1-(6-Chloro-2-methyl-4-phenyl­quinolin-3-yl)-3-(3-methoxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S1600536809052179

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o91-o92

doi:10.1107/S1600536809052179

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1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-(3-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 2 December 2009; accepted 4 December 2009; online 9 December 2009)

In the title compound, C₂₆H₂₀ClNO₂, the quinoline ring system is approximately planar with a maximum deviation of 0.028 (2) Å and forms a dihedral angle of 73.84 (5)° with the phenyl ring. Two neighbouring molecules are arranged into a centrosymmetric dimer through a pair of intermolecular C—H⋯Cl interactions. A pair of intermolecular C—H⋯O hydrogen bonds link two methoxyphenyl groups into another centrosymmetric dimer, generating an R₂²(8) ring motif. The structure is further stabilized by C—H⋯π interactions.

Related literature

For background to 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: Fun et al. (2009 ); Loh et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₆H₂₀ClNO₂
M_r = 413.88
Monoclinic, P 2₁ /c
a = 15.6338 (2) Å
b = 14.0408 (2) Å
c = 10.0321 (1) Å
β = 108.462 (1)°
V = 2088.82 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.33 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.936, T_max = 0.967
51550 measured reflections
6303 independent reflections
5132 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 1.05
6303 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.93	2.40	3.3005 (15)	163
C18—H18A⋯Cl1ⁱⁱ	0.93	2.78	3.6948 (13)	169
C26—H26B⋯O1ⁱⁱⁱ	0.96	2.54	3.4329 (17)	155
C26—H26C⋯Cg1^iv	0.96	2.88	3.8412 (15)	177
C17—H17A⋯Cg2^v	0.93	2.97	3.7592 (14)	144
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+2; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809052179/is2501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052179/is2501Isup2.hkl

checkCIF report

Comment top

The quinolines and their 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 properties (Dimmock et al., 1999). Importantly, chalcones have shown several anticancer activities as inhibitors of cancer cell proliferation, carcinogenesis and metastasis (Zi & Simoneau, 2005).

In the title compound (Fig. 1), the quinoline ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.036 (1) Å at atom C11. This mean plane of quinoline ring forms a dihedral angle of 73.84 (5)° with the phenyl ring (C19–C24). Bond lengths (Allen et al., 1987) and angles are within the normal range and are comparable to closely related structures (Fun et al., 2009; Loh et al., 2009).

In the crystal packing (Fig. 2), two molecules are arranged into a large dimer by a pair of intermolecular C18—H18A···Cl1 interactions. A pair of intermolecular C16—H16A···O2 hydrogen bonds link two methoxyphenyl groups of the neighbouring molecules into another set of dimer, generating an R₂²(8) ring motif (Bernstein et al., 1995). The crystal structure is further stabilized by C—H···π interactions (Table 1), involving C13–C18 (centroid Cg1) and C19–C24 (centroid Cg2) rings.

Related literature top

For background to 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: Fun et al. (2009); Loh et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

To the solution of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (2.95 g, 0.01 M), 3-methoxybenzaldehyde (1.36 g, 0.01 M) and a catalytic amount of KOH in distilled ethanol was added and stirred for about 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 1:1 mixture of ethylacetate and petroleum ether (m.p. 405–407 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 c axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-(3-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₆H₂₀ClNO₂	F(000) = 864
M_r = 413.88	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9882 reflections
a = 15.6338 (2) Å	θ = 2.6–30.3°
b = 14.0408 (2) Å	µ = 0.21 mm⁻¹
c = 10.0321 (1) Å	T = 100 K
β = 108.462 (1)°	Block, colourless
V = 2088.82 (5) Å³	0.33 × 0.25 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6303 independent reflections
Radiation source: fine-focus sealed tube	5132 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 30.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→22
T_min = 0.936, T_max = 0.967	k = −19→19
51550 measured reflections	l = −14→14

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) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0521P)² + 0.7676P] where P = (F_o² + 2F_c²)/3
6303 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₆H₂₀ClNO₂	V = 2088.82 (5) Å³
M_r = 413.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.6338 (2) Å	µ = 0.21 mm⁻¹
b = 14.0408 (2) Å	T = 100 K
c = 10.0321 (1) Å	0.33 × 0.25 × 0.17 mm
β = 108.462 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6303 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5132 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.967	R_int = 0.042
51550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.38 e Å⁻³
6303 reflections	Δρ_min = −0.41 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	0.33917 (2)	0.33164 (3)	0.58574 (4)	0.03525 (10)
O1	0.89366 (6)	0.37834 (7)	0.92588 (10)	0.0275 (2)
O2	0.99503 (6)	0.88427 (6)	1.10271 (9)	0.02503 (19)
N1	0.69406 (7)	0.37222 (7)	0.50187 (10)	0.0202 (2)
C1	0.76533 (8)	0.39716 (8)	0.60758 (12)	0.0194 (2)
C2	0.61229 (8)	0.36683 (8)	0.52489 (12)	0.0186 (2)
C3	0.53676 (9)	0.33562 (9)	0.41238 (13)	0.0232 (2)
H3A	0.5437	0.3220	0.3257	0.028*
C4	0.45373 (9)	0.32536 (9)	0.42991 (13)	0.0245 (3)
H4A	0.4046	0.3044	0.3560	0.029*
C5	0.44385 (8)	0.34703 (10)	0.56185 (13)	0.0230 (2)
C6	0.51471 (8)	0.37833 (9)	0.67275 (12)	0.0208 (2)
H6A	0.5063	0.3926	0.7583	0.025*
C7	0.60098 (8)	0.38886 (8)	0.65627 (11)	0.0175 (2)
C8	0.67867 (8)	0.41709 (8)	0.76909 (11)	0.0170 (2)
C9	0.76028 (7)	0.41997 (8)	0.74412 (12)	0.0174 (2)
C10	0.84595 (8)	0.44340 (9)	0.86210 (12)	0.0195 (2)
C11	0.87075 (8)	0.54318 (9)	0.89574 (13)	0.0217 (2)
H11A	0.9200	0.5564	0.9744	0.026*
C12	0.82630 (8)	0.61647 (9)	0.81913 (13)	0.0204 (2)
H12A	0.7752	0.6020	0.7441	0.024*
C13	0.85050 (7)	0.71727 (9)	0.84237 (12)	0.0191 (2)
C14	0.91311 (8)	0.74920 (9)	0.96894 (12)	0.0196 (2)
H14A	0.9381	0.7067	1.0420	0.024*
C15	0.93706 (8)	0.84453 (9)	0.98366 (12)	0.0198 (2)
C16	0.90136 (8)	0.90856 (9)	0.87281 (13)	0.0226 (2)
H16A	0.9193	0.9720	0.8824	0.027*
C17	0.83926 (8)	0.87700 (9)	0.74883 (13)	0.0227 (2)
H17A	0.8152	0.9195	0.6753	0.027*
C18	0.81280 (8)	0.78194 (9)	0.73403 (13)	0.0214 (2)
H18A	0.7699	0.7614	0.6517	0.026*
C19	0.67020 (7)	0.43834 (9)	0.91020 (11)	0.0177 (2)
C20	0.70262 (9)	0.37333 (9)	1.01947 (13)	0.0233 (2)
H20A	0.7325	0.3187	1.0058	0.028*
C21	0.69045 (9)	0.38998 (10)	1.14923 (13)	0.0269 (3)
H21A	0.7115	0.3461	1.2217	0.032*
C22	0.64704 (9)	0.47190 (10)	1.17049 (13)	0.0260 (3)
H22A	0.6389	0.4829	1.2571	0.031*
C23	0.61572 (9)	0.53749 (10)	1.06250 (13)	0.0257 (3)
H23A	0.5872	0.5928	1.0772	0.031*
