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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1101.
Published online 2009 April 25. doi:  10.1107/S1600536809014627
PMCID: PMC2977779

N-Phenyl­maleamic acid

Abstract

The two independent mol­ecules in the title compound (systematic name: 4-amino-4-oxobut-2-enoic acid), C10H9NO3, are both essentially planar (r.m.s. deviations = 0.05 and 0.06 Å). In both mol­ecules, the –OH group forms an intra­molecular hydrogen bond to the amide O atom. Adjacent mol­ecules are linked by N—H(...)O hydrogen bonds into a flat ribbon that runs along the a axis of the monoclinic unit cell.

Related literature

For the crystal structures of other substituted N-(phen­yl)maleamic acids, see, for example: Gonzalez-Rodriguez et al. (1986 [triangle]); Home et al. (1991 [triangle]); Lynch & McClenaghan (2002 [triangle]); Parvez et al. (2004a [triangle],b [triangle]); Prasad et al. (2002a [triangle],b [triangle]); Santos-Sánchez et al. (2007 [triangle]); Wardell et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1101-scheme1.jpg

Experimental

Crystal data

  • C10H9NO3
  • M r = 191.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1101-efi1.jpg
  • a = 12.7505 (4) Å
  • b = 10.5849 (5) Å
  • c = 14.1918 (6) Å
  • β = 116.299 (3)°
  • V = 1717.1 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.24 × 0.06 × 0.06 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 11493 measured reflections
  • 3925 independent reflections
  • 2256 reflections with I > 2σ(I)
  • R int = 0.062

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.208
  • S = 1.02
  • 3925 reflections
  • 269 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.96 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014627/tk2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014627/tk2436Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (FS339/2008 A) for supporting this study.

supplementary crystallographic information

Experimental

Maleic anhydride (1 g, 1 mmol) and aniline (1 ml, 1 mmol) was heated in toluene (50 ml) for 1 h. The solution was set aside for the formation of crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The oxygen- and nitrogen-bound hydrogen atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 Å and N–H 0.88±0.01 Å; the temperature factors were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C10H9NO3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H9NO3F(000) = 800
Mr = 191.18Dx = 1.479 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1202 reflections
a = 12.7505 (4) Åθ = 2.6–27.4°
b = 10.5849 (5) ŵ = 0.11 mm1
c = 14.1918 (6) ÅT = 100 K
β = 116.299 (3)°Prism, colorless
V = 1717.1 (1) Å30.24 × 0.06 × 0.06 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer2256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
graphiteθmax = 27.5°, θmin = 1.8°
ω scansh = −16→16
11493 measured reflectionsk = −13→13
3925 independent reflectionsl = −14→18

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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.1139P)2] where P = (Fo2 + 2Fc2)/3
3925 reflections(Δ/σ)max = 0.001
269 parametersΔρmax = 0.96 e Å3
4 restraintsΔρmin = −0.36 e Å3

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

xyzUiso*/Ueq
O10.41604 (16)0.86211 (19)0.61750 (16)0.0173 (5)
O20.41080 (17)0.6545 (2)0.62972 (17)0.0167 (5)
H2O0.449 (3)0.590 (3)0.627 (3)0.058 (14)*
O30.53761 (17)0.4779 (2)0.62899 (16)0.0187 (5)
O40.91395 (17)0.5468 (2)0.60999 (17)0.0216 (5)
O50.91031 (17)0.75293 (19)0.62870 (17)0.0164 (5)
H5O0.946 (3)0.820 (2)0.625 (3)0.028 (10)*
O61.03470 (16)0.93320 (19)0.62520 (16)0.0187 (5)
N10.7136 (2)0.4490 (2)0.62704 (18)0.0122 (5)
H1N0.771 (2)0.492 (3)0.623 (2)0.019 (8)*
N21.2093 (2)0.9624 (2)0.62037 (19)0.0149 (6)
H2N1.2657 (19)0.923 (3)0.611 (2)0.020 (8)*
C10.4591 (2)0.7584 (3)0.6178 (2)0.0123 (6)
C20.5691 (2)0.7538 (3)0.6046 (2)0.0109 (6)
H20.59330.83360.59060.013*
C30.6396 (2)0.6584 (3)0.6087 (2)0.0157 (6)
H30.70790.68110.60180.019*
C40.6250 (2)0.5224 (3)0.6227 (2)0.0135 (6)
C50.7229 (2)0.3155 (3)0.6348 (2)0.0130 (6)
C60.8169 (2)0.2612 (3)0.6232 (2)0.0118 (6)
H60.87100.31390.61250.014*
C70.8311 (2)0.1321 (3)0.6272 (2)0.0164 (6)
H70.89450.09570.61880.020*
C80.7521 (2)0.0547 (3)0.6436 (2)0.0149 (6)
H80.7609−0.03450.64500.018*
C90.6615 (2)0.1075 (3)0.6576 (2)0.0171 (6)
H90.60860.05440.66970.020*
C100.6463 (2)0.2388 (3)0.6541 (2)0.0136 (6)
H100.58430.27490.66480.016*
C110.9577 (2)0.6509 (3)0.6128 (2)0.0145 (6)
C121.0671 (2)0.6566 (3)0.5988 (2)0.0171 (6)
H121.09100.57730.58360.021*
C131.1380 (2)0.7531 (3)0.6038 (2)0.0095 (6)
H131.20700.73130.59770.011*
C141.1215 (2)0.8896 (3)0.6177 (2)0.0140 (6)
C151.2203 (2)1.0966 (3)0.6289 (2)0.0130 (6)
C161.3130 (2)1.1490 (3)0.6154 (2)0.0169 (7)
H161.36451.09610.60120.020*
C171.3298 (2)1.2781 (3)0.6228 (2)0.0163 (6)
H171.39341.31360.61430.020*
C181.2542 (2)1.3569 (3)0.6427 (2)0.0165 (6)
H181.26591.44580.64710.020*
C191.1619 (2)1.3044 (3)0.6560 (2)0.0147 (6)
H191.10971.35760.66890.018*
C201.1457 (2)1.1746 (3)0.6504 (2)0.0147 (6)
H201.08351.13880.66120.018*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0154 (10)0.0149 (12)0.0241 (12)0.0036 (8)0.0111 (9)−0.0025 (9)
O20.0143 (10)0.0118 (12)0.0283 (12)0.0004 (9)0.0133 (9)0.0026 (9)
O30.0165 (10)0.0144 (12)0.0298 (12)−0.0003 (8)0.0145 (9)0.0015 (9)
O40.0195 (10)0.0149 (12)0.0335 (13)−0.0042 (9)0.0145 (10)−0.0003 (9)
O50.0150 (10)0.0108 (12)0.0280 (13)−0.0026 (8)0.0138 (9)0.0000 (9)
O60.0176 (10)0.0126 (12)0.0322 (13)−0.0003 (9)0.0166 (9)−0.0029 (9)
N10.0159 (12)0.0072 (13)0.0159 (12)−0.0001 (10)0.0091 (10)0.0012 (10)
N20.0145 (12)0.0157 (14)0.0175 (13)0.0013 (10)0.0097 (10)0.0010 (10)
C10.0106 (13)0.0144 (16)0.0125 (15)0.0004 (11)0.0057 (11)−0.0015 (11)
C20.0111 (13)0.0083 (15)0.0136 (14)−0.0008 (10)0.0057 (11)−0.0022 (11)
C30.0166 (13)0.0157 (17)0.0185 (15)−0.0007 (12)0.0112 (12)−0.0009 (12)
C40.0135 (13)0.0150 (16)0.0128 (14)0.0017 (11)0.0067 (11)−0.0012 (11)
C50.0149 (13)0.0136 (15)0.0106 (14)0.0022 (12)0.0056 (11)0.0007 (12)
C60.0127 (13)0.0119 (15)0.0128 (14)−0.0023 (11)0.0075 (11)0.0004 (11)
C70.0161 (13)0.0162 (17)0.0165 (15)0.0017 (12)0.0068 (12)−0.0009 (12)
C80.0231 (14)0.0050 (14)0.0177 (15)−0.0012 (11)0.0101 (12)−0.0002 (11)
C90.0166 (13)0.0175 (17)0.0171 (15)−0.0020 (12)0.0075 (12)0.0044 (12)
C100.0094 (12)0.0195 (17)0.0122 (15)0.0029 (11)0.0049 (11)0.0005 (12)
C110.0151 (13)0.0139 (16)0.0159 (15)0.0000 (12)0.0082 (12)0.0018 (12)
C120.0197 (14)0.0182 (17)0.0175 (15)0.0032 (12)0.0119 (12)0.0005 (12)
C130.0114 (12)0.0100 (14)0.0075 (13)0.0000 (10)0.0044 (10)−0.0009 (10)
C140.0176 (13)0.0158 (16)0.0091 (14)0.0013 (12)0.0064 (11)0.0009 (11)
C150.0176 (13)0.0107 (15)0.0084 (13)0.0042 (11)0.0037 (11)0.0025 (11)
C160.0171 (14)0.0180 (17)0.0167 (15)0.0033 (12)0.0083 (12)0.0000 (12)
C170.0105 (13)0.0211 (17)0.0164 (15)−0.0028 (12)0.0051 (11)0.0027 (13)
C180.0173 (14)0.0139 (16)0.0154 (15)−0.0052 (12)0.0046 (12)−0.0002 (12)
C190.0135 (13)0.0141 (16)0.0155 (15)−0.0006 (12)0.0057 (11)−0.0011 (12)
C200.0159 (13)0.0149 (15)0.0136 (15)0.0020 (12)0.0069 (11)0.0005 (12)

Geometric parameters (Å, °)

O1—C11.227 (3)C7—C81.395 (4)
O2—C11.307 (3)C7—H70.9500
O2—H2O0.846 (10)C8—C91.375 (4)
O3—C41.249 (3)C8—H80.9500
O4—C111.227 (3)C9—C101.401 (4)
O5—C111.305 (3)C9—H90.9500
O5—H5O0.857 (10)C10—H100.9500
O6—C141.247 (3)C11—C121.495 (4)
N1—C41.350 (3)C12—C131.344 (4)
N1—C51.419 (4)C12—H120.9500
N1—H1N0.879 (10)C13—C141.486 (4)
N2—C141.345 (4)C13—H130.9500
N2—C151.427 (4)C15—C201.391 (4)
N2—H2N0.886 (10)C15—C161.394 (4)
C1—C21.496 (4)C16—C171.379 (4)
C2—C31.335 (4)C16—H160.9500
C2—H20.9500C17—C181.394 (4)
C3—C41.476 (4)C17—H170.9500
C3—H30.9500C18—C191.389 (4)
C5—C101.387 (4)C18—H180.9500
C5—C61.403 (4)C19—C201.387 (4)
C6—C71.377 (4)C19—H190.9500
C6—H60.9500C20—H200.9500
C1—O2—H2O111 (3)C10—C9—H9119.7
C11—O5—H5O112 (2)C5—C10—C9119.3 (3)
C4—N1—C5128.0 (2)C5—C10—H10120.3
C4—N1—H1N114 (2)C9—C10—H10120.3
C5—N1—H1N118 (2)O4—C11—O5120.7 (2)
C14—N2—C15128.4 (2)O4—C11—C12118.0 (3)
C14—N2—H2N117 (2)O5—C11—C12121.3 (3)
C15—N2—H2N115 (2)C13—C12—C11132.0 (3)
O1—C1—O2121.2 (2)C13—C12—H12114.0
O1—C1—C2118.1 (2)C11—C12—H12114.0
O2—C1—C2120.7 (2)C12—C13—C14127.9 (2)
C3—C2—C1132.0 (3)C12—C13—H13116.0
C3—C2—H2114.0C14—C13—H13116.0
C1—C2—H2114.0O6—C14—N2123.0 (3)
C2—C3—C4128.4 (3)O6—C14—C13123.6 (3)
C2—C3—H3115.8N2—C14—C13113.4 (2)
C4—C3—H3115.8C20—C15—C16119.9 (3)
O3—C4—N1122.3 (3)C20—C15—N2123.9 (3)
O3—C4—C3123.1 (3)C16—C15—N2116.2 (2)
N1—C4—C3114.5 (2)C17—C16—C15119.7 (3)
C10—C5—C6119.8 (3)C17—C16—H16120.1
C10—C5—N1123.8 (2)C15—C16—H16120.1
C6—C5—N1116.4 (2)C16—C17—C18120.7 (3)
C7—C6—C5120.3 (3)C16—C17—H17119.6
C7—C6—H6119.8C18—C17—H17119.6
C5—C6—H6119.8C19—C18—C17119.4 (3)
C6—C7—C8119.9 (3)C19—C18—H18120.3
C6—C7—H7120.0C17—C18—H18120.3
C8—C7—H7120.0C20—C19—C18120.2 (3)
C9—C8—C7120.0 (3)C20—C19—H19119.9
C9—C8—H8120.0C18—C19—H19119.9
C7—C8—H8120.0C19—C20—C15120.1 (3)
C8—C9—C10120.6 (3)C19—C20—H20120.0
C8—C9—H9119.7C15—C20—H20120.0
O1—C1—C2—C3174.8 (3)O4—C11—C12—C13−175.7 (3)
O2—C1—C2—C3−5.1 (5)O5—C11—C12—C133.6 (5)
C1—C2—C3—C43.8 (5)C11—C12—C13—C14−5.2 (5)
C5—N1—C4—O32.6 (4)C15—N2—C14—O6−1.8 (5)
C5—N1—C4—C3−176.7 (3)C15—N2—C14—C13177.6 (2)
C2—C3—C4—O32.7 (5)C12—C13—C14—O6−1.1 (5)
C2—C3—C4—N1−178.0 (3)C12—C13—C14—N2179.4 (3)
C4—N1—C5—C10−9.5 (4)C14—N2—C15—C209.1 (4)
C4—N1—C5—C6171.4 (3)C14—N2—C15—C16−171.5 (3)
C10—C5—C6—C72.3 (4)C20—C15—C16—C17−0.4 (4)
N1—C5—C6—C7−178.5 (2)N2—C15—C16—C17−179.8 (2)
C5—C6—C7—C8−0.4 (4)C15—C16—C17—C18−0.6 (4)
C6—C7—C8—C9−1.2 (4)C16—C17—C18—C190.5 (4)
C7—C8—C9—C100.9 (4)C17—C18—C19—C200.5 (4)
C6—C5—C10—C9−2.5 (4)C18—C19—C20—C15−1.5 (4)
N1—C5—C10—C9178.4 (3)C16—C15—C20—C191.5 (4)
C8—C9—C10—C50.9 (4)N2—C15—C20—C19−179.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2o···O30.85 (1)1.63 (1)2.475 (3)172 (4)
O5—H5o···O60.86 (1)1.65 (1)2.496 (3)170 (3)
N1—H1n···O40.88 (1)2.00 (1)2.864 (3)166 (3)
N2—H2n···O1i0.89 (1)1.99 (1)2.859 (3)167 (3)

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2436).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Gonzalez-Rodriguez, J., Canoira, L., Calderon, C. E., Martinez-Ripoll, M. & García Blanco, S. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 199–203.
  • Home, S., Taylor, N., Colins, S. & Rodrigo, R. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 3047–3051.
  • Lynch, D. E. & McClenaghan, I. (2002). Acta Cryst. E58, o678–o679.
  • Parvez, M., Shahid, K., Shahzadi, S. & Ali, S. (2004a). Acta Cryst. E60, o2079–o2081.
  • Parvez, M., Shahzadi, S., Shahid, K. & Ali, S. (2004b). Acta Cryst. E60, o2082–o2084.
  • Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002a). Acta Cryst. E58, o1296–o1297.
  • Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002b). Acta Cryst. E58, o891–o892.
  • Santos-Sánchez, N. F., Salas-Coronado, R., Peña-Hueso, A. & Flores-Parra, A. (2007). Acta Cryst. E63, o4156.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o3849–o3851.
  • Westrip, S. P. (2009). publCIF In preparation.

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