(RS)-1-[5-(2-Chloro-prop-yl)indolin-1-yl]ethanone.

In the title compound, C(13)H(16)ClNO, the acetyl-indoline moiety is roughly planar (r.m.s. deviation = 0.0048 Å). The chloro-propyl group is out of the plane and is statistically disordered over two positions. Indeed, the Cl and CH(3) groups located on the stereogenic carbon exchange with each other. The whole crystal is a racemate. Non-classical C-H⋯O hydrogen bonds between symmetry-related benzene rings stabilize the crystal structure.

Related literature

The title compound was synthesized as an inter­mediate in the search for a new synthetic route to silodosin, an adrenoceptor antagonist, see: Asselin et al. (2000 ▶); Bremner et al. (2000 ▶); Elworthy et al. (1997 ▶); Sorbera et al. (2001 ▶). For related structures, see: Moreno et al. (1998 ▶); Wang et al.(2007 ▶).

Experimental

Crystal data

C13H16ClNO

M = 237.72

Triclinic,

a = 6.9041 (5) Å

b = 8.4887 (6) Å

c = 10.6463 (7) Å

α = 76.423 (1)°

β = 86.955 (1)°

γ = 89.969 (1)°

V = 605.61 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.46 × 0.41 × 0.22 mm

Data collection

Bruker AXS SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.877, T max = 0.938

4719 measured reflections

2343 independent reflections

1915 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.07

2343 reflections

163 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050476/dn2631sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050476/dn2631Isup2.hkl

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

C13H16ClNO	Z = 2
Mr = 237.72	F(000) = 252
Triclinic, P1	Dx = 1.304 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9041 (5) Å	Cell parameters from 2890 reflections
b = 8.4887 (6) Å	θ = 2.5–27.0°
c = 10.6463 (7) Å	µ = 0.29 mm−1
α = 76.423 (1)°	T = 173 K
β = 86.955 (1)°	Block, colourless
γ = 89.969 (1)°	0.46 × 0.41 × 0.22 mm
V = 605.61 (7) Å3

Bruker AXS SMART 1000 CCD diffractometer	2343 independent reflections
Radiation source: fine-focus sealed tube	1915 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −8→8
Tmin = 0.877, Tmax = 0.938	k = −10→10
4719 measured reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2707P] where P = (Fo2 + 2Fc2)/3
2343 reflections	(Δ/σ)max = 0.002
163 parameters	Δρmax = 0.35 e Å−3
5 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
O1	0.2493 (2)	0.69510 (15)	0.57618 (13)	0.0462 (4)
N1	0.25327 (19)	0.49053 (16)	0.47345 (13)	0.0306 (3)
C1	0.2670 (3)	0.4283 (2)	0.35441 (16)	0.0355 (4)
H1A	0.3925	0.4604	0.3057	0.043*
H1B	0.1605	0.4711	0.2977	0.043*
C2	0.2505 (3)	0.2437 (2)	0.40071 (17)	0.0371 (4)
H2A	0.1365	0.2019	0.3654	0.045*
H2B	0.3686	0.1912	0.3739	0.045*
C3	0.2275 (2)	0.21325 (19)	0.54586 (16)	0.0293 (4)
C4	0.2056 (2)	0.0682 (2)	0.63687 (17)	0.0328 (4)
H4	0.2030	−0.0309	0.6101	0.039*
C5	0.1872 (2)	0.0670 (2)	0.76852 (17)	0.0331 (4)
C6	0.1927 (2)	0.2141 (2)	0.80423 (16)	0.0340 (4)
H6	0.1817	0.2138	0.8936	0.041*
C7	0.2137 (2)	0.3621 (2)	0.71377 (16)	0.0320 (4)
H7	0.2165	0.4614	0.7403	0.038*
C8	0.2304 (2)	0.35962 (19)	0.58388 (15)	0.0278 (4)
C9	0.2613 (2)	0.6503 (2)	0.47457 (18)	0.0337 (4)
C10	0.2848 (3)	0.7693 (2)	0.34518 (19)	0.0404 (4)
H10A	0.2923	0.8797	0.3582	0.061*
H10B	0.1734	0.7598	0.2940	0.061*
H10C	0.4042	0.7460	0.2992	0.061*
C11	0.1537 (3)	−0.0898 (2)	0.86977 (18)	0.0422 (5)
H11A	0.0257	−0.1352	0.8581	0.051*
H11B	0.1485	−0.0653	0.9563	0.051*
C12	0.3060 (3)	−0.2180 (2)	0.86693 (18)	0.0400 (4)
H12A	0.3065	−0.2493	0.7859	0.048*
Cl1	0.5409 (4)	−0.1512 (3)	0.8927 (2)	0.0525 (4)	0.50
C13	0.245 (2)	−0.3659 (13)	0.9768 (12)	0.100 (5)	0.50
H13A	0.2548	−0.3380	1.0605	0.150*	0.50
H13B	0.3311	−0.4566	0.9725	0.150*	0.50
H13C	0.1111	−0.3970	0.9672	0.150*	0.50
Cl1B	0.2300 (4)	−0.4048 (3)	0.97881 (18)	0.0532 (4)	0.50
C13B	0.4978 (16)	−0.1668 (14)	0.9079 (13)	0.102 (5)	0.50
H13D	0.5386	−0.0621	0.8516	0.152*	0.50
H13E	0.5958	−0.2483	0.9009	0.152*	0.50
H13F	0.4834	−0.1567	0.9977	0.152*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0608 (9)	0.0299 (7)	0.0505 (8)	0.0026 (6)	−0.0098 (6)	−0.0135 (6)
N1	0.0303 (7)	0.0277 (7)	0.0333 (7)	0.0010 (5)	−0.0030 (6)	−0.0053 (6)
C1	0.0388 (9)	0.0357 (9)	0.0312 (9)	0.0025 (7)	−0.0018 (7)	−0.0063 (7)
C2	0.0447 (10)	0.0343 (9)	0.0334 (9)	−0.0024 (7)	0.0009 (7)	−0.0106 (7)
C3	0.0261 (8)	0.0299 (8)	0.0328 (9)	0.0017 (6)	−0.0018 (6)	−0.0092 (7)
C4	0.0309 (8)	0.0268 (8)	0.0409 (10)	0.0031 (6)	−0.0008 (7)	−0.0087 (7)
C5	0.0260 (8)	0.0341 (9)	0.0357 (9)	0.0046 (7)	−0.0005 (7)	−0.0016 (7)
C6	0.0304 (9)	0.0420 (10)	0.0293 (9)	0.0067 (7)	−0.0021 (7)	−0.0075 (7)
C7	0.0287 (8)	0.0330 (9)	0.0366 (9)	0.0045 (7)	−0.0044 (7)	−0.0122 (7)
C8	0.0218 (7)	0.0279 (8)	0.0335 (9)	0.0024 (6)	−0.0033 (6)	−0.0063 (6)
C9	0.0262 (8)	0.0279 (8)	0.0473 (10)	0.0011 (6)	−0.0070 (7)	−0.0081 (7)
C10	0.0332 (9)	0.0302 (9)	0.0534 (11)	0.0003 (7)	−0.0039 (8)	−0.0005 (8)
C11	0.0401 (10)	0.0401 (10)	0.0408 (10)	0.0038 (8)	0.0034 (8)	0.0006 (8)
C12	0.0495 (11)	0.0321 (9)	0.0361 (10)	0.0033 (8)	−0.0037 (8)	−0.0034 (7)
Cl1	0.0513 (8)	0.0619 (10)	0.0492 (7)	0.0144 (6)	−0.0190 (6)	−0.0190 (7)
C13	0.118 (9)	0.030 (6)	0.136 (8)	0.027 (5)	0.001 (5)	0.009 (4)
Cl1B	0.0777 (10)	0.0273 (10)	0.0482 (8)	0.0008 (7)	−0.0027 (6)	0.0036 (5)
C13B	0.081 (7)	0.049 (5)	0.161 (10)	0.028 (4)	−0.026 (6)	0.006 (5)

O1—C9	1.227 (2)	C7—H7	0.9500
N1—C9	1.360 (2)	C9—C10	1.506 (3)
N1—C8	1.417 (2)	C10—H10A	0.9800
N1—C1	1.482 (2)	C10—H10B	0.9800
C1—C2	1.531 (2)	C10—H10C	0.9800
C1—H1A	0.9900	C11—C12	1.517 (3)
C1—H1B	0.9900	C11—H11A	0.9900
C2—C3	1.505 (2)	C11—H11B	0.9900
C2—H2A	0.9900	C12—C13B	1.511 (10)
C2—H2B	0.9900	C12—C13	1.543 (10)
C3—C4	1.379 (2)	C12—Cl1	1.774 (3)
C3—C8	1.395 (2)	C12—Cl1B	1.804 (3)
C4—C5	1.398 (2)	C12—H12A	0.9604
C4—H4	0.9500	C13—H13A	0.9800
C5—C6	1.389 (3)	C13—H13B	0.9800
C5—C11	1.513 (2)	C13—H13C	0.9800
C6—C7	1.395 (2)	C13B—H13D	0.9800
C6—H6	0.9500	C13B—H13E	0.9800
C7—C8	1.387 (2)	C13B—H13F	0.9800
C9—N1—C8	125.79 (15)	H10A—C10—H10B	109.5
C9—N1—C1	124.26 (14)	C9—C10—H10C	109.5
C8—N1—C1	109.95 (13)	H10A—C10—H10C	109.5
N1—C1—C2	105.54 (13)	H10B—C10—H10C	109.5
N1—C1—H1A	110.6	C5—C11—C12	114.95 (15)
C2—C1—H1A	110.6	C5—C11—H11A	108.5
N1—C1—H1B	110.6	C12—C11—H11A	108.5
C2—C1—H1B	110.6	C5—C11—H11B	108.5
H1A—C1—H1B	108.8	C12—C11—H11B	108.5
C3—C2—C1	104.39 (13)	H11A—C11—H11B	107.5
C3—C2—H2A	110.9	C13B—C12—C11	110.8 (5)
C1—C2—H2A	110.9	C13B—C12—C13	103.1 (7)
C3—C2—H2B	110.9	C11—C12—C13	106.5 (6)
C1—C2—H2B	110.9	C13B—C12—Cl1	7.7 (6)
H2A—C2—H2B	108.9	C11—C12—Cl1	112.22 (16)
C4—C3—C8	120.53 (15)	C13—C12—Cl1	109.3 (6)
C4—C3—C2	129.25 (15)	C13B—C12—Cl1B	107.8 (5)
C8—C3—C2	110.22 (14)	C11—C12—Cl1B	109.45 (16)
C3—C4—C5	120.04 (15)	C13—C12—Cl1B	7.6 (6)
C3—C4—H4	120.0	Cl1—C12—Cl1B	113.43 (15)
C5—C4—H4	120.0	C13B—C12—H12A	117.2
C6—C5—C4	118.45 (15)	C11—C12—H12A	109.8
C6—C5—C11	120.51 (16)	C13—C12—H12A	108.8
C4—C5—C11	120.99 (16)	Cl1—C12—H12A	110.2
C5—C6—C7	122.45 (16)	Cl1B—C12—H12A	101.2
C5—C6—H6	118.8	C12—C13—H13A	109.5
C7—C6—H6	118.8	C12—C13—H13B	109.5
C8—C7—C6	117.80 (15)	H13A—C13—H13B	109.5
C8—C7—H7	121.1	C12—C13—H13C	109.5
C6—C7—H7	121.1	H13A—C13—H13C	109.5
C7—C8—C3	120.73 (15)	H13B—C13—H13C	109.5
C7—C8—N1	129.36 (15)	C12—C13B—H13D	109.5
C3—C8—N1	109.90 (14)	C12—C13B—H13E	109.5
O1—C9—N1	121.52 (16)	H13D—C13B—H13E	109.5
O1—C9—C10	121.67 (16)	C12—C13B—H13F	109.5
N1—C9—C10	116.80 (16)	H13D—C13B—H13F	109.5
C9—C10—H10A	109.5	H13E—C13B—H13F	109.5
C9—C10—H10B	109.5
C9—N1—C1—C2	−179.87 (15)	C4—C3—C8—N1	−179.69 (14)
C8—N1—C1—C2	−0.04 (18)	C2—C3—C8—N1	0.25 (18)
N1—C1—C2—C3	0.17 (17)	C9—N1—C8—C7	−0.8 (3)
C1—C2—C3—C4	179.67 (16)	C1—N1—C8—C7	179.34 (16)
C1—C2—C3—C8	−0.26 (18)	C9—N1—C8—C3	179.70 (14)
C8—C3—C4—C5	−0.4 (2)	C1—N1—C8—C3	−0.13 (18)
C2—C3—C4—C5	179.70 (16)	C8—N1—C9—O1	0.2 (3)
C3—C4—C5—C6	−0.4 (2)	C1—N1—C9—O1	−179.96 (16)
C3—C4—C5—C11	177.16 (15)	C8—N1—C9—C10	−179.55 (14)
C4—C5—C6—C7	0.7 (2)	C1—N1—C9—C10	0.3 (2)
C11—C5—C6—C7	−176.83 (15)	C6—C5—C11—C12	−125.81 (18)
C5—C6—C7—C8	−0.3 (2)	C4—C5—C11—C12	56.7 (2)
C6—C7—C8—C3	−0.4 (2)	C5—C11—C12—C13B	68.4 (6)
C6—C7—C8—N1	−179.86 (15)	C5—C11—C12—C13	179.9 (6)
C4—C3—C8—C7	0.8 (2)	C5—C11—C12—Cl1	60.3 (2)
C2—C3—C8—C7	−179.27 (14)	C5—C11—C12—Cl1B	−172.81 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.45	3.388 (2)	168.
C12—H12A···O1i	0.96	2.44	3.388 (2)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.45	3.388 (2)	168
C12—H12A⋯O1i	0.96	2.44	3.388 (2)	169

Symmetry code: (i) .