6-Meth-oxy-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

The carbazole unit of the title mol-ecule, C(13)H(13)NO(2), is not planar. The dihedral angle between the benzene ring and the pyrrole ring is 1.69 (6)°. The cyclo-hexene ring adopts an envelope conformation. Inter-molecular C-H⋯O and N-H⋯O hydrogen bonds are present in the crystal structure. A C-H⋯π inter-action, involving the benzene ring, is also found in the crystal structure.

Related literature

For related literature, see: Bhattacharya & Chakraborty (1987 ▶); Chakraborty & Roy (1991 ▶); Chakraborty (1993 ▶); Knolker (1986 ▶); Lescot et al. (1986 ▶); Hook et al. (1990 ▶); Hirata et al. (1999 ▶); Kapil (1971 ▶); Knolker & Reddy (2002 ▶); Sowmithran & Rajendra Prasad (1986 ▶); Rajendra Prasad & Vijayalakshmi (1994 ▶). Gunaseelan et al. (2007a ▶,b ▶) and Thiruvalluvar et al. (2007 ▶) have reported the crystal structures of substituted carbazole derivatives, in which the carbazole units are not planar.

Experimental

Crystal data

C13H13NO2

M = 215.24

Monoclinic,

a = 9.0627 (2) Å

b = 14.0285 (3) Å

c = 8.5506 (2) Å

β = 101.815 (1)°

V = 1064.06 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 160 (1) K

0.35 × 0.28 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

28554 measured reflections

3077 independent reflections

2601 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.145

S = 1.12

3077 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007885/wn2245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007885/wn2245Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H13NO2	F000 = 456
Mr = 215.24	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Melting point: 536 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 9.0627 (2) Å	Cell parameters from 3175 reflections
b = 14.0285 (3) Å	θ = 2.0–30.0º
c = 8.5506 (2) Å	µ = 0.09 mm−1
β = 101.815 (1)º	T = 160 (1) K
V = 1064.06 (4) Å3	Tablet, colourless
Z = 4	0.35 × 0.28 × 0.13 mm

Nonius KappaCCD area-detector diffractometer	3077 independent reflections
Radiation source: Nonius FR590 sealed tube generator	2601 reflections with I > 2σ(I)
Monochromator: horizontally mounted graphite crystal	Rint = 0.038
Detector resolution: 9 pixels mm-1	θmax = 30.0º
T = 160(1) K	θmin = 2.3º
φ and ω scans with κ offsets	h = −12→12
Absorption correction: none	k = 0→19
28554 measured reflections	l = 0→12

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0825P)2 + 0.2332P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
3077 reflections	Δρmax = 0.33 e Å−3
149 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.742 (2) Frames collected: 359 Seconds exposure per frame: 100 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

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 > 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.

	x	y	z	Uiso*/Ueq
O1	0.53223 (10)	0.52978 (7)	0.72771 (11)	0.0324 (3)
O2	−0.29638 (10)	0.67151 (8)	0.18475 (11)	0.0354 (3)
N9	0.27900 (11)	0.55709 (7)	0.45710 (11)	0.0229 (3)
C1	0.41200 (13)	0.56555 (8)	0.74513 (13)	0.0229 (3)
C2	0.38660 (13)	0.59515 (9)	0.90781 (13)	0.0251 (3)
C3	0.27324 (13)	0.67715 (8)	0.90149 (13)	0.0236 (3)
C4	0.12214 (12)	0.65469 (8)	0.79020 (12)	0.0213 (3)
C4A	0.14868 (12)	0.61976 (7)	0.63321 (12)	0.0196 (3)
C4B	0.05307 (12)	0.61980 (7)	0.47874 (13)	0.0197 (3)
C5	−0.09638 (12)	0.65107 (8)	0.42156 (13)	0.0219 (3)
C6	−0.15394 (12)	0.64344 (8)	0.25953 (13)	0.0241 (3)
C7	−0.06690 (13)	0.60611 (8)	0.15394 (13)	0.0253 (3)
C8	0.07867 (13)	0.57456 (8)	0.20802 (13)	0.0236 (3)
C8A	0.13856 (12)	0.58090 (7)	0.37241 (13)	0.0208 (3)
C9A	0.28448 (12)	0.58046 (8)	0.61527 (13)	0.0213 (3)
C16	−0.38951 (15)	0.71146 (13)	0.28342 (18)	0.0441 (5)
H2A	0.48420	0.61484	0.97491	0.0301*
H2B	0.34978	0.53939	0.95963	0.0301*
H3A	0.25628	0.68946	1.01044	0.0283*
H3B	0.31607	0.73572	0.86390	0.0283*
H4A	0.06803	0.60539	0.83938	0.0256*
H4B	0.05882	0.71278	0.77373	0.0256*
H5	−0.15509	0.67641	0.49192	0.0262*
H7	−0.10988	0.60272	0.04300	0.0303*
H8	0.13633	0.54942	0.13648	0.0284*
H9	0.3587 (19)	0.5296 (12)	0.416 (2)	0.038 (4)*
H16A	−0.48742	0.72886	0.21742	0.0661*
H16B	−0.34089	0.76845	0.33697	0.0661*
H16C	−0.40428	0.66454	0.36374	0.0661*

	U11	U22	U33	U12	U13	U23
O1	0.0269 (5)	0.0436 (5)	0.0274 (4)	0.0137 (4)	0.0075 (3)	−0.0016 (4)
O2	0.0230 (4)	0.0513 (6)	0.0293 (5)	0.0061 (4)	−0.0008 (3)	−0.0103 (4)
N9	0.0239 (5)	0.0262 (5)	0.0202 (4)	0.0049 (3)	0.0084 (3)	−0.0009 (3)
C1	0.0245 (5)	0.0232 (5)	0.0222 (5)	0.0045 (4)	0.0076 (4)	0.0004 (4)
C2	0.0249 (5)	0.0302 (6)	0.0205 (5)	0.0067 (4)	0.0054 (4)	−0.0010 (4)
C3	0.0235 (5)	0.0252 (5)	0.0227 (5)	0.0028 (4)	0.0064 (4)	−0.0045 (4)
C4	0.0224 (5)	0.0233 (5)	0.0196 (5)	0.0030 (4)	0.0073 (4)	−0.0010 (4)
C4A	0.0215 (5)	0.0188 (5)	0.0199 (5)	0.0012 (3)	0.0073 (4)	0.0012 (3)
C4B	0.0215 (5)	0.0182 (5)	0.0205 (5)	−0.0004 (4)	0.0071 (4)	−0.0004 (3)
C5	0.0212 (5)	0.0223 (5)	0.0232 (5)	−0.0014 (4)	0.0071 (4)	−0.0022 (4)
C6	0.0208 (5)	0.0260 (5)	0.0249 (5)	−0.0018 (4)	0.0036 (4)	−0.0033 (4)
C7	0.0274 (6)	0.0272 (5)	0.0211 (5)	−0.0025 (4)	0.0045 (4)	−0.0034 (4)
C8	0.0276 (5)	0.0245 (5)	0.0204 (5)	−0.0009 (4)	0.0089 (4)	−0.0025 (4)
C8A	0.0231 (5)	0.0200 (5)	0.0210 (5)	0.0001 (4)	0.0085 (4)	−0.0005 (3)
C9A	0.0232 (5)	0.0222 (5)	0.0197 (5)	0.0030 (4)	0.0073 (4)	0.0002 (4)
C16	0.0261 (6)	0.0610 (10)	0.0421 (8)	0.0118 (6)	0.0000 (5)	−0.0185 (7)

O1—C1	1.2360 (15)	C6—C7	1.4154 (16)
O2—C6	1.3756 (15)	C7—C8	1.3785 (17)
O2—C16	1.4247 (18)	C8—C8A	1.4021 (15)
N9—C8A	1.3706 (15)	C2—H2A	0.9900
N9—C9A	1.3826 (14)	C2—H2B	0.9900
N9—H9	0.948 (17)	C3—H3A	0.9900
C1—C9A	1.4446 (16)	C3—H3B	0.9900
C1—C2	1.5138 (16)	C4—H4A	0.9900
C2—C3	1.5359 (17)	C4—H4B	0.9900
C3—C4	1.5318 (16)	C5—H5	0.9500
C4—C4A	1.4940 (14)	C7—H7	0.9500
C4A—C4B	1.4236 (15)	C8—H8	0.9500
C4A—C9A	1.3854 (16)	C16—H16A	0.9800
C4B—C8A	1.4189 (15)	C16—H16B	0.9800
C4B—C5	1.4124 (16)	C16—H16C	0.9800
C5—C6	1.3810 (15)
O1···N9	2.9314 (13)	C16···H3Bviii	2.9800
O1···N9i	2.8313 (14)	H2A···O2x	2.5200
O1···H9	2.804 (17)	H2A···C16x	2.9800
O1···H2Bii	2.8400	H2A···H16Ax	2.5900
O1···H9i	1.918 (17)	H2B···O1ii	2.8400
O2···H2Aiii	2.5200	H2B···C2ii	3.0700
N9···O1	2.9314 (13)	H3A···C8xi	3.0300
N9···O1i	2.8313 (14)	H3A···H8xi	2.5900
C1···C16iv	3.590 (2)	H3B···C9A	3.0200
C2···C2ii	3.5370 (17)	H3B···C8Av	3.0400
C3···C8Av	3.5983 (15)	H3B···C16iv	2.9800
C4B···C4Bvi	3.5353 (14)	H3B···H16Aiv	2.4300
C6···C9Avi	3.5958 (16)	H4A···C7vi	2.9700
C8A···C3vii	3.5983 (15)	H4A···C8vi	2.8400
C9A···C6vi	3.5958 (16)	H4B···C4Bv	2.9400
C16···C1viii	3.590 (2)	H4B···C5v	2.8200
C1···H16Aiv	3.0500	H4B···C6v	2.7800
C1···H9i	3.028 (17)	H4B···C7v	2.8900
C2···H2Bii	3.0700	H4B···C8v	3.0500
C4B···H4Bvii	2.9400	H4B···C8Av	3.0600
C5···H16C	2.7400	H5···C16	2.5300
C5···H4Bvii	2.8200	H5···H16B	2.3100
C5···H16B	2.7400	H5···H16C	2.3100
C6···H4Bvii	2.7800	H8···H3Aix	2.5900
C7···H4Bvii	2.8900	H9···O1	2.804 (17)
C7···H4Avi	2.9700	H9···O1i	1.918 (17)
C8···H4Bvii	3.0500	H9···C1i	3.028 (17)
C8···H4Avi	2.8400	H16A···H2Aiii	2.5900
C8···H3Aix	3.0300	H16A···C1viii	3.0500
C8A···H4Bvii	3.0600	H16A···H3Bviii	2.4300
C8A···H3Bvii	3.0400	H16B···C5	2.7400
C9A···H3B	3.0200	H16B···H5	2.3100
C16···H2Aiii	2.9800	H16C···C5	2.7400
C16···H5	2.5300	H16C···H5	2.3100
C6—O2—C16	116.79 (10)	C1—C2—H2A	109.00
C8A—N9—C9A	107.61 (9)	C1—C2—H2B	109.00
C9A—N9—H9	125.6 (10)	C3—C2—H2A	109.00
C8A—N9—H9	126.8 (10)	C3—C2—H2B	109.00
O1—C1—C9A	123.53 (10)	H2A—C2—H2B	108.00
O1—C1—C2	121.72 (10)	C2—C3—H3A	109.00
C2—C1—C9A	114.73 (10)	C2—C3—H3B	109.00
C1—C2—C3	113.55 (9)	C4—C3—H3A	109.00
C2—C3—C4	111.98 (9)	C4—C3—H3B	109.00
C3—C4—C4A	109.74 (9)	H3A—C3—H3B	108.00
C4B—C4A—C9A	106.45 (9)	C3—C4—H4A	110.00
C4—C4A—C4B	130.85 (10)	C3—C4—H4B	110.00
C4—C4A—C9A	122.69 (10)	C4A—C4—H4A	110.00
C5—C4B—C8A	120.56 (10)	C4A—C4—H4B	110.00
C4A—C4B—C8A	106.61 (9)	H4A—C4—H4B	108.00
C4A—C4B—C5	132.82 (10)	C4B—C5—H5	121.00
C4B—C5—C6	117.50 (10)	C6—C5—H5	121.00
O2—C6—C5	124.74 (10)	C6—C7—H7	119.00
O2—C6—C7	113.70 (10)	C8—C7—H7	119.00
C5—C6—C7	121.55 (10)	C7—C8—H8	121.00
C6—C7—C8	121.66 (10)	C8A—C8—H8	121.00
C7—C8—C8A	117.60 (10)	O2—C16—H16A	109.00
N9—C8A—C8	129.88 (10)	O2—C16—H16B	109.00
C4B—C8A—C8	121.11 (10)	O2—C16—H16C	109.00
N9—C8A—C4B	108.97 (9)	H16A—C16—H16B	109.00
C1—C9A—C4A	124.16 (10)	H16A—C16—H16C	109.00
N9—C9A—C1	125.48 (10)	H16B—C16—H16C	109.00
N9—C9A—C4A	110.36 (10)
C16—O2—C6—C5	0.21 (18)	C4B—C4A—C9A—N9	0.74 (12)
C16—O2—C6—C7	−178.89 (12)	C9A—C4A—C4B—C8A	−0.84 (11)
C9A—N9—C8A—C8	177.52 (11)	C4—C4A—C9A—N9	−178.17 (10)
C8A—N9—C9A—C4A	−0.35 (12)	C4—C4A—C4B—C8A	177.95 (10)
C9A—N9—C8A—C4B	−0.20 (12)	C9A—C4A—C4B—C5	−179.48 (11)
C8A—N9—C9A—C1	179.00 (10)	C5—C4B—C8A—N9	179.49 (10)
C9A—C1—C2—C3	−29.21 (14)	C4A—C4B—C8A—N9	0.65 (12)
O1—C1—C2—C3	152.17 (11)	C5—C4B—C8A—C8	1.54 (16)
C2—C1—C9A—N9	−178.39 (11)	C4A—C4B—C5—C6	177.60 (11)
C2—C1—C9A—C4A	0.87 (16)	C8A—C4B—C5—C6	−0.89 (16)
O1—C1—C9A—C4A	179.47 (11)	C4A—C4B—C8A—C8	−177.31 (10)
O1—C1—C9A—N9	0.21 (19)	C4B—C5—C6—O2	−179.27 (11)
C1—C2—C3—C4	54.63 (13)	C4B—C5—C6—C7	−0.24 (16)
C2—C3—C4—C4A	−49.23 (12)	O2—C6—C7—C8	179.92 (11)
C3—C4—C4A—C4B	−156.37 (11)	C5—C6—C7—C8	0.80 (18)
C3—C4—C4A—C9A	22.25 (14)	C6—C7—C8—C8A	−0.17 (17)
C4—C4A—C4B—C5	−0.7 (2)	C7—C8—C8A—N9	−178.45 (11)
C4B—C4A—C9A—C1	−178.62 (10)	C7—C8—C8A—C4B	−0.97 (16)
C4—C4A—C9A—C1	2.47 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1i	0.948 (17)	1.918 (17)	2.8313 (14)	161.2 (15)
C2—H2A···O2x	0.99	2.52	3.4962 (15)	169
C4—H4B···Cgv	0.99	2.57	3.492 (1)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O1i	0.948 (17)	1.918 (17)	2.8313 (14)	161.2 (15)
C2—H2A⋯O2ii	0.99	2.52	3.4962 (15)	169
C4—H4B⋯Cgiii	0.99	2.57	3.492 (1)	156

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the benzene ring.