1-(2-Chloro-benz-yl)-3-methyl-2,6-diphenyl-piperidine.

In the title compound, C(25)H(26)ClN, the piperidine ring has a chair conformation with all ring substituents in equatorial positions. The dihedral angle formed between the chloro-benzene ring and the flanking phenyl rings are 74.91 (18) and 47.86 (17)°. The chloro substituent is anti to the piperidine N atom. In the crystal, centrosymmetrically related mol-ecules aggregate via π-π inter-actions occurring between chloro-benzene rings [centroid-centroid distance = 3.778 (2) Å] and these are linked into linear supra-molecular chains along the a axis by C-H⋯π inter-actions occurring between the phenyl rings.

Related literature

For the biological activity of piperidine derivatives, see: Ramalingan et al. (2004 ▶); Ramachandran et al. (2011 ▶). For a related structure, see: Ramalingan et al. (2012 ▶).

Experimental

Crystal data

C25H26ClN

M = 375.92

Triclinic,

a = 10.0878 (7) Å

b = 10.2837 (5) Å

c = 11.3583 (7) Å

α = 94.150 (5)°

β = 107.713 (6)°

γ = 111.065 (5)°

V = 1025.32 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.25 × 0.15 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.495, T max = 1.000

7033 measured reflections

4678 independent reflections

2850 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.185

S = 1.03

4678 reflections

244 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029200/hb6872sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029200/hb6872Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029200/hb6872Isup3.cml

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

C25H26ClN	Z = 2
Mr = 375.92	F(000) = 400
Triclinic, P1	Dx = 1.218 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0878 (7) Å	Cell parameters from 1908 reflections
b = 10.2837 (5) Å	θ = 2.4–27.5°
c = 11.3583 (7) Å	µ = 0.20 mm−1
α = 94.150 (5)°	T = 100 K
β = 107.713 (6)°	Plate, colourless
γ = 111.065 (5)°	0.25 × 0.15 × 0.03 mm
V = 1025.32 (11) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4678 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2850 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→13
Tmin = 0.495, Tmax = 1.000	l = −13→14
7033 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0541P)2 + 1.0947P] where P = (Fo2 + 2Fc2)/3
4678 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.72 e Å−3
12 restraints	Δρmin = −0.47 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	0.71459 (12)	0.30264 (9)	0.23928 (9)	0.0512 (3)
C1	0.8802 (4)	0.4580 (4)	0.3038 (3)	0.0395 (8)
C2	1.0149 (5)	0.4438 (5)	0.3581 (3)	0.0522 (10)
H2	1.0170	0.3523	0.3591	0.063*
C3	1.1464 (5)	0.5651 (6)	0.4110 (4)	0.0622 (12)
H3	1.2396	0.5560	0.4494	0.075*
C4	1.1470 (4)	0.7006 (5)	0.4099 (3)	0.0482 (10)
H4	1.2386	0.7836	0.4462	0.058*
C5	1.0061 (4)	0.7099 (4)	0.3528 (3)	0.0395 (8)
H5	1.0039	0.8013	0.3505	0.047*
C6	0.8716 (3)	0.5909 (3)	0.3004 (3)	0.0284 (7)
N1	0.7224 (3)	0.7408 (2)	0.2310 (2)	0.0260 (6)
C7	0.7188 (3)	0.5974 (3)	0.2470 (3)	0.0287 (7)
H7A	0.6623	0.5315	0.1637	0.034*
H7B	0.6614	0.5625	0.3032	0.034*
C8	0.6816 (4)	0.7457 (3)	0.0938 (3)	0.0308 (7)
H8	0.5797	0.6671	0.0471	0.037*
C9	0.6704 (4)	0.8861 (3)	0.0710 (3)	0.0390 (8)
H9A	0.6383	0.8849	−0.0207	0.047*
H9B	0.7715	0.9652	0.1128	0.047*
C10	0.5567 (4)	0.9107 (4)	0.1226 (3)	0.0386 (8)
H10A	0.5526	1.0033	0.1086	0.046*
H10B	0.4542	0.8349	0.0773	0.046*
C11	0.6033 (4)	0.9101 (3)	0.2629 (3)	0.0367 (8)
H11	0.7050	0.9898	0.3071	0.044*
C12	0.6174 (4)	0.7696 (3)	0.2865 (3)	0.0289 (7)
H12	0.5145	0.6903	0.2462	0.035*
C13	0.4882 (5)	0.9353 (4)	0.3160 (3)	0.0508 (10)
H13A	0.4819	1.0256	0.2998	0.076*
H13B	0.5220	0.9390	0.4072	0.076*
H13C	0.3880	0.8573	0.2747	0.076*
C14	0.6717 (3)	0.7731 (3)	0.4273 (3)	0.0257 (6)
C15	0.8186 (4)	0.8583 (3)	0.5027 (3)	0.0373 (8)
H15	0.8873	0.9119	0.4653	0.045*
C16	0.8687 (4)	0.8678 (4)	0.6320 (3)	0.0425 (9)
H16	0.9714	0.9261	0.6822	0.051*
C17	0.7699 (4)	0.7930 (4)	0.6883 (3)	0.0430 (9)
H17	0.8030	0.8017	0.7773	0.052*
C18	0.6248 (5)	0.7071 (4)	0.6151 (3)	0.0537 (11)
H18	0.5566	0.6544	0.6532	0.064*
C19	0.5744 (4)	0.6950 (4)	0.4837 (3)	0.0443 (9)
H19	0.4730	0.6330	0.4333	0.053*
C20	0.7954 (4)	0.7211 (3)	0.0442 (3)	0.0299 (7)
C21	0.7525 (4)	0.5955 (3)	−0.0406 (3)	0.0367 (8)
H21	0.6511	0.5262	−0.0672	0.044*
C22	0.8556 (5)	0.5702 (4)	−0.0870 (3)	0.0459 (9)
H22	0.8247	0.4838	−0.1441	0.055*
C23	1.0022 (5)	0.6704 (4)	−0.0500 (3)	0.0488 (10)
H23	1.0730	0.6536	−0.0814	0.059*
C24	1.0459 (4)	0.7955 (4)	0.0331 (3)	0.0488 (10)
H24	1.1470	0.8651	0.0587	0.059*
C25	0.9436 (4)	0.8202 (4)	0.0791 (3)	0.0412 (9)
H25	0.9754	0.9071	0.1360	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0784 (7)	0.0327 (4)	0.0474 (5)	0.0239 (5)	0.0270 (5)	0.0073 (4)
C1	0.053 (2)	0.053 (2)	0.0308 (16)	0.0303 (18)	0.0270 (16)	0.0130 (15)
C2	0.069 (3)	0.083 (3)	0.039 (2)	0.054 (3)	0.035 (2)	0.023 (2)
C3	0.047 (2)	0.119 (4)	0.042 (2)	0.047 (3)	0.0269 (19)	0.024 (2)
C4	0.0341 (19)	0.082 (3)	0.0307 (18)	0.0177 (19)	0.0204 (15)	0.0145 (18)
C5	0.0325 (18)	0.052 (2)	0.0270 (16)	0.0060 (16)	0.0147 (15)	0.0051 (15)
C6	0.0312 (16)	0.0384 (17)	0.0195 (14)	0.0126 (14)	0.0158 (13)	0.0069 (12)
N1	0.0342 (14)	0.0246 (12)	0.0213 (12)	0.0102 (11)	0.0147 (11)	0.0053 (10)
C7	0.0316 (17)	0.0235 (14)	0.0290 (15)	0.0065 (13)	0.0140 (13)	0.0037 (12)
C8	0.0398 (18)	0.0295 (15)	0.0222 (14)	0.0105 (14)	0.0145 (14)	0.0025 (12)
C9	0.062 (2)	0.0353 (17)	0.0218 (15)	0.0190 (17)	0.0173 (16)	0.0092 (13)
C10	0.060 (2)	0.0386 (18)	0.0266 (16)	0.0283 (17)	0.0165 (16)	0.0123 (14)
C11	0.055 (2)	0.0365 (17)	0.0253 (15)	0.0243 (16)	0.0160 (15)	0.0082 (13)
C12	0.0338 (17)	0.0297 (15)	0.0243 (15)	0.0112 (13)	0.0136 (13)	0.0049 (12)
C13	0.070 (3)	0.058 (2)	0.042 (2)	0.038 (2)	0.026 (2)	0.0164 (18)
C14	0.0306 (16)	0.0254 (14)	0.0227 (14)	0.0107 (13)	0.0124 (13)	0.0040 (12)
C15	0.0389 (19)	0.0342 (17)	0.0284 (16)	0.0018 (15)	0.0147 (15)	0.0005 (14)
C16	0.042 (2)	0.046 (2)	0.0263 (16)	0.0095 (17)	0.0070 (16)	−0.0050 (15)
C17	0.062 (2)	0.0429 (19)	0.0227 (15)	0.0210 (18)	0.0136 (17)	0.0072 (14)
C18	0.059 (2)	0.060 (2)	0.038 (2)	0.009 (2)	0.0293 (19)	0.0197 (18)
C19	0.0365 (19)	0.050 (2)	0.0355 (18)	0.0038 (17)	0.0154 (16)	0.0078 (16)
C20	0.0413 (18)	0.0320 (16)	0.0189 (13)	0.0133 (14)	0.0157 (13)	0.0065 (12)
C21	0.045 (2)	0.0311 (16)	0.0293 (16)	0.0087 (15)	0.0151 (15)	0.0039 (13)
C22	0.072 (3)	0.046 (2)	0.0320 (18)	0.031 (2)	0.0261 (19)	0.0075 (16)
C23	0.059 (2)	0.076 (3)	0.0330 (18)	0.037 (2)	0.0304 (18)	0.0223 (19)
C24	0.045 (2)	0.065 (2)	0.0323 (18)	0.0119 (19)	0.0200 (17)	0.0140 (18)
C25	0.047 (2)	0.0412 (19)	0.0279 (16)	0.0066 (17)	0.0176 (16)	0.0005 (14)

Cl1—C1	1.746 (4)	C11—H11	1.0000
C1—C2	1.376 (5)	C12—C14	1.518 (4)
C1—C6	1.402 (5)	C12—H12	1.0000
C2—C3	1.376 (6)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.393 (6)	C13—H13C	0.9800
C3—H3	0.9500	C14—C15	1.372 (4)
C4—C5	1.413 (5)	C14—C19	1.381 (4)
C4—H4	0.9500	C15—C16	1.384 (4)
C5—C6	1.379 (4)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.379 (5)
C6—C7	1.504 (4)	C16—H16	0.9500
N1—C12	1.487 (4)	C17—C18	1.355 (5)
N1—C7	1.488 (4)	C17—H17	0.9500
N1—C8	1.496 (4)	C18—C19	1.402 (5)
C7—H7A	0.9900	C18—H18	0.9500
C7—H7B	0.9900	C19—H19	0.9500
C8—C20	1.511 (4)	C20—C25	1.384 (4)
C8—C9	1.523 (4)	C20—C21	1.395 (4)
C8—H8	1.0000	C21—C22	1.391 (5)
C9—C10	1.523 (5)	C21—H21	0.9500
C9—H9A	0.9900	C22—C23	1.374 (5)
C9—H9B	0.9900	C22—H22	0.9500
C10—C11	1.520 (4)	C23—C24	1.380 (5)
C10—H10A	0.9900	C23—H23	0.9500
C10—H10B	0.9900	C24—C25	1.378 (5)
C11—C12	1.536 (4)	C24—H24	0.9500
C11—C13	1.549 (5)	C25—H25	0.9500
C2—C1—C6	122.7 (4)	C13—C11—H11	108.3
C2—C1—Cl1	117.7 (3)	N1—C12—C14	109.9 (2)
C6—C1—Cl1	119.6 (3)	N1—C12—C11	112.0 (2)
C1—C2—C3	118.6 (4)	C14—C12—C11	109.8 (2)
C1—C2—H2	120.7	N1—C12—H12	108.3
C3—C2—H2	120.7	C14—C12—H12	108.3
C2—C3—C4	122.0 (4)	C11—C12—H12	108.3
C2—C3—H3	119.0	C11—C13—H13A	109.5
C4—C3—H3	119.0	C11—C13—H13B	109.5
C3—C4—C5	117.4 (4)	H13A—C13—H13B	109.5
C3—C4—H4	121.3	C11—C13—H13C	109.5
C5—C4—H4	121.3	H13A—C13—H13C	109.5
C6—C5—C4	122.2 (4)	H13B—C13—H13C	109.5
C6—C5—H5	118.9	C15—C14—C19	118.2 (3)
C4—C5—H5	118.9	C15—C14—C12	120.4 (3)
C5—C6—C1	117.1 (3)	C19—C14—C12	121.4 (3)
C5—C6—C7	123.5 (3)	C14—C15—C16	121.3 (3)
C1—C6—C7	119.4 (3)	C14—C15—H15	119.3
C12—N1—C7	108.8 (2)	C16—C15—H15	119.3
C12—N1—C8	112.7 (2)	C17—C16—C15	120.2 (3)
C7—N1—C8	108.9 (2)	C17—C16—H16	119.9
N1—C7—C6	115.3 (2)	C15—C16—H16	119.9
N1—C7—H7A	108.4	C18—C17—C16	119.3 (3)
C6—C7—H7A	108.4	C18—C17—H17	120.4
N1—C7—H7B	108.4	C16—C17—H17	120.4
C6—C7—H7B	108.4	C17—C18—C19	120.7 (3)
H7A—C7—H7B	107.5	C17—C18—H18	119.6
N1—C8—C20	110.2 (3)	C19—C18—H18	119.6
N1—C8—C9	111.0 (2)	C14—C19—C18	120.2 (3)
C20—C8—C9	111.2 (3)	C14—C19—H19	119.9
N1—C8—H8	108.1	C18—C19—H19	119.9
C20—C8—H8	108.1	C25—C20—C21	117.6 (3)
C9—C8—H8	108.1	C25—C20—C8	122.3 (3)
C8—C9—C10	110.8 (3)	C21—C20—C8	120.1 (3)
C8—C9—H9A	109.5	C22—C21—C20	121.1 (3)
C10—C9—H9A	109.5	C22—C21—H21	119.4
C8—C9—H9B	109.5	C20—C21—H21	119.4
C10—C9—H9B	109.5	C23—C22—C21	119.9 (3)
H9A—C9—H9B	108.1	C23—C22—H22	120.1
C11—C10—C9	110.0 (3)	C21—C22—H22	120.1
C11—C10—H10A	109.7	C22—C23—C24	119.6 (4)
C9—C10—H10A	109.7	C22—C23—H23	120.2
C11—C10—H10B	109.7	C24—C23—H23	120.2
C9—C10—H10B	109.7	C25—C24—C23	120.4 (3)
H10A—C10—H10B	108.2	C25—C24—H24	119.8
C10—C11—C12	110.2 (2)	C23—C24—H24	119.8
C10—C11—C13	110.3 (3)	C24—C25—C20	121.4 (3)
C12—C11—C13	111.4 (3)	C24—C25—H25	119.3
C10—C11—H11	108.3	C20—C25—H25	119.3
C12—C11—H11	108.3
C6—C1—C2—C3	−0.2 (5)	C10—C11—C12—N1	54.7 (4)
Cl1—C1—C2—C3	−179.1 (3)	C13—C11—C12—N1	177.5 (3)
C1—C2—C3—C4	−0.6 (5)	C10—C11—C12—C14	177.1 (3)
C2—C3—C4—C5	0.5 (5)	C13—C11—C12—C14	−60.1 (3)
C3—C4—C5—C6	0.5 (5)	N1—C12—C14—C15	52.4 (4)
C4—C5—C6—C1	−1.2 (4)	C11—C12—C14—C15	−71.3 (4)
C4—C5—C6—C7	175.6 (3)	N1—C12—C14—C19	−129.9 (3)
C2—C1—C6—C5	1.0 (4)	C11—C12—C14—C19	106.5 (4)
Cl1—C1—C6—C5	179.9 (2)	C19—C14—C15—C16	−0.7 (5)
C2—C1—C6—C7	−175.9 (3)	C12—C14—C15—C16	177.1 (3)
Cl1—C1—C6—C7	3.0 (4)	C14—C15—C16—C17	−1.3 (6)
C12—N1—C7—C6	−131.3 (2)	C15—C16—C17—C18	2.0 (6)
C8—N1—C7—C6	105.4 (3)	C16—C17—C18—C19	−0.8 (6)
C5—C6—C7—N1	11.4 (4)	C15—C14—C19—C18	1.9 (5)
C1—C6—C7—N1	−171.9 (3)	C12—C14—C19—C18	−175.9 (3)
C12—N1—C8—C20	177.9 (2)	C17—C18—C19—C14	−1.2 (6)
C7—N1—C8—C20	−61.2 (3)	N1—C8—C20—C25	−69.8 (4)
C12—N1—C8—C9	54.3 (3)	C9—C8—C20—C25	53.7 (4)
C7—N1—C8—C9	175.2 (3)	N1—C8—C20—C21	110.8 (3)
N1—C8—C9—C10	−56.3 (3)	C9—C8—C20—C21	−125.7 (3)
C20—C8—C9—C10	−179.4 (2)	C25—C20—C21—C22	0.9 (5)
C8—C9—C10—C11	58.1 (3)	C8—C20—C21—C22	−179.6 (3)
C9—C10—C11—C12	−56.7 (4)	C20—C21—C22—C23	−0.6 (5)
C9—C10—C11—C13	179.9 (3)	C21—C22—C23—C24	0.1 (5)
C7—N1—C12—C14	62.9 (3)	C22—C23—C24—C25	0.1 (5)
C8—N1—C12—C14	−176.1 (2)	C23—C24—C25—C20	0.2 (5)
C7—N1—C12—C11	−174.7 (2)	C21—C20—C25—C24	−0.8 (5)
C8—N1—C12—C11	−53.7 (3)	C8—C20—C25—C24	179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1i	0.95	2.83	3.692 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20–C25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg1i	0.95	2.83	3.692 (4)	151

Symmetry code: (i) .