2-Chloro-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

In the title mol-ecule, C(13)H(12)ClNO, the dihedral angle between the benzene and pyrrole rings is 1.38 (9)°. The cyclo-heptene ring adopts a distorted twist chair and sofa conformation. Inter-molecular N-H⋯O hydrogen bonds form an R(2) (2)(10) loop in the crystal packing. Further, weak C-H⋯O and C-H⋯π (involving the benzene ring) inter-actions are found in the crystal structure.

Related literature

For the biological activity of indole derivatives, see: Gribble (2000 ▶); Knölker & Reddy (2002 ▶); Kawasaki & Higuchi (2005 ▶); Bennasar et al. (1993 ▶); Hong et al. (2006 ▶); Lacoume et al. (1972 ▶); Joseph et al. (1998 ▶, 2000 ▶). For related crystallographic studies of cyclo­hept[b]indoles, see: Archana et al. (2010 ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H12ClNO

M = 233.69

Monoclinic,

a = 11.6354 (4) Å

b = 6.3798 (2) Å

c = 14.4513 (5) Å

β = 92.767 (3)°

V = 1071.49 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 150 K

0.40 × 0.30 × 0.30 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011 ▶) T min = 0.879, T max = 0.907

4977 measured reflections

2274 independent reflections

1836 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.096

S = 1.04

2274 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022945/tk5099sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022945/tk5099Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022945/tk5099Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812022945/tk5099Isup4.cml

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

C13H12ClNO	F(000) = 488
Mr = 233.69	Dx = 1.449 Mg m−3
Monoclinic, P21/n	Melting point: 389 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.6354 (4) Å	Cell parameters from 2495 reflections
b = 6.3798 (2) Å	θ = 3.2–28.4°
c = 14.4513 (5) Å	µ = 0.33 mm−1
β = 92.767 (3)°	T = 150 K
V = 1071.49 (6) Å3	Block, colourless
Z = 4	0.40 × 0.30 × 0.30 mm

Agilent Xcalibur Ruby Gemini diffractometer	2274 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.5081 pixels mm-1	θmax = 28.4°, θmin = 3.5°
ω scans	h = −14→15
Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011)	k = −8→7
Tmin = 0.879, Tmax = 0.907	l = −12→19
4977 measured 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.4689P] where P = (Fo2 + 2Fc2)/3
2274 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
Cl2	0.59361 (4)	−0.24239 (8)	0.08648 (3)	0.0357 (2)
O6	0.57812 (10)	0.3697 (2)	0.60006 (8)	0.0280 (4)
N5	0.56976 (12)	0.2648 (3)	0.42004 (10)	0.0225 (5)
C1	0.63668 (14)	−0.1524 (3)	0.26774 (12)	0.0244 (5)
C2	0.58717 (14)	−0.0838 (3)	0.18511 (12)	0.0262 (5)
C3	0.53084 (14)	0.1108 (3)	0.17503 (12)	0.0275 (6)
C4	0.52189 (15)	0.2416 (3)	0.24985 (12)	0.0256 (5)
C4A	0.56937 (14)	0.1720 (3)	0.33521 (12)	0.0223 (5)
C5A	0.62720 (14)	0.1378 (3)	0.48468 (11)	0.0211 (5)
C6	0.63461 (14)	0.2152 (3)	0.58029 (12)	0.0229 (5)
C7	0.71201 (15)	0.1148 (3)	0.65476 (12)	0.0273 (5)
C8	0.80230 (15)	−0.0440 (3)	0.62766 (12)	0.0258 (5)
C9	0.75353 (15)	−0.2421 (3)	0.58213 (12)	0.0254 (5)
C10	0.73457 (16)	−0.2246 (3)	0.47726 (12)	0.0254 (5)
C10A	0.66477 (13)	−0.0419 (3)	0.44109 (12)	0.0214 (5)
C10B	0.62718 (14)	−0.0218 (3)	0.34549 (12)	0.0220 (5)
H1	0.67583	−0.28293	0.27228	0.0293*
H3	0.49882	0.15197	0.11609	0.0330*
H4	0.48492	0.37398	0.24388	0.0307*
H5	0.5389 (17)	0.380 (3)	0.4311 (14)	0.031 (6)*
H7A	0.66192	0.04481	0.69880	0.0328*
H7B	0.75270	0.22911	0.68916	0.0328*
H8A	0.85431	0.02420	0.58455	0.0309*
H8B	0.84908	−0.08411	0.68393	0.0309*
H9A	0.67922	−0.27558	0.60929	0.0305*
H9B	0.80688	−0.35980	0.59647	0.0305*
H10A	0.81089	−0.21821	0.44992	0.0305*
H10B	0.69653	−0.35477	0.45448	0.0305*

	U11	U22	U33	U12	U13	U23
Cl2	0.0376 (3)	0.0460 (3)	0.0233 (2)	0.0078 (2)	0.0001 (2)	−0.0094 (2)
O6	0.0322 (7)	0.0244 (7)	0.0275 (7)	0.0012 (5)	0.0032 (5)	−0.0036 (6)
N5	0.0242 (8)	0.0205 (8)	0.0229 (8)	0.0027 (7)	0.0009 (6)	−0.0004 (7)
C1	0.0213 (8)	0.0259 (9)	0.0261 (9)	0.0005 (8)	0.0008 (7)	−0.0003 (8)
C2	0.0241 (9)	0.0336 (10)	0.0209 (9)	−0.0007 (8)	0.0026 (7)	−0.0058 (8)
C3	0.0219 (9)	0.0382 (11)	0.0222 (9)	0.0016 (8)	0.0002 (7)	0.0042 (8)
C4	0.0231 (8)	0.0269 (10)	0.0267 (9)	0.0039 (8)	0.0013 (7)	0.0035 (8)
C4A	0.0182 (8)	0.0245 (9)	0.0242 (9)	−0.0027 (7)	0.0016 (7)	−0.0005 (8)
C5A	0.0187 (8)	0.0209 (9)	0.0235 (8)	−0.0033 (7)	0.0003 (6)	0.0007 (7)
C6	0.0224 (8)	0.0220 (9)	0.0245 (9)	−0.0069 (7)	0.0031 (7)	−0.0008 (7)
C7	0.0322 (9)	0.0287 (10)	0.0208 (9)	−0.0034 (8)	−0.0011 (7)	0.0004 (8)
C8	0.0255 (9)	0.0280 (10)	0.0234 (9)	−0.0028 (8)	−0.0037 (7)	0.0025 (8)
C9	0.0259 (9)	0.0229 (9)	0.0269 (9)	0.0003 (7)	−0.0039 (8)	0.0035 (8)
C10	0.0272 (9)	0.0222 (9)	0.0265 (9)	0.0021 (7)	−0.0023 (7)	−0.0013 (8)
C10A	0.0175 (8)	0.0236 (9)	0.0230 (9)	−0.0036 (7)	0.0005 (6)	−0.0005 (7)
C10B	0.0177 (8)	0.0244 (9)	0.0238 (8)	−0.0024 (7)	0.0009 (7)	0.0002 (8)

Cl2—C2	1.7525 (19)	C8—C9	1.522 (3)
O6—C6	1.226 (2)	C9—C10	1.525 (2)
N5—C4A	1.361 (2)	C10—C10A	1.500 (3)
N5—C5A	1.384 (2)	C10A—C10B	1.435 (2)
N5—H5	0.837 (19)	C1—H1	0.9500
C1—C10B	1.407 (3)	C3—H3	0.9500
C1—C2	1.372 (2)	C4—H4	0.9500
C2—C3	1.408 (3)	C7—H7A	0.9900
C3—C4	1.374 (3)	C7—H7B	0.9900
C4—C4A	1.399 (2)	C8—H8A	0.9900
C4A—C10B	1.412 (3)	C8—H8B	0.9900
C5A—C6	1.466 (2)	C9—H9A	0.9900
C5A—C10A	1.389 (3)	C9—H9B	0.9900
C6—C7	1.512 (2)	C10—H10A	0.9900
C7—C8	1.524 (3)	C10—H10B	0.9900
C4A—N5—C5A	109.50 (16)	C1—C10B—C10A	133.14 (17)
C4A—N5—H5	124.8 (14)	C2—C1—H1	121.00
C5A—N5—H5	125.7 (14)	C10B—C1—H1	121.00
C2—C1—C10B	117.39 (17)	C2—C3—H3	120.00
Cl2—C2—C3	117.57 (13)	C4—C3—H3	120.00
Cl2—C2—C1	119.41 (14)	C3—C4—H4	121.00
C1—C2—C3	123.02 (17)	C4A—C4—H4	121.00
C2—C3—C4	120.45 (16)	C6—C7—H7A	107.00
C3—C4—C4A	117.35 (17)	C6—C7—H7B	107.00
N5—C4A—C4	129.78 (18)	C8—C7—H7A	107.00
N5—C4A—C10B	107.77 (15)	C8—C7—H7B	107.00
C4—C4A—C10B	122.44 (17)	H7A—C7—H7B	107.00
N5—C5A—C6	116.33 (16)	C7—C8—H8A	109.00
C6—C5A—C10A	134.44 (16)	C7—C8—H8B	109.00
N5—C5A—C10A	109.23 (15)	C9—C8—H8A	109.00
O6—C6—C7	118.84 (16)	C9—C8—H8B	109.00
C5A—C6—C7	122.28 (16)	H8A—C8—H8B	108.00
O6—C6—C5A	118.86 (16)	C8—C9—H9A	109.00
C6—C7—C8	119.54 (15)	C8—C9—H9B	109.00
C7—C8—C9	114.57 (15)	C10—C9—H9A	109.00
C8—C9—C10	113.70 (15)	C10—C9—H9B	109.00
C9—C10—C10A	116.94 (15)	H9A—C9—H9B	108.00
C5A—C10A—C10B	105.96 (15)	C9—C10—H10A	108.00
C10—C10A—C10B	122.67 (16)	C9—C10—H10B	108.00
C5A—C10A—C10	131.32 (16)	C10A—C10—H10A	108.00
C4A—C10B—C10A	107.53 (16)	C10A—C10—H10B	108.00
C1—C10B—C4A	119.33 (16)	H10A—C10—H10B	107.00
C5A—N5—C4A—C4	−180.00 (18)	N5—C5A—C6—C7	−168.77 (16)
C5A—N5—C4A—C10B	0.65 (19)	C10A—C5A—C6—O6	−169.76 (18)
C4A—N5—C5A—C6	−179.61 (15)	C10A—C5A—C6—C7	12.0 (3)
C4A—N5—C5A—C10A	−0.2 (2)	N5—C5A—C10A—C10	177.14 (17)
C10B—C1—C2—Cl2	−178.65 (13)	N5—C5A—C10A—C10B	−0.37 (19)
C10B—C1—C2—C3	1.6 (3)	C6—C5A—C10A—C10	−3.6 (3)
C2—C1—C10B—C4A	−0.8 (2)	C6—C5A—C10A—C10B	178.93 (18)
C2—C1—C10B—C10A	178.53 (18)	O6—C6—C7—C8	−166.26 (16)
Cl2—C2—C3—C4	179.40 (14)	C5A—C6—C7—C8	12.0 (3)
C1—C2—C3—C4	−0.8 (3)	C6—C7—C8—C9	−63.1 (2)
C2—C3—C4—C4A	−0.8 (3)	C7—C8—C9—C10	88.01 (18)
C3—C4—C4A—N5	−177.70 (17)	C8—C9—C10—C10A	−52.9 (2)
C3—C4—C4A—C10B	1.6 (3)	C9—C10—C10A—C5A	11.6 (3)
N5—C4A—C10B—C1	178.59 (15)	C9—C10—C10A—C10B	−171.28 (16)
N5—C4A—C10B—C10A	−0.87 (19)	C5A—C10A—C10B—C1	−178.59 (18)
C4—C4A—C10B—C1	−0.8 (3)	C5A—C10A—C10B—C4A	0.75 (19)
C4—C4A—C10B—C10A	179.72 (16)	C10—C10A—C10B—C1	3.6 (3)
N5—C5A—C6—O6	9.5 (2)	C10—C10A—C10B—C4A	−177.02 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6i	0.837 (19)	2.13 (2)	2.904 (2)	153.2 (19)
C9—H9A···O6ii	0.99	2.55	3.228 (2)	125
C7—H7A···Cg2iii	0.99	2.95	3.7969 (19)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C4,C4A,C10B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O6i	0.837 (19)	2.13 (2)	2.904 (2)	153.2 (19)
C9—H9A⋯O6ii	0.99	2.55	3.228 (2)	125
C7—H7A⋯Cg2iii	0.99	2.95	3.7969 (19)	144

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