11-Butyl-3-meth­oxy-11H-benzo[a]carbazole

Ergün, Y.; Gündoğdu, C.; Tercan, B.; Ermiş, E.; Hökelek, T.

doi:10.1107/S1600536810021963

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1634-o1635

doi:10.1107/S1600536810021963

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11-Butyl-3-methoxy-11H-benzo[a]carbazole

Yavuz Ergün,^a Cevher Gündoğdu,^a Barış Tercan,^b Emel Ermiş ^c and Tuncer Hökelek ^d ^*

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

(Received 27 May 2010; accepted 8 June 2010; online 16 June 2010)

The title compound, C₂₁H₂₁NO, consists of a carbazole skeleton with a methoxybenzene ring fused to the carbazole, and a butyl group attached to the carbazole N atom. The carbazole skeleton is nearly planar [maximum deviation = 0.078 (2) Å], and it is oriented at a dihedral angle of 4.22 (4)° with respect to the adjacent methoxybenzene ring.

Related literature

For the biological activity of carbazole derivatives, see: Knölker & Reddy (2002 ). For the use of carbazole derivatives in the syntheses of indole alkaloids, see: Routier et al. (2001 ). For the use of benzo[a]carbazoles in cancer treatment, see: Carini et al. (2001 ). For the antitumor activity of a series of simple benzo[a]carbazoles against mammary tumors of rats, leukemia, renal tumors, colon cancer and malignant melanoma tumor cell lines, see: von Angerer & Prekajac (1986 ); Pindur & Lemster (1997 ). For the extensive application of benzo[a]carbazole derivatives as photographic materials, see: Oliveira et al. (2005 . For tetrahydrocarbazole systems present in the frameworks of a number of indole-type alkaloids of biological interest, see: Phillipson & Zenk (1980 ); Saxton (1983 ); Abraham (1975 ). For related structures, see: Hökelek et al. (1994 , 1998 , 1999 , 2004 , 2006 ); Patır et al. (1997 ); Hökelek & Patır (1999 , 2002 ); Çaylak et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₁NO
M_r = 303.39
Monoclinic, P 2₁
a = 10.7263 (6) Å
b = 5.5562 (3) Å
c = 13.8967 (7) Å
β = 97.841 (2)°
V = 820.46 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.48 × 0.39 × 0.35 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.965, T_max = 0.974
7947 measured reflections
2248 independent reflections
2001 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.04
2248 reflections
270 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.16 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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021963/xu2773sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021963/xu2773Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives display a range of biological activities, making them attractive compounds to synthetic and medicinal chemists (Knölker & Reddy, 2002). They also have an important role in the syntheses of indole alkaloids, in which their synthetic derivatives, possessing useful pharmacological properties, are currently under investigation (Routier et al., 2001). Benzo -annulated carbazole ring systems are found only rarely in natural products. The benzo[a]carbazoles, containing an aromatic ring fused to the a-face of the carbazole nucleus, are potential candidates for cancer treatment as a result of DNA intercelative binding properties (Carini et al., 2001). A series of simple benzo[a]carbazoles have been shown to bind to estrogen receptors and inhibit the growth of mammary tumors of rats (Angerer & Prekajac, 1986). Some benzo[a]carbazoles exhibit a pronounced antitumor activity against leukemia, renal tumor, colon cancer, and malignant melanoma tumor cell lines (Pindur & Lemster, 1997). Benzo[a]carbazole derivatives have also found extensive application as photographic materials (Oliveira et al., 2005).

Tetrahydrocarbazole systems are present in the framework of a number of indole-type alkaloids of biological interest (Phillipson & Zenk, 1980; Saxton, 1983; Abraham, 1975). The structures of tricyclic, tetracyclic and pentacyclic ring systems with dithiolane and other substituents of the tetrahydrocarbazole core, have been the subject of much interest in our laboratory. These include 1,2,3,4-tetrahydrocarbazole-1-spiro-2'-[1,3]dithiolane, (II) (Hökelek et al., 1994), N-(2-methoxyethyl)-N-{2,3,4,9-tetrahydrospiro[1H-carbazole-1, 2-(1,3)dithiolane]-4-yl}benzene-sulfonamide, (III) (Patır et al., 1997), spiro[carbazole-1(2H),2'-[1,3]-dithiolan]-4(3H)-one, (IV) (Hökelek et al., 1998), 9-acetonyl-3-ethylidene-1,2,3,4-tetrahydrospiro[carbazole-1,2'-[1,3] dithiolan]-4-one, (V) (Hökelek et al., 1999), N-(2,2-dimethoxyethyl)-N -{9-methoxymethyl-1,2,3,4-tetrahydrospiro[carbazole-1,2'-[1,3]dithiolan] -4-yl}benzamide, (VI) (Hökelek & Patır, 1999), 3a,4,10,10b-tetrahydro-2H -furo[2,3-a]carbazol-5(3H)-one, (VII) (Çaylak et al., 2007); also the pentacyclic compounds 6-ethyl-4-(2-methoxyethyl)-2,6-methano-5-oxo-hexahydro- pyrrolo(2,3 - d)carbazole-1-spiro-2'-(1,3)dithiolane, (VIII) (Hökelek & Patır, 2002), N-(2-benzyloxyethyl)-4,7-dimethyl-6-(1,3-dithiolan-2-yl)-1,2, 3,4,5,6-hexahydro-1,5-methano-2-azocino[4,3-b]indol-2-one, (IX) (Hökelek et al., 2004) and 4-ethyl-6,6-ethylenedithio-2-(2-methoxyethyl)-7-methoxy- methylene-2,3,4,5,6,7-hexahydro-1,5-methano-1H-azocino[4,3-b]indol-3-one, (X) (Hökelek et al., 2006). The title compound, (I), may be considered as a synthetic precursor of tetracyclic indole alkaloids of biological interests. The present study was undertaken to ascertain its crystal structure.

The title compound consists of a carbazole skeleton with a methoxy benzoato group fused to the a-face of the carbazole nucleus, and a butyl group attached to atom N9 (Fig. 1), where the bond lengths (Allen et al., 1987) and angles are within normal ranges, and generally agree with those in compounds (II)-(X). In all structures atom N9 is substituted.

An examination of the deviations from the least-squares planes through individual rings shows that rings A (C1—C4/C4a/C9a), B (C4a/C5a/C8a/N9/C9a), C (C5a/C5—C8/C8a) and D (C7/C8/C14—C17) are planar. The carbazole skeleton, containing the rings A, B and C are also nearly planar [with a maximum deviation of 0.078 (2) Å for atom C2] with dihedral angles of A/B = 2.37 (6), A/C = 5.01 (5) and B/C = 2.81 (5) ° Ring D is oriented with respect to the planar carbazole skeleton at a dihedral angle of 4.22 (4) °. So, it is nearly coplanar with the carbazole skeleton. Atoms O1 and C18 displaced by 0.010 (1) and -0.045 (2) Å from the plane of ring D, respectively, while atom C10 is 0.092 (2) Å away from the plane of the carbazole skeleton.

In the crystal structure, molecules are alongated along the c axis and stacked along the b axis (Fig. 2).

Related literature top

For the biological activity of carbazole derivatives, see: Knölker & Reddy (2002). For the use of carbazole derivatives in the syntheses of indole alkaloids, see: Routier et al. (2001). For the use of benzo[a]carbazoles in cancer treatment, see: Carini et al. (2001). For the antitumor activity of a series of simple benzo[a]carbazoles against mammary tumors of rats, leukemia, renal tumors, colon cancer and malignant melanoma tumor cell lines, see: von Angerer & Prekajac (1986); Pindur & Lemster (1997). For the extensive application of benzo[a]carbazole derivatives as photographic materials, see: Oliveira et al. (2005. For tetrahydrocarbazole systems present in the frameworks of a number of indole-type alkaloids of biological interest, see: Phillipson & Zenk (1980); Saxton (1983); Abraham (1975). For related structures, see: Hökelek et al. (1994, 1998, 1999, 2004, 2006); Patır et al. (1997); Hökelek & Patır (1999, 2002); Çaylak et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, (I), a solution of 3-methoxy-11H -benzo[a]carbazole (1.00 g, 4.0 mmol) in dichloromethane (20 ml) was cooled to 273 K, and then sodium hydroxide (2 ml, 50%), tetrabutylammonium hydrogen sulfate (0.10 g) and butyl bromide (0.62 g, 4.5 mmol) were added. The mixture was stirred for 1 h at 273 K, and then 2 h at 298 K. It was washed with hydrochloric acid (50 ml, 10%) and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from methanol (yield; 1.15 g, 93%, m.p. 369 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.

11-Butyl-3-methoxy-11H-benzo[a]carbazole top

Crystal data top

C₂₁H₂₁NO	F(000) = 324
M_r = 303.39	D_x = 1.228 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3840 reflections
a = 10.7263 (6) Å	θ = 2.3–28.4°
b = 5.5562 (3) Å	µ = 0.08 mm⁻¹
c = 13.8967 (7) Å	T = 100 K
β = 97.841 (2)°	Block, colorless
V = 820.46 (8) Å³	0.48 × 0.39 × 0.35 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2248 independent reflections
Radiation source: fine-focus sealed tube	2001 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→14
T_min = 0.965, T_max = 0.974	k = −7→6
7947 measured reflections	l = −17→18

Refinement top

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0528P)² + 0.1088P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2248 reflections	Δρ_max = 0.25 e Å⁻³
270 parameters	Δρ_min = −0.16 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₁H₂₁NO	V = 820.46 (8) Å³
M_r = 303.39	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.7263 (6) Å	µ = 0.08 mm⁻¹
b = 5.5562 (3) Å	T = 100 K
c = 13.8967 (7) Å	0.48 × 0.39 × 0.35 mm
β = 97.841 (2)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2248 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2001 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.974	R_int = 0.027
7947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	270 parameters
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.25 e Å⁻³
2248 reflections	Δρ_min = −0.16 e Å⁻³

