2-(4-Chloro-phen-yl)-2,3-di-hydro-quinolin-4(1H)-one.

The title mol-ecule, C15H12ClNO, features a di-hydro-quinolin-4(1H)-one moiety attached to a chloro-benzene ring. The heterocyclic ring has a half-chair conformation with the methine C atom lying 0.574 (3) Å above the plane of the five remaining atoms (r.m.s. deviation = 0.0240 Å). The dihedral angles between the terminal benzene rings is 77.53 (9)°, indicating a significant twist in the mol-ecule. In the crystal, supra-molecular zigzag chains along the c-axis direction are sustained by N-H⋯O hydrogen bonds. These are connected into double chains by C-H⋯π inter-actions.

Related literature

For background to and chemical reactivity of quinolone heterocycles, see: Diesbach & Kramer (1945 ▶); Prakash et al. (1994 ▶); Singh & Kapil (1993 ▶); Kalinin et al. (1992 ▶); Chauvin & Olivier (1996 ▶). For related structures, see: Bouraiou et al. (2008 ▶, 2011 ▶); Benzerka et al. (2011 ▶); Chelghoum et al. (2012 ▶).

Experimental

Crystal data

C15H12ClNO

M = 257.71

Monoclinic,

a = 17.703 (2) Å

b = 10.7537 (17) Å

c = 13.658 (2) Å

β = 105.486 (6)°

V = 2505.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 150 K

0.17 × 0.12 × 0.06 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.932, T max = 0.983

15688 measured reflections

2852 independent reflections

2314 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.107

S = 1.08

2852 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001548/tk5289sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001548/tk5289Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001548/tk5289Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H12ClNO	F(000) = 1072
Mr = 257.71	Dx = 1.366 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5286 reflections
a = 17.703 (2) Å	θ = 2.4–27.2°
b = 10.7537 (17) Å	µ = 0.29 mm−1
c = 13.658 (2) Å	T = 150 K
β = 105.486 (6)°	Prism, colourless
V = 2505.8 (6) Å3	0.17 × 0.12 × 0.06 mm
Z = 8

Bruker APEXII diffractometer	2314 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −22→21
Tmin = 0.932, Tmax = 0.983	k = −13→13
15688 measured reflections	l = −16→17
2852 independent reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0328P)2 + 4.0966P] where P = (Fo2 + 2Fc2)/3
2852 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.39 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
C1	0.14660 (10)	1.07351 (16)	0.61189 (13)	0.0207 (4)
C2	0.17699 (11)	1.17882 (17)	0.57430 (14)	0.0245 (4)
H2	0.1876	1.1752	0.5112	0.029*
C3	0.19115 (11)	1.28710 (18)	0.63005 (15)	0.0281 (4)
H3	0.2118	1.3555	0.6044	0.034*
C4	0.17487 (12)	1.29588 (18)	0.72502 (15)	0.0307 (4)
H4	0.1839	1.3697	0.7618	0.037*
C5	0.14538 (11)	1.19394 (18)	0.76280 (14)	0.0283 (4)
H5	0.1343	1.1994	0.8255	0.034*
C6	0.13150 (10)	1.08117 (16)	0.70848 (13)	0.0225 (4)
C7	0.10478 (11)	0.97037 (18)	0.75251 (13)	0.0271 (4)
C8	0.09756 (12)	0.85216 (18)	0.69154 (13)	0.0282 (4)
H8A	0.0563	0.8016	0.7056	0.034*
H8B	0.1462	0.806	0.7138	0.034*
C9	0.07953 (11)	0.87276 (17)	0.57716 (13)	0.0256 (4)
H9	0.0258	0.904	0.5523	0.031*
C10	0.08698 (11)	0.75256 (16)	0.52145 (13)	0.0241 (4)
C11	0.02108 (12)	0.69804 (18)	0.45834 (15)	0.0315 (4)
H11	−0.0276	0.7351	0.4508	0.038*
C12	0.02618 (12)	0.58890 (19)	0.40597 (16)	0.0329 (5)
H12	−0.0186	0.5527	0.364	0.04*
C13	0.09869 (11)	0.53526 (16)	0.41728 (14)	0.0264 (4)
C14	0.16620 (11)	0.58739 (18)	0.47938 (14)	0.0277 (4)
H14	0.2148	0.5505	0.4858	0.033*
C15	0.15978 (11)	0.69599 (18)	0.53192 (14)	0.0274 (4)
H15	0.2045	0.7314	0.5746	0.033*
N1	0.13339 (9)	0.96526 (14)	0.55585 (11)	0.0224 (3)
H1N	0.1307 (12)	0.9735 (19)	0.4941 (16)	0.027*
O1	0.09352 (10)	0.96926 (14)	0.83773 (10)	0.0422 (4)
Cl1	0.10656 (4)	0.39956 (5)	0.35097 (4)	0.04532 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0211 (8)	0.0223 (9)	0.0191 (8)	0.0041 (7)	0.0061 (7)	0.0013 (7)
C2	0.0264 (9)	0.0259 (9)	0.0238 (9)	0.0020 (7)	0.0112 (7)	0.0023 (7)
C3	0.0274 (10)	0.0244 (9)	0.0338 (10)	−0.0023 (8)	0.0103 (8)	0.0022 (8)
C4	0.0348 (11)	0.0257 (10)	0.0300 (10)	−0.0025 (8)	0.0060 (8)	−0.0080 (8)
C5	0.0340 (11)	0.0308 (10)	0.0197 (9)	−0.0009 (8)	0.0068 (8)	−0.0045 (7)
C6	0.0258 (9)	0.0243 (9)	0.0168 (8)	0.0013 (7)	0.0048 (7)	−0.0003 (7)
C7	0.0368 (11)	0.0291 (10)	0.0161 (8)	−0.0002 (8)	0.0083 (7)	0.0010 (7)
C8	0.0415 (11)	0.0256 (9)	0.0203 (9)	−0.0012 (8)	0.0133 (8)	0.0025 (7)
C9	0.0315 (10)	0.0250 (9)	0.0224 (9)	0.0014 (7)	0.0106 (7)	0.0013 (7)
C10	0.0345 (10)	0.0206 (9)	0.0210 (8)	0.0002 (7)	0.0142 (7)	0.0013 (7)
C11	0.0282 (10)	0.0289 (10)	0.0377 (11)	0.0059 (8)	0.0092 (8)	−0.0023 (8)
C12	0.0286 (10)	0.0291 (10)	0.0370 (11)	0.0013 (8)	0.0017 (8)	−0.0054 (8)
C13	0.0367 (10)	0.0182 (9)	0.0253 (9)	0.0036 (7)	0.0098 (8)	−0.0026 (7)
C14	0.0260 (9)	0.0271 (10)	0.0305 (10)	0.0054 (8)	0.0085 (8)	0.0040 (8)
C15	0.0272 (10)	0.0296 (10)	0.0244 (9)	−0.0061 (8)	0.0049 (7)	−0.0003 (7)
N1	0.0332 (8)	0.0215 (8)	0.0154 (7)	0.0008 (6)	0.0118 (6)	0.0012 (6)
O1	0.0737 (11)	0.0384 (8)	0.0198 (7)	−0.0086 (8)	0.0219 (7)	−0.0018 (6)
Cl1	0.0608 (4)	0.0271 (3)	0.0468 (3)	0.0075 (2)	0.0122 (3)	−0.0135 (2)

C1—N1	1.378 (2)	C8—H8B	0.97
C1—C2	1.408 (2)	C9—N1	1.460 (2)
C1—C6	1.417 (2)	C9—C10	1.523 (2)
C2—C3	1.377 (3)	C9—H9	0.98
C2—H2	0.93	C10—C11	1.382 (3)
C3—C4	1.405 (3)	C10—C15	1.398 (3)
C3—H3	0.93	C11—C12	1.390 (3)
C4—C5	1.373 (3)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.378 (3)
C5—C6	1.409 (2)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.386 (3)
C6—C7	1.469 (3)	C13—Cl1	1.7425 (18)
C7—O1	1.232 (2)	C14—C15	1.391 (3)
C7—C8	1.506 (3)	C14—H14	0.93
C8—C9	1.525 (2)	C15—H15	0.93
C8—H8A	0.97	N1—H1N	0.84 (2)
N1—C1—C2	120.10 (15)	N1—C9—C10	109.29 (14)
N1—C1—C6	121.33 (15)	N1—C9—C8	109.52 (15)
C2—C1—C6	118.56 (16)	C10—C9—C8	111.48 (15)
C3—C2—C1	120.62 (16)	N1—C9—H9	108.8
C3—C2—H2	119.7	C10—C9—H9	108.8
C1—C2—H2	119.7	C8—C9—H9	108.8
C2—C3—C4	121.02 (17)	C11—C10—C15	118.75 (17)
C2—C3—H3	119.5	C11—C10—C9	120.02 (17)
C4—C3—H3	119.5	C15—C10—C9	121.23 (17)
C5—C4—C3	119.06 (17)	C10—C11—C12	121.28 (18)
C5—C4—H4	120.5	C10—C11—H11	119.4
C3—C4—H4	120.5	C12—C11—H11	119.4
C4—C5—C6	121.32 (17)	C13—C12—C11	118.85 (18)
C4—C5—H5	119.3	C13—C12—H12	120.6
C6—C5—H5	119.3	C11—C12—H12	120.6
C5—C6—C1	119.40 (16)	C12—C13—C14	121.64 (17)
C5—C6—C7	120.84 (16)	C12—C13—Cl1	119.59 (15)
C1—C6—C7	119.71 (16)	C14—C13—Cl1	118.77 (15)
O1—C7—C6	123.07 (17)	C13—C14—C15	118.64 (17)
O1—C7—C8	120.19 (17)	C13—C14—H14	120.7
C6—C7—C8	116.57 (15)	C15—C14—H14	120.7
C7—C8—C9	114.05 (15)	C14—C15—C10	120.85 (17)
C7—C8—H8A	108.7	C14—C15—H15	119.6
C9—C8—H8A	108.7	C10—C15—H15	119.6
C7—C8—H8B	108.7	C1—N1—C9	119.19 (14)
C9—C8—H8B	108.7	C1—N1—H1N	115.2 (15)
H8A—C8—H8B	107.6	C9—N1—H1N	114.2 (14)
N1—C1—C2—C3	−179.37 (16)	N1—C9—C10—C11	−126.55 (18)
C6—C1—C2—C3	−0.5 (3)	C8—C9—C10—C11	112.2 (2)
C1—C2—C3—C4	−0.7 (3)	N1—C9—C10—C15	52.8 (2)
C2—C3—C4—C5	0.9 (3)	C8—C9—C10—C15	−68.4 (2)
C3—C4—C5—C6	0.2 (3)	C15—C10—C11—C12	0.1 (3)
C4—C5—C6—C1	−1.4 (3)	C9—C10—C11—C12	179.52 (18)
C4—C5—C6—C7	176.00 (18)	C10—C11—C12—C13	−0.4 (3)
N1—C1—C6—C5	−179.59 (16)	C11—C12—C13—C14	0.0 (3)
C2—C1—C6—C5	1.5 (3)	C11—C12—C13—Cl1	−179.13 (15)
N1—C1—C6—C7	3.0 (3)	C12—C13—C14—C15	0.6 (3)
C2—C1—C6—C7	−175.94 (16)	Cl1—C13—C14—C15	179.75 (14)
C5—C6—C7—O1	−0.3 (3)	C13—C14—C15—C10	−0.8 (3)
C1—C6—C7—O1	177.09 (18)	C11—C10—C15—C14	0.5 (3)
C5—C6—C7—C8	−175.52 (17)	C9—C10—C15—C14	−178.88 (16)
C1—C6—C7—C8	1.9 (3)	C2—C1—N1—C9	−159.94 (16)
O1—C7—C8—C9	156.11 (19)	C6—C1—N1—C9	21.2 (2)
C6—C7—C8—C9	−28.6 (2)	C10—C9—N1—C1	−168.81 (15)
C7—C8—C9—N1	49.0 (2)	C8—C9—N1—C1	−46.4 (2)
C7—C8—C9—C10	170.10 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.15 (2)	2.957 (2)	162 (2)
C5—H5···Cg3ii	0.93	2.83	3.641 (2)	146
C11—H11···Cg2iii	0.93	2.63	3.465 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.15 (2)	2.957 (2)	162 (2)
C5—H5⋯Cg3ii	0.93	2.83	3.641 (2)	146
C11—H11⋯Cg2iii	0.93	2.63	3.465 (2)	149

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