1-(2-Chloro­benz­yl)-3-methyl-2,6-diphenyl­piperidine

Ramalingan, C.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812029200

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2300

https://doi.org/10.1107/S1600536812029200

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1-(2-Chlorobenzyl)-3-methyl-2,6-diphenylpiperidine

Chennan Ramalingan,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aCentre for Nanotechnology, Department of Chemistry, Kalasalingam University, Krishnankoil 626 126, Tamilnadu, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department and Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 June 2012; accepted 27 June 2012; online 30 June 2012)

In the title compound, C₂₅H₂₆ClN, the piperidine ring has a chair conformation with all ring substituents in equatorial positions. The dihedral angle formed between the chlorobenzene 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 molecules aggregate via π–π interactions occurring between chlorobenzene rings [centroid–centroid distance = 3.778 (2) Å] and these are linked into linear supramolecular chains along the a axis by C—H⋯π interactions 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_r = 375.92
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.074
wR(F²) = 0.185
S = 1.03
4678 reflections
244 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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) x, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029200/hb6872sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029200/hb6872Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029200/hb6872Isup3.cml

checkCIF report

Comment top

Piperidine derivatives are an important class of heterocyclic compounds with potential applications in medicinal chemistry as these can be frequently recognized in the structures of various synthetic targets as well as naturally occurring alkaloids (Ramalingan et al., 2004; Ramachandran et al., 2011). The title compound, (I), was designed and synthesized to evaluate its biological properties. The crystal structure determination was undertaken in order to establish conformational details.

In (I), Fig. 1, the piperidine ring has a chair conformation and all ring-substituents occupy equatorial positions. The dihedral angle formed between the C1–C6 benzene ring and the flanking C14–C19 and C20–C25 phenyl rings are 74.91 (18) and 47.86 (17)°, respectively; the dihedral angle between the phenyl rings is 58.93 (18)°. In a comparable molecule, having an extra C-bound methyl group (Ramalingan et al., 2012), these substituents were found to occupy the same positions. The chloro substituent is anti to the piperidine-N atom.

In the crystal packing, centrosymmetrically related molecules aggregate via π—π interactions occurring between chlorobenzene rings [inter-centroid distance = 3.778 (2) Å for symmetry operation 2 - x, 1 - y, 1 - z]. These are linked into linear supramolecular chains along the a axis by C—H···π interactions whereby a phenyl-H17 atom associates with the C20—C25 ring, Fig. 2 and Table 1. Chains aggregate into layers in the ab plane without specific intermolecular interactions between them, Fig. 3.

Related literature top

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 top

A starting material, 3-methyl-2,6-diphenylpiperidine, was synthesized from benzaldehyde, 2-butanone and ammonium acetate through a Mannich-type reaction (for a typical synthesis, see Ramalingan et al. (2004)) followed by standard Wolff-Kishner reduction using hydrazine hydrate in diethylene glycol. 1-(2-Chlorobenzyl)-3-methyl-2,6-diphenylpiperidine was then synthesized as follows. To a DMF solution (15 ml) of 3-methyl-2,6-diphenylpiperidine (1.26 g, 0.005 mol) was added potassium tert-butoxide (0.67 g, 0.006 mol). The mixture was stirred for 30 minutes and 2-chlorobenzyl bromide (0.78 ml, 0.006 mol) was added drop-wise. Stirring was continued overnight before aqueous work-up. Extraction with diethyl ether followed by column chromatography separation using n-hexane/ethyl acetate (100:4) as an eluent eventually provided the pure title compound as a white solid. Re-crystallization was performed by slow evaporation of its ethanolic solution which afforded colourless plates. M.pt: 352–353 K. Yield: 83%.

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain in (I) sustained by C—H···π and π—π interactions which are shown as orange and purple dashed lines, respectively
	Fig. 3. A view in projection down the a axis of the unit-cell contents for (I). The C—H···π and π—π interactions are shown as orange and purple dashed lines, respectively.

1-(2-Chlorobenzyl)-3-methyl-2,6-diphenylpiperidine top

Crystal data top

C₂₅H₂₆ClN	Z = 2
M_r = 375.92	F(000) = 400
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.034
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→13
T_min = 0.495, T_max = 1.000	l = −13→14
7033 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0541P)² + 1.0947P] where P = (F_o² + 2F_c²)/3
4678 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.72 e Å⁻³
12 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₅H₂₆ClN	γ = 111.065 (5)°
M_r = 375.92	V = 1025.32 (11) Å³
Triclinic, P1	Z = 2
a = 10.0878 (7) Å	Mo Kα radiation
b = 10.2837 (5) Å	µ = 0.20 mm⁻¹
c = 11.3583 (7) Å	T = 100 K
α = 94.150 (5)°	0.25 × 0.15 × 0.03 mm
β = 107.713 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4678 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2850 reflections with I > 2σ(I)
T_min = 0.495, T_max = 1.000	R_int = 0.034
7033 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	12 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.03	Δρ_max = 0.72 e Å⁻³
4678 reflections	Δρ_min = −0.47 e Å⁻³
244 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆ClN
M_r	375.92
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.0878 (7), 10.2837 (5), 11.3583 (7)
α, β, γ (°)	94.150 (5), 107.713 (6), 111.065 (5)
V (Å³)	1025.32 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.25 × 0.15 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.495, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7033, 4678, 2850
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.185, 1.03
No. of reflections	4678
No. of parameters	244
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.47

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1.

Footnotes

‡Additional correspondence author, e-mail: ramalinganc@gmail.com.

Acknowledgements

The authors are grateful for facilities provided by the Chairman/Management of Kalasalingam University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ramachandran, R., Rani, M., Senthan, S., Jeong, Y.-T. & Kabilan, S. (2011). Eur. J. Med. Chem. 46, 1926–1934. Web of Science CSD CrossRef CAS PubMed Google Scholar
Ramalingan, C., Balasubramanian, S., Kabilan, S. & Vasudevan, M. (2004). Eur. J. Med. Chem. 39, 527–533. Web of Science CrossRef PubMed CAS Google Scholar
Ramalingan, C., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2301–o2302. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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