2,2-Dimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4(11H)-one.

The title compound, C(17)H(15)NO(2), was prepared from 1-hydroxy-carbazole and 3,3-dimethyl-acrylic acid with a mixture of AlCl(3) and POCl(3) as the cyclization catalyst. Owing to the presence of the -CMe(2)- group, the mol-ecule is not quite planar. In the crystal structre, strong N-H⋯O hydrogen bonds and weaker C-H⋯π inter-actions occur, and a slipped π-π stacking inter-action [centroid-centroid separation = 3.8425 (8) Å] is also observed.

Related literature

Knölker & Reddy (2002 ▶) report on the isolation of pyran­ocarbazoles from various plant species, and Shanaza­rov et al. (1989 ▶) on their potential beneficial properties. Kavitha & Prasad (2003 ▶) 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 & Zeller (2008 ▶) report the structure of the 10-methyl derivative of the title compound.

Experimental

Crystal data

C17H15NO2

M = 265.30

Monoclinic,

a = 5.9926 (5) Å

b = 14.3368 (12) Å

c = 15.6839 (13) Å

β = 95.270 (1)°

V = 1341.78 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.37 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.887, T max = 0.986

12548 measured reflections

3083 independent reflections

2630 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.094

S = 1.06

3083 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033849/hb2803sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033849/hb2803Isup2.hkl

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

C17H15NO2	F(000) = 560
Mr = 265.30	Dx = 1.313 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4649 reflections
a = 5.9926 (5) Å	θ = 2.6–27.5°
b = 14.3368 (12) Å	µ = 0.09 mm−1
c = 15.6839 (13) Å	T = 100 K
β = 95.270 (1)°	Plate, yellow
V = 1341.78 (19) Å3	0.37 × 0.19 × 0.16 mm
Z = 4

Bruker APEX CCD diffractometer	3083 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
Tmin = 0.887, Tmax = 0.986	k = −18→18
12548 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: difmap and geom
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.035P)2 + 0.4678P] where P = (Fo2 + 2Fc2)/3
3083 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	−0.2845 (2)	0.22408 (8)	0.34560 (7)	0.0214 (3)
C2	−0.4447 (2)	0.29342 (9)	0.35331 (8)	0.0244 (3)
H2	−0.4468	0.3487	0.3198	0.029*
C3	−0.6002 (2)	0.27850 (9)	0.41161 (8)	0.0286 (3)
H3	−0.7127	0.3241	0.4176	0.034*
C4	−0.5963 (2)	0.19767 (10)	0.46224 (8)	0.0300 (3)
H4	−0.7037	0.1901	0.5027	0.036*
C5	−0.4385 (2)	0.12915 (9)	0.45400 (8)	0.0269 (3)
H5	−0.4370	0.0745	0.4883	0.032*
C6	−0.2805 (2)	0.14115 (8)	0.39445 (8)	0.0228 (3)
C7	−0.1010 (2)	0.08444 (8)	0.36710 (7)	0.0221 (3)
C8	−0.0205 (2)	−0.00614 (9)	0.38728 (8)	0.0266 (3)
H8	−0.0852	−0.0427	0.4291	0.032*
C9	0.1525 (2)	−0.04017 (8)	0.34536 (8)	0.0278 (3)
H9	0.2088	−0.1008	0.3590	0.033*
C10	0.2501 (2)	0.01264 (8)	0.28208 (8)	0.0241 (3)
C11	0.1683 (2)	0.10152 (8)	0.25993 (7)	0.0209 (3)
C12	−0.0055 (2)	0.13669 (8)	0.30376 (7)	0.0205 (2)
C13	0.4420 (2)	−0.02233 (9)	0.24051 (9)	0.0287 (3)
C14	0.5333 (2)	0.04206 (10)	0.17638 (9)	0.0299 (3)
H14A	0.5983	0.0041	0.1321	0.036*
H14B	0.6559	0.0796	0.2058	0.036*
C15	0.3590 (2)	0.10787 (9)	0.13255 (8)	0.0259 (3)
C16	0.1830 (2)	0.05565 (10)	0.07445 (8)	0.0303 (3)
H16A	0.1108	0.0086	0.1079	0.045*
H16B	0.2552	0.0250	0.0283	0.045*
H16C	0.0701	0.0998	0.0498	0.045*
C17	0.4667 (2)	0.18495 (10)	0.08453 (9)	0.0338 (3)
H17A	0.3501	0.2262	0.0578	0.051*
H17B	0.5513	0.1576	0.0401	0.051*
H17C	0.5685	0.2209	0.1245	0.051*
N1	−0.11817 (17)	0.21994 (7)	0.29049 (6)	0.0208 (2)
H1	−0.073 (2)	0.2679 (9)	0.2619 (9)	0.025*
O1	0.53069 (18)	−0.09781 (7)	0.25866 (7)	0.0406 (3)
O2	0.24499 (14)	0.15638 (6)	0.19818 (5)	0.0237 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0231 (6)	0.0209 (6)	0.0197 (6)	−0.0045 (5)	−0.0007 (5)	−0.0018 (5)
C2	0.0267 (6)	0.0219 (6)	0.0243 (6)	−0.0012 (5)	0.0006 (5)	−0.0017 (5)
C3	0.0275 (7)	0.0294 (7)	0.0289 (7)	−0.0016 (5)	0.0028 (5)	−0.0065 (5)
C4	0.0294 (7)	0.0357 (7)	0.0258 (6)	−0.0094 (6)	0.0066 (5)	−0.0050 (6)
C5	0.0329 (7)	0.0261 (6)	0.0217 (6)	−0.0099 (5)	0.0021 (5)	−0.0004 (5)
C6	0.0264 (6)	0.0212 (6)	0.0200 (6)	−0.0058 (5)	−0.0023 (5)	−0.0015 (5)
C7	0.0268 (6)	0.0193 (6)	0.0192 (6)	−0.0045 (5)	−0.0032 (5)	−0.0002 (4)
C8	0.0372 (7)	0.0196 (6)	0.0216 (6)	−0.0049 (5)	−0.0042 (5)	0.0026 (5)
C9	0.0387 (7)	0.0159 (6)	0.0265 (6)	0.0017 (5)	−0.0096 (6)	0.0000 (5)
C10	0.0279 (6)	0.0185 (6)	0.0241 (6)	0.0011 (5)	−0.0075 (5)	−0.0046 (5)
C11	0.0227 (6)	0.0188 (6)	0.0202 (6)	−0.0029 (5)	−0.0035 (5)	−0.0019 (4)
C12	0.0236 (6)	0.0164 (5)	0.0205 (6)	−0.0021 (4)	−0.0031 (5)	−0.0006 (4)
C13	0.0293 (7)	0.0236 (6)	0.0308 (7)	0.0047 (5)	−0.0096 (5)	−0.0109 (5)
C14	0.0236 (6)	0.0352 (7)	0.0302 (7)	0.0051 (5)	−0.0017 (5)	−0.0112 (6)
C15	0.0245 (6)	0.0292 (7)	0.0239 (6)	0.0003 (5)	0.0018 (5)	−0.0069 (5)
C16	0.0306 (7)	0.0344 (7)	0.0247 (6)	−0.0013 (6)	−0.0041 (5)	−0.0047 (5)
C17	0.0303 (7)	0.0396 (8)	0.0327 (7)	−0.0031 (6)	0.0091 (6)	−0.0039 (6)
N1	0.0240 (5)	0.0160 (5)	0.0226 (5)	−0.0007 (4)	0.0032 (4)	0.0024 (4)
O1	0.0426 (6)	0.0243 (5)	0.0530 (7)	0.0112 (4)	−0.0062 (5)	−0.0103 (5)
O2	0.0258 (4)	0.0218 (4)	0.0239 (4)	−0.0001 (3)	0.0048 (4)	−0.0019 (3)

