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

Gündoğdu, C.; Göçmentürk, M.; Ergün, Y.; Tercan, B.; Hökelek, T.

doi:10.1107/S1600536811018678

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1470-o1471

doi:10.1107/S1600536811018678

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

Cevher Gündoğdu,^a Mustafa Göçmentürk,^a Yavuz Ergün,^a Barış Tercan ^b and Tuncer Hökelek ^c ^*

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

(Received 13 May 2011; accepted 17 May 2011; online 20 May 2011)

In the title compound, C₁₅H₁₅NO₃, the carbazole skeleton includes 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 0.89 (4)°. The cyclohexenone ring has an envelope conformation. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three dimensional network. A weak C—H⋯π interaction 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_r = 257.28
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.102
S = 1.04
2993 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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/S1600536811018678/hb5881sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811018678/hb5881Isup3.cml

checkCIF report

Comment top

Tetrahydrocarbazole systems are present in the framework of a number of indole-type alkaloids of biological interest (Saxton, 1983). The structures of tricyclic, tetracyclic and pentacyclic ring systems with dithiolane and other substituents of the tetrahydrocarbazole core, have been reported previously (Hökelek et al., 1994; Patır et al., 1997; Hökelek et al., 1998; Hökelek et al., 1999; Hökelek & Patır, 1999). Although 4-oxo-tetrahydrocarbazoles rarely occur in nature, they have been increasingly important intermediates in the syntheses of indole or carbazole alkaloids and various biologically active heterocyclic compounds because of their unique structures. For instance, 4-oxo-tetrahydrocarbazole was used in the syntheses of antiemetic drugs, central nervous system active drugs and NPY-1 antagonists (Kumar et al., 2008). They have also been used in the syntheses of indole alkaloids (Ergün et al., 2002). Tetrahydrocarbazolone based antitumor active compounds and inhibitors of HIV integrase were synthesized from 4-oxo-tetrahydrocarbazoles (Li & Vince, 2006). The present study was undertaken to ascertain the crystal structure of the title compound, (I).

The molecule of the title compound contains a carbazole skeleton with an ethoxycarbonyl group at the 3 position, (Fig. 1), where the bond lengths are close to standard values (Allen et al., 1987) and generally agree with those in the previously reported compounds. In all structures atom N9 is substituted.

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 -0.012 (1) Å for atom C5a] with dihedral angle of B/C = 0.89 (4)°. Ring A (C1—C4/C4a/C9a) adopts envelope conformation with atom C2 displaced by -0.632 (2) 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), 3,3-ethylenedithio-3,3a,4,5,10,10b-hexahydro-2H-furo[2,3-a]carbazole (Uludağ et al., 2009) and ethyl 1-oxo-1,2,3,4-tetrahydro-9H-carbazole-3-carboxylate (Hökelek et al., 2009).

In the crystal, intermolecular N—H···O and C—H···O hydrogen bonds link the molecules into a three dimensional network (Table 1 and Fig. 2). There also exists a weak C—H···π interaction (Table 1).

Related literature top

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 top

A solution of 2,3-dichloro -5,6-dicyano-p-benzoquinone (9.36 g, 41.20 mmol) in tetrahydrofuran (20 ml, 90%) was added dropwise to a solution of ethyl 2,3,4,9-tetrahydro-1H -carbazole-3-carboxylate (5.00 g, 20.60 mmol) in tetrahydrofuran (50 ml, 90%) at 268 K. The reaction mixture was stirred for 10 min at 268 K, and then the solution was poured into sodium hydroxide (500 ml, 10%) and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by chromatography using silica gel and ethyl acetate. After the solvent was evaporated, the product was crystallized from ether to yield colourless blocks of (I) (yield; 0.58 g, 11%, m.p. 396 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 (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the crystal packing of the title compound. The N—H···O and C—H···O hydrogen bonds are shown as dashed lines [H-atoms not involved in hydrogen bonding have been omitted for clarity].

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

Crystal data top

C₁₅H₁₅NO₃	F(000) = 1088
M_r = 257.28	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	2993 independent reflections
Radiation source: fine-focus sealed tube	2258 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→9
T_min = 0.960, T_max = 0.981	k = −16→8
12029 measured reflections	l = −20→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)] = 0.042	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(F_o²) + (0.044P)² + 0.6029P] where P = (F_o² + 2F_c²)/3
2993 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₅NO₃	V = 2473.89 (13) Å³
M_r = 257.28	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.1057 (3) Å	µ = 0.10 mm⁻¹
b = 12.7031 (4) Å	T = 100 K
c = 21.3874 (5) Å	0.43 × 0.26 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2993 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2258 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.981	R_int = 0.033
12029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
2993 reflections	Δρ_min = −0.25 e Å⁻³
177 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2; (iii) −x−1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₃
M_r	257.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	9.1057 (3), 12.7031 (4), 21.3874 (5)
V (Å³)	2473.89 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.43 × 0.26 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.960, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	12029, 2993, 2258
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.102, 1.04
No. of reflections	2993
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)	0.28, −0.25

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

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) −x, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2; (iii) −x−1/2, y−1/2, 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

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Volume 67| Part 6| June 2011| Pages o1470-o1471

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