Crystal structure of 2-(1,3-dioxoindan-2-yl)iso-quinoline-1,3,4-trione.

In the title iso-quinoline-1,3,4-trione derivative, C18H9NO5, the five-membered ring of the indane fragment adopts an envelope conformation with the nitro-gen-substituted C atom being the flap. The planes of the indane benzene ring and the iso-quinoline-1,3,4-trione ring make a dihedral angle of 82.06 (6)°. In the crystal, mol-ecules are linked into chains extending along the bc plane via C-H⋯O hydrogen-bonding inter-actions, enclosing R 2 (2)(8) and R 2 (2)(10) loops. The chains are further connected by π-π stacking inter-ations, with centroid-to-centroid distances of 3.9050 (7) Å, forming layers parallel to the b axis.

Related literature

For the biological activity of iso­quinoline-1,3,4-triones, see: Chen et al. (2006 ▸); Du et al. (2008 ▸). For related iso­quinoline-1,3,4-trione structures, see: Yu et al. (2010 ▸); Huang et al. (2013 ▸). For synthetic applications of iso­quinoline-1,3,4-trione, see: Yu et al. (2010 ▸); Huang et al. (2011 ▸, 2013 ▸). For the synthesis of related compounds, see: Chen et al. (2006 ▸); Du et al. (2008 ▸); Ghalib et al. 2011 ▸; Schaber et al. 2004 ▸; Huang et al. (2013 ▸).

Experimental

Crystal data

C18H9NO5

M = 319.26

Monoclinic,

a = 12.6080 (1) Å

b = 13.6849 (2) Å

c = 8.4467 (1) Å

β = 102.051 (1)°

V = 1425.27 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.93 mm−1

T = 100 K

0.24 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.808, T max = 0.879

9639 measured reflections

2597 independent reflections

2458 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.04

2597 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014025997/zl2607sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025997/zl2607Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014025997/zl2607Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014025997/zl2607fig1.tif

The mol­ecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.

Click here for additional data file.

A A x y z . DOI: 10.1107/S2056989014025997/zl2607fig2.tif

Crystal packing of the title compound, showing the C6–H6A⋯O2 and C7–H7A⋯O1 hydrogen bonding inter­actions (Symmetry codes: x, y, z + 1) as dashed lines incorporating (8) loops. Other H-atoms are omited for clarity.

Click here for additional data file.

x y z x y z x y z . DOI: 10.1107/S2056989014025997/zl2607fig3.tif

Crystal packing of the title compound, showing the C–H⋯O hydrogen bonding inter­actions (Symmetry codes: x, −y + , z − ; −x, y + , −z − ; −x, y − , −z − ) as dashed lines incorporating (10) loops. Other H-atoms are omited for clarity.

Click here for additional data file.

. DOI: 10.1107/S2056989014025997/zl2607fig4.tif

Reaction scheme for the title compound.

CCDC reference: 1036387

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H9NO5	F(000) = 656
Mr = 319.26	Dx = 1.488 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 12.6080 (1) Å	Cell parameters from 6347 reflections
b = 13.6849 (2) Å	θ = 6.3–71.7°
c = 8.4467 (1) Å	µ = 0.93 mm−1
β = 102.051 (1)°	T = 100 K
V = 1425.27 (3) Å3	Block, orange
Z = 4	0.24 × 0.15 × 0.14 mm

Bruker APEXII CCD diffractometer	2458 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
φ and ω scans	θmax = 72.0°, θmin = 6.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→14
Tmin = 0.808, Tmax = 0.879	k = −16→16
9639 measured reflections	l = −9→8
2597 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.5485P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2597 reflections	Δρmax = 0.27 e Å−3
217 parameters	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.36681 (7)	0.34686 (7)	−0.36897 (11)	0.0226 (2)
O2	0.56844 (7)	0.37737 (7)	−0.18918 (11)	0.0244 (2)
O3	0.22076 (7)	0.37449 (6)	0.07501 (11)	0.0212 (2)
O4	0.14773 (7)	0.52030 (7)	−0.25876 (13)	0.0310 (3)
O5	0.14677 (7)	0.18880 (6)	−0.12358 (10)	0.0208 (2)
N1	0.29330 (8)	0.35524 (7)	−0.14517 (12)	0.0167 (2)
C1	0.37928 (9)	0.35678 (8)	−0.22453 (15)	0.0171 (3)
C2	0.49378 (10)	0.37240 (8)	−0.11979 (15)	0.0182 (3)
C3	0.50578 (10)	0.38012 (8)	0.05673 (15)	0.0173 (3)
C4	0.60836 (10)	0.39054 (9)	0.15659 (16)	0.0202 (3)
H4A	0.6710	0.3933	0.1108	0.024*
C5	0.61838 (10)	0.39680 (9)	0.32253 (16)	0.0219 (3)
H5A	0.6880	0.4043	0.3907	0.026*
C6	0.52631 (10)	0.39207 (9)	0.39026 (16)	0.0213 (3)
H6A	0.5339	0.3947	0.5045	0.026*
C7	0.42389 (10)	0.38360 (8)	0.29149 (15)	0.0191 (3)
H7A	0.3614	0.3817	0.3377	0.023*
C8	0.41329 (10)	0.37786 (8)	0.12429 (15)	0.0172 (3)
C9	0.30286 (10)	0.36955 (8)	0.02176 (15)	0.0172 (3)
C10	0.18389 (9)	0.34521 (9)	−0.24087 (15)	0.0180 (3)
H10A	0.1894	0.3278	−0.3539	0.022*
C11	0.11456 (10)	0.43817 (9)	−0.24898 (16)	0.0210 (3)
C12	0.00327 (10)	0.40620 (9)	−0.24322 (16)	0.0215 (3)
C13	−0.09105 (10)	0.46146 (10)	−0.26425 (18)	0.0276 (3)
H13A	−0.0910	0.5291	−0.2893	0.033*
C14	−0.18531 (11)	0.41422 (10)	−0.2473 (2)	0.0314 (3)
H14A	−0.2510	0.4502	−0.2610	0.038*
C15	−0.18544 (11)	0.31468 (10)	−0.21033 (19)	0.0315 (3)
H15A	−0.2513	0.2842	−0.2000	0.038*
C16	−0.09097 (11)	0.25943 (10)	−0.18845 (18)	0.0267 (3)
H16A	−0.0910	0.1918	−0.1629	0.032*
C17	0.00336 (10)	0.30685 (9)	−0.20540 (15)	0.0201 (3)
C18	0.11462 (9)	0.26700 (8)	−0.18079 (14)	0.0173 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0203 (4)	0.0298 (5)	0.0183 (5)	−0.0022 (3)	0.0056 (3)	−0.0011 (4)
O2	0.0176 (4)	0.0350 (5)	0.0221 (5)	−0.0004 (3)	0.0075 (4)	0.0005 (4)
O3	0.0169 (4)	0.0267 (5)	0.0214 (5)	−0.0016 (3)	0.0072 (3)	−0.0031 (3)
O4	0.0215 (5)	0.0205 (5)	0.0501 (7)	−0.0025 (4)	0.0055 (4)	0.0081 (4)
O5	0.0218 (4)	0.0175 (4)	0.0219 (5)	0.0011 (3)	0.0019 (3)	−0.0010 (3)
N1	0.0137 (5)	0.0192 (5)	0.0172 (5)	−0.0005 (4)	0.0031 (4)	−0.0007 (4)
C1	0.0180 (6)	0.0152 (6)	0.0189 (7)	0.0001 (4)	0.0055 (5)	0.0008 (4)
C2	0.0169 (6)	0.0160 (6)	0.0222 (7)	0.0003 (4)	0.0055 (5)	0.0006 (5)
C3	0.0180 (6)	0.0149 (5)	0.0190 (6)	0.0000 (4)	0.0043 (5)	0.0012 (4)
C4	0.0180 (6)	0.0196 (6)	0.0234 (7)	−0.0004 (4)	0.0054 (5)	0.0014 (5)
C5	0.0185 (6)	0.0224 (6)	0.0226 (7)	−0.0017 (5)	−0.0004 (5)	0.0007 (5)
C6	0.0250 (6)	0.0207 (6)	0.0180 (6)	−0.0017 (5)	0.0036 (5)	−0.0004 (5)
C7	0.0206 (6)	0.0178 (6)	0.0202 (6)	−0.0010 (4)	0.0069 (5)	−0.0003 (4)
C8	0.0181 (6)	0.0138 (5)	0.0198 (6)	−0.0005 (4)	0.0039 (5)	0.0002 (4)
C9	0.0180 (6)	0.0146 (5)	0.0198 (6)	−0.0006 (4)	0.0060 (5)	−0.0006 (4)
C10	0.0157 (6)	0.0203 (6)	0.0174 (6)	−0.0002 (4)	0.0024 (4)	0.0001 (4)
C11	0.0177 (6)	0.0207 (6)	0.0237 (7)	−0.0003 (5)	0.0022 (5)	0.0039 (5)
C12	0.0178 (6)	0.0202 (6)	0.0257 (7)	−0.0012 (5)	0.0031 (5)	0.0000 (5)
C13	0.0203 (6)	0.0192 (6)	0.0423 (8)	0.0017 (5)	0.0042 (5)	0.0014 (6)
C14	0.0177 (6)	0.0261 (7)	0.0497 (9)	0.0029 (5)	0.0058 (6)	−0.0034 (6)
C15	0.0188 (6)	0.0264 (7)	0.0508 (9)	−0.0049 (5)	0.0107 (6)	−0.0036 (6)
C16	0.0222 (6)	0.0189 (6)	0.0398 (8)	−0.0028 (5)	0.0083 (5)	−0.0010 (5)
C17	0.0183 (6)	0.0195 (6)	0.0225 (7)	−0.0007 (5)	0.0039 (5)	−0.0019 (5)
C18	0.0177 (6)	0.0180 (6)	0.0157 (6)	−0.0019 (4)	0.0025 (4)	−0.0035 (4)

O1—C1	1.2048 (15)	C7—C8	1.3927 (18)
O2—C2	1.2102 (15)	C7—H7A	0.9500
O3—C9	1.2136 (15)	C8—C9	1.4825 (17)
O4—C11	1.2080 (16)	C10—C18	1.5332 (16)
O5—C18	1.2088 (15)	C10—C11	1.5370 (16)
N1—C1	1.3886 (15)	C10—H10A	1.0000
N1—C9	1.4036 (16)	C11—C12	1.4802 (17)
N1—C10	1.4525 (15)	C12—C13	1.3890 (18)
C1—C2	1.5424 (16)	C12—C17	1.3966 (17)
C2—C3	1.4707 (17)	C13—C14	1.3863 (19)
C3—C4	1.3961 (17)	C13—H13A	0.9500
C3—C8	1.4016 (17)	C14—C15	1.398 (2)
C4—C5	1.3835 (18)	C14—H14A	0.9500
C4—H4A	0.9500	C15—C16	1.3901 (19)
C5—C6	1.3987 (18)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.3883 (18)
C6—C7	1.3881 (18)	C16—H16A	0.9500
C6—H6A	0.9500	C17—C18	1.4787 (16)
C1—N1—C9	124.81 (10)	N1—C10—C18	114.97 (10)
C1—N1—C10	118.64 (10)	N1—C10—C11	114.32 (10)
C9—N1—C10	116.40 (10)	C18—C10—C11	103.57 (9)
O1—C1—N1	122.48 (11)	N1—C10—H10A	107.9
O1—C1—C2	120.34 (11)	C18—C10—H10A	107.9
N1—C1—C2	117.17 (10)	C11—C10—H10A	107.9
O2—C2—C3	124.14 (11)	O4—C11—C12	128.41 (12)
O2—C2—C1	117.35 (11)	O4—C11—C10	124.84 (11)
C3—C2—C1	118.51 (10)	C12—C11—C10	106.74 (10)
C4—C3—C8	120.06 (11)	C13—C12—C17	121.27 (12)
C4—C3—C2	120.40 (11)	C13—C12—C11	128.83 (12)
C8—C3—C2	119.54 (11)	C17—C12—C11	109.86 (11)
C5—C4—C3	119.71 (11)	C14—C13—C12	117.55 (12)
C5—C4—H4A	120.1	C14—C13—H13A	121.2
C3—C4—H4A	120.1	C12—C13—H13A	121.2
C4—C5—C6	120.23 (11)	C13—C14—C15	121.24 (12)
C4—C5—H5A	119.9	C13—C14—H14A	119.4
C6—C5—H5A	119.9	C15—C14—H14A	119.4
C7—C6—C5	120.36 (12)	C16—C15—C14	121.26 (12)
C7—C6—H6A	119.8	C16—C15—H15A	119.4
C5—C6—H6A	119.8	C14—C15—H15A	119.4
C6—C7—C8	119.63 (11)	C17—C16—C15	117.44 (12)
C6—C7—H7A	120.2	C17—C16—H16A	121.3
C8—C7—H7A	120.2	C15—C16—H16A	121.3
C7—C8—C3	119.98 (11)	C16—C17—C12	121.25 (11)
C7—C8—C9	118.45 (11)	C16—C17—C18	128.40 (11)
C3—C8—C9	121.57 (11)	C12—C17—C18	110.28 (10)
O3—C9—N1	118.63 (11)	O5—C18—C17	127.71 (11)
O3—C9—C8	123.28 (11)	O5—C18—C10	125.71 (11)
N1—C9—C8	118.09 (10)	C17—C18—C10	106.57 (10)
C9—N1—C1—O1	−177.84 (11)	C1—N1—C10—C18	131.20 (11)
C10—N1—C1—O1	−2.54 (16)	C9—N1—C10—C18	−53.10 (13)
C9—N1—C1—C2	1.89 (16)	C1—N1—C10—C11	−109.16 (12)
C10—N1—C1—C2	177.19 (9)	C9—N1—C10—C11	66.53 (13)
O1—C1—C2—O2	2.38 (17)	N1—C10—C11—O4	38.25 (18)
N1—C1—C2—O2	−177.36 (10)	C18—C10—C11—O4	164.10 (13)
O1—C1—C2—C3	−177.50 (11)	N1—C10—C11—C12	−142.00 (11)
N1—C1—C2—C3	2.76 (15)	C18—C10—C11—C12	−16.15 (13)
O2—C2—C3—C4	−2.32 (18)	O4—C11—C12—C13	7.3 (2)
C1—C2—C3—C4	177.55 (10)	C10—C11—C12—C13	−172.42 (13)
O2—C2—C3—C8	177.08 (11)	O4—C11—C12—C17	−170.35 (14)
C1—C2—C3—C8	−3.05 (16)	C10—C11—C12—C17	9.92 (14)
C8—C3—C4—C5	1.19 (17)	C17—C12—C13—C14	−0.4 (2)
C2—C3—C4—C5	−179.41 (11)	C11—C12—C13—C14	−177.81 (14)
C3—C4—C5—C6	0.42 (18)	C12—C13—C14—C15	0.0 (2)
C4—C5—C6—C7	−1.67 (19)	C13—C14—C15—C16	0.3 (2)
C5—C6—C7—C8	1.27 (18)	C14—C15—C16—C17	−0.3 (2)
C6—C7—C8—C3	0.35 (17)	C15—C16—C17—C12	−0.1 (2)
C6—C7—C8—C9	−179.58 (10)	C15—C16—C17—C18	176.66 (13)
C4—C3—C8—C7	−1.59 (17)	C13—C12—C17—C16	0.4 (2)
C2—C3—C8—C7	179.01 (10)	C11—C12—C17—C16	178.31 (12)
C4—C3—C8—C9	178.35 (10)	C13—C12—C17—C18	−176.86 (12)
C2—C3—C8—C9	−1.06 (16)	C11—C12—C17—C18	1.01 (15)
C1—N1—C9—O3	174.03 (10)	C16—C17—C18—O5	−9.2 (2)
C10—N1—C9—O3	−1.36 (15)	C12—C17—C18—O5	167.87 (12)
C1—N1—C9—C8	−5.98 (16)	C16—C17—C18—C10	171.40 (13)
C10—N1—C9—C8	178.63 (10)	C12—C17—C18—C10	−11.55 (14)
C7—C8—C9—O3	5.45 (17)	N1—C10—C18—O5	−37.31 (17)
C3—C8—C9—O3	−174.48 (11)	C11—C10—C18—O5	−162.74 (12)
C7—C8—C9—N1	−174.54 (10)	N1—C10—C18—C17	142.12 (10)
C3—C8—C9—N1	5.52 (16)	C11—C10—C18—C17	16.70 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2i	0.95	2.54	3.4862 (16)	171
C7—H7A···O1i	0.95	2.51	3.1397 (15)	124
C10—H10A···O5ii	1.00	2.24	3.2022 (15)	161
C13—H13A···O5iii	0.95	2.37	3.2852 (16)	163
C16—H16A···O4iv	0.95	2.50	3.3596 (17)	150

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6AO2i	0.95	2.54	3.4862(16)	171
C7H7AO1i	0.95	2.51	3.1397(15)	124
C10H10AO5ii	1.00	2.24	3.2022(15)	161
C13H13AO5iii	0.95	2.37	3.2852(16)	163
C16H16AO4iv	0.95	2.50	3.3596(17)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .