(3E,5E)-3,5-Dibenzyl­idene-1-phenethyl­piperidin-4-one

Ali, M.A.; Choon, T.S.; Almansour, A.I.; Shahani, T.; Fun, H.-K.

doi:10.1107/S1600536811035744

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2605

https://doi.org/10.1107/S1600536811035744

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(3E,5E)-3,5-Dibenzylidene-1-phenethylpiperidin-4-one

Mohamed Ashraf Ali,^a Tan Soo Choon,^b Abdulrahman I. Almansour,^c Tara Shahani ^d and Hoong-Kun Fun ^d ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, ^bSchool of Physical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, ^cDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh, 11451, Saudi Arabia, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 18 August 2011; accepted 2 September 2011; online 14 September 2011)

In the title compound, C₂₇H₂₅NO, the piperidine ring adopts an envelope conformation with the N atom at the flap position. The two benzylidene-benzene rings are oriented at a dihedral angle of 8.5 (1)°. In the crystal, the molecules are linked into centrosymmetric dimers by pairs of intermolecular C—H⋯O hydrogen bonds. The dimers are connected via C—H⋯π interactions involving the phenyl rings.

Related literature

For the biological activity of piperidine compounds, see: Asano et al. (2000 ); Scriabine (1980 ); Watson et al. (2000 ); Risi (2008 ). For bond-length data, see: Allen et al. (1987 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₇H₂₅NO
M_r = 379.48
Monoclinic, P 2₁ /c
a = 11.4785 (2) Å
b = 5.8396 (1) Å
c = 30.9591 (5) Å
β = 106.412 (1)°
V = 1990.63 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.36 × 0.30 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.973, T_max = 0.992
21942 measured reflections
5877 independent reflections
4370 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.173
S = 1.08
5877 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are centroids of the C1–C6, C14–C19 and C22–C27 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.95	2.54	3.425 (3)	155
C15—H15A⋯O1ⁱ	0.95	2.49	3.345 (3)	150
C2—H2A⋯Cg3ⁱⁱ	0.95	2.88	3.579 (2)	131
C23—H23A⋯Cg1ⁱⁱⁱ	0.95	2.99	3.640 (2)	127
C26—H26A⋯Cg2^iv	0.95	2.89	3.556 (2)	128
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y-1, -z; (iii) -x+1, -y, -z; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035744/ci5200sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035744/ci5200Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035744/ci5200Isup3.cml

checkCIF report

Comment top

Piperidines are very important compounds because of their presence in numerous alkaloids, pharmaceuticals, agrochemical and as synthetic intermediates. Biologically active alkaloids of the substituted piperidine ring system have been targeted for their total or partial synthesis. During a fairly recent 10-year period, several thousand piperidine compounds have been mentioned in clinical and preclinical studies (Watson et al., 2000). Selective inhibition of a number of enzymes involved in the binding and processing of glycoproteins has rendered piperidine alkaloids as important tools in the study of biochemical pathways (Asano et al., 2000). Piperidine derivatives are found to possess pharmacological activity and form an essential part of the molecular structures of important drugs such as raloxifene and minoxidil (Risi, 2008). A new neuroleptics has found that the piperidine derivatives have high affinity for CNS (Scriabine, 1980).

In the title compound (Fig. 1), the piperidine (N1/C8–C12) ring is attached to three benzene (C1–C6), (C14–C19) and (C22–C27) rings via butane (C6–C8) and prop-1-ene (C20–C22) groups. The piperidine ring adopts an envelope conformation (Cremer & Pople, 1975) with puckering parameters of Q = 0.556 (2) Å, Θ = 60.3 (2)° and φ = 357.5 (2)°. Atom N1 deviates from the C8-C12 plane by 0.738 (2) Å. The two benzyl phenyl rings are oriented at a dihedral angle of 8.5 (1)°. The bond lengths (Allen et al.,1987) and angles are within normal ranges.

In the crystal structure (Fig. 2), intermolecular C15—H15A···O1 and C13—H13A···O1 hydrogen bonds link the molecules into centrosymmetric dimers each containing two R¹₂(6) ring motifs. In addition, the crystal structure is stabilized by C—H···π interactions (Table 1).

Related literature top

For the biological activity of piperidine compounds, see: Asano et al. (2000); Scriabine (1980); Watson et al. (2000); Risi (2008). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-phenethyl-4-piperonidone (0.001 mmol) and benzaldehyde (0.002 mmol) were dissolved in methanol (10 ml) and 30% sodium hydroxide solution (5 ml) was added. The mixture was stirred for 5 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice and then was neutralized with conentrated HCl. The precipitated solid was filtered, washed with water and recrystallized from ethanol to obtain the title compound as light yellow crystals.

Structure description top

For the biological activity of piperidine compounds, see: Asano et al. (2000); Scriabine (1980); Watson et al. (2000); Risi (2008). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

(3E,5E)-3,5-Dibenzylidene-1-phenethylpiperidin-4-one top

Crystal data top

C₂₇H₂₅NO	F(000) = 808
M_r = 379.48	D_x = 1.266 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5149 reflections
a = 11.4785 (2) Å	θ = 2.7–30.1°
b = 5.8396 (1) Å	µ = 0.08 mm⁻¹
c = 30.9591 (5) Å	T = 296 K
β = 106.412 (1)°	Plate, light yellow
V = 1990.63 (6) Å³	0.36 × 0.30 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5877 independent reflections
Radiation source: fine-focus sealed tube	4370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
φ and ω scans	θ_max = 30.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.973, T_max = 0.992	k = −8→8
21942 measured reflections	l = −43→43

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0585P)² + 1.7928P] where P = (F_o² + 2F_c²)/3
5877 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₇H₂₅NO	V = 1990.63 (6) Å³
M_r = 379.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4785 (2) Å	µ = 0.08 mm⁻¹
b = 5.8396 (1) Å	T = 296 K
c = 30.9591 (5) Å	0.36 × 0.30 × 0.11 mm
β = 106.412 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5877 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4370 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.992	R_int = 0.048
21942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.08	Δρ_max = 0.40 e Å⁻³
5877 reflections	Δρ_min = −0.28 e Å⁻³
262 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
O1	0.94565 (15)	0.2948 (3)	0.03565 (5)	0.0356 (4)
N1	0.66007 (14)	−0.1134 (3)	−0.01094 (5)	0.0206 (3)
C1	0.82777 (17)	−0.3600 (4)	0.13159 (7)	0.0236 (4)
H1A	0.8069	−0.4400	0.1037	0.028*
C2	0.80770 (18)	−0.4622 (4)	0.16937 (7)	0.0279 (4)
H2A	0.7710	−0.6092	0.1670	0.033*
C3	0.84119 (18)	−0.3500 (4)	0.21060 (7)	0.0293 (5)
H3A	0.8261	−0.4188	0.2363	0.035*
C4	0.89693 (18)	−0.1369 (4)	0.21413 (7)	0.0272 (4)
H4A	0.9221	−0.0614	0.2424	0.033*
C5	0.91570 (17)	−0.0350 (4)	0.17640 (6)	0.0235 (4)
H5A	0.9548	0.1099	0.1793	0.028*
C6	0.87861 (16)	−0.1397 (3)	0.13407 (6)	0.0204 (4)
C7	0.89514 (16)	−0.0098 (3)	0.09573 (6)	0.0205 (4)
H7A	0.9543	0.1083	0.1035	0.025*
C8	0.84016 (16)	−0.0302 (3)	0.05124 (6)	0.0196 (4)
C9	0.87531 (17)	0.1378 (4)	0.02060 (6)	0.0222 (4)
C10	0.82163 (16)	0.1054 (3)	−0.02901 (6)	0.0195 (4)
C11	0.72482 (17)	−0.0742 (3)	−0.04479 (6)	0.0212 (4)
H11A	0.6666	−0.0240	−0.0733	0.025*
H11B	0.7626	−0.2191	−0.0506	0.025*
C12	0.74518 (17)	−0.2049 (3)	0.03011 (6)	0.0210 (4)
H12A	0.7849	−0.3440	0.0226	0.025*
H12B	0.7001	−0.2486	0.0518	0.025*
C13	0.86363 (16)	0.2420 (3)	−0.05619 (6)	0.0207 (4)
H13A	0.9225	0.3511	−0.0411	0.025*
C14	0.83292 (16)	0.2494 (3)	−0.10568 (6)	0.0196 (4)
C15	0.86569 (17)	0.4483 (4)	−0.12484 (6)	0.0215 (4)
H15A	0.9045	0.5699	−0.1058	0.026*
C16	0.84249 (17)	0.4707 (4)	−0.17115 (6)	0.0236 (4)
H16A	0.8645	0.6075	−0.1835	0.028*
C17	0.78731 (17)	0.2938 (4)	−0.19943 (6)	0.0236 (4)
H17A	0.7717	0.3088	−0.2311	0.028*
C18	0.75506 (17)	0.0949 (4)	−0.18125 (7)	0.0238 (4)
H18A	0.7174	−0.0266	−0.2006	0.029*
C19	0.77752 (16)	0.0719 (3)	−0.13486 (6)	0.0213 (4)
H19A	0.7551	−0.0654	−0.1228	0.026*
C20	0.55955 (17)	−0.2752 (4)	−0.02625 (6)	0.0257 (4)
H20A	0.5255	−0.3081	−0.0009	0.031*
H20B	0.5918	−0.4207	−0.0346	0.031*
C21	0.45702 (17)	−0.1920 (4)	−0.06630 (6)	0.0279 (5)
H21A	0.3815	−0.2703	−0.0651	0.034*
H21B	0.4454	−0.0264	−0.0620	0.034*
C22	0.47052 (16)	−0.2249 (4)	−0.11326 (6)	0.0219 (4)
C23	0.42776 (17)	−0.0546 (4)	−0.14575 (7)	0.0250 (4)
H23A	0.3951	0.0829	−0.1376	0.030*
C24	0.43255 (18)	−0.0842 (4)	−0.18977 (7)	0.0301 (5)
H24A	0.4027	0.0320	−0.2116	0.036*
C25	0.48105 (19)	−0.2839 (4)	−0.20181 (7)	0.0321 (5)
H25A	0.4844	−0.3046	−0.2319	0.039*
C26	0.52451 (18)	−0.4527 (4)	−0.17005 (7)	0.0297 (5)
H26A	0.5584	−0.5888	−0.1782	0.036*
C27	0.51871 (17)	−0.4237 (4)	−0.12612 (7)	0.0254 (4)
H27A	0.5481	−0.5413	−0.1046	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0454 (9)	0.0320 (9)	0.0238 (7)	−0.0209 (8)	0.0005 (6)	0.0003 (7)
N1	0.0206 (7)	0.0229 (8)	0.0171 (7)	−0.0057 (7)	0.0032 (6)	0.0018 (6)
C1	0.0203 (8)	0.0207 (10)	0.0258 (9)	0.0000 (8)	−0.0002 (7)	0.0029 (8)
C2	0.0223 (9)	0.0249 (10)	0.0328 (10)	−0.0009 (8)	0.0017 (8)	0.0097 (9)
C3	0.0247 (9)	0.0348 (12)	0.0289 (10)	0.0011 (9)	0.0083 (8)	0.0088 (9)
C4	0.0256 (9)	0.0329 (12)	0.0231 (9)	0.0019 (9)	0.0068 (8)	0.0004 (9)
C5	0.0209 (8)	0.0227 (10)	0.0261 (9)	0.0000 (8)	0.0053 (7)	−0.0011 (8)
C6	0.0164 (8)	0.0202 (9)	0.0230 (9)	0.0015 (7)	0.0030 (7)	0.0027 (8)
C7	0.0203 (8)	0.0175 (9)	0.0230 (9)	−0.0006 (7)	0.0050 (7)	0.0022 (7)
C8	0.0202 (8)	0.0152 (9)	0.0222 (8)	−0.0015 (7)	0.0038 (7)	0.0004 (7)
C9	0.0221 (8)	0.0213 (10)	0.0210 (9)	−0.0039 (8)	0.0027 (7)	−0.0001 (8)
C10	0.0189 (8)	0.0195 (9)	0.0190 (8)	−0.0022 (7)	0.0034 (6)	−0.0019 (7)
C11	0.0213 (8)	0.0213 (10)	0.0206 (8)	−0.0056 (7)	0.0054 (7)	−0.0017 (7)
C12	0.0222 (8)	0.0197 (9)	0.0195 (8)	−0.0019 (7)	0.0032 (7)	0.0004 (7)
C13	0.0204 (8)	0.0197 (9)	0.0210 (8)	−0.0035 (7)	0.0039 (7)	−0.0024 (7)
C14	0.0169 (8)	0.0211 (9)	0.0215 (8)	−0.0014 (7)	0.0066 (6)	0.0001 (7)
C15	0.0212 (8)	0.0208 (9)	0.0226 (9)	−0.0043 (7)	0.0061 (7)	−0.0012 (8)
C16	0.0240 (9)	0.0224 (10)	0.0253 (9)	−0.0009 (8)	0.0085 (7)	0.0027 (8)
C17	0.0218 (8)	0.0286 (11)	0.0212 (8)	0.0009 (8)	0.0076 (7)	−0.0009 (8)
C18	0.0235 (9)	0.0231 (10)	0.0258 (9)	−0.0011 (8)	0.0082 (7)	−0.0052 (8)
C19	0.0221 (8)	0.0186 (9)	0.0246 (9)	−0.0023 (7)	0.0089 (7)	−0.0013 (8)
C20	0.0242 (9)	0.0311 (11)	0.0215 (9)	−0.0114 (9)	0.0056 (7)	−0.0004 (8)
C21	0.0216 (9)	0.0379 (12)	0.0242 (9)	−0.0059 (9)	0.0062 (7)	−0.0072 (9)
C22	0.0156 (8)	0.0251 (10)	0.0232 (9)	−0.0034 (7)	0.0026 (7)	−0.0033 (8)
C23	0.0189 (8)	0.0236 (10)	0.0309 (10)	−0.0015 (8)	0.0045 (7)	−0.0038 (8)
C24	0.0257 (9)	0.0349 (13)	0.0272 (10)	−0.0036 (9)	0.0034 (8)	0.0050 (9)
C25	0.0258 (10)	0.0464 (14)	0.0246 (10)	−0.0071 (10)	0.0079 (8)	−0.0083 (10)
C26	0.0216 (9)	0.0324 (12)	0.0347 (11)	−0.0006 (9)	0.0073 (8)	−0.0113 (10)
C27	0.0204 (8)	0.0242 (10)	0.0287 (10)	0.0007 (8)	0.0022 (7)	−0.0020 (8)

Geometric parameters (Å, º) top

O1—C9	1.223 (2)	C14—C15	1.403 (3)
N1—C20	1.463 (2)	C14—C19	1.404 (3)
N1—C11	1.464 (2)	C15—C16	1.388 (3)
N1—C12	1.467 (2)	C15—H15A	0.95
C1—C2	1.389 (3)	C16—C17	1.386 (3)
C1—C6	1.406 (3)	C16—H16A	0.95
C1—H1A	0.95	C17—C18	1.386 (3)
C2—C3	1.389 (3)	C17—H17A	0.95
C2—H2A	0.95	C18—C19	1.392 (3)
C3—C4	1.390 (3)	C18—H18A	0.95
C3—H3A	0.95	C19—H19A	0.95
C4—C5	1.381 (3)	C20—C21	1.528 (3)
C4—H4A	0.95	C20—H20A	0.99
C5—C6	1.399 (3)	C20—H20B	0.99
C5—H5A	0.95	C21—C22	1.517 (3)
C6—C7	1.466 (3)	C21—H21A	0.99
C7—C8	1.348 (2)	C21—H21B	0.99
C7—H7A	0.95	C22—C27	1.392 (3)
C8—C9	1.497 (3)	C22—C23	1.401 (3)
C8—C12	1.501 (3)	C23—C24	1.390 (3)
C9—C10	1.497 (3)	C23—H23A	0.95
C10—C13	1.344 (3)	C24—C25	1.388 (3)
C10—C11	1.506 (3)	C24—H24A	0.95
C11—H11A	0.99	C25—C26	1.382 (3)
C11—H11B	0.99	C25—H25A	0.95
C12—H12A	0.99	C26—C27	1.391 (3)
C12—H12B	0.99	C26—H26A	0.95
C13—C14	1.473 (3)	C27—H27A	0.95
C13—H13A	0.95

C20—N1—C11	112.49 (15)	C15—C14—C19	117.78 (17)
C20—N1—C12	108.47 (15)	C15—C14—C13	116.76 (17)
C11—N1—C12	109.18 (14)	C19—C14—C13	125.42 (18)
C2—C1—C6	120.81 (19)	C16—C15—C14	121.22 (18)
C2—C1—H1A	119.6	C16—C15—H15A	119.4
C6—C1—H1A	119.6	C14—C15—H15A	119.4
C3—C2—C1	120.2 (2)	C17—C16—C15	120.15 (19)
C3—C2—H2A	119.9	C17—C16—H16A	119.9
C1—C2—H2A	119.9	C15—C16—H16A	119.9
C2—C3—C4	119.76 (19)	C18—C17—C16	119.66 (18)
C2—C3—H3A	120.1	C18—C17—H17A	120.2
C4—C3—H3A	120.1	C16—C17—H17A	120.2
C5—C4—C3	119.9 (2)	C17—C18—C19	120.45 (19)
C5—C4—H4A	120.1	C17—C18—H18A	119.8
C3—C4—H4A	120.1	C19—C18—H18A	119.8
C4—C5—C6	121.7 (2)	C18—C19—C14	120.73 (18)
C4—C5—H5A	119.2	C18—C19—H19A	119.6
C6—C5—H5A	119.2	C14—C19—H19A	119.6
C5—C6—C1	117.59 (18)	N1—C20—C21	114.45 (18)
C5—C6—C7	117.23 (18)	N1—C20—H20A	108.6
C1—C6—C7	125.18 (18)	C21—C20—H20A	108.6
C8—C7—C6	130.63 (18)	N1—C20—H20B	108.6
C8—C7—H7A	114.7	C21—C20—H20B	108.6
C6—C7—H7A	114.7	H20A—C20—H20B	107.6
C7—C8—C9	117.20 (17)	C22—C21—C20	118.26 (17)
C7—C8—C12	125.30 (17)	C22—C21—H21A	107.7
C9—C8—C12	117.49 (16)	C20—C21—H21A	107.7
O1—C9—C10	121.46 (17)	C22—C21—H21B	107.7
O1—C9—C8	121.10 (17)	C20—C21—H21B	107.7
C10—C9—C8	117.44 (16)	H21A—C21—H21B	107.1
C13—C10—C9	116.80 (17)	C27—C22—C23	118.27 (18)
C13—C10—C11	124.95 (17)	C27—C22—C21	122.41 (19)
C9—C10—C11	118.25 (16)	C23—C22—C21	119.24 (19)
N1—C11—C10	110.74 (15)	C24—C23—C22	120.8 (2)
N1—C11—H11A	109.5	C24—C23—H23A	119.6
C10—C11—H11A	109.5	C22—C23—H23A	119.6
N1—C11—H11B	109.5	C25—C24—C23	119.9 (2)
C10—C11—H11B	109.5	C25—C24—H24A	120.1
H11A—C11—H11B	108.1	C23—C24—H24A	120.1
N1—C12—C8	110.72 (16)	C26—C25—C24	119.97 (19)
N1—C12—H12A	109.5	C26—C25—H25A	120.0
C8—C12—H12A	109.5	C24—C25—H25A	120.0
N1—C12—H12B	109.5	C25—C26—C27	120.1 (2)
C8—C12—H12B	109.5	C25—C26—H26A	119.9
H12A—C12—H12B	108.1	C27—C26—H26A	119.9
C10—C13—C14	130.25 (18)	C26—C27—C22	120.9 (2)
C10—C13—H13A	114.9	C26—C27—H27A	119.5
C14—C13—H13A	114.9	C22—C27—H27A	119.5

C6—C1—C2—C3	−1.9 (3)	C9—C8—C12—N1	−30.1 (2)
C1—C2—C3—C4	−1.2 (3)	C9—C10—C13—C14	178.07 (19)
C2—C3—C4—C5	1.8 (3)	C11—C10—C13—C14	−2.5 (3)
C3—C4—C5—C6	0.8 (3)	C10—C13—C14—C15	163.0 (2)
C4—C5—C6—C1	−3.8 (3)	C10—C13—C14—C19	−19.2 (3)
C4—C5—C6—C7	175.79 (18)	C19—C14—C15—C16	1.0 (3)
C2—C1—C6—C5	4.3 (3)	C13—C14—C15—C16	178.98 (17)
C2—C1—C6—C7	−175.19 (18)	C14—C15—C16—C17	−0.8 (3)
C5—C6—C7—C8	−158.6 (2)	C15—C16—C17—C18	0.2 (3)
C1—C6—C7—C8	20.9 (3)	C16—C17—C18—C19	0.1 (3)
C6—C7—C8—C9	177.81 (19)	C17—C18—C19—C14	0.1 (3)
C6—C7—C8—C12	−1.1 (3)	C15—C14—C19—C18	−0.6 (3)
C7—C8—C9—O1	−4.1 (3)	C13—C14—C19—C18	−178.45 (18)
C12—C8—C9—O1	174.81 (19)	C11—N1—C20—C21	−64.8 (2)
C7—C8—C9—C10	175.55 (17)	C12—N1—C20—C21	174.35 (16)
C12—C8—C9—C10	−5.5 (3)	N1—C20—C21—C22	83.7 (2)
O1—C9—C10—C13	6.6 (3)	C20—C21—C22—C27	40.6 (3)
C8—C9—C10—C13	−173.14 (17)	C20—C21—C22—C23	−142.6 (2)
O1—C9—C10—C11	−172.94 (19)	C27—C22—C23—C24	0.5 (3)
C8—C9—C10—C11	7.4 (3)	C21—C22—C23—C24	−176.47 (18)
C20—N1—C11—C10	175.99 (16)	C22—C23—C24—C25	−0.5 (3)
C12—N1—C11—C10	−63.6 (2)	C23—C24—C25—C26	0.0 (3)
C13—C10—C11—N1	−152.95 (19)	C24—C25—C26—C27	0.6 (3)
C9—C10—C11—N1	26.5 (2)	C25—C26—C27—C22	−0.6 (3)
C20—N1—C12—C8	−171.40 (16)	C23—C22—C27—C26	0.1 (3)
C11—N1—C12—C8	65.7 (2)	C21—C22—C27—C26	176.92 (18)
C7—C8—C12—N1	148.79 (19)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are centroids of the C1–C6, C14–C19 and C22–C27 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.95	2.54	3.425 (3)	155
C15—H15A···O1ⁱ	0.95	2.49	3.345 (3)	150
C2—H2A···Cg3ⁱⁱ	0.95	2.88	3.579 (2)	131
C23—H23A···Cg1ⁱⁱⁱ	0.95	2.99	3.640 (2)	127
C26—H26A···Cg2^iv	0.95	2.89	3.556 (2)	128

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y−1, −z; (iii) −x+1, −y, −z; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₅NO
M_r	379.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4785 (2), 5.8396 (1), 30.9591 (5)
β (°)	106.412 (1)
V (Å³)	1990.63 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.30 × 0.11

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.973, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	21942, 5877, 4370
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.173, 1.08
No. of reflections	5877
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are centroids of the C1–C6, C14–C19 and C22–C27 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.95	2.54	3.425 (3)	155
C15—H15A···O1ⁱ	0.95	2.49	3.345 (3)	150
C2—H2A···Cg3ⁱⁱ	0.95	2.88	3.579 (2)	131
C23—H23A···Cg1ⁱⁱⁱ	0.95	2.99	3.640 (2)	127
C26—H26A···Cg2^iv	0.95	2.89	3.556 (2)	128

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y−1, −z; (iii) −x+1, −y, −z; (iv) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

References

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