2,2,10-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-8-methyl-carbazole and 3,3-dimethyl-acrylic acid with trifluoro-acetic acid as the cyclization catalyst. Due to the -CMe(2)- group, the mol-ecule is not quite planar. The packing is dominated by the strong N-H⋯O hydrogen bonds and some weaker C-H⋯O and C-H⋯π inter-actions. π-π Stacking inter-actions [centroid-centroid separation = 3.806 (2) Å] join neighboring mol-ecules into loosely connected inversion dimers.

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, Rajendra Prasad & Zeller (2008 ▶) report the structure of the 9-methyl derivative of the title compound. Sridharan, Rajendra Prasad, Ngendahimana et al. (2008 ▶) report the structure of the 10-H derivative of the title compound.

Experimental

Crystal data

C18H17NO2

M = 279.33

Monoclinic,

a = 12.9740 (16) Å

b = 9.4195 (12) Å

c = 12.8444 (16) Å

β = 114.733 (2)°

V = 1425.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.53 × 0.43 × 0.19 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.886, T max = 0.984

13755 measured reflections

3526 independent reflections

2941 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.03

3526 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 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/S1600536808033862/hb2805sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033862/hb2805Isup2.hkl

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

C18H17NO2	F(000) = 592
Mr = 279.33	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4194 reflections
a = 12.9740 (16) Å	θ = 2.8–31.5°
b = 9.4195 (12) Å	µ = 0.09 mm−1
c = 12.8444 (16) Å	T = 100 K
β = 114.733 (2)°	Plate, yellow
V = 1425.7 (3) Å3	0.53 × 0.43 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	3526 independent reflections
Radiation source: fine-focus sealed tube	2941 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→17
Tmin = 0.886, Tmax = 0.984	k = −12→12
13755 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.5237P] where P = (Fo2 + 2Fc2)/3
3526 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.26 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	0.30161 (12)	1.23026 (14)	0.61446 (11)	0.0287 (3)
H1A	0.3274	1.1580	0.6749	0.043*
H1B	0.2199	1.2193	0.5680	0.043*
H1C	0.3168	1.3249	0.6493	0.043*
C2	0.36377 (10)	1.21263 (12)	0.53998 (10)	0.0205 (2)
C3	0.44870 (10)	1.30290 (13)	0.54197 (11)	0.0235 (3)
H3	0.4698	1.3806	0.5939	0.028*
C4	0.50503 (11)	1.28432 (13)	0.47042 (11)	0.0244 (3)
H4	0.5636	1.3484	0.4757	0.029*
C5	0.47647 (10)	1.17431 (13)	0.39258 (10)	0.0217 (2)
H5	0.5142	1.1624	0.3437	0.026*
C6	0.39071 (10)	1.08061 (12)	0.38720 (10)	0.0186 (2)
C7	0.33727 (9)	1.09998 (12)	0.46184 (10)	0.0178 (2)
C8	0.25796 (9)	0.90879 (12)	0.35603 (9)	0.0165 (2)
C9	0.33879 (9)	0.95775 (12)	0.31816 (10)	0.0176 (2)
C10	0.35259 (10)	0.88720 (13)	0.22829 (10)	0.0197 (2)
H10	0.4078	0.9184	0.2029	0.024*
C11	0.28477 (10)	0.77237 (13)	0.17803 (10)	0.0199 (2)
H11	0.2932	0.7246	0.1169	0.024*
C12	0.20236 (10)	0.72342 (12)	0.21537 (10)	0.0176 (2)
C13	0.19004 (9)	0.79075 (12)	0.30620 (10)	0.0165 (2)
C14	0.06708 (10)	0.60905 (12)	0.32183 (10)	0.0208 (2)
C15	0.03119 (10)	0.58064 (13)	0.19434 (10)	0.0199 (2)
H15A	0.0054	0.4810	0.1773	0.024*
H15B	−0.0338	0.6428	0.1493	0.024*
C16	0.12561 (10)	0.60623 (12)	0.15718 (10)	0.0186 (2)
C17	0.15681 (12)	0.50413 (14)	0.39605 (11)	0.0288 (3)
H17A	0.2229	0.5095	0.3778	0.043*
H17B	0.1255	0.4078	0.3811	0.043*
H17C	0.1798	0.5275	0.4771	0.043*
C18	−0.03389 (12)	0.61299 (15)	0.35277 (12)	0.0302 (3)
H18A	−0.0085	0.6424	0.4329	0.045*
H18B	−0.0681	0.5183	0.3425	0.045*
H18C	−0.0902	0.6808	0.3029	0.045*
N1	0.25730 (8)	0.99440 (10)	0.44254 (8)	0.0176 (2)
H1	0.2137	0.9838	0.4791	0.021*
O1	0.11424 (7)	0.75262 (9)	0.34888 (7)	0.01967 (19)
O2	0.13335 (7)	0.53564 (10)	0.08062 (7)	0.0245 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0343 (7)	0.0268 (7)	0.0265 (6)	−0.0040 (5)	0.0145 (6)	−0.0059 (5)
C2	0.0223 (6)	0.0185 (5)	0.0189 (5)	0.0003 (4)	0.0068 (5)	0.0011 (4)
C3	0.0256 (6)	0.0190 (6)	0.0220 (6)	−0.0024 (5)	0.0061 (5)	0.0003 (4)
C4	0.0227 (6)	0.0229 (6)	0.0251 (6)	−0.0052 (5)	0.0076 (5)	0.0031 (5)
C5	0.0201 (6)	0.0238 (6)	0.0215 (6)	−0.0018 (5)	0.0090 (5)	0.0040 (5)
C6	0.0187 (5)	0.0185 (5)	0.0182 (5)	0.0004 (4)	0.0074 (4)	0.0025 (4)
C7	0.0173 (5)	0.0168 (5)	0.0185 (5)	0.0008 (4)	0.0068 (4)	0.0031 (4)
C8	0.0177 (5)	0.0170 (5)	0.0160 (5)	0.0018 (4)	0.0083 (4)	0.0024 (4)
C9	0.0175 (5)	0.0179 (5)	0.0182 (5)	0.0002 (4)	0.0083 (4)	0.0032 (4)
C10	0.0192 (5)	0.0229 (6)	0.0209 (6)	−0.0001 (4)	0.0122 (5)	0.0022 (4)
C11	0.0214 (6)	0.0230 (6)	0.0191 (5)	0.0014 (4)	0.0121 (5)	0.0002 (4)
C12	0.0181 (5)	0.0185 (5)	0.0182 (5)	0.0008 (4)	0.0096 (4)	0.0011 (4)
C13	0.0163 (5)	0.0176 (5)	0.0177 (5)	0.0015 (4)	0.0090 (4)	0.0024 (4)
C14	0.0255 (6)	0.0189 (6)	0.0219 (6)	−0.0073 (4)	0.0137 (5)	−0.0034 (4)
C15	0.0200 (5)	0.0218 (6)	0.0200 (5)	−0.0038 (4)	0.0104 (5)	−0.0035 (4)
C16	0.0199 (5)	0.0197 (6)	0.0177 (5)	0.0019 (4)	0.0093 (4)	0.0019 (4)
C17	0.0388 (7)	0.0219 (6)	0.0242 (6)	−0.0039 (5)	0.0117 (6)	0.0022 (5)
C18	0.0349 (7)	0.0347 (7)	0.0312 (7)	−0.0148 (6)	0.0237 (6)	−0.0103 (6)
N1	0.0196 (5)	0.0175 (5)	0.0183 (5)	−0.0013 (4)	0.0106 (4)	−0.0008 (4)
O1	0.0229 (4)	0.0189 (4)	0.0231 (4)	−0.0050 (3)	0.0155 (4)	−0.0034 (3)
O2	0.0277 (5)	0.0264 (5)	0.0239 (4)	−0.0031 (4)	0.0153 (4)	−0.0064 (3)

C1—C2	1.4963 (18)	C11—C12	1.4195 (16)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.3945 (16)
C1—H1C	0.9800	C12—C16	1.4649 (16)
C2—C3	1.3836 (17)	C13—O1	1.3594 (13)
C2—C7	1.4010 (16)	C14—O1	1.4650 (13)
C3—C4	1.4040 (19)	C14—C18	1.5202 (17)
C3—H3	0.9500	C14—C17	1.5205 (18)
C4—C5	1.3787 (18)	C14—C15	1.5270 (16)
C4—H4	0.9500	C15—C16	1.5086 (16)
C5—C6	1.3991 (16)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.4103 (16)	C16—O2	1.2254 (14)
C6—C9	1.4420 (16)	C17—H17A	0.9800
C7—N1	1.3826 (14)	C17—H17B	0.9800
C8—N1	1.3759 (14)	C17—H17C	0.9800
C8—C13	1.3966 (16)	C18—H18A	0.9800
C8—C9	1.4057 (15)	C18—H18B	0.9800
C9—C10	1.4068 (16)	C18—H18C	0.9800
C10—C11	1.3732 (17)	N1—H1	0.8800
C10—H10	0.9500
C2—C1—H1A	109.5	C13—C12—C16	118.57 (10)
C2—C1—H1B	109.5	C11—C12—C16	121.31 (10)
H1A—C1—H1B	109.5	O1—C13—C12	124.94 (10)
C2—C1—H1C	109.5	O1—C13—C8	116.73 (10)
H1A—C1—H1C	109.5	C12—C13—C8	118.31 (10)
H1B—C1—H1C	109.5	O1—C14—C18	103.62 (9)
C3—C2—C7	115.69 (11)	O1—C14—C17	108.49 (10)
C3—C2—C1	123.92 (11)	C18—C14—C17	111.68 (11)
C7—C2—C1	120.39 (11)	O1—C14—C15	109.02 (9)
C2—C3—C4	122.68 (12)	C18—C14—C15	112.03 (10)
C2—C3—H3	118.7	C17—C14—C15	111.62 (10)
C4—C3—H3	118.7	C16—C15—C14	112.81 (9)
C5—C4—C3	120.85 (11)	C16—C15—H15A	109.0
C5—C4—H4	119.6	C14—C15—H15A	109.0
C3—C4—H4	119.6	C16—C15—H15B	109.0
C4—C5—C6	118.48 (11)	C14—C15—H15B	109.0
C4—C5—H5	120.8	H15A—C15—H15B	107.8
C6—C5—H5	120.8	O2—C16—C12	123.50 (11)
C5—C6—C7	119.46 (11)	O2—C16—C15	121.14 (11)
C5—C6—C9	133.93 (11)	C12—C16—C15	115.31 (10)
C7—C6—C9	106.61 (10)	C14—C17—H17A	109.5
N1—C7—C2	127.88 (11)	C14—C17—H17B	109.5
N1—C7—C6	109.30 (10)	H17A—C17—H17B	109.5
C2—C7—C6	122.81 (11)	C14—C17—H17C	109.5
N1—C8—C13	128.38 (10)	H17A—C17—H17C	109.5
N1—C8—C9	110.17 (10)	H17B—C17—H17C	109.5
C13—C8—C9	121.44 (10)	C14—C18—H18A	109.5
C8—C9—C10	119.89 (11)	C14—C18—H18B	109.5
C8—C9—C6	105.94 (10)	H18A—C18—H18B	109.5
C10—C9—C6	134.16 (11)	C14—C18—H18C	109.5
C11—C10—C9	118.78 (10)	H18A—C18—H18C	109.5
C11—C10—H10	120.6	H18B—C18—H18C	109.5
C9—C10—H10	120.6	C8—N1—C7	107.97 (10)
C10—C11—C12	121.47 (11)	C8—N1—H1	126.0
C10—C11—H11	119.3	C7—N1—H1	126.0
C12—C11—H11	119.3	C13—O1—C14	116.68 (9)
C13—C12—C11	120.07 (11)
C7—C2—C3—C4	0.25 (18)	C11—C12—C13—O1	−179.88 (10)
C1—C2—C3—C4	−179.51 (12)	C16—C12—C13—O1	2.67 (17)
C2—C3—C4—C5	0.89 (19)	C11—C12—C13—C8	1.94 (17)
C3—C4—C5—C6	−0.60 (18)	C16—C12—C13—C8	−175.51 (10)
C4—C5—C6—C7	−0.79 (17)	N1—C8—C13—O1	−1.17 (17)
C4—C5—C6—C9	179.38 (12)	C9—C8—C13—O1	−179.73 (10)
C3—C2—C7—N1	179.55 (11)	N1—C8—C13—C12	177.16 (11)
C1—C2—C7—N1	−0.67 (19)	C9—C8—C13—C12	−1.39 (16)
C3—C2—C7—C6	−1.70 (17)	O1—C14—C15—C16	53.97 (13)
C1—C2—C7—C6	178.07 (11)	C18—C14—C15—C16	168.06 (10)
C5—C6—C7—N1	−179.03 (10)	C17—C14—C15—C16	−65.85 (13)
C9—C6—C7—N1	0.84 (13)	C13—C12—C16—O2	−176.05 (11)
C5—C6—C7—C2	2.02 (17)	C11—C12—C16—O2	6.53 (18)
C9—C6—C7—C2	−178.11 (10)	C13—C12—C16—C15	6.45 (15)
N1—C8—C9—C10	−178.90 (10)	C11—C12—C16—C15	−170.97 (11)
C13—C8—C9—C10	−0.10 (17)	C14—C15—C16—O2	147.37 (11)
N1—C8—C9—C6	0.40 (12)	C14—C15—C16—C12	−35.06 (14)
C13—C8—C9—C6	179.19 (10)	C13—C8—N1—C7	−178.57 (11)
C5—C6—C9—C8	179.10 (12)	C9—C8—N1—C7	0.12 (12)
C7—C6—C9—C8	−0.74 (12)	C2—C7—N1—C8	178.28 (11)
C5—C6—C9—C10	−1.8 (2)	C6—C7—N1—C8	−0.60 (12)
C7—C6—C9—C10	178.40 (12)	C12—C13—O1—C14	18.95 (16)
C8—C9—C10—C11	1.04 (17)	C8—C13—O1—C14	−162.84 (10)
C6—C9—C10—C11	−178.01 (12)	C18—C14—O1—C13	−165.62 (10)
C9—C10—C11—C12	−0.48 (17)	C17—C14—O1—C13	75.58 (12)
C10—C11—C12—C13	−1.04 (18)	C15—C14—O1—C13	−46.16 (13)
C10—C11—C12—C16	176.35 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	1.99	2.8634 (13)	173
C15—H15A···O1ii	0.99	2.59	3.5411 (15)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	1.99	2.8634 (13)	173
C15—H15A⋯O1ii	0.99	2.59	3.5411 (15)	161

Symmetry codes: (i) ; (ii) .