N-(2,4-Dimethyl-phen-yl)succinimide.

In the title compound, C(12)H(13)NO(2), the dihedral angle between the benzene ring and the imide segment is 85.7 (1)°. In the crystal, the mol-ecules are packed into zigzag chains parallel to the a 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

Orthorhombic,

a = 7.1461 (7) Å

b = 11.182 (2) Å

c = 13.676 (2) Å

V = 1092.8 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 299 K

0.50 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

2947 measured reflections

1152 independent reflections

987 reflections with I > 2σ(I)

R int = 0.065

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.06

1152 reflections

157 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.17 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/S1600536810009694/vm2021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009694/vm2021Isup2.hkl

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

C12H13NO2	F(000) = 432
Mr = 203.23	Dx = 1.235 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.1461 (7) Å	θ = 5.1–23.4°
b = 11.182 (2) Å	µ = 0.68 mm−1
c = 13.676 (2) Å	T = 299 K
V = 1092.8 (3) Å3	Rod, colourless
Z = 4	0.50 × 0.25 × 0.25 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.065
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 5.1°
graphite	h = −3→8
ω/2θ scans	k = −13→13
2947 measured reflections	l = 0→16
1152 independent reflections	3 standard reflections every 120 min
987 reflections with I > 2σ(I)	intensity decay: 1.0%

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) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3
1152 reflections	(Δ/σ)max = 0.011
157 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.17 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
C1	−0.0480 (4)	0.0411 (2)	0.04393 (17)	0.0377 (6)
C2	−0.2151 (4)	−0.0128 (2)	0.07236 (18)	0.0410 (6)
C3	−0.2763 (4)	−0.1082 (2)	0.0153 (2)	0.0461 (6)
H3	−0.400 (5)	−0.144 (3)	0.034 (2)	0.055*
C4	−0.1827 (4)	−0.1484 (2)	−0.06581 (18)	0.0469 (6)
C5	−0.0181 (4)	−0.0909 (3)	−0.0921 (2)	0.0488 (7)
H5	0.042 (5)	−0.111 (3)	−0.153 (2)	0.059*
C6	0.0488 (4)	0.0035 (3)	−0.0372 (2)	0.0462 (7)
H6	0.184 (5)	0.035 (3)	−0.049 (2)	0.055*
C7	−0.0064 (4)	0.2593 (2)	0.06994 (18)	0.0429 (6)
C8	0.0891 (5)	0.3392 (2)	0.1425 (2)	0.0483 (7)
H8A	0.164 (5)	0.390 (3)	0.107 (2)	0.058*
H8B	−0.013 (5)	0.391 (3)	0.1798 (19)	0.058*
C9	0.1992 (5)	0.2553 (3)	0.2077 (2)	0.0478 (7)
H9A	0.182 (5)	0.264 (3)	0.273 (3)	0.057*
H9B	0.325 (5)	0.267 (3)	0.193 (2)	0.057*
C10	0.1393 (4)	0.1310 (2)	0.17959 (17)	0.0427 (6)
C11	−0.3240 (5)	0.0311 (3)	0.1583 (2)	0.0581 (8)
H11A	−0.3491	0.1150	0.1507	0.070*
H11B	−0.2529	0.0185	0.2169	0.070*
H11C	−0.4400	−0.0118	0.1625	0.070*
C12	−0.2569 (6)	−0.2502 (3)	−0.1256 (2)	0.0683 (10)
H12A	−0.2704	−0.3197	−0.0849	0.082*
H12B	−0.1714	−0.2674	−0.1779	0.082*
H12C	−0.3765	−0.2288	−0.1523	0.082*
N1	0.0217 (3)	0.14153 (17)	0.09856 (13)	0.0376 (5)
O1	−0.0975 (3)	0.28747 (18)	−0.00034 (16)	0.0666 (7)
O2	0.1797 (4)	0.03828 (17)	0.21710 (15)	0.0634 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0370 (13)	0.0333 (12)	0.0428 (12)	−0.0018 (10)	−0.0027 (11)	0.0014 (10)
C2	0.0362 (13)	0.0422 (12)	0.0447 (12)	−0.0015 (11)	0.0014 (12)	0.0064 (10)
C3	0.0418 (14)	0.0410 (13)	0.0554 (14)	−0.0095 (12)	−0.0025 (13)	0.0064 (11)
C4	0.0557 (16)	0.0388 (12)	0.0462 (13)	−0.0038 (13)	−0.0092 (13)	0.0017 (11)
C5	0.0505 (15)	0.0511 (15)	0.0448 (13)	0.0000 (13)	0.0040 (14)	−0.0067 (12)
C6	0.0380 (14)	0.0486 (15)	0.0521 (14)	−0.0044 (12)	0.0055 (13)	−0.0029 (11)
C7	0.0385 (13)	0.0368 (12)	0.0534 (13)	0.0039 (11)	−0.0018 (13)	−0.0007 (11)
C8	0.0501 (16)	0.0375 (13)	0.0571 (15)	−0.0026 (13)	−0.0003 (15)	−0.0054 (12)
C9	0.0444 (15)	0.0526 (15)	0.0463 (14)	−0.0084 (14)	−0.0032 (14)	−0.0062 (12)
C10	0.0390 (13)	0.0472 (14)	0.0419 (12)	−0.0021 (12)	−0.0006 (11)	−0.0001 (11)
C11	0.0522 (17)	0.0627 (17)	0.0595 (16)	−0.0011 (16)	0.0141 (15)	−0.0013 (14)
C12	0.083 (3)	0.0562 (17)	0.0657 (17)	−0.0156 (18)	−0.0154 (19)	−0.0090 (15)
N1	0.0353 (11)	0.0353 (10)	0.0422 (10)	−0.0008 (9)	−0.0031 (9)	−0.0015 (8)
O1	0.0745 (15)	0.0501 (12)	0.0754 (12)	0.0086 (11)	−0.0306 (13)	0.0057 (11)
O2	0.0710 (15)	0.0525 (12)	0.0665 (12)	−0.0038 (11)	−0.0214 (12)	0.0138 (10)

C1—C6	1.373 (4)	C8—C9	1.514 (4)
C1—C2	1.393 (4)	C8—H8A	0.92 (3)
C1—N1	1.438 (3)	C8—H8B	1.06 (3)
C2—C3	1.392 (4)	C9—C10	1.505 (4)
C2—C11	1.493 (4)	C9—H9A	0.91 (3)
C3—C4	1.372 (4)	C9—H9B	0.93 (4)
C3—H3	1.00 (3)	C10—O2	1.192 (3)
C4—C5	1.388 (4)	C10—N1	1.396 (3)
C4—C12	1.498 (4)	C11—H11A	0.9600
C5—C6	1.381 (4)	C11—H11B	0.9600
C5—H5	0.97 (3)	C11—H11C	0.9600
C6—H6	1.04 (3)	C12—H12A	0.9600
C7—O1	1.203 (3)	C12—H12B	0.9600
C7—N1	1.388 (3)	C12—H12C	0.9600
C7—C8	1.499 (4)
C6—C1—C2	121.6 (2)	H8A—C8—H8B	108 (3)
C6—C1—N1	119.0 (2)	C10—C9—C8	105.9 (2)
C2—C1—N1	119.3 (2)	C10—C9—H9A	108 (2)
C1—C2—C3	116.4 (2)	C8—C9—H9A	116 (2)
C1—C2—C11	121.6 (2)	C10—C9—H9B	110 (2)
C3—C2—C11	122.0 (2)	C8—C9—H9B	106.8 (19)
C4—C3—C2	123.5 (3)	H9A—C9—H9B	109 (3)
C4—C3—H3	120.1 (17)	O2—C10—N1	124.1 (2)
C2—C3—H3	116.3 (17)	O2—C10—C9	128.7 (2)
C3—C4—C5	118.1 (2)	N1—C10—C9	107.2 (2)
C3—C4—C12	121.2 (3)	C2—C11—H11A	109.5
C5—C4—C12	120.7 (3)	C2—C11—H11B	109.5
C6—C5—C4	120.4 (3)	H11A—C11—H11B	109.5
C6—C5—H5	120 (2)	C2—C11—H11C	109.5
C4—C5—H5	120 (2)	H11A—C11—H11C	109.5
C1—C6—C5	120.0 (3)	H11B—C11—H11C	109.5
C1—C6—H6	119.3 (16)	C4—C12—H12A	109.5
C5—C6—H6	119.7 (16)	C4—C12—H12B	109.5
O1—C7—N1	123.5 (2)	H12A—C12—H12B	109.5
O1—C7—C8	128.3 (2)	C4—C12—H12C	109.5
N1—C7—C8	108.2 (2)	H12A—C12—H12C	109.5
C7—C8—C9	104.9 (2)	H12B—C12—H12C	109.5
C7—C8—H8A	106.3 (19)	C7—N1—C10	113.0 (2)
C9—C8—H8A	113 (2)	C7—N1—C1	122.9 (2)
C7—C8—H8B	109.2 (18)	C10—N1—C1	123.7 (2)
C9—C8—H8B	114.2 (15)
C6—C1—C2—C3	1.2 (4)	C7—C8—C9—C10	−8.4 (3)
N1—C1—C2—C3	178.9 (2)	C8—C9—C10—O2	−173.7 (3)
C6—C1—C2—C11	−177.6 (2)	C8—C9—C10—N1	6.0 (3)
N1—C1—C2—C11	0.0 (4)	O1—C7—N1—C10	177.2 (3)
C1—C2—C3—C4	−0.9 (4)	C8—C7—N1—C10	−4.6 (3)
C11—C2—C3—C4	178.0 (3)	O1—C7—N1—C1	3.2 (4)
C2—C3—C4—C5	0.1 (4)	C8—C7—N1—C1	−178.6 (2)
C2—C3—C4—C12	−178.9 (3)	O2—C10—N1—C7	178.8 (3)
C3—C4—C5—C6	0.5 (4)	C9—C10—N1—C7	−0.9 (3)
C12—C4—C5—C6	179.5 (3)	O2—C10—N1—C1	−7.2 (4)
C2—C1—C6—C5	−0.7 (4)	C9—C10—N1—C1	173.0 (2)
N1—C1—C6—C5	−178.4 (3)	C6—C1—N1—C7	80.0 (3)
C4—C5—C6—C1	−0.2 (4)	C2—C1—N1—C7	−97.8 (3)
O1—C7—C8—C9	−173.9 (3)	C6—C1—N1—C10	−93.4 (3)
N1—C7—C8—C9	8.1 (3)	C2—C1—N1—C10	88.9 (3)