Imidazo[1,2-b]isoquinoline-5,10-dione

Al-Mohammed, N.N.; Alias, Y.; Abdullah, Z.; Khaledi, H.

doi:10.1107/S1600536811022082

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1666

doi:10.1107/S1600536811022082

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Imidazo[1,2-b]isoquinoline-5,10-dione

Nassir N. Al-Mohammed,^a ‡ Yatimah Alias,^a Zanariah Abdullah ^a and Hamid Khaledi ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 22 May 2011; accepted 7 June 2011; online 18 June 2011)

The title butterfly-shaped molecule, C₁₁H₆N₂O₂, is folded slightly along the O=C⋯C=O line, the dihedral angle between the two parts being 6.42 (3)°. In the crystal, adjacent molecules are linked through C—H⋯O hydrogen bonds into infinite layers parallel to the ac plane. The layers are further connected into a three-dimensional netweork via π–π interactions formed between pairs of antiparallel arranged molecules, with a centroid–centroid distance between the central six-membered ring and the benzene ring of 3.4349 (9) Å.

Related literature

For the structure of isoquinolinedione-pyrrole fused system in 1,3-dinitropyrrolo[1,2-b]isoquinoline-5,10-dione, see: Du & Hitchcock (1992 ).

Experimental

Crystal data

C₁₁H₆N₂O₂
M_r = 198.18
Monoclinic, P 2₁ /c
a = 7.6518 (7) Å
b = 7.2469 (6) Å
c = 15.5197 (13) Å
β = 99.947 (1)°
V = 847.66 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.21 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.977, T_max = 0.990
4894 measured reflections
1925 independent reflections
1583 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.04
1925 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.46	3.2828 (17)	146
C6—H6⋯O1ⁱⁱ	0.95	2.57	3.5190 (19)	179
C8—H8⋯O2ⁱⁱⁱ	0.95	2.55	3.2233 (17)	128
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536811022082/gk2380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022082/gk2380Isup2.hkl

checkCIF report

Comment top

This work reports the first crystal structure of an isoquinolinedione-fused imidazole. The structure of an isoquinolinedione-pyrrole fused system has been reported previously (Du & Hitchcock, 1992). The present molecule (Fig. 1) is almost planar (r.m.s deviation = 0.0718 Å) but slighly bent along the O=C···.C=O line with the corresponding dihedral angle of 6.42 (3)°. In the crystal, intermolecular C—H···O interactions (Table 1) connect the molecules into a two-dimensional array in the ac plane (Fig. 2). The isoquinoline rings of pairs of the molecule related by symmetry –x + 1, -y + 1, -z, are placed above each other in an anti-parallel manner with the centriods of the six-membered heterocyclic ring and the benzene ring at a distance of 3.4349 (9) Å.

Related literature top

For the structure of isoquinolinedione-pyrrole fused system in 1,3-dinitropyrrolo[1,2-b]isoquinoline-5,10-dione, see: Du & Hitchcock (1992).

Experimental top

A solution of phthaloyl chloride (5.58 g, 27.5 mmol) in dry pyridine (20 ml) was added dropwise to a mixture of imidazole (1.7 g, 25 mmol) and bis (triphenylphosphine)palladium (II) chloride (0.87 g) in dry pyridine (15 ml) at 273 K. The mixture was refluxed for 4 h, then cooled to room temperature and poured into ice water (150 ml). The aqueous solution was extracted with chloroform and the chloroform solution was washed with 2 % aqueous HCl solution and distilled water (3 x15 ml). It was dried over magnesium sulfate and evaporated under vacuum. The amorphous residue was re-crystallized from acetonitrile to give yellow crystals of the title compound (m.p. = 232-234° C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The 2D-network formed by C—H···O hydrogen bonds.

Imidazo[1,2-b]isoquinoline-5,10-dione top

Crystal data top

C₁₁H₆N₂O₂	F(000) = 408
M_r = 198.18	D_x = 1.553 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1521 reflections
a = 7.6518 (7) Å	θ = 2.7–29.5°
b = 7.2469 (6) Å	µ = 0.11 mm⁻¹
c = 15.5197 (13) Å	T = 100 K
β = 99.947 (1)°	Block, yellow
V = 847.66 (13) Å³	0.21 × 0.17 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1925 independent reflections
Radiation source: fine-focus sealed tube	1583 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.977, T_max = 0.990	k = −9→8
4894 measured reflections	l = −20→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0535P)² + 0.3219P] where P = (F_o² + 2F_c²)/3
1925 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₁H₆N₂O₂	V = 847.66 (13) Å³
M_r = 198.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6518 (7) Å	µ = 0.11 mm⁻¹
b = 7.2469 (6) Å	T = 100 K
c = 15.5197 (13) Å	0.21 × 0.17 × 0.09 mm
β = 99.947 (1)°

Data collection top

Bruker APEXII CCD diffractometer	1925 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1583 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.990	R_int = 0.021
4894 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
1925 reflections	Δρ_min = −0.22 e Å⁻³
136 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	0.26338 (13)	0.48928 (15)	0.19588 (7)	0.0219 (3)
O2	0.82600 (13)	0.21685 (15)	0.07219 (7)	0.0224 (3)
N1	0.62688 (16)	0.52159 (17)	0.28827 (8)	0.0186 (3)
N2	0.70971 (15)	0.36883 (16)	0.17748 (7)	0.0152 (3)
C1	0.80899 (19)	0.5005 (2)	0.30252 (10)	0.0202 (3)
H1	0.8866	0.5453	0.3526	0.024*
C2	0.86301 (19)	0.4074 (2)	0.23580 (9)	0.0197 (3)
H2	0.9811	0.3757	0.2304	0.024*
C3	0.69589 (18)	0.28089 (19)	0.09539 (9)	0.0160 (3)
C4	0.51463 (18)	0.27899 (19)	0.04292 (9)	0.0154 (3)
C5	0.4917 (2)	0.20479 (19)	−0.04108 (9)	0.0190 (3)
H5	0.5907	0.1567	−0.0632	0.023*
C6	0.3242 (2)	0.2012 (2)	−0.09248 (10)	0.0222 (3)
H6	0.3089	0.1516	−0.1500	0.027*
C7	0.1790 (2)	0.2701 (2)	−0.06005 (9)	0.0217 (3)
H7	0.0644	0.2665	−0.0953	0.026*
C8	0.20076 (18)	0.3441 (2)	0.02357 (9)	0.0186 (3)
H8	0.1011	0.3913	0.0454	0.022*
C9	0.36831 (18)	0.34932 (19)	0.07565 (9)	0.0150 (3)
C10	0.38834 (18)	0.43063 (19)	0.16455 (9)	0.0155 (3)
C11	0.57142 (18)	0.44126 (19)	0.21262 (9)	0.0151 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0171 (5)	0.0277 (6)	0.0215 (5)	0.0024 (4)	0.0055 (4)	−0.0027 (4)
O2	0.0182 (5)	0.0241 (6)	0.0262 (6)	0.0027 (4)	0.0073 (4)	−0.0027 (5)
N1	0.0194 (6)	0.0195 (6)	0.0161 (6)	−0.0011 (5)	0.0012 (5)	−0.0007 (5)
N2	0.0137 (6)	0.0157 (6)	0.0160 (6)	−0.0003 (4)	0.0022 (4)	0.0007 (5)
C1	0.0191 (7)	0.0209 (7)	0.0189 (7)	−0.0032 (6)	−0.0013 (5)	−0.0004 (6)
C2	0.0145 (7)	0.0201 (7)	0.0229 (7)	−0.0012 (6)	−0.0006 (5)	0.0029 (6)
C3	0.0179 (7)	0.0131 (6)	0.0175 (7)	−0.0002 (5)	0.0044 (5)	0.0017 (5)
C4	0.0185 (7)	0.0120 (6)	0.0156 (7)	−0.0010 (5)	0.0027 (5)	0.0027 (5)
C5	0.0265 (8)	0.0150 (7)	0.0165 (7)	−0.0012 (6)	0.0064 (6)	0.0012 (6)
C6	0.0343 (9)	0.0166 (7)	0.0147 (7)	−0.0056 (6)	0.0015 (6)	0.0003 (5)
C7	0.0226 (7)	0.0215 (8)	0.0186 (7)	−0.0052 (6)	−0.0037 (6)	0.0032 (6)
C8	0.0163 (7)	0.0195 (7)	0.0194 (7)	−0.0017 (6)	0.0017 (5)	0.0029 (6)
C9	0.0169 (7)	0.0134 (7)	0.0146 (7)	−0.0018 (5)	0.0024 (5)	0.0032 (5)
C10	0.0159 (7)	0.0146 (7)	0.0163 (7)	−0.0007 (5)	0.0038 (5)	0.0021 (5)
C11	0.0155 (7)	0.0143 (7)	0.0160 (7)	0.0003 (5)	0.0043 (5)	0.0019 (5)

Geometric parameters (Å, º) top

O1—C10	1.2215 (16)	C4—C9	1.4027 (19)
O2—C3	1.2084 (17)	C5—C6	1.388 (2)
N1—C11	1.3135 (18)	C5—H5	0.9500
N1—C1	1.3812 (19)	C6—C7	1.390 (2)
N2—C11	1.3754 (17)	C6—H6	0.9500
N2—C2	1.3808 (18)	C7—C8	1.387 (2)
N2—C3	1.4121 (18)	C7—H7	0.9500
C1—C2	1.359 (2)	C8—C9	1.3930 (19)
C1—H1	0.9500	C8—H8	0.9500
C2—H2	0.9500	C9—C10	1.4836 (19)
C3—C4	1.4821 (19)	C10—C11	1.4710 (18)
C4—C5	1.3930 (19)

C11—N1—C1	104.80 (12)	C5—C6—C7	120.15 (14)
C11—N2—C2	106.70 (12)	C5—C6—H6	119.9
C11—N2—C3	125.95 (12)	C7—C6—H6	119.9
C2—N2—C3	127.27 (12)	C8—C7—C6	120.21 (14)
C2—C1—N1	111.36 (13)	C8—C7—H7	119.9
C2—C1—H1	124.3	C6—C7—H7	119.9
N1—C1—H1	124.3	C7—C8—C9	120.21 (13)
C1—C2—N2	105.33 (13)	C7—C8—H8	119.9
C1—C2—H2	127.3	C9—C8—H8	119.9
N2—C2—H2	127.3	C8—C9—C4	119.48 (13)
O2—C3—N2	120.33 (13)	C8—C9—C10	119.16 (12)
O2—C3—C4	125.01 (13)	C4—C9—C10	121.35 (12)
N2—C3—C4	114.65 (12)	O1—C10—C11	121.49 (13)
C5—C4—C9	120.00 (13)	O1—C10—C9	123.10 (13)
C5—C4—C3	118.17 (12)	C11—C10—C9	115.39 (12)
C9—C4—C3	121.83 (12)	N1—C11—N2	111.81 (12)
C6—C5—C4	119.95 (13)	N1—C11—C10	127.51 (12)
C6—C5—H5	120.0	N2—C11—C10	120.63 (12)
C4—C5—H5	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.46	3.2828 (17)	146
C6—H6···O1ⁱⁱ	0.95	2.57	3.5190 (19)	179
C8—H8···O2ⁱⁱⁱ	0.95	2.55	3.2233 (17)	128

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₆N₂O₂
M_r	198.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.6518 (7), 7.2469 (6), 15.5197 (13)
β (°)	99.947 (1)
V (Å³)	847.66 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.21 × 0.17 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	4894, 1925, 1583
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.04
No. of reflections	1925
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.46	3.2828 (17)	146
C6—H6···O1ⁱⁱ	0.95	2.57	3.5190 (19)	179
C8—H8···O2ⁱⁱⁱ	0.95	2.55	3.2233 (17)	128

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: m_nassir1971@yahoo.com.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP001/2010 A).

References

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