14C	0.3072 (8)	0.031 (2)	0.4050 (7)	0.024 (4)*
H1A	0.4103 (10)	0.490 (3)	0.9264 (8)	0.042 (5)*
H2A	0.5113 (11)	0.206 (3)	1.0307 (8)	0.049 (6)*
H1B	0.1992 (12)	0.629 (3)	0.4638 (9)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01862 (13)	0.02183 (14)	0.02233 (13)	−0.00193 (9)	0.00295 (9)	0.01083 (10)
O4B	0.0190 (4)	0.0170 (4)	0.0125 (3)	−0.0050 (3)	−0.0001 (3)	−0.0003 (3)
O3B	0.0197 (4)	0.0149 (4)	0.0136 (3)	−0.0050 (3)	0.0016 (3)	−0.0013 (3)
C5B	0.0153 (4)	0.0120 (4)	0.0134 (4)	0.0008 (3)	−0.0006 (3)	0.0011 (3)
C4B	0.0185 (5)	0.0139 (5)	0.0138 (4)	−0.0022 (4)	−0.0015 (4)	−0.0018 (3)
C2B	0.0158 (5)	0.0126 (4)	0.0139 (4)	−0.0002 (4)	−0.0009 (3)	0.0011 (3)
C3B	0.0172 (5)	0.0140 (5)	0.0143 (4)	−0.0022 (4)	−0.0017 (4)	−0.0009 (3)
O3A	0.0202 (4)	0.0188 (4)	0.0150 (3)	0.0024 (3)	0.0031 (3)	0.0004 (3)
C2A	0.0154 (5)	0.0122 (4)	0.0160 (4)	−0.0015 (3)	0.0007 (3)	−0.0003 (3)
C3A	0.0191 (5)	0.0153 (5)	0.0146 (4)	0.0008 (4)	0.0027 (4)	0.0000 (4)
C5A	0.0168 (5)	0.0136 (5)	0.0178 (5)	−0.0020 (4)	−0.0011 (4)	0.0008 (4)
C4A	0.0171 (5)	0.0145 (5)	0.0170 (5)	0.0005 (4)	0.0022 (4)	−0.0005 (4)
O1A	0.0181 (4)	0.0173 (4)	0.0159 (3)	0.0041 (3)	0.0010 (3)	0.0013 (3)
O2A	0.0195 (4)	0.0164 (4)	0.0246 (4)	0.0012 (3)	−0.0029 (3)	0.0038 (3)
O1B	0.0198 (4)	0.0188 (4)	0.0151 (3)	−0.0042 (3)	0.0025 (3)	0.0011 (3)
O2B	0.0191 (4)	0.0187 (4)	0.0131 (3)	−0.0003 (3)	0.0019 (3)	0.0003 (3)
C4C	0.0123 (4)	0.0121 (4)	0.0110 (4)	−0.0001 (3)	−0.0002 (3)	0.0005 (3)
C1C	0.0122 (4)	0.0171 (5)	0.0136 (4)	−0.0018 (4)	−0.0003 (3)	0.0057 (4)
C6C	0.0151 (4)	0.0124 (4)	0.0154 (4)	−0.0006 (4)	0.0004 (3)	0.0013 (3)
C5C	0.0152 (4)	0.0129 (4)	0.0122 (4)	−0.0001 (3)	0.0023 (3)	−0.0003 (3)
C3C	0.0155 (5)	0.0144 (5)	0.0149 (4)	0.0006 (4)	0.0018 (3)	−0.0003 (4)
C2C	0.0158 (5)	0.0197 (5)	0.0128 (4)	0.0010 (4)	0.0035 (3)	0.0013 (4)
O1C	0.0234 (4)	0.0113 (3)	0.0117 (3)	−0.0010 (3)	−0.0014 (3)	−0.0015 (3)
C10C	0.0133 (4)	0.0147 (5)	0.0129 (4)	0.0004 (3)	0.0004 (3)	0.0017 (3)
C8C	0.0133 (4)	0.0128 (4)	0.0147 (4)	0.0006 (3)	0.0014 (3)	0.0030 (3)
C7C	0.0139 (4)	0.0100 (4)	0.0107 (4)	−0.0004 (3)	0.0006 (3)	−0.0003 (3)
C9C	0.0161 (5)	0.0143 (5)	0.0135 (4)	0.0015 (4)	0.0005 (3)	0.0019 (3)
C11C	0.0133 (4)	0.0160 (5)	0.0154 (4)	−0.0015 (4)	0.0002 (3)	0.0033 (4)
N1C	0.0172 (4)	0.0136 (4)	0.0110 (4)	−0.0017 (3)	0.0011 (3)	0.0011 (3)
O4A	0.0230 (4)	0.0236 (4)	0.0157 (4)	0.0043 (3)	0.0010 (3)	0.0026 (3)

Cl1—C1C	1.7424 (11)	C1C—C2C	1.3844 (16)
O4B—C2B	1.2865 (13)	C6C—C5C	1.3929 (14)
O4B—H1B	1.23 (2)	C6C—H6C	0.9300
O3B—C5B	1.2978 (13)	C5C—H5C	0.9300
O3B—H1B	1.18 (2)	C3C—C2C	1.3876 (15)
C5B—O2B	1.2315 (13)	C3C—H3C	0.9300
C5B—C4B	1.4972 (15)	C2C—H2C	0.9300
C4B—C3B	1.3403 (15)	O1C—C7C	1.4314 (12)
C4B—H4B	0.9300	O1C—H1C	0.8200
C2B—O1B	1.2408 (13)	C10C—C9C	1.5178 (15)
C2B—C3B	1.4917 (15)	C10C—C7C	1.5301 (15)
C3B—H3B	0.9300	C10C—H10A	0.9700
O3A—C2A	1.2265 (13)	C10C—H10B	0.9700
C2A—O1A	1.3072 (13)	C8C—C11C	1.5212 (15)
C2A—C3A	1.4830 (15)	C8C—C7C	1.5339 (15)
C3A—C4A	1.3396 (16)	C8C—H8C1	0.9700
C3A—H3A	0.9300	C8C—H8C2	0.9700
C5A—O2A	1.2209 (14)	C9C—N1C	1.4932 (14)
C5A—O4A	1.3153 (14)	C9C—H9C1	0.9700
C5A—C4A	1.4912 (16)	C9C—H9C2	0.9700
C4A—H4A	0.9300	C11C—N1C	1.4930 (14)
O1A—H2A	0.90 (2)	C11C—H11A	0.9700
C4C—C5C	1.3952 (15)	C11C—H11B	0.9700
C4C—C3C	1.3965 (14)	N1C—H13C	0.890 (17)
C4C—C7C	1.5255 (14)	N1C—H14C	0.887 (17)
C1C—C6C	1.3816 (15)	O4A—H1A	0.91 (2)
C2B—O4B—H1B	111.1 (10)	C1C—C2C—C3C	118.61 (10)
C5B—O3B—H1B	111.1 (11)	C1C—C2C—H2C	120.7
O2B—C5B—O3B	122.07 (10)	C3C—C2C—H2C	120.7
O2B—C5B—C4B	118.62 (9)	C7C—O1C—H1C	109.5
O3B—C5B—C4B	119.30 (9)	C9C—C10C—C7C	112.16 (9)
C3B—C4B—C5B	131.05 (10)	C9C—C10C—H10A	109.2
C3B—C4B—H4B	114.5	C7C—C10C—H10A	109.2
C5B—C4B—H4B	114.5	C9C—C10C—H10B	109.2
O1B—C2B—O4B	120.98 (10)	C7C—C10C—H10B	109.2
O1B—C2B—C3B	118.74 (10)	H10A—C10C—H10B	107.9
O4B—C2B—C3B	120.28 (9)	C11C—C8C—C7C	111.33 (9)
C4B—C3B—C2B	129.85 (10)	C11C—C8C—H8C1	109.4
C4B—C3B—H3B	115.1	C7C—C8C—H8C1	109.4
C2B—C3B—H3B	115.1	C11C—C8C—H8C2	109.4
O3A—C2A—O1A	123.13 (10)	C7C—C8C—H8C2	109.4
O3A—C2A—C3A	125.25 (10)	H8C1—C8C—H8C2	108.0
O1A—C2A—C3A	111.63 (9)	O1C—C7C—C4C	110.55 (8)
C4A—C3A—C2A	128.80 (10)	O1C—C7C—C10C	105.37 (8)
C4A—C3A—H3A	115.6	C4C—C7C—C10C	109.86 (8)
C2A—C3A—H3A	115.6	O1C—C7C—C8C	109.32 (8)
O2A—C5A—O4A	120.67 (10)	C4C—C7C—C8C	112.22 (8)
O2A—C5A—C4A	118.03 (10)	C10C—C7C—C8C	109.28 (8)
O4A—C5A—C4A	121.29 (10)	N1C—C9C—C10C	109.67 (9)
C3A—C4A—C5A	132.01 (10)	N1C—C9C—H9C1	109.7
C3A—C4A—H4A	114.0	C10C—C9C—H9C1	109.7
C5A—C4A—H4A	114.0	N1C—C9C—H9C2	109.7
C2A—O1A—H2A	112.2 (13)	C10C—C9C—H9C2	109.7
C5C—C4C—C3C	118.49 (9)	H9C1—C9C—H9C2	108.2
C5C—C4C—C7C	122.50 (9)	N1C—C11C—C8C	110.12 (9)
C3C—C4C—C7C	118.99 (9)	N1C—C11C—H11A	109.6
C6C—C1C—C2C	121.83 (9)	C8C—C11C—H11A	109.6
C6C—C1C—Cl1	119.35 (9)	N1C—C11C—H11B	109.6
C2C—C1C—Cl1	118.82 (8)	C8C—C11C—H11B	109.6
C1C—C6C—C5C	118.81 (10)	H11A—C11C—H11B	108.1
C1C—C6C—H6C	120.6	C11C—N1C—C9C	112.23 (8)
C5C—C6C—H6C	120.6	C11C—N1C—H13C	107.2 (11)
C6C—C5C—C4C	120.95 (9)	C9C—N1C—H13C	108.7 (11)
C6C—C5C—H5C	119.5	C11C—N1C—H14C	109.4 (11)
C4C—C5C—H5C	119.5	C9C—N1C—H14C	108.7 (10)
C2C—C3C—C4C	121.30 (10)	H13C—N1C—H14C	110.6 (15)
C2C—C3C—H3C	119.3	C5A—O4A—H1A	110.0 (12)
C4C—C3C—H3C	119.3
O2B—C5B—C4B—C3B	179.66 (11)	Cl1—C1C—C2C—C3C	179.61 (8)
O3B—C5B—C4B—C3B	−1.76 (18)	C4C—C3C—C2C—C1C	0.45 (16)
C5B—C4B—C3B—C2B	−3.5 (2)	C5C—C4C—C7C—O1C	152.93 (9)
O1B—C2B—C3B—C4B	−177.70 (11)	C3C—C4C—C7C—O1C	−28.58 (13)
O4B—C2B—C3B—C4B	1.50 (18)	C5C—C4C—C7C—C10C	−91.18 (12)
O3A—C2A—C3A—C4A	0.66 (19)	C3C—C4C—C7C—C10C	87.30 (11)
O1A—C2A—C3A—C4A	−179.62 (11)	C5C—C4C—C7C—C8C	30.61 (13)
C2A—C3A—C4A—C5A	−2.4 (2)	C3C—C4C—C7C—C8C	−150.91 (9)
O2A—C5A—C4A—C3A	−176.96 (12)	C9C—C10C—C7C—O1C	−62.30 (10)
O4A—C5A—C4A—C3A	2.41 (19)	C9C—C10C—C7C—C4C	178.59 (8)
C2C—C1C—C6C—C5C	0.00 (16)	C9C—C10C—C7C—C8C	55.07 (11)
Cl1—C1C—C6C—C5C	−179.61 (8)	C11C—C8C—C7C—O1C	60.01 (11)
C1C—C6C—C5C—C4C	−0.44 (16)	C11C—C8C—C7C—C4C	−176.97 (8)
C3C—C4C—C5C—C6C	0.87 (15)	C11C—C8C—C7C—C10C	−54.84 (11)
C7C—C4C—C5C—C6C	179.36 (9)	C7C—C10C—C9C—N1C	−56.43 (11)
C5C—C4C—C3C—C2C	−0.88 (16)	C7C—C8C—C11C—N1C	56.71 (11)
C7C—C4C—C3C—C2C	−179.42 (9)	C8C—C11C—N1C—C9C	−58.48 (11)
C6C—C1C—C2C—C3C	0.00 (16)	C10C—C9C—N1C—C11C	57.97 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1C—H1C···O2Bi	0.82	1.97	2.7852 (13)	171
O1A—H2A···O1Bii	0.90 (2)	1.68 (2)	2.5546 (13)	162 (2)
N1C—H13C···O3Biii	0.890 (17)	1.954 (18)	2.8328 (14)	168.6 (16)
N1C—H14C···O2Aiv	0.887 (17)	2.087 (17)	2.9144 (15)	154.9 (15)
O4A—H1A···O3A	0.91 (2)	1.65 (2)	2.5531 (13)	173.7 (19)
O3B—H1B···O4B	1.18 (2)	1.23 (2)	2.4108 (12)	177 (2)

CgX···CgY	Cg···Cg	CgX···Perp	CgY···Perp
Cg2···Cg2i	3.646 (5)	-3.460 (6)	-3.460 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1C—H1C⋯O2Bi	0.82	1.97	2.7852 (13)	171
O1A—H2A⋯O1Bii	0.90 (2)	1.68 (2)	2.5546 (13)	162 (2)
N1C—H13C⋯O3Biii	0.890 (17)	1.954 (18)	2.8328 (14)	168.6 (16)
N1C—H14C⋯O2Aiv	0.887 (17)	2.087 (17)	2.9144 (15)	154.9 (15)
O4A—H1A⋯O3A	0.91 (2)	1.65 (2)	2.5531 (13)	173.7 (19)
O3B—H1B⋯O4B	1.18 (2)	1.23 (2)	2.4108 (12)	177 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .