(E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol-yl)-3-(2-methoxy-phen-yl)prop-2-en-1-one.

In the title compound, C(26)H(20)ClNO(2), the quinoline ring system and the methoxy-phenyl 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, mol-ecules exist as C-H⋯O hydrogen-bonded dimers. The structure is further stabilized by C-H⋯π inter-actions.

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 = 413.88

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.136

S = 1.06

8197 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.31 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000784/ci5015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000784/ci5015Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H20ClNO2	F(000) = 1728
Mr = 413.88	Dx = 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

Bruker SMART APEXII CCD area-detector diffractometer	8197 independent reflections
Radiation source: fine-focus sealed tube	5864 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 34.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→24
Tmin = 0.919, Tmax = 0.960	k = −24→19
30753 measured reflections	l = −27→27

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(Fo2) + (0.0625P)2 + 0.7227P] where P = (Fo2 + 2Fc2)/3
8197 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .