(2E)-1-(6-Chloro-2-methyl-4-phenyl­quinolin-3-yl)-3-phenyl­prop-2-en-1-one

Viji, A.J.; Sarveswari, S.; Vijayakumar, V.; Tan, K.W.; Tiekink, E.R.T.

doi:10.1107/S160053681002386X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1780

doi:10.1107/S160053681002386X

Open

access

(2E)-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-phenylprop-2-en-1-one

A. J. Viji,^a S. Sarveswari,^a V. Vijayakumar,^a ‡ Kong Wai Tan ^b and Edward R. T. Tiekink ^b ^*

^aOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 June 2010; accepted 19 June 2010; online 26 June 2010)

In the title compound, C₂₅H₁₈ClNO, the conformation about the C=C double bond is E. Significant twists are evident in the molecule, with the benzene ring forming a dihedral angle of 53.92 (11)° with the quinolinyl residue. Further, the chalcone residue is approximately perpendicular to the quinolinyl residue [C_q—C_q—C_c—O_c torsion angle = −104.5 (3)°, where q = quinolinyl and c = chalcone]. In the crystal, the presence of C—H⋯O and C—H⋯π interactions leads to supramolecular layers lying parallel to ( $[\overline{1}]$ 02).

Related literature

For the biological activity of quinoline derivatives, see: Campbell et al. (1998 ). For the biological activity of chalcone derivatives, see: Chen et al. (2001 ); Zi & Simoneau (2005 ). For a related structure, see: Prasath et al. (2010 ).

Experimental

Crystal data

C₂₅H₁₈ClNO
M_r = 383.85
Monoclinic, P 2₁ /c
a = 9.9250 (9) Å
b = 11.1001 (9) Å
c = 17.4651 (15) Å
β = 97.250 (1)°
V = 1908.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.46 × 0.30 × 0.26 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.536, T_max = 1.000
16152 measured reflections
3948 independent reflections
3030 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.188
S = 1.09
3948 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C10–C12,C17,C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95	2.48	3.315 (3)	146
C21—H21⋯Cg1ⁱⁱ	0.95	2.71	3.459 (3)	137
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002386X/hb5510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002386X/hb5510Isup2.hkl

checkCIF report

Comment top

Both quinolines (Campbell et al., 1998) and open chain flavonoids, i.e. chalcones (Chen et al., 2001; Zi & Simoneau, 2005), are known to possess a wide range of biological activities. Herein, in continuation of previous studies (Prasath et al., 2010), we describe the crystal structure of a molecule containing both quinoline and chalcone residues, namely, the title compound, (I).

In (I), Fig. 1, the quinolinyl residue is planar [r.m.s. = 0.041 Å] with both the benzene ring and chalcone residue being twisted out of the plane. The dihedral angle formed between the quinolinyl and benzene (C20–C25) rings is 53.92 (11) °. In the case of the chalcone residue, the twist is best illustrated by the O1–C9–C10–C11 torsion angle of -104.5 (3) °. There are also twists within the chalcone residues as exemplified by the C7–C8–C9–O1 and C7–C8–C9–C10 torsion angles of -163.7 (3) and 14.7 (4) °, respectively. The conformation about the C7═C8 bond [1.340 (4) Å] is E.

Supramolecular layers parallel to (1 0 2) are evident in the crystal structure. These, Fig. 2 and Table 1, are stabilized by C–H···O contacts and C–H···π interactions where the π-system is the NC₅ ring of the quinolinyl residue.

Related literature top

For the biological activity of quinoline derivatives, see: Campbell et al. (1998). For the biological activity of chalcone derivatives, see: Chen et al. (2001); Zi & Simoneau (2005). For a related structure, see: Prasath et al. (2010).

Experimental top

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (0.01 M), benzaldehyde (0.0 1M) and a catalytic amount of KOH in distilled ethanol (50 ml) was stirred for about 12 h. The resulting mixture was concentrated to remove ethanol, poured on to ice and neutralized with dilute acetic acid. The solid that formed was filtered, dried, purified by column chromatography using a 1:1 mixture of ethyl acetate and petroleum ether, and recrystallized using ethyl acetate to produce colourless blocks of (I); Yield: 65% and m.pt: 400 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular array in (I) highlighting the C–H···O and C–H···π interactions as orange and purple dashed lines, respectively.

(2E)-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-phenylprop-2-en-1-one top

Crystal data top

C₂₅H₁₈ClNO	F(000) = 800
M_r = 383.85	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4382 reflections
a = 9.9250 (9) Å	θ = 2.2–28.1°
b = 11.1001 (9) Å	µ = 0.22 mm⁻¹
c = 17.4651 (15) Å	T = 100 K
β = 97.250 (1)°	Block, colourless
V = 1908.7 (3) Å³	0.46 × 0.30 × 0.26 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3948 independent reflections
Radiation source: fine-focus sealed tube	3030 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.536, T_max = 1.000	k = −13→13
16152 measured reflections	l = −21→21

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0925P)² + 1.6015P] where P = (F_o² + 2F_c²)/3
3948 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₅H₁₈ClNO	V = 1908.7 (3) Å³
M_r = 383.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9250 (9) Å	µ = 0.22 mm⁻¹
b = 11.1001 (9) Å	T = 100 K
c = 17.4651 (15) Å	0.46 × 0.30 × 0.26 mm
β = 97.250 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3948 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3030 reflections with I > 2σ(I)
T_min = 0.536, T_max = 1.000	R_int = 0.079
16152 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.09	Δρ_max = 0.85 e Å⁻³
3948 reflections	Δρ_min = −0.49 e Å⁻³
254 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.10119 (8)	−0.00729 (6)	0.39598 (4)	0.0310 (2)
O1	0.13396 (19)	0.68284 (16)	0.58922 (12)	0.0270 (5)
N1	0.3459 (2)	0.4751 (2)	0.42881 (14)	0.0225 (5)
C1	0.4920 (3)	0.5159 (2)	0.77131 (17)	0.0218 (6)
C2	0.4665 (3)	0.5785 (2)	0.83726 (17)	0.0254 (6)
H2	0.3927	0.6335	0.8343	0.031*
C3	0.5471 (3)	0.5616 (2)	0.90671 (18)	0.0275 (6)
H3	0.5278	0.6040	0.9513	0.033*
C4	0.6565 (3)	0.4825 (2)	0.91160 (18)	0.0284 (7)
H4	0.7118	0.4706	0.9595	0.034*
C5	0.6847 (3)	0.4212 (2)	0.84662 (18)	0.0291 (7)
H5	0.7599	0.3677	0.8497	0.035*
C6	0.6033 (3)	0.4376 (2)	0.77700 (17)	0.0254 (6)
H6	0.6233	0.3952	0.7325	0.030*
C7	0.4062 (3)	0.5249 (2)	0.69742 (17)	0.0219 (6)
H7	0.4326	0.4781	0.6562	0.026*
C8	0.2941 (3)	0.5922 (2)	0.68141 (17)	0.0232 (6)
H8	0.2633	0.6365	0.7224	0.028*
C9	0.2165 (3)	0.6014 (2)	0.60506 (17)	0.0218 (6)
C10	0.2406 (3)	0.5114 (2)	0.54359 (16)	0.0196 (6)
C11	0.1878 (2)	0.3965 (2)	0.54427 (16)	0.0196 (6)
C12	0.2102 (2)	0.3183 (2)	0.48211 (16)	0.0192 (6)
C13	0.1502 (3)	0.2022 (2)	0.47167 (16)	0.0211 (6)
H13	0.0911	0.1735	0.5063	0.025*
C14	0.1783 (3)	0.1328 (2)	0.41150 (17)	0.0237 (6)
C15	0.2654 (3)	0.1713 (2)	0.35909 (17)	0.0255 (6)
H15	0.2848	0.1199	0.3184	0.031*
C16	0.3223 (3)	0.2835 (2)	0.36714 (17)	0.0242 (6)
H16	0.3817	0.3100	0.3320	0.029*
C17	0.2931 (3)	0.3600 (2)	0.42726 (16)	0.0206 (6)
C18	0.3167 (3)	0.5479 (2)	0.48365 (17)	0.0215 (6)
C19	0.3681 (3)	0.6752 (2)	0.48052 (18)	0.0269 (6)
H19A	0.4366	0.6794	0.4448	0.040*
H19B	0.4088	0.7001	0.5321	0.040*
H19C	0.2923	0.7290	0.4626	0.040*
C20	0.1112 (3)	0.3561 (2)	0.60680 (16)	0.0210 (6)
C21	−0.0006 (3)	0.4208 (2)	0.62611 (17)	0.0238 (6)
H21	−0.0310	0.4900	0.5969	0.029*
C22	−0.0675 (3)	0.3855 (3)	0.68711 (18)	0.0288 (7)
H22	−0.1427	0.4308	0.6999	0.035*
C23	−0.0251 (3)	0.2841 (3)	0.72961 (18)	0.0306 (7)
H23	−0.0697	0.2607	0.7723	0.037*
C24	0.0828 (3)	0.2169 (2)	0.70960 (18)	0.0293 (7)
H24	0.1099	0.1458	0.7377	0.035*
C25	0.1511 (3)	0.2522 (2)	0.64943 (17)	0.0250 (6)
H25	0.2256	0.2059	0.6367	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0373 (4)	0.0150 (3)	0.0400 (5)	−0.0062 (3)	0.0013 (3)	−0.0048 (3)
O1	0.0212 (10)	0.0136 (9)	0.0452 (13)	0.0019 (7)	0.0001 (9)	−0.0028 (8)
N1	0.0180 (11)	0.0158 (11)	0.0339 (14)	0.0000 (9)	0.0036 (9)	0.0010 (9)
C1	0.0213 (13)	0.0120 (12)	0.0325 (16)	−0.0028 (10)	0.0048 (11)	0.0020 (10)
C2	0.0247 (14)	0.0163 (13)	0.0354 (17)	0.0002 (10)	0.0042 (12)	−0.0017 (11)
C3	0.0313 (16)	0.0166 (13)	0.0342 (17)	−0.0025 (11)	0.0026 (12)	−0.0023 (11)
C4	0.0320 (16)	0.0165 (13)	0.0348 (17)	−0.0024 (11)	−0.0034 (13)	0.0032 (11)
C5	0.0248 (15)	0.0170 (13)	0.0442 (19)	0.0037 (11)	−0.0011 (13)	0.0019 (12)
C6	0.0255 (14)	0.0172 (13)	0.0340 (17)	0.0015 (11)	0.0060 (12)	−0.0009 (11)
C7	0.0221 (14)	0.0118 (11)	0.0326 (16)	−0.0023 (10)	0.0070 (11)	−0.0002 (11)
C8	0.0245 (14)	0.0155 (12)	0.0302 (16)	0.0010 (10)	0.0056 (11)	−0.0036 (11)
C9	0.0162 (13)	0.0122 (12)	0.0371 (16)	−0.0043 (10)	0.0038 (11)	−0.0005 (11)
C10	0.0153 (12)	0.0151 (12)	0.0279 (15)	0.0016 (10)	0.0004 (10)	0.0016 (10)
C11	0.0126 (12)	0.0154 (12)	0.0298 (15)	0.0007 (9)	−0.0014 (10)	0.0019 (10)
C12	0.0115 (12)	0.0158 (12)	0.0298 (15)	0.0020 (9)	0.0005 (10)	0.0012 (10)
C13	0.0156 (12)	0.0153 (12)	0.0320 (16)	0.0011 (10)	0.0018 (11)	0.0017 (11)
C14	0.0237 (14)	0.0134 (12)	0.0326 (16)	0.0009 (10)	−0.0023 (11)	0.0009 (11)
C15	0.0283 (15)	0.0171 (13)	0.0310 (16)	0.0054 (11)	0.0035 (12)	−0.0025 (11)
C16	0.0196 (13)	0.0209 (13)	0.0324 (16)	0.0011 (11)	0.0039 (11)	0.0009 (11)
C17	0.0139 (12)	0.0148 (12)	0.0329 (16)	0.0013 (9)	0.0017 (10)	0.0014 (11)
C18	0.0163 (13)	0.0143 (12)	0.0332 (16)	−0.0002 (10)	0.0002 (11)	0.0014 (11)
C19	0.0246 (14)	0.0149 (13)	0.0416 (18)	−0.0036 (11)	0.0059 (12)	0.0009 (12)
C20	0.0191 (13)	0.0138 (12)	0.0294 (15)	−0.0042 (9)	0.0003 (11)	−0.0011 (10)
C21	0.0182 (13)	0.0177 (13)	0.0348 (17)	−0.0018 (10)	0.0013 (11)	−0.0017 (11)
C22	0.0206 (14)	0.0254 (14)	0.0409 (18)	−0.0062 (11)	0.0066 (12)	−0.0082 (13)
C23	0.0322 (16)	0.0280 (15)	0.0329 (17)	−0.0155 (13)	0.0085 (13)	−0.0038 (12)
C24	0.0374 (17)	0.0172 (13)	0.0319 (17)	−0.0087 (12)	−0.0007 (13)	0.0029 (12)
C25	0.0273 (14)	0.0134 (12)	0.0334 (17)	−0.0018 (10)	0.0000 (12)	−0.0012 (11)

Geometric parameters (Å, º) top

Cl1—C14	1.739 (3)	C12—C17	1.417 (4)
O1—C9	1.228 (3)	C12—C13	1.422 (3)
N1—C18	1.314 (4)	C13—C14	1.360 (4)
N1—C17	1.379 (3)	C13—H13	0.9500
C1—C2	1.396 (4)	C14—C15	1.403 (4)
C1—C6	1.399 (4)	C15—C16	1.368 (4)
C1—C7	1.457 (4)	C15—H15	0.9500
C2—C3	1.379 (4)	C16—C17	1.409 (4)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.391 (4)	C18—C19	1.506 (3)
C3—H3	0.9500	C19—H19A	0.9800
C4—C5	1.382 (4)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.384 (4)	C20—C21	1.399 (4)
C5—H5	0.9500	C20—C25	1.402 (4)
C6—H6	0.9500	C21—C22	1.381 (4)
C7—C8	1.340 (4)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.384 (4)
C8—C9	1.457 (4)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.385 (4)
C9—C10	1.508 (4)	C23—H23	0.9500
C10—C11	1.380 (3)	C24—C25	1.377 (4)
C10—C18	1.425 (4)	C24—H24	0.9500
C11—C12	1.429 (4)	C25—H25	0.9500
C11—C20	1.477 (4)

C18—N1—C17	117.8 (2)	C13—C14—C15	122.3 (2)
C2—C1—C6	118.3 (3)	C13—C14—Cl1	119.8 (2)
C2—C1—C7	123.4 (2)	C15—C14—Cl1	117.8 (2)
C6—C1—C7	118.3 (3)	C16—C15—C14	119.4 (3)
C3—C2—C1	120.9 (3)	C16—C15—H15	120.3
C3—C2—H2	119.6	C14—C15—H15	120.3
C1—C2—H2	119.6	C15—C16—C17	120.3 (3)
C2—C3—C4	120.1 (3)	C15—C16—H16	119.8
C2—C3—H3	119.9	C17—C16—H16	119.8
C4—C3—H3	119.9	N1—C17—C16	117.3 (2)
C5—C4—C3	119.9 (3)	N1—C17—C12	122.7 (2)
C5—C4—H4	120.1	C16—C17—C12	119.9 (2)
C3—C4—H4	120.1	N1—C18—C10	123.1 (2)
C4—C5—C6	120.0 (3)	N1—C18—C19	116.4 (3)
C4—C5—H5	120.0	C10—C18—C19	120.5 (2)
C6—C5—H5	120.0	C18—C19—H19A	109.5
C5—C6—C1	120.8 (3)	C18—C19—H19B	109.5
C5—C6—H6	119.6	H19A—C19—H19B	109.5
C1—C6—H6	119.6	C18—C19—H19C	109.5
C8—C7—C1	126.9 (3)	H19A—C19—H19C	109.5
C8—C7—H7	116.6	H19B—C19—H19C	109.5
C1—C7—H7	116.6	C21—C20—C25	118.3 (3)
C7—C8—C9	124.0 (3)	C21—C20—C11	121.4 (2)
C7—C8—H8	118.0	C25—C20—C11	120.4 (2)
C9—C8—H8	118.0	C22—C21—C20	120.9 (3)
O1—C9—C8	121.3 (2)	C22—C21—H21	119.6
O1—C9—C10	119.3 (3)	C20—C21—H21	119.6
C8—C9—C10	119.4 (2)	C21—C22—C23	120.1 (3)
C11—C10—C18	120.5 (2)	C21—C22—H22	120.0
C11—C10—C9	120.8 (2)	C23—C22—H22	120.0
C18—C10—C9	118.7 (2)	C22—C23—C24	119.7 (3)
C10—C11—C12	117.3 (2)	C22—C23—H23	120.2
C10—C11—C20	121.2 (2)	C24—C23—H23	120.2
C12—C11—C20	121.5 (2)	C25—C24—C23	120.7 (3)
C17—C12—C13	118.6 (2)	C25—C24—H24	119.7
C17—C12—C11	118.3 (2)	C23—C24—H24	119.7
C13—C12—C11	123.0 (2)	C24—C25—C20	120.4 (3)
C14—C13—C12	119.3 (3)	C24—C25—H25	119.8
C14—C13—H13	120.4	C20—C25—H25	119.8
C12—C13—H13	120.4

C6—C1—C2—C3	−1.5 (4)	C13—C14—C15—C16	−1.5 (4)
C7—C1—C2—C3	176.5 (3)	Cl1—C14—C15—C16	176.6 (2)
C1—C2—C3—C4	0.8 (4)	C14—C15—C16—C17	−0.3 (4)
C2—C3—C4—C5	0.2 (4)	C18—N1—C17—C16	178.5 (2)
C3—C4—C5—C6	−0.6 (4)	C18—N1—C17—C12	−0.3 (4)
C4—C5—C6—C1	−0.1 (4)	C15—C16—C17—N1	−175.5 (2)
C2—C1—C6—C5	1.1 (4)	C15—C16—C17—C12	3.3 (4)
C7—C1—C6—C5	−177.0 (3)	C13—C12—C17—N1	174.2 (2)
C2—C1—C7—C8	0.2 (4)	C11—C12—C17—N1	−4.0 (4)
C6—C1—C7—C8	178.2 (3)	C13—C12—C17—C16	−4.5 (4)
C1—C7—C8—C9	176.9 (2)	C11—C12—C17—C16	177.2 (2)
C7—C8—C9—O1	−163.7 (3)	C17—N1—C18—C10	4.0 (4)
C7—C8—C9—C10	14.7 (4)	C17—N1—C18—C19	−176.0 (2)
O1—C9—C10—C11	−104.5 (3)	C11—C10—C18—N1	−3.2 (4)
C8—C9—C10—C11	77.1 (3)	C9—C10—C18—N1	178.2 (2)
O1—C9—C10—C18	74.1 (3)	C11—C10—C18—C19	176.8 (2)
C8—C9—C10—C18	−104.3 (3)	C9—C10—C18—C19	−1.9 (4)
C18—C10—C11—C12	−1.3 (4)	C10—C11—C20—C21	54.1 (4)
C9—C10—C11—C12	177.3 (2)	C12—C11—C20—C21	−126.0 (3)
C18—C10—C11—C20	178.7 (2)	C10—C11—C20—C25	−124.8 (3)
C9—C10—C11—C20	−2.7 (4)	C12—C11—C20—C25	55.2 (3)
C10—C11—C12—C17	4.6 (3)	C25—C20—C21—C22	2.0 (4)
C20—C11—C12—C17	−175.4 (2)	C11—C20—C21—C22	−176.9 (2)
C10—C11—C12—C13	−173.6 (2)	C20—C21—C22—C23	−0.7 (4)
C20—C11—C12—C13	6.5 (4)	C21—C22—C23—C24	−1.4 (4)
C17—C12—C13—C14	2.7 (4)	C22—C23—C24—C25	2.1 (4)
C11—C12—C13—C14	−179.1 (2)	C23—C24—C25—C20	−0.8 (4)
C12—C13—C14—C15	0.3 (4)	C21—C20—C25—C24	−1.2 (4)
C12—C13—C14—Cl1	−177.80 (19)	C11—C20—C25—C24	177.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C10–C12,C17,C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.48	3.315 (3)	146
C21—H21···Cg1ⁱⁱ	0.95	2.71	3.459 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₂₅H₁₈ClNO
M_r	383.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.9250 (9), 11.1001 (9), 17.4651 (15)
β (°)	97.250 (1)
V (Å³)	1908.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.46 × 0.30 × 0.26

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.536, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16152, 3948, 3030
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.188, 1.09
No. of reflections	3948
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.49

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C10–C12,C17,C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.48	3.315 (3)	146
C21—H21···Cg1ⁱⁱ	0.95	2.71	3.459 (3)	137

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

Footnotes

‡Additional correspondence author, e-mail: kvpsvijayakumar@gmail.com.

Acknowledgements

VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1998). J. Med. Chem. 31, 1031–1035. CrossRef Web of Science 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
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar
Zi, X. & Simoneau, A. R. (2005). Cancer Res. 65, 3479–3486. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1780

doi:10.1107/S160053681002386X

Open

access