1-(4-Chloro-phen-yl)-3-(2-meth-oxy-anilino)propan-1-one.

In the title compound, C(16)H(16)ClNO(2), the mol-ecule adopts a bowed conformation, with a dihedral angle of 39.9 (2)° between the aromatic rings. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating C(6) chains propagating in [010]. Very weak aromatic π-π stacking is also observed [centroid-centroid distance = 4.040 (2) Å].

Related literature

For the synthesis of quinoline derivatives, see: Peifer et al. (2007 ▶). For background to the anti­microbial activity of quinolines, see: Yamashkin & Oreshkina (2006 ▶). For further synthetic details, see: Dienys et al. (1977 ▶); Volkov et al. (2007 ▶).

Experimental

Crystal data

C16H16ClNO2

M = 289.75

Orthorhombic,

a = 7.1690 (6) Å

b = 14.4303 (11) Å

c = 28.667 (3) Å

V = 2965.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.48 × 0.36 × 0.20 mm

Data collection

Rigaku AFC-7S Mercury diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.927, T max = 0.950

31012 measured reflections

3035 independent reflections

2016 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.198

S = 1.14

3035 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: CrystalStructure (Rigaku/MSC, 2005) ▶ and SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054449/hb5773sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054449/hb5773Isup2.hkl

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

C16H16ClNO2	F(000) = 1216
Mr = 289.75	Dx = 1.298 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 13752 reflections
a = 7.1690 (6) Å	θ = 2.8–56.1°
b = 14.4303 (11) Å	µ = 0.26 mm−1
c = 28.667 (3) Å	T = 293 K
V = 2965.6 (4) Å3	Block, yellow
Z = 8	0.48 × 0.36 × 0.20 mm

Rigaku AFC-7S Mercury diffractometer	3035 independent reflections
Radiation source: fine-focus sealed tube	2016 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω scans	θmax = 28.0°, θmin = 2.8°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −8→8
Tmin = 0.927, Tmax = 0.950	k = −17→13
31012 measured reflections	l = −34→34

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.077	H-atom parameters constrained
wR(F2) = 0.198	w = 1/[σ2(Fo2) + (0.0693P)2 + 1.923P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
3035 reflections	Δρmax = 0.16 e Å−3
182 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (11)

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	0.69107 (15)	0.62967 (7)	0.61228 (4)	0.0854 (4)
O1	0.4661 (4)	0.2337 (2)	0.30790 (9)	0.0883 (9)
O2	0.9890 (4)	0.25566 (16)	0.49786 (9)	0.0727 (7)
N1	0.7477 (5)	0.2272 (2)	0.36535 (10)	0.0684 (8)
H1	0.6749	0.2852	0.3609	0.103*
C1	0.7033 (5)	0.1459 (2)	0.34171 (11)	0.0623 (9)
C2	0.5513 (6)	0.1488 (3)	0.31054 (12)	0.0690 (10)
C3	0.5005 (7)	0.0718 (3)	0.28559 (14)	0.0866 (13)
H3A	0.4010	0.0746	0.2648	0.104*
C4	0.5979 (9)	−0.0100 (3)	0.29143 (16)	0.1005 (16)
H4A	0.5628	−0.0626	0.2748	0.121*
C5	0.7461 (9)	−0.0141 (3)	0.32167 (16)	0.0958 (15)
H5A	0.8109	−0.0695	0.3254	0.115*
C6	0.8003 (6)	0.0638 (3)	0.34675 (13)	0.0783 (11)
H6A	0.9018	0.0607	0.3669	0.094*
C7	0.3001 (8)	0.2415 (4)	0.28063 (18)	0.123 (2)
H7A	0.2579	0.3046	0.2809	0.185*
H7B	0.2051	0.2023	0.2935	0.185*
H7C	0.3257	0.2229	0.2491	0.185*
C8	0.8471 (5)	0.2253 (2)	0.40935 (12)	0.0654 (9)
H8A	0.9791	0.2153	0.4038	0.078*
H8B	0.8010	0.1748	0.4285	0.078*
C9	0.8179 (5)	0.3165 (2)	0.43408 (11)	0.0573 (8)
H9A	0.8793	0.3651	0.4164	0.069*
H9B	0.6855	0.3304	0.4346	0.069*
C10	0.8898 (5)	0.3180 (2)	0.48287 (11)	0.0554 (8)
C11	0.8363 (4)	0.3968 (2)	0.51434 (11)	0.0541 (8)
C12	0.8721 (5)	0.3894 (2)	0.56181 (12)	0.0667 (10)
H12A	0.9276	0.3360	0.5735	0.080*
C13	0.8258 (5)	0.4607 (3)	0.59179 (12)	0.0697 (10)
H13A	0.8488	0.4551	0.6236	0.084*
C14	0.7456 (5)	0.5401 (2)	0.57432 (12)	0.0605 (9)
C15	0.7108 (5)	0.5491 (2)	0.52753 (13)	0.0621 (9)
H15A	0.6576	0.6032	0.5159	0.074*
C16	0.7554 (5)	0.4773 (2)	0.49781 (12)	0.0580 (8)
H16A	0.7306	0.4831	0.4661	0.070*

	U11	U22	U33	U12	U13	U23
Cl1	0.0803 (8)	0.0852 (7)	0.0905 (8)	0.0111 (5)	−0.0050 (5)	−0.0216 (5)
O1	0.093 (2)	0.092 (2)	0.0794 (19)	0.0084 (16)	−0.0267 (15)	−0.0150 (14)
O2	0.0761 (17)	0.0629 (15)	0.0790 (16)	0.0129 (12)	−0.0181 (13)	0.0009 (12)
N1	0.086 (2)	0.0609 (17)	0.0581 (17)	−0.0038 (15)	−0.0151 (16)	0.0005 (13)
C1	0.076 (2)	0.062 (2)	0.0493 (19)	−0.0098 (18)	0.0071 (17)	0.0004 (15)
C2	0.085 (3)	0.071 (2)	0.051 (2)	−0.013 (2)	0.0041 (19)	−0.0045 (17)
C3	0.104 (3)	0.089 (3)	0.067 (3)	−0.026 (3)	0.005 (2)	−0.011 (2)
C4	0.148 (5)	0.080 (3)	0.074 (3)	−0.035 (3)	0.017 (3)	−0.016 (2)
C5	0.148 (5)	0.058 (2)	0.081 (3)	0.001 (3)	0.024 (3)	0.002 (2)
C6	0.100 (3)	0.065 (2)	0.070 (2)	−0.001 (2)	0.008 (2)	0.0031 (19)
C7	0.114 (4)	0.147 (5)	0.109 (4)	0.022 (3)	−0.050 (3)	−0.021 (3)
C8	0.065 (2)	0.066 (2)	0.064 (2)	−0.0021 (17)	−0.0099 (18)	−0.0009 (16)
C9	0.0517 (19)	0.061 (2)	0.059 (2)	−0.0049 (15)	−0.0056 (15)	0.0038 (15)
C10	0.0472 (18)	0.0536 (19)	0.065 (2)	−0.0073 (15)	−0.0069 (15)	0.0057 (15)
C11	0.0432 (17)	0.0570 (19)	0.062 (2)	−0.0058 (14)	−0.0074 (15)	0.0039 (15)
C12	0.073 (2)	0.062 (2)	0.065 (2)	0.0093 (17)	−0.0146 (18)	0.0044 (16)
C13	0.077 (2)	0.078 (2)	0.054 (2)	0.0080 (19)	−0.0122 (18)	−0.0015 (18)
C14	0.0523 (19)	0.061 (2)	0.068 (2)	−0.0029 (16)	−0.0025 (17)	−0.0043 (16)
C15	0.056 (2)	0.0540 (19)	0.076 (2)	−0.0010 (15)	−0.0092 (17)	0.0093 (17)
C16	0.0564 (19)	0.058 (2)	0.060 (2)	−0.0017 (15)	−0.0091 (16)	0.0050 (15)

Cl1—C14	1.734 (3)	C7—H7C	0.9600
O1—C2	1.371 (4)	C8—C9	1.510 (4)
O1—C7	1.428 (5)	C8—H8A	0.9700
O2—C10	1.224 (4)	C8—H8B	0.9700
N1—C1	1.392 (4)	C9—C10	1.491 (4)
N1—C8	1.449 (4)	C9—H9A	0.9700
N1—H1	0.9952	C9—H9B	0.9700
C1—C6	1.381 (5)	C10—C11	1.501 (5)
C1—C2	1.410 (5)	C11—C16	1.382 (4)
C2—C3	1.370 (5)	C11—C12	1.389 (5)
C3—C4	1.382 (7)	C12—C13	1.381 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.373 (7)	C13—C14	1.377 (5)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.390 (6)	C14—C15	1.371 (5)
C5—H5A	0.9300	C15—C16	1.379 (5)
C6—H6A	0.9300	C15—H15A	0.9300
C7—H7A	0.9600	C16—H16A	0.9300
C7—H7B	0.9600
C2—O1—C7	118.2 (3)	N1—C8—H8B	109.9
C1—N1—C8	121.3 (3)	C9—C8—H8B	109.9
C1—N1—H1	121.8	H8A—C8—H8B	108.3
C8—N1—H1	112.7	C10—C9—C8	113.9 (3)
C6—C1—N1	123.8 (3)	C10—C9—H9A	108.8
C6—C1—C2	118.8 (3)	C8—C9—H9A	108.8
N1—C1—C2	117.4 (3)	C10—C9—H9B	108.8
C3—C2—O1	125.3 (4)	C8—C9—H9B	108.8
C3—C2—C1	120.8 (4)	H9A—C9—H9B	107.7
O1—C2—C1	113.9 (3)	O2—C10—C9	121.3 (3)
C2—C3—C4	119.7 (4)	O2—C10—C11	119.6 (3)
C2—C3—H3A	120.1	C9—C10—C11	119.1 (3)
C4—C3—H3A	120.1	C16—C11—C12	118.6 (3)
C5—C4—C3	120.3 (4)	C16—C11—C10	122.5 (3)
C5—C4—H4A	119.9	C12—C11—C10	118.9 (3)
C3—C4—H4A	119.9	C13—C12—C11	120.5 (3)
C4—C5—C6	120.6 (4)	C13—C12—H12A	119.7
C4—C5—H5A	119.7	C11—C12—H12A	119.7
C6—C5—H5A	119.7	C14—C13—C12	119.6 (3)
C1—C6—C5	119.9 (4)	C14—C13—H13A	120.2
C1—C6—H6A	120.0	C12—C13—H13A	120.2
C5—C6—H6A	120.0	C15—C14—C13	120.8 (3)
O1—C7—H7A	109.5	C15—C14—Cl1	120.1 (3)
O1—C7—H7B	109.5	C13—C14—Cl1	119.1 (3)
H7A—C7—H7B	109.5	C14—C15—C16	119.4 (3)
O1—C7—H7C	109.5	C14—C15—H15A	120.3
H7A—C7—H7C	109.5	C16—C15—H15A	120.3
H7B—C7—H7C	109.5	C15—C16—C11	121.1 (3)
N1—C8—C9	108.9 (3)	C15—C16—H16A	119.4
N1—C8—H8A	109.9	C11—C16—H16A	119.4
C9—C8—H8A	109.9

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2i	0.93	2.49	3.414 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2i	0.93	2.49	3.414 (4)	171

Symmetry code: (i) .