(2E)-3-(2-Chloro-6-methyl-3-quinol-yl)-1-(1-naphth-yl)prop-2-en-1-one.

In the title mol-ecule, C(23)H(16)ClNO, the quinoline and naphthalene ring systems are individually planar, with maximum deviations of 0.020 (2) and 0.033 (2) Å, respectively, and are inclined at a dihedral angle of 30.01 (4)°. Intra-molecular C-H⋯O and C-H⋯Cl inter-actions occur. The crystal structure is devoid of any classical hydrogen bonds, but symmetry-related mol-ecules are linked via weak C-H⋯Cl inter-actions, forming chains propagating in [001].

Related literature

For background literature on chalcones, see: Drexler & Amiridis (2003 ▶); Opletalova & Sedivy (1999 ▶); Oyedapo et al. (2004 ▶); Prabhavat & Ghiya (1998 ▶); Varga et al. (2003 ▶). For bond distances, see: Allen (2002 ▶). For the preparation of 2-chloro-6-methyl-3-formyl­quinoline, see: Meth-Cohn et al. (1981 ▶).

Experimental

Crystal data

C23H16ClNO

M = 357.82

Monoclinic,

a = 16.919 (8) Å

b = 7.146 (3) Å

c = 14.829 (5) Å

β = 103.29 (2)°

V = 1744.9 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.14 × 0.12 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.968, T max = 0.989

6886 measured reflections

3988 independent reflections

2575 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.131

S = 1.01

3988 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007828/su2165sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007828/su2165Isup2.hkl

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

C23H16ClNO	F(000) = 744
Mr = 357.82	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6886 reflections
a = 16.919 (8) Å	θ = 2.8–27.5°
b = 7.146 (3) Å	µ = 0.23 mm−1
c = 14.829 (5) Å	T = 173 K
β = 103.29 (2)°	Plate, light yellow
V = 1744.9 (13) Å3	0.14 × 0.12 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	3988 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω and φ scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −21→21
Tmin = 0.968, Tmax = 0.989	k = −8→9
6886 measured reflections	l = −19→19

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F2) = 0.131	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.6476P] where P = (Fo2 + 2Fc2)/3
3988 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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	0.05985 (4)	0.69090 (9)	0.33367 (3)	0.0466 (2)
O1	0.29189 (9)	0.9031 (2)	0.21743 (9)	0.0428 (4)
N1	−0.07435 (11)	0.6646 (3)	0.20914 (11)	0.0364 (4)
C1	−0.12197 (12)	0.6652 (3)	0.11997 (13)	0.0319 (5)
C2	−0.20482 (13)	0.6170 (3)	0.10550 (15)	0.0378 (5)
H2	−0.2275	0.5874	0.1567	0.045*
C3	−0.25230 (13)	0.6132 (3)	0.01723 (15)	0.0374 (5)
H3	−0.3080	0.5801	0.0081	0.045*
C4	−0.22076 (13)	0.6572 (3)	−0.06116 (14)	0.0353 (5)
C5	−0.14061 (13)	0.7047 (3)	−0.04742 (14)	0.0344 (5)
H5	−0.1190	0.7363	−0.0992	0.041*
C6	−0.08912 (13)	0.7078 (3)	0.04277 (13)	0.0314 (5)
C7	−0.00604 (13)	0.7522 (3)	0.05985 (14)	0.0338 (5)
H7	0.0172	0.7835	0.0092	0.041*
C8	0.04260 (13)	0.7514 (3)	0.14841 (13)	0.0317 (5)
C9	0.00187 (13)	0.7035 (3)	0.21931 (13)	0.0328 (5)
C10	−0.27558 (15)	0.6499 (4)	−0.15703 (16)	0.0481 (6)
H10A	−0.2452	0.6896	−0.2026	0.058*
H10B	−0.3219	0.7338	−0.1600	0.058*
H10C	−0.2952	0.5217	−0.1708	0.058*
C11	0.12863 (13)	0.8006 (3)	0.16855 (13)	0.0340 (5)
H11	0.1533	0.8344	0.2306	0.041*
C12	0.17573 (13)	0.8023 (3)	0.10796 (14)	0.0338 (5)
H12	0.1535	0.7696	0.0452	0.041*
C13	0.26277 (13)	0.8548 (3)	0.13762 (13)	0.0322 (5)
C14	0.31294 (12)	0.8425 (3)	0.06743 (13)	0.0295 (5)
C15	0.27849 (14)	0.8918 (3)	−0.02286 (13)	0.0361 (5)
H15	0.2231	0.9285	−0.0390	0.043*
C16	0.32305 (16)	0.8890 (4)	−0.09110 (15)	0.0551 (7)
H16	0.2983	0.9253	−0.1528	0.066*
C17	0.40178 (17)	0.8344 (5)	−0.06904 (16)	0.0718 (10)
H17	0.4316	0.8325	−0.1160	0.086*
C18	0.44086 (14)	0.7800 (4)	0.02193 (15)	0.0489 (7)
C19	0.52216 (17)	0.7176 (5)	0.04411 (19)	0.0776 (11)
H19	0.5520	0.7158	−0.0029	0.093*
C20	0.55878 (16)	0.6603 (5)	0.13079 (18)	0.0637 (8)
H20	0.6136	0.6191	0.1443	0.076*
C21	0.51529 (14)	0.6622 (3)	0.19988 (16)	0.0439 (6)
H21	0.5407	0.6211	0.2605	0.053*
C22	0.43669 (13)	0.7222 (3)	0.18163 (14)	0.0361 (5)
H22	0.4084	0.7225	0.2300	0.043*
C23	0.39635 (12)	0.7843 (3)	0.09213 (13)	0.0309 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0431 (4)	0.0673 (4)	0.0265 (3)	−0.0126 (3)	0.0024 (2)	0.0045 (3)
O1	0.0350 (9)	0.0637 (11)	0.0287 (7)	−0.0057 (8)	0.0053 (6)	−0.0084 (7)
N1	0.0347 (11)	0.0459 (11)	0.0292 (9)	−0.0018 (9)	0.0088 (7)	0.0014 (8)
C1	0.0296 (12)	0.0357 (12)	0.0304 (10)	0.0007 (9)	0.0069 (8)	−0.0012 (9)
C2	0.0325 (12)	0.0425 (14)	0.0404 (11)	0.0001 (10)	0.0122 (9)	0.0013 (10)
C3	0.0278 (12)	0.0360 (13)	0.0471 (12)	0.0011 (10)	0.0056 (9)	−0.0001 (10)
C4	0.0336 (12)	0.0302 (12)	0.0387 (11)	0.0032 (9)	0.0014 (9)	−0.0003 (9)
C5	0.0365 (13)	0.0357 (12)	0.0306 (10)	−0.0006 (10)	0.0071 (9)	0.0002 (9)
C6	0.0310 (12)	0.0334 (12)	0.0301 (10)	0.0008 (9)	0.0074 (8)	−0.0015 (9)
C7	0.0340 (12)	0.0409 (13)	0.0282 (10)	−0.0013 (10)	0.0107 (8)	−0.0011 (9)
C8	0.0301 (11)	0.0371 (12)	0.0284 (10)	−0.0013 (9)	0.0081 (8)	−0.0031 (9)
C9	0.0329 (12)	0.0396 (13)	0.0256 (9)	−0.0005 (10)	0.0059 (8)	−0.0007 (9)
C10	0.0419 (14)	0.0500 (15)	0.0448 (13)	−0.0038 (12)	−0.0056 (11)	0.0043 (11)
C11	0.0318 (12)	0.0404 (13)	0.0287 (10)	−0.0021 (10)	0.0043 (8)	−0.0006 (9)
C12	0.0298 (11)	0.0418 (13)	0.0284 (9)	−0.0005 (10)	0.0041 (8)	−0.0034 (9)
C13	0.0297 (12)	0.0363 (12)	0.0294 (10)	−0.0014 (9)	0.0041 (8)	−0.0007 (9)
C14	0.0277 (11)	0.0319 (12)	0.0277 (9)	−0.0013 (9)	0.0039 (8)	−0.0022 (8)
C15	0.0323 (12)	0.0427 (13)	0.0309 (10)	0.0031 (10)	0.0023 (9)	0.0004 (9)
C16	0.0447 (15)	0.093 (2)	0.0267 (11)	0.0093 (14)	0.0061 (10)	0.0086 (12)
C17	0.0466 (17)	0.142 (3)	0.0321 (12)	0.0179 (18)	0.0187 (11)	0.0051 (16)
C18	0.0329 (13)	0.080 (2)	0.0340 (11)	0.0100 (13)	0.0085 (9)	−0.0020 (12)
C19	0.0408 (16)	0.148 (3)	0.0466 (14)	0.0298 (19)	0.0155 (12)	−0.0024 (18)
C20	0.0354 (15)	0.094 (2)	0.0567 (16)	0.0209 (15)	0.0012 (12)	−0.0071 (15)
C21	0.0383 (14)	0.0456 (14)	0.0409 (12)	0.0005 (11)	−0.0051 (10)	0.0013 (11)
C22	0.0321 (12)	0.0404 (13)	0.0335 (11)	−0.0040 (10)	0.0025 (9)	0.0028 (9)
C23	0.0281 (11)	0.0341 (12)	0.0290 (10)	−0.0021 (9)	0.0035 (8)	−0.0033 (9)

Cl1—C9	1.755 (2)	C11—H11	0.9500
O1—C13	1.222 (2)	C12—C13	1.485 (3)
N1—C9	1.294 (3)	C12—H12	0.9500
N1—C1	1.381 (3)	C13—C14	1.489 (3)
C1—C2	1.411 (3)	C14—C15	1.378 (3)
C1—C6	1.416 (3)	C14—C23	1.436 (3)
C2—C3	1.370 (3)	C15—C16	1.394 (3)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.421 (3)	C16—C17	1.354 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.367 (3)	C17—C18	1.414 (3)
C4—C10	1.509 (3)	C17—H17	0.9500
C5—C6	1.419 (3)	C18—C19	1.411 (4)
C5—H5	0.9500	C18—C23	1.418 (3)
C6—C7	1.406 (3)	C19—C20	1.356 (4)
C7—C8	1.380 (3)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.392 (4)
C8—C9	1.425 (3)	C20—H20	0.9500
C8—C11	1.460 (3)	C21—C22	1.364 (3)
C10—H10A	0.9800	C21—H21	0.9500
C10—H10B	0.9800	C22—C23	1.417 (3)
C10—H10C	0.9800	C22—H22	0.9500
C11—C12	1.331 (3)
C9—N1—C1	117.22 (17)	C11—C12—C13	120.61 (18)
N1—C1—C2	119.03 (18)	C11—C12—H12	119.7
N1—C1—C6	121.58 (19)	C13—C12—H12	119.7
C2—C1—C6	119.37 (18)	O1—C13—C12	120.64 (19)
C3—C2—C1	119.6 (2)	O1—C13—C14	121.71 (19)
C3—C2—H2	120.2	C12—C13—C14	117.64 (17)
C1—C2—H2	120.2	C15—C14—C23	119.57 (18)
C2—C3—C4	122.0 (2)	C15—C14—C13	118.85 (19)
C2—C3—H3	119.0	C23—C14—C13	121.57 (17)
C4—C3—H3	119.0	C14—C15—C16	121.6 (2)
C5—C4—C3	118.63 (19)	C14—C15—H15	119.2
C5—C4—C10	121.5 (2)	C16—C15—H15	119.2
C3—C4—C10	119.9 (2)	C17—C16—C15	119.7 (2)
C4—C5—C6	121.2 (2)	C17—C16—H16	120.2
C4—C5—H5	119.4	C15—C16—H16	120.2
C6—C5—H5	119.4	C16—C17—C18	121.9 (2)
C7—C6—C1	117.71 (18)	C16—C17—H17	119.1
C7—C6—C5	123.03 (19)	C18—C17—H17	119.1
C1—C6—C5	119.26 (19)	C19—C18—C17	121.8 (2)
C8—C7—C6	121.54 (19)	C19—C18—C23	119.3 (2)
C8—C7—H7	119.2	C17—C18—C23	118.9 (2)
C6—C7—H7	119.2	C20—C19—C18	121.7 (2)
C7—C8—C9	114.79 (19)	C20—C19—H19	119.2
C7—C8—C11	122.81 (19)	C18—C19—H19	119.2
C9—C8—C11	122.37 (18)	C19—C20—C21	119.4 (2)
N1—C9—C8	127.14 (18)	C19—C20—H20	120.3
N1—C9—Cl1	114.98 (15)	C21—C20—H20	120.3
C8—C9—Cl1	117.87 (16)	C22—C21—C20	120.9 (2)
C4—C10—H10A	109.5	C22—C21—H21	119.6
C4—C10—H10B	109.5	C20—C21—H21	119.6
H10A—C10—H10B	109.5	C21—C22—C23	121.5 (2)
C4—C10—H10C	109.5	C21—C22—H22	119.3
H10A—C10—H10C	109.5	C23—C22—H22	119.3
H10B—C10—H10C	109.5	C22—C23—C18	117.3 (2)
C12—C11—C8	125.99 (19)	C22—C23—C14	124.28 (19)
C12—C11—H11	117.0	C18—C23—C14	118.41 (18)
C8—C11—H11	117.0
C9—N1—C1—C2	177.8 (2)	C11—C12—C13—O1	−2.4 (3)
C9—N1—C1—C6	−0.4 (3)	C11—C12—C13—C14	176.4 (2)
N1—C1—C2—C3	−178.6 (2)	O1—C13—C14—C15	−143.8 (2)
C6—C1—C2—C3	−0.3 (3)	C12—C13—C14—C15	37.4 (3)
C1—C2—C3—C4	−0.3 (3)	O1—C13—C14—C23	34.9 (3)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C23	−143.8 (2)
C2—C3—C4—C10	179.7 (2)	C23—C14—C15—C16	−0.9 (3)
C3—C4—C5—C6	0.9 (3)	C13—C14—C15—C16	177.9 (2)
C10—C4—C5—C6	−178.8 (2)	C14—C15—C16—C17	0.9 (4)
N1—C1—C6—C7	−0.8 (3)	C15—C16—C17—C18	−0.2 (5)
C2—C1—C6—C7	−179.0 (2)	C16—C17—C18—C19	178.0 (3)
N1—C1—C6—C5	179.4 (2)	C16—C17—C18—C23	−0.5 (5)
C2—C1—C6—C5	1.2 (3)	C17—C18—C19—C20	−178.0 (3)
C4—C5—C6—C7	178.7 (2)	C23—C18—C19—C20	0.5 (5)
C4—C5—C6—C1	−1.5 (3)	C18—C19—C20—C21	0.2 (5)
C1—C6—C7—C8	1.1 (3)	C19—C20—C21—C22	−0.5 (5)
C5—C6—C7—C8	−179.1 (2)	C20—C21—C22—C23	0.1 (4)
C6—C7—C8—C9	−0.3 (3)	C21—C22—C23—C18	0.5 (3)
C6—C7—C8—C11	−178.7 (2)	C21—C22—C23—C14	177.5 (2)
C1—N1—C9—C8	1.5 (3)	C19—C18—C23—C22	−0.8 (4)
C1—N1—C9—Cl1	−177.48 (16)	C17—C18—C23—C22	177.7 (3)
C7—C8—C9—N1	−1.1 (3)	C19—C18—C23—C14	−178.0 (3)
C11—C8—C9—N1	177.3 (2)	C17—C18—C23—C14	0.5 (4)
C7—C8—C9—Cl1	177.80 (17)	C15—C14—C23—C22	−176.9 (2)
C11—C8—C9—Cl1	−3.7 (3)	C13—C14—C23—C22	4.4 (3)
C7—C8—C11—C12	−19.2 (4)	C15—C14—C23—C18	0.1 (3)
C9—C8—C11—C12	162.5 (2)	C13—C14—C23—C18	−178.6 (2)
C8—C11—C12—C13	−179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1i	0.95	2.86	3.792 (2)	166
C11—H11···Cl1	0.95	2.65	3.045 (2)	106
C11—H11···O1	0.95	2.45	2.788 (3)	101
C22—H22···O1	0.95	2.33	2.924 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cl1i	0.95	2.86	3.792 (2)	166
C11—H11⋯Cl1	0.95	2.65	3.045 (2)	106
C11—H11⋯O1	0.95	2.45	2.788 (3)	101
C22—H22⋯O1	0.95	2.33	2.924 (3)	120

Symmetry code: (i) .