9-Ethyl-2,3-dihydro-9H-carbazol-4(1H)-one.

In the title compound, C(28)H(30)N(2)O(2), the cyclo-hexene ring system adopts a sofa conformation. The crystal structure is stabilized by C-H⋯O inter-actions between methyl H atoms of the ethyl substituents and the O atoms of carbonyl groups of adjacent mol-ecules, and by an inter-molecular carbon-yl-carbonyl inter-actions [3.207 (2) Å].

Related literature

For related literature, see: Abraham (1975 ▶); Govindasamy et al. (1999 ▶); Hewlins et al. (1984 ▶); Kansal et al. (1986 ▶); Mi et al. (2003 ▶); Nardelli (1983 ▶); Phillipson & Zenk (1980 ▶); Saxton (1983 ▶); Allen et al. (1998 ▶); Cremer & Pople (1975 ▶); Mohanakrishnan & Srinivasasan (1995 ▶ ▶, 1995 ▶ ▶).

Experimental

Crystal data

C14H15NO

M = 213.27

Monoclinic,

a = 8.3742 (6) Å

b = 17.033 (1) Å

c = 8.6083 (5) Å

β = 116.432 (3)°

V = 1099.51 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

11070 measured reflections

2334 independent reflections

1898 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.03

2334 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024318/lx2064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024318/lx2064Isup2.hkl

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

C14H15NO	F000 = 456
Mr = 213.27	Dx = 1.288 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2850 reflections
a = 8.3742 (6) Å	θ = 20.0–26.8º
b = 17.033 (1) Å	µ = 0.08 mm−1
c = 8.6083 (5) Å	T = 293 (2) K
β = 116.432 (3)º	Block, colourless
V = 1099.51 (12) Å3	0.21 × 0.19 × 0.17 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2334 independent reflections
Radiation source: fine-focus sealed tube	1898 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 10 pixels mm-1	θmax = 26.8º
T = 293(2) K	θmin = 2.4º
ω scans	h = −10→10
Absorption correction: none	k = −21→21
11070 measured reflections	l = −10→10

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.2126P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2334 reflections	Δρmax = 0.15 e Å−3
146 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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	0.41850 (18)	0.62548 (8)	0.62150 (18)	0.0419 (3)
H1	0.5200	0.6388	0.7217	0.050*
C2	0.3279 (2)	0.68137 (8)	0.4981 (2)	0.0506 (4)
H2	0.3685	0.7330	0.5160	0.061*
C3	0.1766 (2)	0.66211 (9)	0.3472 (2)	0.0527 (4)
H3	0.1186	0.7011	0.2659	0.063*
C4	0.11103 (19)	0.58687 (8)	0.31534 (17)	0.0457 (3)
H4	0.0102	0.5741	0.2140	0.055*
C5	0.20092 (16)	0.53077 (8)	0.44009 (15)	0.0359 (3)
C6	0.35512 (16)	0.54847 (7)	0.59327 (15)	0.0343 (3)
C7	0.40707 (16)	0.47683 (7)	0.69054 (15)	0.0350 (3)
C8	0.55752 (16)	0.45924 (8)	0.85455 (16)	0.0392 (3)
C9	0.56815 (19)	0.37540 (9)	0.91598 (19)	0.0490 (4)
H9A	0.6218	0.3752	1.0417	0.059*
H9B	0.6462	0.3461	0.8811	0.059*
C10	0.38967 (19)	0.33358 (9)	0.84713 (19)	0.0509 (4)
H10A	0.3178	0.3574	0.8970	0.061*
H10B	0.4091	0.2790	0.8832	0.061*
C11	0.28888 (19)	0.33744 (8)	0.65050 (19)	0.0465 (3)
H11A	0.3476	0.3049	0.5989	0.056*
H11B	0.1682	0.3182	0.6123	0.056*
C12	0.28502 (16)	0.42042 (7)	0.59547 (16)	0.0364 (3)
C13	0.01251 (17)	0.41064 (8)	0.30768 (17)	0.0431 (3)
H13A	−0.0791	0.4483	0.2400	0.052*
H13B	−0.0388	0.3740	0.3593	0.052*
C14	0.0697 (2)	0.36655 (11)	0.1896 (2)	0.0595 (4)
H14A	0.1250	0.4022	0.1418	0.089*
H14B	−0.0326	0.3429	0.0973	0.089*
H14C	0.1534	0.3264	0.2543	0.089*
N1	0.16080 (13)	0.45195 (6)	0.44527 (13)	0.0372 (3)
O1	0.67261 (13)	0.50731 (6)	0.93817 (12)	0.0530 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0411 (7)	0.0438 (7)	0.0420 (7)	−0.0052 (6)	0.0196 (6)	−0.0026 (6)
C2	0.0601 (9)	0.0400 (7)	0.0568 (9)	−0.0026 (7)	0.0307 (8)	0.0030 (6)
C3	0.0602 (9)	0.0474 (8)	0.0506 (8)	0.0113 (7)	0.0248 (7)	0.0144 (7)
C4	0.0426 (8)	0.0533 (8)	0.0364 (7)	0.0082 (6)	0.0134 (6)	0.0042 (6)
C5	0.0341 (6)	0.0409 (7)	0.0335 (6)	0.0027 (5)	0.0158 (5)	−0.0019 (5)
C6	0.0321 (6)	0.0397 (7)	0.0331 (6)	0.0006 (5)	0.0164 (5)	−0.0013 (5)
C7	0.0314 (6)	0.0387 (7)	0.0336 (6)	0.0000 (5)	0.0133 (5)	−0.0012 (5)
C8	0.0312 (6)	0.0514 (8)	0.0344 (6)	0.0007 (6)	0.0140 (5)	−0.0014 (6)
C9	0.0422 (8)	0.0549 (9)	0.0430 (7)	0.0080 (6)	0.0128 (6)	0.0090 (6)
C10	0.0509 (9)	0.0447 (8)	0.0546 (8)	0.0030 (6)	0.0213 (7)	0.0113 (6)
C11	0.0443 (8)	0.0370 (7)	0.0535 (8)	−0.0003 (6)	0.0176 (6)	−0.0008 (6)
C12	0.0327 (6)	0.0393 (7)	0.0362 (6)	0.0019 (5)	0.0145 (5)	−0.0018 (5)
C13	0.0311 (7)	0.0491 (8)	0.0415 (7)	−0.0042 (6)	0.0093 (5)	−0.0086 (6)
C14	0.0462 (9)	0.0782 (11)	0.0497 (8)	−0.0101 (8)	0.0172 (7)	−0.0251 (8)
N1	0.0318 (5)	0.0389 (6)	0.0346 (6)	−0.0001 (4)	0.0092 (4)	−0.0041 (4)
O1	0.0399 (5)	0.0643 (7)	0.0420 (5)	−0.0092 (5)	0.0067 (4)	−0.0038 (5)