C24	0.62681 (8)	0.52078 (9)	0.93238 (12)	0.0221 (2)
H24A	0.6053	0.5646	0.8600	0.027*
C25	0.85421 (9)	0.40069 (11)	0.57958 (14)	0.0269 (3)
H25A	0.8444	0.3918	0.4810	0.040*
H25B	0.8928	0.3511	0.6316	0.040*
H25C	0.8822	0.4614	0.6083	0.040*
C26	1.04176 (9)	0.82146 (10)	1.21483 (13)	0.0257 (3)
H26A	1.0808	0.8579	1.2908	0.038*
H26B	1.0769	0.7769	1.1815	0.038*
H26C	0.9988	0.7875	1.2472	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01933 (15)	0.0596 (2)	0.02639 (17)	−0.01311 (14)	0.00657 (12)	−0.01568 (15)
O1	0.0238 (4)	0.0259 (5)	0.0278 (5)	0.0019 (4)	0.0009 (4)	0.0005 (4)
O2	0.0280 (5)	0.0226 (4)	0.0205 (4)	−0.0053 (3)	0.0019 (4)	−0.0048 (3)
N1	0.0225 (5)	0.0224 (5)	0.0164 (4)	−0.0023 (4)	0.0071 (4)	−0.0014 (4)
C1	0.0212 (5)	0.0193 (5)	0.0189 (5)	−0.0015 (4)	0.0079 (4)	0.0005 (4)
C2	0.0210 (5)	0.0197 (5)	0.0143 (5)	−0.0027 (4)	0.0047 (4)	−0.0011 (4)
C3	0.0262 (6)	0.0283 (6)	0.0141 (5)	−0.0031 (5)	0.0050 (4)	−0.0037 (4)
C4	0.0238 (6)	0.0308 (7)	0.0156 (5)	−0.0056 (5)	0.0015 (4)	−0.0043 (5)
C5	0.0179 (5)	0.0307 (7)	0.0192 (5)	−0.0043 (4)	0.0042 (4)	−0.0045 (5)
C6	0.0197 (5)	0.0263 (6)	0.0157 (5)	−0.0039 (4)	0.0046 (4)	−0.0050 (4)
C7	0.0189 (5)	0.0187 (5)	0.0139 (5)	−0.0022 (4)	0.0038 (4)	−0.0014 (4)
C8	0.0190 (5)	0.0170 (5)	0.0140 (5)	−0.0016 (4)	0.0036 (4)	−0.0008 (4)
C9	0.0177 (5)	0.0165 (5)	0.0172 (5)	−0.0019 (4)	0.0045 (4)	−0.0005 (4)
C10	0.0167 (5)	0.0230 (6)	0.0182 (5)	−0.0017 (4)	0.0046 (4)	−0.0018 (4)
C11	0.0166 (5)	0.0241 (6)	0.0220 (6)	−0.0034 (4)	0.0026 (4)	−0.0044 (5)
C12	0.0169 (5)	0.0238 (6)	0.0202 (5)	−0.0043 (4)	0.0054 (4)	−0.0043 (4)
C13	0.0155 (5)	0.0223 (6)	0.0199 (5)	−0.0024 (4)	0.0060 (4)	−0.0034 (4)
C14	0.0181 (5)	0.0221 (6)	0.0183 (5)	−0.0025 (4)	0.0053 (4)	−0.0018 (4)
C15	0.0174 (5)	0.0231 (6)	0.0189 (5)	−0.0030 (4)	0.0057 (4)	−0.0055 (4)
C16	0.0235 (6)	0.0193 (6)	0.0254 (6)	−0.0012 (4)	0.0083 (5)	−0.0026 (5)
C17	0.0213 (5)	0.0241 (6)	0.0224 (6)	0.0009 (4)	0.0065 (5)	0.0004 (5)
C18	0.0173 (5)	0.0256 (6)	0.0199 (5)	−0.0007 (4)	0.0040 (4)	−0.0033 (4)
C19	0.0157 (5)	0.0229 (6)	0.0134 (5)	−0.0045 (4)	0.0029 (4)	−0.0025 (4)
C20	0.0273 (6)	0.0230 (6)	0.0187 (5)	−0.0007 (5)	0.0059 (5)	0.0003 (4)
C21	0.0320 (7)	0.0307 (7)	0.0169 (5)	−0.0034 (5)	0.0062 (5)	0.0030 (5)
C22	0.0281 (6)	0.0350 (7)	0.0160 (5)	−0.0076 (5)	0.0086 (5)	−0.0051 (5)
C23	0.0262 (6)	0.0297 (7)	0.0217 (6)	0.0005 (5)	0.0084 (5)	−0.0056 (5)
C24	0.0226 (5)	0.0257 (6)	0.0168 (5)	0.0007 (4)	0.0042 (4)	−0.0011 (4)
C25	0.0232 (6)	0.0355 (7)	0.0248 (6)	−0.0028 (5)	0.0115 (5)	−0.0004 (5)
C26	0.0249 (6)	0.0303 (7)	0.0192 (6)	−0.0043 (5)	0.0034 (5)	−0.0038 (5)

Geometric parameters (Å, º) top

Cl1—C5	1.7410 (12)	C13—C14	1.4087 (16)
O1—C10	1.2239 (15)	C14—C15	1.3852 (17)
O2—C15	1.3687 (14)	C14—H14A	0.9300
O2—C26	1.4340 (16)	C15—C16	1.4012 (18)
N1—C1	1.3192 (15)	C16—C17	1.3860 (17)
N1—C2	1.3713 (15)	C16—H16A	0.9300
C1—C9	1.4331 (16)	C17—C18	1.3913 (18)
C1—C25	1.5030 (16)	C17—H17A	0.9300
C2—C7	1.4184 (15)	C18—H18A	0.9300
C2—C3	1.4200 (16)	C19—C20	1.3927 (17)
C3—C4	1.3717 (18)	C19—C24	1.3947 (17)
C3—H3A	0.9300	C20—C21	1.3938 (17)
C4—C5	1.4135 (17)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.386 (2)
C5—C6	1.3703 (16)	C21—H21A	0.9300
C6—C7	1.4176 (16)	C22—C23	1.3876 (19)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.4291 (15)	C23—C24	1.3901 (17)
C8—C9	1.3765 (15)	C23—H23A	0.9300
C8—C19	1.4931 (15)	C24—H24A	0.9300
C9—C10	1.5163 (16)	C25—H25A	0.9600
C10—C11	1.4643 (17)	C25—H25B	0.9600
C11—C12	1.3395 (17)	C25—H25C	0.9600
C11—H11A	0.9300	C26—H26A	0.9600
C12—C13	1.4644 (17)	C26—H26B	0.9600
C12—H12A	0.9300	C26—H26C	0.9600
C13—C18	1.3956 (17)

