Methyl N-phenyl-succinamate.

In the structure of the title compound, C(11)H(13)NO(3), the conformations of the N-H and C=O bonds in the amide fragment are trans to each other. In the crystal, mol-ecules are linked into a 2(1) helical chain that propagates along the c axis through N-H⋯O inter-actions.

Related literature

For related structures, see: Gowda et al. (2007 ▶, 2009 ▶); Jones et al. (1990 ▶).

Experimental

Crystal data

C11H13NO3

M = 207.22

Orthorhombic,

a = 15.973 (2) Å

b = 12.600 (1) Å

c = 5.2438 (9) Å

V = 1055.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 299 K

0.50 × 0.12 × 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 = 0.954, T max = 0.992

2584 measured reflections

1184 independent reflections

774 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.096

S = 1.13

1184 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.11 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/S160053680904690X/pk2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904690X/pk2203Isup2.hkl

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

C11H13NO3	F(000) = 440
Mr = 207.22	Dx = 1.304 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 930 reflections
a = 15.973 (2) Å	θ = 2.6–27.5°
b = 12.600 (1) Å	µ = 0.10 mm−1
c = 5.2438 (9) Å	T = 299 K
V = 1055.4 (2) Å3	Rod, colourless
Z = 4	0.50 × 0.12 × 0.08 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1184 independent reflections
Radiation source: fine-focus sealed tube	774 reflections with I > 2σ(I)
graphite	Rint = 0.023
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −19→16
Tmin = 0.954, Tmax = 0.992	k = −10→15
2584 measured reflections	l = −6→5

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.1073P] where P = (Fo2 + 2Fc2)/3
1184 reflections	(Δ/σ)max = 0.032
140 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.11 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 > 2σ(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
O1	0.12956 (15)	0.16946 (18)	0.1342 (6)	0.0713 (7)
O2	0.13057 (14)	−0.08851 (18)	0.1486 (6)	0.0664 (7)
O3	0.26104 (16)	−0.09216 (19)	−0.0009 (6)	0.0751 (8)
N1	−0.00368 (18)	0.1938 (2)	−0.0025 (7)	0.0556 (8)
H1N	−0.039 (2)	0.171 (3)	−0.112 (7)	0.067*
C1	−0.03455 (19)	0.2709 (2)	0.1695 (7)	0.0465 (8)
C2	−0.1192 (2)	0.2940 (3)	0.1633 (9)	0.0629 (10)
H2	−0.1534	0.2593	0.0466	0.076*
C3	−0.1535 (2)	0.3670 (3)	0.3259 (10)	0.0702 (11)
H3	−0.2105	0.3815	0.3178	0.084*
C4	−0.1043 (3)	0.4192 (3)	0.5015 (10)	0.0676 (10)
H4	−0.1278	0.4675	0.6148	0.081*
C5	−0.0201 (3)	0.3984 (3)	0.5061 (10)	0.0692 (10)
H5	0.0139	0.4339	0.6222	0.083*
C6	0.0152 (2)	0.3251 (3)	0.3392 (8)	0.0619 (10)
H6	0.0726	0.3127	0.3426	0.074*
C7	0.0728 (2)	0.1478 (2)	−0.0132 (8)	0.0499 (8)
C8	0.0820 (2)	0.0666 (3)	−0.2223 (7)	0.0602 (10)
H8A	0.0730	0.1009	−0.3856	0.072*
H8B	0.0391	0.0128	−0.2016	0.072*
C9	0.1666 (2)	0.0136 (3)	−0.2240 (7)	0.0629 (10)
H9A	0.1726	−0.0260	−0.3817	0.076*
H9B	0.2096	0.0681	−0.2224	0.076*
C10	0.1815 (2)	−0.0602 (2)	−0.0043 (8)	0.0528 (9)
C11	0.2848 (2)	−0.1655 (3)	0.2016 (10)	0.0906 (16)
H11A	0.2554	−0.2313	0.1799	0.136*
H11B	0.2708	−0.1353	0.3640	0.136*
H11C	0.3440	−0.1783	0.1941	0.136*

	U11	U22	U33	U12	U13	U23
O1	0.0574 (14)	0.0822 (16)	0.0745 (17)	0.0086 (12)	−0.0170 (17)	−0.0237 (19)
O2	0.0594 (14)	0.0779 (16)	0.0619 (15)	0.0023 (13)	0.0225 (17)	0.0105 (18)
O3	0.0616 (17)	0.0773 (16)	0.0863 (18)	0.0099 (13)	0.0306 (18)	0.0165 (19)
N1	0.0538 (19)	0.0599 (17)	0.0530 (18)	−0.0006 (14)	−0.0167 (17)	−0.0114 (19)
C1	0.055 (2)	0.0429 (17)	0.0418 (18)	0.0002 (16)	−0.004 (2)	0.0039 (19)
C2	0.053 (2)	0.067 (2)	0.069 (2)	−0.0030 (18)	−0.010 (3)	−0.002 (3)
C3	0.057 (3)	0.072 (3)	0.081 (3)	0.0072 (19)	0.005 (3)	0.004 (3)
C4	0.076 (3)	0.065 (2)	0.062 (2)	0.011 (2)	0.008 (3)	−0.003 (3)
C5	0.081 (3)	0.065 (2)	0.061 (2)	0.005 (2)	−0.016 (3)	−0.015 (2)
C6	0.059 (2)	0.063 (2)	0.064 (2)	0.0056 (18)	−0.016 (2)	−0.008 (2)
C7	0.056 (2)	0.0482 (18)	0.0455 (19)	−0.0040 (17)	0.000 (2)	0.001 (2)
C8	0.072 (2)	0.064 (2)	0.045 (2)	−0.0006 (19)	0.001 (2)	−0.003 (2)
C9	0.075 (2)	0.067 (2)	0.047 (2)	−0.003 (2)	0.018 (2)	−0.004 (2)
C10	0.057 (2)	0.0481 (18)	0.053 (2)	−0.0006 (17)	0.018 (2)	−0.008 (2)
C11	0.073 (3)	0.093 (3)	0.106 (4)	0.022 (2)	0.024 (3)	0.022 (3)

O1—C7	1.222 (4)	C4—H4	0.9300
O2—C10	1.196 (4)	C5—C6	1.393 (5)
O3—C10	1.333 (4)	C5—H5	0.9300
O3—C11	1.458 (5)	C6—H6	0.9300
N1—C7	1.354 (4)	C7—C8	1.507 (5)
N1—C1	1.415 (4)	C8—C9	1.508 (5)
N1—H1N	0.85 (4)	C8—H8A	0.9700
C1—C6	1.375 (4)	C8—H8B	0.9700
C1—C2	1.383 (4)	C9—C10	1.500 (5)
C2—C3	1.369 (5)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.377 (6)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.370 (5)	C11—H11C	0.9600
C10—O3—C11	116.7 (3)	O1—C7—C8	122.7 (3)
C7—N1—C1	129.4 (3)	N1—C7—C8	114.1 (3)
C7—N1—H1N	115 (2)	C7—C8—C9	113.1 (3)
C1—N1—H1N	115 (2)	C7—C8—H8A	109.0
C6—C1—C2	118.4 (3)	C9—C8—H8A	109.0
C6—C1—N1	123.5 (3)	C7—C8—H8B	109.0
C2—C1—N1	118.0 (3)	C9—C8—H8B	109.0
C3—C2—C1	121.2 (4)	H8A—C8—H8B	107.8
C3—C2—H2	119.4	C10—C9—C8	114.3 (3)
C1—C2—H2	119.4	C10—C9—H9A	108.7
C2—C3—C4	120.6 (4)	C8—C9—H9A	108.7
C2—C3—H3	119.7	C10—C9—H9B	108.7
C4—C3—H3	119.7	C8—C9—H9B	108.7
C5—C4—C3	118.7 (4)	H9A—C9—H9B	107.6
C5—C4—H4	120.6	O2—C10—O3	123.3 (4)
C3—C4—H4	120.6	O2—C10—C9	126.3 (3)
C4—C5—C6	120.9 (4)	O3—C10—C9	110.4 (3)
C4—C5—H5	119.5	O3—C11—H11A	109.5
C6—C5—H5	119.5	O3—C11—H11B	109.5
C1—C6—C5	120.1 (3)	H11A—C11—H11B	109.5
C1—C6—H6	120.0	O3—C11—H11C	109.5
C5—C6—H6	120.0	H11A—C11—H11C	109.5
O1—C7—N1	123.2 (4)	H11B—C11—H11C	109.5
C7—N1—C1—C6	10.3 (6)	C1—N1—C7—O1	−0.8 (6)
C7—N1—C1—C2	−170.7 (4)	C1—N1—C7—C8	178.8 (3)
C6—C1—C2—C3	−1.6 (6)	O1—C7—C8—C9	1.7 (5)
N1—C1—C2—C3	179.4 (4)	N1—C7—C8—C9	−177.9 (3)
C1—C2—C3—C4	−0.3 (6)	C7—C8—C9—C10	70.2 (4)
C2—C3—C4—C5	1.6 (6)	C11—O3—C10—O2	0.2 (5)
C3—C4—C5—C6	−0.9 (6)	C11—O3—C10—C9	−179.4 (3)
C2—C1—C6—C5	2.2 (5)	C8—C9—C10—O2	8.9 (5)
N1—C1—C6—C5	−178.8 (4)	C8—C9—C10—O3	−171.5 (3)
C4—C5—C6—C1	−1.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (4)	2.20 (4)	3.036 (4)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (4)	2.20 (4)	3.036 (4)	170 (3)

Symmetry code: (i) .