Ethyl 4-oxo-2,3,4,9-tetra-hydro-1H-carbazole-3-carboxyl-ate.

In the title compound, C(15)H(15)NO(3), the carbazole skeleton includes an eth-oxy-carbonyl group at the 3-position. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, forming a dihedral angle of 0.89 (4)°. The cyclo-hexenone ring has an envelope conformation. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three dimensional network. A weak C-H⋯π inter-action is also observed.

Related literature

For background to tetra­hydro­carbazole systems present in indole-type alkaloids, see: Saxton (1983 ▶). For related structures, see: Hökelek et al. (1994 ▶, 1998 ▶, 1999 ▶, 2009 ▶); Patır et al. (1997 ▶); Hökelek & Patır (1999 ▶); Çaylak et al. (2007 ▶); Uludağ et al. (2009 ▶). For the use of 4-oxo-tetra­hydro­carbazole in the syntheses of biologically active species, see: Kumar et al. (2008 ▶); Ergün et al. (2002 ▶); Li & Vince (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H15NO3

M = 257.28

Orthorhombic,

a = 9.1057 (3) Å

b = 12.7031 (4) Å

c = 21.3874 (5) Å

V = 2473.89 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.43 × 0.26 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.960, T max = 0.981

12029 measured reflections

2993 independent reflections

2258 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.102

S = 1.04

2993 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018678/hb5881sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018678/hb5881Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018678/hb5881Isup3.cml

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

C15H15NO3	F(000) = 1088
Mr = 257.28	Dx = 1.382 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3293 reflections
a = 9.1057 (3) Å	θ = 2.9–28.3°
b = 12.7031 (4) Å	µ = 0.10 mm−1
c = 21.3874 (5) Å	T = 100 K
V = 2473.89 (13) Å3	Block, colorless
Z = 8	0.43 × 0.26 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2993 independent reflections
Radiation source: fine-focus sealed tube	2258 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→9
Tmin = 0.960, Tmax = 0.981	k = −16→8
12029 measured reflections	l = −20→28

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.044P)2 + 0.6029P] where P = (Fo2 + 2Fc2)/3
2993 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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 > 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
O1	0.27325 (11)	0.49989 (7)	0.23207 (4)	0.0234 (2)
O2	0.13644 (11)	0.53475 (7)	0.37765 (4)	0.0226 (2)
O3	0.31033 (11)	0.40993 (7)	0.36958 (4)	0.0220 (2)
C1	0.01764 (17)	0.22360 (9)	0.25890 (6)	0.0217 (3)
H1A	0.0260	0.1466	0.2651	0.026*
H1B	−0.0879	0.2422	0.2578	0.026*
C2	0.09311 (17)	0.28148 (9)	0.31263 (7)	0.0218 (3)
H2A	0.1906	0.2495	0.3202	0.026*
H2B	0.0340	0.2730	0.3511	0.026*
C3	0.11251 (16)	0.39973 (9)	0.29874 (6)	0.0196 (3)
H3	0.0122	0.4306	0.2936	0.024*
C4	0.19696 (16)	0.42026 (9)	0.23804 (6)	0.0191 (3)
C4A	0.17494 (15)	0.34286 (9)	0.18970 (6)	0.0178 (3)
C5	0.30954 (16)	0.40632 (10)	0.08810 (6)	0.0200 (3)
H5	0.3511	0.4689	0.1048	0.024*
C5A	0.22407 (15)	0.34016 (9)	0.12551 (6)	0.0176 (3)
C6	0.33239 (17)	0.37872 (11)	0.02632 (7)	0.0231 (3)
H6	0.3903	0.4232	0.0005	0.028*
C7	0.27209 (17)	0.28667 (10)	0.00100 (7)	0.0244 (3)
H7	0.2901	0.2697	−0.0416	0.029*
C8	0.18676 (17)	0.22010 (10)	0.03698 (7)	0.0229 (3)
H8	0.1457	0.1576	0.0200	0.027*
C8A	0.16323 (15)	0.24812 (10)	0.09904 (7)	0.0192 (3)
N9	0.08119 (13)	0.19804 (9)	0.14526 (5)	0.0202 (3)
H9	0.0272 (18)	0.1408 (13)	0.1399 (7)	0.029 (4)*
C9A	0.08866 (15)	0.25402 (9)	0.19910 (6)	0.0181 (3)
C10	0.18566 (16)	0.45682 (10)	0.35239 (6)	0.0187 (3)
C11	0.39176 (16)	0.45682 (10)	0.42153 (7)	0.0212 (3)
H11A	0.4609	0.4042	0.4388	0.025*
H11B	0.3222	0.4767	0.4551	0.025*
C12	0.47603 (17)	0.55264 (10)	0.40117 (7)	0.0246 (3)
H12A	0.5356	0.5785	0.4361	0.037*
H12B	0.4071	0.6076	0.3881	0.037*
H12C	0.5403	0.5342	0.3661	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0268 (6)	0.0194 (4)	0.0241 (6)	−0.0053 (4)	0.0006 (5)	−0.0008 (4)
O2	0.0235 (6)	0.0223 (4)	0.0220 (6)	0.0049 (4)	−0.0009 (4)	−0.0027 (4)
O3	0.0217 (6)	0.0210 (4)	0.0233 (5)	0.0045 (4)	−0.0023 (4)	−0.0024 (4)
C1	0.0210 (8)	0.0174 (6)	0.0265 (8)	−0.0011 (5)	0.0036 (6)	−0.0004 (5)
C2	0.0251 (8)	0.0185 (6)	0.0216 (8)	−0.0003 (5)	0.0050 (6)	0.0007 (5)
C3	0.0213 (8)	0.0171 (6)	0.0204 (7)	0.0022 (5)	−0.0005 (6)	−0.0008 (5)
C4	0.0188 (8)	0.0172 (6)	0.0212 (8)	0.0027 (5)	−0.0041 (6)	0.0012 (5)
C4A	0.0171 (8)	0.0177 (6)	0.0186 (7)	0.0003 (5)	−0.0022 (6)	0.0015 (5)
C5	0.0199 (8)	0.0201 (6)	0.0199 (8)	−0.0003 (5)	−0.0031 (6)	0.0019 (5)
C5A	0.0171 (8)	0.0172 (6)	0.0184 (7)	0.0030 (5)	−0.0034 (6)	0.0005 (5)
C6	0.0227 (8)	0.0261 (7)	0.0206 (8)	0.0027 (6)	−0.0006 (6)	0.0047 (5)
C7	0.0268 (9)	0.0283 (7)	0.0179 (7)	0.0057 (6)	−0.0011 (6)	−0.0012 (6)
C8	0.0245 (8)	0.0210 (6)	0.0231 (8)	0.0026 (5)	−0.0036 (6)	−0.0036 (5)
C8A	0.0183 (8)	0.0184 (6)	0.0207 (8)	0.0031 (5)	−0.0017 (6)	0.0009 (5)
N9	0.0205 (7)	0.0164 (5)	0.0236 (7)	−0.0011 (5)	0.0009 (5)	−0.0028 (4)
C9A	0.0157 (7)	0.0165 (5)	0.0222 (7)	0.0029 (5)	−0.0014 (6)	−0.0007 (5)
C10	0.0187 (8)	0.0185 (6)	0.0190 (7)	0.0005 (5)	0.0026 (6)	0.0040 (5)
C11	0.0218 (8)	0.0241 (6)	0.0178 (7)	0.0035 (5)	−0.0026 (6)	0.0012 (5)
C12	0.0246 (9)	0.0249 (6)	0.0243 (8)	0.0008 (6)	−0.0021 (7)	0.0003 (5)

O1—C4	1.2338 (15)	C5A—C5	1.3972 (19)
O2—C10	1.2136 (15)	C5A—C8A	1.4123 (17)
O3—C10	1.3336 (17)	C6—C7	1.4008 (19)
O3—C11	1.4626 (16)	C6—H6	0.9500
C1—C9A	1.4844 (19)	C7—C8	1.382 (2)
C1—H1A	0.9900	C7—H7	0.9500
C1—H1B	0.9900	C8—H8	0.9500
C2—C1	1.5276 (19)	C8A—C8	1.391 (2)
C2—H2A	0.9900	N9—C8A	1.3928 (18)
C2—H2B	0.9900	N9—C9A	1.3550 (17)
C3—C2	1.5413 (17)	N9—H9	0.886 (17)
C3—C4	1.531 (2)	C10—C3	1.5121 (19)
C3—H3	1.0000	C11—H11A	0.9900
C4—C4A	1.4409 (18)	C11—H11B	0.9900
C4A—C5A	1.4442 (19)	C12—C11	1.5033 (19)
C4A—C9A	1.3897 (17)	C12—H12A	0.9800
C5—C6	1.383 (2)	C12—H12B	0.9800
C5—H5	0.9500	C12—H12C	0.9800
C10—O3—C11	117.33 (10)	C5—C6—H6	119.3
C2—C1—H1A	109.9	C7—C6—H6	119.3
C2—C1—H1B	109.9	C6—C7—H7	119.5
C9A—C1—C2	109.08 (11)	C8—C7—C6	121.04 (14)
C9A—C1—H1A	109.9	C8—C7—H7	119.5
C9A—C1—H1B	109.9	C7—C8—C8A	117.48 (13)
H1A—C1—H1B	108.3	C7—C8—H8	121.3
C1—C2—C3	112.07 (11)	C8A—C8—H8	121.3
C1—C2—H2A	109.2	N9—C8A—C5A	107.69 (12)
C1—C2—H2B	109.2	C8—C8A—N9	130.03 (12)
C3—C2—H2A	109.2	C8—C8A—C5A	122.28 (13)
C3—C2—H2B	109.2	C8A—N9—H9	125.5 (10)
H2A—C2—H2B	107.9	C9A—N9—C8A	109.67 (11)
C2—C3—H3	107.4	C9A—N9—H9	124.7 (10)
C4—C3—C2	112.77 (11)	N9—C9A—C1	125.01 (12)
C4—C3—H3	107.4	N9—C9A—C4A	109.36 (12)
C10—C3—C2	111.82 (11)	C4A—C9A—C1	125.62 (12)
C10—C3—C4	109.90 (11)	O2—C10—O3	123.78 (13)
C10—C3—H3	107.4	O2—C10—C3	124.50 (13)
O1—C4—C3	120.68 (12)	O3—C10—C3	111.71 (11)
O1—C4—C4A	124.31 (13)	O3—C11—C12	111.62 (11)
C4A—C4—C3	114.98 (11)	O3—C11—H11A	109.3
C4—C4A—C5A	130.93 (12)	O3—C11—H11B	109.3
C9A—C4A—C4	121.94 (12)	C12—C11—H11A	109.3
C9A—C4A—C5A	107.06 (11)	C12—C11—H11B	109.3
C5A—C5—H5	120.7	H11A—C11—H11B	108.0
C6—C5—C5A	118.59 (13)	C11—C12—H12A	109.5
C6—C5—H5	120.7	C11—C12—H12B	109.5
C5—C5A—C4A	134.64 (12)	C11—C12—H12C	109.5
C5—C5A—C8A	119.13 (12)	H12A—C12—H12B	109.5
C8A—C5A—C4A	106.21 (11)	H12A—C12—H12C	109.5
C5—C6—C7	121.47 (14)	H12B—C12—H12C	109.5
C10—O3—C11—C12	−77.69 (15)	C5A—C4A—C9A—C1	178.62 (12)
C11—O3—C10—O2	−0.64 (19)	C5A—C4A—C9A—N9	−0.36 (15)
C11—O3—C10—C3	−179.50 (10)	C5A—C5—C6—C7	−0.1 (2)
C2—C1—C9A—N9	159.90 (13)	C4A—C5A—C5—C6	−178.78 (14)
C2—C1—C9A—C4A	−18.93 (18)	C8A—C5A—C5—C6	−0.4 (2)
C3—C2—C1—C9A	47.43 (15)	C4A—C5A—C8A—N9	0.09 (14)
C4—C3—C2—C1	−56.21 (16)	C4A—C5A—C8A—C8	179.53 (13)
C10—C3—C2—C1	179.34 (12)	C5—C5A—C8A—N9	−178.68 (12)
C2—C3—C4—O1	−149.89 (13)	C5—C5A—C8A—C8	0.8 (2)
C2—C3—C4—C4A	32.36 (16)	C5—C6—C7—C8	0.3 (2)
C10—C3—C4—O1	−24.40 (17)	C6—C7—C8—C8A	0.0 (2)
C10—C3—C4—C4A	157.85 (11)	N9—C8A—C8—C7	178.76 (13)
O1—C4—C4A—C5A	−3.9 (2)	C5A—C8A—C8—C7	−0.5 (2)
O1—C4—C4A—C9A	179.48 (13)	C8A—N9—C9A—C1	−178.57 (12)
C3—C4—C4A—C5A	173.73 (13)	C8A—N9—C9A—C4A	0.42 (15)
C3—C4—C4A—C9A	−2.87 (18)	C9A—N9—C8A—C5A	−0.31 (15)
C4—C4A—C5A—C8A	−176.82 (14)	C9A—N9—C8A—C8	−179.70 (14)
C4—C4A—C5A—C5	1.7 (3)	O2—C10—C3—C2	−126.61 (14)
C9A—C4A—C5A—C5	178.65 (15)	O2—C10—C3—C4	107.35 (15)
C9A—C4A—C5A—C8A	0.16 (14)	O3—C10—C3—C2	52.23 (15)
C4—C4A—C9A—N9	176.95 (12)	O3—C10—C3—C4	−73.80 (13)
C4—C4A—C9A—C1	−4.1 (2)

Cg3 is the centroid of the C5A/C5–C8,C8A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O2i	0.885 (16)	2.044 (16)	2.9103 (15)	166.0 (15)
C3—H3···O1ii	1.00	2.41	3.4053 (17)	173
C11—H11A···Cg3iii	0.99	2.86	3.7358 (15)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C5A/C5–C8,C8A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O2i	0.885 (16)	2.044 (16)	2.9103 (15)	166.0 (15)
C3—H3⋯O1ii	1.00	2.41	3.4053 (17)	173
C11—H11A⋯Cg3iii	0.99	2.86	3.7358 (15)	148

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