3-(4-Chloro-benzo-yl)-4-(4-chloro-phen-yl)-1-phenethyl-piperidin-4-ol.

In the title compound, C(26)H(25)Cl(2)NO(2), the piperidine ring adopts a chair conformation with a cis configuration of the carbonyl and hy-droxy substituents. The dihedral angle between the aromatic rings of the chloro-benzene groups is 24.3 (2)°. The phenyl ring forms dihedral angles of 59.4 (3) and 44.1 (3)° with the benzene rings. In the crystal, mol-ecules are linked by inter-molecular O-H⋯N and C-H⋯O hydrogen bonds and C-H⋯π inter-actions into layers parallel to the bc plane.

Related literature

For the synthesis and biological activity of Mannich bases, see: Dimmock et al. (1991 ▶); Dimmock & Kumar (1997) ▶; Gul et al. (2001 ▶, 2004 ▶, 2005 ▶); Atwal et al. (1969 ▶); Gul (2005 ▶); Erciyas et al. (1994 ▶); Porretta et al. (1995 ▶); Piscopo et al. (1986 ▶); Manavathu et al. (1998 ▶); Vashishtha et al. (1998 ▶); Canturk et al. (2008 ▶); Suleyman et al. (2007 ▶); Yogeeswari et al. (2005 ▶); Mete et al. (2010a ▶,b ▶) For MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985 ▶); Stewart (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H25Cl2NO2

M = 454.37

Monoclinic,

a = 16.950 (4) Å

b = 12.863 (3) Å

c = 10.792 (2) Å

β = 97.779 (13)°

V = 2331.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 294 K

0.23 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan [XABS2 (Parkin et al., 1995 ▶); cubic fit to sin(θ)/λ, 24 parameters] T min = 0.934, T max = 0.965

4830 measured reflections

4830 independent reflections

1939 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.097

wR(F 2) = 0.148

S = 1.07

4830 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018034/rz2590sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018034/rz2590Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018034/rz2590Isup3.cml

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

C26H25Cl2NO2	F(000) = 952
Mr = 454.37	Dx = 1.295 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5626 reflections
a = 16.950 (4) Å	θ = 2.4–30.5°
b = 12.863 (3) Å	µ = 0.30 mm−1
c = 10.792 (2) Å	T = 294 K
β = 97.779 (13)°	Block, colourless
V = 2331.3 (9) Å3	0.23 × 0.14 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	4830 independent reflections
Radiation source: Sealed Tube	1939 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.000
Detector resolution: 10.00 pixels mm-1	θmax = 26.5°, θmin = 2.4°
dtprofit.ref scans	h = −21→21
Absorption correction: multi-scan [XABS2 (Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters]	k = 0→16
Tmin = 0.934, Tmax = 0.965	l = 0→13
4830 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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0094P)2 + 1.4373P] where P = (Fo2 + 2Fc2)/3
4830 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.45921 (10)	0.30278 (16)	0.49332 (19)	0.1484 (10)
Cl2	0.47453 (11)	0.57277 (17)	0.1905 (2)	0.1803 (13)
O1	0.0660 (2)	0.3454 (2)	0.3384 (3)	0.0716 (12)
O2	0.08304 (19)	0.5228 (2)	0.1541 (3)	0.0769 (14)
N1	−0.0050 (2)	0.2257 (3)	0.0508 (3)	0.0590 (16)
C1	−0.1997 (4)	0.1029 (5)	−0.2619 (7)	0.112 (3)
C2	−0.2733 (7)	0.1035 (6)	−0.3331 (8)	0.146 (5)
C3	−0.3396 (5)	0.1102 (6)	−0.2802 (11)	0.136 (5)
C4	−0.3367 (5)	0.1168 (5)	−0.1543 (9)	0.128 (4)
C5	−0.2612 (4)	0.1186 (5)	−0.0817 (6)	0.106 (3)
C6	−0.1933 (3)	0.1121 (4)	−0.1342 (6)	0.074 (2)
C7	−0.1130 (3)	0.1128 (4)	−0.0571 (5)	0.089 (3)
C8	−0.0868 (3)	0.2217 (3)	−0.0146 (4)	0.0683 (17)
C9	0.0000 (3)	0.1708 (4)	0.1714 (4)	0.0685 (17)
C10	0.0822 (3)	0.1743 (3)	0.2431 (4)	0.0651 (17)
C11	0.1144 (3)	0.2856 (3)	0.2674 (4)	0.0601 (17)
C12	0.1052 (2)	0.3410 (3)	0.1367 (4)	0.0521 (17)
C13	0.0195 (2)	0.3339 (3)	0.0750 (4)	0.0598 (17)
C14	0.1317 (3)	0.4537 (4)	0.1482 (4)	0.0581 (17)
C15	0.2176 (3)	0.4812 (4)	0.1536 (4)	0.0581 (17)
C16	0.2732 (3)	0.4180 (4)	0.1104 (4)	0.070 (2)
C17	0.3525 (3)	0.4459 (4)	0.1192 (5)	0.089 (2)
C18	0.3752 (3)	0.5378 (5)	0.1759 (6)	0.096 (3)
C19	0.3223 (4)	0.6037 (4)	0.2184 (6)	0.102 (3)
C20	0.2425 (3)	0.5758 (4)	0.2084 (5)	0.082 (3)
C21	0.2001 (3)	0.2836 (4)	0.3290 (4)	0.0582 (17)
C22	0.2562 (3)	0.2166 (4)	0.2909 (4)	0.0733 (19)
C23	0.3354 (3)	0.2222 (4)	0.3407 (5)	0.087 (3)
C24	0.3593 (3)	0.2945 (5)	0.4313 (5)	0.084 (2)
C25	0.3063 (4)	0.3599 (4)	0.4732 (5)	0.085 (3)
C26	0.2267 (3)	0.3553 (4)	0.4218 (4)	0.0694 (19)
H1	−0.15410	0.09610	−0.30030	0.1340*
H1A	0.05700	0.31190	0.39960	0.1070*
H2	−0.27690	0.09920	−0.41970	0.1750*
H3	−0.38870	0.11030	−0.33040	0.1630*
H4	−0.38300	0.12010	−0.11710	0.1540*
H5	−0.25790	0.12430	0.00480	0.1270*
H7A	−0.07430	0.08360	−0.10570	0.1070*
H7B	−0.11450	0.06910	0.01580	0.1070*
H8A	−0.09080	0.26700	−0.08710	0.0820*
H8B	−0.12280	0.24810	0.04060	0.0820*
H9A	−0.01560	0.09880	0.15630	0.0820*
H9B	−0.03720	0.20210	0.22140	0.0820*
H10A	0.11810	0.13630	0.19680	0.0780*
H10B	0.08170	0.13950	0.32260	0.0780*
H12	0.13890	0.30470	0.08370	0.0620*
H13A	−0.01500	0.36600	0.12880	0.0720*
H13B	0.01370	0.37200	−0.00330	0.0720*
H16	0.25700	0.35460	0.07420	0.0840*
H17	0.38920	0.40320	0.08740	0.1060*
H19	0.33930	0.66710	0.25400	0.1220*
H20	0.20580	0.62000	0.23810	0.0990*
H22	0.24010	0.16680	0.23040	0.0880*
H23	0.37230	0.17720	0.31310	0.1040*
H25	0.32310	0.40760	0.53590	0.1020*
H26	0.19060	0.40100	0.45010	0.0830*

