N-(4-Methyl-phen-yl)succinimide.

In the mol-ecule of the title compound, C(11)H(11)NO(2), the dihedral angle between the aromatic ring and the amide segment is 57.3 (1)°.

Related literature

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

Experimental

Crystal data

C11H11NO2

M = 189.21

Monoclinic,

a = 13.543 (3) Å

b = 5.6539 (9) Å

c = 13.365 (3) Å

β = 109.35 (2)°

V = 965.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 299 K

0.44 × 0.24 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.961, T max = 0.993

3389 measured reflections

1924 independent reflections

1262 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.136

S = 1.23

1924 reflections

160 parameters

Only H-atom coordinates refined

Δρmax = 0.17 e Å−3

Δρmin = −0.16 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/S1600536810001546/ng2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001546/ng2719Isup2.hkl

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

C11H11NO2	F(000) = 400
Mr = 189.21	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1028 reflections
a = 13.543 (3) Å	θ = 2.6–27.8°
b = 5.6539 (9) Å	µ = 0.09 mm−1
c = 13.365 (3) Å	T = 299 K
β = 109.35 (2)°	Plate, colourless
V = 965.6 (3) Å3	0.44 × 0.24 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1924 independent reflections
Radiation source: fine-focus sealed tube	1262 reflections with I > 2σ(I)
graphite	Rint = 0.020
Rotation method data acquisition using ω and φ scans.	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→11
Tmin = 0.961, Tmax = 0.993	k = −7→7
3389 measured reflections	l = −16→15

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)] = 0.068	Hydrogen site location: difference Fourier map
wR(F2) = 0.136	Only H-atom coordinates refined
S = 1.23	w = 1/[σ2(Fo2) + (0.0241P)2 + 0.6535P] where P = (Fo2 + 2Fc2)/3
1924 reflections	(Δ/σ)max = 0.017
160 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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

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	0.25083 (19)	0.2010 (5)	0.2351 (2)	0.0412 (6)
C2	0.2495 (2)	0.0189 (5)	0.3031 (2)	0.0531 (8)
H2	0.293 (2)	−0.118 (5)	0.306 (2)	0.064*
C3	0.1863 (3)	0.0374 (6)	0.3657 (2)	0.0602 (9)
H3	0.187 (2)	−0.089 (5)	0.412 (2)	0.072*
C4	0.1243 (2)	0.2332 (6)	0.3618 (2)	0.0547 (8)
C5	0.1272 (2)	0.4126 (6)	0.2926 (3)	0.0556 (8)
H5	0.086 (2)	0.550 (5)	0.290 (2)	0.067*
C6	0.1896 (2)	0.3988 (5)	0.2296 (2)	0.0486 (7)
H6	0.193 (2)	0.523 (5)	0.182 (2)	0.058*
C7	0.3049 (2)	0.0071 (5)	0.0936 (2)	0.0484 (7)
C8	0.3859 (3)	0.0509 (7)	0.0415 (3)	0.0609 (9)
H8A	0.440 (2)	−0.074 (6)	0.068 (2)	0.073*
H8B	0.353 (2)	0.041 (6)	−0.037 (3)	0.073*
C9	0.4333 (3)	0.2887 (7)	0.0825 (3)	0.0631 (9)
H9A	0.510 (2)	0.288 (5)	0.109 (2)	0.076*
H9B	0.411 (2)	0.408 (6)	0.032 (2)	0.076*
C10	0.3921 (2)	0.3502 (5)	0.1706 (2)	0.0512 (7)
C11	0.0552 (3)	0.2544 (9)	0.4292 (3)	0.0859 (14)
H11A	−0.013 (3)	0.301 (7)	0.394 (3)	0.103*
H11B	0.085 (3)	0.350 (7)	0.492 (3)	0.103*
H11C	0.047 (3)	0.100 (7)	0.452 (3)	0.103*
N1	0.31460 (16)	0.1858 (4)	0.16839 (17)	0.0437 (6)
O1	0.24145 (17)	−0.1496 (4)	0.07658 (16)	0.0637 (6)
O2	0.41793 (16)	0.5111 (4)	0.23272 (19)	0.0714 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0456 (15)	0.0390 (15)	0.0363 (14)	−0.0054 (12)	0.0099 (12)	−0.0001 (12)
C2	0.0603 (19)	0.0461 (17)	0.0485 (17)	−0.0008 (15)	0.0121 (15)	0.0052 (15)
C3	0.076 (2)	0.059 (2)	0.0431 (17)	−0.0155 (18)	0.0166 (16)	0.0073 (16)
C4	0.0559 (17)	0.069 (2)	0.0411 (16)	−0.0183 (16)	0.0181 (14)	−0.0093 (16)
C5	0.0612 (19)	0.0545 (19)	0.0546 (18)	0.0017 (15)	0.0235 (16)	−0.0047 (16)
C6	0.0588 (18)	0.0438 (16)	0.0435 (17)	0.0016 (14)	0.0175 (14)	0.0057 (14)
C7	0.0562 (17)	0.0465 (16)	0.0396 (15)	0.0043 (15)	0.0119 (13)	−0.0003 (14)
C8	0.061 (2)	0.075 (2)	0.0497 (19)	0.0061 (17)	0.0223 (16)	0.0011 (18)
C9	0.0533 (18)	0.079 (3)	0.058 (2)	−0.0011 (18)	0.0192 (16)	0.0168 (19)
C10	0.0413 (15)	0.0518 (18)	0.0542 (18)	−0.0005 (14)	0.0071 (13)	0.0077 (16)
C11	0.081 (3)	0.123 (4)	0.063 (2)	−0.031 (3)	0.038 (2)	−0.019 (3)
N1	0.0451 (12)	0.0428 (13)	0.0436 (13)	−0.0032 (11)	0.0152 (10)	−0.0036 (11)
O1	0.0827 (15)	0.0526 (13)	0.0565 (13)	−0.0154 (12)	0.0239 (11)	−0.0110 (11)
O2	0.0679 (14)	0.0578 (14)	0.0843 (16)	−0.0163 (12)	0.0194 (12)	−0.0155 (13)

C1—C2	1.378 (4)	C7—N1	1.397 (3)
C1—C6	1.380 (4)	C7—C8	1.502 (4)
C1—N1	1.434 (3)	C8—C9	1.511 (5)
C2—C3	1.385 (4)	C8—H8A	0.99 (3)
C2—H2	0.96 (3)	C8—H8B	0.99 (3)
C3—C4	1.380 (4)	C9—C10	1.502 (4)
C3—H3	0.94 (3)	C9—H9A	0.99 (3)
C4—C5	1.381 (4)	C9—H9B	0.94 (3)
C4—C11	1.504 (5)	C10—O2	1.203 (3)
C5—C6	1.380 (4)	C10—N1	1.394 (3)
C5—H5	0.95 (3)	C11—H11A	0.92 (4)
C6—H6	0.95 (3)	C11—H11B	0.97 (4)
C7—O1	1.202 (3)	C11—H11C	0.95 (4)
C2—C1—C6	120.1 (3)	C9—C8—H8A	109.3 (18)
C2—C1—N1	120.5 (3)	C7—C8—H8B	109.8 (17)
C6—C1—N1	119.3 (2)	C9—C8—H8B	114.8 (19)
C1—C2—C3	119.2 (3)	H8A—C8—H8B	111 (3)
C1—C2—H2	119.0 (17)	C10—C9—C8	105.5 (3)
C3—C2—H2	121.7 (17)	C10—C9—H9A	110.0 (18)
C4—C3—C2	121.8 (3)	C8—C9—H9A	113.6 (19)
C4—C3—H3	120.0 (18)	C10—C9—H9B	106.7 (19)
C2—C3—H3	118.2 (19)	C8—C9—H9B	112.5 (19)
C3—C4—C5	117.6 (3)	H9A—C9—H9B	108 (3)
C3—C4—C11	122.2 (3)	O2—C10—N1	124.3 (3)
C5—C4—C11	120.3 (3)	O2—C10—C9	128.1 (3)
C6—C5—C4	121.7 (3)	N1—C10—C9	107.5 (3)
C6—C5—H5	119.5 (19)	C4—C11—H11A	116 (2)
C4—C5—H5	118.7 (18)	C4—C11—H11B	114 (2)
C1—C6—C5	119.5 (3)	H11A—C11—H11B	110 (3)
C1—C6—H6	118.4 (16)	C4—C11—H11C	106 (2)
C5—C6—H6	122.1 (17)	H11A—C11—H11C	103 (3)
O1—C7—N1	124.1 (3)	H11B—C11—H11C	107 (3)
O1—C7—C8	128.3 (3)	C10—N1—C7	112.9 (2)
N1—C7—C8	107.6 (3)	C10—N1—C1	123.4 (2)
C7—C8—C9	105.5 (3)	C7—N1—C1	123.7 (2)
C7—C8—H8A	106.5 (18)
C6—C1—C2—C3	−0.1 (4)	C8—C9—C10—N1	−9.4 (3)
N1—C1—C2—C3	−179.3 (3)	O2—C10—N1—C7	−175.6 (3)
C1—C2—C3—C4	0.1 (5)	C9—C10—N1—C7	5.1 (3)
C2—C3—C4—C5	−0.1 (5)	O2—C10—N1—C1	5.1 (4)
C2—C3—C4—C11	179.8 (3)	C9—C10—N1—C1	−174.2 (2)
C3—C4—C5—C6	−0.1 (5)	O1—C7—N1—C10	−178.2 (3)
C11—C4—C5—C6	−180.0 (3)	C8—C7—N1—C10	1.5 (3)
C2—C1—C6—C5	0.0 (4)	O1—C7—N1—C1	1.1 (4)
N1—C1—C6—C5	179.2 (3)	C8—C7—N1—C1	−179.2 (2)
C4—C5—C6—C1	0.1 (5)	C2—C1—N1—C10	−121.8 (3)
O1—C7—C8—C9	172.3 (3)	C6—C1—N1—C10	59.0 (3)
N1—C7—C8—C9	−7.4 (3)	C2—C1—N1—C7	59.0 (3)
C7—C8—C9—C10	10.1 (3)	C6—C1—N1—C7	−120.2 (3)
C8—C9—C10—O2	171.3 (3)