8H-Chromeno[2',3':4,5]imidazo[2,1-a]isoquinoline.

The title compound, C(18)H(12)N(2)O, comprises two aromatic fragments, viz., imidazo[2,1-a]isoquinoline and benzene, linked by oxygen and methyl-ene bridges. Despite the absence of a common conjugative system within the mol-ecule, it adopts an essentially planar conformation with an r.m.s. deviation of 0. 036 Å. In the crystal, due to this structure, mol-ecules form stacks along the b axis by π⋯π stacking inter-actions, with shortest C⋯C distances in the range 3.340 (4)-3.510 (4) Å. The mol-ecules are bound by inter-molecular C-H⋯O inter-actions within the stacks and C-H⋯π inter-actions between the stacks.

Related literature

For background to cascade reactions, see: Bunce (1995 ▶); Tietze (1996 ▶); Parsons et al. (1996 ▶); Nicolaou et al. (2003 ▶, 2006 ▶); Wasilke et al. (2005 ▶); Pellissier (2006a ▶,b ▶); Parenty & Cronin (2008 ▶). For related compounds, see: Yadav et al. (2007 ▶); Kianmehr et al. (2009 ▶); Surpur et al. (2009 ▶).

Experimental

Crystal data

C18H12N2O

M = 272.30

Monoclinic,

a = 11.9717 (15) Å

b = 6.0580 (8) Å

c = 17.948 (2) Å

β = 102.682 (3)°

V = 1269.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.12 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.965, T max = 0.998

12413 measured reflections

2734 independent reflections

1821 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.182

S = 1.00

2734 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006744/rk2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006744/rk2193Isup2.hkl

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

C18H12N2O	F(000) = 568
Mr = 272.30	Dx = 1.424 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1700 reflections
a = 11.9717 (15) Å	θ = 2.3–26.3°
b = 6.0580 (8) Å	µ = 0.09 mm−1
c = 17.948 (2) Å	T = 100 K
β = 102.682 (3)°	Needle, colourless
V = 1269.9 (3) Å3	0.40 × 0.12 × 0.02 mm
Z = 4

Bruker APEXII CCD diffractometer	2734 independent reflections
Radiation source: fine–focus sealed tube	1821 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→15
Tmin = 0.965, Tmax = 0.998	k = −7→7
12413 measured reflections	l = −22→22

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.077P)2 + 1.7P] where P = (Fo2 + 2Fc2)/3
2734 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.6165 (2)	0.1766 (5)	−0.07577 (16)	0.0290 (6)
H1	0.5719	0.0665	−0.0583	0.035*
C2	0.6436 (2)	0.1563 (5)	−0.14599 (17)	0.0349 (7)
H2	0.6185	0.0302	−0.1766	0.042*
C3	0.7068 (2)	0.3167 (6)	−0.17271 (17)	0.0372 (7)
H3	0.7237	0.3008	−0.2217	0.045*
C4	0.7447 (2)	0.4957 (5)	−0.12988 (17)	0.0349 (7)
H4	0.7885	0.6033	−0.1494	0.042*
C4A	0.7213 (2)	0.5276 (5)	−0.05755 (16)	0.0309 (6)
C5	0.7591 (2)	0.7182 (5)	−0.01180 (16)	0.0332 (7)
H5	0.8052	0.8253	−0.0295	0.040*
C6	0.7306 (2)	0.7478 (5)	0.05559 (16)	0.0310 (6)
H6	0.7538	0.8777	0.0845	0.037*
N7	0.66701 (19)	0.5884 (4)	0.08314 (13)	0.0269 (5)
C7A	0.6332 (2)	0.5823 (4)	0.15238 (15)	0.0251 (6)
C8	0.6498 (2)	0.7432 (5)	0.21381 (16)	0.0326 (7)
H8A	0.6141	0.8858	0.1950	0.039*
H8B	0.7325	0.7676	0.2349	0.039*
C8A	0.5921 (2)	0.6458 (5)	0.27520 (16)	0.0301 (6)
C9	0.5902 (2)	0.7644 (5)	0.34032 (18)	0.0347 (7)
H9	0.6261	0.9050	0.3466	0.042*
C10	0.5385 (3)	0.6886 (5)	0.39654 (18)	0.0382 (7)
H10	0.5390	0.7752	0.4407	0.046*
C11	0.4851 (2)	0.4809 (6)	0.38774 (18)	0.0387 (8)
H11	0.4483	0.4261	0.4258	0.046*
C12	0.4864 (2)	0.3558 (5)	0.32275 (16)	0.0304 (6)
H12	0.4516	0.2141	0.3163	0.037*
C12A	0.5393 (2)	0.4417 (5)	0.26757 (15)	0.0264 (6)
O13	0.53167 (16)	0.2981 (3)	0.20489 (11)	0.0319 (5)
C13A	0.5786 (2)	0.3795 (5)	0.14856 (15)	0.0297 (6)
N14	0.57698 (19)	0.2676 (4)	0.08385 (13)	0.0297 (5)
C14A	0.6311 (2)	0.3960 (5)	0.04379 (16)	0.0291 (6)
C14B	0.6554 (2)	0.3618 (5)	−0.02983 (14)	0.0278 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0230 (13)	0.0287 (15)	0.0340 (15)	−0.0002 (11)	0.0032 (11)	0.0065 (12)
C2	0.0304 (15)	0.0366 (16)	0.0339 (16)	0.0086 (13)	−0.0012 (12)	−0.0084 (13)
C3	0.0285 (15)	0.056 (2)	0.0270 (15)	0.0063 (14)	0.0051 (12)	0.0020 (14)
C4	0.0300 (15)	0.0386 (17)	0.0360 (17)	0.0009 (13)	0.0072 (12)	0.0117 (13)
C4A	0.0256 (13)	0.0281 (15)	0.0354 (16)	0.0053 (11)	−0.0012 (12)	−0.0019 (12)
C5	0.0312 (15)	0.0325 (15)	0.0360 (16)	−0.0054 (12)	0.0080 (12)	0.0073 (13)
C6	0.0333 (15)	0.0264 (14)	0.0335 (15)	0.0002 (12)	0.0078 (12)	0.0053 (12)
N7	0.0261 (11)	0.0246 (12)	0.0282 (12)	0.0025 (9)	0.0021 (9)	0.0000 (10)
C7A	0.0187 (12)	0.0265 (14)	0.0297 (14)	−0.0019 (10)	0.0045 (10)	0.0056 (11)
C8	0.0258 (14)	0.0372 (16)	0.0350 (16)	−0.0040 (12)	0.0072 (12)	−0.0058 (13)
C8A	0.0209 (13)	0.0325 (15)	0.0350 (15)	0.0021 (11)	0.0020 (11)	0.0023 (13)
C9	0.0278 (14)	0.0313 (15)	0.0440 (17)	0.0019 (12)	0.0055 (12)	0.0008 (13)
C10	0.0365 (16)	0.0407 (18)	0.0362 (16)	0.0091 (14)	0.0054 (13)	−0.0132 (14)
C11	0.0304 (15)	0.051 (2)	0.0388 (17)	0.0089 (14)	0.0175 (13)	0.0082 (15)
C12	0.0239 (13)	0.0275 (14)	0.0397 (16)	0.0001 (11)	0.0067 (12)	0.0026 (13)
C12A	0.0214 (12)	0.0294 (14)	0.0283 (14)	0.0068 (11)	0.0055 (11)	−0.0016 (11)
O13	0.0344 (11)	0.0285 (10)	0.0352 (11)	−0.0058 (8)	0.0130 (9)	−0.0022 (9)
C13A	0.0256 (14)	0.0345 (15)	0.0290 (14)	0.0048 (12)	0.0059 (11)	0.0012 (12)
N14	0.0254 (11)	0.0327 (13)	0.0314 (13)	0.0016 (10)	0.0070 (9)	0.0015 (10)
C14A	0.0252 (13)	0.0257 (14)	0.0347 (15)	0.0004 (11)	0.0029 (11)	−0.0018 (12)
C14B	0.0227 (13)	0.0376 (16)	0.0214 (13)	0.0105 (11)	0.0014 (10)	0.0021 (12)

C1—C2	1.374 (4)	C8—C8A	1.540 (4)
C1—C14B	1.410 (4)	C8—H8A	0.9900
C1—H1	0.9500	C8—H8B	0.9900
C2—C3	1.380 (5)	C8A—C9	1.377 (4)
C2—H2	0.9500	C8A—C12A	1.382 (4)
C3—C4	1.349 (5)	C9—C10	1.373 (4)
C3—H3	0.9500	C9—H9	0.9500
C4—C4A	1.400 (4)	C10—C11	1.405 (5)
C4—H4	0.9500	C10—H10	0.9500
C4A—C5	1.432 (4)	C11—C12	1.394 (4)
C4A—C14B	1.432 (4)	C11—H11	0.9500
C5—C6	1.339 (4)	C12—C12A	1.389 (4)
C5—H5	0.9500	C12—H12	0.9500
C6—N7	1.386 (4)	C12A—O13	1.409 (3)
C6—H6	0.9500	O13—C13A	1.353 (3)
N7—C14A	1.382 (4)	C13A—N14	1.341 (4)
N7—C7A	1.390 (4)	N14—C14A	1.321 (4)
C7A—C13A	1.386 (4)	C14A—C14B	1.429 (4)
C7A—C8	1.452 (4)
C2—C1—C14B	119.6 (3)	C8A—C8—H8B	110.5
C2—C1—H1	120.2	H8A—C8—H8B	108.7
C14B—C1—H1	120.2	C9—C8A—C12A	117.3 (3)
C1—C2—C3	120.9 (3)	C9—C8A—C8	120.1 (3)
C1—C2—H2	119.6	C12A—C8A—C8	122.6 (3)
C3—C2—H2	119.6	C10—C9—C8A	122.9 (3)
C4—C3—C2	120.6 (3)	C10—C9—H9	118.5
C4—C3—H3	119.7	C8A—C9—H9	118.5
C2—C3—H3	119.7	C9—C10—C11	119.0 (3)
C3—C4—C4A	121.9 (3)	C9—C10—H10	120.5
C3—C4—H4	119.0	C11—C10—H10	120.5
C4A—C4—H4	119.0	C12—C11—C10	119.5 (3)
C4—C4A—C5	122.7 (3)	C12—C11—H11	120.2
C4—C4A—C14B	117.6 (3)	C10—C11—H11	120.2
C5—C4A—C14B	119.7 (3)	C12A—C12—C11	118.9 (3)
C6—C5—C4A	121.0 (3)	C12A—C12—H12	120.5
C6—C5—H5	119.5	C11—C12—H12	120.5
C4A—C5—H5	119.5	C8A—C12A—C12	122.4 (3)
C5—C6—N7	119.9 (3)	C8A—C12A—O13	125.4 (2)
C5—C6—H6	120.1	C12—C12A—O13	112.2 (2)
N7—C6—H6	120.1	C13A—O13—C12A	114.0 (2)
C14A—N7—C6	122.6 (2)	N14—C13A—O13	122.2 (3)
C14A—N7—C7A	108.4 (2)	N14—C13A—C7A	114.1 (2)
C6—N7—C7A	129.0 (2)	O13—C13A—C7A	123.7 (2)
C13A—C7A—N7	101.9 (2)	C14A—N14—C13A	104.9 (2)
C13A—C7A—C8	128.1 (2)	N14—C14A—N7	110.7 (2)
N7—C7A—C8	130.0 (2)	N14—C14A—C14B	129.9 (3)
C7A—C8—C8A	106.1 (2)	N7—C14A—C14B	119.4 (3)
C7A—C8—H8A	110.5	C1—C14B—C14A	123.3 (3)
C8A—C8—H8A	110.5	C1—C14B—C4A	119.4 (2)
C7A—C8—H8B	110.5	C14A—C14B—C4A	117.3 (3)
C14B—C1—C2—C3	−1.1 (4)	C11—C12—C12A—O13	−178.9 (2)
C1—C2—C3—C4	0.9 (4)	C8A—C12A—O13—C13A	−2.1 (4)
C2—C3—C4—C4A	−0.5 (4)	C12—C12A—O13—C13A	177.7 (2)
C3—C4—C4A—C5	−178.9 (3)	C12A—O13—C13A—N14	−178.5 (2)
C3—C4—C4A—C14B	0.2 (4)	C12A—O13—C13A—C7A	2.1 (4)
C4—C4A—C5—C6	176.9 (3)	N7—C7A—C13A—N14	−0.3 (3)
C14B—C4A—C5—C6	−2.3 (4)	C8—C7A—C13A—N14	180.0 (3)
C4A—C5—C6—N7	2.4 (4)	N7—C7A—C13A—O13	179.1 (2)
C5—C6—N7—C14A	0.2 (4)	C8—C7A—C13A—O13	−0.6 (4)
C5—C6—N7—C7A	176.8 (3)	O13—C13A—N14—C14A	−179.3 (2)
C14A—N7—C7A—C13A	0.3 (3)	C7A—C13A—N14—C14A	0.1 (3)
C6—N7—C7A—C13A	−176.7 (3)	C13A—N14—C14A—N7	0.1 (3)
C14A—N7—C7A—C8	−179.9 (3)	C13A—N14—C14A—C14B	179.9 (3)
C6—N7—C7A—C8	3.1 (5)	C6—N7—C14A—N14	177.0 (2)
C13A—C7A—C8—C8A	−1.0 (4)	C7A—N7—C14A—N14	−0.3 (3)
N7—C7A—C8—C8A	179.3 (2)	C6—N7—C14A—C14B	−2.8 (4)
C7A—C8—C8A—C9	−177.9 (2)	C7A—N7—C14A—C14B	179.9 (2)
C7A—C8—C8A—C12A	1.0 (4)	C2—C1—C14B—C14A	179.9 (3)
C12A—C8A—C9—C10	−0.1 (4)	C2—C1—C14B—C4A	0.8 (4)
C8—C8A—C9—C10	178.9 (3)	N14—C14A—C14B—C1	3.9 (4)
C8A—C9—C10—C11	0.0 (4)	N7—C14A—C14B—C1	−176.3 (2)
C9—C10—C11—C12	0.6 (4)	N14—C14A—C14B—C4A	−176.9 (3)
C10—C11—C12—C12A	−1.0 (4)	N7—C14A—C14B—C4A	2.8 (4)
C9—C8A—C12A—C12	−0.4 (4)	C4—C4A—C14B—C1	−0.4 (4)
C8—C8A—C12A—C12	−179.3 (2)	C5—C4A—C14B—C1	178.8 (2)
C9—C8A—C12A—O13	179.4 (2)	C4—C4A—C14B—C14A	−179.5 (2)
C8—C8A—C12A—O13	0.5 (4)	C5—C4A—C14B—C14A	−0.4 (4)
C11—C12—C12A—C8A	0.9 (4)

Cg2 is the centroid of the O13,C12A,C8A,C8,C7A,C13A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O13i	0.99	2.71	3.637 (4)	157
C8—H8B···Cgii	0.99	2.63	3.547 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the O13,C12A,C8A,C8,C7A,C13A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O13i	0.99	2.71	3.637 (4)	157
C8—H8B⋯Cgii	0.99	2.63	3.547 (3)	154

Symmetry codes: (i) ; (ii) .