3-Acetyl-6-chloro-1-ethyl-4-phenyl-quinolin-2(1H)-one.

In the title compound, C(19)H(16)ClNO(2), the dihedral angle between the plane of the phenyl substituent and 3-acetyl-quinoline unit is 75.44 (5)°. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to isoquinolines, see: Broadhurst et al. (2001 ▶); Behrens (1999 ▶); Broadhurst (1991 ▶); Chao et al. (1999 ▶); Cobet & Luckner (1971 ▶); Kametani (1968 ▶); Lamberton & Price (1953 ▶); Majumdar & Mukhopadhyay (2003 ▶); Nayar et al. (1971 ▶); Storer et al. (1973 ▶); Yong et al. (2001 ▶). For related crystal structures, see: Yang et al. (2008 ▶); Choudhury & Guru Row (2006 ▶); Choudhury et al. (2002 ▶); Hathwar et al. (2008 ▶); Cho et al. (2002 ▶); Manivel et al. (2009 ▶).

Experimental

Crystal data

C19H16ClNO2

M = 325.78

Monoclinic,

a = 9.6480 (8) Å

b = 17.5756 (11) Å

c = 9.9694 (7) Å

β = 103.245 (8)°

V = 1645.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 290 K

0.21 × 0.16 × 0.15 mm

Data collection

Oxford Xcalibur Eos(Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlisPro RED; Oxford Diffraction, 2009 ▶) T min = 0.925, T max = 0.965

21440 measured reflections

3061 independent reflections

1928 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 0.95

3061 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlisPro CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro CCD; data reduction: CrysAlisPro RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024830/bt2983sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024830/bt2983Isup2.hkl

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

C19H16ClNO2	F(000) = 680
Mr = 325.78	Dx = 1.315 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1023 reflections
a = 9.6480 (8) Å	θ = 1.7–20.6°
b = 17.5756 (11) Å	µ = 0.24 mm−1
c = 9.9694 (7) Å	T = 290 K
β = 103.245 (8)°	Block, colorless
V = 1645.5 (2) Å3	0.21 × 0.16 × 0.15 mm
Z = 4

Oxford Xcalibur Eos(Nova) CCD detector diffractometer	3061 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1928 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.925, Tmax = 0.965	k = −21→21
21440 measured reflections	l = −12→12

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) = 0.106	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0592P)2] where P = (Fo2 + 2Fc2)/3
3061 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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	0.51092 (6)	1.05067 (3)	0.20536 (6)	0.0782 (2)
N1	0.35571 (15)	0.79959 (8)	0.53674 (14)	0.0523 (4)
O1	0.18412 (15)	0.72734 (8)	0.59753 (16)	0.0844 (5)
O2	−0.11779 (16)	0.83560 (9)	0.49385 (18)	0.0873 (5)
C1	0.2157 (2)	0.78011 (11)	0.52883 (19)	0.0562 (5)
C2	0.10651 (18)	0.82606 (9)	0.43889 (18)	0.0488 (4)
C3	0.13896 (17)	0.88600 (9)	0.36740 (17)	0.0448 (4)
C4	0.32709 (19)	0.96195 (10)	0.29747 (17)	0.0502 (4)
H4	0.2572	0.9916	0.2416	0.060*
C5	0.46684 (19)	0.97641 (10)	0.30238 (18)	0.0527 (5)
C6	0.5726 (2)	0.93221 (11)	0.38284 (19)	0.0585 (5)
H6	0.6677	0.9419	0.3845	0.070*
C7	0.53689 (19)	0.87387 (10)	0.46042 (18)	0.0554 (5)
H7	0.6083	0.8443	0.5145	0.066*
C8	0.39405 (18)	0.85855 (9)	0.45869 (17)	0.0467 (4)
C9	0.28714 (17)	0.90307 (9)	0.37541 (16)	0.0434 (4)
C10	0.02678 (17)	0.93280 (9)	0.27678 (17)	0.0460 (4)
C11	−0.0010 (2)	1.00621 (10)	0.3121 (2)	0.0602 (5)
H11	0.0483	1.0266	0.3956	0.072*
C12	−0.1019 (2)	1.04958 (11)	0.2237 (2)	0.0705 (6)
H12	−0.1209	1.0988	0.2485	0.085*
C13	−0.1740 (2)	1.02063 (13)	0.1000 (2)	0.0743 (6)
H13	−0.2407	1.0503	0.0402	0.089*
C14	−0.1473 (2)	0.94779 (13)	0.0647 (2)	0.0736 (6)
H14	−0.1972	0.9276	−0.0186	0.088*
C15	−0.0470 (2)	0.90426 (11)	0.15166 (19)	0.0607 (5)
H15	−0.0287	0.8551	0.1260	0.073*
C16	−0.0442 (2)	0.80120 (11)	0.4330 (2)	0.0571 (5)
C17	−0.0962 (2)	0.73258 (12)	0.3491 (2)	0.0816 (7)
H17A	−0.1914	0.7210	0.3567	0.122*
H17B	−0.0350	0.6903	0.3820	0.122*
H17C	−0.0960	0.7422	0.2543	0.122*
C18	0.4651 (2)	0.75412 (11)	0.6307 (2)	0.0636 (5)
H18A	0.4254	0.7340	0.7044	0.076*
H18B	0.5445	0.7868	0.6718	0.076*
C19	0.5185 (3)	0.68935 (11)	0.5580 (3)	0.0872 (7)
H19A	0.4404	0.6567	0.5174	0.131*
H19B	0.5880	0.6609	0.6231	0.131*
H19C	0.5613	0.7091	0.4873	0.131*

	U11	U22	U33	U12	U13	U23
Cl1	0.0683 (4)	0.0909 (4)	0.0817 (4)	−0.0115 (3)	0.0305 (3)	0.0206 (3)
N1	0.0456 (9)	0.0560 (9)	0.0506 (9)	0.0030 (7)	0.0012 (7)	0.0075 (7)
O1	0.0660 (10)	0.0864 (10)	0.0946 (11)	−0.0072 (8)	0.0056 (8)	0.0460 (9)
O2	0.0636 (10)	0.0908 (11)	0.1172 (13)	−0.0045 (8)	0.0406 (10)	−0.0133 (9)
C1	0.0508 (12)	0.0585 (12)	0.0568 (11)	−0.0002 (9)	0.0069 (9)	0.0104 (10)
C2	0.0433 (10)	0.0521 (10)	0.0504 (10)	−0.0007 (8)	0.0093 (8)	0.0018 (9)
C3	0.0434 (10)	0.0505 (10)	0.0398 (9)	0.0019 (8)	0.0081 (8)	0.0000 (8)
C4	0.0457 (11)	0.0591 (11)	0.0457 (10)	0.0028 (9)	0.0105 (8)	0.0031 (9)
C5	0.0511 (12)	0.0613 (11)	0.0480 (10)	−0.0042 (9)	0.0158 (9)	−0.0025 (9)
C6	0.0423 (11)	0.0728 (13)	0.0604 (12)	−0.0048 (10)	0.0115 (9)	−0.0070 (10)
C7	0.0426 (11)	0.0650 (12)	0.0545 (11)	0.0032 (9)	0.0030 (9)	−0.0006 (10)
C8	0.0463 (11)	0.0486 (10)	0.0435 (10)	−0.0001 (8)	0.0070 (8)	−0.0025 (8)
C9	0.0419 (10)	0.0467 (10)	0.0407 (9)	0.0003 (8)	0.0076 (8)	−0.0009 (8)
C10	0.0394 (10)	0.0529 (11)	0.0475 (10)	0.0041 (8)	0.0138 (8)	0.0063 (8)
C11	0.0623 (13)	0.0567 (12)	0.0617 (12)	0.0062 (10)	0.0146 (10)	−0.0015 (10)
C12	0.0735 (15)	0.0572 (12)	0.0872 (16)	0.0202 (11)	0.0316 (13)	0.0094 (12)
C13	0.0627 (14)	0.0896 (16)	0.0722 (15)	0.0289 (12)	0.0186 (12)	0.0254 (13)
C14	0.0675 (14)	0.0857 (15)	0.0602 (13)	0.0178 (12)	−0.0003 (11)	0.0037 (12)
C15	0.0607 (13)	0.0625 (12)	0.0547 (12)	0.0122 (10)	0.0045 (10)	0.0005 (10)
C16	0.0507 (12)	0.0596 (12)	0.0593 (12)	−0.0019 (10)	0.0093 (10)	0.0124 (10)
C17	0.0712 (15)	0.0829 (15)	0.0854 (16)	−0.0190 (12)	0.0067 (12)	−0.0039 (13)
C18	0.0598 (13)	0.0666 (13)	0.0579 (12)	0.0084 (10)	0.0002 (10)	0.0159 (10)
C19	0.0915 (17)	0.0672 (14)	0.1005 (18)	0.0208 (12)	0.0172 (14)	0.0104 (13)

Cl1—C5	1.7344 (18)	C10—C15	1.381 (2)
N1—C1	1.378 (2)	C11—C12	1.383 (3)
N1—C8	1.396 (2)	C11—H11	0.9300
N1—C18	1.476 (2)	C12—C13	1.368 (3)
O1—C1	1.232 (2)	C12—H12	0.9300
O2—C16	1.198 (2)	C13—C14	1.368 (3)
C1—C2	1.460 (2)	C13—H13	0.9300
C2—C3	1.348 (2)	C14—C15	1.374 (3)
C2—C16	1.507 (2)	C14—H14	0.9300
C3—C9	1.445 (2)	C15—H15	0.9300
C3—C10	1.489 (2)	C16—C17	1.488 (3)
C4—C5	1.362 (2)	C17—H17A	0.9600
C4—C9	1.400 (2)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.383 (3)	C18—C19	1.502 (3)
C6—C7	1.375 (2)	C18—H18A	0.9700
C6—H6	0.9300	C18—H18B	0.9700
C7—C8	1.400 (2)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C9	1.405 (2)	C19—H19C	0.9600
C10—C11	1.380 (2)
C1—N1—C8	122.28 (14)	C12—C11—H11	119.9
C1—N1—C18	116.83 (15)	C13—C12—C11	120.54 (19)
C8—N1—C18	120.89 (15)	C13—C12—H12	119.7
O1—C1—N1	121.27 (17)	C11—C12—H12	119.7
O1—C1—C2	121.48 (17)	C12—C13—C14	119.54 (19)
N1—C1—C2	117.22 (16)	C12—C13—H13	120.2
C3—C2—C1	122.30 (16)	C14—C13—H13	120.2
C3—C2—C16	123.02 (16)	C13—C14—C15	120.4 (2)
C1—C2—C16	114.68 (15)	C13—C14—H14	119.8
C2—C3—C9	118.67 (15)	C15—C14—H14	119.8
C2—C3—C10	121.86 (15)	C14—C15—C10	120.67 (18)
C9—C3—C10	119.42 (14)	C14—C15—H15	119.7
C5—C4—C9	120.94 (17)	C10—C15—H15	119.7
C5—C4—H4	119.5	O2—C16—C17	122.09 (19)
C9—C4—H4	119.5	O2—C16—C2	120.83 (18)
C4—C5—C6	120.58 (17)	C17—C16—C2	117.08 (18)
C4—C5—Cl1	119.19 (15)	C16—C17—H17A	109.5
C6—C5—Cl1	120.23 (14)	C16—C17—H17B	109.5
C7—C6—C5	119.91 (17)	H17A—C17—H17B	109.5
C7—C6—H6	120.0	C16—C17—H17C	109.5
C5—C6—H6	120.0	H17A—C17—H17C	109.5
C6—C7—C8	120.60 (17)	H17B—C17—H17C	109.5
C6—C7—H7	119.7	N1—C18—C19	112.27 (16)
C8—C7—H7	119.7	N1—C18—H18A	109.2
N1—C8—C7	121.44 (16)	C19—C18—H18A	109.2
N1—C8—C9	119.38 (15)	N1—C18—H18B	109.2
C7—C8—C9	119.17 (16)	C19—C18—H18B	109.2
C4—C9—C8	118.78 (16)	H18A—C18—H18B	107.9
C4—C9—C3	121.17 (15)	C18—C19—H19A	109.5
C8—C9—C3	120.01 (15)	C18—C19—H19B	109.5
C11—C10—C15	118.71 (16)	H19A—C19—H19B	109.5
C11—C10—C3	121.22 (16)	C18—C19—H19C	109.5
C15—C10—C3	120.00 (15)	H19A—C19—H19C	109.5
C10—C11—C12	120.13 (18)	H19B—C19—H19C	109.5
C10—C11—H11	119.9
C8—N1—C1—O1	179.22 (17)	C7—C8—C9—C4	−0.6 (2)
C18—N1—C1—O1	0.2 (3)	N1—C8—C9—C3	−2.1 (2)
C8—N1—C1—C2	−2.6 (2)	C7—C8—C9—C3	177.21 (15)
C18—N1—C1—C2	178.42 (15)	C2—C3—C9—C4	176.41 (16)
O1—C1—C2—C3	177.17 (18)	C10—C3—C9—C4	−1.2 (2)
N1—C1—C2—C3	−1.0 (3)	C2—C3—C9—C8	−1.3 (2)
O1—C1—C2—C16	−2.7 (3)	C10—C3—C9—C8	−178.92 (15)
N1—C1—C2—C16	179.10 (16)	C2—C3—C10—C11	109.3 (2)
C1—C2—C3—C9	2.9 (2)	C9—C3—C10—C11	−73.2 (2)
C16—C2—C3—C9	−177.26 (15)	C2—C3—C10—C15	−73.9 (2)
C1—C2—C3—C10	−179.55 (16)	C9—C3—C10—C15	103.69 (19)
C16—C2—C3—C10	0.3 (3)	C15—C10—C11—C12	0.6 (3)
C9—C4—C5—C6	1.2 (3)	C3—C10—C11—C12	177.48 (16)
C9—C4—C5—Cl1	−179.29 (13)	C10—C11—C12—C13	−0.7 (3)
C4—C5—C6—C7	−1.0 (3)	C11—C12—C13—C14	1.0 (3)
Cl1—C5—C6—C7	179.43 (13)	C12—C13—C14—C15	−1.1 (3)
C5—C6—C7—C8	0.1 (3)	C13—C14—C15—C10	1.0 (3)
C1—N1—C8—C7	−175.20 (16)	C11—C10—C15—C14	−0.7 (3)
C18—N1—C8—C7	3.8 (2)	C3—C10—C15—C14	−177.66 (17)
C1—N1—C8—C9	4.1 (2)	C3—C2—C16—O2	−76.4 (2)
C18—N1—C8—C9	−176.91 (16)	C1—C2—C16—O2	103.5 (2)
C6—C7—C8—N1	−179.99 (15)	C3—C2—C16—C17	103.7 (2)
C6—C7—C8—C9	0.7 (3)	C1—C2—C16—C17	−76.4 (2)
C5—C4—C9—C8	−0.4 (2)	C1—N1—C18—C19	93.7 (2)
C5—C4—C9—C3	−178.10 (16)	C8—N1—C18—C19	−85.3 (2)
N1—C8—C9—C4	−179.89 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.58	3.341 (2)	139
C7—H7···O2ii	0.93	2.70	3.340 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.58	3.341 (2)	139
C7—H7⋯O2ii	0.93	2.70	3.340 (2)	126

Symmetry codes: (i) ; (ii) .