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

Safarov, S.; Voskressensky, L.G.; Bizhko, O.V.; Kulikova, L.N.; Khrustalev, V.N.

doi:10.1107/S1600536810006744

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o710

doi:10.1107/S1600536810006744

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

Saifidin Safarov,^a ^* Leonid G. Voskressensky,^b Oksana V. Bizhko,^b Larisa N. Kulikova ^b and Victor N. Khrustalev ^c

^aV. I. Nikitin Institute of Chemistry, Ayni St. 299/2, Dushanbe 734063, Tajikistan, ^bOrganic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklai St 6, Moscow 117198, Russian Federation, and ^cA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St 28, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: vkh@xray.ineos.ac.ru

(Received 19 February 2010; accepted 22 February 2010; online 27 February 2010)

The title compound, C₁₈H₁₂N₂O, comprises two aromatic fragments, viz., imidazo[2,1-a]isoquinoline and benzene, linked by oxygen and methylene bridges. Despite the absence of a common conjugative system within the molecule, it adopts an essentially planar conformation with an r.m.s. deviation of 0. 036 Å. In the crystal, due to this structure, molecules form stacks along the b axis by π⋯π stacking interactions, with shortest C⋯C distances in the range 3.340 (4)–3.510 (4) Å. The molecules are bound by intermolecular C—H⋯O interactions within the stacks and C—H⋯π interactions 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_r = 272.30
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.182
S = 1.00
2734 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x, y+1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Cascade reactions have emerged as powerful tools to allow rapidly increasing molecular complexity (Tietze, 1996; Parsons et al., 1996; Wasilke et al., 2005). These processes avoid the excessive handling and isolation of synthetic intermediates generating less waste and thus contribute towards "Green Chemistry". Cascade reactions, in which multiple reactions are combined into one synthetic operation, have been reported extensively in the literature and have already become "state–of–the–art" in synthetic organic chemistry (Bunce, 1995; Nicolaou et al., 2003, 2006; Pellissier, 2006a, 2006b; Parenty & Cronin, 2008).

The title compound I, C₁₈H₁₂N₂O, is the product of a novel cascade reaction (Fig. 1) (Yadav et al., 2007; Kianmehr et al., 2009; Surpur et al., 2009) starting with the Kroehnke condensation of salicylic aldehyde and isoquinolinium salt to afford the styryl derivative A, which forms zwitterion B upon thermally–induced cleavage of acetyl chloride. Then zwitterion B undergoes two consecutive nucleophilic cyclizations followed by [1,4]–proton shift to give the pentacycle I (Fig. 2). The single crystals of I suitable for X–ray diffraction analysis were obtained by slow crystallization from ethyl acetate solution.

Compound I comprises two aromatic fragments - imidazo[2,1–a]isoquinoline and benzene linked by the oxygen and methylene bridges (Fig. 3). Despite the absence of common conjugative system within the molecule, it adopts practically planar conformation, with the r.m.s. deviation of 0.036Å. In the crystal, due to this structure, molecules form stacks along the b axis by the stacking interactions [C1···C7Aⁱ = 3.340 (4)Å, C2···C8ⁱ = 3.510Å, C2···C8Aⁱ = 3.451 (4)Å, C3···C12Aⁱ = 3.394 (4)Å, C13A···C14Bⁱ = 3.496 (4)Å and C14A···C14Aⁱ = 3.426 (4)Å] (Fig. 4). The molecules are also bound by the C8—H8A···O13ⁱⁱ [H···O = 2.71Å, C—H···O 157°] interactions within the stacks and the C8—H8B···π (C12Aⁱⁱⁱ—O13ⁱⁱⁱ—C13Aⁱⁱⁱ) [H···C12A = 2.94Å, H···O13 = 2.80Å and H···C13A 2.81Å, C—H···O 175°] interactions between the stacks. Symmetry codes: (i) 1-x, 1-y, z; (ii) x, 1+y, z; (iii) 1.5-x, 0.5+y, 0.5-z.

Related literature top

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 top

A water solution of K₂CO₃(0.4 g in 1 ml of H₂O) was added to a solution of freshly distilled salicylic aldehyde (0.18 g, 1.47 mmol) and 2–(cyanomethyl)isoquinolinium chloride (0.30 g, 1.47 mmol) in H₂O (5 ml). The resulting mixture was stirred for 3 hours at 293 K. The precipitate formed was filtered–off and recrystallized from ethyl acetate / hexane mixture to give product I as colourless needles. Yield is 32%. M.p. = 444 K. Found (%): C 79.13, H4.58, N 10.53. Calcd. for C₁₈H₁₂N₂O (%): C79.39, H 4.44, N 10.29. ¹H NMR (400 MHz, CDCl₃): δ = 4.25 (s, 2H, CH₂), 6.98 (dd, 1H, H12, J_11,12 = 8.1, J_10,12 = 1.2), 7.01 (d, 1H, H5, J_5,6 = 7.5), 7.07–7.12 (m, 2H, H9+H10), 7.16 (dd, 1H, H11, J_11,12 = 8.1, J_9,11 = 1.2), 7.40–7.45 (m, 1H, H3), 7.48–7.53 (m, 1H, H2), 7.55 (d, 1H, H4, J_3,4 = 7.5), 7.58 (d, 1H, H6, J_5,6 = 7.5), 8.47(d, 1H, H1, J_1,2 = 8.1). ¹³C NMR (100 MHz, CDCl₃): δ = 23.2 (CH₂), 112.9 (CH), 117.8 (C_q), 118.1 (C_q), 118.3 (CH), 120.3 (CH), 123.1 (CH), 123.2 (C_q), 123.5 (CH), 127.1 (CH), 127.8 (CH), 128.2 (2xCH), 129.1 (C_q), 130.3 (CH), 138.0 (C_q), 152.0 (C_q), 161.1 (C_q). Mass spectrum (EI MS), m/z (I_r, %): 272 (70) [M^+.], 136 (11), 128 (10).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Synthesis of compound I.
	Fig. 2. The plausible formation mechanism of I.
	Fig. 3. Molecular structure of Iwith the atom numbering scheme. Displacement ellipsoids are shown atthe 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 4. Crystal packing of I viewed down the b axis. Dashed lines indicate the C—H···O and C—H···π interactions.

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

Crystal data top

C₁₈H₁₂N₂O	F(000) = 568
M_r = 272.30	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.077P)² + 1.7P] where P = (F_o² + 2F_c²)/3
2734 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₂N₂O	V = 1269.9 (3) Å³
M_r = 272.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.9717 (15) Å	µ = 0.09 mm⁻¹
b = 6.0580 (8) Å	T = 100 K
c = 17.948 (2) Å	0.40 × 0.12 × 0.02 mm
β = 102.682 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2734 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1821 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.998	R_int = 0.056
12413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.00	Δρ_max = 0.45 e Å⁻³
2734 reflections	Δρ_min = −0.23 e Å⁻³
190 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂O
M_r	272.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.9717 (15), 6.0580 (8), 17.948 (2)
β (°)	102.682 (3)
V (Å³)	1269.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.12 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.965, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	12413, 2734, 1821
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.182, 1.00
No. of reflections	2734
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2.

References

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Volume 66| Part 3| March 2010| Page o710

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