C1—C2	1.376 (2)	C9—H9A	0.9700
C1—C6	1.395 (2)	C9—H9B	0.9700
C1—H1	0.9300	C10—C11	1.520 (2)
C2—C3	1.391 (2)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.373 (2)	C11—C12	1.486 (2)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.383 (2)	C11—H11B	0.9700
C4—H4	0.9300	C12—N1	1.358 (2)
C5—N1	1.390 (2)	C13—N1	1.460 (2)
C5—C6	1.408 (2)	C13—C14	1.503 (2)
C6—C7	1.434 (2)	C13—H13A	0.9700
C7—C12	1.376 (2)	C13—H13B	0.9700
C7—C8	1.445 (2)	C14—H14A	0.9600
C8—O1	1.225 (2)	C14—H14B	0.9600
C8—C9	1.512 (2)	C14—H14C	0.9600
C9—C10	1.518 (2)
C2—C1—C6	118.67 (13)	C9—C10—C11	112.13 (12)
C2—C1—H1	120.7	C9—C10—H10A	109.2
C6—C1—H1	120.7	C11—C10—H10A	109.2
C1—C2—C3	121.19 (14)	C9—C10—H10B	109.2
C1—C2—H2	119.4	C11—C10—H10B	109.2
C3—C2—H2	119.4	H10A—C10—H10B	107.9
C4—C3—C2	121.57 (13)	C12—C11—C10	108.58 (11)
C4—C3—H3	119.2	C12—C11—H11A	110.0
C2—C3—H3	119.2	C10—C11—H11A	110.0
C3—C4—C5	117.31 (13)	C12—C11—H11B	110.0
C3—C4—H4	121.3	C10—C11—H11B	110.0
C5—C4—H4	121.3	H11A—C11—H11B	108.4
C4—C5—N1	129.54 (12)	N1—C12—C7	109.97 (11)
C4—C5—C6	122.31 (12)	N1—C12—C11	125.32 (11)
N1—C5—C6	108.12 (10)	C7—C12—C11	124.71 (11)
C1—C6—C5	118.94 (12)	N1—C13—C14	112.16 (11)
C1—C6—C7	134.87 (12)	N1—C13—H13A	109.2
C5—C6—C7	106.15 (11)	C14—C13—H13A	109.2
C12—C7—C6	107.16 (11)	N1—C13—H13B	109.2
C12—C7—C8	122.03 (12)	C14—C13—H13B	109.2
C6—C7—C8	130.79 (12)	H13A—C13—H13B	107.9
O1—C8—C7	123.48 (13)	C13—C14—H14A	109.5
O1—C8—C9	121.17 (12)	C13—C14—H14B	109.5
C7—C8—C9	115.32 (11)	H14A—C14—H14B	109.5
C8—C9—C10	114.35 (11)	C13—C14—H14C	109.5
C8—C9—H9A	108.7	H14A—C14—H14C	109.5
C10—C9—H9A	108.7	H14B—C14—H14C	109.5
C8—C9—H9B	108.7	C12—N1—C5	108.60 (10)
C10—C9—H9B	108.7	C12—N1—C13	126.60 (11)
H9A—C9—H9B	107.6	C5—N1—C13	124.77 (11)
C6—C1—C2—C3	−0.4 (2)	C7—C8—C9—C10	−26.10 (17)
C1—C2—C3—C4	0.3 (2)	C8—C9—C10—C11	53.43 (17)
C2—C3—C4—C5	0.3 (2)	C9—C10—C11—C12	−50.05 (16)
C3—C4—C5—N1	177.12 (13)	C6—C7—C12—N1	0.19 (14)
C3—C4—C5—C6	−0.9 (2)	C8—C7—C12—N1	−178.24 (11)
C2—C1—C6—C5	−0.11 (18)	C6—C7—C12—C11	−179.46 (12)
C2—C1—C6—C7	−177.39 (13)	C8—C7—C12—C11	2.1 (2)
C4—C5—C6—C1	0.80 (18)	C10—C11—C12—N1	−155.43 (12)
N1—C5—C6—C1	−177.59 (11)	C10—C11—C12—C7	24.16 (19)
C4—C5—C6—C7	178.79 (12)	C7—C12—N1—C5	0.06 (14)
N1—C5—C6—C7	0.40 (13)	C11—C12—N1—C5	179.71 (12)
C1—C6—C7—C12	177.16 (14)	C7—C12—N1—C13	178.10 (11)
C5—C6—C7—C12	−0.36 (13)	C11—C12—N1—C13	−2.2 (2)
C1—C6—C7—C8	−4.6 (2)	C4—C5—N1—C12	−178.53 (13)
C5—C6—C7—C8	177.88 (12)	C6—C5—N1—C12	−0.29 (13)
C12—C7—C8—O1	176.58 (12)	C4—C5—N1—C13	3.4 (2)
C6—C7—C8—O1	−1.4 (2)	C6—C5—N1—C13	−178.38 (11)
C12—C7—C8—C9	−1.59 (18)	C14—C13—N1—C12	−80.84 (17)
C6—C7—C8—C9	−179.60 (13)	C14—C13—N1—C5	96.90 (16)
O1—C8—C9—C10	155.68 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.96	2.60	3.549 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.96	2.60	3.549 (2)	170

Symmetry code: (i) .