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	0.59965 (11)	0.9420 (3)	−0.11895 (9)	0.0299 (3)
C1	1.02958 (17)	0.2221 (4)	0.41676 (13)	0.0246 (4)
H1	0.9764 (19)	0.094 (5)	0.4258 (15)	0.030 (6)*
C2	1.14448 (17)	0.2475 (4)	0.47538 (13)	0.0276 (4)
H2	1.166 (2)	0.136 (5)	0.5266 (17)	0.042 (7)*
C3	1.22609 (17)	0.4381 (4)	0.46185 (13)	0.0271 (4)
H3	1.3035 (19)	0.447 (4)	0.5040 (14)	0.022 (5)*
C4	1.19492 (16)	0.6061 (4)	0.38921 (13)	0.0245 (4)
H4	1.2520 (17)	0.742 (4)	0.3796 (13)	0.021 (5)*
C4A	1.08080 (15)	0.5806 (4)	0.32759 (12)	0.0217 (4)
C5	1.06152 (16)	0.9086 (4)	0.19246 (13)	0.0232 (4)
H5	1.1411 (18)	0.992 (4)	0.2181 (13)	0.020 (5)*
C5A	1.02208 (15)	0.7091 (3)	0.24338 (12)	0.0210 (4)
C6	0.98899 (16)	0.9848 (4)	0.10954 (13)	0.0238 (4)
H6	1.0136 (18)	1.120 (5)	0.0755 (14)	0.025 (5)*
C7	0.87121 (15)	0.8724 (4)	0.07581 (12)	0.0215 (4)
C8	0.82600 (15)	0.6754 (4)	0.12711 (12)	0.0205 (4)
C8A	0.90768 (15)	0.5921 (4)	0.21092 (12)	0.0197 (3)
C9A	0.99973 (15)	0.3887 (4)	0.34259 (12)	0.0214 (4)
N9	0.89451 (13)	0.3987 (3)	0.27259 (10)	0.0209 (3)
C10	0.79576 (15)	0.2165 (4)	0.26464 (13)	0.0221 (4)
H101	0.8331 (18)	0.076 (5)	0.2927 (14)	0.021 (5)*
H102	0.7675 (17)	0.185 (4)	0.1949 (14)	0.021 (5)*
C11	0.68345 (16)	0.2861 (4)	0.31519 (13)	0.0228 (4)
H111	0.7121 (18)	0.304 (4)	0.3868 (14)	0.023 (5)*
H112	0.6483 (19)	0.442 (5)	0.2886 (15)	0.027 (6)*
C12	0.58043 (17)	0.0964 (4)	0.29886 (15)	0.0290 (4)
H121	0.6196 (19)	−0.064 (5)	0.3171 (14)	0.025 (5)*
H122	0.5517 (19)	0.077 (5)	0.2304 (17)	0.036 (6)*
C13	0.47038 (18)	0.1518 (5)	0.35479 (16)	0.0397 (5)
H13A	0.4050	0.0290	0.3400	0.060*
H13B	0.4355	0.3104	0.3355	0.060*
H13C	0.5002	0.1516	0.4247	0.060*
C14	0.70388 (16)	0.5850 (4)	0.09343 (13)	0.0248 (4)
H14	0.668 (2)	0.458 (5)	0.1282 (15)	0.032 (6)*
C15	0.63327 (16)	0.6779 (4)	0.01272 (13)	0.0264 (4)
H15	0.549 (2)	0.613 (5)	−0.0092 (17)	0.044 (7)*
C16	0.68014 (16)	0.8672 (4)	−0.03944 (12)	0.0242 (4)
C17	0.79658 (16)	0.9641 (4)	−0.00876 (12)	0.0235 (4)
H17	0.8282 (16)	1.097 (4)	−0.0415 (13)	0.015 (5)*
C18	0.63988 (18)	1.1414 (4)	−0.17108 (14)	0.0325 (5)
H18A	0.5741	1.1833	−0.2245	0.049*
H18B	0.7172	1.0988	−0.1974	0.049*
H18C	0.6561	1.2794	−0.1272	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0241 (6)	0.0399 (9)	0.0257 (6)	0.0017 (6)	0.0027 (5)	0.0051 (7)
C1	0.0267 (9)	0.0213 (10)	0.0275 (8)	0.0008 (8)	0.0096 (7)	−0.0004 (8)
C2	0.0292 (9)	0.0284 (11)	0.0259 (9)	0.0058 (8)	0.0057 (7)	0.0023 (8)
C3	0.0228 (8)	0.0342 (12)	0.0250 (8)	0.0021 (8)	0.0062 (7)	−0.0029 (9)
C4	0.0212 (8)	0.0280 (11)	0.0253 (8)	−0.0024 (8)	0.0071 (6)	−0.0025 (8)
C4A	0.0222 (8)	0.0219 (9)	0.0223 (8)	0.0003 (7)	0.0077 (6)	−0.0039 (8)
C5	0.0215 (8)	0.0229 (9)	0.0263 (8)	−0.0032 (7)	0.0075 (7)	−0.0025 (8)
C5A	0.0197 (7)	0.0218 (9)	0.0229 (8)	0.0002 (7)	0.0072 (6)	−0.0024 (7)
C6	0.0262 (8)	0.0209 (9)	0.0261 (9)	−0.0032 (8)	0.0100 (7)	0.0006 (8)
C7	0.0215 (8)	0.0226 (10)	0.0220 (8)	0.0009 (7)	0.0088 (7)	−0.0025 (7)
C8	0.0207 (7)	0.0203 (9)	0.0215 (8)	0.0008 (7)	0.0065 (6)	−0.0024 (7)
C8A	0.0203 (7)	0.0178 (9)	0.0225 (8)	0.0001 (7)	0.0081 (6)	−0.0021 (7)
C9A	0.0199 (7)	0.0217 (9)	0.0239 (8)	0.0016 (7)	0.0076 (6)	−0.0015 (7)
N9	0.0204 (6)	0.0186 (8)	0.0240 (7)	−0.0017 (6)	0.0045 (5)	0.0000 (6)
C10	0.0210 (8)	0.0189 (9)	0.0269 (9)	−0.0034 (7)	0.0051 (7)	−0.0001 (8)
C11	0.0212 (8)	0.0226 (10)	0.0252 (9)	−0.0026 (7)	0.0054 (6)	0.0003 (7)
C12	0.0230 (8)	0.0338 (12)	0.0307 (10)	−0.0073 (8)	0.0051 (7)	−0.0015 (9)
C13	0.0246 (9)	0.0471 (15)	0.0491 (12)	−0.0051 (10)	0.0112 (8)	0.0041 (11)
C14	0.0247 (8)	0.0265 (10)	0.0240 (8)	−0.0033 (8)	0.0062 (6)	0.0006 (8)
C15	0.0201 (8)	0.0323 (11)	0.0272 (9)	−0.0018 (8)	0.0049 (7)	−0.0012 (8)
C16	0.0235 (8)	0.0286 (10)	0.0211 (8)	0.0045 (7)	0.0051 (7)	−0.0009 (8)
C17	0.0246 (8)	0.0240 (10)	0.0234 (8)	0.0005 (7)	0.0087 (6)	−0.0008 (8)
C18	0.0324 (9)	0.0366 (12)	0.0283 (9)	0.0040 (9)	0.0035 (8)	0.0064 (9)

Geometric parameters (Å, º) top

O1—C16	1.371 (2)	C10—C11	1.525 (2)
O1—C18	1.422 (3)	C10—H101	0.94 (2)
C1—C2	1.389 (3)	C10—H102	0.991 (19)
C1—H1	0.93 (2)	C11—C12	1.521 (3)
C2—C3	1.403 (3)	C11—H111	1.006 (19)
C2—H2	0.95 (3)	C11—H112	0.99 (3)
C3—C4	1.382 (3)	C12—C13	1.530 (3)
C3—H3	0.95 (2)	C12—H121	1.00 (2)
C4—H4	0.99 (2)	C12—H122	0.97 (2)
C4A—C4	1.402 (2)	C13—H13A	0.9800
C4A—C9A	1.410 (3)	C13—H13B	0.9800
C5—C5A	1.411 (3)	C13—H13C	0.9800
C5—H5	1.00 (2)	C14—C8	1.421 (2)
C5A—C4A	1.440 (2)	C14—H14	0.97 (2)
C6—C5	1.367 (3)	C15—C14	1.366 (3)
C6—H6	0.95 (2)	C15—H15	0.98 (2)
C7—C6	1.430 (2)	C16—C15	1.408 (3)
C8—C7	1.427 (2)	C16—C17	1.373 (3)
C8—C8A	1.435 (2)	C17—C7	1.423 (3)
C8A—C5A	1.408 (2)	C17—H17	0.96 (2)
C9A—C1	1.390 (3)	C18—H18A	0.9800
N9—C8A	1.393 (2)	C18—H18B	0.9800
N9—C9A	1.387 (2)	C18—H18C	0.9800
N9—C10	1.458 (2)

C16—O1—C18	116.45 (15)	N9—C10—H101	106.4 (12)
C2—C1—C9A	117.62 (18)	N9—C10—H102	108.7 (12)
C2—C1—H1	120.6 (13)	C11—C10—H101	109.8 (12)
C9A—C1—H1	121.7 (13)	C11—C10—H102	109.9 (11)
C1—C2—C3	121.20 (18)	H101—C10—H102	108.3 (19)
C1—C2—H2	119.0 (15)	C10—C11—H111	109.1 (11)
C3—C2—H2	119.8 (15)	C10—C11—H112	109.4 (12)
C2—C3—H3	117.8 (14)	C12—C11—C10	111.04 (16)
C4—C3—C2	120.97 (17)	C12—C11—H111	109.5 (13)
C4—C3—H3	121.2 (14)	C12—C11—H112	108.4 (13)
C3—C4—C4A	118.82 (18)	H112—C11—H111	109.4 (18)
C3—C4—H4	121.4 (11)	C11—C12—C13	112.32 (18)
C4A—C4—H4	119.8 (11)	C11—C12—H121	107.9 (12)
C4—C4A—C5A	134.01 (18)	C11—C12—H122	110.6 (15)
C4—C4A—C9A	119.40 (17)	C13—C12—H121	112.1 (12)
C9A—C4A—C5A	106.56 (14)	C13—C12—H122	111.0 (13)
C5A—C5—H5	119.3 (12)	H121—C12—H122	103 (2)
C6—C5—C5A	119.41 (17)	C12—C13—H13A	109.5
C6—C5—H5	121.3 (12)	C12—C13—H13B	109.5
C5—C5A—C4A	132.01 (16)	C12—C13—H13C	109.5
C8A—C5A—C4A	107.26 (16)	H13A—C13—H13B	109.5
C8A—C5A—C5	120.68 (16)	H13A—C13—H13C	109.5
C5—C6—C7	121.13 (17)	H13B—C13—H13C	109.5
C5—C6—H6	120.2 (12)	C8—C14—H14	120.6 (13)
C7—C6—H6	118.5 (12)	C15—C14—C8	121.32 (18)
C8—C7—C6	121.11 (16)	C15—C14—H14	118.1 (13)
C17—C7—C6	119.12 (17)	C14—C15—C16	120.52 (17)
C17—C7—C8	119.75 (16)	C14—C15—H15	120.0 (16)
C7—C8—C8A	116.20 (15)	C16—C15—H15	119.5 (15)
C14—C8—C7	117.85 (17)	O1—C16—C15	114.31 (16)
C14—C8—C8A	125.91 (17)	O1—C16—C17	125.26 (18)
C5A—C8A—C8	121.33 (16)	C17—C16—C15	120.42 (17)
N9—C8A—C5A	108.44 (15)	C7—C17—H17	118.4 (11)
N9—C8A—C8	130.23 (16)	C16—C17—C7	120.08 (18)
C1—C9A—C4A	121.96 (16)	C16—C17—H17	121.5 (11)
N9—C9A—C1	129.06 (17)	O1—C18—H18A	109.5
N9—C9A—C4A	108.98 (15)	O1—C18—H18B	109.5
C8A—N9—C10	128.47 (14)	O1—C18—H18C	109.5
C9A—N9—C8A	108.74 (14)	H18A—C18—H18B	109.5
C9A—N9—C10	122.57 (15)	H18A—C18—H18C	109.5
N9—C10—C11	113.60 (15)	H18B—C18—H18C	109.5

C18—O1—C16—C15	176.75 (16)	N9—C8A—C5A—C4A	0.40 (19)
C18—O1—C16—C17	−2.2 (3)	N9—C8A—C5A—C5	178.18 (16)
C9A—C1—C2—C3	1.6 (3)	C8—C8A—C5A—C4A	−179.64 (15)
C1—C2—C3—C4	−0.4 (3)	C8—C8A—C5A—C5	−1.9 (3)
C2—C3—C4—C4A	−1.2 (3)	N9—C9A—C1—C2	177.47 (17)
C5A—C4A—C4—C3	−176.09 (19)	C4A—C9A—C1—C2	−1.3 (3)
C9A—C4A—C4—C3	1.5 (2)	C9A—N9—C8A—C5A	−1.06 (18)
C4—C4A—C9A—N9	−179.24 (16)	C9A—N9—C8A—C8	178.97 (17)
C4—C4A—C9A—C1	−0.2 (2)	C10—N9—C8A—C5A	−175.70 (16)
C5A—C4A—C9A—N9	−1.06 (18)	C10—N9—C8A—C8	4.3 (3)
C5A—C4A—C9A—C1	177.96 (16)	C8A—N9—C9A—C1	−177.60 (17)
C6—C5—C5A—C4A	175.63 (18)	C8A—N9—C9A—C4A	1.33 (18)
C6—C5—C5A—C8A	−1.5 (3)	C10—N9—C9A—C1	−2.6 (3)
C5—C5A—C4A—C4	0.8 (3)	C10—N9—C9A—C4A	176.34 (15)
C5—C5A—C4A—C9A	−177.03 (18)	C9A—N9—C10—C11	96.69 (19)
C8A—C5A—C4A—C4	178.20 (19)	C8A—N9—C10—C11	−89.3 (2)
C8A—C5A—C4A—C9A	0.40 (19)	N9—C10—C11—C12	176.39 (15)
C7—C6—C5—C5A	2.7 (3)	C10—C11—C12—C13	175.83 (17)
C8—C7—C6—C5	−0.6 (3)	C15—C14—C8—C7	2.1 (3)
C17—C7—C6—C5	177.50 (17)	C15—C14—C8—C8A	179.73 (17)
C8A—C8—C7—C6	−2.6 (2)	C16—C15—C14—C8	−0.1 (3)
C8A—C8—C7—C17	179.29 (16)	O1—C16—C15—C14	179.77 (17)
C14—C8—C7—C6	175.24 (16)	C17—C16—C15—C14	−1.3 (3)
C14—C8—C7—C17	−2.8 (2)	O1—C16—C17—C7	179.31 (16)
C7—C8—C8A—N9	−176.22 (16)	C15—C16—C17—C7	0.5 (3)
C7—C8—C8A—C5A	3.8 (2)	C16—C17—C7—C6	−176.50 (16)
C14—C8—C8A—N9	6.1 (3)	C16—C17—C7—C8	1.6 (3)
C14—C8—C8A—C5A	−173.86 (17)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁NO
M_r	303.39
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	10.7263 (6), 5.5562 (3), 13.8967 (7)
β (°)	97.841 (2)
V (Å³)	820.46 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.39 × 0.35

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.965, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	7947, 2248, 2001
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.04
No. of reflections	2248
No. of parameters	270
No. of restraints	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

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 the diffractometer.

References

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