2-(2-Meth­oxy­phen­yl)-1H-isoindole-1,3(2H)-dione

Abstract

In the title compound, C₁₅H₁₁NO₃, the dihedral angle between the meth­oxy­benzene and isoindole ring systems is 70.21 (3)°. The meth­oxy 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 inter­actions 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 _r = 253.25

• Orthorhombic,

• a = 11.5768 (6) Å

• b = 7.3222 (5) Å

• c = 29.2849 (15) Å

• V = 2482.4 (2) ų

• 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

• Δρ_max = 0.12 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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

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) .

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized in an attempt to form the carboxylic acid containing methoxybenzene. We have reported the crystal structure of 1-(2-methoxyphenyl)-1H-pyrrole-2,5-dione (Sirajuddin et al., 2012) which is related to (I). The polymorph of (I) has also been published by (Sim et al., 2009).

In (I), 1H-isoindole-1,3(2H)-dione A (C1—C8/N1/O1/O2) and the methoxybenzene B (C9—C15/O3) are almost planar with r.m.s. deviation of 0.0458 and 0.0320 Å, respectively. The dihedral angle between A/B is 70.21 (3)°. The molecules are dimerized due to C—H···O type of H-bonding with R₂²(10) ring motifs (Bernstein et al., 1995). The dimers are interlinked due to further C—H···O bonds to form infinite sheets. There exist π···π interaction between Cg1···Cg2ⁱ [i = 3/2 - x, -1/2 + y, z] and Cg2···Cg1ⁱⁱ [ii = 3/2 - x, 1/2 + y, z] at a distance of 3.7217 (10) Å. Similarly, there exist π···π interaction between Cg2··· Cg2ⁱ [i = 3/2 - x, -1/2 + y, z] and Cg2··· Cg2ⁱⁱ [ii = 3/2 - x, 1/2 + y, z] at a distance of 3.6990 (10) Å. Cg1 and Cg2 are the centroids of (C1/C2/C7/C8/N1) and (C2—C7) rings, respectively.

Experimental

Equimolar quantities of 2-methoxyaniline and phthalic anhydride were stirred and refluxed in acetic acid for 4 h. The solution was kept at room temperature which afforded dark yellow prisms after 12 h.

Refinement

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with U_iso(H) = xU_eq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.

Figures

Fig. 1.

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Fig. 2.

The partial packing, which shows that molecules form dimers with R22(10) ring mtifs and C(18) chains are formed due to C—H···O bonds.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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) −x+1, −y+1, −z; (ii) x−1/2, y, −z+1/2.