N-(2,3-Dimethyl-phen-yl)succinimide.

In the title compound, C(12)H(13)NO(2), the dihedral angle between the aromatic benzene ring and the imide segment is 67.7 (1)°. The mol-ecules in the crystal are packed into layered chains along the c axis.

Related literature

For our study of the effect of ring and side-chain substitutions on the structures of biologically significant compounds, see: Gowda et al. (2007 ▶); Saraswathi et al. (2010 ▶).

Experimental

Crystal data

C12H13NO2

M = 203.23

Monoclinic,

a = 6.0600 (5) Å

b = 16.429 (2) Å

c = 10.593 (1) Å

β = 91.992 (8)°

V = 1054.00 (18) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 299 K

0.40 × 0.20 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

2096 measured reflections

1883 independent reflections

1472 reflections with I > 2σ(I)

R int = 0.016

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.05

1883 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001055X/ng2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001055X/ng2748Isup2.hkl

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

C12H13NO2	F(000) = 432
Mr = 203.23	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.0600 (5) Å	θ = 5.4–18.0°
b = 16.429 (2) Å	µ = 0.71 mm−1
c = 10.593 (1) Å	T = 299 K
β = 91.992 (8)°	Prism, colourless
V = 1054.00 (18) Å3	0.40 × 0.20 × 0.15 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 5.0°
graphite	h = −7→1
ω/2θ scans	k = −19→0
2096 measured reflections	l = −12→12
1883 independent reflections	3 standard reflections every 120 min
1472 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.2594P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1883 reflections	Δρmax = 0.18 e Å−3
139 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0081 (9)

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
C1	0.0295 (3)	0.64329 (10)	0.78424 (14)	0.0372 (4)
C2	0.1636 (3)	0.60330 (10)	0.70029 (15)	0.0376 (4)
C3	0.1134 (3)	0.61237 (11)	0.57082 (15)	0.0452 (4)
C4	−0.0697 (3)	0.65748 (12)	0.53242 (17)	0.0546 (5)
H4	−0.1026	0.6632	0.4465	0.066*
C5	−0.2041 (3)	0.69410 (12)	0.61716 (19)	0.0557 (5)
H5	−0.3281	0.7230	0.5888	0.067*
C6	−0.1541 (3)	0.68768 (11)	0.74460 (18)	0.0467 (4)
H6	−0.2424	0.7128	0.8031	0.056*
C7	0.2655 (3)	0.67879 (11)	0.97290 (16)	0.0449 (4)
C8	0.2745 (3)	0.65793 (14)	1.11109 (17)	0.0579 (5)
H8A	0.2780	0.7069	1.1622	0.069*
H8B	0.4045	0.6256	1.1324	0.069*
C9	0.0665 (4)	0.60978 (13)	1.13227 (17)	0.0567 (5)
H9A	0.1021	0.5571	1.1689	0.068*
H9B	−0.0287	0.6388	1.1887	0.068*
C10	−0.0448 (3)	0.59991 (11)	1.00467 (17)	0.0461 (4)
C11	0.3529 (3)	0.55084 (11)	0.74623 (17)	0.0478 (5)
H11A	0.3393	0.5398	0.8346	0.057*
H11B	0.4896	0.5787	0.7332	0.057*
H11C	0.3509	0.5005	0.7002	0.057*
C12	0.2559 (4)	0.57447 (15)	0.47345 (18)	0.0657 (6)
H12A	0.2417	0.5163	0.4767	0.079*
H12B	0.4072	0.5894	0.4905	0.079*
H12C	0.2098	0.5935	0.3910	0.079*
N1	0.0830 (2)	0.63939 (9)	0.91715 (12)	0.0393 (4)
O1	0.3887 (2)	0.72166 (9)	0.91606 (13)	0.0598 (4)
O2	−0.2143 (2)	0.56450 (9)	0.97796 (13)	0.0629 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0369 (8)	0.0402 (9)	0.0343 (8)	−0.0050 (7)	0.0002 (6)	0.0017 (7)
C2	0.0378 (8)	0.0377 (8)	0.0372 (8)	−0.0035 (7)	0.0002 (7)	0.0019 (7)
C3	0.0537 (10)	0.0461 (10)	0.0357 (9)	−0.0048 (8)	0.0001 (7)	0.0012 (7)
C4	0.0657 (12)	0.0582 (12)	0.0387 (10)	−0.0021 (10)	−0.0131 (9)	0.0073 (9)
C5	0.0473 (10)	0.0570 (12)	0.0618 (12)	0.0069 (9)	−0.0129 (9)	0.0082 (9)
C6	0.0387 (9)	0.0495 (10)	0.0519 (10)	0.0029 (8)	0.0027 (8)	0.0018 (8)
C7	0.0419 (9)	0.0512 (11)	0.0415 (9)	−0.0016 (8)	0.0015 (7)	−0.0083 (8)
C8	0.0617 (12)	0.0701 (13)	0.0411 (10)	−0.0007 (10)	−0.0073 (9)	−0.0074 (9)
C9	0.0758 (14)	0.0576 (12)	0.0369 (10)	−0.0013 (10)	0.0049 (9)	0.0013 (9)
C10	0.0510 (11)	0.0458 (10)	0.0417 (9)	0.0011 (8)	0.0053 (8)	0.0052 (8)
C11	0.0466 (10)	0.0521 (11)	0.0449 (10)	0.0058 (8)	0.0032 (8)	0.0025 (8)
C12	0.0805 (15)	0.0784 (15)	0.0385 (10)	0.0053 (12)	0.0067 (10)	−0.0076 (10)
N1	0.0396 (7)	0.0456 (8)	0.0328 (7)	−0.0029 (6)	0.0031 (6)	0.0000 (6)
O1	0.0493 (8)	0.0726 (10)	0.0576 (8)	−0.0187 (7)	0.0058 (6)	−0.0073 (7)
O2	0.0546 (8)	0.0747 (10)	0.0592 (8)	−0.0185 (7)	0.0015 (7)	0.0170 (7)

C1—C6	1.383 (2)	C8—C9	1.512 (3)
C1—C2	1.390 (2)	C8—H8A	0.9700
C1—N1	1.435 (2)	C8—H8B	0.9700
C2—C3	1.402 (2)	C9—C10	1.498 (3)
C2—C11	1.502 (2)	C9—H9A	0.9700
C3—C4	1.384 (3)	C9—H9B	0.9700
C3—C12	1.503 (3)	C10—O2	1.206 (2)
C4—C5	1.372 (3)	C10—N1	1.389 (2)
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.377 (3)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	C12—H12A	0.9600
C7—O1	1.203 (2)	C12—H12B	0.9600
C7—N1	1.395 (2)	C12—H12C	0.9600
C7—C8	1.503 (3)
C6—C1—C2	122.47 (15)	H8A—C8—H8B	108.8
C6—C1—N1	118.25 (15)	C10—C9—C8	105.92 (15)
C2—C1—N1	119.28 (14)	C10—C9—H9A	110.6
C1—C2—C3	117.62 (15)	C8—C9—H9A	110.6
C1—C2—C11	121.38 (15)	C10—C9—H9B	110.6
C3—C2—C11	120.98 (15)	C8—C9—H9B	110.6
C4—C3—C2	119.26 (17)	H9A—C9—H9B	108.7
C4—C3—C12	119.62 (17)	O2—C10—N1	123.97 (17)
C2—C3—C12	121.12 (17)	O2—C10—C9	128.09 (17)
C5—C4—C3	122.07 (17)	N1—C10—C9	107.93 (15)
C5—C4—H4	119.0	C2—C11—H11A	109.5
C3—C4—H4	119.0	C2—C11—H11B	109.5
C4—C5—C6	119.49 (17)	H11A—C11—H11B	109.5
C4—C5—H5	120.3	C2—C11—H11C	109.5
C6—C5—H5	120.3	H11A—C11—H11C	109.5
C5—C6—C1	119.02 (17)	H11B—C11—H11C	109.5
C5—C6—H6	120.5	C3—C12—H12A	109.5
C1—C6—H6	120.5	C3—C12—H12B	109.5
O1—C7—N1	123.82 (16)	H12A—C12—H12B	109.5
O1—C7—C8	128.24 (17)	C3—C12—H12C	109.5
N1—C7—C8	107.95 (15)	H12A—C12—H12C	109.5
C7—C8—C9	105.16 (15)	H12B—C12—H12C	109.5
C7—C8—H8A	110.7	C10—N1—C7	112.72 (14)
C9—C8—H8A	110.7	C10—N1—C1	124.29 (14)
C7—C8—H8B	110.7	C7—N1—C1	122.92 (14)
C9—C8—H8B	110.7
C6—C1—C2—C3	3.0 (2)	C7—C8—C9—C10	3.9 (2)
N1—C1—C2—C3	−176.40 (15)	C8—C9—C10—O2	178.99 (19)
C6—C1—C2—C11	−175.79 (16)	C8—C9—C10—N1	−0.8 (2)
N1—C1—C2—C11	4.8 (2)	O2—C10—N1—C7	177.23 (18)
C1—C2—C3—C4	−2.4 (2)	C9—C10—N1—C7	−2.9 (2)
C11—C2—C3—C4	176.39 (17)	O2—C10—N1—C1	0.2 (3)
C1—C2—C3—C12	177.13 (18)	C9—C10—N1—C1	−179.96 (16)
C11—C2—C3—C12	−4.1 (3)	O1—C7—N1—C10	−174.22 (17)
C2—C3—C4—C5	0.2 (3)	C8—C7—N1—C10	5.5 (2)
C12—C3—C4—C5	−179.3 (2)	O1—C7—N1—C1	2.9 (3)
C3—C4—C5—C6	1.5 (3)	C8—C7—N1—C1	−177.41 (15)
C4—C5—C6—C1	−0.9 (3)	C6—C1—N1—C10	67.5 (2)
C2—C1—C6—C5	−1.4 (3)	C2—C1—N1—C10	−113.08 (19)
N1—C1—C6—C5	178.08 (16)	C6—C1—N1—C7	−109.27 (19)
O1—C7—C8—C9	174.0 (2)	C2—C1—N1—C7	70.2 (2)
N1—C7—C8—C9	−5.7 (2)