(E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol­yl)-3-(2-methoxy­phen­yl)prop-2-en-1-one

Loh, W.-S.; Fun, H.-K.; Sarveswari, S.; Vijayakumar, V.; Reddy, B.P.

doi:10.1107/S1600536810000784

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages o353-o354

https://doi.org/10.1107/S1600536810000784

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(E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinolyl)-3-(2-methoxyphenyl)prop-2-en-1-one

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ S. Sarveswari,^b V. Vijayakumar ^b and B. Palakshi Reddy ^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 4 January 2010; accepted 7 January 2010; online 13 January 2010)

In the title compound, C₂₆H₂₀ClNO₂, the quinoline ring system and the methoxyphenyl ring form dihedral angles of 69.97 (6) and 22.10 (10)°, respectively, with the propenone linkage. The 4-phenyl ring substituent on the quinoline ring system is oriented at a dihedral angle of 66.47 (3)°. In the crystal, molecules exist as C—H⋯O hydrogen-bonded dimers. The structure is further stabilized by C—H⋯π interactions.

Related literature

For background details and the biological activity of quinolines, see: Michael (1997 ); Markees et al. (1970 ); Kalluraya & Sreenivasa (1998 ); Chen et al. (2001 ). For the biological activity of chalcones, see: Dimmock et al. (1999 ); Zi & Simoneau (2005 ). For related structures, see: Loh et al. (2009a ,b ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₆H₂₀ClNO₂
M_r = 413.88
Monoclinic, C 2/c
a = 15.1154 (2) Å
b = 15.4655 (2) Å
c = 17.2400 (2) Å
β = 104.418 (1)°
V = 3903.22 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.39 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.919, T_max = 0.960
30753 measured reflections
8197 independent reflections
5864 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.136
S = 1.06
8197 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and N1/C1/C2/C7–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.93	2.59	3.2963 (16)	133
C17—H17A⋯Cg1ⁱⁱ	0.93	2.96	3.6617 (14)	134
C20—H20A⋯Cg2ⁱⁱ	0.93	2.85	3.6353 (14)	143
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[x, -y-1, z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810000784/ci5015sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000784/ci5015Isup2.hkl

checkCIF report

Comment top

Quinoline and its derivatives are very important compounds because of their wide occurrence in natural products (Michael, 1997) and biologically active compounds (Markees et al., 1970). A large variety of quinolines have interesting physiological activities and found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Kalluraya & Sreenivasa, 1998; Chen et al., 2001). The chalcones are open chain flavonoids, possessing a variety of biological activities, including antioxidant, anti-inflammation, antimicrobial, antiprotozoal, antiulcer, as well as other activities (Dimmock et al., 1999). More importantly, chalcones have shown several anticancer activities as inhibitors of cancer cell proliferation, carcinogenesis and metastasis (Zi & Simoneau, 2005).

In the molecule of the title compound (Fig. 1), the quinoline ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.065 (1) Å for atom C9. The mean plane of the quinoline ring system forms a dihedral angle of 66.47 (3)° with the C10-C15 phenyl ring. The C1–C9/N1 and C19-C24 planes form dihedral angles of 69.97 (6) and 22.10 (10)°, respectively, with the O1/C16-C18 plane. Bond lengths (Allen et al., 1987) and angles are within the normal range and are comparable to closely related structures (Loh et al., 2009a; Loh et al., 2009b).

In the crystal (Fig. 2), pairs of neighbouring molecules are arranged into dimers by pairs of intermolecular C12—H12A···O1 hydrogen bonds. The crystal structure is further stabilized by C—H···π interactions (Table 1), involving C2–C7 (centroid Cg1) and N1/C1/C2/C7-C9 (centroid Cg2) rings.

Related literature top

For background details and the biological activity of quinolines, see: Michael (1997); Markees et al. (1970); Kalluraya & Sreenivasa (1998); Chen et al. (2001). For the biological activity of chalcones, see: Dimmock et al. (1999); Zi & Simoneau (2005). For related structures, see: Loh et al. (2009a,b). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (2.95 g, 0.01 mol), 2-methoxybenzaldehyde (1.36 g, 0.01 mol) and a catalytic amount of KOH in distilled ethanol was stirred for 12 h. The resulting mixture was concentrated to remove the ethanol and then poured onto ice and neutralized with diluted acetic acid. The resultant solid was filtered, dried and purified by column chromatography using a 1:1 mixture of ethyl acetate and petroleum ether (m.p. 403–405 K, yield: 68%).

Structure description top

For background details and the biological activity of quinolines, see: Michael (1997); Markees et al. (1970); Kalluraya & Sreenivasa (1998); Chen et al. (2001). For the biological activity of chalcones, see: Dimmock et al. (1999); Zi & Simoneau (2005). For related structures, see: Loh et al. (2009a,b). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 approximately along the b axis, showing the dimers. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinolyl)-3-(2-methoxyphenyl)prop- 2-en-1-one top

Crystal data top

C₂₆H₂₀ClNO₂	F(000) = 1728
M_r = 413.88	D_x = 1.409 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7486 reflections
a = 15.1154 (2) Å	θ = 2.4–31.5°
b = 15.4655 (2) Å	µ = 0.22 mm⁻¹
c = 17.2400 (2) Å	T = 100 K
β = 104.418 (1)°	Block, yellow
V = 3903.22 (9) Å³	0.39 × 0.25 × 0.19 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8197 independent reflections
Radiation source: fine-focus sealed tube	5864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 34.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→24
T_min = 0.919, T_max = 0.960	k = −24→19
30753 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0625P)² + 0.7227P] where P = (F_o² + 2F_c²)/3
8197 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₆H₂₀ClNO₂	V = 3903.22 (9) Å³
M_r = 413.88	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.1154 (2) Å	µ = 0.22 mm⁻¹
b = 15.4655 (2) Å	T = 100 K
c = 17.2400 (2) Å	0.39 × 0.25 × 0.19 mm
β = 104.418 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8197 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5864 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.960	R_int = 0.039
30753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	Δρ_max = 0.54 e Å⁻³
8197 reflections	Δρ_min = −0.31 e Å⁻³
273 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
Cl1	0.02177 (2)	1.01758 (2)	0.635395 (19)	0.01901 (8)
O1	0.27571 (6)	0.58953 (6)	0.86651 (5)	0.0176 (2)
O2	−0.04599 (6)	0.49228 (6)	0.58651 (5)	0.0182 (2)
N1	0.23373 (7)	0.70354 (7)	0.61280 (6)	0.0132 (2)
C1	0.24441 (8)	0.64331 (8)	0.66867 (7)	0.0119 (2)
C2	0.18686 (8)	0.77723 (8)	0.62237 (7)	0.0118 (2)
C3	0.17164 (9)	0.83936 (8)	0.55976 (7)	0.0140 (2)
H3A	0.1948	0.8299	0.5153	0.017*
C4	0.12304 (9)	0.91308 (8)	0.56457 (7)	0.0147 (2)
H4A	0.1130	0.9538	0.5236	0.018*
C5	0.08838 (8)	0.92650 (8)	0.63233 (7)	0.0137 (2)
C6	0.10437 (8)	0.87006 (8)	0.69522 (7)	0.0130 (2)
H6A	0.0826	0.8818	0.7400	0.016*
C7	0.15466 (8)	0.79326 (8)	0.69143 (7)	0.0114 (2)
C8	0.17037 (8)	0.72900 (8)	0.75300 (7)	0.0113 (2)
C9	0.21100 (8)	0.65250 (8)	0.73916 (7)	0.0117 (2)
C10	0.14444 (8)	0.74686 (8)	0.82932 (7)	0.0126 (2)
C11	0.18819 (9)	0.81414 (9)	0.87804 (8)	0.0184 (3)
H11A	0.2323	0.8468	0.8622	0.022*
C12	0.16655 (11)	0.83282 (10)	0.94971 (8)	0.0234 (3)
H12A	0.1966	0.8774	0.9819	0.028*
C13	0.10036 (10)	0.78525 (10)	0.97343 (8)	0.0236 (3)
H13A	0.0853	0.7983	1.0212	0.028*
C14	0.05658 (9)	0.71812 (10)	0.92586 (8)	0.0213 (3)
H14A	0.0122	0.6860	0.9419	0.026*
C15	0.07867 (9)	0.69836 (9)	0.85395 (7)	0.0166 (2)
H15A	0.0495	0.6528	0.8225	0.020*
C16	0.22442 (8)	0.57996 (8)	0.79974 (7)	0.0125 (2)
C17	0.17554 (9)	0.49843 (8)	0.77583 (7)	0.0144 (2)
H17A	0.1908	0.4509	0.8095	0.017*
C18	0.10990 (9)	0.48907 (8)	0.70786 (7)	0.0137 (2)
H18A	0.0929	0.5384	0.6769	0.016*
C19	0.06258 (8)	0.40889 (8)	0.67781 (7)	0.0135 (2)
C20	0.09598 (9)	0.32817 (8)	0.70747 (8)	0.0161 (2)
H20A	0.1493	0.3253	0.7484	0.019*
C21	0.05186 (9)	0.25228 (9)	0.67757 (8)	0.0186 (3)
H21A	0.0758	0.1990	0.6974	0.022*
C22	−0.02865 (9)	0.25684 (9)	0.61751 (8)	0.0193 (3)
H22A	−0.0595	0.2062	0.5983	0.023*
C23	−0.06371 (9)	0.33563 (9)	0.58583 (8)	0.0171 (3)
H23A	−0.1175	0.3377	0.5454	0.021*
C24	−0.01789 (9)	0.41163 (8)	0.61490 (7)	0.0148 (2)
C25	0.29908 (9)	0.56529 (8)	0.65696 (8)	0.0170 (2)
H25A	0.3273	0.5758	0.6137	0.026*
H25B	0.2594	0.5160	0.6445	0.026*
H25C	0.3454	0.5542	0.7052	0.026*
C26	−0.12419 (10)	0.49727 (10)	0.51992 (8)	0.0213 (3)
H26A	−0.1348	0.5564	0.5034	0.032*
H26B	−0.1767	0.4752	0.5353	0.032*
H26C	−0.1136	0.4636	0.4763	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01956 (16)	0.01561 (16)	0.02069 (15)	0.00653 (12)	0.00279 (12)	0.00098 (11)
O1	0.0204 (5)	0.0172 (5)	0.0129 (4)	0.0012 (4)	−0.0004 (3)	−0.0009 (3)
O2	0.0176 (5)	0.0162 (5)	0.0172 (4)	0.0006 (4)	−0.0022 (4)	0.0005 (3)
N1	0.0144 (5)	0.0130 (5)	0.0124 (4)	0.0001 (4)	0.0039 (4)	−0.0009 (4)
C1	0.0120 (5)	0.0122 (6)	0.0117 (5)	−0.0003 (4)	0.0030 (4)	−0.0017 (4)
C2	0.0109 (5)	0.0123 (5)	0.0119 (5)	−0.0004 (4)	0.0026 (4)	−0.0004 (4)
C3	0.0148 (6)	0.0156 (6)	0.0112 (5)	−0.0014 (4)	0.0025 (4)	0.0004 (4)
C4	0.0158 (6)	0.0147 (6)	0.0125 (5)	−0.0006 (5)	0.0013 (4)	0.0014 (4)
C5	0.0130 (6)	0.0110 (5)	0.0155 (5)	0.0003 (4)	0.0008 (4)	−0.0005 (4)
C6	0.0139 (5)	0.0135 (6)	0.0118 (5)	0.0002 (4)	0.0034 (4)	−0.0010 (4)
C7	0.0108 (5)	0.0120 (6)	0.0111 (5)	−0.0003 (4)	0.0021 (4)	−0.0001 (4)
C8	0.0113 (5)	0.0121 (5)	0.0106 (5)	−0.0017 (4)	0.0028 (4)	−0.0001 (4)
C9	0.0120 (5)	0.0116 (5)	0.0111 (5)	−0.0007 (4)	0.0022 (4)	−0.0005 (4)
C10	0.0152 (6)	0.0121 (5)	0.0107 (5)	0.0031 (4)	0.0038 (4)	0.0011 (4)
C11	0.0228 (7)	0.0180 (6)	0.0154 (5)	−0.0025 (5)	0.0069 (5)	−0.0022 (5)
C12	0.0329 (8)	0.0227 (7)	0.0153 (6)	0.0010 (6)	0.0073 (6)	−0.0046 (5)
C13	0.0293 (8)	0.0305 (8)	0.0135 (5)	0.0091 (6)	0.0103 (5)	0.0023 (5)
C14	0.0206 (7)	0.0282 (8)	0.0186 (6)	0.0042 (6)	0.0116 (5)	0.0059 (5)
C15	0.0170 (6)	0.0179 (6)	0.0157 (5)	0.0009 (5)	0.0054 (5)	0.0019 (5)
C16	0.0132 (5)	0.0132 (6)	0.0116 (5)	0.0015 (4)	0.0042 (4)	−0.0001 (4)
C17	0.0180 (6)	0.0119 (6)	0.0139 (5)	0.0003 (4)	0.0052 (5)	0.0012 (4)
C18	0.0152 (6)	0.0129 (6)	0.0136 (5)	−0.0001 (4)	0.0047 (4)	−0.0003 (4)
C19	0.0126 (5)	0.0155 (6)	0.0132 (5)	−0.0009 (4)	0.0047 (4)	−0.0006 (4)
C20	0.0140 (6)	0.0166 (6)	0.0170 (6)	0.0000 (5)	0.0026 (5)	−0.0017 (5)
C21	0.0200 (6)	0.0130 (6)	0.0218 (6)	0.0005 (5)	0.0036 (5)	−0.0012 (5)
C22	0.0215 (7)	0.0163 (6)	0.0201 (6)	−0.0037 (5)	0.0052 (5)	−0.0041 (5)
C23	0.0156 (6)	0.0204 (6)	0.0150 (5)	−0.0024 (5)	0.0032 (5)	−0.0031 (5)
C24	0.0144 (6)	0.0167 (6)	0.0140 (5)	0.0004 (5)	0.0048 (4)	−0.0016 (4)
C25	0.0193 (6)	0.0160 (6)	0.0168 (6)	0.0046 (5)	0.0065 (5)	0.0005 (5)
C26	0.0179 (7)	0.0245 (7)	0.0178 (6)	0.0014 (5)	−0.0025 (5)	0.0019 (5)

Geometric parameters (Å, º) top

Cl1—C5	1.7397 (13)	C13—C14	1.385 (2)
O1—C16	1.2262 (14)	C13—H13A	0.93
O2—C24	1.3683 (15)	C14—C15	1.3956 (17)
O2—C26	1.4302 (16)	C14—H14A	0.93
N1—C1	1.3207 (15)	C15—H15A	0.93
N1—C2	1.3733 (15)	C16—C17	1.4678 (18)
C1—C9	1.4344 (16)	C17—C18	1.3414 (17)
C1—C25	1.5042 (17)	C17—H17A	0.93
C2—C7	1.4158 (16)	C18—C19	1.4606 (18)
C2—C3	1.4205 (17)	C18—H18A	0.93
C3—C4	1.3700 (18)	C19—C20	1.3951 (18)
C3—H3A	0.93	C19—C24	1.4144 (18)
C4—C5	1.4098 (17)	C20—C21	1.3845 (18)
C4—H4A	0.93	C20—H20A	0.93
C5—C6	1.3657 (16)	C21—C22	1.3895 (18)
C6—C7	1.4204 (17)	C21—H21A	0.93
C6—H6A	0.93	C22—C23	1.3855 (19)
C7—C8	1.4302 (16)	C22—H22A	0.93
C8—C9	1.3808 (17)	C23—C24	1.3926 (18)
C8—C10	1.4893 (16)	C23—H23A	0.93
C9—C16	1.5116 (17)	C25—H25A	0.96
C10—C15	1.3934 (18)	C25—H25B	0.96
C10—C11	1.3960 (18)	C25—H25C	0.96
C11—C12	1.3851 (18)	C26—H26A	0.96
C11—H11A	0.93	C26—H26B	0.96
C12—C13	1.383 (2)	C26—H26C	0.96
C12—H12A	0.93

C24—O2—C26	117.21 (10)	C15—C14—H14A	119.8
C1—N1—C2	118.08 (10)	C10—C15—C14	119.97 (12)
N1—C1—C9	122.90 (11)	C10—C15—H15A	120.0
N1—C1—C25	116.07 (10)	C14—C15—H15A	120.0
C9—C1—C25	120.94 (10)	O1—C16—C17	121.58 (11)
N1—C2—C7	122.82 (11)	O1—C16—C9	120.26 (11)
N1—C2—C3	117.44 (10)	C17—C16—C9	118.16 (10)
C7—C2—C3	119.74 (11)	C18—C17—C16	123.30 (11)
C4—C3—C2	120.32 (11)	C18—C17—H17A	118.3
C4—C3—H3A	119.8	C16—C17—H17A	118.3
C2—C3—H3A	119.8	C17—C18—C19	126.29 (12)
C3—C4—C5	119.23 (11)	C17—C18—H18A	116.9
C3—C4—H4A	120.4	C19—C18—H18A	116.9
C5—C4—H4A	120.4	C20—C19—C24	118.13 (11)
C6—C5—C4	122.34 (11)	C20—C19—C18	121.94 (11)
C6—C5—Cl1	118.87 (10)	C24—C19—C18	119.89 (11)
C4—C5—Cl1	118.79 (9)	C21—C20—C19	121.69 (12)
C5—C6—C7	119.27 (11)	C21—C20—H20A	119.2
C5—C6—H6A	120.4	C19—C20—H20A	119.2
C7—C6—H6A	120.4	C20—C21—C22	119.06 (12)
C2—C7—C6	119.02 (10)	C20—C21—H21A	120.5
C2—C7—C8	118.30 (11)	C22—C21—H21A	120.5
C6—C7—C8	122.60 (11)	C23—C22—C21	121.09 (12)
C9—C8—C7	117.77 (10)	C23—C22—H22A	119.5
C9—C8—C10	122.53 (10)	C21—C22—H22A	119.5
C7—C8—C10	119.68 (11)	C22—C23—C24	119.56 (12)
C8—C9—C1	119.79 (10)	C22—C23—H23A	120.2
C8—C9—C16	120.36 (10)	C24—C23—H23A	120.2
C1—C9—C16	119.79 (10)	O2—C24—C23	123.95 (11)
C15—C10—C11	119.01 (11)	O2—C24—C19	115.63 (11)
C15—C10—C8	122.28 (11)	C23—C24—C19	120.42 (12)
C11—C10—C8	118.71 (11)	C1—C25—H25A	109.5
C12—C11—C10	120.69 (13)	C1—C25—H25B	109.5
C12—C11—H11A	119.7	H25A—C25—H25B	109.5
C10—C11—H11A	119.7	C1—C25—H25C	109.5
C13—C12—C11	120.11 (13)	H25A—C25—H25C	109.5
C13—C12—H12A	119.9	H25B—C25—H25C	109.5
C11—C12—H12A	119.9	O2—C26—H26A	109.5
C12—C13—C14	119.85 (12)	O2—C26—H26B	109.5
C12—C13—H13A	120.1	H26A—C26—H26B	109.5
C14—C13—H13A	120.1	O2—C26—H26C	109.5
C13—C14—C15	120.36 (13)	H26A—C26—H26C	109.5
C13—C14—H14A	119.8	H26B—C26—H26C	109.5

C2—N1—C1—C9	−1.36 (17)	C7—C8—C10—C11	−63.24 (16)
C2—N1—C1—C25	−177.88 (10)	C15—C10—C11—C12	−0.21 (19)
C1—N1—C2—C7	3.89 (17)	C8—C10—C11—C12	−179.71 (12)
C1—N1—C2—C3	−176.69 (11)	C10—C11—C12—C13	−0.6 (2)
N1—C2—C3—C4	178.10 (11)	C11—C12—C13—C14	0.9 (2)
C7—C2—C3—C4	−2.46 (18)	C12—C13—C14—C15	−0.2 (2)
C2—C3—C4—C5	0.00 (18)	C11—C10—C15—C14	0.85 (19)
C3—C4—C5—C6	2.54 (19)	C8—C10—C15—C14	−179.67 (11)
C3—C4—C5—Cl1	−176.70 (10)	C13—C14—C15—C10	−0.6 (2)
C4—C5—C6—C7	−2.50 (18)	C8—C9—C16—O1	−64.94 (16)
Cl1—C5—C6—C7	176.75 (9)	C1—C9—C16—O1	112.20 (13)
N1—C2—C7—C6	−178.11 (11)	C8—C9—C16—C17	115.85 (13)
C3—C2—C7—C6	2.48 (17)	C1—C9—C16—C17	−67.02 (15)
N1—C2—C7—C8	−1.18 (17)	O1—C16—C17—C18	170.75 (12)
C3—C2—C7—C8	179.42 (11)	C9—C16—C17—C18	−10.04 (18)
C5—C6—C7—C2	−0.04 (17)	C16—C17—C18—C19	175.84 (12)
C5—C6—C7—C8	−176.84 (11)	C17—C18—C19—C20	−15.8 (2)
C2—C7—C8—C9	−4.05 (17)	C17—C18—C19—C24	166.47 (12)
C6—C7—C8—C9	172.77 (11)	C24—C19—C20—C21	−0.80 (18)
C2—C7—C8—C10	174.87 (11)	C18—C19—C20—C21	−178.61 (12)
C6—C7—C8—C10	−8.31 (17)	C19—C20—C21—C22	−1.21 (19)
C7—C8—C9—C1	6.47 (17)	C20—C21—C22—C23	1.8 (2)
C10—C8—C9—C1	−172.42 (11)	C21—C22—C23—C24	−0.39 (19)
C7—C8—C9—C16	−176.40 (10)	C26—O2—C24—C23	−3.77 (18)
C10—C8—C9—C16	4.71 (18)	C26—O2—C24—C19	176.59 (11)
N1—C1—C9—C8	−3.94 (18)	C22—C23—C24—O2	178.69 (12)
C25—C1—C9—C8	172.42 (11)	C22—C23—C24—C19	−1.69 (19)
N1—C1—C9—C16	178.91 (11)	C20—C19—C24—O2	−178.09 (11)
C25—C1—C9—C16	−4.73 (17)	C18—C19—C24—O2	−0.24 (17)
C9—C8—C10—C15	−63.86 (17)	C20—C19—C24—C23	2.26 (18)
C7—C8—C10—C15	117.28 (13)	C18—C19—C24—C23	−179.89 (11)
C9—C8—C10—C11	115.63 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.93	2.59	3.2963 (16)	133
C17—H17A···Cg1ⁱⁱ	0.93	2.96	3.6617 (14)	134
C20—H20A···Cg2ⁱⁱ	0.93	2.85	3.6353 (14)	143

Symmetry codes: (i) −x+1/2, −y+3/2, −z+2; (ii) x, −y−1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀ClNO₂
M_r	413.88
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	15.1154 (2), 15.4655 (2), 17.2400 (2)
β (°)	104.418 (1)
V (Å³)	3903.22 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.39 × 0.25 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.919, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	30753, 8197, 5864
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.796

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.136, 1.06
No. of reflections	8197
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.31

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.93	2.59	3.2963 (16)	133
C17—H17A···Cg1ⁱⁱ	0.93	2.96	3.6617 (14)	134
C20—H20A···Cg2ⁱⁱ	0.93	2.85	3.6353 (14)	143

Symmetry codes: (i) −x+1/2, −y+3/2, −z+2; (ii) x, −y−1, z+1/2.

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 Golden Goose grant No. 1001/PFIZIK/811012. WSL thanks the Malaysian government and USM for the award of the post of Assistant Research Officer under Research University Golden Goose grant No. 1001/PFIZIK/811012. VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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