	U11	U22	U33	U12	U13	U23
Cl1	0.0835 (12)	0.1827 (19)	0.1682 (18)	−0.0113 (12)	−0.0226 (11)	−0.0167 (15)
Cl2	0.1017 (14)	0.190 (2)	0.243 (3)	−0.0701 (14)	0.0008 (15)	−0.0200 (18)
O1	0.086 (2)	0.076 (2)	0.058 (2)	0.0178 (19)	0.0290 (18)	0.0100 (17)
O2	0.084 (2)	0.063 (2)	0.085 (3)	0.0156 (19)	0.016 (2)	−0.0046 (19)
N1	0.063 (3)	0.059 (3)	0.056 (2)	−0.004 (2)	0.012 (2)	0.005 (2)
C1	0.121 (6)	0.112 (5)	0.103 (6)	−0.018 (4)	0.016 (5)	−0.025 (4)
C2	0.192 (10)	0.118 (6)	0.113 (7)	−0.012 (7)	−0.033 (8)	−0.029 (5)
C3	0.104 (7)	0.109 (6)	0.184 (10)	−0.020 (5)	−0.020 (7)	0.010 (7)
C4	0.100 (6)	0.117 (6)	0.171 (8)	−0.004 (4)	0.032 (6)	0.036 (6)
C5	0.076 (4)	0.131 (6)	0.112 (5)	−0.012 (4)	0.014 (4)	0.029 (4)
C6	0.077 (4)	0.067 (3)	0.079 (4)	−0.016 (3)	0.014 (4)	0.001 (3)
C7	0.078 (4)	0.074 (4)	0.114 (5)	−0.015 (3)	0.006 (4)	−0.002 (3)
C8	0.070 (3)	0.066 (3)	0.070 (3)	−0.001 (3)	0.013 (3)	0.005 (3)
C9	0.076 (3)	0.065 (3)	0.067 (3)	−0.003 (3)	0.019 (3)	0.014 (3)
C10	0.073 (3)	0.060 (3)	0.064 (3)	0.003 (3)	0.015 (3)	0.010 (3)
C11	0.070 (3)	0.063 (3)	0.049 (3)	0.012 (3)	0.014 (3)	0.002 (3)
C12	0.059 (3)	0.050 (3)	0.049 (3)	0.001 (2)	0.014 (2)	0.000 (2)
C13	0.068 (3)	0.059 (3)	0.054 (3)	0.003 (2)	0.014 (2)	0.002 (2)
C14	0.074 (3)	0.057 (3)	0.045 (3)	−0.003 (3)	0.014 (2)	0.002 (2)
C15	0.069 (3)	0.051 (3)	0.053 (3)	−0.007 (3)	0.004 (3)	0.010 (2)
C16	0.061 (3)	0.073 (4)	0.076 (4)	−0.005 (3)	0.007 (3)	−0.002 (3)
C17	0.073 (4)	0.094 (4)	0.098 (4)	−0.016 (3)	0.010 (3)	−0.004 (4)
C18	0.079 (4)	0.092 (5)	0.109 (5)	−0.025 (4)	−0.014 (4)	0.008 (4)
C19	0.118 (6)	0.068 (4)	0.112 (5)	−0.031 (4)	−0.013 (4)	−0.004 (4)
C20	0.101 (5)	0.061 (4)	0.082 (4)	−0.007 (3)	0.003 (3)	0.004 (3)
C21	0.071 (3)	0.060 (3)	0.044 (3)	0.009 (3)	0.009 (2)	0.006 (2)
C22	0.064 (3)	0.085 (4)	0.070 (3)	0.010 (3)	0.006 (3)	−0.010 (3)
C23	0.071 (4)	0.101 (5)	0.088 (4)	0.018 (3)	0.006 (3)	−0.007 (4)
C24	0.066 (4)	0.091 (4)	0.091 (4)	0.000 (3)	−0.002 (3)	0.008 (4)
C25	0.098 (5)	0.078 (4)	0.075 (4)	0.000 (3)	−0.004 (4)	−0.001 (3)
C26	0.087 (4)	0.063 (3)	0.060 (3)	0.012 (3)	0.017 (3)	0.006 (3)

Cl1—C24	1.738 (5)	C21—C22	1.386 (7)
Cl2—C18	1.729 (6)	C22—C23	1.379 (7)
O1—C11	1.422 (6)	C23—C24	1.370 (8)
O2—C14	1.220 (6)	C24—C25	1.353 (8)
O1—H1A	0.8200	C25—C26	1.389 (8)
N1—C9	1.473 (6)	C1—H1	0.9300
N1—C13	1.466 (5)	C2—H2	0.9300
N1—C8	1.469 (6)	C3—H3	0.9300
C1—C2	1.374 (13)	C4—H4	0.9300
C1—C6	1.373 (10)	C5—H5	0.9300
C2—C3	1.330 (15)	C7—H7A	0.9700
C3—C4	1.356 (15)	C7—H7B	0.9700
C4—C5	1.407 (11)	C8—H8A	0.9700
C5—C6	1.352 (9)	C8—H8B	0.9700
C6—C7	1.496 (8)	C9—H9A	0.9700
C7—C8	1.521 (7)	C9—H9B	0.9700
C9—C10	1.500 (7)	C10—H10A	0.9700
C10—C11	1.542 (6)	C10—H10B	0.9700
C11—C12	1.569 (6)	C12—H12	0.9800
C11—C21	1.514 (7)	C13—H13A	0.9700
C12—C14	1.518 (6)	C13—H13B	0.9700
C12—C13	1.517 (5)	C16—H16	0.9300
C14—C15	1.492 (7)	C17—H17	0.9300
C15—C16	1.373 (7)	C19—H19	0.9300
C15—C20	1.393 (7)	C20—H20	0.9300
C16—C17	1.382 (7)	C22—H22	0.9300
C17—C18	1.362 (8)	C23—H23	0.9300
C18—C19	1.358 (8)	C25—H25	0.9300
C19—C20	1.389 (8)	C26—H26	0.9300
C21—C26	1.391 (7)
C11—O1—H1A	109.00	C3—C2—H2	119.00
C8—N1—C9	110.2 (3)	C2—C3—H3	119.00
C8—N1—C13	110.2 (3)	C4—C3—H3	119.00
C9—N1—C13	108.5 (3)	C3—C4—H4	121.00
C2—C1—C6	120.2 (7)	C5—C4—H4	121.00
C1—C2—C3	121.1 (9)	C4—C5—H5	119.00
C2—C3—C4	121.1 (9)	C6—C5—H5	119.00
C3—C4—C5	117.8 (8)	C6—C7—H7A	109.00
C4—C5—C6	121.8 (7)	C6—C7—H7B	109.00
C1—C6—C5	118.0 (6)	C8—C7—H7A	109.00
C1—C6—C7	120.1 (5)	C8—C7—H7B	109.00
C5—C6—C7	121.9 (6)	H7A—C7—H7B	108.00
C6—C7—C8	112.3 (4)	N1—C8—H8A	109.00
N1—C8—C7	113.3 (4)	N1—C8—H8B	109.00
N1—C9—C10	112.3 (4)	C7—C8—H8A	109.00
C9—C10—C11	113.5 (4)	C7—C8—H8B	109.00
O1—C11—C10	112.2 (4)	H8A—C8—H8B	108.00
O1—C11—C12	104.1 (3)	N1—C9—H9A	109.00
C10—C11—C12	106.2 (3)	N1—C9—H9B	109.00
C10—C11—C21	110.8 (4)	C10—C9—H9A	109.00
C12—C11—C21	112.0 (4)	C10—C9—H9B	109.00
O1—C11—C21	111.2 (4)	H9A—C9—H9B	108.00
C11—C12—C13	109.9 (3)	C9—C10—H10A	109.00
C11—C12—C14	111.6 (3)	C9—C10—H10B	109.00
C13—C12—C14	110.4 (3)	C11—C10—H10A	109.00
N1—C13—C12	111.5 (3)	C11—C10—H10B	109.00
O2—C14—C12	120.4 (4)	H10A—C10—H10B	108.00
C12—C14—C15	120.4 (4)	C11—C12—H12	108.00
O2—C14—C15	119.2 (4)	C13—C12—H12	108.00
C14—C15—C16	123.9 (5)	C14—C12—H12	108.00
C14—C15—C20	117.5 (4)	N1—C13—H13A	109.00
C16—C15—C20	118.6 (5)	N1—C13—H13B	109.00
C15—C16—C17	121.9 (5)	C12—C13—H13A	109.00
C16—C17—C18	118.0 (5)	C12—C13—H13B	109.00
Cl2—C18—C19	119.1 (5)	H13A—C13—H13B	108.00
C17—C18—C19	122.3 (5)	C15—C16—H16	119.00
Cl2—C18—C17	118.6 (4)	C17—C16—H16	119.00
C18—C19—C20	119.5 (5)	C16—C17—H17	121.00
C15—C20—C19	119.6 (5)	C18—C17—H17	121.00
C11—C21—C26	120.2 (4)	C18—C19—H19	120.00
C22—C21—C26	117.2 (5)	C20—C19—H19	120.00
C11—C21—C22	122.4 (4)	C15—C20—H20	120.00
C21—C22—C23	121.5 (5)	C19—C20—H20	120.00
C22—C23—C24	119.5 (5)	C21—C22—H22	119.00
Cl1—C24—C23	119.7 (4)	C23—C22—H22	119.00
Cl1—C24—C25	119.3 (5)	C22—C23—H23	120.00
C23—C24—C25	121.0 (5)	C24—C23—H23	120.00
C24—C25—C26	119.6 (5)	C24—C25—H25	120.00
C21—C26—C25	121.2 (5)	C26—C25—H25	120.00
C2—C1—H1	120.00	C21—C26—H26	119.00
C6—C1—H1	120.00	C25—C26—H26	119.00
C1—C2—H2	120.00
C9—N1—C13—C12	62.1 (4)	C10—C11—C12—C14	177.6 (4)
C9—N1—C8—C7	−67.4 (5)	C14—C12—C13—N1	174.0 (3)
C13—N1—C8—C7	173.0 (4)	C11—C12—C14—O2	−96.0 (5)
C8—N1—C13—C12	−177.2 (3)	C13—C12—C14—O2	26.5 (6)
C13—N1—C9—C10	−58.3 (5)	C13—C12—C14—C15	−154.0 (4)
C8—N1—C9—C10	−179.0 (4)	C11—C12—C14—C15	83.5 (5)
C2—C1—C6—C7	−179.2 (6)	C11—C12—C13—N1	−62.5 (4)
C6—C1—C2—C3	−1.8 (11)	O2—C14—C15—C16	−159.1 (4)
C2—C1—C6—C5	1.9 (9)	O2—C14—C15—C20	22.4 (6)
C1—C2—C3—C4	0.1 (12)	C12—C14—C15—C16	21.5 (6)
C2—C3—C4—C5	1.4 (11)	C12—C14—C15—C20	−157.1 (4)
C3—C4—C5—C6	−1.2 (10)	C14—C15—C16—C17	−178.9 (4)
C4—C5—C6—C1	−0.4 (9)	C20—C15—C16—C17	−0.4 (7)
C4—C5—C6—C7	−179.3 (5)	C14—C15—C20—C19	178.4 (5)
C1—C6—C7—C8	102.4 (6)	C16—C15—C20—C19	−0.2 (7)
C5—C6—C7—C8	−78.7 (6)	C15—C16—C17—C18	1.9 (8)
C6—C7—C8—N1	−174.4 (4)	C16—C17—C18—Cl2	178.8 (4)
N1—C9—C10—C11	56.4 (5)	C16—C17—C18—C19	−2.9 (9)
C9—C10—C11—C12	−52.7 (5)	Cl2—C18—C19—C20	−179.3 (5)
C9—C10—C11—C21	−174.6 (4)	C17—C18—C19—C20	2.4 (10)
C9—C10—C11—O1	60.4 (5)	C18—C19—C20—C15	−0.8 (9)
C10—C11—C12—C13	54.7 (4)	C11—C21—C22—C23	174.2 (4)
O1—C11—C12—C13	−63.8 (4)	C26—C21—C22—C23	−1.5 (7)
O1—C11—C12—C14	59.0 (4)	C11—C21—C26—C25	−175.3 (4)
C21—C11—C12—C14	−61.3 (5)	C22—C21—C26—C25	0.5 (7)
O1—C11—C21—C22	168.5 (4)	C21—C22—C23—C24	1.0 (8)
O1—C11—C21—C26	−16.0 (6)	C22—C23—C24—Cl1	−179.4 (4)
C10—C11—C21—C22	43.0 (6)	C22—C23—C24—C25	0.5 (8)
C10—C11—C21—C26	−141.5 (4)	Cl1—C24—C25—C26	178.5 (4)
C12—C11—C21—C22	−75.4 (5)	C23—C24—C25—C26	−1.4 (8)
C12—C11—C21—C26	100.1 (5)	C24—C25—C26—C21	0.9 (8)
C21—C11—C12—C13	175.9 (3)

Cg2 and Cg3 are the centroids of the C15–C20 and C21–C26 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.82	2.11	2.879 (5)	155
C13—H13B···O2ii	0.97	2.54	3.372 (5)	144
C2—H2···Cg2iii	0.93	2.85	3.739 (9)	159
C16—H16···Cg3iv	0.93	2.85	3.646 (5)	144

	X-ray	AM1	X-ray	AM1
	Ring-2	Ring-2	Ring-3	Ring-3
Ring-1	59.5 (3)	69.47	44.2 (3)	89.21
Ring-2			24.4 (3)	28.56

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C15–C20 and C21–C26 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.82	2.11	2.879 (5)	155
C13—H13B⋯O2ii	0.97	2.54	3.372 (5)	144
C2—H2⋯Cg2iii	0.93	2.85	3.739 (9)	159
C16—H16⋯Cg3iv	0.93	2.85	3.646 (5)	144

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