2-Hy-droxy-iso-quinoline-1,3(2H,4H)-dione.

The title mol-ecule, C9H7NO3, exists in the diketo form and the iso-quinoline unit is approximately planar (r.m.s. deviation = 0.0158 Å). In the crystal, mol-ecules are linked into inversion dimers through pairs of O-H⋯O hydrogen bonds and are further assembled into the (100) layers via stacking inter-actions [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 = 177.16

Monoclinic,

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 F 2 > 2σ(F 2)

R int = 0.016

3 standard reflections every 150 reflections intensity decay: −0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.04

1650 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019843/gk2583sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019843/gk2583Isup3.cml

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

C9H7NO3	F(000) = 368.00
Mr = 177.16	Dx = 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

Rigaku AFC-7R diffractometer	θmax = 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
Rint = 0.016	intensity decay: −0.5%

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(Fo2) + (0.0517P)2 + 0.2377P] where P = (Fo2 + 2Fc2)/3
1650 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods

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).

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .