2-Hy­droxy­iso­quinoline-1,3(2H,4H)-dione

Ishikawa, Y.; Matsuo, S.

doi:10.1107/S1600536813019843

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1312

doi:10.1107/S1600536813019843

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2-Hydroxyisoquinoline-1,3(2H,4H)-dione

Yoshinobu Ishikawa ^a ^* and Soichiro Matsuo ^a

^aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
^*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

(Received 21 June 2013; accepted 18 July 2013; online 24 July 2013)

The title molecule, C₉H₇NO₃, exists in the diketo form and the isoquinoline unit is approximately planar (r.m.s. deviation = 0.0158 Å). In the crystal, molecules are linked into inversion dimers through pairs of O—H⋯O hydrogen bonds and are further assembled into the (100) layers via stacking interactions [centroid–centroid distances = 3.460 (3) and 3.635 (4) Å].

Related literature

For the biological properties of the title compound, see: Parkes et al. (2003 ); Hang et al. (2004 ); Billamboz et al. (2008 ). For a related structure, see: Miao et al. (1995 ).

Experimental

Crystal data

C₉H₇NO₃
M_r = 177.16
Monoclinic, P 2₁ /n
a = 12.336 (5) Å
b = 8.666 (4) Å
c = 7.052 (7) Å
β = 104.19 (5)°
V = 730.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.50 × 0.50 × 0.45 mm

Data collection

Rigaku AFC-7R diffractometer
3873 measured reflections
1650 independent reflections
1484 reflections with F² > 2σ(F²)
R_int = 0.016
3 standard reflections every 150 reflections intensity decay: −0.5%

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.089
S = 1.04
1650 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1ⁱ	0.84	1.91	2.7056 (17)	158
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 $[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]$ ); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019843/gk2583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019843/gk2583Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019843/gk2583Isup3.cml

checkCIF report

Comment top

The title compound is known to inhibit metalloenzymes such as influenza endonuclease (Parkes et al., 2003), HIV-1 reverse transcriptase RNase H (Hang et al., 2004), and HIV-1 integrase (Billamboz et al., 2008). Here we report the crystal structure of the title compound, which was obtained from the deprotection of 2-benzyloxyisoquinoline-1,3(2H,4H)-dione by the use of boron tribromide. The compound exists in keto form and the isoquinoline ring is almost planar (r.m.s. deviation = 0.0158 Å). In the crystal, the molecules link through intermolecular O–H···O hydrogen bonds and stack along the c axis, as shown in Figure 2. The distance from plane1 (C7/C8/C9/C11/C12/C13) to plane2 [C4/C6/C7/C8/C10/N3, (1 - x, 2 - y, 1 - z)] is 3.460 (3) Å.

Related literature top

For the biological properties of the title compound, see: Parkes et al. (2003); Hang et al. (2004); Billamboz et al. (2008). For a related structures, see: Miao et al. (1995).

Experimental top

The title compound was synthesized according to the literature (Billamboz et al., 2008). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution of the compound at room temperature.

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
	Fig. 2. A crystal packing view of the title compound. Hydrogen bonds are represented as dashed lines.

2-Hydroxyisoquinoline-1,3(2H,4H)-dione top

Crystal data top

C₉H₇NO₃	F(000) = 368.00
M_r = 177.16	D_x = 1.610 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.336 (5) Å	θ = 14.9–17.0°
b = 8.666 (4) Å	µ = 0.12 mm⁻¹
c = 7.052 (7) Å	T = 100 K
β = 104.19 (5)°	Block, orange
V = 730.8 (9) Å³	0.50 × 0.50 × 0.45 mm
Z = 4

Data collection top

Rigaku AFC-7R diffractometer	θ_max = 27.5°
ω–2θ scans	h = −16→15
3873 measured reflections	k = −11→11
1650 independent reflections	l = −5→9
1484 reflections with F² > 2σ(F²)	3 standard reflections every 150 reflections
R_int = 0.016	intensity decay: −0.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0517P)² + 0.2377P] where P = (F_o² + 2F_c²)/3
1650 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₉H₇NO₃	V = 730.8 (9) Å³
M_r = 177.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.336 (5) Å	µ = 0.12 mm⁻¹
b = 8.666 (4) Å	T = 100 K
c = 7.052 (7) Å	0.50 × 0.50 × 0.45 mm
β = 104.19 (5)°

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.016
3873 measured reflections	3 standard reflections every 150 reflections
1650 independent reflections	intensity decay: −0.5%
1484 reflections with F² > 2σ(F²)

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
1650 reflections	Δρ_min = −0.25 e Å⁻³
119 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O1	0.41291 (6)	0.60097 (8)	0.84881 (11)	0.01900 (19)
O2	0.71902 (6)	0.89780 (9)	0.89569 (11)	0.01901 (19)
O5	0.63125 (6)	0.62843 (8)	0.92088 (12)	0.01860 (19)
N3	0.56130 (7)	0.75393 (9)	0.86013 (12)	0.0136 (2)
C4	0.37267 (8)	0.86193 (11)	0.74485 (15)	0.0132 (2)
C6	0.61776 (8)	0.89219 (11)	0.84438 (14)	0.0133 (2)
C7	0.54474 (8)	1.02389 (11)	0.76248 (13)	0.0124 (2)
C8	0.42836 (8)	1.01072 (11)	0.71477 (13)	0.0124 (2)
C9	0.59616 (8)	1.16334 (12)	0.73257 (14)	0.0149 (3)
C10	0.44805 (8)	0.72873 (11)	0.82056 (14)	0.0134 (2)
C11	0.53109 (9)	1.28959 (12)	0.65699 (15)	0.0164 (3)
C12	0.36371 (8)	1.13890 (12)	0.63746 (15)	0.0151 (3)
C13	0.41430 (9)	1.27737 (12)	0.60954 (15)	0.0165 (3)
H4A	0.3253	0.8813	0.8372	0.0158*
H4B	0.3224	0.8312	0.6184	0.0158*
H5	0.6004	0.5666	0.9829	0.0223*
H9	0.6754	1.1710	0.7641	0.0179*
H11	0.5655	1.3843	0.6373	0.0197*
H12	0.2845	1.1312	0.6037	0.0182*
H13	0.3696	1.3641	0.5581	0.0198*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0159 (4)	0.0140 (4)	0.0257 (4)	−0.0012 (3)	0.0025 (3)	0.0038 (3)
O2	0.0111 (4)	0.0193 (4)	0.0255 (4)	0.0003 (3)	0.0023 (3)	0.0022 (3)
O5	0.0134 (4)	0.0132 (4)	0.0283 (5)	0.0044 (3)	0.0034 (3)	0.0058 (3)
N3	0.0114 (4)	0.0112 (4)	0.0173 (4)	0.0027 (3)	0.0014 (3)	0.0018 (3)
C4	0.0104 (5)	0.0130 (5)	0.0158 (5)	0.0001 (4)	0.0028 (4)	0.0006 (4)
C6	0.0126 (5)	0.0142 (5)	0.0132 (5)	−0.0007 (4)	0.0032 (4)	−0.0011 (4)
C7	0.0133 (5)	0.0128 (5)	0.0112 (5)	0.0003 (4)	0.0030 (4)	−0.0012 (4)
C8	0.0132 (5)	0.0127 (5)	0.0116 (5)	0.0001 (4)	0.0039 (4)	−0.0012 (4)
C9	0.0140 (5)	0.0162 (5)	0.0146 (5)	−0.0028 (4)	0.0036 (4)	−0.0015 (4)
C10	0.0131 (5)	0.0144 (5)	0.0124 (5)	−0.0007 (4)	0.0027 (4)	−0.0011 (4)
C11	0.0198 (5)	0.0125 (5)	0.0176 (5)	−0.0029 (4)	0.0059 (4)	−0.0012 (4)
C12	0.0135 (5)	0.0154 (5)	0.0168 (5)	0.0019 (4)	0.0040 (4)	−0.0006 (4)
C13	0.0187 (5)	0.0129 (5)	0.0180 (5)	0.0030 (4)	0.0045 (4)	0.0004 (4)

Geometric parameters (Å, º) top

O1—C10	1.2230 (13)	C9—C11	1.3841 (15)
O2—C6	1.2133 (13)	C11—C13	1.4009 (17)
O5—N3	1.3891 (12)	C12—C13	1.3887 (16)
N3—C6	1.4039 (14)	O5—H5	0.840
N3—C10	1.3734 (14)	C4—H4A	0.990
C4—C8	1.5003 (15)	C4—H4B	0.990
C4—C10	1.4962 (15)	C9—H9	0.950
C6—C7	1.4807 (14)	C11—H11	0.950
C7—C8	1.3966 (15)	C12—H12	0.950
C7—C9	1.4046 (16)	C13—H13	0.950
C8—C12	1.3978 (15)

O5—N3—C6	114.20 (9)	C9—C11—C13	119.84 (10)
O5—N3—C10	117.53 (8)	C8—C12—C13	120.58 (10)
C6—N3—C10	128.27 (8)	C11—C13—C12	120.20 (10)
C8—C4—C10	116.58 (9)	N3—O5—H5	109.471
O2—C6—N3	120.34 (9)	C8—C4—H4A	108.149
O2—C6—C7	124.67 (10)	C8—C4—H4B	108.145
N3—C6—C7	114.99 (9)	C10—C4—H4A	108.149
C6—C7—C8	121.47 (9)	C10—C4—H4B	108.153
C6—C7—C9	117.89 (9)	H4A—C4—H4B	107.318
C8—C7—C9	120.63 (9)	C7—C9—H9	120.087
C4—C8—C7	121.03 (9)	C11—C9—H9	120.091
C4—C8—C12	120.06 (9)	C9—C11—H11	120.082
C7—C8—C12	118.92 (10)	C13—C11—H11	120.074
C7—C9—C11	119.82 (10)	C8—C12—H12	119.713
O1—C10—N3	119.63 (9)	C13—C12—H12	119.710
O1—C10—C4	122.85 (10)	C11—C13—H13	119.902
N3—C10—C4	117.52 (9)	C12—C13—H13	119.895

H5—O5—N3—C6	150.2	N3—C6—C7—C9	−176.51 (8)
H5—O5—N3—C10	−30.7	C6—C7—C8—C4	0.00 (14)
O5—N3—C6—O2	−5.29 (13)	C6—C7—C8—C12	−179.84 (8)
O5—N3—C6—C7	174.61 (7)	C6—C7—C9—C11	−179.76 (8)
O5—N3—C10—O1	3.59 (14)	C6—C7—C9—H9	0.2
O5—N3—C10—C4	−176.79 (8)	C8—C7—C9—C11	0.67 (14)
C6—N3—C10—O1	−177.53 (9)	C8—C7—C9—H9	−179.3
C6—N3—C10—C4	2.09 (15)	C9—C7—C8—C4	179.56 (8)
C10—N3—C6—O2	175.80 (9)	C9—C7—C8—C12	−0.28 (14)
C10—N3—C6—C7	−4.30 (15)	C4—C8—C12—C13	179.79 (9)
C8—C4—C10—O1	−179.05 (9)	C4—C8—C12—H12	−0.2
C8—C4—C10—N3	1.35 (13)	C7—C8—C12—C13	−0.36 (15)
C10—C4—C8—C7	−2.26 (14)	C7—C8—C12—H12	179.6
C10—C4—C8—C12	177.58 (8)	C7—C9—C11—C13	−0.41 (15)
H4A—C4—C8—C7	119.8	C7—C9—C11—H11	179.6
H4A—C4—C8—C12	−60.4	H9—C9—C11—C13	179.6
H4B—C4—C8—C7	−124.3	H9—C9—C11—H11	−0.4
H4B—C4—C8—C12	55.5	C9—C11—C13—C12	−0.23 (16)
H4A—C4—C10—O1	58.9	C9—C11—C13—H13	179.8
H4A—C4—C10—N3	−120.7	H11—C11—C13—C12	179.8
H4B—C4—C10—O1	−57.0	H11—C11—C13—H13	−0.2
H4B—C4—C10—N3	123.4	C8—C12—C13—C11	0.62 (16)
O2—C6—C7—C8	−177.04 (9)	C8—C12—C13—H13	−179.4
O2—C6—C7—C9	3.39 (15)	H12—C12—C13—C11	−179.4
N3—C6—C7—C8	3.06 (13)	H12—C12—C13—H13	0.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1ⁱ	0.84	1.91	2.7056 (17)	158

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1ⁱ	0.84	1.91	2.7056 (17)	158

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

The authors acknowledge the University of Shizuoka for supporting this study.

References

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