(E)-1-(2-Methyl-4-phenyl­quinolin-3-yl)-3-phenyl­prop-2-en-1-one

Loh, W.-S.; Fun, H.-K.; Prasath, R.; Sarveswari, S.; Vijayakumar, V.

doi:10.1107/S1600536811007057

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o764-o765

doi:10.1107/S1600536811007057

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(E)-1-(2-Methyl-4-phenylquinolin-3-yl)-3-phenylprop-2-en-1-one

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ R. Prasath,^b S. Sarveswari ^b and V. Vijayakumar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 20 February 2011; accepted 24 February 2011; online 2 March 2011)

In the title compound, C₂₅H₁₉NO, the quinoline ring system is approximately planar, with a maximum deviation of 0.32 (1) Å, and forms dihedral angles of 80.74 (3) and 81.71 (4)° with the two phenyl rings. In the crystal. molecules are stacked along the b axis by way of a C—H⋯π interaction and a weak π–π interaction between the pyridine and phenyl rings with a centroid–centroid distance of 3.6924 (5) Å.

Related literature

For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991 ); Michael (1997 ); Markees et al. (1970 ); Campbell et al. (1988); Maguire et al. (1994 ); Chen et al. (2001 ). For the biological activity of chalcones, see: Dimmock et al. (1999 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Loh, Fun, Sarveswari et al. (2010 ); Loh, Fun, Viji et al. (2010 ); Shahani et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₅H₁₉NO
M_r = 349.41
Monoclinic, P 2₁ /c
a = 10.5830 (5) Å
b = 10.2189 (5) Å
c = 18.4509 (7) Å
β = 114.147 (2)°
V = 1820.80 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.57 × 0.48 × 0.35 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.957, T_max = 0.973
27166 measured reflections
6509 independent reflections
5734 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.125
S = 1.05
6509 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C20–C25 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg3ⁱ	0.93	2.72	3.5265 (10)	146
Symmetry code: (i) 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: 10.1107/S1600536811007057/is2680sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007057/is2680Isup2.hkl

checkCIF report

Comment top

The quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991; Michael, 1997) and biologically active compounds (Markees et al., 1970; Campbell et al., 1988). A large variety of quinolines have interesting physiological activities and found to have attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Maguire et al., 1994; Chen et al., 2001). The chalcones are open chain flavonoids, possessed a variety of biological activities, including antioxidant, anti-inflammation, antimicrobial, antiprotozoal, antiulcer, as well as other properties (Dimmock et al., 1999). In continuation of our interest in the synthesis of chalcone derivatives (Loh, Fun, Sarveswari et al. (2010); Loh, Fun, Viji et al. (2010); Shahani et al., 2010), herein we report another new chalcone.

In the title compound (Fig. 1), the quinoline ring system (C7–C13/N1/C14/C15) is aproximately planar with a maximum deviation of 0.32 (1) Å at atom C15 and forms dihedral angles of 80.74 (3) and 81.71 (4)° with the C1–C6 and C20–C25 phenyl rings, respectively. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

There are no significant intermolecular hydrogen bonds observed in the crystal packing (Fig. 2). The molecules are stacked along the b axis by way of a C–H···π interaction (Table 1) which involves the phenyl ring (C20–C25) and a weak aromatic π–π interaction between the pyridine (N1/C13/C8/C7/C15/C14; centroid Cg1) and phenyl (C8–C13; centroid Cg2) rings with a separation of Cg1···Cg2 being 3.6924 (5) Å.

Related literature top

For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991); Michael (1997); Markees et al. (1970); Campbell et al. (1988); Maguire et al. (1994); Chen et al. (2001). For the biological activity of chalcones, see: Dimmock et al. (1999). For bond-length data, see: Allen et al. (1987). For related structures, see: Loh, Fun, Sarveswari et al. (2010); Loh, Fun, Viji et al. (2010); Shahani et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g, 0.01 M) and benzaldehyde (1.06 g, 0.01 M) and a catalytic amount of KOH in 40 ml of distilled ethanol was stirred for about 12 h. The resulting mixture was concentrated to remove ethanol and then poured onto ice and neutralized with distilled acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of ethylacetate and petroleum ether. Recrystallization was done in (8:4) petroleum ether, acetone mixture (m.p.: 422–423 K, yield: 82%).

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 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis.

(E)-1-(2-Methyl-4-phenylquinolin-3-yl)-3-phenylprop-2-en-1-one top

Crystal data top

C₂₅H₁₉NO	F(000) = 736
M_r = 349.41	D_x = 1.275 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9875 reflections
a = 10.5830 (5) Å	θ = 2.9–35.1°
b = 10.2189 (5) Å	µ = 0.08 mm⁻¹
c = 18.4509 (7) Å	T = 100 K
β = 114.147 (2)°	Block, colourless
V = 1820.80 (14) Å³	0.57 × 0.48 × 0.35 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	6509 independent reflections
Radiation source: fine-focus sealed tube	5734 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 32.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.957, T_max = 0.973	k = −15→15
27166 measured reflections	l = −27→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0699P)² + 0.5003P] where P = (F_o² + 2F_c²)/3
6509 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₅H₁₉NO	V = 1820.80 (14) Å³
M_r = 349.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5830 (5) Å	µ = 0.08 mm⁻¹
b = 10.2189 (5) Å	T = 100 K
c = 18.4509 (7) Å	0.57 × 0.48 × 0.35 mm
β = 114.147 (2)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	6509 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5734 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.973	R_int = 0.024
27166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	Δρ_max = 0.45 e Å⁻³
6509 reflections	Δρ_min = −0.17 e Å⁻³
245 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	0.08254 (7)	0.61008 (7)	0.74003 (4)	0.02139 (13)
N1	0.08585 (7)	0.73133 (7)	0.97579 (4)	0.01550 (13)
C1	0.41109 (8)	0.42498 (8)	0.90617 (5)	0.01661 (14)
H1A	0.4621	0.5004	0.9272	0.020*
C2	0.47170 (8)	0.32137 (9)	0.88288 (5)	0.01897 (15)
H2A	0.5635	0.3273	0.8895	0.023*
C3	0.39571 (9)	0.20934 (8)	0.84990 (5)	0.01841 (15)
H3A	0.4361	0.1406	0.8340	0.022*
C4	0.25883 (9)	0.20050 (8)	0.84073 (5)	0.01956 (15)
H4A	0.2073	0.1260	0.8182	0.023*
C5	0.19882 (8)	0.30296 (8)	0.86519 (5)	0.01787 (15)
H5A	0.1077	0.2959	0.8596	0.021*
C6	0.27412 (8)	0.41613 (7)	0.89806 (4)	0.01322 (13)
C7	0.20915 (7)	0.52474 (7)	0.92505 (4)	0.01297 (13)
C8	0.19789 (7)	0.51611 (7)	0.99939 (5)	0.01355 (13)
C9	0.24715 (8)	0.40797 (8)	1.05160 (5)	0.01717 (14)
H9A	0.2860	0.3367	1.0369	0.021*
C10	0.23797 (9)	0.40762 (9)	1.12373 (5)	0.02067 (16)
H10A	0.2705	0.3361	1.1575	0.025*
C11	0.17939 (9)	0.51514 (9)	1.14689 (5)	0.02056 (16)
H11A	0.1737	0.5143	1.1959	0.025*
C12	0.13073 (8)	0.62094 (8)	1.09741 (5)	0.01782 (15)
H12A	0.0927	0.6916	1.1132	0.021*
C13	0.13791 (7)	0.62353 (7)	1.02254 (5)	0.01411 (13)
C14	0.09416 (8)	0.73623 (7)	0.90660 (5)	0.01470 (14)
C15	0.15863 (7)	0.63547 (7)	0.87976 (4)	0.01344 (13)
C16	0.02989 (9)	0.85248 (8)	0.85478 (5)	0.02108 (16)
H16A	0.0019	0.9152	0.8841	0.032*
H16B	−0.0495	0.8248	0.8089	0.032*
H16C	0.0962	0.8918	0.8383	0.032*
C17	0.17065 (8)	0.65370 (7)	0.80187 (5)	0.01473 (14)
C18	0.28930 (8)	0.72866 (8)	0.80195 (5)	0.01588 (14)
H18A	0.2986	0.7388	0.7543	0.019*
C19	0.38512 (8)	0.78330 (7)	0.86795 (5)	0.01505 (14)
H19A	0.3747	0.7692	0.9150	0.018*
C20	0.50375 (8)	0.86236 (7)	0.87345 (5)	0.01548 (14)
C21	0.59080 (9)	0.91308 (8)	0.94763 (5)	0.01973 (15)
H21A	0.5724	0.8954	0.9918	0.024*
C22	0.70455 (9)	0.98962 (9)	0.95593 (6)	0.02567 (19)
H22A	0.7613	1.0235	1.0054	0.031*
C23	0.73351 (10)	1.01549 (9)	0.89041 (7)	0.02676 (19)
H23A	0.8094	1.0669	0.8959	0.032*
C24	0.64859 (10)	0.96426 (9)	0.81659 (6)	0.02460 (18)
H24A	0.6686	0.9807	0.7728	0.030*
C25	0.53413 (9)	0.88875 (8)	0.80779 (5)	0.01951 (15)
H25A	0.4774	0.8556	0.7581	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0222 (3)	0.0224 (3)	0.0164 (3)	−0.0036 (2)	0.0046 (2)	−0.0036 (2)
N1	0.0142 (3)	0.0149 (3)	0.0177 (3)	0.0010 (2)	0.0069 (2)	−0.0011 (2)
C1	0.0147 (3)	0.0170 (3)	0.0190 (3)	−0.0005 (2)	0.0079 (3)	−0.0020 (3)
C2	0.0164 (3)	0.0214 (4)	0.0209 (4)	0.0032 (3)	0.0095 (3)	−0.0004 (3)
C3	0.0228 (4)	0.0170 (3)	0.0172 (3)	0.0055 (3)	0.0099 (3)	0.0002 (3)
C4	0.0227 (4)	0.0153 (3)	0.0216 (4)	−0.0007 (3)	0.0100 (3)	−0.0044 (3)
C5	0.0163 (3)	0.0165 (3)	0.0216 (4)	−0.0016 (3)	0.0085 (3)	−0.0045 (3)
C6	0.0141 (3)	0.0129 (3)	0.0133 (3)	0.0012 (2)	0.0063 (2)	0.0000 (2)
C7	0.0123 (3)	0.0124 (3)	0.0147 (3)	−0.0005 (2)	0.0059 (2)	−0.0013 (2)
C8	0.0128 (3)	0.0130 (3)	0.0154 (3)	−0.0009 (2)	0.0064 (2)	−0.0007 (2)
C9	0.0201 (3)	0.0146 (3)	0.0174 (3)	0.0008 (3)	0.0083 (3)	0.0013 (3)
C10	0.0257 (4)	0.0188 (4)	0.0178 (4)	−0.0002 (3)	0.0093 (3)	0.0028 (3)
C11	0.0243 (4)	0.0231 (4)	0.0171 (3)	−0.0025 (3)	0.0114 (3)	−0.0006 (3)
C12	0.0184 (3)	0.0198 (3)	0.0182 (3)	−0.0017 (3)	0.0106 (3)	−0.0027 (3)
C13	0.0125 (3)	0.0145 (3)	0.0162 (3)	−0.0010 (2)	0.0068 (2)	−0.0016 (2)
C14	0.0139 (3)	0.0130 (3)	0.0165 (3)	0.0007 (2)	0.0054 (2)	−0.0008 (2)
C15	0.0131 (3)	0.0127 (3)	0.0146 (3)	−0.0005 (2)	0.0057 (2)	−0.0008 (2)
C16	0.0247 (4)	0.0167 (3)	0.0204 (4)	0.0068 (3)	0.0077 (3)	0.0025 (3)
C17	0.0165 (3)	0.0125 (3)	0.0148 (3)	0.0011 (2)	0.0061 (3)	0.0000 (2)
C18	0.0188 (3)	0.0154 (3)	0.0144 (3)	−0.0010 (2)	0.0078 (3)	0.0007 (2)
C19	0.0166 (3)	0.0146 (3)	0.0150 (3)	0.0001 (2)	0.0075 (3)	0.0007 (2)
C20	0.0163 (3)	0.0130 (3)	0.0180 (3)	0.0005 (2)	0.0078 (3)	0.0006 (2)
C21	0.0189 (3)	0.0182 (3)	0.0204 (4)	−0.0008 (3)	0.0064 (3)	−0.0012 (3)
C22	0.0199 (4)	0.0217 (4)	0.0310 (5)	−0.0037 (3)	0.0060 (3)	−0.0046 (3)
C23	0.0211 (4)	0.0192 (4)	0.0429 (6)	−0.0039 (3)	0.0161 (4)	−0.0020 (4)
C24	0.0265 (4)	0.0203 (4)	0.0351 (5)	−0.0021 (3)	0.0209 (4)	0.0006 (3)
C25	0.0228 (4)	0.0178 (3)	0.0220 (4)	−0.0016 (3)	0.0133 (3)	−0.0005 (3)

