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

Li, J.-M.; Liang, D.

doi:10.1107/S1600536808035009

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2272

doi:10.1107/S1600536808035009

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

Jiu-Ming Li ^a ^* and Dong Liang ^b

^aCollege of Chemistry, Inner Mongolia University for Nationalities, Tongliao 028043, People's Republic of China, and ^bQingdao DIC Finechemicals Co. Ltd, Qingdao 266101, People's Republic of China
^*Correspondence e-mail: lijiuming10@yahoo.cn

(Received 22 October 2008; accepted 28 October 2008; online 8 November 2008)

In the title compound, C₁₆H₁₃NO₂, the two benzene rings make a dihedral angle of 55.5 (2)°. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds and weak π–π stacking interactions [centroid–centroid distance = 3.595 (3)Å], linking the molecules 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_r = 251.27
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.143
S = 1.13
2145 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) -x+1, -y, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Isoquinolinones are important compounds from both the synthetic and applied points of view. Their structures are incorporated in several alkaloids (Bentley, 20000 and other pharmacologically important compounds (Jayaraman et al., 2002). Of the variety of methods that have been developed for the synthesis of the isoquinoline ring system, the most commonly used procedure is the Bischler-Napieralski reaction (Bischler & Napieralski, 1893). We now wish to report an effective Bischler-Napieralski procedure for the synthesis of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-phenylisoquinoline the title compound (I) and report its crystal structure here.

In compound (I), all bond lengths in the molecular are normal (Allen et al., 1987). The benzene ring C10–C15 and bonded atoms C7, C9, O1 and O2 are coplanar, the largest deviation from the mean plane being 0.039 (2)Å for atom O1. The other benzene ring, C1–C6, and bonded atoms C7 are also coplanar, the largest deviation from the mean plane being 0.032 (2)Å. The two benzene rings make a dihedral angle of 55.5 (2)°.

The relatively short distance of 3.595 (3) between the centroids of benzene ring C10—C15 and 1,3-dioxole ring C13/C14/C16/O1/O2 [at -x,1 - y,-z] indicates the presence of weak π-π interactions, The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds, linking the molecules into ladders of dimers.

Related literature top

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 top

The title compound was synthesized by following Bischler-Napieralski procedures: 0.01 mol N-[2-(3, 4-methylenedioxy)phenyl]benzamide (synthesized by β-(3, 4-methylenedioxy)phenethylamine, Benzoyl chloride and Et₃N) was dissolved in 20 ml CH₃CN, 5 g POCl₃ was added dropwise, the mixture was refluxed under N₂ for 5 h, after cooled the volatiles were evaporated under vacuum, then water was added and adjusted the pH to 8, after extracted with CH₂Cl₂, the organic layers was washed with saturated NaCl and dried with Na₂SO₄, the product was isolated by evaporation of the solvent and recrystalization, 2.31 g, Yield: 92%. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

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

Crystal data top

C₁₆H₁₃NO₂	Z = 2
M_r = 251.27	F(000) = 264
Triclinic, P1	D_x = 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 = 2.5–23.4°
c = 10.143 (2) Å	µ = 0.09 mm⁻¹
α = 109.07 (3)°	T = 293 K
β = 109.44 (2)°	Block, colorless
γ = 99.70 (3)°	0.28 × 0.10 × 0.08 mm
V = 622.9 (2) Å³

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	2145 independent reflections
Radiation source: Rotating Anode	1275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω oscillation scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.976, T_max = 0.993	k = −10→10
4801 measured reflections	l = −11→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0514P)² + 0.1397P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
2145 reflections	Δρ_max = 0.20 e Å⁻³
173 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	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)

Crystal data top

C₁₆H₁₃NO₂	γ = 99.70 (3)°
M_r = 251.27	V = 622.9 (2) Å³
Triclinic, P1	Z = 2
a = 8.5005 (17) Å	Mo Kα radiation
b = 8.5297 (17) Å	µ = 0.09 mm⁻¹
c = 10.143 (2) Å	T = 293 K
α = 109.07 (3)°	0.28 × 0.10 × 0.08 mm
β = 109.44 (2)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	2145 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1275 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.993	R_int = 0.037
4801 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.13	Δρ_max = 0.20 e Å⁻³
2145 reflections	Δρ_min = −0.20 e Å⁻³
173 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₂
M_r	251.27
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5005 (17), 8.5297 (17), 10.143 (2)
α, β, γ (°)	109.07 (3), 109.44 (2), 99.70 (3)
V (Å³)	622.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.10 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.976, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	4801, 2145, 1275
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.144, 1.13
No. of reflections	2145
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.93	2.55	3.465 (4)	168.9

Symmetry code: (i) −x+1, −y, −z+1.

References

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Volume 64| Part 12| December 2008| Page o2272

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