N-(3-Methyl-phen-yl)succinimide.

In the title compound, C(11)H(11)NO(2), the dihedral angle between the ring planes is 52.5 (1)°.

Related literature

For related structures, see: Saraswathi et al. (2010 ▶).

Experimental

Crystal data

C11H11NO2

M = 189.21

Monoclinic,

a = 7.7906 (9) Å

b = 6.6015 (8) Å

c = 19.511 (2) Å

β = 100.06 (1)°

V = 988.02 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 299 K

0.32 × 0.16 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.972, T max = 0.988

3757 measured reflections

2000 independent reflections

1453 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.168

S = 1.18

2000 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S1600536810015904/ng2766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015904/ng2766Isup2.hkl

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

C11H11NO2	F(000) = 400
Mr = 189.21	Dx = 1.272 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1573 reflections
a = 7.7906 (9) Å	θ = 2.6–27.7°
b = 6.6015 (8) Å	µ = 0.09 mm−1
c = 19.511 (2) Å	T = 299 K
β = 100.06 (1)°	Rod, colourless
V = 988.02 (19) Å3	0.32 × 0.16 × 0.14 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2000 independent reflections
Radiation source: fine-focus sealed tube	1453 reflections with I > 2σ(I)
graphite	Rint = 0.020
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.972, Tmax = 0.988	k = −8→6
3757 measured reflections	l = −24→22

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2000 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.0804 (2)	0.1090 (2)	0.35080 (8)	0.0418 (4)
C2	0.1645 (2)	−0.0080 (3)	0.40538 (9)	0.0477 (5)
H2	0.1895	−0.1430	0.3977	0.057*
C3	0.2117 (2)	0.0744 (3)	0.47137 (10)	0.0590 (5)
C4	0.1759 (3)	0.2780 (4)	0.48018 (12)	0.0717 (7)
H4	0.2069	0.3364	0.5240	0.086*
C5	0.0957 (3)	0.3947 (3)	0.42550 (12)	0.0699 (6)
H5	0.0744	0.5311	0.4325	0.084*
C6	0.0468 (3)	0.3106 (3)	0.36036 (10)	0.0552 (5)
H6	−0.0082	0.3892	0.3234	0.066*
C7	−0.0722 (2)	−0.1600 (3)	0.27360 (9)	0.0505 (5)
C8	−0.0778 (3)	−0.2276 (4)	0.20019 (10)	0.0679 (6)
H8A	−0.1969	−0.2528	0.1775	0.081*
H8B	−0.0103	−0.3505	0.1987	0.081*
C9	0.0004 (3)	−0.0551 (4)	0.16546 (10)	0.0710 (7)
H9A	0.0894	−0.1044	0.1405	0.085*
H9B	−0.0886	0.0143	0.1329	0.085*
C10	0.0783 (2)	0.0839 (3)	0.22331 (9)	0.0570 (5)
C11	0.2939 (3)	−0.0550 (5)	0.53171 (12)	0.0857 (8)
H11A	0.3588	−0.1625	0.5151	0.103*
H11B	0.2045	−0.1114	0.5541	0.103*
H11C	0.3709	0.0264	0.5644	0.103*
N1	0.02773 (18)	0.0164 (2)	0.28405 (7)	0.0438 (4)
O1	−0.1388 (2)	−0.2413 (2)	0.31764 (8)	0.0682 (5)
O2	0.1681 (2)	0.2311 (3)	0.22030 (8)	0.0867 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0422 (8)	0.0435 (9)	0.0422 (9)	−0.0036 (7)	0.0142 (7)	−0.0011 (7)
C2	0.0468 (9)	0.0519 (10)	0.0461 (10)	−0.0010 (8)	0.0131 (7)	0.0013 (8)
C3	0.0479 (10)	0.0869 (15)	0.0437 (10)	−0.0122 (10)	0.0123 (8)	−0.0003 (10)
C4	0.0711 (13)	0.0912 (17)	0.0566 (12)	−0.0205 (13)	0.0219 (10)	−0.0293 (12)
C5	0.0807 (14)	0.0573 (12)	0.0786 (16)	−0.0142 (12)	0.0330 (12)	−0.0206 (11)
C6	0.0573 (10)	0.0491 (11)	0.0631 (12)	−0.0030 (9)	0.0218 (9)	0.0037 (9)
C7	0.0442 (9)	0.0552 (11)	0.0521 (11)	−0.0006 (8)	0.0086 (8)	−0.0047 (8)
C8	0.0556 (11)	0.0902 (16)	0.0564 (12)	−0.0069 (11)	0.0057 (9)	−0.0211 (11)
C9	0.0618 (12)	0.1086 (18)	0.0423 (11)	0.0053 (12)	0.0086 (9)	−0.0046 (11)
C10	0.0505 (10)	0.0788 (14)	0.0436 (10)	−0.0027 (10)	0.0134 (8)	0.0103 (9)
C11	0.0681 (14)	0.138 (2)	0.0493 (12)	−0.0046 (15)	0.0058 (10)	0.0168 (13)
N1	0.0427 (7)	0.0491 (8)	0.0400 (8)	−0.0009 (6)	0.0085 (6)	0.0025 (6)
O1	0.0757 (9)	0.0631 (9)	0.0698 (9)	−0.0190 (7)	0.0235 (7)	−0.0006 (7)
O2	0.0944 (12)	0.1052 (13)	0.0646 (10)	−0.0348 (10)	0.0254 (9)	0.0154 (9)

C1—C6	1.375 (3)	C7—N1	1.396 (2)
C1—C2	1.385 (2)	C7—C8	1.494 (2)
C1—N1	1.432 (2)	C8—C9	1.507 (3)
C2—C3	1.387 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.389 (3)	C9—C10	1.498 (3)
C3—C11	1.504 (3)	C9—H9A	0.9700
C4—C5	1.375 (3)	C9—H9B	0.9700
C4—H4	0.9300	C10—O2	1.204 (2)
C5—C6	1.378 (3)	C10—N1	1.386 (2)
C5—H5	0.9300	C11—H11A	0.9600
C6—H6	0.9300	C11—H11B	0.9600
C7—O1	1.205 (2)	C11—H11C	0.9600
C6—C1—C2	120.76 (16)	C9—C8—H8A	110.7
C6—C1—N1	120.37 (15)	C7—C8—H8B	110.7
C2—C1—N1	118.87 (15)	C9—C8—H8B	110.7
C1—C2—C3	120.54 (18)	H8A—C8—H8B	108.8
C1—C2—H2	119.7	C10—C9—C8	105.46 (16)
C3—C2—H2	119.7	C10—C9—H9A	110.6
C2—C3—C4	117.90 (19)	C8—C9—H9A	110.6
C2—C3—C11	120.8 (2)	C10—C9—H9B	110.6
C4—C3—C11	121.3 (2)	C8—C9—H9B	110.6
C5—C4—C3	121.34 (19)	H9A—C9—H9B	108.8
C5—C4—H4	119.3	O2—C10—N1	123.72 (18)
C3—C4—H4	119.3	O2—C10—C9	128.29 (17)
C4—C5—C6	120.3 (2)	N1—C10—C9	107.98 (17)
C4—C5—H5	119.8	C3—C11—H11A	109.5
C6—C5—H5	119.8	C3—C11—H11B	109.5
C1—C6—C5	119.10 (19)	H11A—C11—H11B	109.5
C1—C6—H6	120.5	C3—C11—H11C	109.5
C5—C6—H6	120.5	H11A—C11—H11C	109.5
O1—C7—N1	124.49 (16)	H11B—C11—H11C	109.5
O1—C7—C8	127.37 (18)	C10—N1—C7	112.22 (15)
N1—C7—C8	108.13 (16)	C10—N1—C1	124.11 (15)
C7—C8—C9	105.02 (17)	C7—N1—C1	123.56 (13)
C7—C8—H8A	110.7
C6—C1—C2—C3	2.0 (3)	C8—C9—C10—N1	−8.2 (2)
N1—C1—C2—C3	−177.61 (15)	O2—C10—N1—C7	−178.5 (2)
C1—C2—C3—C4	−1.6 (3)	C9—C10—N1—C7	2.2 (2)
C1—C2—C3—C11	176.53 (16)	O2—C10—N1—C1	−2.1 (3)
C2—C3—C4—C5	0.2 (3)	C9—C10—N1—C1	178.57 (15)
C11—C3—C4—C5	−177.9 (2)	O1—C7—N1—C10	−175.92 (19)
C3—C4—C5—C6	0.8 (3)	C8—C7—N1—C10	5.0 (2)
C2—C1—C6—C5	−1.0 (3)	O1—C7—N1—C1	7.7 (3)
N1—C1—C6—C5	178.66 (16)	C8—C7—N1—C1	−171.46 (15)
C4—C5—C6—C1	−0.4 (3)	C6—C1—N1—C10	57.0 (2)
O1—C7—C8—C9	171.10 (19)	C2—C1—N1—C10	−123.42 (19)
N1—C7—C8—C9	−9.8 (2)	C6—C1—N1—C7	−127.04 (18)
C7—C8—C9—C10	10.8 (2)	C2—C1—N1—C7	52.6 (2)
C8—C9—C10—O2	172.5 (2)