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

Archana, R.; Yamuna, E.; Rajendra Prasad, K.J.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536810031545

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2299-o2300

https://doi.org/10.1107/S1600536810031545

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

R. Archana,^a E. Yamuna,^b K. J. Rajendra Prasad,^b A. Thiruvalluvar ^a ^* and R. J. Butcher ^c

^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 ); 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

Crystal data

C₁₃H₁₃NO
M_r = 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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.751, T_max = 1.000
3655 measured reflections
2005 independent reflections
1882 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.33 e Å⁻³
Δρ_min = −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	D⋯A	D—H⋯A
N9—H9⋯O1ⁱ	0.87 (2)	2.01 (2)	2.8603 (15)	165.9 (18)
C2—H2B⋯Cg3ⁱⁱ	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 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031545/jj2046sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031545/jj2046Isup2.hkl

checkCIF report

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.

Structure description 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).

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

	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.
	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

C₁₃H₁₃NO	F(000) = 424
M_r = 199.24	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 443 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 10.5245 (2) Å	Cell parameters from 3169 reflections
b = 7.1564 (1) Å	θ = 5.5–74.0°
c = 13.5870 (3) Å	µ = 0.65 mm⁻¹
β = 93.960 (2)°	T = 110 K
V = 1020.90 (3) Å³	Prism, colourless
Z = 4	0.51 × 0.42 × 0.34 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2005 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 5.5°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→8
T_min = 0.751, T_max = 1.000	l = −16→12
3655 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0737P)² + 0.4222P] where P = (F_o² + 2F_c²)/3
2005 reflections	(Δ/σ)_max = 0.001
141 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₃NO	V = 1020.90 (3) Å³
M_r = 199.24	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.5245 (2) Å	µ = 0.65 mm⁻¹
b = 7.1564 (1) Å	T = 110 K
c = 13.5870 (3) Å	0.51 × 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)
T_min = 0.751, T_max = 1.000	R_int = 0.016
3655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.33 e Å⁻³
2005 reflections	Δρ_min = −0.30 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	−0.14139 (9)	0.43448 (14)	0.05682 (7)	0.0252 (3)
N9	0.11062 (10)	0.26331 (16)	0.07724 (8)	0.0180 (3)
C1	−0.12572 (12)	0.27613 (18)	0.09016 (9)	0.0180 (3)
C2	−0.23534 (12)	0.15732 (18)	0.11989 (9)	0.0188 (3)
C3	−0.19848 (12)	0.01890 (19)	0.20323 (10)	0.0211 (4)
C4	−0.08735 (12)	−0.10760 (18)	0.17805 (9)	0.0202 (3)
C4A	0.01788 (12)	0.00943 (17)	0.14160 (9)	0.0171 (3)
C4B	0.15114 (12)	−0.02537 (18)	0.13993 (9)	0.0177 (3)
C5	0.22998 (13)	−0.17717 (18)	0.16994 (9)	0.0207 (4)
C6	0.35880 (13)	−0.16125 (19)	0.15961 (10)	0.0229 (4)
C7	0.41100 (12)	0.00095 (19)	0.11902 (10)	0.0215 (4)
C8	0.33738 (12)	0.15274 (18)	0.08785 (9)	0.0194 (4)
C8A	0.20563 (12)	0.13615 (17)	0.09939 (9)	0.0174 (3)
C9A	−0.00264 (12)	0.18558 (18)	0.10250 (9)	0.0171 (3)
C18	0.39245 (13)	0.3254 (2)	0.04456 (11)	0.0274 (4)
H2A	−0.30348	0.24034	0.14124	0.0226*
H2B	−0.27040	0.08665	0.06153	0.0226*
H3A	−0.17410	0.08918	0.26440	0.0254*
H3B	−0.27315	−0.05960	0.21569	0.0254*
H4A	−0.11694	−0.19866	0.12660	0.0242*
H4B	−0.05557	−0.17803	0.23745	0.0242*
H5	0.19525	−0.28723	0.19651	0.0248*
H6	0.41364	−0.26137	0.18020	0.0275*
H7	0.50030	0.00602	0.11288	0.0258*
H9	0.1191 (16)	0.367 (3)	0.0455 (13)	0.028 (4)*
H18A	0.48445	0.30932	0.04072	0.0411*
H18B	0.35236	0.34649	−0.02177	0.0411*
H18C	0.37648	0.43317	0.08648	0.0411*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0232 (5)	0.0218 (5)	0.0312 (5)	0.0037 (4)	0.0057 (4)	0.0081 (4)
N9	0.0179 (5)	0.0162 (5)	0.0203 (5)	0.0005 (4)	0.0034 (4)	0.0027 (4)
C1	0.0204 (6)	0.0198 (6)	0.0140 (6)	0.0004 (5)	0.0021 (4)	−0.0001 (5)
C2	0.0171 (6)	0.0201 (6)	0.0195 (6)	0.0003 (5)	0.0026 (5)	−0.0010 (5)
C3	0.0209 (6)	0.0217 (7)	0.0214 (6)	−0.0013 (5)	0.0059 (5)	0.0027 (5)
C4	0.0218 (6)	0.0181 (6)	0.0210 (6)	−0.0010 (5)	0.0042 (5)	0.0034 (5)
C4A	0.0201 (6)	0.0178 (6)	0.0136 (6)	−0.0005 (5)	0.0019 (4)	−0.0002 (4)
C4B	0.0211 (6)	0.0186 (6)	0.0133 (6)	0.0003 (5)	0.0016 (4)	−0.0008 (4)
C5	0.0252 (7)	0.0189 (6)	0.0179 (6)	0.0016 (5)	0.0013 (5)	0.0030 (5)
C6	0.0239 (7)	0.0224 (7)	0.0220 (6)	0.0060 (5)	−0.0017 (5)	0.0018 (5)
C7	0.0173 (6)	0.0260 (7)	0.0209 (6)	0.0022 (5)	−0.0003 (5)	−0.0019 (5)
C8	0.0193 (6)	0.0209 (7)	0.0181 (6)	−0.0005 (5)	0.0016 (5)	−0.0017 (5)
C8A	0.0196 (6)	0.0181 (6)	0.0145 (6)	0.0014 (5)	0.0006 (4)	−0.0008 (4)
C9A	0.0179 (6)	0.0183 (6)	0.0154 (6)	−0.0010 (5)	0.0031 (4)	0.0001 (4)
C18	0.0191 (7)	0.0248 (7)	0.0385 (8)	−0.0009 (5)	0.0045 (5)	0.0046 (6)

Geometric parameters (Å, º) top

O1—C1	1.2273 (16)	C7—C8	1.3836 (18)
N9—C8A	1.3700 (17)	C8—C8A	1.4112 (18)
N9—C9A	1.3801 (17)	C8—C18	1.5019 (19)
N9—H9	0.87 (2)	C2—H2A	0.9900
C1—C9A	1.4478 (18)	C2—H2B	0.9900
C1—C2	1.5105 (18)	C3—H3A	0.9900
C2—C3	1.5340 (18)	C3—H3B	0.9900
C3—C4	1.5362 (18)	C4—H4A	0.9900
C4—C4A	1.4997 (18)	C4—H4B	0.9900
C4A—C4B	1.4262 (18)	C5—H5	0.9500
C4A—C9A	1.3792 (18)	C6—H6	0.9500
C4B—C8A	1.4185 (18)	C7—H7	0.9500
C4B—C5	1.4100 (18)	C18—H18A	0.9800
C5—C6	1.3773 (19)	C18—H18B	0.9800
C6—C7	1.4125 (19)	C18—H18C	0.9800

O1···N9	2.9173 (14)	H2A···H18A^vii	2.5800
O1···C18ⁱ	3.3659 (17)	H2A···C3^vi	2.9000
O1···N9ⁱ	2.8603 (15)	H2A···C4^vi	2.9900
O1···H9	2.798 (17)	H2A···H3B^vi	2.5000
O1···H4Aⁱⁱ	2.8000	H2A···H4B^vi	2.3700
O1···H9ⁱ	2.01 (2)	H2B···C7ⁱⁱⁱ	2.8500
O1···H18Bⁱ	2.7300	H2B···C8ⁱⁱⁱ	2.7100
N9···O1	2.9173 (14)	H2B···C8Aⁱⁱⁱ	2.8300
N9···O1ⁱ	2.8603 (15)	H3A···C9A	3.0200
N9···H4Aⁱⁱⁱ	2.8100	H3A···H3B^vi	2.5900
C1···C4Bⁱⁱⁱ	3.5986 (18)	H3B···C2^viii	3.0100
C4A···C9Aⁱⁱⁱ	3.5916 (17)	H3B···H2A^viii	2.5000
C4B···C1ⁱⁱⁱ	3.5986 (18)	H3B···H3A^viii	2.5900
C5···C8A^iv	3.4312 (17)	H4A···O1^ix	2.8000
C8A···C5^v	3.4312 (17)	H4A···N9ⁱⁱⁱ	2.8100
C9A···C4Aⁱⁱⁱ	3.5916 (17)	H4B···H2A^viii	2.3700
C18···O1ⁱ	3.3659 (17)	H5···C8^iv	3.0000
C2···H3B^vi	3.0100	H5···C8A^iv	2.9500
C2···H7^vii	2.9800	H6···H18C^ix	2.5500
C3···H2A^viii	2.9000	H6···C4A^iv	2.9700
C4···H2A^viii	2.9900	H6···C9A^iv	3.0600
C4A···H6^v	2.9700	H7···C2^x	2.9800
C6···H18C^ix	3.0800	H7···H18A	2.3800
C7···H2Bⁱⁱⁱ	2.8500	H9···O1	2.798 (17)
C8···H2Bⁱⁱⁱ	2.7100	H9···C18	2.893 (17)
C8···H5^v	3.0000	H9···O1ⁱ	2.01 (2)
C8A···H5^v	2.9500	H18A···H2A^x	2.5800
C8A···H2Bⁱⁱⁱ	2.8300	H18A···H7	2.3800
C9A···H3A	3.0200	H18B···O1ⁱ	2.7300
C9A···H6^v	3.0600	H18C···C6ⁱⁱ	3.0800
C18···H9	2.893 (17)	H18C···H6ⁱⁱ	2.5500

C8A—N9—C9A	107.91 (11)	C1—C2—H2A	109.00
C9A—N9—H9	126.1 (11)	C1—C2—H2B	109.00
C8A—N9—H9	125.4 (11)	C3—C2—H2A	109.00
O1—C1—C9A	123.53 (12)	C3—C2—H2B	109.00
O1—C1—C2	122.20 (11)	H2A—C2—H2B	108.00
C2—C1—C9A	114.26 (11)	C2—C3—H3A	109.00
C1—C2—C3	113.70 (10)	C2—C3—H3B	109.00
C2—C3—C4	111.95 (11)	C4—C3—H3A	109.00
C3—C4—C4A	109.60 (10)	C4—C3—H3B	109.00
C4B—C4A—C9A	106.35 (11)	H3A—C3—H3B	108.00
C4—C4A—C4B	131.09 (11)	C3—C4—H4A	110.00
C4—C4A—C9A	122.55 (11)	C3—C4—H4B	110.00
C5—C4B—C8A	119.64 (12)	C4A—C4—H4A	110.00
C4A—C4B—C8A	106.76 (11)	C4A—C4—H4B	110.00
C4A—C4B—C5	133.60 (12)	H4A—C4—H4B	108.00
C4B—C5—C6	118.07 (12)	C4B—C5—H5	121.00
C5—C6—C7	121.33 (12)	C6—C5—H5	121.00
C6—C7—C8	122.68 (12)	C5—C6—H6	119.00
C7—C8—C18	122.87 (12)	C7—C6—H6	119.00
C7—C8—C8A	115.70 (11)	C6—C7—H7	119.00
C8A—C8—C18	121.43 (11)	C8—C7—H7	119.00
N9—C8A—C8	128.87 (11)	C8—C18—H18A	109.00
C4B—C8A—C8	122.58 (11)	C8—C18—H18B	109.00
N9—C8A—C4B	108.55 (11)	C8—C18—H18C	109.00
C1—C9A—C4A	124.67 (12)	H18A—C18—H18B	109.00
N9—C9A—C1	124.89 (11)	H18A—C18—H18C	109.00
N9—C9A—C4A	110.44 (11)	H18B—C18—H18C	109.00

C9A—N9—C8A—C4B	−0.22 (14)	C4—C4A—C9A—N9	178.50 (11)
C9A—N9—C8A—C8	−179.22 (12)	C4—C4A—C9A—C1	−1.27 (19)
C8A—N9—C9A—C1	−179.79 (12)	C4B—C4A—C9A—N9	−0.48 (14)
C8A—N9—C9A—C4A	0.45 (14)	C4B—C4A—C9A—C1	179.75 (12)
O1—C1—C2—C3	−150.62 (12)	C4A—C4B—C5—C6	−178.27 (13)
C9A—C1—C2—C3	30.63 (15)	C8A—C4B—C5—C6	0.78 (18)
O1—C1—C9A—N9	−1.1 (2)	C4A—C4B—C8A—N9	−0.07 (14)
O1—C1—C9A—C4A	178.62 (12)	C4A—C4B—C8A—C8	179.00 (11)
C2—C1—C9A—N9	177.62 (11)	C5—C4B—C8A—N9	−179.35 (11)
C2—C1—C9A—C4A	−2.64 (18)	C5—C4B—C8A—C8	−0.28 (19)
C1—C2—C3—C4	−55.14 (14)	C4B—C5—C6—C7	−0.81 (19)
C2—C3—C4—C4A	48.86 (14)	C5—C6—C7—C8	0.3 (2)
C3—C4—C4A—C4B	156.41 (13)	C6—C7—C8—C8A	0.20 (19)
C3—C4—C4A—C9A	−22.29 (16)	C6—C7—C8—C18	−179.93 (14)
C4—C4A—C4B—C5	0.6 (2)	C7—C8—C8A—N9	178.66 (12)
C4—C4A—C4B—C8A	−178.52 (12)	C7—C8—C8A—C4B	−0.21 (18)
C9A—C4A—C4B—C5	179.47 (14)	C18—C8—C8A—N9	−1.2 (2)
C9A—C4A—C4B—C8A	0.33 (14)	C18—C8—C8A—C4B	179.92 (12)

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x, −y, −z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x−1/2, y+1/2, −z+1/2; (vii) x−1, y, z; (viii) −x−1/2, y−1/2, −z+1/2; (ix) x, y−1, 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···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱ	0.87 (2)	2.01 (2)	2.8603 (15)	165.9 (18)
C2—H2B···Cg3ⁱⁱⁱ	0.99	2.64	3.5429 (13)	152
C5—H5···Cg3^iv	0.95	2.86	3.6414 (14)	140

Symmetry codes: (i) −x, −y+1, −z; (iii) −x, −y, −z; (iv) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO
M_r	199.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	110
a, b, c (Å)	10.5245 (2), 7.1564 (1), 13.5870 (3)
β (°)	93.960 (2)
V (Å³)	1020.90 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.51 × 0.42 × 0.34

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.751, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3655, 2005, 1882
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.120, 1.05
No. of reflections	2005
No. of parameters	141
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱ	0.87 (2)	2.01 (2)	2.8603 (15)	165.9 (18)
C2—H2B···Cg3ⁱⁱ	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+1/2, y−1/2, −z+1/2.

Acknowledgements

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

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