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The title mol­ecule, C11H11NO3, is nearly planar, with the mean planes through the p-tolyl and maleamic acid groups inclined at an angle of 5.45 (3)°. The glide-related mol­ecules are linked by N—H...O and C—H...O intermolecular hydrogen bonds, forming infinite one-dimensional chains, which are assembled to form layers parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012023/ci6139sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012023/ci6139Isup2.hkl
Contains datablock I

CCDC reference: 193762

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.177
  • Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair,1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-(p-tolyl)-maleamic acid top
Crystal data top
C11H11NO3F(000) = 432
Mr = 205.21Dx = 1.326 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 6.769 (2) Åθ = 28.2–36.3°
b = 12.109 (1) ŵ = 0.81 mm1
c = 12.606 (1) ÅT = 293 K
β = 95.73 (1)°Needle, colourless
V = 1028.1 (3) Å30.38 × 0.31 × 0.25 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
1200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 75.5°, θmin = 5.1°
ω–2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 015
Tmin = 0.733, Tmax = 0.817l = 1515
2123 measured reflections3 standard reflections every 1 hr min
2047 independent reflections intensity decay: nil
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.178 w = 1/[σ2(Fo2) + (0.0899P)2 + 0.2017P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
2047 reflectionsΔρmax = 0.22 e Å3
167 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0101 (16)
Special details top

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
C10.2420 (5)0.1723 (2)0.4204 (2)0.0654 (8)
C20.2701 (5)0.2170 (2)0.5217 (2)0.0691 (9)
C30.2741 (5)0.3296 (2)0.5392 (2)0.0657 (8)
C40.2493 (4)0.4013 (2)0.45319 (18)0.0555 (7)
C50.2238 (5)0.3576 (2)0.35096 (19)0.0604 (7)
C60.2200 (5)0.2454 (2)0.3356 (2)0.0650 (8)
C70.2574 (4)0.5802 (2)0.55013 (17)0.0554 (7)
C80.2537 (5)0.6992 (2)0.52794 (19)0.0612 (8)
C90.2582 (5)0.7831 (2)0.5970 (2)0.0632 (8)
C100.2671 (5)0.7875 (2)0.7149 (2)0.0640 (8)
C110.2372 (6)0.0498 (2)0.4018 (3)0.0925 (12)
N0.2509 (4)0.51755 (17)0.46196 (16)0.0575 (6)
O10.2794 (4)0.69723 (15)0.77065 (13)0.0796 (7)
O20.2624 (4)0.87728 (16)0.75734 (15)0.0857 (8)
O30.2652 (3)0.54085 (14)0.64121 (13)0.0714 (6)
H20.291 (4)0.168 (3)0.584 (3)0.073 (8)*
H30.296 (4)0.358 (2)0.612 (2)0.069 (8)*
H50.198 (4)0.407 (2)0.293 (2)0.059 (7)*
H60.206 (4)0.220 (2)0.264 (2)0.059 (7)*
H80.244 (3)0.7152 (19)0.452 (2)0.048 (7)*
H90.260 (4)0.857 (3)0.569 (2)0.077 (9)*
H1N0.259 (4)0.552 (2)0.397 (2)0.069 (8)*
H1O0.28280.64400.73070.119*
H11A0.21950.01250.46740.139*
H11B0.12910.03190.34950.139*
H11C0.36000.02670.37670.139*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.099 (2)0.0458 (13)0.0535 (14)0.0008 (14)0.0188 (14)0.0053 (11)
C20.114 (3)0.0500 (14)0.0452 (14)0.0048 (16)0.0166 (14)0.0066 (12)
C30.115 (3)0.0475 (14)0.0366 (12)0.0009 (15)0.0151 (14)0.0010 (10)
C40.089 (2)0.0430 (13)0.0361 (11)0.0002 (12)0.0160 (11)0.0015 (9)
C50.100 (2)0.0465 (13)0.0365 (11)0.0051 (14)0.0139 (12)0.0003 (10)
C60.104 (3)0.0524 (14)0.0411 (13)0.0018 (15)0.0186 (13)0.0094 (11)
C70.0824 (19)0.0513 (13)0.0337 (10)0.0010 (13)0.0122 (11)0.0028 (9)
C80.104 (2)0.0456 (14)0.0364 (12)0.0017 (13)0.0161 (13)0.0004 (10)
C90.100 (2)0.0441 (14)0.0466 (14)0.0029 (14)0.0141 (13)0.0005 (11)
C100.100 (2)0.0477 (14)0.0453 (13)0.0028 (15)0.0119 (13)0.0077 (11)
C110.153 (4)0.0499 (16)0.076 (2)0.0029 (19)0.021 (2)0.0042 (15)
N0.0976 (18)0.0430 (11)0.0332 (9)0.0001 (11)0.0134 (10)0.0001 (8)
O10.152 (2)0.0502 (10)0.0370 (9)0.0007 (12)0.0135 (11)0.0030 (7)
O20.155 (2)0.0525 (11)0.0511 (11)0.0003 (12)0.0155 (12)0.0167 (8)
O30.1308 (18)0.0488 (10)0.0365 (9)0.0020 (11)0.0176 (9)0.0005 (7)
Geometric parameters (Å, º) top
C1—C21.382 (4)C7—N1.343 (3)
C1—C61.384 (4)C7—C81.467 (4)
C1—C111.502 (4)C8—C91.337 (3)
C2—C31.381 (4)C8—H80.97 (3)
C2—H20.99 (3)C9—C101.482 (3)
C3—C41.386 (3)C9—H90.97 (3)
C3—H30.98 (3)C10—O21.214 (3)
C4—C51.388 (3)C10—O11.298 (3)
C4—N1.412 (3)C11—H11A0.96
C5—C61.373 (4)C11—H11B0.96
C5—H50.94 (3)C11—H11C0.96
C6—H60.96 (3)N—H1N0.93 (3)
C7—O31.240 (3)O1—H1O0.82
C2—C1—C6117.2 (2)N—C7—C8113.5 (2)
C2—C1—C11122.0 (3)C9—C8—C7128.6 (2)
C6—C1—C11120.8 (3)C9—C8—H8119.0 (14)
C1—C2—C3122.2 (2)C7—C8—H8112.4 (14)
C1—C2—H2119.9 (18)C8—C9—C10132.6 (2)
C3—C2—H2117.9 (18)C8—C9—H9118.2 (19)
C4—C3—C2119.6 (2)C10—C9—H9109.2 (19)
C4—C3—H3121.0 (17)O2—C10—O1121.2 (2)
C2—C3—H3119.4 (17)O2—C10—C9118.3 (2)
C3—C4—C5118.8 (2)O1—C10—C9120.5 (2)
C3—C4—N124.3 (2)C1—C11—H11A109.5
C5—C4—N116.9 (2)C1—C11—H11B109.5
C6—C5—C4120.5 (2)H11A—C11—H11B109.5
C6—C5—H5121.3 (16)C1—C11—H11C109.5
C4—C5—H5118.0 (16)H11A—C11—H11C109.5
C5—C6—C1121.7 (2)H11B—C11—H11C109.5
C5—C6—H6117.1 (16)C7—N—C4128.9 (2)
C1—C6—H6121.2 (16)C7—N—H1N118.3 (17)
O3—C7—N123.0 (2)C4—N—H1N112.6 (17)
O3—C7—C8123.5 (2)C10—O1—H1O109.5
C6—C1—C2—C30.8 (5)O3—C7—C8—C90.2 (6)
C11—C1—C2—C3179.8 (3)N—C7—C8—C9180.0 (3)
C1—C2—C3—C40.0 (5)C7—C8—C9—C100.3 (6)
C2—C3—C4—C50.9 (5)C8—C9—C10—O2177.4 (4)
C2—C3—C4—N180.0 (3)C8—C9—C10—O12.5 (6)
C3—C4—C5—C61.0 (5)O3—C7—N—C40.7 (5)
N—C4—C5—C6179.8 (3)C8—C7—N—C4179.1 (3)
C4—C5—C6—C10.3 (5)C3—C4—N—C76.6 (5)
C2—C1—C6—C50.6 (5)C5—C4—N—C7174.3 (3)
C11—C1—C6—C5180.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O2i0.93 (3)1.96 (3)2.885 (3)177 (2)
O1—H1O···O30.821.682.495 (2)173
C3—H3···O30.98 (3)2.26 (2)2.866 (3)119 (2)
C8—H8···O1i0.97 (3)2.55 (2)3.498 (3)164 (2)
Symmetry code: (i) x, y+3/2, z1/2.
 

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