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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Page o2156
doi:10.1107/S1600536808033850

2,2,9-Tri­methyl-2,3-di­hydro­pyrano[2,3-a]carbazol-4-(11H)-one

Makuteswaran Sridharan,a Karnam J. Rajendra Prasada and Matthias Zellerb*

aDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India, and bDepartment of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH 44555, USA
*Correspondence e-mail: mzeller@cc.ysu.edu

(Received 22 September 2008; accepted 16 October 2008; online 22 October 2008)

The title compound, C18H17NO2, was prepared from 1-hydr­oxy-7-methyl­carbazole and 3,3-dimethyl­acrylic acid with trifluoro­acetic acid as the cyclization catalyst. The mol­ecules contain an essentially planar 6-methyl­indole unit. The second aromatic ring is significantly bent away from the plane of this unit, with maximum deviations of 0.171 (1) and 0.185 (1) Å for two of the C atoms. In the crystal structure, there are neither N—H⋯O hydrogen bonds nor π–π stacking between the aromatic sections of neighboring mol­ecules. There is only one weak C—H⋯O hydrogen bond and a number of weak C—H⋯π inter­actions.

Related literature

Knölker & Reddy (2002[Knölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303-4427.]) report on the isolation of pyran­o­carbazoles from various plant species. Sridharan et al. (2007[Sridharan, M., Prasad, K. J. R. & Zeller, M. (2007). Acta Cryst. E63, o4344.]) describe the synthesis of compounds related to the title compound. Sridharan et al. (2008a[Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008a). Acta Cryst. E64, o2155.],b[Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o2157.]) report the structures of the 9-H and 10-methyl derivatives of the title compound.

[Scheme 1]

Experimental

Crystal data

  • C18H17NO2

  • Mr = 279.33

  • Monoclinic, P 21 /c

  • a = 8.6702 (7) Å

  • b = 6.1647 (5) Å

  • c = 26.617 (2) Å

  • β = 99.100 (1)°

  • V = 1404.7 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 (2) K

  • 0.57 × 0.48 × 0.24 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.883, Tmax = 0.980

  • 12327 measured reflections

  • 3044 independent reflections

  • 2708 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.098

  • S = 1.04

  • 3044 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C15—H15B⋯O2i 0.99 2.48 3.4034 (13) 155
N1—H1⋯Cg2ii 0.88 2.97 3.5822 (11) 128
C2—H2⋯Cg1ii 0.95 2.74 3.5332 (13) 141
C8—H8⋯Cg1iii 0.95 2.91 3.4124 (12) 114
C9—H9⋯Cg2iii 0.95 2.74 3.4372 (13) 130
Symmetry codes: (i) -x+1, -y+2, -z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]. Cg1 and Cg2 are the centroids of the N1/C1/C6/C7C12 and C1–C6 rings, respectively.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006[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.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033850/hb2804sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033850/hb2804Isup2.hkl

checkCIF report


Comment top

Carbazole alkaloids have been isolated from the taxonomically related higher plants of the genus Murraya, Glycosmis, and Clausena from the family Rutaceae. Among the carbazole alkaloids pyranocarbazole alkaloids play a very important role. In this class girinimbine was the first member of the pyrano[3,2-a]carbazole alkaloid family to be isolated from M. Koenigii Spreng (Knölker & Reddy, 2002, and references therein). The isolation of these classes of compounds became an active area of study since these compounds possess high levels of biological and pharmacological activity. Hence we attempted to synthesize pyranocarbazoles by a simple and efficient route.

Using trifluoroacetic acid as the acylating agent we had been able to synthezize in high yields a range of pyranocarbazolones and we recently reported (Sridharan et al., 2007) the synthesis and crystallographic behaviour of 2,3-dihydro-2,2,8-trimethylpyrano[2,3-a]carbazol-4-(11H)-one. As an extension of this reasearch, and to further proof the credibility of trifluoroacetic acid as a good acylating agent, we further extended this synthetic route with a series of substituted 1-hydroxycarbazoles. The components thus synthesized were used as starting synthons to develop routes towards substituted pyranocarbazole derivatives. Herein we report the crystal structures of the title compound, (I).

The molecules in (I) consist of an essential planar 6-methyl-indole unit made up of the atoms C1 to C7, C12 and N1. Also in plane with this unit are the atoms C8, C11 and O1, and the overall r.m.s. deviation from planarity for these atoms is 0.0319 Å. In the structures of two related compounds (Sridharan et al., 2008a and 2008b) differentiated from the title compound only by the presence and/or position of one methyl group, the molecules were essentially planar with the only exception being the atoms of the C(CH3)2 unit of the pyranone rings. For the title compound, however, the remainder of the molecule, including the atoms C9 and C10 of the second aromatic six membered ring, are all deviating from the plane formed by the indole subunit. The aromatic ring is signifcantely bent away from this plane with C9 and C10 being displaced by 0.171 (1) and 0.185 (1) Å, respectively.