C1—N1	1.3790 (16)	C10—C13	1.4617 (18)
C1—C2	1.3952 (17)	C11—O2	1.3599 (14)
C1—C6	1.4135 (17)	C11—C12	1.3942 (17)
C2—C3	1.3808 (18)	C12—N1	1.3775 (15)
C2—H2	0.9500	C13—O1	1.2275 (16)
C3—C4	1.4039 (19)	C13—C14	1.505 (2)
C3—H3	0.9500	C14—C15	1.5239 (18)
C4—C5	1.378 (2)	C14—H14A	0.9900
C4—H4	0.9500	C14—H14B	0.9900
C5—C6	1.4005 (18)	C15—O2	1.4625 (15)
C5—H5	0.9500	C15—C17	1.5148 (19)
C6—C7	1.4444 (18)	C15—C16	1.5252 (17)
C7—C12	1.4071 (17)	C16—H16A	0.9800
C7—C8	1.4111 (17)	C16—H16B	0.9800
C8—C9	1.3679 (19)	C16—H16C	0.9800
C8—H8	0.9500	C17—H17A	0.9800
C9—C10	1.4164 (19)	C17—H17B	0.9800
C9—H9	0.9500	C17—H17C	0.9800
C10—C11	1.3976 (17)	N1—H1	0.878 (12)
N1—C1—C2	128.89 (11)	N1—C12—C7	110.03 (11)
N1—C1—C6	109.04 (11)	C11—C12—C7	121.75 (11)
C2—C1—C6	121.99 (12)	O1—C13—C10	122.73 (13)
C3—C2—C1	117.32 (12)	O1—C13—C14	121.29 (13)
C3—C2—H2	121.3	C10—C13—C14	115.92 (11)
C1—C2—H2	121.3	C13—C14—C15	113.88 (11)
C2—C3—C4	121.68 (13)	C13—C14—H14A	108.8
C2—C3—H3	119.2	C15—C14—H14A	108.8
C4—C3—H3	119.2	C13—C14—H14B	108.8
C5—C4—C3	120.76 (12)	C15—C14—H14B	108.8
C5—C4—H4	119.6	H14A—C14—H14B	107.7
C3—C4—H4	119.6	O2—C15—C17	104.54 (10)
C4—C5—C6	119.14 (12)	O2—C15—C14	108.80 (10)
C4—C5—H5	120.4	C17—C15—C14	111.72 (11)
C6—C5—H5	120.4	O2—C15—C16	108.18 (10)
C5—C6—C1	119.08 (12)	C17—C15—C16	111.33 (11)
C5—C6—C7	134.14 (12)	C14—C15—C16	111.92 (11)
C1—C6—C7	106.77 (11)	C15—C16—H16A	109.5
C12—C7—C8	119.70 (12)	C15—C16—H16B	109.5
C12—C7—C6	105.79 (10)	H16A—C16—H16B	109.5
C8—C7—C6	134.42 (12)	C15—C16—H16C	109.5
C9—C8—C7	118.63 (12)	H16A—C16—H16C	109.5
C9—C8—H8	120.7	H16B—C16—H16C	109.5
C7—C8—H8	120.7	C15—C17—H17A	109.5
C8—C9—C10	121.73 (11)	C15—C17—H17B	109.5
C8—C9—H9	119.1	H17A—C17—H17B	109.5
C10—C9—H9	119.1	C15—C17—H17C	109.5
C11—C10—C9	120.25 (12)	H17A—C17—H17C	109.5
C11—C10—C13	118.29 (12)	H17B—C17—H17C	109.5
C9—C10—C13	121.42 (11)	C12—N1—C1	108.36 (10)
O2—C11—C12	117.29 (10)	C12—N1—H1	125.7 (9)
O2—C11—C10	124.80 (11)	C1—N1—H1	124.3 (9)
C12—C11—C10	117.90 (11)	C11—O2—C15	115.87 (10)
N1—C12—C11	128.09 (11)
N1—C1—C2—C3	177.14 (12)	C10—C11—C12—N1	−176.92 (11)
C6—C1—C2—C3	0.56 (18)	O2—C11—C12—C7	178.19 (10)
C1—C2—C3—C4	0.94 (19)	C10—C11—C12—C7	−1.42 (17)
C2—C3—C4—C5	−1.4 (2)	C8—C7—C12—N1	176.09 (10)
C3—C4—C5—C6	0.24 (19)	C6—C7—C12—N1	−1.00 (13)
C4—C5—C6—C1	1.21 (18)	C8—C7—C12—C11	−0.15 (18)
C4—C5—C6—C7	−177.49 (13)	C6—C7—C12—C11	−177.24 (10)
N1—C1—C6—C5	−178.83 (11)	C11—C10—C13—O1	176.81 (12)
C2—C1—C6—C5	−1.65 (17)	C9—C10—C13—O1	−1.12 (19)
N1—C1—C6—C7	0.20 (13)	C11—C10—C13—C14	−0.30 (16)
C2—C1—C6—C7	177.38 (11)	C9—C10—C13—C14	−178.23 (11)
C5—C6—C7—C12	179.29 (13)	O1—C13—C14—C15	154.37 (12)
C1—C6—C7—C12	0.48 (13)	C10—C13—C14—C15	−28.47 (15)
C5—C6—C7—C8	2.8 (2)	C13—C14—C15—O2	52.15 (14)
C1—C6—C7—C8	−175.98 (13)	C13—C14—C15—C17	167.05 (11)
C12—C7—C8—C9	1.22 (17)	C13—C14—C15—C16	−67.34 (14)
C6—C7—C8—C9	177.30 (13)	C11—C12—N1—C1	177.08 (11)
C7—C8—C9—C10	−0.71 (18)	C7—C12—N1—C1	1.15 (13)
C8—C9—C10—C11	−0.88 (18)	C2—C1—N1—C12	−177.75 (12)
C8—C9—C10—C13	177.01 (11)	C6—C1—N1—C12	−0.82 (13)
C9—C10—C11—O2	−177.66 (11)	C12—C11—O2—C15	−157.25 (10)
C13—C10—C11—O2	4.38 (17)	C10—C11—O2—C15	22.33 (16)
C9—C10—C11—C12	1.92 (17)	C17—C15—O2—C11	−168.60 (10)
C13—C10—C11—C12	−176.04 (10)	C14—C15—O2—C11	−49.13 (13)
O2—C11—C12—N1	2.69 (18)	C16—C15—O2—C11	72.67 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (1)	1.97 (1)	2.7876 (14)	154 (1)
C14—H14B···Cg1ii	0.99	2.58	3.4754 (15)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.878 (12)	1.973 (13)	2.7876 (14)	153.9 (13)
C14—H14B⋯Cg1ii	0.99	2.58	3.4754 (15)	151

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1/C6/C7/C12/N1 ring.