N-(2,6-Dimethyl-phen-yl)succinimide.

The mol-ecule of the title compound, C(12)H(13)NO(2), lies on a twofold rotation axis that passes through the N and C(para) atoms as well as through the mid-point of the bond between the methyl-ene C atoms. The dihedral angle between the aromatic ring and the amide segment is 75.9 (1)°.

Related literature

For our studies on the effect of ring and side-chain substitutions on the structures of this class of compounds, see: Gowda et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C12H13NO2

M = 203.23

Tetragonal,

a = 9.4048 (3) Å

c = 23.685 (1) Å

V = 2094.94 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 299 K

0.44 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶)’ T min = 0.962, T max = 0.966

7329 measured reflections

1062 independent reflections

942 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.150

S = 1.11

1062 reflections

70 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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/S160053680905555X/ng2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905555X/ng2713Isup2.hkl

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

C12H13NO2	Dx = 1.289 Mg m−3
Mr = 203.23	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 5744 reflections
Hall symbol: -I 4ad	θ = 2.8–27.9°
a = 9.4048 (3) Å	µ = 0.09 mm−1
c = 23.685 (1) Å	T = 299 K
V = 2094.94 (13) Å3	Prism, colourless
Z = 8	0.44 × 0.44 × 0.40 mm
F(000) = 864

Oxford Diffraction Xcalibur diffractometer	1062 independent reflections
Radiation source: fine-focus sealed tube	942 reflections with I > 2σ(I)
graphite	Rint = 0.024
Rotation method data acquisition using ω and φ scans.	θmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)'	h = −11→11
Tmin = 0.962, Tmax = 0.966	k = −11→11
7329 measured reflections	l = −28→26

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0961P)2 + 0.6791P] where P = (Fo2 + 2Fc2)/3
1062 reflections	(Δ/σ)max < 0.001
70 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.5000	0.2500	0.10156 (7)	0.0325 (4)
C2	0.38264 (14)	0.30632 (13)	0.13004 (6)	0.0376 (4)
C3	0.38515 (18)	0.30545 (16)	0.18861 (6)	0.0499 (4)
H3	0.3086	0.3426	0.2086	0.060*
C4	0.5000	0.2500	0.21748 (9)	0.0570 (6)
H4	0.5000	0.2500	0.2567	0.068*
C5	0.58183 (14)	0.34178 (15)	0.00845 (6)	0.0401 (4)
C6	0.56001 (18)	0.30343 (18)	−0.05269 (6)	0.0504 (4)
H6A	0.6457	0.2621	−0.0685	0.060*
H6B	0.5346	0.3868	−0.0746	0.060*
C7	0.25630 (16)	0.36549 (17)	0.09927 (6)	0.0495 (4)
H7A	0.1918	0.2897	0.0902	0.059*
H7B	0.2873	0.4108	0.0651	0.059*
H7C	0.2090	0.4338	0.1228	0.059*
N1	0.5000	0.2500	0.04113 (6)	0.0335 (4)
O1	0.65642 (13)	0.43332 (13)	0.02778 (5)	0.0606 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (9)	0.0299 (8)	0.0292 (9)	−0.0041 (6)	0.000	0.000
C2	0.0424 (7)	0.0318 (7)	0.0384 (8)	−0.0004 (5)	0.0050 (5)	0.0021 (5)
C3	0.0661 (10)	0.0451 (8)	0.0384 (8)	0.0064 (7)	0.0143 (7)	−0.0008 (6)
C4	0.0886 (17)	0.0525 (12)	0.0299 (10)	0.0066 (11)	0.000	0.000
C5	0.0418 (7)	0.0430 (7)	0.0355 (7)	−0.0079 (5)	0.0002 (5)	0.0049 (5)
C6	0.0596 (9)	0.0590 (9)	0.0324 (8)	−0.0113 (7)	0.0035 (6)	0.0031 (6)
C7	0.0411 (8)	0.0509 (8)	0.0564 (9)	0.0065 (6)	0.0056 (6)	0.0070 (7)
N1	0.0345 (8)	0.0372 (8)	0.0290 (8)	−0.0047 (6)	0.000	0.000
O1	0.0700 (8)	0.0646 (8)	0.0470 (7)	−0.0348 (6)	−0.0061 (5)	0.0056 (5)

C1—C2i	1.3978 (15)	C5—N1	1.3916 (15)
C1—C2	1.3978 (15)	C5—C6	1.5064 (19)
C1—N1	1.431 (2)	C6—C6i	1.511 (3)
C2—C3	1.387 (2)	C6—H6A	0.9700
C2—C7	1.5008 (19)	C6—H6B	0.9700
C3—C4	1.3807 (19)	C7—H7A	0.9600
C3—H3	0.9300	C7—H7B	0.9600
C4—C3i	1.3807 (19)	C7—H7C	0.9600
C4—H4	0.9300	N1—C5i	1.3916 (15)
C5—O1	1.2012 (17)
C2i—C1—C2	122.29 (17)	C5—C6—C6i	105.13 (8)
C2i—C1—N1	118.85 (8)	C5—C6—H6A	110.7
C2—C1—N1	118.85 (8)	C6i—C6—H6A	110.7
C3—C2—C1	117.83 (13)	C5—C6—H6B	110.7
C3—C2—C7	120.07 (12)	C6i—C6—H6B	110.7
C1—C2—C7	122.10 (13)	H6A—C6—H6B	108.8
C4—C3—C2	120.71 (14)	C2—C7—H7A	109.5
C4—C3—H3	119.6	C2—C7—H7B	109.5
C2—C3—H3	119.6	H7A—C7—H7B	109.5
C3—C4—C3i	120.63 (19)	C2—C7—H7C	109.5
C3—C4—H4	119.7	H7A—C7—H7C	109.5
C3i—C4—H4	119.7	H7B—C7—H7C	109.5
O1—C5—N1	123.75 (13)	C5—N1—C5i	112.40 (15)
O1—C5—C6	128.14 (13)	C5—N1—C1	123.80 (8)
N1—C5—C6	108.11 (12)	C5i—N1—C1	123.80 (8)
C2i—C1—C2—C3	0.13 (9)	O1—C5—N1—C5i	177.17 (18)
N1—C1—C2—C3	−179.87 (9)	C6—C5—N1—C5i	−3.48 (8)
C2i—C1—C2—C7	−179.44 (14)	O1—C5—N1—C1	−2.83 (18)
N1—C1—C2—C7	0.56 (14)	C6—C5—N1—C1	176.52 (8)
C1—C2—C3—C4	−0.27 (19)	C2i—C1—N1—C5	−73.92 (9)
C7—C2—C3—C4	179.31 (11)	C2—C1—N1—C5	106.08 (9)
C2—C3—C4—C3i	0.14 (10)	C2i—C1—N1—C5i	106.08 (9)
O1—C5—C6—C6i	−171.85 (18)	C2—C1—N1—C5i	−73.92 (9)
N1—C5—C6—C6i	8.8 (2)