5-Phenyl-7,8-dihydro-1,3-dioxano[4,5-g]isoquinoline.

In the title compound, C(16)H(13)NO(2), the two benzene rings make a dihedral angle of 55.5 (2)°. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds and weak π-π stacking inter-actions [centroid-centroid distance = 3.595 (3)Å], linking the mol-ecules into ladders of inversion dimers.

Related literature

For details of the biological activities of isoquinolinone compounds, see: Bentley (2000 ▶); Jayaraman et al. (2002 ▶). For the Bischler–Napieralski reaction, see: Bischler & Napieralski (1893 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13NO2

M = 251.27

Triclinic,

a = 8.5005 (17) Å

b = 8.5297 (17) Å

c = 10.143 (2) Å

α = 109.07 (3)°

β = 109.44 (2)°

γ = 99.70 (3)°

V = 622.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.28 × 0.10 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.976, T max = 0.993

4801 measured reflections

2145 independent reflections

1275 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.143

S = 1.13

2145 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035009/hg2432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035009/hg2432Isup2.hkl

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

C16H13NO2	Z = 2
Mr = 251.27	F000 = 264
Triclinic, P1	Dx = 1.340 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.5005 (17) Å	Cell parameters from 1451 reflections
b = 8.5297 (17) Å	θ = 2.5–23.4º
c = 10.143 (2) Å	µ = 0.09 mm−1
α = 109.07 (3)º	T = 293 (2) K
β = 109.44 (2)º	Block, colorless
γ = 99.70 (3)º	0.28 × 0.10 × 0.08 mm
V = 622.9 (2) Å3

Rigaku R-AXIS RAPID IP area-detector diffractometer	2145 independent reflections
Radiation source: Rotating Anode	1275 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 293(2) K	θmax = 25.0º
ω oscillation scans	θmin = 3.1º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.976, Tmax = 0.993	k = −10→10
4801 measured reflections	l = −11→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.1397P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.144	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.20 e Å−3
2145 reflections	Δρmin = −0.20 e Å−3
173 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (8)
Secondary atom site location: difference Fourier map

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
O1	0.9151 (2)	0.7157 (2)	1.18121 (17)	0.0688 (6)
O2	0.6920 (2)	0.4574 (2)	1.01260 (17)	0.0656 (6)
N1	0.8054 (3)	0.6182 (3)	0.5069 (2)	0.0638 (6)
C1	0.5553 (3)	0.2889 (4)	0.3031 (3)	0.0614 (7)
H1B	0.5296	0.3808	0.2795	0.074*
C2	0.4741 (4)	0.1204 (4)	0.1932 (3)	0.0734 (8)
H2A	0.3938	0.0996	0.0961	0.088*
C3	0.5097 (4)	−0.0172 (4)	0.2247 (3)	0.0772 (9)
H3A	0.4550	−0.1308	0.1496	0.093*
C4	0.6281 (4)	0.0149 (4)	0.3695 (3)	0.0692 (8)
H4A	0.6521	−0.0779	0.3924	0.083*
C5	0.7107 (3)	0.1825 (3)	0.4798 (3)	0.0579 (7)
H5A	0.7914	0.2022	0.5765	0.069*
C6	0.6756 (3)	0.3230 (3)	0.4491 (2)	0.0511 (6)
C7	0.7705 (3)	0.5073 (3)	0.5614 (2)	0.0521 (6)
C8	0.9013 (4)	0.7997 (3)	0.6168 (3)	0.0679 (8)
H8A	0.8187	0.8570	0.6406	0.081*
H8B	0.9573	0.8600	0.5702	0.081*
C9	1.0385 (4)	0.8139 (3)	0.7632 (3)	0.0604 (7)
H9A	1.1279	0.7664	0.7424	0.072*
H9B	1.0943	0.9354	0.8351	0.072*
C10	0.9508 (3)	0.7137 (3)	0.8300 (2)	0.0497 (6)
C11	0.8169 (3)	0.5585 (3)	0.7272 (2)	0.0468 (6)
C12	0.7220 (3)	0.4618 (3)	0.7802 (2)	0.0490 (6)
H12A	0.6326	0.3575	0.7130	0.059*
C13	0.7659 (3)	0.5266 (3)	0.9336 (2)	0.0492 (6)
C14	0.8994 (3)	0.6795 (3)	1.0347 (2)	0.0510 (6)
C15	0.9955 (3)	0.7752 (3)	0.9871 (2)	0.0525 (6)
H15A	1.0871	0.8771	1.0566	0.063*
C16	0.7728 (4)	0.5854 (4)	1.1664 (3)	0.0713 (8)
H16A	0.8159	0.5318	1.2363	0.086*
H16B	0.6882	0.6379	1.1918	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0833 (14)	0.0751 (12)	0.0399 (9)	0.0155 (10)	0.0240 (9)	0.0202 (8)
O2	0.0861 (14)	0.0677 (11)	0.0470 (10)	0.0158 (10)	0.0377 (9)	0.0221 (9)
N1	0.0805 (16)	0.0671 (14)	0.0497 (12)	0.0199 (12)	0.0329 (11)	0.0267 (11)
C1	0.0513 (15)	0.0779 (18)	0.0514 (15)	0.0196 (13)	0.0185 (12)	0.0255 (14)
C2	0.0562 (17)	0.091 (2)	0.0482 (15)	0.0073 (15)	0.0087 (12)	0.0213 (15)
C3	0.080 (2)	0.0689 (18)	0.0552 (16)	0.0037 (16)	0.0187 (14)	0.0116 (14)
C4	0.079 (2)	0.0613 (16)	0.0564 (16)	0.0162 (14)	0.0246 (14)	0.0179 (13)
C5	0.0633 (16)	0.0625 (15)	0.0404 (13)	0.0169 (13)	0.0184 (11)	0.0168 (12)
C6	0.0522 (15)	0.0630 (15)	0.0383 (12)	0.0164 (12)	0.0232 (10)	0.0173 (11)
C7	0.0588 (16)	0.0615 (15)	0.0433 (12)	0.0229 (12)	0.0272 (11)	0.0221 (12)
C8	0.087 (2)	0.0622 (16)	0.0626 (16)	0.0183 (14)	0.0396 (15)	0.0296 (14)
C9	0.0646 (17)	0.0594 (15)	0.0592 (15)	0.0142 (12)	0.0327 (13)	0.0223 (12)
C10	0.0498 (14)	0.0533 (13)	0.0471 (13)	0.0170 (11)	0.0226 (11)	0.0190 (11)
C11	0.0517 (14)	0.0525 (13)	0.0393 (12)	0.0180 (11)	0.0220 (10)	0.0186 (10)
C12	0.0533 (15)	0.0522 (13)	0.0427 (12)	0.0180 (11)	0.0221 (10)	0.0178 (11)
C13	0.0587 (15)	0.0553 (14)	0.0405 (12)	0.0199 (11)	0.0273 (11)	0.0202 (11)
C14	0.0596 (16)	0.0587 (14)	0.0359 (12)	0.0255 (12)	0.0197 (11)	0.0178 (11)
C15	0.0507 (14)	0.0560 (14)	0.0458 (13)	0.0150 (11)	0.0187 (11)	0.0171 (11)
C16	0.087 (2)	0.0816 (19)	0.0449 (14)	0.0216 (16)	0.0341 (14)	0.0215 (14)

O1—C14	1.370 (3)	C7—C11	1.481 (3)
O1—C16	1.427 (3)	C8—C9	1.504 (4)
O2—C13	1.381 (3)	C8—H8A	0.9700
O2—C16	1.421 (3)	C8—H8B	0.9700
N1—C7	1.283 (3)	C9—C10	1.499 (3)
N1—C8	1.465 (3)	C9—H9A	0.9700
C1—C2	1.375 (4)	C9—H9B	0.9700
C1—C6	1.391 (3)	C10—C11	1.391 (3)
C1—H1B	0.9300	C10—C15	1.394 (3)
C2—C3	1.368 (4)	C11—C12	1.406 (3)
C2—H2A	0.9300	C12—C13	1.359 (3)
C3—C4	1.380 (4)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.376 (3)
C4—C5	1.372 (3)	C14—C15	1.364 (3)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.387 (3)	C16—H16A	0.9700
C5—H5A	0.9300	C16—H16B	0.9700
C6—C7	1.487 (3)
C14—O1—C16	105.44 (18)	C10—C9—C8	108.3 (2)
C13—O2—C16	105.24 (18)	C10—C9—H9A	110.0
C7—N1—C8	117.11 (19)	C8—C9—H9A	110.0
C2—C1—C6	120.6 (3)	C10—C9—H9B	110.0
C2—C1—H1B	119.7	C8—C9—H9B	110.0
C6—C1—H1B	119.7	H9A—C9—H9B	108.4
C3—C2—C1	120.9 (3)	C11—C10—C15	121.1 (2)
C3—C2—H2A	119.6	C11—C10—C9	116.9 (2)
C1—C2—H2A	119.6	C15—C10—C9	122.0 (2)
C2—C3—C4	119.1 (3)	C10—C11—C12	120.3 (2)
C2—C3—H3A	120.5	C10—C11—C7	117.7 (2)
C4—C3—H3A	120.5	C12—C11—C7	121.8 (2)
C5—C4—C3	120.5 (3)	C13—C12—C11	117.4 (2)
C5—C4—H4A	119.7	C13—C12—H12A	121.3
C3—C4—H4A	119.7	C11—C12—H12A	121.3
C4—C5—C6	120.9 (2)	C12—C13—C14	121.9 (2)
C4—C5—H5A	119.6	C12—C13—O2	128.3 (2)
C6—C5—H5A	119.6	C14—C13—O2	109.77 (19)
C5—C6—C1	118.0 (2)	C15—C14—O1	127.9 (2)
C5—C6—C7	122.7 (2)	C15—C14—C13	122.1 (2)
C1—C6—C7	119.0 (2)	O1—C14—C13	110.0 (2)
N1—C7—C11	122.4 (2)	C14—C15—C10	117.2 (2)
N1—C7—C6	116.7 (2)	C14—C15—H15A	121.4
C11—C7—C6	120.8 (2)	C10—C15—H15A	121.4
N1—C8—C9	112.5 (2)	O2—C16—O1	108.54 (19)
N1—C8—H8A	109.1	O2—C16—H16A	110.0
C9—C8—H8A	109.1	O1—C16—H16A	110.0
N1—C8—H8B	109.1	O2—C16—H16B	110.0
C9—C8—H8B	109.1	O1—C16—H16B	110.0
H8A—C8—H8B	107.8	H16A—C16—H16B	108.4
C6—C1—C2—C3	−0.1 (4)	N1—C7—C11—C10	−22.2 (4)
C1—C2—C3—C4	0.5 (5)	C6—C7—C11—C10	159.5 (2)
C2—C3—C4—C5	−0.8 (5)	N1—C7—C11—C12	153.3 (3)
C3—C4—C5—C6	0.9 (4)	C6—C7—C11—C12	−25.0 (4)
C4—C5—C6—C1	−0.5 (4)	C10—C11—C12—C13	0.3 (4)
C4—C5—C6—C7	−175.7 (2)	C7—C11—C12—C13	−175.0 (2)
C2—C1—C6—C5	0.1 (4)	C11—C12—C13—C14	−0.9 (4)
C2—C1—C6—C7	175.6 (2)	C11—C12—C13—O2	179.4 (2)
C8—N1—C7—C11	2.5 (4)	C16—O2—C13—C12	−173.7 (3)
C8—N1—C7—C6	−179.1 (2)	C16—O2—C13—C14	6.5 (3)
C5—C6—C7—N1	142.5 (3)	C16—O1—C14—C15	174.1 (3)
C1—C6—C7—N1	−32.7 (3)	C16—O1—C14—C13	−5.3 (3)
C5—C6—C7—C11	−39.2 (3)	C12—C13—C14—C15	0.0 (4)
C1—C6—C7—C11	145.6 (2)	O2—C13—C14—C15	179.8 (2)
C7—N1—C8—C9	37.6 (3)	C12—C13—C14—O1	179.4 (2)
N1—C8—C9—C10	−56.4 (3)	O2—C13—C14—O1	−0.8 (3)
C8—C9—C10—C11	37.8 (3)	O1—C14—C15—C10	−178.0 (2)
C8—C9—C10—C15	−139.8 (3)	C13—C14—C15—C10	1.3 (4)
C15—C10—C11—C12	1.0 (4)	C11—C10—C15—C14	−1.8 (4)
C9—C10—C11—C12	−176.6 (2)	C9—C10—C15—C14	175.7 (2)
C15—C10—C11—C7	176.5 (2)	C13—O2—C16—O1	−9.7 (3)
C9—C10—C11—C7	−1.1 (3)	C14—O1—C16—O2	9.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.93	2.55	3.465 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.93	2.55	3.465 (4)	169

Symmetry code: (i) .