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

In the title compound, C(16)H(13)NO(2), the 2,3-dimethyl-phenyl group and the 1H-isoindole-1,3(2H)-dione group are essentially planar, with r.m.s. deviations of 0.006 and 0.013 Å, respectively, and are oriented at an angle of 78.19 (3)° with respect to each other. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a zigzag chain parallel to the b axis. Futhermore, C-H⋯π inter-actions are present between the C-H group of isoindole and the 2,3-dimethyl-phenyl benzene ring. The H atoms of the ortho-methyl group are statistically disordered over two positions. Such disorder might be related to the antagonism between intra-molecular steric repulsions and inter-molecular C-H⋯O inter-actions.

Related literature

For background to Schiff bases containing 2,3-dimethyl­aniline and for related structures, see: Bocelli & Cantoni (1989 ▶); Chandrashekar et al. (1983 ▶); Izotova et al. (2009 ▶); Sarfraz et al. (2010 ▶); Tahir et al. (2010 ▶); Tariq et al. (2010 ▶).

Experimental

Crystal data

C16H13NO2

M = 251.27

Monoclinic,

a = 7.8222 (3) Å

b = 8.4576 (3) Å

c = 19.4863 (6) Å

β = 91.441 (2)°

V = 1288.75 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.993

9849 measured reflections

2320 independent reflections

1819 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.04

2320 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 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: 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 datablocks global, I. DOI: 10.1107/S1600536810033386/dn2596sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033386/dn2596Isup2.hkl

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

C16H13NO2	F(000) = 528
Mr = 251.27	Dx = 1.295 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1819 reflections
a = 7.8222 (3) Å	θ = 2.6–25.2°
b = 8.4576 (3) Å	µ = 0.09 mm−1
c = 19.4863 (6) Å	T = 296 K
β = 91.441 (2)°	Prism, white
V = 1288.75 (8) Å3	0.30 × 0.12 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	2320 independent reflections
Radiation source: fine-focus sealed tube	1819 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 8.10 pixels mm-1	θmax = 25.2°, θmin = 2.6°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.980, Tmax = 0.993	l = −23→23
9849 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.2276P] where P = (Fo2 + 2Fc2)/3
2320 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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	Occ. (<1)
O1	0.49485 (18)	0.42949 (17)	0.22907 (6)	0.0925 (5)
O2	0.79930 (14)	0.38827 (14)	0.03357 (5)	0.0628 (3)
N1	0.61379 (16)	0.38436 (14)	0.12397 (6)	0.0490 (3)
C1	0.49387 (19)	0.26593 (18)	0.10015 (7)	0.0467 (4)
C2	0.53838 (18)	0.10792 (18)	0.10503 (6)	0.0450 (4)
C3	0.41581 (19)	−0.00524 (18)	0.08357 (7)	0.0489 (4)
C4	0.2583 (2)	0.0467 (2)	0.05916 (7)	0.0598 (4)
H4	0.1775	−0.0278	0.0449	0.072*
C5	0.2167 (2)	0.2044 (2)	0.05521 (8)	0.0671 (5)
H5	0.1092	0.2354	0.0388	0.080*
C6	0.3357 (2)	0.3165 (2)	0.07580 (8)	0.0579 (4)
H6	0.3099	0.4237	0.0733	0.069*
C7	0.7094 (2)	0.0574 (2)	0.13251 (8)	0.0591 (4)
H7A	0.7165	−0.0559	0.1318	0.089*	0.50
H7B	0.7247	0.0945	0.1788	0.089*	0.50
H7C	0.7970	0.1010	0.1046	0.089*	0.50
H7D	0.7756	0.1490	0.1450	0.089*	0.50
H7E	0.7675	−0.0015	0.0980	0.089*	0.50
H7F	0.6951	−0.0079	0.1723	0.089*	0.50
C8	0.4548 (2)	−0.1781 (2)	0.08813 (9)	0.0665 (5)
H8A	0.3620	−0.2372	0.0677	0.100*
H8B	0.4697	−0.2079	0.1354	0.100*
H8C	0.5579	−0.2001	0.0642	0.100*
C9	0.6040 (2)	0.45618 (19)	0.18862 (7)	0.0555 (4)
C10	0.75207 (18)	0.56363 (17)	0.19457 (7)	0.0457 (4)
C11	0.8017 (2)	0.66315 (19)	0.24722 (7)	0.0562 (4)
H11	0.7393	0.6707	0.2871	0.067*
C12	0.9479 (2)	0.7513 (2)	0.23830 (8)	0.0622 (4)
H12	0.9848	0.8199	0.2729	0.075*
C13	1.0403 (2)	0.7399 (2)	0.17923 (9)	0.0652 (5)
H13	1.1387	0.8005	0.1749	0.078*
C14	0.9898 (2)	0.6399 (2)	0.12609 (8)	0.0565 (4)
H14	1.0520	0.6326	0.0862	0.068*
C15	0.84406 (18)	0.55212 (16)	0.13486 (7)	0.0432 (3)
C16	0.75805 (19)	0.43515 (17)	0.08932 (7)	0.0463 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0969 (10)	0.1151 (11)	0.0678 (8)	−0.0452 (9)	0.0465 (8)	−0.0311 (7)
O2	0.0700 (8)	0.0772 (8)	0.0420 (6)	−0.0077 (6)	0.0174 (5)	−0.0097 (5)
N1	0.0550 (8)	0.0515 (7)	0.0412 (6)	−0.0075 (6)	0.0130 (5)	−0.0041 (5)
C1	0.0521 (9)	0.0521 (9)	0.0363 (7)	−0.0015 (7)	0.0086 (6)	−0.0002 (6)
C2	0.0462 (8)	0.0558 (9)	0.0332 (7)	0.0017 (7)	0.0064 (6)	0.0019 (6)
C3	0.0528 (9)	0.0580 (9)	0.0364 (7)	−0.0068 (7)	0.0081 (6)	0.0004 (6)
C4	0.0569 (10)	0.0754 (12)	0.0469 (9)	−0.0121 (9)	0.0012 (7)	0.0016 (8)
C5	0.0491 (10)	0.0938 (14)	0.0580 (10)	0.0064 (10)	−0.0028 (8)	0.0117 (9)
C6	0.0560 (10)	0.0646 (10)	0.0532 (9)	0.0073 (8)	0.0041 (7)	0.0079 (8)
C7	0.0575 (10)	0.0606 (10)	0.0591 (9)	0.0025 (8)	0.0014 (8)	0.0047 (8)
C8	0.0784 (13)	0.0584 (10)	0.0630 (10)	−0.0083 (9)	0.0117 (9)	−0.0041 (8)
C9	0.0642 (10)	0.0581 (10)	0.0450 (8)	−0.0058 (8)	0.0175 (7)	−0.0056 (7)
C10	0.0514 (9)	0.0451 (8)	0.0410 (7)	0.0039 (7)	0.0063 (6)	0.0009 (6)
C11	0.0627 (11)	0.0614 (10)	0.0450 (8)	0.0008 (8)	0.0077 (7)	−0.0068 (7)
C12	0.0637 (11)	0.0645 (11)	0.0581 (10)	−0.0053 (9)	−0.0037 (8)	−0.0118 (8)
C13	0.0554 (10)	0.0726 (12)	0.0677 (11)	−0.0122 (9)	0.0030 (8)	−0.0031 (9)
C14	0.0520 (10)	0.0662 (10)	0.0516 (9)	−0.0021 (8)	0.0103 (7)	0.0020 (8)
C15	0.0460 (8)	0.0444 (8)	0.0394 (7)	0.0049 (7)	0.0045 (6)	0.0039 (6)
C16	0.0507 (9)	0.0494 (9)	0.0392 (7)	0.0038 (7)	0.0090 (6)	0.0029 (6)

O1—C9	1.1982 (17)	C7—H7D	0.9600
O2—C16	1.2079 (16)	C7—H7E	0.9600
N1—C16	1.3972 (17)	C7—H7F	0.9600
N1—C9	1.4025 (18)	C8—H8A	0.9600
N1—C1	1.4411 (19)	C8—H8B	0.9600
C1—C6	1.382 (2)	C8—H8C	0.9600
C1—C2	1.384 (2)	C9—C10	1.474 (2)
C2—C3	1.411 (2)	C10—C11	1.375 (2)
C2—C7	1.491 (2)	C10—C15	1.3867 (18)
C3—C4	1.381 (2)	C11—C12	1.380 (2)
C3—C8	1.496 (2)	C11—H11	0.9300
C4—C5	1.375 (3)	C12—C13	1.378 (2)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.381 (2)	C13—C14	1.386 (2)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.375 (2)
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	C15—C16	1.479 (2)
C7—H7C	0.9600
C16—N1—C9	111.33 (12)	C2—C7—H7F	109.5
C16—N1—C1	125.81 (11)	H7A—C7—H7F	56.3
C9—N1—C1	122.73 (11)	H7B—C7—H7F	56.3
C6—C1—C2	122.96 (14)	H7C—C7—H7F	141.1
C6—C1—N1	117.74 (14)	H7D—C7—H7F	109.5
C2—C1—N1	119.25 (13)	H7E—C7—H7F	109.5
C1—C2—C3	117.84 (14)	C3—C8—H8A	109.5
C1—C2—C7	121.57 (14)	C3—C8—H8B	109.5
C3—C2—C7	120.59 (14)	H8A—C8—H8B	109.5
C4—C3—C2	118.69 (15)	C3—C8—H8C	109.5
C4—C3—C8	120.68 (15)	H8A—C8—H8C	109.5
C2—C3—C8	120.62 (15)	H8B—C8—H8C	109.5
C5—C4—C3	122.39 (16)	O1—C9—N1	124.41 (15)
C5—C4—H4	118.8	O1—C9—C10	129.49 (14)
C3—C4—H4	118.8	N1—C9—C10	106.09 (11)
C4—C5—C6	119.53 (16)	C11—C10—C15	121.76 (14)
C4—C5—H5	120.2	C11—C10—C9	129.95 (13)
C6—C5—H5	120.2	C15—C10—C9	108.29 (12)
C5—C6—C1	118.59 (16)	C10—C11—C12	117.11 (14)
C5—C6—H6	120.7	C10—C11—H11	121.4
C1—C6—H6	120.7	C12—C11—H11	121.4
C2—C7—H7A	109.5	C13—C12—C11	121.42 (15)
C2—C7—H7B	109.5	C13—C12—H12	119.3
H7A—C7—H7B	109.5	C11—C12—H12	119.3
C2—C7—H7C	109.5	C12—C13—C14	121.41 (16)
H7A—C7—H7C	109.5	C12—C13—H13	119.3
H7B—C7—H7C	109.5	C14—C13—H13	119.3
C2—C7—H7D	109.5	C15—C14—C13	117.26 (14)
H7A—C7—H7D	141.1	C15—C14—H14	121.4
H7B—C7—H7D	56.3	C13—C14—H14	121.4
H7C—C7—H7D	56.3	C14—C15—C10	121.05 (13)
C2—C7—H7E	109.5	C14—C15—C16	130.74 (12)
H7A—C7—H7E	56.3	C10—C15—C16	108.21 (12)
H7B—C7—H7E	141.1	O2—C16—N1	124.82 (14)
H7C—C7—H7E	56.3	O2—C16—C15	129.14 (13)
H7D—C7—H7E	109.5	N1—C16—C15	106.04 (11)

Cg2 is the centroid of the C1—C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7D···N1	0.96	2.39	2.868 (2)	110.
C7—H7F···O1i	0.96	2.52	3.3486 (19)	145.
C8—H8C···Cg2ii	0.96	2.89	3.5644 (18)	128
C11—H11···Cg2iii	0.93	2.77	3.6798 (15)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1—C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7F⋯O1i	0.96	2.52	3.3486 (19)	145
C8—H8C⋯Cg2ii	0.96	2.89	3.5644 (18)	128
C11—H11⋯Cg2iii	0.93	2.77	3.6798 (15)	166

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