Ethyl 1-oxo-1,2,3,4-tetra­hydro-9H-carbazole-3-carboxyl­ate

Hökelek, T.; Dal, H.; Tercan, B.; Göçmentürk, M.; Ergün, Y.

doi:10.1107/S160053680902385X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1702-o1703

doi:10.1107/S160053680902385X

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Ethyl 1-oxo-1,2,3,4-tetrahydro-9H-carbazole-3-carboxylate

Tuncer Hökelek,^a ^* Hakan Dal,^b Barış Tercan,^c Mustafa Göçmentürk ^d and Yavuz Ergün ^d

^aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, ^bDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, ^cDepartment of Physics, Karabük University, 78050 Karabük, Turkey, and ^dDepartment of Chemistry, Faculty of Arts and Sciences, Dokuz Eylül University, Tınaztepe, 35160 Buca-zmir, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 19 June 2009; accepted 22 June 2009; online 27 June 2009)

The title compound, C₁₅H₁₅NO₃, contains a carbazole skeleton with an ethoxycarbonyl group at the 3 position. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, forming a dihedral angle of 1.95 (8)°. The cyclohexenone ring has an envelope conformation. In the crystal structure, pairs of strong N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers with R²₂(10) ring motifs. π–π contacts between parallel pyrrole rings [centroid–centroid distance = 3.776 (2) Å] may further stabilize the structure. A weak C—H⋯π interaction is also observed.

Related literature

For tetrahydrocarbazole derivatives as synthetic precursors of cyclic indole-type alkaloids of biological interest, see: Abraham (1975 ); Phillipson & Zenk (1980 ); Saxton (1983 ). The title compound is used in the synthesis of a precursor for the synthesis of the anti-tumor drug ellipticine (Ergün et al., 2004 ). Murraya L. (Rutaceae) is a genus of shrubs or small trees from Southern Asia (Chang, 1977 ) from which carbazole alkaloids have been isolated (Chakraborty & Roy, 1991 ). For the biological activity of carbazole alkaloids, see: Kondo et al. (1986 ); Te Paske et al. (1989a ,b ). For related structures, see: Çaylak et al. (2007 ); Uludağ et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₅NO₃
M_r = 257.28
Monoclinic, P 2₁ /c
a = 5.6811 (3) Å
b = 8.7378 (5) Å
c = 24.8310 (14) Å
β = 93.208 (4)°
V = 1230.69 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.45 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.958, T_max = 0.983
9148 measured reflections
3004 independent reflections
2145 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.221
S = 1.05
3004 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O1ⁱ	0.82 (4)	2.08 (4)	2.834 (3)	154 (4)
C4—H4A⋯Cg3ⁱⁱ	0.99	2.75	3.727 (3)	171
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+2, -z. Cg3 is the centroid of the C5A/C5–C8/C8A ring.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902385X/xu2543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902385X/xu2543Isup2.hkl

checkCIF report

Comment top

Tetrahydrocarbazole derivatives can be considered to be synthetic precursors of cyclic indole-type alkaloids of biological interest (Abraham, 1975; Phillipson & Zenk, 1980; Saxton, 1983). The title compound was used in the synthesis of the precursor compound for the synthesis of anti-tumor drug ellipticine (Ergün et al., 2004). Murraya L. (Rutaceae) is a genus of shrubs or small trees from Southern Asia (Chang, 1977). The main constituent of this genus include carbazole alkaloids (Chakraborty & Roy, 1991). Several biological properties have been reported for carbazole alkaloids including antibiotic, cytotoxic and antiviral activities (Kondo et al., 1986; Te Paske et al., 1989a,b). The title compound may also be used as a precursor in the synthesis of Murraya alkaloids. The present study was undertaken to ascertain its crystal structure.

The molecule of the title compound (Fig. 1) contains a carbazole skeleton with a carboxyethyl group at position 3, where the bond lengths (Allen et al., 1987) and angles are within normal ranges.

An examination of the deviations from the least-squares planes through individual rings shows that rings B (C4a/C5a/C8a/N9/C9a) and C (C5a/C5—C8/C8a) are nearly coplanar [with a maximum deviation of -0.028 (3) Å for atom C4a] with dihedral angle of A/B = 1.95 (8)°. Ring A (C1—C4/C4a/C9a) adopts envelope conformation with atom C3 displaced by 0.527 (3) Å from the plane of the other rings atoms, as in 3a,4,10,10b-tetrahydro-2H-furo[2,3-a]carbazol-5(3H)-one (Çaylak et al., 2007) and 3,3-ethylenedithio-3,3a,4,5,10,10b-hexahydro-2H-furo[2,3-a]carbazole (Uludağ et al., 2009).

In the crystal structure, pairs of strong intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centosymmetric dimers with R²₂(10) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the pyrrole rings, Cg2—Cg2ⁱ, [symmetry code:(i) -x, 1 - y, -z, where Cg2 is centroid of the ring B (C4a/C5a/C8a/N9/C9a)] may further stabilize the structure, with centroid-centroid distance of 3.776 (2) Å. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For general background, see: Abraham (1975); Phillipson & Zenk (1980); Saxton (1983); Ergün et al. (2004); Chang (1977); Chakraborty & Roy (1991); Kondo et al. (1986); Te Paske et al. (1989a,b). For related structures, see: Çaylak et al. (2007); Uludağ et al. (2009). For bond-length data, see: Allen et al. (1987). For ring-motifs, see: Bernstein et al. (1995). Cg3 is the centroid of the C5A/C5–C8/C8A ring.

Experimental top

For the preparation of the title compound, a solution of ethyl 1,2,3,4-tetrahydro-9H-carbazole-3-carboxylate (5.00 g, 20.5 mmol) in methanol (25 ml) was added dropwise to a solution of periodic acid (9.35 g, 41.0 mmol) in methanol-water (1:1, 100 ml) at 273 K. The reaction mixture was stirred for 1 h at 273 K, then stirring was continued for a further 1 h at room temperature. The solvent was evaporated, then the residue was dissolved in chloroform and washed first with sodium carbonate (10%, 50 ml) and then with sodium bisulfite (10%, 50 ml). The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was chromatographed on silica gel using ethyl acetate and crystallized from methanol (yield; 3.17 g, 67%, m.p. 411 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram for the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Ethyl 1-oxo-1,2,3,4-tetrahydro-9H-carbazole-3-carboxylate top

Crystal data top

C₁₅H₁₅NO₃	F(000) = 544
M_r = 257.28	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3480 reflections
a = 5.6811 (3) Å	θ = 1.6–28.3°
b = 8.7378 (5) Å	µ = 0.10 mm⁻¹
c = 24.8310 (14) Å	T = 100 K
β = 93.208 (4)°	Rod-shaped, colorless
V = 1230.69 (12) Å³	0.45 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube	2145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.958, T_max = 0.983	k = −11→9
9148 measured reflections	l = −32→28

Refinement top

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.221	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.1083P)² + 1.2571P] where P = (F_o² + 2F_c²)/3
3004 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 1.25 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₅H₁₅NO₃	V = 1230.69 (12) Å³
M_r = 257.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6811 (3) Å	µ = 0.10 mm⁻¹
b = 8.7378 (5) Å	T = 100 K
c = 24.8310 (14) Å	0.45 × 0.20 × 0.15 mm
β = 93.208 (4)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3004 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2145 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.983	R_int = 0.059
9148 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.221	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.25 e Å⁻³
3004 reflections	Δρ_min = −0.42 e Å⁻³
177 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4546 (3)	0.0609 (2)	0.42291 (7)	0.0294 (5)
O2	−0.0619 (5)	0.3051 (4)	0.27554 (9)	0.0775 (11)
O3	−0.2959 (5)	0.4520 (3)	0.32045 (8)	0.0603 (8)
C1	0.2768 (4)	0.1407 (3)	0.42209 (10)	0.0245 (5)
C2	0.1783 (5)	0.2133 (4)	0.37051 (10)	0.0316 (6)
H2A	0.1988	0.1406	0.3405	0.038*
H2B	0.2727	0.3056	0.3634	0.038*
C3	−0.0831 (5)	0.2597 (4)	0.36991 (11)	0.0355 (7)
H3	−0.1758	0.1623	0.3689	0.043*
C4	−0.1525 (4)	0.3454 (3)	0.41897 (10)	0.0263 (6)
H4A	−0.0978	0.4527	0.4171	0.032*
H4B	−0.3264	0.3461	0.4202	0.032*
C4A	−0.0453 (4)	0.2708 (3)	0.46893 (10)	0.0229 (5)
C5	−0.2963 (4)	0.3489 (3)	0.54916 (10)	0.0270 (6)
H5	−0.4152	0.4041	0.5289	0.032*
C5A	−0.1107 (4)	0.2805 (3)	0.52332 (9)	0.0232 (5)
C6	−0.3046 (5)	0.3353 (3)	0.60418 (11)	0.0313 (6)
H6	−0.4315	0.3802	0.6219	0.038*
C7	−0.1266 (5)	0.2553 (3)	0.63473 (10)	0.0314 (6)
H7	−0.1334	0.2502	0.6728	0.038*
C8	0.0550 (5)	0.1850 (3)	0.61069 (10)	0.0283 (6)
H8	0.1737	0.1313	0.6315	0.034*
C8A	0.0608 (4)	0.1948 (3)	0.55452 (10)	0.0243 (5)
N9	0.2174 (4)	0.1343 (3)	0.52100 (8)	0.0240 (5)
H9	0.335 (7)	0.082 (4)	0.5280 (15)	0.050 (11)*
C9A	0.1539 (4)	0.1807 (3)	0.46917 (9)	0.0233 (5)
C10	−0.1422 (5)	0.3404 (4)	0.31657 (11)	0.0343 (7)
C11	−0.3501 (8)	0.5424 (4)	0.27171 (14)	0.0588 (11)
H11A	−0.3926	0.6478	0.2821	0.071*
H11B	−0.2082	0.5483	0.2504	0.071*
C12	−0.5423 (7)	0.4765 (6)	0.23878 (18)	0.0713 (13)
H12A	−0.5770	0.5416	0.2072	0.107*
H12B	−0.6825	0.4693	0.2599	0.107*
H12C	−0.4976	0.3741	0.2269	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0278 (9)	0.0346 (11)	0.0253 (9)	0.0038 (8)	−0.0018 (7)	0.0018 (8)
O2	0.0752 (18)	0.139 (3)	0.0185 (10)	0.0649 (19)	0.0037 (11)	0.0088 (13)
O3	0.103 (2)	0.0541 (16)	0.0224 (10)	0.0415 (15)	−0.0067 (11)	0.0049 (10)
C1	0.0240 (11)	0.0279 (14)	0.0213 (11)	−0.0035 (10)	−0.0028 (9)	0.0015 (10)
C2	0.0282 (13)	0.0451 (18)	0.0215 (12)	0.0037 (12)	0.0013 (10)	0.0077 (11)
C3	0.0433 (16)	0.0393 (18)	0.0234 (13)	0.0103 (13)	−0.0034 (11)	−0.0001 (11)
C4	0.0259 (12)	0.0319 (15)	0.0211 (11)	0.0004 (11)	0.0000 (9)	0.0074 (10)
C4A	0.0244 (11)	0.0230 (13)	0.0209 (11)	−0.0034 (10)	−0.0032 (9)	0.0035 (9)
C5	0.0274 (12)	0.0279 (14)	0.0254 (12)	−0.0009 (10)	−0.0016 (9)	0.0029 (10)
C5A	0.0267 (12)	0.0223 (13)	0.0200 (11)	−0.0048 (10)	−0.0037 (9)	0.0025 (9)
C6	0.0334 (13)	0.0349 (16)	0.0259 (13)	0.0017 (12)	0.0033 (10)	−0.0001 (11)
C7	0.0415 (15)	0.0333 (16)	0.0193 (11)	−0.0027 (12)	−0.0009 (10)	0.0013 (11)
C8	0.0353 (13)	0.0285 (15)	0.0203 (12)	−0.0019 (11)	−0.0062 (10)	0.0020 (10)
C8A	0.0268 (12)	0.0240 (13)	0.0213 (11)	−0.0033 (10)	−0.0040 (9)	0.0007 (10)
N9	0.0278 (11)	0.0250 (12)	0.0186 (10)	0.0007 (9)	−0.0043 (8)	0.0003 (8)
C9A	0.0274 (12)	0.0237 (13)	0.0183 (11)	−0.0049 (10)	−0.0035 (9)	0.0024 (9)
C10	0.0376 (14)	0.0441 (18)	0.0207 (12)	0.0060 (13)	−0.0035 (10)	0.0014 (11)
C11	0.101 (3)	0.040 (2)	0.0337 (17)	0.013 (2)	−0.0184 (18)	0.0118 (14)
C12	0.053 (2)	0.083 (3)	0.076 (3)	−0.005 (2)	−0.022 (2)	0.041 (2)

Geometric parameters (Å, º) top

O1—C1	1.227 (3)	C6—C5	1.375 (4)
O2—C10	1.180 (3)	C6—H6	0.9500
O3—C10	1.315 (4)	C7—C6	1.415 (4)
O3—C11	1.464 (4)	C7—C8	1.366 (4)
C1—C9A	1.438 (3)	C7—H7	0.9500
C2—C1	1.508 (3)	C8—C8A	1.400 (3)
C2—H2A	0.9900	C8—H8	0.9500
C2—H2B	0.9900	C8A—N9	1.359 (3)
C3—C2	1.539 (4)	C8A—C5A	1.423 (3)
C3—C4	1.501 (4)	N9—H9	0.82 (4)
C3—C10	1.521 (4)	C9A—C4A	1.378 (4)
C3—H3	1.0000	C9A—N9	1.378 (3)
C4—C4A	1.500 (3)	C11—C12	1.446 (6)
C4—H4A	0.9900	C11—H11A	0.9900
C4—H4B	0.9900	C11—H11B	0.9900
C5—C5A	1.399 (4)	C12—H12A	0.9800
C5—H5	0.9500	C12—H12B	0.9800
C5A—C4A	1.423 (3)	C12—H12C	0.9800

C10—O3—C11	116.7 (3)	C5—C6—H6	119.6
O1—C1—C2	121.3 (2)	C7—C6—H6	119.6
O1—C1—C9A	124.2 (2)	C6—C7—H7	119.3
C9A—C1—C2	114.5 (2)	C8—C7—C6	121.5 (2)
C1—C2—C3	115.5 (2)	C8—C7—H7	119.3
C1—C2—H2A	108.4	C7—C8—C8A	118.0 (2)
C1—C2—H2B	108.4	C7—C8—H8	121.0
C3—C2—H2A	108.4	C8A—C8—H8	121.0
C3—C2—H2B	108.4	N9—C8A—C5A	108.9 (2)
H2A—C2—H2B	107.5	N9—C8A—C8	129.8 (2)
C2—C3—H3	106.4	C8—C8A—C5A	121.4 (2)
C4—C3—C2	114.9 (2)	C8A—N9—C9A	108.1 (2)
C4—C3—C10	114.8 (2)	C8A—N9—H9	130 (3)
C4—C3—H3	106.4	C9A—N9—H9	122 (3)
C10—C3—C2	107.3 (2)	N9—C9A—C1	125.0 (2)
C10—C3—H3	106.4	C4A—C9A—N9	110.1 (2)
C3—C4—H4A	109.7	C4A—C9A—C1	124.8 (2)
C3—C4—H4B	109.7	O2—C10—O3	123.2 (3)
C4A—C4—C3	110.0 (2)	O2—C10—C3	123.6 (3)
C4A—C4—H4A	109.7	O3—C10—C3	113.3 (2)
C4A—C4—H4B	109.7	O3—C11—H11A	109.3
H4A—C4—H4B	108.2	O3—C11—H11B	109.3
C5A—C4A—C4	130.1 (2)	C12—C11—O3	111.7 (3)
C9A—C4A—C4	123.2 (2)	C12—C11—H11A	109.3
C9A—C4A—C5A	106.7 (2)	C12—C11—H11B	109.3
C5A—C5—H5	120.4	H11A—C11—H11B	107.9
C6—C5—C5A	119.2 (2)	C11—C12—H12A	109.5
C6—C5—H5	120.4	C11—C12—H12B	109.5
C4A—C5A—C8A	106.1 (2)	C11—C12—H12C	109.5
C5—C5A—C4A	134.8 (2)	H12A—C12—H12B	109.5
C5—C5A—C8A	119.1 (2)	H12A—C12—H12C	109.5
C5—C6—C7	120.8 (3)	H12B—C12—H12C	109.5

C11—O3—C10—O2	−5.3 (5)	C5—C5A—C4A—C4	5.2 (5)
C11—O3—C10—C3	175.9 (3)	C5—C5A—C4A—C9A	−177.5 (3)
C10—O3—C11—C12	88.6 (5)	C8A—C5A—C4A—C4	−176.3 (3)
O1—C1—C9A—N9	−0.6 (4)	C8A—C5A—C4A—C9A	1.0 (3)
O1—C1—C9A—C4A	179.6 (2)	C7—C6—C5—C5A	0.9 (4)
C2—C1—C9A—N9	−176.9 (2)	C8—C7—C6—C5	−2.0 (4)
C2—C1—C9A—C4A	3.2 (4)	C6—C7—C8—C8A	0.2 (4)
C3—C2—C1—O1	158.9 (3)	C7—C8—C8A—N9	−178.9 (3)
C3—C2—C1—C9A	−24.5 (4)	C7—C8—C8A—C5A	2.7 (4)
C4—C3—C2—C1	46.9 (4)	N9—C8A—C5A—C4A	−1.2 (3)
C10—C3—C2—C1	175.9 (2)	N9—C8A—C5A—C5	177.5 (2)
C2—C3—C4—C4A	−44.0 (3)	C8—C8A—C5A—C4A	177.5 (2)
C10—C3—C4—C4A	−169.1 (2)	C8—C8A—C5A—C5	−3.7 (4)
C2—C3—C10—O2	36.0 (5)	C8—C8A—N9—C9A	−177.6 (3)
C2—C3—C10—O3	−145.3 (3)	C5A—C8A—N9—C9A	1.0 (3)
C4—C3—C10—O2	165.0 (3)	C1—C9A—N9—C8A	179.8 (2)
C4—C3—C10—O3	−16.3 (4)	C4A—C9A—N9—C8A	−0.4 (3)
C3—C4—C4A—C5A	−159.6 (3)	N9—C9A—C4A—C4	177.1 (2)
C3—C4—C4A—C9A	23.5 (4)	N9—C9A—C4A—C5A	−0.4 (3)
C6—C5—C5A—C4A	−179.8 (3)	C1—C9A—C4A—C4	−3.1 (4)
C6—C5—C5A—C8A	1.8 (4)	C1—C9A—C4A—C5A	179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱ	0.82 (4)	2.08 (4)	2.834 (3)	154 (4)
C4—H4A···Cg3ⁱⁱ	0.99	2.75	3.727 (3)	171

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₃
M_r	257.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.6811 (3), 8.7378 (5), 24.8310 (14)
β (°)	93.208 (4)
V (Å³)	1230.69 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	9148, 3004, 2145
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.221, 1.05
No. of reflections	3004
No. of parameters	177
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.42

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱ	0.82 (4)	2.08 (4)	2.834 (3)	154 (4)
C4—H4A···Cg3ⁱⁱ	0.99	2.75	3.727 (3)	171

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z.

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer.

References

Abraham, D. J. (1975). The Catharanthus Alkaloids, edited by W. I. Taylor & N. R. Fransworth, chs. 7 and 8. New York: Marcel Decker. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Çaylak, N., Hökelek, T., Uludağ, N. & Patır, S. (2007). Acta Cryst. E63, o3913–o3914. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chakraborty, D. P. & Roy, S. (1991). Progress in the Chemistry of Organic Natural Products, edited by W. Herz, G. W. Kirby, W. Steglich & Ch. Tamm, Vol. 57, pp. 71–152. Wien, New York: Springer-Verlag. Google Scholar
Chang, C. E. (1977). Flora of Taiwan, Vol. 3, pp. 520–523. Tapei, Taiwan: Poch Publishing Co. Ltd. Google Scholar
Ergün, Y., Patir, S. & Okay, G. (2004). Synth. Commun. 34, 435–442. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kondo, S., Katayama, M. & Marumo, S. (1986). J. Antibiot. 39, 727–730. CrossRef CAS PubMed Web of Science Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Phillipson, J. D. & Zenk, M. H. (1980). Indole and Biogenetically Related Alkaloids, ch 3. New York: Academic Press. Google Scholar
Saxton, J. E. (1983). Editor. Heterocyclic Compounds, Vol. 25, The Monoterpenoid Indole Alkaloids, chs. 8 and 11. New York: Wiley. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Te Paske, M. R., Gloer, J. B., Wicklow, D. T. & Dowd, P. F. (1989a). J. Org. Chem. 54, 4743–4746. CrossRef CAS Web of Science Google Scholar
Te Paske, M. R., Gloer, J. B., Wicklow, D. T. & Dowd, P. F. (1989b). Tetrahedron Lett. 30, 5965–5968. CrossRef CAS Web of Science Google Scholar
Uludağ, N., Öztürk, A., Hökelek, T. & Erdoğan, Ü. I. (2009). Acta Cryst. E65, o595–o596. Web of Science CSD CrossRef IUCr Journals Google Scholar