Geometric parameters (Å, º) top

O1—C17	1.2244 (10)	C12—C13	1.4143 (11)
N1—C14	1.3159 (10)	C12—H12A	0.9300
N1—C13	1.3683 (10)	C14—C15	1.4309 (10)
C1—C2	1.3939 (11)	C14—C16	1.5020 (11)
C1—C6	1.3980 (10)	C15—C17	1.5054 (11)
C1—H1A	0.9300	C16—H16A	0.9600
C2—C3	1.3882 (12)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.3910 (12)	C17—C18	1.4704 (11)
C3—H3A	0.9300	C18—C19	1.3464 (11)
C4—C5	1.3920 (11)	C18—H18A	0.9300
C4—H4A	0.9300	C19—C20	1.4611 (11)
C5—C6	1.3946 (11)	C19—H19A	0.9300
C5—H5A	0.9300	C20—C21	1.3997 (12)
C6—C7	1.4942 (10)	C20—C25	1.4009 (11)
C7—C15	1.3781 (10)	C21—C22	1.3905 (12)
C7—C8	1.4272 (11)	C21—H21A	0.9300
C8—C9	1.4178 (11)	C22—C23	1.3887 (15)
C8—C13	1.4186 (10)	C22—H22A	0.9300
C9—C10	1.3734 (12)	C23—C24	1.3912 (15)
C9—H9A	0.9300	C23—H23A	0.9300
C10—C11	1.4110 (13)	C24—C25	1.3886 (12)
C10—H10A	0.9300	C24—H24A	0.9300
C11—C12	1.3723 (12)	C25—H25A	0.9300
C11—H11A	0.9300

C14—N1—C13	118.22 (7)	N1—C14—C15	122.61 (7)
C2—C1—C6	120.38 (7)	N1—C14—C16	117.07 (7)
C2—C1—H1A	119.8	C15—C14—C16	120.31 (7)
C6—C1—H1A	119.8	C7—C15—C14	120.18 (7)
C3—C2—C1	120.29 (7)	C7—C15—C17	121.14 (7)
C3—C2—H2A	119.9	C14—C15—C17	118.68 (6)
C1—C2—H2A	119.9	C14—C16—H16A	109.5
C2—C3—C4	119.64 (7)	C14—C16—H16B	109.5
C2—C3—H3A	120.2	H16A—C16—H16B	109.5
C4—C3—H3A	120.2	C14—C16—H16C	109.5
C3—C4—C5	120.16 (8)	H16A—C16—H16C	109.5
C3—C4—H4A	119.9	H16B—C16—H16C	109.5
C5—C4—H4A	119.9	O1—C17—C18	121.00 (7)
C4—C5—C6	120.62 (7)	O1—C17—C15	121.00 (7)
C4—C5—H5A	119.7	C18—C17—C15	117.98 (6)
C6—C5—H5A	119.7	C19—C18—C17	122.95 (7)
C5—C6—C1	118.89 (7)	C19—C18—H18A	118.5
C5—C6—C7	120.13 (7)	C17—C18—H18A	118.5
C1—C6—C7	120.97 (7)	C18—C19—C20	126.87 (7)
C15—C7—C8	117.99 (7)	C18—C19—H19A	116.6
C15—C7—C6	121.67 (7)	C20—C19—H19A	116.6
C8—C7—C6	120.34 (6)	C21—C20—C25	118.83 (7)
C9—C8—C13	118.94 (7)	C21—C20—C19	118.42 (7)
C9—C8—C7	123.30 (7)	C25—C20—C19	122.75 (7)
C13—C8—C7	117.72 (7)	C22—C21—C20	120.66 (8)
C10—C9—C8	120.55 (7)	C22—C21—H21A	119.7
C10—C9—H9A	119.7	C20—C21—H21A	119.7
C8—C9—H9A	119.7	C23—C22—C21	120.04 (9)
C9—C10—C11	120.36 (8)	C23—C22—H22A	120.0
C9—C10—H10A	119.8	C21—C22—H22A	120.0
C11—C10—H10A	119.8	C22—C23—C24	119.77 (8)
C12—C11—C10	120.25 (8)	C22—C23—H23A	120.1
C12—C11—H11A	119.9	C24—C23—H23A	120.1
C10—C11—H11A	119.9	C25—C24—C23	120.45 (9)
C11—C12—C13	120.61 (8)	C25—C24—H24A	119.8
C11—C12—H12A	119.7	C23—C24—H24A	119.8
C13—C12—H12A	119.7	C24—C25—C20	120.25 (8)
N1—C13—C12	117.53 (7)	C24—C25—H25A	119.9
N1—C13—C8	123.19 (7)	C20—C25—H25A	119.9
C12—C13—C8	119.28 (7)

C6—C1—C2—C3	1.30 (13)	C7—C8—C13—C12	−177.19 (7)
C1—C2—C3—C4	−0.49 (13)	C13—N1—C14—C15	−1.81 (11)
C2—C3—C4—C5	−0.60 (13)	C13—N1—C14—C16	177.03 (7)
C3—C4—C5—C6	0.90 (13)	C8—C7—C15—C14	−1.49 (11)
C4—C5—C6—C1	−0.10 (12)	C6—C7—C15—C14	178.55 (7)
C4—C5—C6—C7	−179.22 (8)	C8—C7—C15—C17	178.10 (6)
C2—C1—C6—C5	−1.00 (12)	C6—C7—C15—C17	−1.87 (11)
C2—C1—C6—C7	178.11 (7)	N1—C14—C15—C7	3.21 (11)
C5—C6—C7—C15	−101.19 (9)	C16—C14—C15—C7	−175.58 (7)
C1—C6—C7—C15	79.71 (10)	N1—C14—C15—C17	−176.38 (7)
C5—C6—C7—C8	78.85 (10)	C16—C14—C15—C17	4.83 (11)
C1—C6—C7—C8	−100.25 (9)	C7—C15—C17—O1	86.75 (10)
C15—C7—C8—C9	−179.35 (7)	C14—C15—C17—O1	−93.66 (9)
C6—C7—C8—C9	0.62 (11)	C7—C15—C17—C18	−94.95 (9)
C15—C7—C8—C13	−1.28 (10)	C14—C15—C17—C18	84.63 (9)
C6—C7—C8—C13	178.68 (6)	O1—C17—C18—C19	176.95 (8)
C13—C8—C9—C10	−0.51 (12)	C15—C17—C18—C19	−1.35 (11)
C7—C8—C9—C10	177.53 (7)	C17—C18—C19—C20	−178.06 (7)
C8—C9—C10—C11	−0.06 (13)	C18—C19—C20—C21	178.74 (8)
C9—C10—C11—C12	0.17 (13)	C18—C19—C20—C25	−1.61 (13)
C10—C11—C12—C13	0.30 (13)	C25—C20—C21—C22	0.75 (12)
C14—N1—C13—C12	178.75 (7)	C19—C20—C21—C22	−179.58 (8)
C14—N1—C13—C8	−1.20 (11)	C20—C21—C22—C23	−0.58 (14)
C11—C12—C13—N1	179.18 (8)	C21—C22—C23—C24	−0.19 (14)
C11—C12—C13—C8	−0.87 (12)	C22—C23—C24—C25	0.78 (14)
C9—C8—C13—N1	−179.09 (7)	C23—C24—C25—C20	−0.60 (14)
C7—C8—C13—N1	2.76 (11)	C21—C20—C25—C24	−0.16 (12)
C9—C8—C13—C12	0.96 (11)	C19—C20—C25—C24	−179.82 (8)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C20–C25 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg3ⁱ	0.93	2.72	3.5265 (10)	146

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉NO
M_r	349.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.5830 (5), 10.2189 (5), 18.4509 (7)
β (°)	114.147 (2)
V (Å³)	1820.80 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.57 × 0.48 × 0.35

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.957, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	27166, 6509, 5734
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 1.05
No. of reflections	6509
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.17

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

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C20–C25 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg3ⁱ	0.93	2.72	3.5265 (10)	146

Symmetry code: (i) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST–India for funding through the Young Scientist Scheme (Fast Track Proposal).

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Volume 67| Part 4| April 2011| Pages o764-o765

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