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

The title compound, C(14)H(15)NO, was synthesized from 2-hydroxy-methyl-enecyclo-hepta-none via a Japp-Klingemann acid-catalyzed cyclization. The seven-membered ring exhibits a slightly distorted envelope conformation. N-H⋯O hydrogen bonds form a centrosymmetric dimer; C-H⋯O hydrogen bonds and π-π stacking inter-actions (the centers of the atoms involved in the stacking interaction are separated by 3.504 Å) give rise to another type of centrosymmetric dimer. In combination, these inter-actions create a stair-like chain of mol-ecules that inter-acts only loosely with neighboring chains via van der Waals inter-actions and weak C-H⋯π contacts.

Related literature

For related literature on the synthesis, structure, anti­cancer and anti­depressant activities, and toxicity of functionalized cyclo­hept[b]indoles, see: Cornec et al. (1998 ▶); Joseph et al. (1999 ▶); Kinnick et al. (2006 ▶); Humphrey & Kuethe (2006 ▶, and references therein); Benoit et al. (2000 ▶); Kavitha & Rajendra Prasad (1999 ▶, and references therein). Brameld et al. (2008 ▶) describe small-mol­ecule conformational preferences derived from crystal structure data. Bernstein et al. (1995 ▶) present the use of the versatile graph-set analysis for the description of hydrogen bonds.

Experimental

Crystal data

C14H15NO

M = 213.27

Monoclinic,

a = 11.461 (3) Å

b = 6.5062 (19) Å

c = 14.459 (4) Å

β = 92.310 (4)°

V = 1077.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 (2) K

0.48 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS as implemented in APEX2; Bruker, 2008 ▶) T min = 0.731, T max = 0.993

9984 measured reflections

2652 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.135

S = 1.00

2652 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL and Mercury.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016498/fl2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016498/fl2202Isup2.hkl

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

C14H15NO	F(000) = 456
Mr = 213.27	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.461 (3) Å	Cell parameters from 1265 reflections
b = 6.5062 (19) Å	θ = 2.3–24.5°
c = 14.459 (4) Å	µ = 0.08 mm−1
β = 92.310 (4)°	T = 100 K
V = 1077.3 (6) Å3	Plate, colourless
Z = 4	0.48 × 0.10 × 0.08 mm

Bruker SMART APEX CCD diffractometer	2652 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
graphite	Rint = 0.081
ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS as implemented in APEX2; Bruker, 2008)	h = −15→15
Tmin = 0.731, Tmax = 0.993	k = −8→8
9984 measured reflections	l = −19→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3
2652 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.28 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	0.13517 (16)	0.2801 (3)	1.08139 (13)	0.0251 (4)
C2	0.21105 (17)	0.3796 (3)	1.15581 (13)	0.0284 (5)
H2A	0.2532	0.2688	1.1901	0.034*
H2B	0.1589	0.4463	1.1998	0.034*
C3	0.30146 (17)	0.5391 (3)	1.12828 (14)	0.0283 (5)
H3A	0.3491	0.5786	1.1841	0.034*
H3B	0.3544	0.4750	1.0841	0.034*
C4	0.24910 (17)	0.7329 (3)	1.08433 (13)	0.0280 (5)
H4A	0.1735	0.7618	1.1125	0.034*
H4B	0.3018	0.8500	1.0988	0.034*
C5	0.22933 (17)	0.7184 (3)	0.97993 (13)	0.0272 (5)
H5A	0.1874	0.8438	0.9586	0.033*
H5B	0.3066	0.7194	0.9516	0.033*
C6	0.16294 (15)	0.5361 (3)	0.94335 (13)	0.0241 (4)
C7	0.12670 (16)	0.3572 (3)	0.98660 (13)	0.0243 (4)
C8	0.06994 (16)	0.3237 (3)	0.83704 (13)	0.0244 (4)
C9	0.02351 (16)	0.2566 (3)	0.75210 (13)	0.0274 (5)
H9	−0.0126	0.1257	0.7455	0.033*
C10	0.03204 (16)	0.3877 (3)	0.67779 (14)	0.0287 (5)
H10	−0.0003	0.3463	0.6192	0.034*
C11	0.08746 (17)	0.5823 (3)	0.68576 (13)	0.0275 (5)
C12	0.13502 (16)	0.6455 (3)	0.77013 (14)	0.0271 (5)
H12	0.1734	0.7746	0.7759	0.032*
C13	0.12601 (16)	0.5160 (3)	0.84787 (13)	0.0245 (4)
C14	0.09470 (18)	0.7160 (3)	0.60049 (14)	0.0339 (5)
H14A	0.1211	0.8539	0.6187	0.051*
H14B	0.0175	0.7250	0.5691	0.051*
H14C	0.1502	0.6555	0.5584	0.051*
N1	0.07063 (13)	0.2311 (2)	0.92167 (10)	0.0253 (4)
H1	0.0402	0.1101	0.9332	0.030*
O1	0.07986 (11)	0.1233 (2)	1.10088 (9)	0.0300 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0207 (10)	0.0302 (10)	0.0251 (11)	0.0036 (8)	0.0076 (8)	0.0000 (8)
C2	0.0258 (10)	0.0348 (11)	0.0248 (11)	0.0005 (9)	0.0034 (9)	0.0010 (9)
C3	0.0240 (10)	0.0350 (11)	0.0258 (11)	0.0028 (9)	0.0002 (8)	−0.0005 (9)
C4	0.0233 (10)	0.0321 (11)	0.0286 (11)	0.0013 (9)	0.0017 (9)	−0.0010 (9)
C5	0.0260 (10)	0.0312 (11)	0.0246 (11)	−0.0014 (9)	0.0036 (9)	0.0008 (9)
C6	0.0183 (9)	0.0305 (10)	0.0237 (10)	0.0030 (8)	0.0032 (8)	−0.0015 (8)
C7	0.0196 (10)	0.0294 (10)	0.0241 (11)	0.0012 (8)	0.0037 (8)	−0.0021 (8)
C8	0.0182 (10)	0.0309 (10)	0.0245 (11)	0.0007 (8)	0.0050 (8)	0.0007 (9)
C9	0.0228 (10)	0.0337 (11)	0.0260 (11)	−0.0034 (9)	0.0049 (8)	−0.0016 (9)
C10	0.0206 (10)	0.0429 (12)	0.0230 (11)	−0.0005 (9)	0.0051 (8)	−0.0025 (9)
C11	0.0210 (10)	0.0380 (12)	0.0239 (11)	−0.0015 (9)	0.0048 (8)	0.0009 (9)
C12	0.0204 (10)	0.0327 (11)	0.0284 (11)	0.0000 (9)	0.0060 (8)	0.0019 (9)
C13	0.0170 (9)	0.0321 (11)	0.0246 (11)	0.0008 (8)	0.0044 (8)	−0.0013 (9)
C14	0.0297 (12)	0.0439 (13)	0.0284 (12)	−0.0028 (10)	0.0067 (9)	0.0052 (10)
N1	0.0226 (9)	0.0292 (9)	0.0243 (9)	−0.0015 (7)	0.0035 (7)	0.0008 (7)
O1	0.0311 (8)	0.0309 (8)	0.0283 (8)	−0.0012 (6)	0.0070 (6)	0.0028 (6)

C1—O1	1.239 (2)	C7—N1	1.385 (2)
C1—C7	1.459 (3)	C8—N1	1.364 (2)
C1—C2	1.502 (3)	C8—C9	1.389 (3)
C2—C3	1.531 (3)	C8—C13	1.412 (3)
C2—H2A	0.9900	C9—C10	1.378 (3)
C2—H2B	0.9900	C9—H9	0.9500
C3—C4	1.524 (3)	C10—C11	1.420 (3)
C3—H3A	0.9900	C10—H10	0.9500
C3—H3B	0.9900	C11—C12	1.379 (3)
C4—C5	1.520 (3)	C11—C14	1.514 (3)
C4—H4A	0.9900	C12—C13	1.412 (3)
C4—H4B	0.9900	C12—H12	0.9500
C5—C6	1.494 (3)	C14—H14A	0.9800
C5—H5A	0.9900	C14—H14B	0.9800
C5—H5B	0.9900	C14—H14C	0.9800
C6—C7	1.393 (3)	N1—H1	0.8800
C6—C13	1.434 (3)
O1—C1—C7	118.77 (18)	N1—C7—C6	109.23 (17)
O1—C1—C2	118.56 (17)	N1—C7—C1	116.39 (17)
C7—C1—C2	122.64 (18)	C6—C7—C1	134.38 (18)
C1—C2—C3	118.96 (16)	N1—C8—C9	130.00 (18)
C1—C2—H2A	107.6	N1—C8—C13	107.80 (17)
C3—C2—H2A	107.6	C9—C8—C13	122.19 (18)
C1—C2—H2B	107.6	C10—C9—C8	117.27 (19)
C3—C2—H2B	107.6	C10—C9—H9	121.4
H2A—C2—H2B	107.0	C8—C9—H9	121.4
C4—C3—C2	114.21 (16)	C9—C10—C11	122.29 (19)
C4—C3—H3A	108.7	C9—C10—H10	118.9
C2—C3—H3A	108.7	C11—C10—H10	118.9
C4—C3—H3B	108.7	C12—C11—C10	119.84 (18)
C2—C3—H3B	108.7	C12—C11—C14	121.11 (18)
H3A—C3—H3B	107.6	C10—C11—C14	119.04 (18)
C5—C4—C3	113.79 (16)	C11—C12—C13	119.17 (18)
C5—C4—H4A	108.8	C11—C12—H12	120.4
C3—C4—H4A	108.8	C13—C12—H12	120.4
C5—C4—H4B	108.8	C12—C13—C8	119.21 (18)
C3—C4—H4B	108.8	C12—C13—C6	133.15 (18)
H4A—C4—H4B	107.7	C8—C13—C6	107.63 (16)
C6—C5—C4	116.99 (16)	C11—C14—H14A	109.5
C6—C5—H5A	108.1	C11—C14—H14B	109.5
C4—C5—H5A	108.1	H14A—C14—H14B	109.5
C6—C5—H5B	108.1	C11—C14—H14C	109.5
C4—C5—H5B	108.1	H14A—C14—H14C	109.5
H5A—C5—H5B	107.3	H14B—C14—H14C	109.5
C7—C6—C13	105.92 (16)	C8—N1—C7	109.40 (16)
C7—C6—C5	131.40 (17)	C8—N1—H1	125.3
C13—C6—C5	122.66 (17)	C7—N1—H1	125.3
O1—C1—C2—C3	165.37 (17)	C9—C10—C11—C12	0.0 (3)
C7—C1—C2—C3	−12.8 (3)	C9—C10—C11—C14	179.14 (17)
C1—C2—C3—C4	64.2 (2)	C10—C11—C12—C13	−1.0 (3)
C2—C3—C4—C5	−88.3 (2)	C14—C11—C12—C13	179.88 (17)
C3—C4—C5—C6	51.7 (2)	C11—C12—C13—C8	0.9 (3)
C4—C5—C6—C7	−9.5 (3)	C11—C12—C13—C6	−178.67 (19)
C4—C5—C6—C13	172.25 (17)	N1—C8—C13—C12	−178.80 (16)
C13—C6—C7—N1	0.32 (19)	C9—C8—C13—C12	0.3 (3)
C5—C6—C7—N1	−178.10 (18)	N1—C8—C13—C6	0.8 (2)
C13—C6—C7—C1	−179.5 (2)	C9—C8—C13—C6	179.93 (16)
C5—C6—C7—C1	2.0 (3)	C7—C6—C13—C12	178.9 (2)
O1—C1—C7—N1	−9.3 (3)	C5—C6—C13—C12	−2.5 (3)
C2—C1—C7—N1	168.83 (16)	C7—C6—C13—C8	−0.71 (19)
O1—C1—C7—C6	170.51 (19)	C5—C6—C13—C8	177.89 (16)
C2—C1—C7—C6	−11.3 (3)	C9—C8—N1—C7	−179.65 (18)
N1—C8—C9—C10	177.61 (18)	C13—C8—N1—C7	−0.7 (2)
C13—C8—C9—C10	−1.3 (3)	C6—C7—N1—C8	0.2 (2)
C8—C9—C10—C11	1.1 (3)	C1—C7—N1—C8	−179.91 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.09	2.890 (2)	150.
C4—H4a···O1ii	0.99	2.59	3.211 (3)	121
C2—H2B···Cg1iii	0.99	2.88	3.740 (2)	146
C5—H5b···C10iv	0.99	2.90	3.794 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.09	2.890 (2)	150
C4—H4a⋯O1ii	0.99	2.59	3.211 (3)	121
C2—H2B⋯Cg1iii	0.99	2.88	3.740 (2)	146
C5—H5b⋯C10iv	0.99	2.90	3.794 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C8–C13 ring.