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ISSN: 2056-9890

8-Methyl-2,3,4,9-tetra­hydro-1H-carbazol-1-one

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: athiru@vsnl.net

(Received 19 July 2010; accepted 5 August 2010; online 11 August 2010)

In the title compound, C13H13NO, the dihedral angle between the benzene ring and the fused pyrrole ring is 0.96 (7)°. The cyclohexenone ring adopts an envelope conformation. Inter­molecular N—H⋯O hydrogen bonds form R22(10) ring motifs in the crystal structure. Weak C—H⋯π inter­actions involving the benzene ring also occur.

Related literature

For tetra­hydro­carbazolones, see: Bringmann et al. (1995[Bringmann, G., Ledermann, A. & François, G. (1995). Heterocycles, 40, 293-300.]); Chakravarty et al. (2001[Chakravarty, A. K., Sarkar, T., Masuda, K., Takey, T., Doi, H., Kotani, E. & Shiojima, K. (2001). Indian J. Chem. Sect. B, 40, 484-489.]); Knölker & Reddy (2002[Knölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303-4428.]); Lin & Zhang (2000[Lin, G. & Zhang, A. (2000). Tetrahedron, 56, 7163-7171.]); Matsuo & Ishida (1994[Matsuo, K. & Ishida, S. (1994). Chem. Pharm. Bull. 42, 1325-1327.]); Miki & Hachiken (1993[Miki, Y. & Hachiken, H. (1993). Synlett, pp. 333-334.]); Scott et al. (2006[Scott, T. L., Yu, X., Gorugantula, S. P., Carrero-Martinez, G. & Söderberg, B. C. G. (2006). Tetrahedron, 62, 10835-10842.]). For biologically active carbazoles, see: Jean et al. (2004[Jean, C. F., Rangisetty, J. B., Dukat, M., Setola, V., Raffay, T., Roth, B. & Glennon, R. A. (2004). Bioorg. Med. Chem. Lett. 14, 1961-1964.]); Knölker & Reddy (2008[Knölker, H. J. & Reddy, K. R. (2008). The Alkaloids: Chemistry and Biology, edited by G. A. Cordell, Vol. 65, pp. 181-193. London: Academic Press.]). For the preparation of 1-oxo compounds via their corresponding hydrazones, see: Rajendra Prasad & Vijayalakshmi (1994[Rajendra Prasad, K. J. & Vijayalakshmi, C. S. (1994). Indian J. Chem. Sect. B, 33, 481-482.]). For crystal structures of substituted carbazole derivatives, see: Thomas Gunaseelan et al. (2009[Thomas Gunaseelan, A., Prabakaran, K., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o1946-o1947.]); Sridharan et al. (2008[Sridharan, M., Prasad, K. J. R., Gunaseelan, A. T., Thiruvalluvar, A. & Linden, A. (2008). Acta Cryst. E64, o763-o764.]); Thiruvalluvar et al. (2007[Thiruvalluvar, A., Gunaseelan, A. T., Martin, A. E., Prasad, K. J. R. & Butcher, R. J. (2007). Acta Cryst. E63, o3524.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO

  • Mr = 199.24

  • Monoclinic, P 21 /n

  • a = 10.5245 (2) Å

  • b = 7.1564 (1) Å

  • c = 13.5870 (3) Å

  • β = 93.960 (2)°

  • V = 1020.90 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.65 mm−1

  • T = 110 K

  • 0.51 × 0.42 × 0.34 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.751, Tmax = 1.000

  • 3655 measured reflections

  • 2005 independent reflections

  • 1882 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.120

  • S = 1.05

  • 2005 reflections

  • 141 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4B,C5–C8,C8A ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N9—H9⋯O1i 0.87 (2) 2.01 (2) 2.8603 (15) 165.9 (18)
C2—H2BCg3ii 0.99 2.64 3.5429 (13) 152
C5—H5⋯Cg3iii 0.95 2.86 3.6414 (14) 140
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Tetrahydrocarbazolones have been used extensively as advanced intermediates in synthetic efforts toward a number of naturally occurring carbazole alkaloids (Bringmann et al., (1995); Chakravarty et al., (2001); Knölker & Reddy (2002); Lin & Zhang (2000); Matsuo & Ishida (1994); Miki & Hachiken (1993); Scott et al., (2006)). Jean et al. (2004) and Knölker & Reddy (2008) have reported biologically active carbazoles. The preparation of 1-oxo compounds via their corresponding hydrazones have been reported (Rajendra Prasad & Vijayalakshmi (1994)).

Thomas Gunaseelan et al. (2009), Sridharan et al. (2008) and Thiruvalluvar et al. (2007) have reported the crystal structures of substituted carbazole derivatives, in which the carbazole units are not planar. In the title molecule (Scheme I, Fig. 1), C13H13NO, the carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 0.96 (7)°. The r.m.s. deviation of a mean plane fitted through all non hydrogen atoms excluding C3 of the carbazole unit is 0.0180 Å; C3 deviates from this plane by 0.620 (2) Å. The cyclohexene ring adopts an envelope conformation. The puckering parameters (Cremer & Pople, 1975) are q2=0.3623 (14) Å, q3=-0.2730 (14) Å, Q=0.4536 (14) Å, θ=127.00 (18)° and φ=292.7 (2)°. Intermolecular N9—H9···O1 hydrogen bonds form a R22(10)(Bernstein et al., 1995) ring motif in the crystal structure (Table 1, Fig. 2). Weak C2—H2B···π and C5—H5···π interactions involving the benzene (C4B,C5—C8,C8A) ring are also found in the structure(Table 1).

Related literature top

For tetrahydrocarbazolones, see: Bringmann et al. (1995); Chakravarty et al. (2001); Knölker & Reddy (2002); Lin & Zhang (2000); Matsuo & Ishida (1994); Miki & Hachiken (1993); Scott et al. (2006). For biologically active carbazoles, see: Jean et al. (2004); Knölker & Reddy (2008). For the preparation of 1-oxo compounds via their corresponding hydrazones, see: Rajendra Prasad & Vijayalakshmi (1994). For crystal structures of substituted carbazole derivatives, see: Thomas Gunaseelan et al. (2009); Sridharan et al. (2008); Thiruvalluvar et al. (2007). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of 2-(2-o-tolylhydrazono)-cyclohexanone (0.216 g, 0.001 mol) in a mixture of acetic acid (20 ml) and hydrochloric acid (5 ml) was refluxed on an oil bath pre-heated to 398 K for 2 h. The contents were then cooled and poured onto cold water with stirring. The brown solid which was separated by passing through a column of silica gel and eluted with (98:2, v/v) petroleum ether: ethyl acetate mixture to yield the title compound (0.126 g, 63%). This was recrystallized from ethanol.

Refinement top

The H atom bonded to N9 was located in a difference Fourier map and refined freely. Other H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.99 Å and Uiso(H) = 1.2–1.5Ueq(parent atom).

Structure description top

Tetrahydrocarbazolones have been used extensively as advanced intermediates in synthetic efforts toward a number of naturally occurring carbazole alkaloids (Bringmann et al., (1995); Chakravarty et al., (2001); Knölker & Reddy (2002); Lin & Zhang (2000); Matsuo & Ishida (1994); Miki & Hachiken (1993); Scott et al., (2006)). Jean et al. (2004) and Knölker & Reddy (2008) have reported biologically active carbazoles. The preparation of 1-oxo compounds via their corresponding hydrazones have been reported (Rajendra Prasad & Vijayalakshmi (1994)).

Thomas Gunaseelan et al. (2009), Sridharan et al. (2008) and Thiruvalluvar et al. (2007) have reported the crystal structures of substituted carbazole derivatives, in which the carbazole units are not planar. In the title molecule (Scheme I, Fig. 1), C13H13NO, the carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 0.96 (7)°. The r.m.s. deviation of a mean plane fitted through all non hydrogen atoms excluding C3 of the carbazole unit is 0.0180 Å; C3 deviates from this plane by 0.620 (2) Å. The cyclohexene ring adopts an envelope conformation. The puckering parameters (Cremer & Pople, 1975) are q2=0.3623 (14) Å, q3=-0.2730 (14) Å, Q=0.4536 (14) Å, θ=127.00 (18)° and φ=292.7 (2)°. Intermolecular N9—H9···O1 hydrogen bonds form a R22(10)(Bernstein et al., 1995) ring motif in the crystal structure (Table 1, Fig. 2). Weak C2—H2B···π and C5—H5···π interactions involving the benzene (C4B,C5—C8,C8A) ring are also found in the structure(Table 1).

For tetrahydrocarbazolones, see: Bringmann et al. (1995); Chakravarty et al. (2001); Knölker & Reddy (2002); Lin & Zhang (2000); Matsuo & Ishida (1994); Miki & Hachiken (1993); Scott et al. (2006). For biologically active carbazoles, see: Jean et al. (2004); Knölker & Reddy (2008). For the preparation of 1-oxo compounds via their corresponding hydrazones, see: Rajendra Prasad & Vijayalakshmi (1994). For crystal structures of substituted carbazole derivatives, see: Thomas Gunaseelan et al. (2009); Sridharan et al. (2008); Thiruvalluvar et al. (2007). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal structure of (I), viewed down the b axis, showing the formation of a R22(10) ring motif.
8-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one top
Crystal data top
C13H13NOF(000) = 424
Mr = 199.24Dx = 1.296 Mg m3
Monoclinic, P21/nMelting point: 443 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54184 Å
a = 10.5245 (2) ÅCell parameters from 3169 reflections
b = 7.1564 (1) Åθ = 5.5–74.0°
c = 13.5870 (3) ŵ = 0.65 mm1
β = 93.960 (2)°T = 110 K
V = 1020.90 (3) Å3Prism, colourless
Z = 40.51 × 0.42 × 0.34 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
2005 independent reflections
Radiation source: Enhance (Cu) X-ray Source1882 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 10.5081 pixels mm-1θmax = 74.1°, θmin = 5.5°
ω scansh = 1312
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 88
Tmin = 0.751, Tmax = 1.000l = 1612
3655 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0737P)2 + 0.4222P]
where P = (Fo2 + 2Fc2)/3
2005 reflections(Δ/σ)max = 0.001
141 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C13H13NOV = 1020.90 (3) Å3
Mr = 199.24Z = 4
Monoclinic, P21/nCu Kα radiation
a = 10.5245 (2) ŵ = 0.65 mm1
b = 7.1564 (1) ÅT = 110 K
c = 13.5870 (3) Å0.51 × 0.42 × 0.34 mm
β = 93.960 (2)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
2005 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
1882 reflections with I > 2σ(I)
Tmin = 0.751, Tmax = 1.000Rint = 0.016
3655 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.33 e Å3
2005 reflectionsΔρmin = 0.30 e Å3
141 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
O10.14139 (9)0.43448 (14)0.05682 (7)0.0252 (3)
N90.11062 (10)0.26331 (16)0.07724 (8)0.0180 (3)
C10.12572 (12)0.27613 (18)0.09016 (9)0.0180 (3)
C20.23534 (12)0.15732 (18)0.11989 (9)0.0188 (3)
C30.19848 (12)0.01890 (19)0.20323 (10)0.0211 (4)
C40.08735 (12)0.10760 (18)0.17805 (9)0.0202 (3)
C4A0.01788 (12)0.00943 (17)0.14160 (9)0.0171 (3)
C4B0.15114 (12)0.02537 (18)0.13993 (9)0.0177 (3)
C50.22998 (13)0.17717 (18)0.16994 (9)0.0207 (4)
C60.35880 (13)0.16125 (19)0.15961 (10)0.0229 (4)
C70.41100 (12)0.00095 (19)0.11902 (10)0.0215 (4)
C80.33738 (12)0.15274 (18)0.08785 (9)0.0194 (4)
C8A0.20563 (12)0.13615 (17)0.09939 (9)0.0174 (3)
C9A0.00264 (12)0.18558 (18)0.10250 (9)0.0171 (3)
C180.39245 (13)0.3254 (2)0.04456 (11)0.0274 (4)
H2A0.303480.240340.141240.0226*
H2B0.270400.086650.061530.0226*
H3A0.174100.089180.264400.0254*
H3B0.273150.059600.215690.0254*
H4A0.116940.198660.126600.0242*
H4B0.055570.178030.237450.0242*
H50.195250.287230.196510.0248*
H60.413640.261370.180200.0275*
H70.500300.006020.112880.0258*
H90.1191 (16)0.367 (3)0.0455 (13)0.028 (4)*
H18A0.484450.309320.040720.0411*
H18B0.352360.346490.021770.0411*
H18C0.376480.433170.086480.0411*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0232 (5)0.0218 (5)0.0312 (5)0.0037 (4)0.0057 (4)0.0081 (4)
N90.0179 (5)0.0162 (5)0.0203 (5)0.0005 (4)0.0034 (4)0.0027 (4)
C10.0204 (6)0.0198 (6)0.0140 (6)0.0004 (5)0.0021 (4)0.0001 (5)
C20.0171 (6)0.0201 (6)0.0195 (6)0.0003 (5)0.0026 (5)0.0010 (5)
C30.0209 (6)0.0217 (7)0.0214 (6)0.0013 (5)0.0059 (5)0.0027 (5)
C40.0218 (6)0.0181 (6)0.0210 (6)0.0010 (5)0.0042 (5)0.0034 (5)
C4A0.0201 (6)0.0178 (6)0.0136 (6)0.0005 (5)0.0019 (4)0.0002 (4)
C4B0.0211 (6)0.0186 (6)0.0133 (6)0.0003 (5)0.0016 (4)0.0008 (4)
C50.0252 (7)0.0189 (6)0.0179 (6)0.0016 (5)0.0013 (5)0.0030 (5)
C60.0239 (7)0.0224 (7)0.0220 (6)0.0060 (5)0.0017 (5)0.0018 (5)
C70.0173 (6)0.0260 (7)0.0209 (6)0.0022 (5)0.0003 (5)0.0019 (5)
C80.0193 (6)0.0209 (7)0.0181 (6)0.0005 (5)0.0016 (5)0.0017 (5)
C8A0.0196 (6)0.0181 (6)0.0145 (6)0.0014 (5)0.0006 (4)0.0008 (4)
C9A0.0179 (6)0.0183 (6)0.0154 (6)0.0010 (5)0.0031 (4)0.0001 (4)
C180.0191 (7)0.0248 (7)0.0385 (8)0.0009 (5)0.0045 (5)0.0046 (6)
Geometric parameters (Å, º) top
O1—C11.2273 (16)C7—C81.3836 (18)
N9—C8A1.3700 (17)C8—C8A1.4112 (18)
N9—C9A1.3801 (17)C8—C181.5019 (19)
N9—H90.87 (2)C2—H2A0.9900
C1—C9A1.4478 (18)C2—H2B0.9900
C1—C21.5105 (18)C3—H3A0.9900
C2—C31.5340 (18)C3—H3B0.9900
C3—C41.5362 (18)C4—H4A0.9900
C4—C4A1.4997 (18)C4—H4B0.9900
C4A—C4B1.4262 (18)C5—H50.9500
C4A—C9A1.3792 (18)C6—H60.9500
C4B—C8A1.4185 (18)C7—H70.9500
C4B—C51.4100 (18)C18—H18A0.9800
C5—C61.3773 (19)C18—H18B0.9800
C6—C71.4125 (19)C18—H18C0.9800
O1···N92.9173 (14)H2A···H18Avii2.5800
O1···C18i3.3659 (17)H2A···C3vi2.9000
O1···N9i2.8603 (15)H2A···C4vi2.9900
O1···H92.798 (17)H2A···H3Bvi2.5000
O1···H4Aii2.8000H2A···H4Bvi2.3700
O1···H9i2.01 (2)H2B···C7iii2.8500
O1···H18Bi2.7300H2B···C8iii2.7100
N9···O12.9173 (14)H2B···C8Aiii2.8300
N9···O1i2.8603 (15)H3A···C9A3.0200
N9···H4Aiii2.8100H3A···H3Bvi2.5900
C1···C4Biii3.5986 (18)H3B···C2viii3.0100
C4A···C9Aiii3.5916 (17)H3B···H2Aviii2.5000
C4B···C1iii3.5986 (18)H3B···H3Aviii2.5900
C5···C8Aiv3.4312 (17)H4A···O1ix2.8000
C8A···C5v3.4312 (17)H4A···N9iii2.8100
C9A···C4Aiii3.5916 (17)H4B···H2Aviii2.3700
C18···O1i3.3659 (17)H5···C8iv3.0000
C2···H3Bvi3.0100H5···C8Aiv2.9500
C2···H7vii2.9800H6···H18Cix2.5500
C3···H2Aviii2.9000H6···C4Aiv2.9700
C4···H2Aviii2.9900H6···C9Aiv3.0600
C4A···H6v2.9700H7···C2x2.9800
C6···H18Cix3.0800H7···H18A2.3800
C7···H2Biii2.8500H9···O12.798 (17)
C8···H2Biii2.7100H9···C182.893 (17)
C8···H5v3.0000H9···O1i2.01 (2)
C8A···H5v2.9500H18A···H2Ax2.5800
C8A···H2Biii2.8300H18A···H72.3800
C9A···H3A3.0200H18B···O1i2.7300
C9A···H6v3.0600H18C···C6ii3.0800
C18···H92.893 (17)H18C···H6ii2.5500
C8A—N9—C9A107.91 (11)C1—C2—H2A109.00
C9A—N9—H9126.1 (11)C1—C2—H2B109.00
C8A—N9—H9125.4 (11)C3—C2—H2A109.00
O1—C1—C9A123.53 (12)C3—C2—H2B109.00
O1—C1—C2122.20 (11)H2A—C2—H2B108.00
C2—C1—C9A114.26 (11)C2—C3—H3A109.00
C1—C2—C3113.70 (10)C2—C3—H3B109.00
C2—C3—C4111.95 (11)C4—C3—H3A109.00
C3—C4—C4A109.60 (10)C4—C3—H3B109.00
C4B—C4A—C9A106.35 (11)H3A—C3—H3B108.00
C4—C4A—C4B131.09 (11)C3—C4—H4A110.00
C4—C4A—C9A122.55 (11)C3—C4—H4B110.00
C5—C4B—C8A119.64 (12)C4A—C4—H4A110.00
C4A—C4B—C8A106.76 (11)C4A—C4—H4B110.00
C4A—C4B—C5133.60 (12)H4A—C4—H4B108.00
C4B—C5—C6118.07 (12)C4B—C5—H5121.00
C5—C6—C7121.33 (12)C6—C5—H5121.00
C6—C7—C8122.68 (12)C5—C6—H6119.00
C7—C8—C18122.87 (12)C7—C6—H6119.00
C7—C8—C8A115.70 (11)C6—C7—H7119.00
C8A—C8—C18121.43 (11)C8—C7—H7119.00
N9—C8A—C8128.87 (11)C8—C18—H18A109.00
C4B—C8A—C8122.58 (11)C8—C18—H18B109.00
N9—C8A—C4B108.55 (11)C8—C18—H18C109.00
C1—C9A—C4A124.67 (12)H18A—C18—H18B109.00
N9—C9A—C1124.89 (11)H18A—C18—H18C109.00
N9—C9A—C4A110.44 (11)H18B—C18—H18C109.00
C9A—N9—C8A—C4B0.22 (14)C4—C4A—C9A—N9178.50 (11)
C9A—N9—C8A—C8179.22 (12)C4—C4A—C9A—C11.27 (19)
C8A—N9—C9A—C1179.79 (12)C4B—C4A—C9A—N90.48 (14)
C8A—N9—C9A—C4A0.45 (14)C4B—C4A—C9A—C1179.75 (12)
O1—C1—C2—C3150.62 (12)C4A—C4B—C5—C6178.27 (13)
C9A—C1—C2—C330.63 (15)C8A—C4B—C5—C60.78 (18)
O1—C1—C9A—N91.1 (2)C4A—C4B—C8A—N90.07 (14)
O1—C1—C9A—C4A178.62 (12)C4A—C4B—C8A—C8179.00 (11)
C2—C1—C9A—N9177.62 (11)C5—C4B—C8A—N9179.35 (11)
C2—C1—C9A—C4A2.64 (18)C5—C4B—C8A—C80.28 (19)
C1—C2—C3—C455.14 (14)C4B—C5—C6—C70.81 (19)
C2—C3—C4—C4A48.86 (14)C5—C6—C7—C80.3 (2)
C3—C4—C4A—C4B156.41 (13)C6—C7—C8—C8A0.20 (19)
C3—C4—C4A—C9A22.29 (16)C6—C7—C8—C18179.93 (14)
C4—C4A—C4B—C50.6 (2)C7—C8—C8A—N9178.66 (12)
C4—C4A—C4B—C8A178.52 (12)C7—C8—C8A—C4B0.21 (18)
C9A—C4A—C4B—C5179.47 (14)C18—C8—C8A—N91.2 (2)
C9A—C4A—C4B—C8A0.33 (14)C18—C8—C8A—C4B179.92 (12)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z; (iii) x, y, z; (iv) x+1/2, y1/2, z+1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x1/2, y+1/2, z+1/2; (vii) x1, y, z; (viii) x1/2, y1/2, z+1/2; (ix) x, y1, z; (x) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C4B,C5–C8,C8A ring.
D—H···AD—HH···AD···AD—H···A
N9—H9···O1i0.87 (2)2.01 (2)2.8603 (15)165.9 (18)
C2—H2B···Cg3iii0.992.643.5429 (13)152
C5—H5···Cg3iv0.952.863.6414 (14)140
Symmetry codes: (i) x, y+1, z; (iii) x, y, z; (iv) x+1/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H13NO
Mr199.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)110
a, b, c (Å)10.5245 (2), 7.1564 (1), 13.5870 (3)
β (°) 93.960 (2)
V3)1020.90 (3)
Z4
Radiation typeCu Kα
µ (mm1)0.65
Crystal size (mm)0.51 × 0.42 × 0.34
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.751, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
3655, 2005, 1882
Rint0.016
(sin θ/λ)max1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.120, 1.05
No. of reflections2005
No. of parameters141
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), CrysAlis PRO, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C4B,C5–C8,C8A ring.
D—H···AD—HH···AD···AD—H···A
N9—H9···O1i0.87 (2)2.01 (2)2.8603 (15)165.9 (18)
C2—H2B···Cg3ii0.992.643.5429 (13)152
C5—H5···Cg3iii0.952.863.6414 (14)140
Symmetry codes: (i) x, y+1, z; (ii) x, y, z; (iii) x+1/2, y1/2, z+1/2.
 

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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