(3E,5E)-3,5-Bis(naphthalen-1-yl­methyl­idene)piperidin-4-one

Kia, Y.; Osman, H.; Murugaiyah, V.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812006307

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o802-o803

doi:10.1107/S1600536812006307

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(3E,5E)-3,5-Bis(naphthalen-1-ylmethylidene)piperidin-4-one

Yalda Kia,^a Hasnah Osman,^a ‡ Vikneswaran Murugaiyah,^b Suhana Arshad ^c and Ibrahim Abdul Razak ^c ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 8 February 2012; accepted 13 February 2012; online 24 February 2012)

In the title compound, C₂₇H₂₁NO, the piperidine ring adopts a chair conformation. The mean plane through the piperidine ring makes dihedral angles of 49.27 (5) and 63.07 (5)° with the naphthalene ring systems. In the crystal, molecules are linked into dimers via pairs of intermolecular C—H⋯O interactions, generating ten-membered R₂²(10) ring motifs. C—H⋯π interactions further stabilize the crystal structure.

Related literature

For the biological activities of α,β-unsaturated ketones, see: Lee et al. (1971 ); Anke et al. (1981 ); Khodair et al. (1997 ); Murakami et al. (2002 ); El-Subbagh et al. (2000 ); El-Barbary et al. (1994 ); Dimmock et al. (1983 ). For ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Basiri et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For experimental preparation, see: Das et al. (2007 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₇H₂₁NO
M_r = 375.45
Monoclinic, P 2₁ /c
a = 9.4833 (2) Å
b = 10.0838 (2) Å
c = 20.3885 (4) Å
β = 101.513 (1)°
V = 1910.48 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.28 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.979, T_max = 0.992
21618 measured reflections
5644 independent reflections
4138 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.125
S = 1.02
5644 reflections
266 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O1ⁱ	0.99	2.48	3.3758 (17)	150
C26—H26A⋯Cg1ⁱⁱ	0.95	2.92	3.7532 (15)	147
C25—H25A⋯Cg2ⁱⁱ	0.95	2.70	3.4923 (16)	141
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536812006307/rz2710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006307/rz2710Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006307/rz2710Isup3.cml

checkCIF report

Comment top

Reaction of aldehydes and ketones through Claisen-Schmidt condensation leads to α,β-unsaturated ketones which shown diverse biological activities such as cytotoxic (Lee et al., 1971; Anke et al., 1981; Khodair et al., 1997), antitumor (Murakami et al., 2002; El-Subbagh et al., 2000) and antiviral activities (El-Barbary et al., 1994). The conjugated O═CH—CH═CH2 system is the moiety which promotes the bioactivities in the title compound (Lee et al., 1971). As reported by Dimmock et al. (1983), these class of compounds show cytotoxic activity without any subsidiary mutagenic and carcinogenic activities in human body.

The molecular structure is shown in Fig. 1. The piperidine ring (N1/C12–C16) adopts a chair conformation with puckering amplitude Q = 0.4308 (14) Å, θ = 40.80 (19)° and ϕ = 350.7 (3)° (Cremer & Pople, 1975). In addition, the mean plane through the piperidine ring makes dihedral angles of 49.27 (5) and 63.07 (5)° with the terminal naphthalene ring systems (C1–C10 and C18–C27), respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to those found in a the related structure (Basiri et al., 2011).

In the crystal packing (Fig. 2), molecules are linked into dimers via pairs of intermolecular C13—H13B···O1 interactions (Table 1), generating ten-membered R²₂(10) ring motifs (Bernstein et al., 1995). The crystal structure is further stabilized by the intermolecular C26—H26A···Cg1 and C25—H25A···Cg2 (Table 1) interactions (Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C10 rings, respectively).

Related literature top

For the biological activities of α,β-unsaturated ketones, see: Lee et al. (1971); Anke et al. (1981); Khodair et al. (1997); Murakami et al. (2002); El-Subbagh et al. (2000); El-Barbary et al. (1994); Dimmock et al. (1983). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For a related structure, see: Basiri et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For experimental preparation, see: Das et al. (2007). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

(3E,5E)-3,5-Bis(naphthalen-1-ylmethylene)piperidin-4-one was synthesized by the method described in the literature (Das et al., 2007). Briefly, the title compound was prepared by dropwise addition of 1-naphtaldehyde (1 mmol) to a stirred mixture of 4-piperidone (1 mmol) and acetic acid (50 ml) in the presence of HCl (g) as catalyst at room temperature. After 24 h, a yellow precipitate formed and the completion of the reaction was monitored by TLC. The precipitate was filtered and washed with water. The pure solid was then recrystallized from ethanol to afford the title compound as yellow crystals.

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 viewed along the b axis. H atoms not involved in intermolecular hydrogen interactions (dashed lines) have been omitted for clarity.

(3E,5E)-3,5-Bis(naphthalen-1-ylmethylidene)piperidin-4-one top

Crystal data top

C₂₇H₂₁NO	F(000) = 792
M_r = 375.45	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5698 reflections
a = 9.4833 (2) Å	θ = 2.7–29.9°
b = 10.0838 (2) Å	µ = 0.08 mm⁻¹
c = 20.3885 (4) Å	T = 100 K
β = 101.513 (1)°	Plate, yellow
V = 1910.48 (7) Å³	0.28 × 0.21 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5644 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→8
T_min = 0.979, T_max = 0.992	k = −13→14
21618 measured reflections	l = −28→28

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0539P)² + 0.7137P] where P = (F_o² + 2F_c²)/3
5644 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₇H₂₁NO	V = 1910.48 (7) Å³
M_r = 375.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4833 (2) Å	µ = 0.08 mm⁻¹
b = 10.0838 (2) Å	T = 100 K
c = 20.3885 (4) Å	0.28 × 0.21 × 0.10 mm
β = 101.513 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5644 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4138 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.992	R_int = 0.037
21618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.41 e Å⁻³
5644 reflections	Δρ_min = −0.19 e Å⁻³
266 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.20055 (10)	0.98893 (10)	0.10917 (5)	0.0220 (2)
N1	−0.17776 (13)	0.77264 (12)	0.07711 (6)	0.0221 (3)
C1	−0.17882 (15)	1.32180 (13)	0.12377 (7)	0.0184 (3)
C2	−0.06600 (16)	1.34358 (14)	0.18022 (7)	0.0222 (3)
H2A	0.0171	1.2887	0.1868	0.027*
C3	−0.07534 (17)	1.44260 (15)	0.22535 (8)	0.0274 (3)
H3A	0.0020	1.4567	0.2622	0.033*
C4	−0.19864 (18)	1.52344 (16)	0.21750 (8)	0.0310 (4)
H4A	−0.2053	1.5905	0.2495	0.037*
C5	−0.30899 (17)	1.50529 (15)	0.16367 (8)	0.0274 (3)
H5A	−0.3917	1.5604	0.1586	0.033*
C6	−0.30191 (15)	1.40587 (14)	0.11546 (7)	0.0209 (3)
C7	−0.41645 (16)	1.38733 (14)	0.05993 (7)	0.0233 (3)
H7A	−0.4982	1.4438	0.0544	0.028*
C8	−0.41112 (16)	1.28894 (14)	0.01388 (7)	0.0234 (3)
H8A	−0.4880	1.2785	−0.0235	0.028*
C9	−0.29140 (15)	1.20365 (14)	0.02233 (7)	0.0206 (3)
H9A	−0.2890	1.1357	−0.0097	0.025*
C10	−0.17705 (14)	1.21611 (13)	0.07607 (6)	0.0174 (3)
C11	−0.05484 (15)	1.12471 (13)	0.08701 (6)	0.0181 (3)
H11A	0.0365	1.1635	0.1039	0.022*
C12	−0.05458 (14)	0.99261 (13)	0.07631 (6)	0.0168 (3)
C13	−0.18459 (14)	0.90730 (13)	0.04956 (7)	0.0188 (3)
H13A	−0.2712	0.9519	0.0593	0.023*
H13B	−0.1962	0.9012	0.0003	0.023*
C14	−0.04589 (15)	0.70382 (14)	0.07028 (7)	0.0217 (3)
H14A	−0.0459	0.6913	0.0221	0.026*
H14B	−0.0449	0.6149	0.0909	0.026*
C15	0.08935 (14)	0.77746 (13)	0.10247 (6)	0.0173 (3)
C16	0.08796 (14)	0.92523 (13)	0.09686 (6)	0.0171 (3)
C17	0.20833 (15)	0.72198 (13)	0.13867 (6)	0.0185 (3)
H17A	0.2798	0.7811	0.1613	0.022*
C18	0.23999 (14)	0.57973 (13)	0.14716 (7)	0.0178 (3)
C19	0.21653 (15)	0.49547 (14)	0.09261 (7)	0.0211 (3)
H19A	0.1734	0.5291	0.0498	0.025*
C20	0.25547 (15)	0.36044 (14)	0.09939 (7)	0.0236 (3)
H20A	0.2389	0.3045	0.0611	0.028*
C21	0.31695 (15)	0.30915 (14)	0.16068 (7)	0.0221 (3)
H21A	0.3411	0.2177	0.1648	0.027*
C22	0.34447 (14)	0.39198 (14)	0.21777 (7)	0.0189 (3)
C23	0.41211 (15)	0.34198 (14)	0.28155 (7)	0.0228 (3)
H23A	0.4373	0.2508	0.2862	0.027*
C24	0.44152 (16)	0.42307 (15)	0.33632 (7)	0.0252 (3)
H24A	0.4891	0.3886	0.3783	0.030*
C25	0.40119 (15)	0.55807 (15)	0.33047 (7)	0.0238 (3)
H25A	0.4207	0.6138	0.3688	0.029*
C26	0.33416 (15)	0.60925 (14)	0.26995 (7)	0.0200 (3)
H26A	0.3062	0.6999	0.2670	0.024*
C27	0.30600 (14)	0.52860 (13)	0.21164 (7)	0.0171 (3)
H1N1	−0.1808 (18)	0.7776 (18)	0.1223 (9)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0211 (5)	0.0162 (5)	0.0274 (5)	0.0004 (4)	0.0013 (4)	−0.0002 (4)
N1	0.0224 (6)	0.0159 (6)	0.0273 (6)	0.0011 (5)	0.0037 (5)	0.0041 (5)
C1	0.0233 (7)	0.0136 (6)	0.0194 (6)	0.0007 (5)	0.0072 (5)	0.0015 (5)
C2	0.0239 (7)	0.0189 (7)	0.0244 (7)	0.0014 (6)	0.0064 (5)	−0.0019 (5)
C3	0.0323 (8)	0.0254 (8)	0.0243 (7)	−0.0021 (6)	0.0052 (6)	−0.0050 (6)
C4	0.0409 (9)	0.0239 (8)	0.0301 (8)	0.0032 (7)	0.0116 (7)	−0.0085 (6)
C5	0.0323 (8)	0.0211 (7)	0.0309 (8)	0.0076 (6)	0.0113 (6)	−0.0015 (6)
C6	0.0257 (7)	0.0151 (6)	0.0236 (7)	0.0026 (5)	0.0089 (5)	0.0023 (5)
C7	0.0254 (7)	0.0195 (7)	0.0257 (7)	0.0082 (6)	0.0071 (6)	0.0049 (5)
C8	0.0245 (7)	0.0229 (7)	0.0220 (7)	0.0048 (6)	0.0029 (5)	0.0036 (5)
C9	0.0264 (7)	0.0166 (7)	0.0191 (6)	0.0028 (5)	0.0053 (5)	0.0008 (5)
C10	0.0209 (6)	0.0128 (6)	0.0193 (6)	0.0014 (5)	0.0059 (5)	0.0013 (5)
C11	0.0203 (6)	0.0165 (6)	0.0176 (6)	0.0019 (5)	0.0039 (5)	0.0007 (5)
C12	0.0203 (6)	0.0148 (6)	0.0151 (6)	0.0026 (5)	0.0032 (5)	0.0014 (4)
C13	0.0200 (6)	0.0135 (6)	0.0222 (6)	0.0029 (5)	0.0024 (5)	0.0010 (5)
C14	0.0229 (7)	0.0139 (6)	0.0259 (7)	0.0020 (5)	−0.0010 (5)	0.0002 (5)
C15	0.0205 (6)	0.0128 (6)	0.0186 (6)	0.0016 (5)	0.0036 (5)	0.0000 (5)
C16	0.0216 (6)	0.0138 (6)	0.0155 (6)	0.0026 (5)	0.0028 (5)	−0.0005 (4)
C17	0.0206 (6)	0.0153 (6)	0.0190 (6)	0.0006 (5)	0.0022 (5)	−0.0002 (5)
C18	0.0166 (6)	0.0146 (6)	0.0217 (6)	0.0016 (5)	0.0026 (5)	0.0004 (5)
C19	0.0215 (7)	0.0186 (7)	0.0215 (7)	0.0026 (5)	0.0004 (5)	−0.0006 (5)
C20	0.0215 (7)	0.0184 (7)	0.0294 (7)	0.0016 (6)	0.0013 (6)	−0.0070 (5)
C21	0.0185 (7)	0.0137 (6)	0.0331 (7)	0.0012 (5)	0.0025 (5)	0.0001 (5)
C22	0.0146 (6)	0.0159 (6)	0.0260 (7)	0.0003 (5)	0.0036 (5)	0.0026 (5)
C23	0.0204 (7)	0.0176 (7)	0.0301 (7)	0.0015 (5)	0.0046 (6)	0.0078 (5)
C24	0.0226 (7)	0.0287 (8)	0.0233 (7)	0.0015 (6)	0.0023 (5)	0.0079 (6)
C25	0.0236 (7)	0.0273 (8)	0.0207 (7)	−0.0002 (6)	0.0049 (5)	0.0004 (5)
C26	0.0210 (7)	0.0161 (6)	0.0231 (7)	0.0017 (5)	0.0049 (5)	0.0002 (5)
C27	0.0152 (6)	0.0149 (6)	0.0211 (6)	0.0001 (5)	0.0032 (5)	0.0017 (5)

Geometric parameters (Å, º) top

O1—C16	1.2283 (16)	C13—H13A	0.9900
N1—C14	1.4610 (18)	C13—H13B	0.9900
N1—C13	1.4660 (17)	C14—C15	1.5136 (19)
N1—H1N1	0.928 (18)	C14—H14A	0.9900
C1—C2	1.4235 (19)	C14—H14B	0.9900
C1—C6	1.4251 (19)	C15—C17	1.3411 (18)
C1—C10	1.4451 (18)	C15—C16	1.4943 (18)
C2—C3	1.372 (2)	C17—C18	1.4686 (18)
C2—H2A	0.9500	C17—H17A	0.9500
C3—C4	1.408 (2)	C18—C19	1.3819 (18)
C3—H3A	0.9500	C18—C27	1.4344 (18)
C4—C5	1.369 (2)	C19—C20	1.410 (2)
C4—H4A	0.9500	C19—H19A	0.9500
C5—C6	1.415 (2)	C20—C21	1.371 (2)
C5—H5A	0.9500	C20—H20A	0.9500
C6—C7	1.416 (2)	C21—C22	1.414 (2)
C7—C8	1.374 (2)	C21—H21A	0.9500
C7—H7A	0.9500	C22—C23	1.4226 (19)
C8—C9	1.407 (2)	C22—C27	1.4242 (18)
C8—H8A	0.9500	C23—C24	1.367 (2)
C9—C10	1.3848 (19)	C23—H23A	0.9500
C9—H9A	0.9500	C24—C25	1.413 (2)
C10—C11	1.4626 (18)	C24—H24A	0.9500
C11—C12	1.3499 (18)	C25—C26	1.3711 (19)
C11—H11A	0.9500	C25—H25A	0.9500
C12—C16	1.4961 (18)	C26—C27	1.4210 (19)
C12—C13	1.5130 (18)	C26—H26A	0.9500

C14—N1—C13	112.12 (11)	N1—C14—C15	113.13 (11)
C14—N1—H1N1	108.5 (11)	N1—C14—H14A	109.0
C13—N1—H1N1	108.8 (11)	C15—C14—H14A	109.0
C2—C1—C6	118.03 (12)	N1—C14—H14B	109.0
C2—C1—C10	123.38 (12)	C15—C14—H14B	109.0
C6—C1—C10	118.55 (12)	H14A—C14—H14B	107.8
C3—C2—C1	121.04 (14)	C17—C15—C16	116.85 (12)
C3—C2—H2A	119.5	C17—C15—C14	125.52 (12)
C1—C2—H2A	119.5	C16—C15—C14	117.53 (11)
C2—C3—C4	120.54 (14)	O1—C16—C15	120.79 (12)
C2—C3—H3A	119.7	O1—C16—C12	121.31 (12)
C4—C3—H3A	119.7	C15—C16—C12	117.90 (12)
C5—C4—C3	119.88 (14)	C15—C17—C18	127.02 (12)
C5—C4—H4A	120.1	C15—C17—H17A	116.5
C3—C4—H4A	120.1	C18—C17—H17A	116.5
C4—C5—C6	121.12 (14)	C19—C18—C27	119.17 (12)
C4—C5—H5A	119.4	C19—C18—C17	120.63 (12)
C6—C5—H5A	119.4	C27—C18—C17	120.04 (12)
C5—C6—C7	120.91 (13)	C18—C19—C20	121.18 (13)
C5—C6—C1	119.36 (13)	C18—C19—H19A	119.4
C7—C6—C1	119.72 (13)	C20—C19—H19A	119.4
C8—C7—C6	120.98 (13)	C21—C20—C19	120.60 (13)
C8—C7—H7A	119.5	C21—C20—H20A	119.7
C6—C7—H7A	119.5	C19—C20—H20A	119.7
C7—C8—C9	119.77 (13)	C20—C21—C22	120.18 (13)
C7—C8—H8A	120.1	C20—C21—H21A	119.9
C9—C8—H8A	120.1	C22—C21—H21A	119.9
C10—C9—C8	121.78 (13)	C21—C22—C23	121.24 (13)
C10—C9—H9A	119.1	C21—C22—C27	119.81 (12)
C8—C9—H9A	119.1	C23—C22—C27	118.95 (13)
C9—C10—C1	119.13 (12)	C24—C23—C22	121.06 (13)
C9—C10—C11	122.35 (12)	C24—C23—H23A	119.5
C1—C10—C11	118.51 (12)	C22—C23—H23A	119.5
C12—C11—C10	128.62 (13)	C23—C24—C25	119.99 (13)
C12—C11—H11A	115.7	C23—C24—H24A	120.0
C10—C11—H11A	115.7	C25—C24—H24A	120.0
C11—C12—C16	115.70 (12)	C26—C25—C24	120.51 (14)
C11—C12—C13	126.27 (12)	C26—C25—H25A	119.7
C16—C12—C13	117.94 (11)	C24—C25—H25A	119.7
N1—C13—C12	114.71 (11)	C25—C26—C27	120.90 (13)
N1—C13—H13A	108.6	C25—C26—H26A	119.6
C12—C13—H13A	108.6	C27—C26—H26A	119.6
N1—C13—H13B	108.6	C26—C27—C22	118.56 (12)
C12—C13—H13B	108.6	C26—C27—C18	122.40 (12)
H13A—C13—H13B	107.6	C22—C27—C18	119.04 (12)

