1-(6-Chloro-2-methyl-4-phenyl-3-quinol-yl)ethanone.

In the title compound, C(18)H(14)ClNO, the quinoline ring system is approximately planar with a maximum devation of 0.022 (1) Å and forms a dihedral angle of 62.70 (3)° with the phenyl ring. In the crystal, pairs of C-H⋯O inter-molecular hydrogen bonds link neighbouring mol-ecules into inversion dimers, forming R(2) (2)(14) ring motifs. These inversion dimers are stacked along the b axis. The structure is further stabilized by C-H⋯π inter-actions.

Related literature

For reference bond-length data, see: Allen et al. (1987 ▶). For background to quinolines, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶); Maguire et al. (1994 ▶); Kalluraya & Sreenivasa (1998 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶); Skraup (1880 ▶); Katritzky & Arend (1998 ▶); Jiang & Si (2002 ▶). For the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Yamazaki et al. (2002 ▶). For a related structure, see: Fun et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H14ClNO

M = 295.75

Monoclinic,

a = 10.4633 (2) Å

b = 7.7959 (1) Å

c = 17.5925 (3) Å

β = 90.887 (1)°

V = 1434.86 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.57 × 0.34 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.865, T max = 0.932

32340 measured reflections

7613 independent reflections

6588 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.107

S = 1.07

7613 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040306/wn2352sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040306/wn2352Isup2.hkl

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

C18H14ClNO	F(000) = 616
Mr = 295.75	Dx = 1.369 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9994 reflections
a = 10.4633 (2) Å	θ = 2.3–37.6°
b = 7.7959 (1) Å	µ = 0.26 mm−1
c = 17.5925 (3) Å	T = 100 K
β = 90.887 (1)°	Block, yellow
V = 1434.86 (4) Å3	0.57 × 0.34 × 0.27 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7613 independent reflections
Radiation source: fine-focus sealed tube	6588 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 37.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→16
Tmin = 0.865, Tmax = 0.932	k = −13→12
32340 measured reflections	l = −30→30

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.2858P] where P = (Fo2 + 2Fc2)/3
7613 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.24 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	1.179322 (16)	0.65521 (3)	0.247848 (10)	0.02152 (5)
O1	0.56817 (6)	0.27543 (9)	0.51440 (4)	0.02585 (12)
N1	0.98196 (6)	0.23575 (8)	0.49910 (3)	0.01532 (10)
C1	0.98802 (6)	0.50843 (9)	0.32517 (4)	0.01414 (10)
H1A	0.9336	0.5589	0.2894	0.017*
C2	1.11760 (6)	0.53229 (9)	0.32124 (4)	0.01548 (11)
C3	1.20321 (6)	0.46250 (9)	0.37595 (4)	0.01719 (11)
H3A	1.2907	0.4809	0.3723	0.021*
C4	1.15518 (6)	0.36706 (9)	0.43465 (4)	0.01614 (11)
H4A	1.2107	0.3226	0.4714	0.019*
C5	1.02224 (6)	0.33535 (8)	0.43995 (4)	0.01347 (10)
C6	0.93765 (6)	0.40614 (8)	0.38437 (3)	0.01243 (10)
C7	0.80451 (6)	0.36943 (8)	0.39077 (3)	0.01238 (10)
C8	0.76613 (6)	0.26872 (8)	0.45085 (3)	0.01334 (10)
C9	0.85868 (6)	0.20413 (9)	0.50445 (4)	0.01465 (10)
C10	0.70864 (6)	0.44156 (8)	0.33610 (3)	0.01260 (10)
C11	0.70861 (6)	0.39520 (9)	0.25902 (4)	0.01491 (10)
H11A	0.7714	0.3219	0.2410	0.018*
C12	0.61476 (6)	0.45857 (9)	0.20938 (4)	0.01612 (11)
H12A	0.6143	0.4263	0.1585	0.019*
C13	0.52150 (6)	0.57038 (9)	0.23602 (4)	0.01573 (11)
H13A	0.4589	0.6126	0.2029	0.019*
C14	0.52217 (6)	0.61880 (9)	0.31229 (4)	0.01545 (11)
H14A	0.4607	0.6947	0.3298	0.019*
C15	0.61476 (6)	0.55367 (9)	0.36233 (4)	0.01429 (10)
H15A	0.6141	0.5849	0.4133	0.017*
C16	0.81736 (8)	0.09262 (10)	0.56922 (4)	0.02031 (13)
H16B	0.8914	0.0471	0.5951	0.030*
H16C	0.7660	−0.0001	0.5499	0.030*
H16A	0.7683	0.1595	0.6041	0.030*
C17	0.62761 (6)	0.22144 (9)	0.46068 (4)	0.01645 (11)
C18	0.56993 (9)	0.09744 (14)	0.40461 (5)	0.02852 (17)
H18A	0.4785	0.1000	0.4083	0.043*
H18B	0.6004	−0.0162	0.4156	0.043*
H18C	0.5940	0.1292	0.3541	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.01532 (7)	0.02794 (10)	0.02141 (8)	−0.00307 (5)	0.00332 (5)	0.00537 (6)
O1	0.0226 (3)	0.0312 (3)	0.0242 (3)	0.0004 (2)	0.0103 (2)	−0.0010 (2)
N1	0.0162 (2)	0.0145 (2)	0.0153 (2)	0.00089 (17)	−0.00179 (17)	0.00089 (17)
C1	0.0122 (2)	0.0158 (2)	0.0145 (2)	0.00001 (19)	0.00039 (18)	0.00054 (19)
C2	0.0132 (2)	0.0166 (3)	0.0167 (2)	−0.00137 (19)	0.00138 (19)	0.0000 (2)
C3	0.0123 (2)	0.0174 (3)	0.0219 (3)	−0.0004 (2)	−0.0010 (2)	−0.0008 (2)
C4	0.0133 (2)	0.0153 (3)	0.0197 (3)	0.00069 (19)	−0.0032 (2)	−0.0008 (2)
C5	0.0136 (2)	0.0125 (2)	0.0143 (2)	0.00098 (18)	−0.00177 (18)	−0.00102 (18)
C6	0.0118 (2)	0.0130 (2)	0.0125 (2)	0.00046 (18)	−0.00022 (17)	−0.00075 (18)
C7	0.0121 (2)	0.0135 (2)	0.0115 (2)	0.00065 (17)	0.00041 (17)	−0.00052 (18)
C8	0.0136 (2)	0.0143 (2)	0.0122 (2)	0.00014 (18)	0.00090 (18)	−0.00009 (18)
C9	0.0168 (2)	0.0135 (2)	0.0136 (2)	0.00065 (19)	−0.00055 (19)	0.00067 (19)
C10	0.0108 (2)	0.0151 (2)	0.0119 (2)	−0.00022 (18)	0.00032 (17)	0.00094 (18)
C11	0.0140 (2)	0.0181 (3)	0.0127 (2)	0.0014 (2)	0.00037 (18)	−0.0009 (2)
C12	0.0151 (2)	0.0200 (3)	0.0132 (2)	−0.0002 (2)	−0.00113 (19)	0.0002 (2)
C13	0.0127 (2)	0.0181 (3)	0.0164 (2)	−0.00090 (19)	−0.00199 (19)	0.0024 (2)
C14	0.0116 (2)	0.0171 (3)	0.0176 (3)	0.00086 (19)	0.00059 (19)	0.0011 (2)
C15	0.0122 (2)	0.0171 (3)	0.0136 (2)	0.00082 (19)	0.00122 (18)	−0.00023 (19)
C16	0.0232 (3)	0.0199 (3)	0.0177 (3)	0.0000 (2)	0.0000 (2)	0.0065 (2)
C17	0.0150 (2)	0.0194 (3)	0.0150 (2)	−0.0010 (2)	0.00195 (19)	0.0031 (2)
C18	0.0256 (4)	0.0377 (5)	0.0222 (3)	−0.0151 (3)	0.0014 (3)	−0.0032 (3)

Cl1—C2	1.7401 (7)	C10—C15	1.3985 (9)
O1—C17	1.2146 (9)	C10—C11	1.4032 (9)
N1—C9	1.3181 (9)	C11—C12	1.3944 (9)
N1—C5	1.3701 (9)	C11—H11A	0.9300
C1—C2	1.3714 (9)	C12—C13	1.3949 (10)
C1—C6	1.4196 (9)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.3937 (10)
C2—C3	1.4137 (10)	C13—H13A	0.9300
C3—C4	1.3742 (10)	C14—C15	1.3947 (9)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.4173 (9)	C15—H15A	0.9300
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.4203 (9)	C16—H16C	0.9600
C6—C7	1.4284 (9)	C16—H16A	0.9600
C7—C8	1.3813 (9)	C17—C18	1.5012 (11)
C7—C10	1.4891 (9)	C18—H18A	0.9600
C8—C9	1.4325 (9)	C18—H18B	0.9600
C8—C17	1.5081 (9)	C18—H18C	0.9600
C9—C16	1.5021 (10)
C9—N1—C5	118.23 (6)	C12—C11—C10	120.24 (6)
C2—C1—C6	119.46 (6)	C12—C11—H11A	119.9
C2—C1—H1A	120.3	C10—C11—H11A	119.9
C6—C1—H1A	120.3	C11—C12—C13	120.03 (6)
C1—C2—C3	122.01 (6)	C11—C12—H12A	120.0
C1—C2—Cl1	119.39 (5)	C13—C12—H12A	120.0
C3—C2—Cl1	118.59 (5)	C14—C13—C12	119.97 (6)
C4—C3—C2	119.00 (6)	C14—C13—H13A	120.0
C4—C3—H3A	120.5	C12—C13—H13A	120.0
C2—C3—H3A	120.5	C13—C14—C15	120.14 (6)
C3—C4—C5	120.97 (6)	C13—C14—H14A	119.9
C3—C4—H4A	119.5	C15—C14—H14A	119.9
C5—C4—H4A	119.5	C14—C15—C10	120.25 (6)
N1—C5—C4	117.56 (6)	C14—C15—H15A	119.9
N1—C5—C6	123.19 (6)	C10—C15—H15A	119.9
C4—C5—C6	119.25 (6)	C9—C16—H16B	109.5
C1—C6—C5	119.27 (6)	C9—C16—H16C	109.5
C1—C6—C7	122.95 (6)	H16B—C16—H16C	109.5
C5—C6—C7	117.78 (6)	C9—C16—H16A	109.5
C8—C7—C6	118.01 (6)	H16B—C16—H16A	109.5
C8—C7—C10	120.53 (5)	H16C—C16—H16A	109.5
C6—C7—C10	121.43 (5)	O1—C17—C18	121.94 (7)
C7—C8—C9	120.13 (6)	O1—C17—C8	120.60 (7)
C7—C8—C17	121.19 (6)	C18—C17—C8	117.34 (6)
C9—C8—C17	118.67 (6)	C17—C18—H18A	109.5
N1—C9—C8	122.66 (6)	C17—C18—H18B	109.5
N1—C9—C16	117.12 (6)	H18A—C18—H18B	109.5
C8—C9—C16	120.21 (6)	C17—C18—H18C	109.5
C15—C10—C11	119.35 (6)	H18A—C18—H18C	109.5
C15—C10—C7	119.49 (5)	H18B—C18—H18C	109.5
C11—C10—C7	121.13 (6)
C6—C1—C2—C3	−2.09 (10)	C5—N1—C9—C8	0.38 (10)
C6—C1—C2—Cl1	179.09 (5)	C5—N1—C9—C16	179.18 (6)
C1—C2—C3—C4	0.36 (11)	C7—C8—C9—N1	−0.40 (10)
Cl1—C2—C3—C4	179.19 (5)	C17—C8—C9—N1	178.37 (6)
C2—C3—C4—C5	1.27 (10)	C7—C8—C9—C16	−179.17 (6)
C9—N1—C5—C4	−179.52 (6)	C17—C8—C9—C16	−0.40 (9)
C9—N1—C5—C6	0.11 (10)	C8—C7—C10—C15	61.18 (9)
C3—C4—C5—N1	178.51 (6)	C6—C7—C10—C15	−116.81 (7)
C3—C4—C5—C6	−1.13 (10)	C8—C7—C10—C11	−116.99 (7)
C2—C1—C6—C5	2.18 (10)	C6—C7—C10—C11	65.01 (9)
C2—C1—C6—C7	−177.46 (6)	C15—C10—C11—C12	−0.88 (10)
N1—C5—C6—C1	179.78 (6)	C7—C10—C11—C12	177.30 (6)
C4—C5—C6—C1	−0.60 (9)	C10—C11—C12—C13	0.91 (10)
N1—C5—C6—C7	−0.57 (9)	C11—C12—C13—C14	0.02 (10)
C4—C5—C6—C7	179.06 (6)	C12—C13—C14—C15	−0.97 (10)
C1—C6—C7—C8	−179.83 (6)	C13—C14—C15—C10	1.00 (10)
C5—C6—C7—C8	0.52 (9)	C11—C10—C15—C14	−0.07 (10)
C1—C6—C7—C10	−1.79 (10)	C7—C10—C15—C14	−178.28 (6)
C5—C6—C7—C10	178.56 (6)	C7—C8—C17—O1	−113.46 (8)
C6—C7—C8—C9	−0.08 (9)	C9—C8—C17—O1	67.78 (9)
C10—C7—C8—C9	−178.14 (6)	C7—C8—C17—C18	70.31 (9)
C6—C7—C8—C17	−178.81 (6)	C9—C8—C17—C18	−108.45 (8)
C10—C7—C8—C17	3.13 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1i	0.93	2.55	3.2047 (10)	128
C11—H11A···Cg1ii	0.93	2.78	3.6416 (7)	155
C13—H13A···Cg2iii	0.93	2.92	3.6255 (8)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1i	0.93	2.55	3.2047 (10)	128
C11—H11A⋯Cg1ii	0.93	2.78	3.6416 (7)	155
C13—H13A⋯Cg2iii	0.93	2.92	3.6255 (8)	133

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C9/N1 and C10–C15 ring systems, respectively.