Differences between (I) and the two related structures (Sridharan et al., 2008a and 2008b) extend into the crystal packing as well. The other compounds are dominated by strong N—H···O hydrogen bonds and also exhibit a range of π–π stacking as well as weak C—H···O interactions. The title compound, however, while only being differentiated from the other two molecules by the presence and/or position of one methyl group, does not exhibit any strong N—H···O hydrogen bonds and it also does not exhibit any π–π stacking between the aromatic sections of neighboring molecules. There is only one weak C—H···O hydrogen bond (Table 1). Other intermolecular interactions are limited to even weaker C—H···π interactions (Table 1, Figure 3). Centroids given in Table 1 are defined as follows: Cg1: the pyrrol ring (N1, C1, C6, C7, C12); Cg2: C1 to C6; Cg3: C7 to C12

In the absence of stronger interactions the large number of these contacts dominates the packing forces. Molecules within the unit cell are rougly aligned along the long axis of the unit cell (the c axis) and neighboring molecules are twisted against each other so that their planes are approximately perpendicular to each other, thus allowing the C—H···π interactions to establish themselves as shown in Figure 3. Each molecule is both C—H donor towards two neighboring molecules and C—H acceptor for two other neighbors. In combination this creates layers of molecules connected by C—H···π interactions. Each layer is in turn connected with parallel layers by weak C—H···O hydrogen bonds as shown in Figure 4.

Related literature top

Knölker & Reddy (2002) report on the isolation of pyranocarbazoles from various plant species. Sridharan et al. (2007) describe the synthesis of compounds related to the title compound. Sridharan et al. (2008a, 2008b) report the structures of the 9-H and 10-methyl derivatives of the title compound.

Experimental top

1-hydroxy-7-methylcarbazole (0.001 mol) dissolved in 10 ml of trifluoroaceticacid was heated with 3,3-dimethylacrylicacid (0.001 mol) at 323 K for 5 h. The reaction was monitored by TLC. After completion of the reaction, the excess trifluroaceticacid was removed using rotary evaporation. The solid that precipitated out was poured onto ice water, then extracted using ethyl acetate and dried over anhydrous sodium sulfate and filtered. Then the solvent was removed under vacuum and the residue was purified by column chromatography on silica gel using petroleum ether/ ethyl acetate (95:5 v/v) as the eluant. Evaporation of solvent afforded yellow crystals which were recrystallized from ethanol to yield yellow blocks of (I) (0.262 g, 94%), m.p. 463–465 K.

Refinement top

All hydrogen atoms were added in calculated positions with C—H bond distances of 0.99 (methylene), 0.95 (aromatic) and 0.98 Å (methyl) and an N—H distance of 0.88 Å. They were refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (CCDC, 2007); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Reaction sequence
[Figure 2] Fig. 2. The molecular structure of (I) showing xx% displacement ellipsoids. H atoms are represented in stick mode.
[Figure 3] Fig. 3. Packing view of (I) showing part of one of the layers held together by C—H···π interactions. Blue dashed lines indicate short N/C—H···C contacts, green dashed lines indicate N/C—H contacts towards centers of aromatic rings as defined in Table 1.
[Figure 4] Fig. 4. Packing view showing two of the layers held together by C—H···π interactions and the C—H···O hydrogen bonds between the layers. Blue dashed lines indicate short C—H···O contacts
2,2,9-Trimethyl-2,3-dihydropyrano[2,3-a]carbazol-4-(11H)-one top
Crystal data top
C18H17NO2F(000) = 592
Mr = 279.33Dx = 1.321 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5407 reflections
a = 8.6702 (7) Åθ = 2.4–27.0°
b = 6.1647 (5) ŵ = 0.09 mm−1
c = 26.617 (2) ÅT = 100 K
β = 99.100 (1)°Block, yellow
V = 1404.7 (2) Å30.57 × 0.48 × 0.24 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		3044 independent reflections
Radiation source: fine-focus sealed tube2708 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −10→11
Tmin = 0.883, Tmax = 0.980k = −7→7
12327 measured reflectionsl = −33→33
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0431P)2 + 0.5637P]
where P = (Fo2 + 2Fc2)/3
3044 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C18H17NO2V = 1404.7 (2) Å3
Mr = 279.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.6702 (7) ŵ = 0.09 mm−1
b = 6.1647 (5) ÅT = 100 K
c = 26.617 (2) Å0.57 × 0.48 × 0.24 mm
β = 99.100 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		3044 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		2708 reflections with I > 2σ(I)
Tmin = 0.883, Tmax = 0.980Rint = 0.031
12327 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å−3
3044 reflectionsΔρmin = −0.21 e Å−3
193 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
xyzUiso*/Ueq
C10.17131 (13)0.84678 (19)0.25979 (4)0.0187 (2)
C20.09703 (13)0.7573 (2)0.29780 (4)0.0211 (3)
H20.04870.61880.29340.025*
C30.09548 (13)0.8752 (2)0.34216 (4)0.0226 (3)
C40.16617 (13)1.0821 (2)0.34766 (4)0.0234 (3)
H40.16201.16280.37780.028*
C50.24143 (13)1.1703 (2)0.31029 (4)0.0214 (3)
H50.28941.30900.31480.026*
C60.24560 (12)1.05129 (18)0.26567 (4)0.0182 (2)
C70.31598 (12)1.08697 (18)0.22066 (4)0.0183 (2)
C80.41054 (13)1.25324 (19)0.20595 (4)0.0211 (3)
H80.43261.37960.22620.025*
C90.47011 (13)1.2281 (2)0.16144 (4)0.0224 (3)
H90.53741.33640.15160.027*
C100.43349 (13)1.04460 (19)0.12984 (4)0.0203 (2)
C110.33180 (13)0.88417 (18)0.14256 (4)0.0185 (2)
C120.27867 (12)0.90402 (18)0.18939 (4)0.0181 (2)
C130.01770 (15)0.7822 (2)0.38419 (5)0.0301 (3)
H13A−0.09330.82090.37840.045*
H13B0.06740.84130.41700.045*
H13C0.02840.62390.38460.045*
C140.50985 (13)1.0114 (2)0.08483 (4)0.0237 (3)
C150.47085 (14)0.7998 (2)0.05735 (4)0.0243 (3)
H15A0.54360.68610.07310.029*
H15B0.48570.81590.02140.029*
C160.30334 (14)0.72833 (19)0.05911 (4)0.0208 (2)
C170.27377 (17)0.5034 (2)0.03665 (5)0.0290 (3)
H17A0.34650.40030.05580.043*
H17B0.28950.50480.00100.043*
H17C0.16620.45980.03860.043*
C180.18336 (14)0.8888 (2)0.03275 (4)0.0229 (3)
H18A0.07790.83530.03450.034*
H18B0.19660.9043−0.00300.034*
H18C0.19831.03000.04970.034*
N10.19001 (11)0.76108 (16)0.21306 (4)0.0199 (2)
H10.15190.63660.20050.024*
O10.28283 (10)0.70934 (13)0.11287 (3)0.0218 (2)
O20.60210 (11)1.14169 (18)0.07137 (3)0.0341 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0168 (5)0.0229 (6)0.0158 (5)0.0018 (4)0.0006 (4)−0.0007 (4)
C20.0178 (5)0.0256 (6)0.0194 (6)−0.0015 (4)0.0019 (4)0.0010 (5)
C30.0165 (5)0.0332 (7)0.0179 (6)0.0040 (5)0.0020 (4)0.0021 (5)
C40.0209 (6)0.0308 (7)0.0178 (6)0.0048 (5)0.0005 (4)−0.0051 (5)
C50.0198 (5)0.0224 (6)0.0208 (6)0.0029 (4)−0.0008 (4)−0.0027 (5)
C60.0156 (5)0.0204 (6)0.0176 (5)0.0021 (4)−0.0007 (4)0.0005 (4)
C70.0169 (5)0.0203 (6)0.0165 (5)0.0018 (4)−0.0008 (4)0.0001 (4)
C80.0214 (6)0.0205 (6)0.0197 (6)−0.0028 (4)−0.0018 (4)0.0002 (4)
C90.0203 (5)0.0247 (6)0.0210 (6)−0.0045 (5)−0.0009 (4)0.0041 (5)
C100.0180 (5)0.0246 (6)0.0175 (5)0.0004 (4)0.0006 (4)0.0031 (4)
C110.0200 (5)0.0183 (5)0.0166 (5)0.0019 (4)0.0011 (4)0.0008 (4)
C120.0171 (5)0.0189 (5)0.0177 (5)0.0003 (4)0.0008 (4)0.0018 (4)
C130.0265 (6)0.0436 (8)0.0214 (6)−0.0001 (6)0.0075 (5)0.0010 (5)
C140.0189 (5)0.0342 (7)0.0174 (6)0.0005 (5)0.0006 (4)0.0054 (5)
C150.0247 (6)0.0308 (7)0.0185 (6)0.0064 (5)0.0067 (5)0.0027 (5)
C160.0276 (6)0.0210 (6)0.0147 (5)0.0014 (5)0.0061 (4)−0.0001 (4)
C170.0454 (8)0.0219 (6)0.0214 (6)0.0018 (5)0.0107 (5)−0.0023 (5)
C180.0246 (6)0.0238 (6)0.0195 (6)0.0017 (5)0.0014 (4)−0.0012 (5)
N10.0239 (5)0.0189 (5)0.0170 (5)−0.0037 (4)0.0043 (4)−0.0015 (4)
O10.0317 (4)0.0192 (4)0.0156 (4)−0.0020 (3)0.0069 (3)−0.0008 (3)
O20.0287 (5)0.0506 (6)0.0240 (5)−0.0135 (4)0.0072 (4)0.0010 (4)
Geometric parameters (Å, º) top
C1—N11.3845 (14)C11—C121.4010 (15)
C1—C21.3959 (16)C12—N11.3847 (14)
C1—C61.4132 (16)C13—H13A0.9800
C2—C31.3887 (17)C13—H13B0.9800
C2—H20.9500C13—H13C0.9800
C3—C41.4123 (18)C14—O21.2263 (15)
C3—C131.5079 (17)C14—C151.5078 (18)
C4—C51.3843 (17)C15—C161.5255 (17)
C4—H40.9500C15—H15A0.9900
C5—C61.4013 (16)C15—H15B0.9900
C5—H50.9500C16—O11.4744 (13)
C6—C71.4447 (15)C16—C171.5155 (17)
C7—C81.4064 (16)C16—C181.5239 (16)
C7—C121.4086 (16)C17—H17A0.9800
C8—C91.3739 (17)C17—H17B0.9800
C8—H80.9500C17—H17C0.9800
C9—C101.4156 (17)C18—H18A0.9800
C9—H90.9500C18—H18B0.9800
C10—C111.4016 (16)C18—H18C0.9800
C10—C141.4718 (16)N1—H10.8800
C11—O11.3638 (14)
N1—C1—C2129.29 (11)C3—C13—H13B109.5
N1—C1—C6108.89 (10)H13A—C13—H13B109.5
C2—C1—C6121.80 (10)C3—C13—H13C109.5
C3—C2—C1118.47 (11)H13A—C13—H13C109.5
C3—C2—H2120.8H13B—C13—H13C109.5
C1—C2—H2120.8O2—C14—C10123.03 (12)
C2—C3—C4119.90 (11)O2—C14—C15122.10 (11)
C2—C3—C13119.81 (12)C10—C14—C15114.83 (10)
C4—C3—C13120.28 (11)C14—C15—C16112.12 (10)
C5—C4—C3121.77 (11)C14—C15—H15A109.2
C5—C4—H4119.1C16—C15—H15A109.2
C3—C4—H4119.1C14—C15—H15B109.2
C4—C5—C6118.78 (11)C16—C15—H15B109.2
C4—C5—H5120.6H15A—C15—H15B107.9
C6—C5—H5120.6O1—C16—C17105.74 (9)
C5—C6—C1119.24 (11)O1—C16—C18108.67 (9)
C5—C6—C7133.95 (11)C17—C16—C18110.60 (10)
C1—C6—C7106.79 (10)O1—C16—C15108.32 (9)
C8—C7—C12120.57 (10)C17—C16—C15110.77 (10)
C8—C7—C6133.09 (11)C18—C16—C15112.48 (10)
C12—C7—C6106.29 (10)C16—C17—H17A109.5
C9—C8—C7118.24 (11)C16—C17—H17B109.5
C9—C8—H8120.9H17A—C17—H17B109.5
C7—C8—H8120.9C16—C17—H17C109.5
C8—C9—C10121.51 (11)H17A—C17—H17C109.5
C8—C9—H9119.2H17B—C17—H17C109.5
C10—C9—H9119.2C16—C18—H18A109.5
C11—C10—C9120.74 (11)C16—C18—H18B109.5
C11—C10—C14118.66 (11)H18A—C18—H18B109.5
C9—C10—C14120.47 (11)C16—C18—H18C109.5
O1—C11—C12117.93 (10)H18A—C18—H18C109.5
O1—C11—C10124.60 (10)H18B—C18—H18C109.5
C12—C11—C10117.46 (10)C1—N1—C12108.55 (9)
N1—C12—C11129.31 (10)C1—N1—H1125.7
N1—C12—C7109.45 (10)C12—N1—H1125.7
C11—C12—C7121.24 (10)C11—O1—C16115.16 (9)
C3—C13—H13A109.5
N1—C1—C2—C3179.15 (11)O1—C11—C12—N15.46 (17)
C6—C1—C2—C30.73 (17)C10—C11—C12—N1−173.73 (11)
C1—C2—C3—C40.88 (17)O1—C11—C12—C7−175.89 (10)
C1—C2—C3—C13−179.36 (10)C10—C11—C12—C74.92 (16)
C2—C3—C4—C5−1.64 (17)C8—C7—C12—N1177.69 (10)
C13—C3—C4—C5178.61 (11)C6—C7—C12—N10.03 (12)
C3—C4—C5—C60.72 (17)C8—C7—C12—C11−1.21 (16)
C4—C5—C6—C10.88 (16)C6—C7—C12—C11−178.86 (10)
C4—C5—C6—C7−177.44 (11)C11—C10—C14—O2−178.92 (11)
N1—C1—C6—C5179.66 (10)C9—C10—C14—O2−3.00 (18)
C2—C1—C6—C5−1.63 (16)C11—C10—C14—C15−1.16 (15)
N1—C1—C6—C7−1.60 (12)C9—C10—C14—C15174.76 (10)
C2—C1—C6—C7177.11 (10)O2—C14—C15—C16−148.09 (12)
C5—C6—C7—C82.2 (2)C10—C14—C15—C1634.13 (14)
C1—C6—C7—C8−176.28 (12)C14—C15—C16—O1−57.83 (12)
C5—C6—C7—C12179.42 (12)C14—C15—C16—C17−173.36 (10)
C1—C6—C7—C120.95 (12)C14—C15—C16—C1862.29 (13)
C12—C7—C8—C9−2.51 (16)C2—C1—N1—C12−176.93 (11)
C6—C7—C8—C9174.40 (11)C6—C1—N1—C121.64 (12)
C7—C8—C9—C102.39 (17)C11—C12—N1—C1177.74 (11)
C8—C9—C10—C111.44 (17)C7—C12—N1—C1−1.03 (12)
C8—C9—C10—C14−174.39 (11)C12—C11—O1—C16162.98 (10)
C9—C10—C11—O1175.84 (10)C10—C11—O1—C16−17.90 (15)
C14—C10—C11—O1−8.26 (17)C17—C16—O1—C11168.56 (10)
C9—C10—C11—C12−5.03 (16)C18—C16—O1—C11−72.69 (12)
C14—C10—C11—C12170.87 (10)C15—C16—O1—C1149.79 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···O2i0.992.483.4034 (13)155
N1—H1···Cg2ii0.882.973.5822 (11)128
C2—H2···Cg1ii0.952.743.5332 (13)141
C8—H8···Cg1iii0.952.913.4124 (12)114
C9—H9···Cg2iii0.952.743.4372 (13)130
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC18H17NO2
Mr279.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.6702 (7), 6.1647 (5), 26.617 (2)
β (°) 99.100 (1)
V (Å3)1404.7 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.57 × 0.48 × 0.24
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.883, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		12327, 3044, 2708
Rint0.031
(sin θ/λ)max (Å−1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.098, 1.04
No. of reflections3044
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.27, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), Mercury (CCDC, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···O2i0.992.483.4034 (13)155
N1—H1···Cg2ii0.882.973.5822 (11)128
C2—H2···Cg1ii0.952.743.5332 (13)141
C8—H8···Cg1iii0.952.913.4124 (12)114
C9—H9···Cg2iii0.952.743.4372 (13)130
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

The authors acknowledge UGC, New Delhi, India, for the award of Major Research Project (grant No. F31-122/2005). MS thanks UGC, New Delhi, India, for the award of a research fellowship. The diffractometer was funded by the NSF (grant No. 0087210), the Ohio Board of Regents (grant No. CAP-491) and by YSU.

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationKnölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303–4427.  Web of Science PubMed Google Scholar
 First citationMacrae, 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
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSridharan, M., Prasad, K. J. R. & Zeller, M. (2007). Acta Cryst. E63, o4344.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008a). Acta Cryst. E64, o2155.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o2157.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 64| Part 11| November 2008| Page o2156
doi:10.1107/S1600536808033850
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