2-(2-Meth-oxy-phen-yl)-1H-isoindole-1,3(2H)-dione.

In the title compound, C(15)H(11)NO(3), the dihedral angle between the meth-oxy-benzene and isoindole ring systems is 70.21 (3)°. The meth-oxy C atom is close to being coplanar with its attached ring [deviation = 0.133 (2) Å] and is oriented away from the isoindole moiety. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(10) loops. Further C-H⋯O inter-actions lead to (010) infinite sheets and weak aromatic π-π stacking [centroid-centroid separations = 3.6990 (10) and 3.7217 (10) Å] is also observed.

Related literature

For related structures, see: Sim et al. (2009 ▶); Sirajuddin et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al., 1995) ▶.

Experimental

Crystal data

C15H11NO3

M = 253.25

Orthorhombic,

a = 11.5768 (6) Å

b = 7.3222 (5) Å

c = 29.2849 (15) Å

V = 2482.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.32 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.969, T max = 0.977

10815 measured reflections

2428 independent reflections

1816 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.03

2428 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027262/hb6857sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027262/hb6857Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027262/hb6857Isup3.cml

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

C15H11NO3	F(000) = 1056
Mr = 253.25	Dx = 1.355 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1816 reflections
a = 11.5768 (6) Å	θ = 2.2–26.0°
b = 7.3222 (5) Å	µ = 0.10 mm−1
c = 29.2849 (15) Å	T = 296 K
V = 2482.4 (2) Å3	Prism, dark yellow
Z = 8	0.32 × 0.26 × 0.24 mm

Bruker Kappa APEXII CCD diffractometer	2428 independent reflections
Radiation source: fine-focus sealed tube	1816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.2°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→5
Tmin = 0.969, Tmax = 0.977	l = −35→36
10815 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.6208P] where P = (Fo2 + 2Fc2)/3
2428 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
O1	0.45483 (10)	0.37357 (19)	0.07121 (4)	0.0609 (4)
O2	0.74031 (12)	0.1478 (2)	0.16275 (4)	0.0672 (5)
O3	0.41409 (11)	−0.01341 (19)	0.11923 (4)	0.0632 (5)
N1	0.57642 (11)	0.2519 (2)	0.12589 (4)	0.0451 (4)
C1	0.54983 (14)	0.3245 (2)	0.08300 (5)	0.0432 (5)
C2	0.66018 (14)	0.3329 (2)	0.05763 (5)	0.0409 (5)
C3	0.68405 (17)	0.3932 (2)	0.01415 (6)	0.0512 (6)
C4	0.79860 (18)	0.3945 (3)	0.00060 (6)	0.0607 (6)
C5	0.88538 (17)	0.3416 (3)	0.02983 (7)	0.0635 (7)
C6	0.86140 (15)	0.2806 (2)	0.07348 (7)	0.0551 (6)
C7	0.74722 (14)	0.2752 (2)	0.08649 (5)	0.0422 (5)
C8	0.69509 (14)	0.2162 (2)	0.13013 (5)	0.0454 (5)
C9	0.49518 (15)	0.2254 (3)	0.16170 (5)	0.0501 (5)
C10	0.41319 (15)	0.0874 (3)	0.15822 (6)	0.0530 (6)
C11	0.33615 (18)	0.0624 (3)	0.19381 (7)	0.0716 (8)
C12	0.3427 (2)	0.1736 (4)	0.23180 (7)	0.0881 (9)
C13	0.4240 (2)	0.3075 (4)	0.23528 (7)	0.0922 (10)
C14	0.5005 (2)	0.3346 (3)	0.19983 (6)	0.0724 (8)
C15	0.3388 (2)	−0.1661 (3)	0.11653 (9)	0.0873 (10)
H3	0.62552	0.43151	−0.00537	0.0615*
H4	0.81725	0.43190	−0.02884	0.0728*
H5	0.96171	0.34706	0.02003	0.0762*
H6	0.92002	0.24465	0.09325	0.0661*
H11	0.28034	−0.02875	0.19216	0.0860*
H12	0.29047	0.15681	0.25555	0.1058*
H13	0.42784	0.37989	0.26133	0.1107*
H14	0.55562	0.42669	0.20171	0.0869*
H15A	0.35417	−0.24768	0.14146	0.1309*
H15B	0.35107	−0.22876	0.08815	0.1309*
H15C	0.26011	−0.12507	0.11816	0.1309*

	U11	U22	U33	U12	U13	U23
O1	0.0466 (7)	0.0825 (9)	0.0537 (7)	0.0051 (6)	−0.0098 (6)	0.0129 (6)
O2	0.0672 (8)	0.0852 (10)	0.0493 (7)	0.0108 (7)	−0.0175 (6)	0.0115 (7)
O3	0.0594 (8)	0.0663 (8)	0.0640 (8)	−0.0159 (7)	0.0127 (6)	−0.0053 (7)
N1	0.0446 (7)	0.0554 (8)	0.0354 (7)	−0.0026 (6)	−0.0048 (6)	0.0049 (6)
C1	0.0469 (9)	0.0450 (9)	0.0377 (8)	−0.0029 (7)	−0.0084 (7)	0.0011 (7)
C2	0.0486 (9)	0.0354 (8)	0.0386 (8)	−0.0039 (7)	−0.0041 (7)	−0.0020 (7)
C3	0.0687 (11)	0.0425 (9)	0.0424 (9)	−0.0034 (8)	−0.0003 (8)	0.0020 (7)
C4	0.0791 (13)	0.0484 (10)	0.0546 (10)	−0.0081 (10)	0.0193 (10)	0.0008 (9)
C5	0.0580 (11)	0.0530 (11)	0.0794 (14)	−0.0071 (9)	0.0204 (10)	−0.0039 (10)
C6	0.0472 (10)	0.0479 (10)	0.0701 (12)	−0.0016 (8)	−0.0024 (9)	−0.0064 (9)
C7	0.0466 (9)	0.0350 (8)	0.0451 (9)	−0.0031 (7)	−0.0037 (7)	−0.0049 (7)
C8	0.0497 (9)	0.0450 (9)	0.0414 (9)	−0.0003 (7)	−0.0116 (7)	−0.0016 (7)
C9	0.0507 (9)	0.0640 (11)	0.0356 (8)	0.0064 (9)	−0.0014 (7)	0.0044 (8)
C10	0.0499 (10)	0.0628 (11)	0.0464 (9)	0.0077 (9)	0.0064 (8)	0.0125 (9)
C11	0.0632 (12)	0.0882 (16)	0.0635 (12)	0.0137 (11)	0.0195 (10)	0.0266 (12)
C12	0.0832 (16)	0.131 (2)	0.0502 (12)	0.0392 (16)	0.0234 (12)	0.0282 (14)
C13	0.1046 (19)	0.131 (2)	0.0410 (11)	0.0330 (18)	0.0029 (12)	−0.0085 (13)
C14	0.0815 (14)	0.0915 (16)	0.0442 (10)	0.0069 (12)	−0.0051 (10)	−0.0098 (10)
C15	0.0696 (14)	0.0819 (16)	0.1103 (19)	−0.0268 (12)	0.0106 (13)	−0.0047 (14)

O1—C1	1.207 (2)	C9—C14	1.375 (3)
O2—C8	1.199 (2)	C10—C11	1.384 (3)
O3—C10	1.360 (2)	C11—C12	1.381 (3)
O3—C15	1.420 (3)	C12—C13	1.363 (4)
N1—C1	1.3982 (19)	C13—C14	1.379 (3)
N1—C8	1.404 (2)	C3—H3	0.9300
N1—C9	1.422 (2)	C4—H4	0.9300
C1—C2	1.479 (2)	C5—H5	0.9300
C2—C3	1.376 (2)	C6—H6	0.9300
C2—C7	1.381 (2)	C11—H11	0.9300
C3—C4	1.384 (3)	C12—H12	0.9300
C4—C5	1.376 (3)	C13—H13	0.9300
C5—C6	1.382 (3)	C14—H14	0.9300
C6—C7	1.376 (2)	C15—H15A	0.9600
C7—C8	1.478 (2)	C15—H15B	0.9600
C9—C10	1.390 (3)	C15—H15C	0.9600
C10—O3—C15	118.01 (16)	C10—C11—C12	119.6 (2)
C1—N1—C8	111.45 (12)	C11—C12—C13	121.5 (2)
C1—N1—C9	124.67 (13)	C12—C13—C14	119.4 (2)
C8—N1—C9	123.82 (13)	C9—C14—C13	119.9 (2)
O1—C1—N1	124.79 (14)	C2—C3—H3	121.00
O1—C1—C2	129.10 (14)	C4—C3—H3	121.00
N1—C1—C2	106.07 (13)	C3—C4—H4	119.00
C1—C2—C3	130.67 (15)	C5—C4—H4	119.00
C1—C2—C7	108.06 (13)	C4—C5—H5	119.00
C3—C2—C7	121.19 (16)	C6—C5—H5	119.00
C2—C3—C4	117.39 (17)	C5—C6—H6	121.00
C3—C4—C5	121.29 (17)	C7—C6—H6	121.00
C4—C5—C6	121.32 (18)	C10—C11—H11	120.00
C5—C6—C7	117.27 (17)	C12—C11—H11	120.00
C2—C7—C6	121.50 (15)	C11—C12—H12	119.00
C2—C7—C8	108.70 (14)	C13—C12—H12	119.00
C6—C7—C8	129.79 (15)	C12—C13—H13	120.00
O2—C8—N1	125.14 (15)	C14—C13—H13	120.00
O2—C8—C7	129.26 (15)	C9—C14—H14	120.00
N1—C8—C7	105.59 (12)	C13—C14—H14	120.00
N1—C9—C10	119.79 (15)	O3—C15—H15A	110.00
N1—C9—C14	119.34 (18)	O3—C15—H15B	109.00
C10—C9—C14	120.86 (16)	O3—C15—H15C	109.00
O3—C10—C9	116.81 (15)	H15A—C15—H15B	109.00
O3—C10—C11	124.44 (18)	H15A—C15—H15C	109.00
C9—C10—C11	118.75 (17)	H15B—C15—H15C	109.00
C15—O3—C10—C9	174.12 (17)	C3—C2—C7—C6	1.9 (2)
C15—O3—C10—C11	−6.5 (3)	C3—C2—C7—C8	−179.07 (14)
C8—N1—C1—O1	−177.05 (15)	C2—C3—C4—C5	−1.5 (3)
C8—N1—C1—C2	0.97 (17)	C3—C4—C5—C6	1.7 (3)
C9—N1—C1—O1	0.1 (3)	C4—C5—C6—C7	−0.1 (3)
C9—N1—C1—C2	178.09 (16)	C5—C6—C7—C2	−1.7 (2)
C1—N1—C8—O2	−177.22 (15)	C5—C6—C7—C8	179.52 (17)
C1—N1—C8—C7	1.25 (17)	C2—C7—C8—O2	175.22 (16)
C9—N1—C8—O2	5.6 (3)	C2—C7—C8—N1	−3.16 (16)
C9—N1—C8—C7	−175.90 (15)	C6—C7—C8—O2	−5.9 (3)
C1—N1—C9—C10	71.9 (2)	C6—C7—C8—N1	175.74 (15)
C1—N1—C9—C14	−109.5 (2)	N1—C9—C10—O3	−1.6 (3)
C8—N1—C9—C10	−111.38 (19)	N1—C9—C10—C11	179.02 (17)
C8—N1—C9—C14	67.2 (3)	C14—C9—C10—O3	179.80 (18)
O1—C1—C2—C3	−1.9 (3)	C14—C9—C10—C11	0.4 (3)
O1—C1—C2—C7	174.92 (16)	N1—C9—C14—C13	−178.45 (19)
N1—C1—C2—C3	−179.77 (16)	C10—C9—C14—C13	0.2 (3)
N1—C1—C2—C7	−2.98 (16)	O3—C10—C11—C12	−179.6 (2)
C1—C2—C3—C4	176.14 (17)	C9—C10—C11—C12	−0.3 (3)
C7—C2—C3—C4	−0.3 (2)	C10—C11—C12—C13	−0.4 (4)
C1—C2—C7—C6	−175.24 (14)	C11—C12—C13—C14	1.0 (4)
C1—C2—C7—C8	3.77 (17)	C12—C13—C14—C9	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.57	3.428 (2)	153
C12—H12···O2ii	0.93	2.46	3.313 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.57	3.428 (2)	153
C12—H12⋯O2ii	0.93	2.46	3.313 (2)	152

Symmetry codes: (i) ; (ii) .