(RS)-1-(1-Acetyl-indolin-5-yl)-2-chloro-propan-1-one.

The mol-ecule of the title compound, C(13)H(14)ClNO(2), is roughly planar [maximum deviation = 0.060 (2) Å] with the disordered Cl/CH(3) group asymetrically distributed on both sides of the mean plane. Indeed, the Cl and CH(3) located on the stereogenic carbon exchange each other with occupancy factors in the ratio 0.60:0.40. The whole crystal is a racemate. Non-classical C-H⋯O hydrogen bonds and π-π inter-actions [centroid-centroid distance = 3.6959 (9) Å] between symmetry-related phenyl rings stabilize the crystal structure.

Related literature

The title compound was synthesised as an inter­mediate in a search for a new synthetic route for 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

C13H14ClNO2

M = 251.70

Triclinic,

a = 8.4748 (5) Å

b = 9.0928 (5) Å

c = 9.4952 (5) Å

α = 112.071 (1)°

β = 110.345 (1)°

γ = 99.913 (1)°

V = 595.92 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 173 K

0.46 × 0.36 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.871, T max = 0.955

6682 measured reflections

2594 independent reflections

2242 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.18

2594 reflections

178 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.21 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, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020969/dn2565sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020969/dn2565Isup2.hkl

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

C13H14ClNO2	Z = 2
Mr = 251.70	F(000) = 264
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4748 (5) Å	Cell parameters from 4108 reflections
b = 9.0928 (5) Å	θ = 2.6–27.0°
c = 9.4952 (5) Å	µ = 0.31 mm−1
α = 112.071 (1)°	T = 173 K
β = 110.345 (1)°	Block, colorless
γ = 99.913 (1)°	0.46 × 0.36 × 0.15 mm
V = 595.92 (6) Å3

Bruker SMART 1000 CCD diffractometer	2594 independent reflections
Radiation source: fine-focus sealed tube	2242 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 27.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→10
Tmin = 0.871, Tmax = 0.955	k = −11→11
6682 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0322P)2 + 0.3925P] where P = (Fo2 + 2Fc2)/3
2594 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.20 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	Occ. (<1)
O1	0.9779 (2)	−0.01243 (19)	0.2587 (2)	0.0410 (4)
O2	0.35372 (18)	0.39091 (17)	0.09272 (18)	0.0348 (3)
N1	0.7298 (2)	−0.10127 (19)	0.28713 (19)	0.0271 (3)
C1	0.6190 (3)	−0.2154 (3)	0.3214 (3)	0.0394 (5)
H1A	0.6802	−0.1916	0.4415	0.047*
H1B	0.5956	−0.3354	0.2463	0.047*
C2	0.4441 (3)	−0.1788 (2)	0.2847 (3)	0.0323 (4)
H2A	0.3427	−0.2765	0.1824	0.039*
H2B	0.4166	−0.1526	0.3827	0.039*
C3	0.4790 (2)	−0.0270 (2)	0.2553 (2)	0.0252 (4)
C4	0.3712 (2)	0.0667 (2)	0.2265 (2)	0.0253 (4)
H4	0.2594	0.0427	0.2300	0.030*
C5	0.4281 (2)	0.1977 (2)	0.1918 (2)	0.0249 (4)
C6	0.5941 (2)	0.2322 (2)	0.1900 (2)	0.0279 (4)
H6	0.6319	0.3208	0.1661	0.033*
C7	0.7055 (2)	0.1416 (2)	0.2219 (2)	0.0292 (4)
H7	0.8188	0.1677	0.2217	0.035*
C8	0.6455 (2)	0.0109 (2)	0.2544 (2)	0.0245 (4)
C9	0.8883 (2)	−0.1095 (2)	0.2860 (2)	0.0296 (4)
C10	0.9462 (3)	−0.2455 (3)	0.3189 (3)	0.0358 (4)
H10A	0.8635	−0.3568	0.2239	0.054*
H10B	0.9452	−0.2369	0.4246	0.054*
H10C	1.0679	−0.2313	0.3298	0.054*
C11	0.3175 (2)	0.3004 (2)	0.1525 (2)	0.0264 (4)
C12	0.1597 (3)	0.2956 (2)	0.1952 (2)	0.0306 (4)
H12	0.1025	0.1787	0.1740	0.037*
C13	0.0115 (16)	0.3460 (17)	0.0833 (16)	0.058 (4)	0.60
H13A	−0.0826	0.3497	0.1206	0.087*	0.60
H13B	−0.0414	0.2617	−0.0370	0.087*	0.60
H13C	0.0678	0.4576	0.0975	0.087*	0.60
Cl1	0.2419 (3)	0.4356 (3)	0.40972 (18)	0.0464 (6)	0.60
C13B	0.244 (2)	0.4216 (19)	0.4003 (16)	0.072 (6)	0.40
H13D	0.3329	0.3851	0.4631	0.108*	0.40
H13E	0.1470	0.4173	0.4347	0.108*	0.40
H13F	0.3008	0.5379	0.4258	0.108*	0.40
Cl1B	0.0086 (5)	0.3588 (5)	0.0840 (4)	0.0361 (9)	0.40

	U11	U22	U33	U12	U13	U23
O1	0.0371 (8)	0.0425 (8)	0.0621 (10)	0.0207 (7)	0.0328 (7)	0.0302 (8)
O2	0.0361 (8)	0.0331 (7)	0.0443 (8)	0.0126 (6)	0.0193 (6)	0.0256 (7)
N1	0.0263 (8)	0.0247 (7)	0.0326 (8)	0.0101 (6)	0.0141 (6)	0.0145 (6)
C1	0.0302 (10)	0.0397 (11)	0.0618 (14)	0.0153 (9)	0.0227 (10)	0.0337 (11)
C2	0.0300 (10)	0.0315 (10)	0.0448 (11)	0.0132 (8)	0.0193 (9)	0.0236 (9)
C3	0.0254 (9)	0.0245 (8)	0.0262 (9)	0.0074 (7)	0.0123 (7)	0.0123 (7)
C4	0.0241 (8)	0.0263 (9)	0.0282 (9)	0.0089 (7)	0.0139 (7)	0.0134 (7)
C5	0.0261 (9)	0.0228 (8)	0.0234 (8)	0.0082 (7)	0.0106 (7)	0.0092 (7)
C6	0.0298 (9)	0.0242 (9)	0.0324 (9)	0.0073 (7)	0.0160 (8)	0.0150 (8)
C7	0.0269 (9)	0.0290 (9)	0.0350 (10)	0.0095 (7)	0.0174 (8)	0.0152 (8)
C8	0.0247 (9)	0.0234 (8)	0.0240 (8)	0.0091 (7)	0.0112 (7)	0.0094 (7)
C9	0.0280 (9)	0.0282 (9)	0.0300 (9)	0.0120 (7)	0.0137 (8)	0.0097 (8)
C10	0.0338 (10)	0.0345 (10)	0.0415 (11)	0.0183 (8)	0.0179 (9)	0.0168 (9)
C11	0.0277 (9)	0.0208 (8)	0.0253 (9)	0.0056 (7)	0.0091 (7)	0.0094 (7)
C12	0.0346 (10)	0.0273 (9)	0.0390 (10)	0.0151 (8)	0.0197 (8)	0.0195 (8)
C13	0.058 (7)	0.049 (6)	0.073 (7)	0.007 (4)	0.035 (5)	0.034 (5)
Cl1	0.0466 (10)	0.0642 (12)	0.0263 (6)	0.0269 (8)	0.0168 (6)	0.0158 (6)
C13B	0.091 (12)	0.052 (7)	0.118 (12)	0.036 (7)	0.066 (9)	0.060 (8)
Cl1B	0.0366 (17)	0.0457 (16)	0.0344 (14)	0.0273 (14)	0.0139 (11)	0.0231 (12)

O1—C9	1.225 (2)	C7—C8	1.393 (3)
O2—C11	1.216 (2)	C7—H7	0.9500
N1—C9	1.362 (2)	C9—C10	1.504 (3)
N1—C8	1.408 (2)	C10—H10A	0.9800
N1—C1	1.482 (2)	C10—H10B	0.9800
C1—C2	1.525 (3)	C10—H10C	0.9800
C1—H1A	0.9900	C11—C12	1.525 (3)
C1—H1B	0.9900	C12—C13	1.598 (10)
C2—C3	1.509 (2)	C12—C13B	1.641 (13)
C2—H2A	0.9900	C12—Cl1B	1.689 (3)
C2—H2B	0.9900	C12—Cl1	1.736 (3)
C3—C4	1.380 (2)	C12—H12	0.9997
C3—C8	1.398 (2)	C13—H13A	0.9800
C4—C5	1.402 (2)	C13—H13B	0.9800
C4—H4	0.9500	C13—H13C	0.9800
C5—C6	1.395 (3)	C13B—H13D	0.9800
C5—C11	1.487 (2)	C13B—H13E	0.9800
C6—C7	1.385 (3)	C13B—H13F	0.9800
C6—H6	0.9500
C9—N1—C8	126.44 (15)	N1—C9—C10	116.09 (17)
C9—N1—C1	123.37 (15)	C9—C10—H10A	109.5
C8—N1—C1	110.18 (14)	C9—C10—H10B	109.5
N1—C1—C2	105.33 (15)	H10A—C10—H10B	109.5
N1—C1—H1A	110.7	C9—C10—H10C	109.5
C2—C1—H1A	110.7	H10A—C10—H10C	109.5
N1—C1—H1B	110.7	H10B—C10—H10C	109.5
C2—C1—H1B	110.7	O2—C11—C5	121.51 (17)
H1A—C1—H1B	108.8	O2—C11—C12	119.99 (16)
C3—C2—C1	104.15 (15)	C5—C11—C12	118.47 (15)
C3—C2—H2A	110.9	C11—C12—C13	112.2 (5)
C1—C2—H2A	110.9	C11—C12—C13B	106.7 (7)
C3—C2—H2B	110.9	C13—C12—C13B	112.7 (8)
C1—C2—H2B	110.9	C11—C12—Cl1B	112.0 (2)
H2A—C2—H2B	108.9	C13—C12—Cl1B	2.8 (6)
C4—C3—C8	120.43 (16)	C13B—C12—Cl1B	110.3 (6)
C4—C3—C2	129.55 (16)	C11—C12—Cl1	108.14 (15)
C8—C3—C2	109.99 (15)	C13—C12—Cl1	109.6 (5)
C3—C4—C5	119.36 (16)	C13B—C12—Cl1	3.1 (7)
C3—C4—H4	120.3	Cl1B—C12—Cl1	107.28 (18)
C5—C4—H4	120.3	C11—C12—H12	109.1
C6—C5—C4	119.17 (16)	C13—C12—H12	108.7
C6—C5—C11	117.85 (16)	C13B—C12—H12	107.3
C4—C5—C11	122.97 (16)	Cl1B—C12—H12	111.2
C7—C6—C5	122.22 (16)	Cl1—C12—H12	109.0
C7—C6—H6	118.9	C12—C13—H13A	109.5
C5—C6—H6	118.9	C12—C13—H13B	109.5
C6—C7—C8	117.69 (17)	C12—C13—H13C	109.5
C6—C7—H7	121.2	C12—C13B—H13D	109.5
C8—C7—H7	121.2	C12—C13B—H13E	109.5
C7—C8—C3	121.11 (16)	H13D—C13B—H13E	109.5
C7—C8—N1	129.13 (16)	C12—C13B—H13F	109.5
C3—C8—N1	109.75 (15)	H13D—C13B—H13F	109.5
O1—C9—N1	121.97 (17)	H13E—C13B—H13F	109.5
O1—C9—C10	121.94 (17)
C9—N1—C1—C2	−172.04 (17)	C9—N1—C8—C3	175.76 (17)
C8—N1—C1—C2	7.0 (2)	C1—N1—C8—C3	−3.2 (2)
N1—C1—C2—C3	−7.7 (2)	C8—N1—C9—O1	1.8 (3)
C1—C2—C3—C4	−175.90 (19)	C1—N1—C9—O1	−179.33 (19)
C1—C2—C3—C8	6.2 (2)	C8—N1—C9—C10	−177.82 (17)
C8—C3—C4—C5	1.6 (3)	C1—N1—C9—C10	1.1 (3)
C2—C3—C4—C5	−176.09 (18)	C6—C5—C11—O2	12.3 (3)
C3—C4—C5—C6	−1.0 (3)	C4—C5—C11—O2	−166.21 (17)
C3—C4—C5—C11	177.50 (16)	C6—C5—C11—C12	−165.37 (16)
C4—C5—C6—C7	−0.2 (3)	C4—C5—C11—C12	16.1 (3)
C11—C5—C6—C7	−178.82 (17)	O2—C11—C12—C13	25.4 (6)
C5—C6—C7—C8	0.8 (3)	C5—C11—C12—C13	−156.9 (5)
C6—C7—C8—C3	−0.2 (3)	O2—C11—C12—C13B	−98.5 (6)
C6—C7—C8—N1	178.75 (17)	C5—C11—C12—C13B	79.3 (6)
C4—C3—C8—C7	−1.0 (3)	O2—C11—C12—Cl1B	22.4 (3)
C2—C3—C8—C7	177.12 (17)	C5—C11—C12—Cl1B	−159.9 (2)
C4—C3—C8—N1	179.83 (16)	O2—C11—C12—Cl1	−95.6 (2)
C2—C3—C8—N1	−2.0 (2)	C5—C11—C12—Cl1	82.12 (19)
C9—N1—C8—C7	−3.3 (3)	C5—C11—C12—Cl1	82.12 (19)
C1—N1—C8—C7	177.69 (19)	C5—C11—C12—Cl1B	−159.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.99	2.44	3.252 (3)	139
C4—H4···O1ii	0.95	2.48	3.430 (2)	177
C12—H12···O1ii	1.00	2.41	3.318 (2)	151

	Centroid–Centroid (Å)	Centroid-to-plane (Å)	Slippage (Å)
Cg1···Cg1iii	3.6959 (9)	3.4713 (6)	1.269

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2i	0.99	2.44	3.252 (3)	139
C4—H4⋯O1ii	0.95	2.48	3.430 (2)	177
C12—H12⋯O1ii	1.00	2.41	3.318 (2)	151

Symmetry codes: (i) ; (ii) .