2,2,9-Trimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4-(11H)-one.

The title compound, C(18)H(17)NO(2), was prepared from 1-hydr-oxy-7-methyl-carbazole and 3,3-dimethyl-acrylic acid with trifluoro-acetic acid as the cyclization catalyst. The mol-ecules contain an essentially planar 6-methyl-indole unit. The second aromatic ring is significantly bent away from the plane of this unit, with maximum deviations of 0.171 (1) and 0.185 (1) Å for two of the C atoms. In the crystal structure, there are neither N-H⋯O hydrogen bonds nor π-π stacking between the aromatic sections of neighboring mol-ecules. There is only one weak C-H⋯O hydrogen bond and a number of weak C-H⋯π inter-actions.

Related literature

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 et al. (2008a ▶,b ▶) report the structures of the 9-H and 10-methyl derivatives of the title compound.

Experimental

Crystal data

C18H17NO2

M = 279.33

Monoclinic,

a = 8.6702 (7) Å

b = 6.1647 (5) Å

c = 26.617 (2) Å

β = 99.100 (1)°

V = 1404.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.57 × 0.48 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.883, T max = 0.980

12327 measured reflections

3044 independent reflections

2708 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.098

S = 1.04

3044 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.21 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/S1600536808033850/hb2804sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033850/hb2804Isup2.hkl

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

C18H17NO2	F(000) = 592
Mr = 279.33	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5407 reflections
a = 8.6702 (7) Å	θ = 2.4–27.0°
b = 6.1647 (5) Å	µ = 0.09 mm−1
c = 26.617 (2) Å	T = 100 K
β = 99.100 (1)°	Block, yellow
V = 1404.7 (2) Å3	0.57 × 0.48 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	3044 independent reflections
Radiation source: fine-focus sealed tube	2708 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
Tmin = 0.883, Tmax = 0.980	k = −7→7
12327 measured reflections	l = −33→33

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.5637P] where P = (Fo2 + 2Fc2)/3
3044 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.21 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	0.17131 (13)	0.84678 (19)	0.25979 (4)	0.0187 (2)
C2	0.09703 (13)	0.7573 (2)	0.29780 (4)	0.0211 (3)
H2	0.0487	0.6188	0.2934	0.025*
C3	0.09548 (13)	0.8752 (2)	0.34216 (4)	0.0226 (3)
C4	0.16617 (13)	1.0821 (2)	0.34766 (4)	0.0234 (3)
H4	0.1620	1.1628	0.3778	0.028*
C5	0.24143 (13)	1.1703 (2)	0.31029 (4)	0.0214 (3)
H5	0.2894	1.3090	0.3148	0.026*
C6	0.24560 (12)	1.05129 (18)	0.26567 (4)	0.0182 (2)
C7	0.31598 (12)	1.08697 (18)	0.22066 (4)	0.0183 (2)
C8	0.41054 (13)	1.25324 (19)	0.20595 (4)	0.0211 (3)
H8	0.4326	1.3796	0.2262	0.025*
C9	0.47011 (13)	1.2281 (2)	0.16144 (4)	0.0224 (3)
H9	0.5374	1.3364	0.1516	0.027*
C10	0.43349 (13)	1.04460 (19)	0.12984 (4)	0.0203 (2)
C11	0.33180 (13)	0.88417 (18)	0.14256 (4)	0.0185 (2)
C12	0.27867 (12)	0.90402 (18)	0.18939 (4)	0.0181 (2)
C13	0.01770 (15)	0.7822 (2)	0.38419 (5)	0.0301 (3)
H13A	−0.0933	0.8209	0.3784	0.045*
H13B	0.0674	0.8413	0.4170	0.045*
H13C	0.0284	0.6239	0.3846	0.045*
C14	0.50985 (13)	1.0114 (2)	0.08483 (4)	0.0237 (3)
C15	0.47085 (14)	0.7998 (2)	0.05735 (4)	0.0243 (3)
H15A	0.5436	0.6861	0.0731	0.029*
H15B	0.4857	0.8159	0.0214	0.029*
C16	0.30334 (14)	0.72833 (19)	0.05911 (4)	0.0208 (2)
C17	0.27377 (17)	0.5034 (2)	0.03665 (5)	0.0290 (3)
H17A	0.3465	0.4003	0.0558	0.043*
H17B	0.2895	0.5048	0.0010	0.043*
H17C	0.1662	0.4598	0.0386	0.043*
C18	0.18336 (14)	0.8888 (2)	0.03275 (4)	0.0229 (3)
H18A	0.0779	0.8353	0.0345	0.034*
H18B	0.1966	0.9043	−0.0030	0.034*
H18C	0.1983	1.0300	0.0497	0.034*
N1	0.19001 (11)	0.76108 (16)	0.21306 (4)	0.0199 (2)
H1	0.1519	0.6366	0.2005	0.024*
O1	0.28283 (10)	0.70934 (13)	0.11287 (3)	0.0218 (2)
O2	0.60210 (11)	1.14169 (18)	0.07137 (3)	0.0341 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0168 (5)	0.0229 (6)	0.0158 (5)	0.0018 (4)	0.0006 (4)	−0.0007 (4)
C2	0.0178 (5)	0.0256 (6)	0.0194 (6)	−0.0015 (4)	0.0019 (4)	0.0010 (5)
C3	0.0165 (5)	0.0332 (7)	0.0179 (6)	0.0040 (5)	0.0020 (4)	0.0021 (5)
C4	0.0209 (6)	0.0308 (7)	0.0178 (6)	0.0048 (5)	0.0005 (4)	−0.0051 (5)
C5	0.0198 (5)	0.0224 (6)	0.0208 (6)	0.0029 (4)	−0.0008 (4)	−0.0027 (5)
C6	0.0156 (5)	0.0204 (6)	0.0176 (5)	0.0021 (4)	−0.0007 (4)	0.0005 (4)
C7	0.0169 (5)	0.0203 (6)	0.0165 (5)	0.0018 (4)	−0.0008 (4)	0.0001 (4)
C8	0.0214 (6)	0.0205 (6)	0.0197 (6)	−0.0028 (4)	−0.0018 (4)	0.0002 (4)
C9	0.0203 (5)	0.0247 (6)	0.0210 (6)	−0.0045 (5)	−0.0009 (4)	0.0041 (5)
C10	0.0180 (5)	0.0246 (6)	0.0175 (5)	0.0004 (4)	0.0006 (4)	0.0031 (4)
C11	0.0200 (5)	0.0183 (5)	0.0166 (5)	0.0019 (4)	0.0011 (4)	0.0008 (4)
C12	0.0171 (5)	0.0189 (5)	0.0177 (5)	0.0003 (4)	0.0008 (4)	0.0018 (4)
C13	0.0265 (6)	0.0436 (8)	0.0214 (6)	−0.0001 (6)	0.0075 (5)	0.0010 (5)
C14	0.0189 (5)	0.0342 (7)	0.0174 (6)	0.0005 (5)	0.0006 (4)	0.0054 (5)
C15	0.0247 (6)	0.0308 (7)	0.0185 (6)	0.0064 (5)	0.0067 (5)	0.0027 (5)
C16	0.0276 (6)	0.0210 (6)	0.0147 (5)	0.0014 (5)	0.0061 (4)	−0.0001 (4)
C17	0.0454 (8)	0.0219 (6)	0.0214 (6)	0.0018 (5)	0.0107 (5)	−0.0023 (5)
C18	0.0246 (6)	0.0238 (6)	0.0195 (6)	0.0017 (5)	0.0014 (4)	−0.0012 (5)
N1	0.0239 (5)	0.0189 (5)	0.0170 (5)	−0.0037 (4)	0.0043 (4)	−0.0015 (4)
O1	0.0317 (4)	0.0192 (4)	0.0156 (4)	−0.0020 (3)	0.0069 (3)	−0.0008 (3)
O2	0.0287 (5)	0.0506 (6)	0.0240 (5)	−0.0135 (4)	0.0072 (4)	0.0010 (4)

C1—N1	1.3845 (14)	C11—C12	1.4010 (15)
C1—C2	1.3959 (16)	C12—N1	1.3847 (14)
C1—C6	1.4132 (16)	C13—H13A	0.9800
C2—C3	1.3887 (17)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
C3—C4	1.4123 (18)	C14—O2	1.2263 (15)
C3—C13	1.5079 (17)	C14—C15	1.5078 (18)
C4—C5	1.3843 (17)	C15—C16	1.5255 (17)
C4—H4	0.9500	C15—H15A	0.9900
C5—C6	1.4013 (16)	C15—H15B	0.9900
C5—H5	0.9500	C16—O1	1.4744 (13)
C6—C7	1.4447 (15)	C16—C17	1.5155 (17)
C7—C8	1.4064 (16)	C16—C18	1.5239 (16)
C7—C12	1.4086 (16)	C17—H17A	0.9800
C8—C9	1.3739 (17)	C17—H17B	0.9800
C8—H8	0.9500	C17—H17C	0.9800
C9—C10	1.4156 (17)	C18—H18A	0.9800
C9—H9	0.9500	C18—H18B	0.9800
C10—C11	1.4016 (16)	C18—H18C	0.9800
C10—C14	1.4718 (16)	N1—H1	0.8800
C11—O1	1.3638 (14)
N1—C1—C2	129.29 (11)	C3—C13—H13B	109.5
N1—C1—C6	108.89 (10)	H13A—C13—H13B	109.5
C2—C1—C6	121.80 (10)	C3—C13—H13C	109.5
C3—C2—C1	118.47 (11)	H13A—C13—H13C	109.5
C3—C2—H2	120.8	H13B—C13—H13C	109.5
C1—C2—H2	120.8	O2—C14—C10	123.03 (12)
C2—C3—C4	119.90 (11)	O2—C14—C15	122.10 (11)
C2—C3—C13	119.81 (12)	C10—C14—C15	114.83 (10)
C4—C3—C13	120.28 (11)	C14—C15—C16	112.12 (10)
C5—C4—C3	121.77 (11)	C14—C15—H15A	109.2
C5—C4—H4	119.1	C16—C15—H15A	109.2
C3—C4—H4	119.1	C14—C15—H15B	109.2
C4—C5—C6	118.78 (11)	C16—C15—H15B	109.2
C4—C5—H5	120.6	H15A—C15—H15B	107.9
C6—C5—H5	120.6	O1—C16—C17	105.74 (9)
C5—C6—C1	119.24 (11)	O1—C16—C18	108.67 (9)
C5—C6—C7	133.95 (11)	C17—C16—C18	110.60 (10)
C1—C6—C7	106.79 (10)	O1—C16—C15	108.32 (9)
C8—C7—C12	120.57 (10)	C17—C16—C15	110.77 (10)
C8—C7—C6	133.09 (11)	C18—C16—C15	112.48 (10)
C12—C7—C6	106.29 (10)	C16—C17—H17A	109.5
C9—C8—C7	118.24 (11)	C16—C17—H17B	109.5
C9—C8—H8	120.9	H17A—C17—H17B	109.5
C7—C8—H8	120.9	C16—C17—H17C	109.5
C8—C9—C10	121.51 (11)	H17A—C17—H17C	109.5
C8—C9—H9	119.2	H17B—C17—H17C	109.5
C10—C9—H9	119.2	C16—C18—H18A	109.5
C11—C10—C9	120.74 (11)	C16—C18—H18B	109.5
C11—C10—C14	118.66 (11)	H18A—C18—H18B	109.5
C9—C10—C14	120.47 (11)	C16—C18—H18C	109.5
O1—C11—C12	117.93 (10)	H18A—C18—H18C	109.5
O1—C11—C10	124.60 (10)	H18B—C18—H18C	109.5
C12—C11—C10	117.46 (10)	C1—N1—C12	108.55 (9)
N1—C12—C11	129.31 (10)	C1—N1—H1	125.7
N1—C12—C7	109.45 (10)	C12—N1—H1	125.7
C11—C12—C7	121.24 (10)	C11—O1—C16	115.16 (9)
C3—C13—H13A	109.5
N1—C1—C2—C3	179.15 (11)	O1—C11—C12—N1	5.46 (17)
C6—C1—C2—C3	0.73 (17)	C10—C11—C12—N1	−173.73 (11)
C1—C2—C3—C4	0.88 (17)	O1—C11—C12—C7	−175.89 (10)
C1—C2—C3—C13	−179.36 (10)	C10—C11—C12—C7	4.92 (16)
C2—C3—C4—C5	−1.64 (17)	C8—C7—C12—N1	177.69 (10)
C13—C3—C4—C5	178.61 (11)	C6—C7—C12—N1	0.03 (12)
C3—C4—C5—C6	0.72 (17)	C8—C7—C12—C11	−1.21 (16)
C4—C5—C6—C1	0.88 (16)	C6—C7—C12—C11	−178.86 (10)
C4—C5—C6—C7	−177.44 (11)	C11—C10—C14—O2	−178.92 (11)
N1—C1—C6—C5	179.66 (10)	C9—C10—C14—O2	−3.00 (18)
C2—C1—C6—C5	−1.63 (16)	C11—C10—C14—C15	−1.16 (15)
N1—C1—C6—C7	−1.60 (12)	C9—C10—C14—C15	174.76 (10)
C2—C1—C6—C7	177.11 (10)	O2—C14—C15—C16	−148.09 (12)
C5—C6—C7—C8	2.2 (2)	C10—C14—C15—C16	34.13 (14)
C1—C6—C7—C8	−176.28 (12)	C14—C15—C16—O1	−57.83 (12)
C5—C6—C7—C12	179.42 (12)	C14—C15—C16—C17	−173.36 (10)
C1—C6—C7—C12	0.95 (12)	C14—C15—C16—C18	62.29 (13)
C12—C7—C8—C9	−2.51 (16)	C2—C1—N1—C12	−176.93 (11)
C6—C7—C8—C9	174.40 (11)	C6—C1—N1—C12	1.64 (12)
C7—C8—C9—C10	2.39 (17)	C11—C12—N1—C1	177.74 (11)
C8—C9—C10—C11	1.44 (17)	C7—C12—N1—C1	−1.03 (12)
C8—C9—C10—C14	−174.39 (11)	C12—C11—O1—C16	162.98 (10)
C9—C10—C11—O1	175.84 (10)	C10—C11—O1—C16	−17.90 (15)
C14—C10—C11—O1	−8.26 (17)	C17—C16—O1—C11	168.56 (10)
C9—C10—C11—C12	−5.03 (16)	C18—C16—O1—C11	−72.69 (12)
C14—C10—C11—C12	170.87 (10)	C15—C16—O1—C11	49.79 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O2i	0.99	2.48	3.4034 (13)	155
N1—H1···Cg2ii	0.88	2.97	3.5822 (11)	128
C2—H2···Cg1ii	0.95	2.74	3.5332 (13)	141
C8—H8···Cg1iii	0.95	2.91	3.4124 (12)	114
C9—H9···Cg2iii	0.95	2.74	3.4372 (13)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2i	0.99	2.48	3.4034 (13)	155
N1—H1⋯Cg2ii	0.88	2.97	3.5822 (11)	128
C2—H2⋯Cg1ii	0.95	2.74	3.5332 (13)	141
C8—H8⋯Cg1iii	0.95	2.91	3.4124 (12)	114
C9—H9⋯Cg2iii	0.95	2.74	3.4372 (13)	130

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the N1/C1/C6/C7C12 and C1–C6 rings, respectively.