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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2,2,10-Tri­methyl-2,3-di­hydro­pyrano[2,3-a]carbazol-4(11H)-one

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-8-methyl­carbazole and 3,3-dimethyl­acrylic acid with trifluoro­acetic acid as the cyclization catalyst. Due to the –CMe2– group, the mol­ecule is not quite planar. The packing is dominated by the strong N—H⋯O hydrogen bonds and some weaker C—H⋯O and C—H⋯π inter­actions. ππ Stacking inter­actions [centroid–centroid separation = 3.806 (2) Å] join neighboring mol­ecules into loosely connected inversion dimers.

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, Rajendra Prasad & Zeller (2008[Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008). Acta Cryst. E64, o2155.]) report the structure of the 9-methyl derivative of the title compound. Sridharan, Rajendra Prasad, Ngendahimana et al. (2008[Sridharan, M., Prasad, K. J. R. & Zeller, M. (2008). Acta Cryst. E64, o2156.]) report the structure of the 10-H derivative of the title compound.

[Scheme 1]

Experimental

Crystal data
  • C18H17NO2

  • Mr = 279.33

  • Monoclinic, P 21 /c

  • a = 12.9740 (16) Å

  • b = 9.4195 (12) Å

  • c = 12.8444 (16) Å

  • β = 114.733 (2)°

  • V = 1425.7 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 (2) K

  • 0.53 × 0.43 × 0.19 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.886, Tmax = 0.984

  • 13755 measured reflections

  • 3526 independent reflections

  • 2941 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.109

  • S = 1.03

  • 3526 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.88 1.99 2.8634 (13) 173
C15—H15A⋯O1ii 0.99 2.59 3.5411 (15) 161
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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


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 in 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 two of the compounds thus obtained: 2,3-dihydro-2,2,9-trimethylpyrano[2,3-a]carbazol-4-(11H)-one (Sridharan, Rajendra Prasad & Zeller, 2008), the title compound of the preceeding article in this journal) and of the title compound 2,3-dihydro-2,2,10-trimethylpyrano[2,3-a]carbazol-4-(11H)-one (Figure 1).

The single-crystal structure confirmed the formation of the dihydropyrano-[2,3-a]carbazol-4(11H)-one framework as shown in Figure 2. Data collection and structure refinement were unproblematic and all structural parameters (bond lengths, angles, etc) are in the expected ranges. The molecules crystallize in a monoclinic setting in P21/c with four largely planar molecules per unit cell. The plane defined by the sp2 hybridized carbon atoms, the C1 methyl and C15 methylene carbon atoms, and the N and O atoms has an r.m.s. deviation from planarity of only 0.0754 Å. Of all the ring C atoms only C14 of the pyran C(Me)2 unit is significately out of plane with the atoms of the four fused rings, its deviation being 0.534 (1) Å. The pyran ring thus exhibits a half chair conformation.

One of the methyl groups of the C(Me)2 unit is also located close to the average plane of the molecule (C18 with a deviation of 0.125 (2) Å). The other, C17, is however located 2.039 (2) Å away from this plane and thus makes the molecule as a whole not planar and prevents it form forming extensive π-π stacked entities in the solid state. The packing is thus indeed dominated by strong N—H···O hydrogen bonds (Figure 3, Table 1) and some weaker C—H···O (Table 1, Figure 4) and C—H···π interactions (e.g. C18—H18b···Cg1ii = 2.94 Å with Cg1 being the ring C8 to C13 and ii = -x, -1/2 + y, 1/2 - z). The only significant π···π stacking interaction with a centroid to centroid distance of 3.806 (2) Å is found between the pyrrole ring and the the aromatic ring made up of C2 to C7 (Figure 4). Two neighboring molecules related by an inversion center are forming loosly connected dimers via two sets of these π-π interactions (symmetry operator 1 - x, 2 - y, 1 - z).

The structures of the 2,2-dimethyl and the 2,2,10-methyl derivatives of the title compound are described in Sridharan, Rajendra Prasad, Ngendahimana et al. (2008) and Sridharan, Rajendra Prasad & Zeller (2008), the two preceeding articles in this journal. For a more detailed comparison of structures and packing of the three two derivatives please see in Sridharan, Rajendra Prasad & Zeller (2008).

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, Rajendra Prasad & Zeller (2008) report the structure of the 9-methyl derivative of the title compound. Sridharan, Rajendra Prasad, Ngendahimana et al. (2008) report the structure of the 10-H derivative of the title compound.

Experimental top

1-hydroxy-8-methylcarbazole (0.001 mol) dissolved in 10 ml of trifluroaceticacid and 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 trifluroacetic acid 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 eluant to yield yellow plates of (I) (0.239 g, 86%), m.p. 475–477 K.

Refinement top

All hydrogen atoms were added in calculated positions with C—H = 0.99Å (methylene), 0.95Å (aromatic) and 0.98 Å (methyl) and N—H = 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. View of (I) showing xx% displacement ellipsoids. H atoms are represented in stick mode.
[Figure 3] Fig. 3. Packing view of (I) down the a axis showing chains built by the N—H···O hydrogen bonds (indicated by blue dashed lines).
[Figure 4] Fig. 4. Packing view of (I) showing the secondary C—H···π and C—H···O interactions indicated by green lines. Numbers given are distances in Å. N—H···O hydrogen bonds are omitted for clarity.
2,2,10-Trimethyl-2,3-dihydropyrano[2,3-a]carbazol-4(11H)-one top
Crystal data top
C18H17NO2F(000) = 592
Mr = 279.33Dx = 1.301 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4194 reflections
a = 12.9740 (16) Åθ = 2.8–31.5°
b = 9.4195 (12) ŵ = 0.09 mm1
c = 12.8444 (16) ÅT = 100 K
β = 114.733 (2)°Plate, yellow
V = 1425.7 (3) Å30.53 × 0.43 × 0.19 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3526 independent reflections
Radiation source: fine-focus sealed tube2941 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1717
Tmin = 0.886, Tmax = 0.984k = 1212
13755 measured reflectionsl = 1717
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.5237P]
where P = (Fo2 + 2Fc2)/3
3526 reflections(Δ/σ)max = 0.002
193 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C18H17NO2V = 1425.7 (3) Å3
Mr = 279.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.9740 (16) ŵ = 0.09 mm1
b = 9.4195 (12) ÅT = 100 K
c = 12.8444 (16) Å0.53 × 0.43 × 0.19 mm
β = 114.733 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
3526 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
2941 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.984Rint = 0.027
13755 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.03Δρmax = 0.31 e Å3
3526 reflectionsΔρmin = 0.26 e Å3
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
C10.30161 (12)1.23026 (14)0.61446 (11)0.0287 (3)
H1A0.32741.15800.67490.043*
H1B0.21991.21930.56800.043*
H1C0.31681.32490.64930.043*
C20.36377 (10)1.21263 (12)0.53998 (10)0.0205 (2)
C30.44870 (10)1.30290 (13)0.54197 (11)0.0235 (3)
H30.46981.38060.59390.028*
C40.50503 (11)1.28432 (13)0.47042 (11)0.0244 (3)
H40.56361.34840.47570.029*
C50.47647 (10)1.17431 (13)0.39258 (10)0.0217 (2)
H50.51421.16240.34370.026*
C60.39071 (10)1.08061 (12)0.38720 (10)0.0186 (2)
C70.33727 (9)1.09998 (12)0.46184 (10)0.0178 (2)
C80.25796 (9)0.90879 (12)0.35603 (9)0.0165 (2)
C90.33879 (9)0.95775 (12)0.31816 (10)0.0176 (2)
C100.35259 (10)0.88720 (13)0.22829 (10)0.0197 (2)
H100.40780.91840.20290.024*
C110.28477 (10)0.77237 (13)0.17803 (10)0.0199 (2)
H110.29320.72460.11690.024*
C120.20236 (10)0.72342 (12)0.21537 (10)0.0176 (2)
C130.19004 (9)0.79075 (12)0.30620 (10)0.0165 (2)
C140.06708 (10)0.60905 (12)0.32183 (10)0.0208 (2)
C150.03119 (10)0.58064 (13)0.19434 (10)0.0199 (2)
H15A0.00540.48100.17730.024*
H15B0.03380.64280.14930.024*
C160.12561 (10)0.60623 (12)0.15718 (10)0.0186 (2)
C170.15681 (12)0.50413 (14)0.39605 (11)0.0288 (3)
H17A0.22290.50950.37780.043*
H17B0.12550.40780.38110.043*
H17C0.17980.52750.47710.043*
C180.03389 (12)0.61299 (15)0.35277 (12)0.0302 (3)
H18A0.00850.64240.43290.045*
H18B0.06810.51830.34250.045*
H18C0.09020.68080.30290.045*
N10.25730 (8)0.99440 (10)0.44254 (8)0.0176 (2)
H10.21370.98380.47910.021*
O10.11424 (7)0.75262 (9)0.34888 (7)0.01967 (19)
O20.13335 (7)0.53564 (10)0.08062 (7)0.0245 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0343 (7)0.0268 (7)0.0265 (6)0.0040 (5)0.0145 (6)0.0059 (5)
C20.0223 (6)0.0185 (5)0.0189 (5)0.0003 (4)0.0068 (5)0.0011 (4)
C30.0256 (6)0.0190 (6)0.0220 (6)0.0024 (5)0.0061 (5)0.0003 (4)
C40.0227 (6)0.0229 (6)0.0251 (6)0.0052 (5)0.0076 (5)0.0031 (5)
C50.0201 (6)0.0238 (6)0.0215 (6)0.0018 (5)0.0090 (5)0.0040 (5)
C60.0187 (5)0.0185 (5)0.0182 (5)0.0004 (4)0.0074 (4)0.0025 (4)
C70.0173 (5)0.0168 (5)0.0185 (5)0.0008 (4)0.0068 (4)0.0031 (4)
C80.0177 (5)0.0170 (5)0.0160 (5)0.0018 (4)0.0083 (4)0.0024 (4)
C90.0175 (5)0.0179 (5)0.0182 (5)0.0002 (4)0.0083 (4)0.0032 (4)
C100.0192 (5)0.0229 (6)0.0209 (6)0.0001 (4)0.0122 (5)0.0022 (4)
C110.0214 (6)0.0230 (6)0.0191 (5)0.0014 (4)0.0121 (5)0.0002 (4)
C120.0181 (5)0.0185 (5)0.0182 (5)0.0008 (4)0.0096 (4)0.0011 (4)
C130.0163 (5)0.0176 (5)0.0177 (5)0.0015 (4)0.0090 (4)0.0024 (4)
C140.0255 (6)0.0189 (6)0.0219 (6)0.0073 (4)0.0137 (5)0.0034 (4)
C150.0200 (5)0.0218 (6)0.0200 (5)0.0038 (4)0.0104 (5)0.0035 (4)
C160.0199 (5)0.0197 (6)0.0177 (5)0.0019 (4)0.0093 (4)0.0019 (4)
C170.0388 (7)0.0219 (6)0.0242 (6)0.0039 (5)0.0117 (6)0.0022 (5)
C180.0349 (7)0.0347 (7)0.0312 (7)0.0148 (6)0.0237 (6)0.0103 (6)
N10.0196 (5)0.0175 (5)0.0183 (5)0.0013 (4)0.0106 (4)0.0008 (4)
O10.0229 (4)0.0189 (4)0.0231 (4)0.0050 (3)0.0155 (4)0.0034 (3)
O20.0277 (5)0.0264 (5)0.0239 (4)0.0031 (4)0.0153 (4)0.0064 (3)
Geometric parameters (Å, º) top
C1—C21.4963 (18)C11—C121.4195 (16)
C1—H1A0.9800C11—H110.9500
C1—H1B0.9800C12—C131.3945 (16)
C1—H1C0.9800C12—C161.4649 (16)
C2—C31.3836 (17)C13—O11.3594 (13)
C2—C71.4010 (16)C14—O11.4650 (13)
C3—C41.4040 (19)C14—C181.5202 (17)
C3—H30.9500C14—C171.5205 (18)
C4—C51.3787 (18)C14—C151.5270 (16)
C4—H40.9500C15—C161.5086 (16)
C5—C61.3991 (16)C15—H15A0.9900
C5—H50.9500C15—H15B0.9900
C6—C71.4103 (16)C16—O21.2254 (14)
C6—C91.4420 (16)C17—H17A0.9800
C7—N11.3826 (14)C17—H17B0.9800
C8—N11.3759 (14)C17—H17C0.9800
C8—C131.3966 (16)C18—H18A0.9800
C8—C91.4057 (15)C18—H18B0.9800
C9—C101.4068 (16)C18—H18C0.9800
C10—C111.3732 (17)N1—H10.8800
C10—H100.9500
C2—C1—H1A109.5C13—C12—C16118.57 (10)
C2—C1—H1B109.5C11—C12—C16121.31 (10)
H1A—C1—H1B109.5O1—C13—C12124.94 (10)
C2—C1—H1C109.5O1—C13—C8116.73 (10)
H1A—C1—H1C109.5C12—C13—C8118.31 (10)
H1B—C1—H1C109.5O1—C14—C18103.62 (9)
C3—C2—C7115.69 (11)O1—C14—C17108.49 (10)
C3—C2—C1123.92 (11)C18—C14—C17111.68 (11)
C7—C2—C1120.39 (11)O1—C14—C15109.02 (9)
C2—C3—C4122.68 (12)C18—C14—C15112.03 (10)
C2—C3—H3118.7C17—C14—C15111.62 (10)
C4—C3—H3118.7C16—C15—C14112.81 (9)
C5—C4—C3120.85 (11)C16—C15—H15A109.0
C5—C4—H4119.6C14—C15—H15A109.0
C3—C4—H4119.6C16—C15—H15B109.0
C4—C5—C6118.48 (11)C14—C15—H15B109.0
C4—C5—H5120.8H15A—C15—H15B107.8
C6—C5—H5120.8O2—C16—C12123.50 (11)
C5—C6—C7119.46 (11)O2—C16—C15121.14 (11)
C5—C6—C9133.93 (11)C12—C16—C15115.31 (10)
C7—C6—C9106.61 (10)C14—C17—H17A109.5
N1—C7—C2127.88 (11)C14—C17—H17B109.5
N1—C7—C6109.30 (10)H17A—C17—H17B109.5
C2—C7—C6122.81 (11)C14—C17—H17C109.5
N1—C8—C13128.38 (10)H17A—C17—H17C109.5
N1—C8—C9110.17 (10)H17B—C17—H17C109.5
C13—C8—C9121.44 (10)C14—C18—H18A109.5
C8—C9—C10119.89 (11)C14—C18—H18B109.5
C8—C9—C6105.94 (10)H18A—C18—H18B109.5
C10—C9—C6134.16 (11)C14—C18—H18C109.5
C11—C10—C9118.78 (10)H18A—C18—H18C109.5
C11—C10—H10120.6H18B—C18—H18C109.5
C9—C10—H10120.6C8—N1—C7107.97 (10)
C10—C11—C12121.47 (11)C8—N1—H1126.0
C10—C11—H11119.3C7—N1—H1126.0
C12—C11—H11119.3C13—O1—C14116.68 (9)
C13—C12—C11120.07 (11)
C7—C2—C3—C40.25 (18)C11—C12—C13—O1179.88 (10)
C1—C2—C3—C4179.51 (12)C16—C12—C13—O12.67 (17)
C2—C3—C4—C50.89 (19)C11—C12—C13—C81.94 (17)
C3—C4—C5—C60.60 (18)C16—C12—C13—C8175.51 (10)
C4—C5—C6—C70.79 (17)N1—C8—C13—O11.17 (17)
C4—C5—C6—C9179.38 (12)C9—C8—C13—O1179.73 (10)
C3—C2—C7—N1179.55 (11)N1—C8—C13—C12177.16 (11)
C1—C2—C7—N10.67 (19)C9—C8—C13—C121.39 (16)
C3—C2—C7—C61.70 (17)O1—C14—C15—C1653.97 (13)
C1—C2—C7—C6178.07 (11)C18—C14—C15—C16168.06 (10)
C5—C6—C7—N1179.03 (10)C17—C14—C15—C1665.85 (13)
C9—C6—C7—N10.84 (13)C13—C12—C16—O2176.05 (11)
C5—C6—C7—C22.02 (17)C11—C12—C16—O26.53 (18)
C9—C6—C7—C2178.11 (10)C13—C12—C16—C156.45 (15)
N1—C8—C9—C10178.90 (10)C11—C12—C16—C15170.97 (11)
C13—C8—C9—C100.10 (17)C14—C15—C16—O2147.37 (11)
N1—C8—C9—C60.40 (12)C14—C15—C16—C1235.06 (14)
C13—C8—C9—C6179.19 (10)C13—C8—N1—C7178.57 (11)
C5—C6—C9—C8179.10 (12)C9—C8—N1—C70.12 (12)
C7—C6—C9—C80.74 (12)C2—C7—N1—C8178.28 (11)
C5—C6—C9—C101.8 (2)C6—C7—N1—C80.60 (12)
C7—C6—C9—C10178.40 (12)C12—C13—O1—C1418.95 (16)
C8—C9—C10—C111.04 (17)C8—C13—O1—C14162.84 (10)
C6—C9—C10—C11178.01 (12)C18—C14—O1—C13165.62 (10)
C9—C10—C11—C120.48 (17)C17—C14—O1—C1375.58 (12)
C10—C11—C12—C131.04 (18)C15—C14—O1—C1346.16 (13)
C10—C11—C12—C16176.35 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.881.992.8634 (13)173
C15—H15A···O1ii0.992.593.5411 (15)161
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H17NO2
Mr279.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.9740 (16), 9.4195 (12), 12.8444 (16)
β (°) 114.733 (2)
V3)1425.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.53 × 0.43 × 0.19
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.886, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
13755, 3526, 2941
Rint0.027
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.109, 1.03
No. of reflections3526
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.26

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
N1—H1···O2i0.881.992.8634 (13)173
C15—H15A···O1ii0.992.593.5411 (15)161
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y1/2, z+1/2.
 

Acknowledgements

The authors acknowledge UGC, New Delhi, India, for the award of a 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 YSU.

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  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 citationKnölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303–4427.  Web of Science PubMed 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. & Zeller, M. (2008). Acta Cryst. E64, o2156.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008). Acta Cryst. E64, o2155.  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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds