(2E,4E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol-yl)-5-phenyl-penta-2,4-dien-1-one.

In the title compound, C(27)H(20)ClNO, the quinoline ring forms a dihedral angle of 62.53 (5)° with the substituent benzene ring. In the crystal, inter-molecular C-H⋯Cl inter-actions link the mol-ecules into chains along the b axis. Inter-molecular C-H⋯N and C-H⋯O hydrogen bonds further consolidate the structure into a three-dimensional network. The unit cell contains four solvent-accessible voids, each with a volume of 35 Å(3), but no significant electron density was found in them.

Related literature

For the background to and the biological activity of quinolines, see: Bhat et al. (2005 ▶); Markees et al. (1970 ▶); Campbell et al. (1998 ▶). For related structures, see: Loh et al. (2010a ▶,b ▶); Shahani et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H20ClNO

M = 409.89

Monoclinic,

a = 6.2464 (3) Å

b = 22.5672 (11) Å

c = 15.2748 (7) Å

β = 94.620 (1)°

V = 2146.20 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.35 × 0.26 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.935, T max = 0.975

22989 measured reflections

6191 independent reflections

4889 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.03

6191 reflections

351 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.33 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/S1600536810016429/fj2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016429/fj2295Isup2.hkl

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

C27H20ClNO	F(000) = 856
Mr = 409.89	Dx = 1.269 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7467 reflections
a = 6.2464 (3) Å	θ = 2.7–30.1°
b = 22.5672 (11) Å	µ = 0.20 mm−1
c = 15.2748 (7) Å	T = 100 K
β = 94.620 (1)°	Block, yellow
V = 2146.20 (18) Å3	0.35 × 0.26 × 0.13 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	6191 independent reflections
Radiation source: fine-focus sealed tube	4889 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.935, Tmax = 0.975	k = −31→30
22989 measured reflections	l = −21→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.7188P] where P = (Fo2 + 2Fc2)/3
6191 reflections	(Δ/σ)max < 0.001
351 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.98899 (7)	0.715737 (13)	0.90927 (2)	0.02946 (10)
O1	1.25735 (15)	0.37767 (4)	0.78500 (6)	0.0222 (2)
N1	0.74535 (17)	0.46489 (5)	0.93300 (6)	0.0166 (2)
C1	0.8209 (2)	0.42457 (5)	0.88123 (7)	0.0157 (2)
C2	0.8083 (2)	0.52252 (5)	0.92445 (7)	0.0150 (2)
C3	0.7221 (2)	0.56504 (6)	0.98060 (8)	0.0184 (2)
C4	0.7763 (2)	0.62357 (6)	0.97496 (8)	0.0201 (2)
C5	0.9190 (2)	0.64118 (5)	0.91295 (8)	0.0198 (3)
C6	1.0057 (2)	0.60204 (5)	0.85712 (7)	0.0179 (2)
C7	0.9518 (2)	0.54095 (5)	0.86241 (7)	0.0148 (2)
C8	1.03265 (19)	0.49667 (5)	0.80677 (7)	0.0141 (2)
C9	0.9673 (2)	0.43886 (5)	0.81688 (7)	0.0146 (2)
C10	1.0682 (2)	0.39015 (5)	0.76648 (7)	0.0165 (2)
C11	0.9424 (2)	0.35894 (5)	0.69584 (8)	0.0196 (2)
C12	0.7385 (2)	0.37191 (5)	0.66730 (8)	0.0186 (2)
C13	0.6247 (2)	0.34261 (6)	0.59338 (8)	0.0199 (2)
C14	0.4235 (2)	0.35703 (5)	0.56358 (8)	0.0183 (2)
C15	0.2997 (2)	0.33203 (5)	0.48666 (7)	0.0177 (2)
C16	0.3789 (2)	0.28695 (6)	0.43480 (8)	0.0222 (3)
C17	0.2553 (3)	0.26556 (6)	0.36195 (9)	0.0266 (3)
C18	0.0520 (3)	0.28854 (6)	0.33945 (9)	0.0271 (3)
C19	−0.0284 (2)	0.33317 (6)	0.38964 (9)	0.0258 (3)
C20	0.0949 (2)	0.35471 (6)	0.46291 (8)	0.0216 (3)
C21	1.1795 (2)	0.51281 (5)	0.73818 (7)	0.0150 (2)
C22	1.3818 (2)	0.53707 (6)	0.76042 (8)	0.0202 (2)
C23	1.5169 (2)	0.55152 (6)	0.69544 (9)	0.0224 (3)
C24	1.4518 (2)	0.54137 (6)	0.60747 (8)	0.0218 (3)
C25	1.2500 (2)	0.51754 (6)	0.58481 (8)	0.0198 (2)
C26	1.1141 (2)	0.50339 (5)	0.64940 (7)	0.0169 (2)
C27	0.7482 (2)	0.36175 (6)	0.89417 (8)	0.0198 (2)
H3A	0.623 (3)	0.5505 (7)	1.0210 (10)	0.022 (4)*
H4A	0.715 (3)	0.6527 (8)	1.0137 (11)	0.028 (4)*
H6A	1.105 (3)	0.6164 (7)	0.8149 (11)	0.024 (4)*
H11A	1.022 (3)	0.3273 (7)	0.6669 (11)	0.027 (4)*
H12A	0.658 (3)	0.4025 (7)	0.6958 (11)	0.023 (4)*
H13A	0.705 (3)	0.3126 (8)	0.5649 (11)	0.029 (4)*
H14A	0.352 (2)	0.3879 (7)	0.5961 (10)	0.018 (4)*
H16A	0.527 (3)	0.2710 (8)	0.4492 (12)	0.031 (4)*
H17A	0.316 (3)	0.2329 (8)	0.3271 (12)	0.033 (5)*
H18A	−0.032 (3)	0.2749 (8)	0.2885 (12)	0.036 (5)*
H19A	−0.179 (3)	0.3514 (8)	0.3763 (12)	0.036 (5)*
H20A	0.035 (3)	0.3861 (7)	0.4993 (10)	0.020 (4)*
H22A	1.423 (3)	0.5431 (8)	0.8233 (11)	0.028 (4)*
H23A	1.660 (3)	0.5687 (8)	0.7123 (11)	0.027 (4)*
H24A	1.547 (3)	0.5514 (7)	0.5628 (11)	0.026 (4)*
H25A	1.202 (3)	0.5110 (7)	0.5228 (11)	0.024 (4)*
H26A	0.975 (3)	0.4861 (8)	0.6324 (11)	0.027 (4)*
H27A	0.695 (3)	0.3575 (8)	0.9527 (12)	0.031 (4)*
H27B	0.860 (3)	0.3318 (8)	0.8870 (11)	0.029 (4)*
H27C	0.629 (3)	0.3524 (8)	0.8503 (12)	0.034 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0483 (2)	0.01405 (14)	0.02701 (16)	−0.00199 (14)	0.00901 (14)	−0.00136 (10)
O1	0.0177 (5)	0.0229 (4)	0.0256 (4)	0.0039 (4)	−0.0005 (4)	−0.0005 (3)
N1	0.0146 (5)	0.0189 (5)	0.0162 (4)	−0.0007 (4)	0.0013 (4)	0.0001 (3)
C1	0.0140 (6)	0.0171 (5)	0.0155 (5)	−0.0004 (4)	−0.0017 (4)	0.0008 (4)
C2	0.0133 (5)	0.0175 (5)	0.0139 (5)	0.0000 (4)	−0.0003 (4)	−0.0004 (4)
C3	0.0167 (6)	0.0222 (6)	0.0165 (5)	0.0001 (5)	0.0022 (4)	−0.0024 (4)
C4	0.0214 (6)	0.0207 (6)	0.0183 (5)	0.0024 (5)	0.0026 (5)	−0.0038 (4)
C5	0.0255 (7)	0.0148 (5)	0.0188 (5)	0.0002 (5)	0.0010 (5)	−0.0006 (4)
C6	0.0219 (6)	0.0165 (5)	0.0154 (5)	−0.0003 (5)	0.0020 (5)	0.0011 (4)
C7	0.0157 (6)	0.0162 (5)	0.0122 (4)	−0.0003 (4)	−0.0012 (4)	0.0001 (4)
C8	0.0136 (5)	0.0164 (5)	0.0122 (4)	0.0008 (4)	−0.0004 (4)	0.0004 (4)
C9	0.0148 (6)	0.0156 (5)	0.0132 (4)	0.0012 (4)	−0.0008 (4)	−0.0008 (4)
C10	0.0188 (6)	0.0148 (5)	0.0161 (5)	0.0003 (5)	0.0024 (4)	0.0007 (4)
C11	0.0221 (7)	0.0164 (5)	0.0204 (5)	0.0003 (5)	0.0016 (5)	−0.0035 (4)
C12	0.0221 (6)	0.0160 (5)	0.0178 (5)	−0.0007 (5)	0.0023 (5)	−0.0014 (4)
C13	0.0213 (7)	0.0187 (5)	0.0196 (5)	−0.0005 (5)	0.0003 (5)	−0.0034 (4)
C14	0.0207 (6)	0.0165 (5)	0.0180 (5)	−0.0016 (5)	0.0030 (5)	−0.0017 (4)
C15	0.0198 (6)	0.0162 (5)	0.0172 (5)	−0.0032 (5)	0.0015 (4)	0.0013 (4)
C16	0.0242 (7)	0.0198 (6)	0.0225 (6)	−0.0005 (5)	0.0015 (5)	−0.0027 (4)
C17	0.0345 (8)	0.0226 (6)	0.0225 (6)	−0.0035 (6)	0.0007 (6)	−0.0052 (5)
C18	0.0343 (8)	0.0253 (6)	0.0204 (6)	−0.0063 (6)	−0.0054 (6)	−0.0009 (5)
C19	0.0256 (7)	0.0263 (6)	0.0245 (6)	−0.0015 (6)	−0.0046 (5)	0.0020 (5)
C20	0.0234 (7)	0.0207 (6)	0.0205 (5)	0.0000 (5)	0.0006 (5)	0.0007 (4)
C21	0.0160 (6)	0.0142 (5)	0.0149 (5)	0.0018 (4)	0.0017 (4)	0.0008 (4)
C22	0.0188 (6)	0.0231 (6)	0.0183 (5)	0.0002 (5)	0.0000 (5)	0.0014 (4)
C23	0.0160 (6)	0.0248 (6)	0.0265 (6)	−0.0017 (5)	0.0023 (5)	0.0017 (5)
C24	0.0224 (7)	0.0210 (6)	0.0230 (6)	0.0031 (5)	0.0082 (5)	0.0033 (4)
C25	0.0236 (7)	0.0207 (6)	0.0156 (5)	0.0021 (5)	0.0043 (5)	0.0010 (4)
C26	0.0180 (6)	0.0172 (5)	0.0154 (5)	−0.0001 (5)	0.0008 (4)	−0.0008 (4)
C27	0.0207 (7)	0.0177 (5)	0.0211 (5)	−0.0033 (5)	0.0024 (5)	0.0012 (4)

Cl1—C5	1.7405 (13)	C14—H14A	0.984 (16)
O1—C10	1.2253 (16)	C15—C20	1.3981 (19)
N1—C1	1.3175 (15)	C15—C16	1.4037 (18)
N1—C2	1.3681 (15)	C16—C17	1.3890 (18)
C1—C9	1.4322 (17)	C16—H16A	1.001 (18)
C1—C27	1.5066 (17)	C17—C18	1.389 (2)
C2—C7	1.4180 (17)	C17—H17A	1.000 (19)
C2—C3	1.4217 (16)	C18—C19	1.384 (2)
C3—C4	1.3680 (18)	C18—H18A	0.955 (19)
C3—H3A	0.967 (17)	C19—C20	1.3940 (18)
C4—C5	1.4093 (19)	C19—H19A	1.033 (19)
C4—H4A	0.981 (17)	C20—H20A	0.993 (16)
C5—C6	1.3693 (17)	C21—C22	1.3938 (18)
C6—C7	1.4230 (16)	C21—C26	1.4007 (15)
C6—H6A	0.986 (17)	C22—C23	1.3926 (18)
C7—C8	1.4302 (16)	C22—H22A	0.983 (17)
C8—C9	1.3794 (16)	C23—C24	1.3911 (18)
C8—C21	1.4921 (16)	C23—H23A	0.987 (18)
C9—C10	1.5088 (16)	C24—C25	1.389 (2)
C10—C11	1.4635 (17)	C24—H24A	0.965 (18)
C11—C12	1.3445 (19)	C25—C26	1.3897 (17)
C11—H11A	0.994 (17)	C25—H25A	0.981 (16)
C12—C13	1.4451 (16)	C26—H26A	0.967 (18)
C12—H12A	0.976 (17)	C27—H27A	0.984 (19)
C13—C14	1.3417 (19)	C27—H27B	0.985 (18)
C13—H13A	0.967 (18)	C27—H27C	0.982 (19)
C14—C15	1.4666 (16)
C1—N1—C2	118.65 (10)	C20—C15—C16	118.41 (11)
N1—C1—C9	122.41 (11)	C20—C15—C14	118.64 (11)
N1—C1—C27	116.40 (11)	C16—C15—C14	122.94 (12)
C9—C1—C27	121.18 (11)	C17—C16—C15	120.35 (13)
N1—C2—C7	123.01 (11)	C17—C16—H16A	119.7 (10)
N1—C2—C3	117.28 (11)	C15—C16—H16A	119.9 (10)
C7—C2—C3	119.71 (11)	C16—C17—C18	120.45 (13)
C4—C3—C2	120.41 (12)	C16—C17—H17A	118.2 (11)
C4—C3—H3A	122.8 (10)	C18—C17—H17A	121.3 (10)
C2—C3—H3A	116.8 (10)	C19—C18—C17	119.97 (12)
C3—C4—C5	119.18 (11)	C19—C18—H18A	119.1 (11)
C3—C4—H4A	120.0 (10)	C17—C18—H18A	120.8 (11)
C5—C4—H4A	120.8 (10)	C18—C19—C20	119.79 (14)
C6—C5—C4	122.68 (12)	C18—C19—H19A	123.1 (10)
C6—C5—Cl1	119.38 (10)	C20—C19—H19A	117.1 (10)
C4—C5—Cl1	117.93 (9)	C19—C20—C15	121.03 (13)
C5—C6—C7	118.85 (12)	C19—C20—H20A	119.4 (9)
C5—C6—H6A	119.9 (10)	C15—C20—H20A	119.6 (9)
C7—C6—H6A	121.3 (10)	C22—C21—C26	118.92 (11)
C2—C7—C6	119.16 (11)	C22—C21—C8	121.41 (10)
C2—C7—C8	117.69 (10)	C26—C21—C8	119.66 (11)
C6—C7—C8	123.15 (11)	C23—C22—C21	120.53 (11)
C9—C8—C7	118.19 (11)	C23—C22—H22A	122.6 (11)
C9—C8—C21	120.91 (10)	C21—C22—H22A	116.8 (11)
C7—C8—C21	120.88 (10)	C24—C23—C22	120.21 (13)
C8—C9—C1	120.05 (10)	C24—C23—H23A	120.3 (10)
C8—C9—C10	119.50 (11)	C22—C23—H23A	119.5 (10)
C1—C9—C10	120.15 (10)	C25—C24—C23	119.56 (12)
O1—C10—C11	120.69 (11)	C25—C24—H24A	120.7 (10)
O1—C10—C9	118.97 (10)	C23—C24—H24A	119.7 (10)
C11—C10—C9	120.34 (11)	C24—C25—C26	120.43 (11)
C12—C11—C10	124.93 (12)	C24—C25—H25A	119.9 (10)
C12—C11—H11A	120.4 (10)	C26—C25—H25A	119.7 (10)
C10—C11—H11A	114.6 (10)	C25—C26—C21	120.35 (12)
C11—C12—C13	123.17 (12)	C25—C26—H26A	119.2 (10)
C11—C12—H12A	121.2 (10)	C21—C26—H26A	120.4 (10)
C13—C12—H12A	115.7 (10)	C1—C27—H27A	109.8 (10)
C14—C13—C12	122.85 (12)	C1—C27—H27B	114.0 (10)
C14—C13—H13A	121.6 (10)	H27A—C27—H27B	109.3 (14)
C12—C13—H13A	115.5 (10)	C1—C27—H27C	109.3 (11)
C13—C14—C15	126.69 (12)	H27A—C27—H27C	107.8 (15)
C13—C14—H14A	116.9 (9)	H27B—C27—H27C	106.4 (15)
C15—C14—H14A	116.4 (9)
C2—N1—C1—C9	0.42 (17)	C1—C9—C10—O1	−105.62 (14)
C2—N1—C1—C27	179.34 (10)	C8—C9—C10—C11	−111.08 (13)
C1—N1—C2—C7	−0.12 (17)	C1—C9—C10—C11	75.19 (14)
C1—N1—C2—C3	179.31 (11)	O1—C10—C11—C12	−175.74 (12)
N1—C2—C3—C4	−179.28 (11)	C9—C10—C11—C12	3.44 (19)
C7—C2—C3—C4	0.17 (18)	C10—C11—C12—C13	175.68 (12)
C2—C3—C4—C5	−0.14 (19)	C11—C12—C13—C14	−177.89 (13)
C3—C4—C5—C6	0.4 (2)	C12—C13—C14—C15	176.62 (12)
C3—C4—C5—Cl1	−178.59 (10)	C13—C14—C15—C20	−176.86 (13)
C4—C5—C6—C7	−0.74 (19)	C13—C14—C15—C16	2.0 (2)
Cl1—C5—C6—C7	178.29 (9)	C20—C15—C16—C17	−0.23 (19)
N1—C2—C7—C6	178.96 (11)	C14—C15—C16—C17	−179.12 (12)
C3—C2—C7—C6	−0.46 (17)	C15—C16—C17—C18	0.1 (2)
N1—C2—C7—C8	0.03 (17)	C16—C17—C18—C19	0.2 (2)
C3—C2—C7—C8	−179.39 (11)	C17—C18—C19—C20	−0.3 (2)
C5—C6—C7—C2	0.73 (18)	C18—C19—C20—C15	0.1 (2)
C5—C6—C7—C8	179.60 (11)	C16—C15—C20—C19	0.11 (19)
C2—C7—C8—C9	−0.23 (16)	C14—C15—C20—C19	179.05 (12)
C6—C7—C8—C9	−179.12 (11)	C9—C8—C21—C22	−118.31 (13)
C2—C7—C8—C21	178.30 (10)	C7—C8—C21—C22	63.20 (16)
C6—C7—C8—C21	−0.59 (17)	C9—C8—C21—C26	61.54 (15)
C7—C8—C9—C1	0.52 (16)	C7—C8—C21—C26	−116.95 (13)
C21—C8—C9—C1	−178.01 (10)	C26—C21—C22—C23	−0.23 (18)
C7—C8—C9—C10	−173.22 (10)	C8—C21—C22—C23	179.63 (12)
C21—C8—C9—C10	8.26 (16)	C21—C22—C23—C24	−0.5 (2)
N1—C1—C9—C8	−0.64 (17)	C22—C23—C24—C25	0.9 (2)
C27—C1—C9—C8	−179.51 (11)	C23—C24—C25—C26	−0.54 (19)
N1—C1—C9—C10	173.05 (11)	C24—C25—C26—C21	−0.24 (19)
C27—C1—C9—C10	−5.82 (16)	C22—C21—C26—C25	0.62 (18)
C8—C9—C10—O1	68.11 (15)	C8—C21—C26—C25	−179.24 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N1i	0.966 (17)	2.484 (19)	3.3681 (16)	152.1 (14)
C11—H11A···Cl1ii	0.994 (17)	2.772 (16)	3.6491 (12)	147.4 (14)
C17—H17A···O1iii	1.000 (19)	2.596 (19)	3.4398 (17)	142.1 (14)
C27—H27C···O1iv	0.984 (18)	2.517 (19)	3.3892 (16)	147.6 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N1i	0.966 (17)	2.484 (19)	3.3681 (16)	152.1 (14)
C11—H11A⋯Cl1ii	0.994 (17)	2.772 (16)	3.6491 (12)	147.4 (14)
C17—H17A⋯O1iii	1.000 (19)	2.596 (19)	3.4398 (17)	142.1 (14)
C27—H27C⋯O1iv	0.984 (18)	2.517 (19)	3.3892 (16)	147.6 (14)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .