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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3064.
Published online 2009 November 11. doi:  10.1107/S160053680904690X
PMCID: PMC2971872

Methyl N-phenyl­succinamate

Abstract

In the structure of the title compound, C11H13NO3, the conformations of the N—H and C=O bonds in the amide fragment are trans to each other. In the crystal, mol­ecules are linked into a 21 helical chain that propagates along the c axis through N—H(...)O inter­actions.

Related literature

For related structures, see: Gowda et al. (2007 [triangle], 2009a [triangle],b [triangle]); Jones et al. (1990 [triangle]).

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Object name is e-65-o3064-scheme1.jpg

Experimental

Crystal data

  • C11H13NO3
  • M r = 207.22
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3064-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

Amides are of interest as conjugation between the nitrogen lone pair electrons and the carbonyl π-bond results in distinct physical and chemical properties. The amide moiety is also an important constituent of many biologically significant compounds. Thus the structural studies of amides are of interest see Gowda et al., 2007, and references therein, 2009a,b; Jones et al., 1990; as representative examples. As a part of studying the effect of ring and side chain substitutions on the solid state geometry of this class of compounds, we report herein the crystal structure of N-(phenyl)methylsuccinamate. The conformations of the N—H and C=O bonds in the amide fragment are trans to each other (Fig. 1). The side chain in the title compound is bent at C8 with C7—C8—C9—C10 torsional angle of 70.3 (4)°. The linking of molecules into a helical chain by N—H···O interactions (Table 1) is shown in Fig.2.

Experimental

A solution of succinic anhydride (0.025 mole) in toluene (25 ml) was treated dropwise with a solution of aniline (0.025 mole) in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 1 h and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted aniline. The resultant solid N-(phenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid and was recrystallized from methanol. The recrystallized sample in methanol (20 ml) was treated with concentrated sulfuric acid (2 ml). The mixture was refluxed for 2 h and kept for slow evaporation at room temperature to obtain crystals of N-(phenyl)methylsuccinamate. The crystals were washed with water to remove sulfuric acid and dried. The purity of the compound was checked by elemental analysis and characterized by recording its infrared spectra. The single crystals used in X-ray diffraction studies were grown from methanolic solution by slow evaporation at room temperature.

Refinement

The H atom of the NH group was located in a difference map and its position refined with N—H = 0.85 (4) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.97 Å. Isotropic displacement parameters for the H atoms of the methyl group were set to 1.5 Ueq (parent atom), for the other H atoms equal to 1.2 Ueq (parent atom).

In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf" terms set to zero.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radius.
Fig. 2.
Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Crystal data

C11H13NO3F(000) = 440
Mr = 207.22Dx = 1.304 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 930 reflections
a = 15.973 (2) Åθ = 2.6–27.5°
b = 12.600 (1) ŵ = 0.10 mm1
c = 5.2438 (9) ÅT = 299 K
V = 1055.4 (2) Å3Rod, colourless
Z = 40.50 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector1184 independent reflections
Radiation source: fine-focus sealed tube774 reflections with I > 2σ(I)
graphiteRint = 0.023
Rotation method data acquisition using ω and [var phi] scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −19→16
Tmin = 0.954, Tmax = 0.992k = −10→15
2584 measured reflectionsl = −6→5

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.0356P)2 + 0.1073P] where P = (Fo2 + 2Fc2)/3
1184 reflections(Δ/σ)max = 0.032
140 parametersΔρmax = 0.11 e Å3
1 restraintΔρmin = −0.11 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.12956 (15)0.16946 (18)0.1342 (6)0.0713 (7)
O20.13057 (14)−0.08851 (18)0.1486 (6)0.0664 (7)
O30.26104 (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)
H2−0.15340.25930.04660.076*
C3−0.1535 (2)0.3670 (3)0.3259 (10)0.0702 (11)
H3−0.21050.38150.31780.084*
C4−0.1043 (3)0.4192 (3)0.5015 (10)0.0676 (10)
H4−0.12780.46750.61480.081*
C5−0.0201 (3)0.3984 (3)0.5061 (10)0.0692 (10)
H50.01390.43390.62220.083*
C60.0152 (2)0.3251 (3)0.3392 (8)0.0619 (10)
H60.07260.31270.34260.074*
C70.0728 (2)0.1478 (2)−0.0132 (8)0.0499 (8)
C80.0820 (2)0.0666 (3)−0.2223 (7)0.0602 (10)
H8A0.07300.1009−0.38560.072*
H8B0.03910.0128−0.20160.072*
C90.1666 (2)0.0136 (3)−0.2240 (7)0.0629 (10)
H9A0.1726−0.0260−0.38170.076*
H9B0.20960.0681−0.22240.076*
C100.1815 (2)−0.0602 (2)−0.0043 (8)0.0528 (9)
C110.2848 (2)−0.1655 (3)0.2016 (10)0.0906 (16)
H11A0.2554−0.23130.17990.136*
H11B0.2708−0.13530.36400.136*
H11C0.3440−0.17830.19410.136*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0574 (14)0.0822 (16)0.0745 (17)0.0086 (12)−0.0170 (17)−0.0237 (19)
O20.0594 (14)0.0779 (16)0.0619 (15)0.0023 (13)0.0225 (17)0.0105 (18)
O30.0616 (17)0.0773 (16)0.0863 (18)0.0099 (13)0.0306 (18)0.0165 (19)
N10.0538 (19)0.0599 (17)0.0530 (18)−0.0006 (14)−0.0167 (17)−0.0114 (19)
C10.055 (2)0.0429 (17)0.0418 (18)0.0002 (16)−0.004 (2)0.0039 (19)
C20.053 (2)0.067 (2)0.069 (2)−0.0030 (18)−0.010 (3)−0.002 (3)
C30.057 (3)0.072 (3)0.081 (3)0.0072 (19)0.005 (3)0.004 (3)
C40.076 (3)0.065 (2)0.062 (2)0.011 (2)0.008 (3)−0.003 (3)
C50.081 (3)0.065 (2)0.061 (2)0.005 (2)−0.016 (3)−0.015 (2)
C60.059 (2)0.063 (2)0.064 (2)0.0056 (18)−0.016 (2)−0.008 (2)
C70.056 (2)0.0482 (18)0.0455 (19)−0.0040 (17)0.000 (2)0.001 (2)
C80.072 (2)0.064 (2)0.045 (2)−0.0006 (19)0.001 (2)−0.003 (2)
C90.075 (2)0.067 (2)0.047 (2)−0.003 (2)0.018 (2)−0.004 (2)
C100.057 (2)0.0481 (18)0.053 (2)−0.0006 (17)0.018 (2)−0.008 (2)
C110.073 (3)0.093 (3)0.106 (4)0.022 (2)0.024 (3)0.022 (3)

Geometric parameters (Å, °)

O1—C71.222 (4)C4—H40.9300
O2—C101.196 (4)C5—C61.393 (5)
O3—C101.333 (4)C5—H50.9300
O3—C111.458 (5)C6—H60.9300
N1—C71.354 (4)C7—C81.507 (5)
N1—C11.415 (4)C8—C91.508 (5)
N1—H1N0.85 (4)C8—H8A0.9700
C1—C61.375 (4)C8—H8B0.9700
C1—C21.383 (4)C9—C101.500 (5)
C2—C31.369 (5)C9—H9A0.9700
C2—H20.9300C9—H9B0.9700
C3—C41.377 (6)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—C51.370 (5)C11—H11C0.9600
C10—O3—C11116.7 (3)O1—C7—C8122.7 (3)
C7—N1—C1129.4 (3)N1—C7—C8114.1 (3)
C7—N1—H1N115 (2)C7—C8—C9113.1 (3)
C1—N1—H1N115 (2)C7—C8—H8A109.0
C6—C1—C2118.4 (3)C9—C8—H8A109.0
C6—C1—N1123.5 (3)C7—C8—H8B109.0
C2—C1—N1118.0 (3)C9—C8—H8B109.0
C3—C2—C1121.2 (4)H8A—C8—H8B107.8
C3—C2—H2119.4C10—C9—C8114.3 (3)
C1—C2—H2119.4C10—C9—H9A108.7
C2—C3—C4120.6 (4)C8—C9—H9A108.7
C2—C3—H3119.7C10—C9—H9B108.7
C4—C3—H3119.7C8—C9—H9B108.7
C5—C4—C3118.7 (4)H9A—C9—H9B107.6
C5—C4—H4120.6O2—C10—O3123.3 (4)
C3—C4—H4120.6O2—C10—C9126.3 (3)
C4—C5—C6120.9 (4)O3—C10—C9110.4 (3)
C4—C5—H5119.5O3—C11—H11A109.5
C6—C5—H5119.5O3—C11—H11B109.5
C1—C6—C5120.1 (3)H11A—C11—H11B109.5
C1—C6—H6120.0O3—C11—H11C109.5
C5—C6—H6120.0H11A—C11—H11C109.5
O1—C7—N1123.2 (4)H11B—C11—H11C109.5
C7—N1—C1—C610.3 (6)C1—N1—C7—O1−0.8 (6)
C7—N1—C1—C2−170.7 (4)C1—N1—C7—C8178.8 (3)
C6—C1—C2—C3−1.6 (6)O1—C7—C8—C91.7 (5)
N1—C1—C2—C3179.4 (4)N1—C7—C8—C9−177.9 (3)
C1—C2—C3—C4−0.3 (6)C7—C8—C9—C1070.2 (4)
C2—C3—C4—C51.6 (6)C11—O3—C10—O20.2 (5)
C3—C4—C5—C6−0.9 (6)C11—O3—C10—C9−179.4 (3)
C2—C1—C6—C52.2 (5)C8—C9—C10—O28.9 (5)
N1—C1—C6—C5−178.8 (4)C8—C9—C10—O3−171.5 (3)
C4—C5—C6—C1−1.0 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.85 (4)2.20 (4)3.036 (4)170 (3)

Symmetry codes: (i) −x, −y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2203).

References

  • Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009a). Acta Cryst. E65, o1827. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o388. [PMC free article] [PubMed]
  • Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100.
  • Jones, P. G., Kirby, A. J. & Lewis, R. J. (1990). Acta Cryst. C46, 78–81.
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography