1-[6-Chloro-4-(2-chloro-phen-yl)-2-methyl-3-quinol-yl]ethanone.

The title compound, C(18)H(13)Cl(2)NO, features an essentially planar quinoline ring system (r.m.s. deviation = 0.023 Å) with the acetyl [C-C-C-O torsion angle = -78.27 (17)°] and benzene [C-C-C-C torsion angle = 110.11 (14)°] substituents being twisted out of the plane; the dihedral angle formed between the mean planes of these two substituents is 58.01 (8)°. The acetyl O and benzene-bound Cl atoms lie to opposite sides of the mol-ecule. Centrosymmetric aggregates mediated by pairs of C-H⋯O contacts are found in the crystal structure, and these are connected into a two-dimensional array in the (01) plane via Cl⋯O [3.0508 (11) Å] inter-actions.

Related literature

For background to the pharmaceutical potential of quinoline derivatives, see: Musiol et al. (2006 ▶). For related structures, see: Kaiser et al. (2009 ▶); Viji et al. (2010 ▶). For a review on halogen bonding, including short halogen⋯oxygen inter­actions, see: Fourmigué (2009 ▶).

Experimental

Crystal data

C18H13Cl2NO

M = 330.22

Monoclinic,

a = 10.3105 (6) Å

b = 12.8882 (7) Å

c = 11.7968 (7) Å

β = 93.367 (1)°

V = 1564.90 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 100 K

0.29 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.933, T max = 1.000

14786 measured reflections

3594 independent reflections

3189 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.03

3594 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026991/lh5080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026991/lh5080Isup2.hkl

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

C18H13Cl2NO	F(000) = 680
Mr = 330.22	Dx = 1.402 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6804 reflections
a = 10.3105 (6) Å	θ = 2.3–28.2°
b = 12.8882 (7) Å	µ = 0.42 mm−1
c = 11.7968 (7) Å	T = 100 K
β = 93.367 (1)°	Block, colourless
V = 1564.90 (16) Å3	0.29 × 0.24 × 0.19 mm
Z = 4

Bruker SMART APEX diffractometer	3594 independent reflections
Radiation source: fine-focus sealed tube	3189 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.933, Tmax = 1.000	k = −16→16
14786 measured reflections	l = −15→15

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.6548P] where P = (Fo2 + 2Fc2)/3
3594 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	−0.23962 (3)	1.07600 (3)	0.72582 (3)	0.02312 (9)
Cl2	0.13655 (3)	0.82921 (3)	0.61673 (3)	0.02099 (9)
O1	0.46437 (10)	0.84047 (8)	1.00816 (9)	0.0300 (2)
N1	0.04450 (12)	0.78055 (9)	1.02995 (9)	0.0227 (2)
C1	0.17096 (14)	0.76859 (10)	1.02455 (11)	0.0212 (3)
C2	0.24419 (13)	0.82174 (10)	0.94326 (10)	0.0175 (3)
C3	0.18344 (12)	0.88978 (9)	0.86805 (10)	0.0150 (2)
C4	0.04755 (12)	0.90673 (9)	0.87489 (10)	0.0155 (2)
C5	−0.02314 (12)	0.97804 (10)	0.80428 (10)	0.0160 (2)
H5	0.0199	1.0186	0.7507	0.019*
C6	−0.15383 (12)	0.98816 (10)	0.81377 (10)	0.0179 (3)
C7	−0.22160 (13)	0.92969 (11)	0.89191 (11)	0.0224 (3)
H7	−0.3128	0.9374	0.8959	0.027*
C8	−0.15385 (14)	0.86143 (11)	0.96212 (11)	0.0234 (3)
H8	−0.1987	0.8220	1.0155	0.028*
C9	−0.01808 (13)	0.84880 (10)	0.95623 (10)	0.0187 (3)
C10	0.23720 (17)	0.69329 (11)	1.10655 (12)	0.0294 (3)
H10A	0.1717	0.6565	1.1481	0.044*
H10B	0.2957	0.7312	1.1604	0.044*
H10C	0.2874	0.6432	1.0646	0.044*
C11	0.38793 (14)	0.80115 (10)	0.93929 (11)	0.0209 (3)
C12	0.42837 (16)	0.72882 (13)	0.84825 (13)	0.0326 (4)
H12A	0.5219	0.7157	0.8584	0.049*
H12B	0.4085	0.7603	0.7736	0.049*
H12C	0.3811	0.6632	0.8532	0.049*
C13	0.25864 (12)	0.94625 (10)	0.78298 (10)	0.0148 (2)
C14	0.24475 (12)	0.92459 (10)	0.66698 (10)	0.0159 (2)
C15	0.31894 (13)	0.97515 (10)	0.58914 (11)	0.0197 (3)
H15	0.3091	0.9584	0.5107	0.024*
C16	0.40740 (13)	1.05034 (11)	0.62726 (11)	0.0208 (3)
H16	0.4582	1.0855	0.5747	0.025*
C17	0.42194 (13)	1.07433 (10)	0.74183 (12)	0.0200 (3)
H17	0.4818	1.1265	0.7675	0.024*
C18	0.34908 (12)	1.02213 (10)	0.81890 (11)	0.0173 (3)
H18	0.3608	1.0382	0.8974	0.021*

	U11	U22	U33	U12	U13	U23
Cl1	0.01579 (16)	0.03008 (18)	0.02304 (17)	0.00616 (12)	−0.00267 (12)	−0.00421 (13)
Cl2	0.02021 (17)	0.02349 (17)	0.01915 (15)	−0.00465 (12)	0.00013 (12)	−0.00655 (12)
O1	0.0281 (6)	0.0284 (5)	0.0319 (5)	0.0051 (4)	−0.0132 (4)	−0.0042 (4)
N1	0.0347 (7)	0.0172 (5)	0.0166 (5)	−0.0016 (5)	0.0055 (5)	0.0005 (4)
C1	0.0338 (8)	0.0147 (6)	0.0150 (6)	0.0018 (5)	−0.0001 (5)	−0.0009 (5)
C2	0.0224 (7)	0.0147 (6)	0.0152 (6)	0.0014 (5)	−0.0015 (5)	−0.0043 (5)
C3	0.0174 (6)	0.0141 (5)	0.0133 (5)	−0.0003 (5)	0.0004 (4)	−0.0027 (4)
C4	0.0173 (6)	0.0146 (6)	0.0148 (5)	−0.0012 (5)	0.0015 (5)	−0.0031 (4)
C5	0.0158 (6)	0.0169 (6)	0.0157 (6)	−0.0009 (5)	0.0028 (4)	−0.0017 (5)
C6	0.0163 (6)	0.0211 (6)	0.0159 (6)	0.0010 (5)	−0.0009 (5)	−0.0056 (5)
C7	0.0155 (6)	0.0306 (7)	0.0217 (6)	−0.0043 (5)	0.0059 (5)	−0.0076 (5)
C8	0.0248 (7)	0.0261 (7)	0.0204 (6)	−0.0070 (6)	0.0097 (5)	−0.0034 (5)
C9	0.0246 (7)	0.0162 (6)	0.0157 (6)	−0.0026 (5)	0.0045 (5)	−0.0029 (5)
C10	0.0456 (9)	0.0204 (7)	0.0217 (7)	0.0052 (6)	−0.0018 (6)	0.0041 (5)
C11	0.0242 (7)	0.0172 (6)	0.0207 (6)	0.0055 (5)	−0.0039 (5)	0.0016 (5)
C12	0.0279 (8)	0.0373 (9)	0.0320 (8)	0.0138 (7)	−0.0028 (6)	−0.0102 (7)
C13	0.0122 (6)	0.0159 (6)	0.0163 (6)	0.0035 (4)	0.0007 (4)	−0.0002 (4)
C14	0.0138 (6)	0.0163 (6)	0.0174 (6)	0.0010 (5)	−0.0009 (5)	−0.0028 (5)
C15	0.0192 (6)	0.0242 (7)	0.0160 (6)	0.0026 (5)	0.0021 (5)	−0.0002 (5)
C16	0.0174 (6)	0.0223 (7)	0.0232 (6)	0.0006 (5)	0.0058 (5)	0.0027 (5)
C17	0.0138 (6)	0.0194 (6)	0.0270 (7)	−0.0009 (5)	0.0021 (5)	−0.0031 (5)
C18	0.0142 (6)	0.0194 (6)	0.0181 (6)	0.0019 (5)	−0.0005 (5)	−0.0031 (5)

Cl1—C6	1.7415 (14)	C8—H8	0.9500
Cl2—C14	1.7405 (13)	C10—H10A	0.9800
O1—C11	1.2095 (17)	C10—H10B	0.9800
N1—C1	1.3181 (19)	C10—H10C	0.9800
N1—C9	1.3713 (17)	C11—C12	1.4996 (19)
C1—C2	1.4297 (18)	C12—H12A	0.9800
C1—C10	1.5055 (19)	C12—H12B	0.9800
C2—C3	1.3722 (17)	C12—H12C	0.9800
C2—C11	1.5091 (19)	C13—C14	1.3956 (17)
C3—C4	1.4250 (17)	C13—C18	1.3997 (18)
C3—C13	1.4932 (17)	C14—C15	1.3912 (18)
C4—C5	1.4137 (17)	C15—C16	1.3874 (19)
C4—C9	1.4186 (17)	C15—H15	0.9500
C5—C6	1.3649 (17)	C16—C17	1.3860 (19)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.4077 (18)	C17—C18	1.3871 (18)
C7—C8	1.371 (2)	C17—H17	0.9500
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.4150 (19)
C1—N1—C9	118.31 (11)	C1—C10—H10C	109.5
N1—C1—C2	122.63 (12)	H10A—C10—H10C	109.5
N1—C1—C10	117.20 (13)	H10B—C10—H10C	109.5
C2—C1—C10	120.16 (13)	O1—C11—C12	122.95 (13)
C3—C2—C1	120.06 (12)	O1—C11—C2	120.52 (12)
C3—C2—C11	120.27 (12)	C12—C11—C2	116.51 (12)
C1—C2—C11	119.66 (11)	C11—C12—H12A	109.5
C2—C3—C4	118.32 (11)	C11—C12—H12B	109.5
C2—C3—C13	120.71 (11)	H12A—C12—H12B	109.5
C4—C3—C13	120.96 (11)	C11—C12—H12C	109.5
C5—C4—C9	119.40 (12)	H12A—C12—H12C	109.5
C5—C4—C3	122.74 (11)	H12B—C12—H12C	109.5
C9—C4—C3	117.86 (11)	C14—C13—C18	117.70 (11)
C6—C5—C4	119.41 (12)	C14—C13—C3	122.28 (11)
C6—C5—H5	120.3	C18—C13—C3	120.00 (11)
C4—C5—H5	120.3	C15—C14—C13	121.65 (12)
C5—C6—C7	122.21 (12)	C15—C14—Cl2	118.18 (10)
C5—C6—Cl1	118.85 (10)	C13—C14—Cl2	120.13 (10)
C7—C6—Cl1	118.94 (10)	C16—C15—C14	119.32 (12)
C8—C7—C6	118.96 (12)	C16—C15—H15	120.3
C8—C7—H7	120.5	C14—C15—H15	120.3
C6—C7—H7	120.5	C17—C16—C15	120.22 (12)
C7—C8—C9	120.97 (12)	C17—C16—H16	119.9
C7—C8—H8	119.5	C15—C16—H16	119.9
C9—C8—H8	119.5	C16—C17—C18	119.95 (12)
N1—C9—C8	118.21 (12)	C16—C17—H17	120.0
N1—C9—C4	122.76 (12)	C18—C17—H17	120.0
C8—C9—C4	119.03 (12)	C17—C18—C13	121.15 (12)
C1—C10—H10A	109.5	C17—C18—H18	119.4
C1—C10—H10B	109.5	C13—C18—H18	119.4
H10A—C10—H10B	109.5
C9—N1—C1—C2	−1.68 (19)	C7—C8—C9—C4	−1.06 (19)
C9—N1—C1—C10	179.92 (11)	C5—C4—C9—N1	−178.00 (11)
N1—C1—C2—C3	1.17 (19)	C3—C4—C9—N1	2.15 (18)
C10—C1—C2—C3	179.53 (12)	C5—C4—C9—C8	2.05 (18)
N1—C1—C2—C11	−177.73 (12)	C3—C4—C9—C8	−177.80 (11)
C10—C1—C2—C11	0.63 (18)	C3—C2—C11—O1	102.83 (15)
C1—C2—C3—C4	1.04 (17)	C1—C2—C11—O1	−78.27 (17)
C11—C2—C3—C4	179.94 (11)	C3—C2—C11—C12	−78.41 (16)
C1—C2—C3—C13	179.73 (11)	C1—C2—C11—C12	100.49 (15)
C11—C2—C3—C13	−1.37 (18)	C2—C3—C13—C14	110.11 (14)
C2—C3—C4—C5	177.58 (11)	C4—C3—C13—C14	−71.23 (16)
C13—C3—C4—C5	−1.11 (18)	C2—C3—C13—C18	−68.30 (16)
C2—C3—C4—C9	−2.57 (17)	C4—C3—C13—C18	110.35 (14)
C13—C3—C4—C9	178.74 (11)	C18—C13—C14—C15	0.86 (18)
C9—C4—C5—C6	−1.52 (18)	C3—C13—C14—C15	−177.59 (12)
C3—C4—C5—C6	178.33 (11)	C18—C13—C14—Cl2	178.64 (9)
C4—C5—C6—C7	−0.03 (19)	C3—C13—C14—Cl2	0.19 (17)
C4—C5—C6—Cl1	−179.77 (9)	C13—C14—C15—C16	−1.16 (19)
C5—C6—C7—C8	1.0 (2)	Cl2—C14—C15—C16	−178.98 (10)
Cl1—C6—C7—C8	−179.22 (10)	C14—C15—C16—C17	0.3 (2)
C6—C7—C8—C9	−0.5 (2)	C15—C16—C17—C18	0.8 (2)
C1—N1—C9—C8	179.94 (12)	C16—C17—C18—C13	−1.13 (19)
C1—N1—C9—C4	−0.02 (19)	C14—C13—C18—C17	0.29 (18)
C7—C8—C9—N1	178.98 (12)	C3—C13—C18—C17	178.78 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1i	0.95	2.59	3.2460 (17)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1i	0.95	2.59	3.2460 (17)	127

Symmetry code: (i) .