C6—C1—C2—C3	0.0 (2)	C14—C15—C16—O1	−164.86 (12)
C10—C1—C2—C3	−177.67 (14)	C17—C15—C16—C12	−161.14 (12)
C1—C2—C3—C4	1.3 (2)	C14—C15—C16—C12	15.56 (17)
C2—C3—C4—C5	−1.4 (2)	C11—C12—C16—O1	−14.65 (19)
C3—C4—C5—C6	0.2 (2)	C13—C12—C16—O1	168.69 (12)
C4—C5—C6—C7	179.89 (15)	C11—C12—C16—C15	164.93 (12)
C4—C5—C6—C1	1.1 (2)	C13—C12—C16—C15	−11.73 (17)
C2—C1—C6—C5	−1.2 (2)	C16—C15—C17—C18	−174.83 (13)
C10—C1—C6—C5	176.59 (13)	C14—C15—C17—C18	8.8 (2)
C2—C1—C6—C7	−179.99 (13)	C15—C17—C18—C19	46.2 (2)
C10—C1—C6—C7	−2.2 (2)	C15—C17—C18—C27	−138.58 (14)
C5—C6—C7—C8	−178.55 (14)	C27—C18—C19—C20	0.4 (2)
C1—C6—C7—C8	0.2 (2)	C17—C18—C19—C20	175.69 (13)
C6—C7—C8—C9	1.0 (2)	C18—C19—C20—C21	0.5 (2)
C7—C8—C9—C10	−0.3 (2)	C19—C20—C21—C22	−1.2 (2)
C8—C9—C10—C1	−1.7 (2)	C20—C21—C22—C23	−178.09 (13)
C8—C9—C10—C11	177.34 (13)	C20—C21—C22—C27	1.0 (2)
C2—C1—C10—C9	−179.42 (13)	C21—C22—C23—C24	178.48 (14)
C6—C1—C10—C9	2.94 (19)	C27—C22—C23—C24	−0.6 (2)
C2—C1—C10—C11	1.5 (2)	C22—C23—C24—C25	1.7 (2)
C6—C1—C10—C11	−176.17 (12)	C23—C24—C25—C26	−0.8 (2)
C9—C10—C11—C12	−37.3 (2)	C24—C25—C26—C27	−1.1 (2)
C1—C10—C11—C12	141.76 (14)	C25—C26—C27—C22	2.1 (2)
C10—C11—C12—C16	−176.09 (12)	C25—C26—C27—C18	−178.11 (13)
C10—C11—C12—C13	0.3 (2)	C21—C22—C27—C26	179.62 (13)
C14—N1—C13—C12	−53.18 (15)	C23—C22—C27—C26	−1.27 (19)
C11—C12—C13—N1	−145.86 (13)	C21—C22—C27—C18	−0.15 (19)
C16—C12—C13—N1	30.42 (17)	C23—C22—C27—C18	178.96 (12)
C13—N1—C14—C15	56.73 (15)	C19—C18—C27—C26	179.70 (13)
N1—C14—C15—C17	138.38 (14)	C17—C18—C27—C26	4.4 (2)
N1—C14—C15—C16	−38.00 (17)	C19—C18—C27—C22	−0.54 (19)
C17—C15—C16—O1	18.44 (19)	C17—C18—C27—C22	−175.85 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1ⁱ	0.99	2.48	3.3758 (17)	150
C26—H26A···Cg1ⁱⁱ	0.95	2.92	3.7532 (15)	147
C25—H25A···Cg2ⁱⁱ	0.95	2.70	3.4923 (16)	141

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁NO
M_r	375.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.4833 (2), 10.0838 (2), 20.3885 (4)
β (°)	101.513 (1)
V (Å³)	1910.48 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.21 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.979, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	21618, 5644, 4138
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.125, 1.02
No. of reflections	5644
No. of parameters	266
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.19

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1ⁱ	0.9900	2.4800	3.3758 (17)	150.00
C26—H26A···Cg1ⁱⁱ	0.9500	2.9200	3.7532 (15)	147.00
C25—H25A···Cg2ⁱⁱ	0.9500	2.7000	3.4923 (16)	141.00

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

Footnotes

‡Additional correspondence author, e-mail: ohasnah@usm.my.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the FRGS grant No. 203/PKIMIA/6711179 and the Research University grant No. 1001/PFIZIK/811151 to conduct this work. YK thanks USM for providing research facility.

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Volume 68| Part 3| March 2012| Pages o802-o803

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