C15—O2—C26	117.77 (10)	C13—C14—H14A	120.3
C1—N1—C2	118.32 (10)	O2—C15—C14	124.67 (11)
N1—C1—C9	122.65 (10)	O2—C15—C16	114.72 (11)
N1—C1—C25	117.00 (10)	C14—C15—C16	120.61 (11)
C9—C1—C25	120.35 (11)	C17—C16—C15	119.79 (11)
N1—C2—C7	122.80 (10)	C17—C16—H16A	120.1
N1—C2—C3	117.91 (10)	C15—C16—H16A	120.1
C7—C2—C3	119.27 (11)	C16—C17—C18	120.17 (12)
C4—C3—C2	120.87 (11)	C16—C17—H17A	119.9
C4—C3—H3A	119.6	C18—C17—H17A	119.9
C2—C3—H3A	119.6	C17—C18—C13	120.21 (11)
C3—C4—C5	119.07 (11)	C17—C18—H18A	119.9
C3—C4—H4A	120.5	C13—C18—H18A	119.9
C5—C4—H4A	120.5	C20—C19—C24	119.51 (11)
C6—C5—C4	121.97 (11)	C20—C19—C8	119.73 (11)
C6—C5—Cl1	118.79 (9)	C24—C19—C8	120.72 (10)
C4—C5—Cl1	119.24 (9)	C19—C20—C21	120.13 (12)
C5—C6—C7	119.55 (11)	C19—C20—H20A	119.9
C5—C6—H6A	120.2	C21—C20—H20A	119.9
C7—C6—H6A	120.2	C22—C21—C20	120.08 (12)
C6—C7—C2	119.26 (10)	C22—C21—H21A	120.0
C6—C7—C8	122.54 (10)	C20—C21—H21A	120.0
C2—C7—C8	118.14 (10)	C21—C22—C23	119.98 (11)
C9—C8—C7	117.92 (10)	C21—C22—H22A	120.0
C9—C8—C19	122.16 (10)	C23—C22—H22A	120.0
C7—C8—C19	119.86 (10)	C22—C23—C24	120.20 (12)
C8—C9—C1	120.15 (10)	C22—C23—H23A	119.9
C8—C9—C10	120.32 (10)	C24—C23—H23A	119.9
C1—C9—C10	119.48 (10)	C23—C24—C19	120.10 (12)
O1—C10—C11	121.37 (11)	C23—C24—H24A	120.0
O1—C10—C9	119.18 (11)	C19—C24—H24A	120.0
C11—C10—C9	119.44 (10)	C1—C25—H25A	109.5
C12—C11—C10	123.47 (11)	C1—C25—H25B	109.5
C12—C11—H11A	118.3	H25A—C25—H25B	109.5
C10—C11—H11A	118.3	C1—C25—H25C	109.5
C11—C12—C13	126.17 (11)	H25A—C25—H25C	109.5
C11—C12—H12A	116.9	H25B—C25—H25C	109.5
C13—C12—H12A	116.9	O2—C26—H26A	109.5
C18—C13—C14	119.77 (11)	O2—C26—H26B	109.5
C18—C13—C12	118.73 (11)	H26A—C26—H26B	109.5
C14—C13—C12	121.45 (11)	O2—C26—H26C	109.5
C15—C14—C13	119.40 (11)	H26A—C26—H26C	109.5
C15—C14—H14A	120.3	H26B—C26—H26C	109.5

C2—N1—C1—C9	−0.89 (17)	C8—C9—C10—C11	−84.74 (14)
C2—N1—C1—C25	178.93 (11)	C1—C9—C10—C11	97.70 (13)
C1—N1—C2—C7	1.39 (17)	O1—C10—C11—C12	172.29 (12)
C1—N1—C2—C3	−177.10 (11)	C9—C10—C11—C12	−6.60 (18)
N1—C2—C3—C4	177.64 (12)	C10—C11—C12—C13	−176.37 (11)
C7—C2—C3—C4	−0.90 (19)	C11—C12—C13—C18	163.13 (12)
C2—C3—C4—C5	0.5 (2)	C11—C12—C13—C14	−14.47 (18)
C3—C4—C5—C6	0.2 (2)	C18—C13—C14—C15	−0.56 (17)
C3—C4—C5—Cl1	−178.61 (10)	C12—C13—C14—C15	177.02 (11)
C4—C5—C6—C7	−0.5 (2)	C26—O2—C15—C14	7.01 (17)
Cl1—C5—C6—C7	178.35 (10)	C26—O2—C15—C16	−173.30 (11)
C5—C6—C7—C2	0.07 (18)	C13—C14—C15—O2	178.05 (11)
C5—C6—C7—C8	−177.16 (12)	C13—C14—C15—C16	−1.62 (17)
N1—C2—C7—C6	−177.85 (11)	O2—C15—C16—C17	−177.59 (11)
C3—C2—C7—C6	0.61 (17)	C14—C15—C16—C17	2.11 (18)
N1—C2—C7—C8	−0.50 (17)	C15—C16—C17—C18	−0.38 (18)
C3—C2—C7—C8	177.97 (11)	C16—C17—C18—C13	−1.81 (18)
C6—C7—C8—C9	176.38 (11)	C14—C13—C18—C17	2.28 (17)
C2—C7—C8—C9	−0.88 (16)	C12—C13—C18—C17	−175.37 (11)
C6—C7—C8—C19	−1.07 (17)	C9—C8—C19—C20	−71.87 (15)
C2—C7—C8—C19	−178.33 (10)	C7—C8—C19—C20	105.47 (13)
C7—C8—C9—C1	1.36 (16)	C9—C8—C19—C24	110.80 (13)
C19—C8—C9—C1	178.75 (11)	C7—C8—C19—C24	−71.86 (15)
C7—C8—C9—C10	−176.19 (10)	C24—C19—C20—C21	1.01 (18)
C19—C8—C9—C10	1.20 (17)	C8—C19—C20—C21	−176.35 (11)
N1—C1—C9—C8	−0.50 (18)	C19—C20—C21—C22	−0.8 (2)
C25—C1—C9—C8	179.69 (11)	C20—C21—C22—C23	0.0 (2)
N1—C1—C9—C10	177.07 (11)	C21—C22—C23—C24	0.7 (2)
C25—C1—C9—C10	−2.74 (17)	C22—C23—C24—C19	−0.54 (19)
C8—C9—C10—O1	96.34 (14)	C20—C19—C24—C23	−0.33 (18)
C1—C9—C10—O1	−81.22 (15)	C8—C19—C24—C23	177.01 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, resepctively.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.40	3.3005 (15)	163
C18—H18A···Cl1ⁱⁱ	0.93	2.78	3.6948 (13)	169
C26—H26B···O1ⁱⁱⁱ	0.96	2.54	3.4329 (17)	155
C26—H26C···Cg1^iv	0.96	2.88	3.8412 (15)	177
C17—H17A···Cg2^v	0.93	2.97	3.7592 (14)	144

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀ClNO₂
M_r	413.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.6338 (2), 14.0408 (2), 10.0321 (1)
β (°)	108.462 (1)
V (Å³)	2088.82 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.33 × 0.25 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.936, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	51550, 6303, 5132
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.05
No. of reflections	6303
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.41

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, resepctively.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.40	3.3005 (15)	163
C18—H18A···Cl1ⁱⁱ	0.93	2.78	3.6948 (13)	169
C26—H26B···O1ⁱⁱⁱ	0.96	2.54	3.4329 (17)	155
C26—H26C···Cg1^iv	0.96	2.88	3.8412 (15)	177
C17—H17A···Cg2^v	0.93	2.97	3.7592 (14)	144

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

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

WSL and HKF thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of the post of Assistant Research Officer under the Research University Golden Goose Grant (1001/PFIZIK/811012). VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y.-L., Fang, K.-C., Sheu, J.-Y., Hsu, S.-L. & Tzeng, C.-C. (2001). J. Med. Chem. 44, 2374–2377. Web of Science CrossRef PubMed CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. pp. 1125–1149. Google Scholar
Fun, H.-K., Loh, W.-S., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2009). Acta Cryst. E65, o2688–o2689. Web of Science CrossRef IUCr Journals Google Scholar
Kalluraya, B. & Sreenivasa, S. (1998). Farmaco, 53, 399–404. Web of Science CrossRef CAS PubMed Google Scholar
Loh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2009). Acta Cryst. E65, o3144–o3145. Web of Science CSD CrossRef IUCr Journals Google Scholar
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324–326. CrossRef CAS PubMed Web of Science Google Scholar
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605–608. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zi, X. & Simoneau, A. R. (2005). Cancer Res. 65, 3479–3486. Web of Science CrossRef PubMed CAS Google Scholar

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