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N-Phenyl­succinamic acid

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 20 December 2010; accepted 21 December 2010; online 8 January 2011)

In the crystal structure of the title compound, C10H11NO3, the conformations of N—H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent –CH2 groups. The C=O and O—H bonds of the acid group are in syn positions with respect to each other. In the crystal, the mol­ecules are packed into infinite chains along the a axis through inter­molecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For our studies of the effect of substituents on the structures of anilides, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o399.], 2010a[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010a). Acta Cryst. E66, o842.],b[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010b). Acta Cryst. E66, o908.]). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]). For the packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994[Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75-78.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11NO3

  • Mr = 193.20

  • Monoclinic, P 21 /c

  • a = 4.986 (1) Å

  • b = 25.108 (4) Å

  • c = 7.895 (2) Å

  • β = 103.18 (2)°

  • V = 962.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.44 × 0.14 × 0.14 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.]) Tmin = 0.958, Tmax = 0.986

  • 3269 measured reflections

  • 1791 independent reflections

  • 1033 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.135

  • S = 0.99

  • 1791 reflections

  • 133 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.85 (2) 2.22 (2) 3.041 (3) 161 (2)
O3—H3O⋯O2ii 0.88 (2) 1.80 (2) 2.671 (2) 177 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of studying the effect of ring and side chain substitutions on the crystal structures of anilides (Gowda et al., 2009; 2010a,b), the crystal structure of N-(phenyl)succinamic acid (I) has been determined. The conformations of N—H and C=O bonds in the amide segment are anti to each other. The conformation of the amide oxygen and the carbonyl oxygen of the acid segment are also anti to each other, similar to that observed in N-(2-chlorophenyl)succinamic acid (II) (Gowda et al., 2009) and N-(2-methylphenyl)succinamic acid (III)(Gowda et al., 2010b), but contrary to the syn conformation observed in N-(3-methylphenyl)succinamic acid (IV) and N-(3-chlorophenyl)succinamic acid (V) (Gowda et al., 2010a). Further, the conformation of both the C=O bonds are anti to the H atoms of their adjacent –CH2 groups (Fig. 1) and the C=O and O—H bonds of the acid group are in syn position to each other, similar to that observed in (II), (III), (IV) and (V).

The N—H···O and O—H···O intermolecular hydrogen bonds pack the molecules into infinite chains in the structure (Table 1, Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Related literature top

For our study of the effect of substituents on the structures of anilides, see: Gowda et al. (2009, 2010a,b). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). For the packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994).

Experimental top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of aniline (0.01 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about one 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. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

Prism like colorless single crystals used in x-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement top

The H atoms of the NH and OH group were located in a difference map and later restrained to the distance N—H = 0.86 (2) Å and O—H = 0.82 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.97 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

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
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-Phenylsuccinamic acid top
Crystal data top
C10H11NO3F(000) = 408
Mr = 193.20Dx = 1.333 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 702 reflections
a = 4.986 (1) Åθ = 3.1–27.7°
b = 25.108 (4) ŵ = 0.10 mm1
c = 7.895 (2) ÅT = 293 K
β = 103.18 (2)°Prism, colorless
V = 962.3 (3) Å30.44 × 0.14 × 0.14 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
1791 independent reflections
Radiation source: fine-focus sealed tube1033 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Rotation method data acquisition using ω scansθmax = 25.7°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 56
Tmin = 0.958, Tmax = 0.986k = 3022
3269 measured reflectionsl = 79
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0703P)2]
where P = (Fo2 + 2Fc2)/3
1791 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.15 e Å3
2 restraintsΔρmin = 0.13 e Å3
Crystal data top
C10H11NO3V = 962.3 (3) Å3
Mr = 193.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.986 (1) ŵ = 0.10 mm1
b = 25.108 (4) ÅT = 293 K
c = 7.895 (2) Å0.44 × 0.14 × 0.14 mm
β = 103.18 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
1791 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1033 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.986Rint = 0.022
3269 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.15 e Å3
1791 reflectionsΔρmin = 0.13 e Å3
133 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3834 (4)0.31826 (10)0.9635 (3)0.0421 (6)
C20.1411 (5)0.33972 (11)0.8656 (3)0.0543 (7)
H20.00580.31770.80100.065*
C30.1030 (6)0.39415 (12)0.8651 (4)0.0649 (8)
H30.05890.40860.79890.078*
C40.2995 (6)0.42738 (12)0.9604 (4)0.0702 (9)
H40.27120.46400.95890.084*
C50.5378 (6)0.40589 (12)1.0577 (4)0.0697 (9)
H50.67200.42801.12290.084*
C60.5793 (5)0.35204 (11)1.0595 (3)0.0562 (7)
H60.74180.33791.12630.067*
C70.2674 (5)0.22230 (10)0.9613 (3)0.0448 (6)
C80.4033 (4)0.16836 (10)0.9852 (3)0.0484 (7)
H8A0.55750.16830.92930.058*
H8B0.47570.16221.10850.058*
C90.2123 (4)0.12352 (9)0.9121 (3)0.0504 (7)
H9A0.04990.12550.96010.060*
H9B0.15310.12800.78710.060*
C100.3391 (5)0.06985 (10)0.9496 (3)0.0491 (7)
N10.4434 (4)0.26322 (8)0.9654 (3)0.0483 (6)
H1N0.616 (3)0.2572 (10)0.983 (3)0.058*
O10.0199 (3)0.22839 (7)0.9463 (3)0.0677 (6)
O20.5739 (3)0.06282 (7)1.0309 (3)0.0701 (6)
O30.1737 (4)0.03061 (7)0.8868 (3)0.0728 (7)
H3O0.262 (5)0.0004 (8)0.913 (4)0.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0303 (11)0.0465 (16)0.0499 (15)0.0021 (11)0.0102 (10)0.0057 (12)
C20.0405 (14)0.0548 (18)0.0616 (17)0.0040 (12)0.0005 (12)0.0061 (14)
C30.0508 (16)0.063 (2)0.077 (2)0.0145 (15)0.0075 (14)0.0158 (17)
C40.070 (2)0.0465 (18)0.097 (2)0.0067 (16)0.0269 (17)0.0088 (17)
C50.0595 (19)0.052 (2)0.094 (2)0.0094 (15)0.0099 (16)0.0023 (17)
C60.0377 (13)0.0542 (18)0.072 (2)0.0007 (13)0.0018 (12)0.0006 (14)
C70.0301 (13)0.0461 (16)0.0578 (16)0.0006 (11)0.0089 (10)0.0025 (12)
C80.0288 (12)0.0505 (16)0.0640 (17)0.0025 (11)0.0064 (11)0.0015 (13)
C90.0330 (12)0.0470 (16)0.0667 (17)0.0044 (11)0.0020 (11)0.0003 (13)
C100.0344 (14)0.0473 (16)0.0619 (17)0.0001 (12)0.0037 (12)0.0007 (13)
N10.0241 (10)0.0463 (14)0.0721 (15)0.0022 (10)0.0057 (10)0.0010 (11)
O10.0252 (9)0.0548 (12)0.1239 (17)0.0050 (8)0.0184 (9)0.0050 (11)
O20.0411 (10)0.0472 (11)0.1055 (16)0.0068 (8)0.0175 (10)0.0023 (10)
O30.0426 (10)0.0436 (11)0.1161 (17)0.0035 (9)0.0156 (10)0.0047 (11)
Geometric parameters (Å, º) top
C1—C61.382 (3)C7—N11.347 (3)
C1—C21.386 (3)C7—C81.507 (3)
C1—N11.413 (3)C8—C91.503 (3)
C2—C31.380 (4)C8—H8A0.9700
C2—H20.9300C8—H8B0.9700
C3—C41.373 (4)C9—C101.489 (3)
C3—H30.9300C9—H9A0.9700
C4—C51.370 (4)C9—H9B0.9700
C4—H40.9300C10—O21.213 (3)
C5—C61.367 (4)C10—O31.308 (3)
C5—H50.9300N1—H1N0.852 (16)
C6—H60.9300O3—H3O0.877 (17)
C7—O11.222 (3)
C6—C1—C2119.0 (2)N1—C7—C8114.25 (19)
C6—C1—N1118.2 (2)C9—C8—C7113.43 (18)
C2—C1—N1122.8 (2)C9—C8—H8A108.9
C3—C2—C1119.2 (2)C7—C8—H8A108.9
C3—C2—H2120.4C9—C8—H8B108.9
C1—C2—H2120.4C7—C8—H8B108.9
C4—C3—C2121.3 (3)H8A—C8—H8B107.7
C4—C3—H3119.3C10—C9—C8113.48 (19)
C2—C3—H3119.3C10—C9—H9A108.9
C5—C4—C3119.1 (3)C8—C9—H9A108.9
C5—C4—H4120.4C10—C9—H9B108.9
C3—C4—H4120.4C8—C9—H9B108.9
C6—C5—C4120.4 (3)H9A—C9—H9B107.7
C6—C5—H5119.8O2—C10—O3122.7 (2)
C4—C5—H5119.8O2—C10—C9123.5 (2)
C5—C6—C1121.0 (2)O3—C10—C9113.83 (19)
C5—C6—H6119.5C7—N1—C1127.64 (19)
C1—C6—H6119.5C7—N1—H1N119.7 (18)
O1—C7—N1123.0 (2)C1—N1—H1N112.3 (18)
O1—C7—C8122.7 (2)C10—O3—H3O108.8 (19)
C6—C1—C2—C30.7 (4)N1—C7—C8—C9157.0 (2)
N1—C1—C2—C3177.3 (2)C7—C8—C9—C10174.8 (2)
C1—C2—C3—C40.4 (5)C8—C9—C10—O20.1 (4)
C2—C3—C4—C50.0 (5)C8—C9—C10—O3179.8 (2)
C3—C4—C5—C60.1 (5)O1—C7—N1—C13.7 (4)
C4—C5—C6—C10.1 (4)C8—C7—N1—C1173.5 (2)
C2—C1—C6—C50.5 (4)C6—C1—N1—C7144.5 (3)
N1—C1—C6—C5177.5 (2)C2—C1—N1—C737.5 (4)
O1—C7—C8—C925.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (2)2.22 (2)3.041 (3)161 (2)
O3—H3O···O2ii0.88 (2)1.80 (2)2.671 (2)177 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC10H11NO3
Mr193.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)4.986 (1), 25.108 (4), 7.895 (2)
β (°) 103.18 (2)
V3)962.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.44 × 0.14 × 0.14
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.958, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
3269, 1791, 1033
Rint0.022
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.135, 0.99
No. of reflections1791
No. of parameters133
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.13

Computer programs: CrysAlis CCD (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···AD—HH···AD···AD—H···A
N1—H1N···O1i0.852 (16)2.221 (18)3.041 (3)161 (2)
O3—H3O···O2ii0.877 (17)1.795 (18)2.671 (2)177 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+2.
 

Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

First citationGowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010a). Acta Cryst. E66, o842.  Web of Science CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010b). Acta Cryst. E66, o908.  Web of Science CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o399.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationJagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75–78.  CSD CrossRef CAS Web of Science Google Scholar
First citationLeiserowitz, L. (1976). Acta Cryst. B32, 775–802.  CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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