Methyl N-phenyl­succinamate

Gowda, B.T.; Foro, S.; Saraswathi, B.S.; Fuess, H.

doi:10.1107/S160053680904690X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3064

doi:10.1107/S160053680904690X

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Methyl N-phenylsuccinamate

B. Thimme Gowda,^a ^* Sabine Foro,^b B. S. Saraswathi ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 14 October 2009; accepted 6 November 2009; online 11 November 2009)

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 , 2009a ,b ); Jones et al. (1990 ).

Experimental

Crystal data

C₁₁H₁₃NO₃
M_r = 207.22
Orthorhombic, P n a 2₁
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.096
S = 1.13
1184 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.11 e Å⁻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) $[-x, -y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904690X/pk2203sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	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.

Methyl N-phenylsuccinamate top

Crystal data top

C₁₁H₁₃NO₃	F(000) = 440
M_r = 207.22	D_x = 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

Data collection top

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 monochromator	R_int = 0.023
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −19→16
T_min = 0.954, T_max = 0.992	k = −10→15
2584 measured reflections	l = −6→5

Refinement top

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(F_o²) + (0.0356P)² + 0.1073P] where P = (F_o² + 2F_c²)/3
1184 reflections	(Δ/σ)_max = 0.032
140 parameters	Δρ_max = 0.11 e Å⁻³
1 restraint	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₁H₁₃NO₃	V = 1055.4 (2) Å³
M_r = 207.22	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 15.973 (2) Å	µ = 0.10 mm⁻¹
b = 12.600 (1) Å	T = 299 K
c = 5.2438 (9) Å	0.50 × 0.12 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1184 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	774 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.992	R_int = 0.023
2584 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.11 e Å⁻³
1184 reflections	Δρ_min = −0.11 e Å⁻³
140 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₃
M_r	207.22
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	299
a, b, c (Å)	15.973 (2), 12.600 (1), 5.2438 (9)
V (Å³)	1055.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.12 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.954, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	2584, 1184, 774
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.096, 1.13
No. of reflections	1184
No. of parameters	140
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.11

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y, z−1/2.

Acknowledgements

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

References

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