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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Apr 25;65(Pt 5):o1101. doi: 10.1107/S1600536809014627

N-Phenyl­maleamic acid

Kong Mun Lo a, Seik Weng Ng a,*
PMCID: PMC2977779  PMID: 21583915

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 ▶); Home et al. (1991 ▶); Lynch & McClenaghan (2002 ▶); Parvez et al. (2004a ▶,b ▶); Prasad et al. (2002a ▶,b ▶); Santos-Sánchez et al. (2007 ▶); Wardell et al. (2005 ▶).graphic file with name e-65-o1101-scheme1.jpg

Experimental

Crystal data

  • C10H9NO3

  • M r = 191.18

  • Monoclinic, Inline graphic

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

Supplementary Material

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

e-65-o1101-sup1.cif (18.4KB, cif)

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

e-65-o1101-Isup2.hkl (192.4KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2o⋯O3 0.85 (1) 1.63 (1) 2.475 (3) 172 (4)
O5—H5o⋯O6 0.86 (1) 1.65 (1) 2.496 (3) 170 (3)
N1—H1n⋯O4 0.88 (1) 2.00 (1) 2.864 (3) 166 (3)
N2—H2n⋯O1i 0.89 (1) 1.99 (1) 2.859 (3) 167 (3)
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Symmetry code: (i) Inline graphic.

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.

Fig. 1.

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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

C10H9NO3 F(000) = 800
Mr = 191.18 Dx = 1.479 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 1202 reflections
a = 12.7505 (4) Å θ = 2.6–27.4°
b = 10.5849 (5) Å µ = 0.11 mm−1
c = 14.1918 (6) Å T = 100 K
β = 116.299 (3)° Prism, colorless
V = 1717.1 (1) Å3 0.24 × 0.06 × 0.06 mm
Z = 8
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Data collection

Bruker SMART APEX diffractometer 2256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.062
graphite θmax = 27.5°, θmin = 1.8°
ω scans h = −16→16
11493 measured reflections k = −13→13
3925 independent reflections l = −14→18
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Refinement

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)] = 0.068 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208 H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.1139P)2] where P = (Fo2 + 2Fc2)/3
3925 reflections (Δ/σ)max = 0.001
269 parameters Δρmax = 0.96 e Å−3
4 restraints Δρmin = −0.36 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.41604 (16) 0.86211 (19) 0.61750 (16) 0.0173 (5)
O2 0.41080 (17) 0.6545 (2) 0.62972 (17) 0.0167 (5)
H2O 0.449 (3) 0.590 (3) 0.627 (3) 0.058 (14)*
O3 0.53761 (17) 0.4779 (2) 0.62899 (16) 0.0187 (5)
O4 0.91395 (17) 0.5468 (2) 0.60999 (17) 0.0216 (5)
O5 0.91031 (17) 0.75293 (19) 0.62870 (17) 0.0164 (5)
H5O 0.946 (3) 0.820 (2) 0.625 (3) 0.028 (10)*
O6 1.03470 (16) 0.93320 (19) 0.62520 (16) 0.0187 (5)
N1 0.7136 (2) 0.4490 (2) 0.62704 (18) 0.0122 (5)
H1N 0.771 (2) 0.492 (3) 0.623 (2) 0.019 (8)*
N2 1.2093 (2) 0.9624 (2) 0.62037 (19) 0.0149 (6)
H2N 1.2657 (19) 0.923 (3) 0.611 (2) 0.020 (8)*
C1 0.4591 (2) 0.7584 (3) 0.6178 (2) 0.0123 (6)
C2 0.5691 (2) 0.7538 (3) 0.6046 (2) 0.0109 (6)
H2 0.5933 0.8336 0.5906 0.013*
C3 0.6396 (2) 0.6584 (3) 0.6087 (2) 0.0157 (6)
H3 0.7079 0.6811 0.6018 0.019*
C4 0.6250 (2) 0.5224 (3) 0.6227 (2) 0.0135 (6)
C5 0.7229 (2) 0.3155 (3) 0.6348 (2) 0.0130 (6)
C6 0.8169 (2) 0.2612 (3) 0.6232 (2) 0.0118 (6)
H6 0.8710 0.3139 0.6125 0.014*
C7 0.8311 (2) 0.1321 (3) 0.6272 (2) 0.0164 (6)
H7 0.8945 0.0957 0.6188 0.020*
C8 0.7521 (2) 0.0547 (3) 0.6436 (2) 0.0149 (6)
H8 0.7609 −0.0345 0.6450 0.018*
C9 0.6615 (2) 0.1075 (3) 0.6576 (2) 0.0171 (6)
H9 0.6086 0.0544 0.6697 0.020*
C10 0.6463 (2) 0.2388 (3) 0.6541 (2) 0.0136 (6)
H10 0.5843 0.2749 0.6648 0.016*
C11 0.9577 (2) 0.6509 (3) 0.6128 (2) 0.0145 (6)
C12 1.0671 (2) 0.6566 (3) 0.5988 (2) 0.0171 (6)
H12 1.0910 0.5773 0.5836 0.021*
C13 1.1380 (2) 0.7531 (3) 0.6038 (2) 0.0095 (6)
H13 1.2070 0.7313 0.5977 0.011*
C14 1.1215 (2) 0.8896 (3) 0.6177 (2) 0.0140 (6)
C15 1.2203 (2) 1.0966 (3) 0.6289 (2) 0.0130 (6)
C16 1.3130 (2) 1.1490 (3) 0.6154 (2) 0.0169 (7)
H16 1.3645 1.0961 0.6012 0.020*
C17 1.3298 (2) 1.2781 (3) 0.6228 (2) 0.0163 (6)
H17 1.3934 1.3136 0.6143 0.020*
C18 1.2542 (2) 1.3569 (3) 0.6427 (2) 0.0165 (6)
H18 1.2659 1.4458 0.6471 0.020*
C19 1.1619 (2) 1.3044 (3) 0.6560 (2) 0.0147 (6)
H19 1.1097 1.3576 0.6689 0.018*
C20 1.1457 (2) 1.1746 (3) 0.6504 (2) 0.0147 (6)
H20 1.0835 1.1388 0.6612 0.018*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0154 (10) 0.0149 (12) 0.0241 (12) 0.0036 (8) 0.0111 (9) −0.0025 (9)
O2 0.0143 (10) 0.0118 (12) 0.0283 (12) 0.0004 (9) 0.0133 (9) 0.0026 (9)
O3 0.0165 (10) 0.0144 (12) 0.0298 (12) −0.0003 (8) 0.0145 (9) 0.0015 (9)
O4 0.0195 (10) 0.0149 (12) 0.0335 (13) −0.0042 (9) 0.0145 (10) −0.0003 (9)
O5 0.0150 (10) 0.0108 (12) 0.0280 (13) −0.0026 (8) 0.0138 (9) 0.0000 (9)
O6 0.0176 (10) 0.0126 (12) 0.0322 (13) −0.0003 (9) 0.0166 (9) −0.0029 (9)
N1 0.0159 (12) 0.0072 (13) 0.0159 (12) −0.0001 (10) 0.0091 (10) 0.0012 (10)
N2 0.0145 (12) 0.0157 (14) 0.0175 (13) 0.0013 (10) 0.0097 (10) 0.0010 (10)
C1 0.0106 (13) 0.0144 (16) 0.0125 (15) 0.0004 (11) 0.0057 (11) −0.0015 (11)
C2 0.0111 (13) 0.0083 (15) 0.0136 (14) −0.0008 (10) 0.0057 (11) −0.0022 (11)
C3 0.0166 (13) 0.0157 (17) 0.0185 (15) −0.0007 (12) 0.0112 (12) −0.0009 (12)
C4 0.0135 (13) 0.0150 (16) 0.0128 (14) 0.0017 (11) 0.0067 (11) −0.0012 (11)
C5 0.0149 (13) 0.0136 (15) 0.0106 (14) 0.0022 (12) 0.0056 (11) 0.0007 (12)
C6 0.0127 (13) 0.0119 (15) 0.0128 (14) −0.0023 (11) 0.0075 (11) 0.0004 (11)
C7 0.0161 (13) 0.0162 (17) 0.0165 (15) 0.0017 (12) 0.0068 (12) −0.0009 (12)
C8 0.0231 (14) 0.0050 (14) 0.0177 (15) −0.0012 (11) 0.0101 (12) −0.0002 (11)
C9 0.0166 (13) 0.0175 (17) 0.0171 (15) −0.0020 (12) 0.0075 (12) 0.0044 (12)
C10 0.0094 (12) 0.0195 (17) 0.0122 (15) 0.0029 (11) 0.0049 (11) 0.0005 (12)
C11 0.0151 (13) 0.0139 (16) 0.0159 (15) 0.0000 (12) 0.0082 (12) 0.0018 (12)
C12 0.0197 (14) 0.0182 (17) 0.0175 (15) 0.0032 (12) 0.0119 (12) 0.0005 (12)
C13 0.0114 (12) 0.0100 (14) 0.0075 (13) 0.0000 (10) 0.0044 (10) −0.0009 (10)
C14 0.0176 (13) 0.0158 (16) 0.0091 (14) 0.0013 (12) 0.0064 (11) 0.0009 (11)
C15 0.0176 (13) 0.0107 (15) 0.0084 (13) 0.0042 (11) 0.0037 (11) 0.0025 (11)
C16 0.0171 (14) 0.0180 (17) 0.0167 (15) 0.0033 (12) 0.0083 (12) 0.0000 (12)
C17 0.0105 (13) 0.0211 (17) 0.0164 (15) −0.0028 (12) 0.0051 (11) 0.0027 (13)
C18 0.0173 (14) 0.0139 (16) 0.0154 (15) −0.0052 (12) 0.0046 (12) −0.0002 (12)
C19 0.0135 (13) 0.0141 (16) 0.0155 (15) −0.0006 (12) 0.0057 (11) −0.0011 (12)
C20 0.0159 (13) 0.0149 (15) 0.0136 (15) 0.0020 (12) 0.0069 (11) 0.0005 (12)
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Geometric parameters (Å, °)

O1—C1 1.227 (3) C7—C8 1.395 (4)
O2—C1 1.307 (3) C7—H7 0.9500
O2—H2O 0.846 (10) C8—C9 1.375 (4)
O3—C4 1.249 (3) C8—H8 0.9500
O4—C11 1.227 (3) C9—C10 1.401 (4)
O5—C11 1.305 (3) C9—H9 0.9500
O5—H5O 0.857 (10) C10—H10 0.9500
O6—C14 1.247 (3) C11—C12 1.495 (4)
N1—C4 1.350 (3) C12—C13 1.344 (4)
N1—C5 1.419 (4) C12—H12 0.9500
N1—H1N 0.879 (10) C13—C14 1.486 (4)
N2—C14 1.345 (4) C13—H13 0.9500
N2—C15 1.427 (4) C15—C20 1.391 (4)
N2—H2N 0.886 (10) C15—C16 1.394 (4)
C1—C2 1.496 (4) C16—C17 1.379 (4)
C2—C3 1.335 (4) C16—H16 0.9500
C2—H2 0.9500 C17—C18 1.394 (4)
C3—C4 1.476 (4) C17—H17 0.9500
C3—H3 0.9500 C18—C19 1.389 (4)
C5—C10 1.387 (4) C18—H18 0.9500
C5—C6 1.403 (4) C19—C20 1.387 (4)
C6—C7 1.377 (4) C19—H19 0.9500
C6—H6 0.9500 C20—H20 0.9500
C1—O2—H2O 111 (3) C10—C9—H9 119.7
C11—O5—H5O 112 (2) C5—C10—C9 119.3 (3)
C4—N1—C5 128.0 (2) C5—C10—H10 120.3
C4—N1—H1N 114 (2) C9—C10—H10 120.3
C5—N1—H1N 118 (2) O4—C11—O5 120.7 (2)
C14—N2—C15 128.4 (2) O4—C11—C12 118.0 (3)
C14—N2—H2N 117 (2) O5—C11—C12 121.3 (3)
C15—N2—H2N 115 (2) C13—C12—C11 132.0 (3)
O1—C1—O2 121.2 (2) C13—C12—H12 114.0
O1—C1—C2 118.1 (2) C11—C12—H12 114.0
O2—C1—C2 120.7 (2) C12—C13—C14 127.9 (2)
C3—C2—C1 132.0 (3) C12—C13—H13 116.0
C3—C2—H2 114.0 C14—C13—H13 116.0
C1—C2—H2 114.0 O6—C14—N2 123.0 (3)
C2—C3—C4 128.4 (3) O6—C14—C13 123.6 (3)
C2—C3—H3 115.8 N2—C14—C13 113.4 (2)
C4—C3—H3 115.8 C20—C15—C16 119.9 (3)
O3—C4—N1 122.3 (3) C20—C15—N2 123.9 (3)
O3—C4—C3 123.1 (3) C16—C15—N2 116.2 (2)
N1—C4—C3 114.5 (2) C17—C16—C15 119.7 (3)
C10—C5—C6 119.8 (3) C17—C16—H16 120.1
C10—C5—N1 123.8 (2) C15—C16—H16 120.1
C6—C5—N1 116.4 (2) C16—C17—C18 120.7 (3)
C7—C6—C5 120.3 (3) C16—C17—H17 119.6
C7—C6—H6 119.8 C18—C17—H17 119.6
C5—C6—H6 119.8 C19—C18—C17 119.4 (3)
C6—C7—C8 119.9 (3) C19—C18—H18 120.3
C6—C7—H7 120.0 C17—C18—H18 120.3
C8—C7—H7 120.0 C20—C19—C18 120.2 (3)
C9—C8—C7 120.0 (3) C20—C19—H19 119.9
C9—C8—H8 120.0 C18—C19—H19 119.9
C7—C8—H8 120.0 C19—C20—C15 120.1 (3)
C8—C9—C10 120.6 (3) C19—C20—H20 120.0
C8—C9—H9 119.7 C15—C20—H20 120.0
O1—C1—C2—C3 174.8 (3) O4—C11—C12—C13 −175.7 (3)
O2—C1—C2—C3 −5.1 (5) O5—C11—C12—C13 3.6 (5)
C1—C2—C3—C4 3.8 (5) C11—C12—C13—C14 −5.2 (5)
C5—N1—C4—O3 2.6 (4) C15—N2—C14—O6 −1.8 (5)
C5—N1—C4—C3 −176.7 (3) C15—N2—C14—C13 177.6 (2)
C2—C3—C4—O3 2.7 (5) C12—C13—C14—O6 −1.1 (5)
C2—C3—C4—N1 −178.0 (3) C12—C13—C14—N2 179.4 (3)
C4—N1—C5—C10 −9.5 (4) C14—N2—C15—C20 9.1 (4)
C4—N1—C5—C6 171.4 (3) C14—N2—C15—C16 −171.5 (3)
C10—C5—C6—C7 2.3 (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—C19 0.5 (4)
C7—C8—C9—C10 0.9 (4) C17—C18—C19—C20 0.5 (4)
C6—C5—C10—C9 −2.5 (4) C18—C19—C20—C15 −1.5 (4)
N1—C5—C10—C9 178.4 (3) C16—C15—C20—C19 1.5 (4)
C8—C9—C10—C5 0.9 (4) N2—C15—C20—C19 −179.2 (2)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O2—H2o···O3 0.85 (1) 1.63 (1) 2.475 (3) 172 (4)
O5—H5o···O6 0.86 (1) 1.65 (1) 2.496 (3) 170 (3)
N1—H1n···O4 0.88 (1) 2.00 (1) 2.864 (3) 166 (3)
N2—H2n···O1i 0.89 (1) 1.99 (1) 2.859 (3) 167 (3)
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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

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

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-o1101-sup1.cif (18.4KB, cif)

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

e-65-o1101-Isup2.hkl (192.4KB, hkl)

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

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

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